Plant oil ceramides, synthesis method and use thereof

Abstract

The present invention belongs to the technical field of biological medicines. Disclosed are vegetable oil ceramides. The vegetable oil ceramides are obtained by reacting vegetable oil fatty acids with sphingosine compounds, the sphingosine compounds being selected from sphingosine, phytosphingosine and dihydrosphingosine, and the vegetable oil fatty acids being selected from olive oil fatty acids, tea oil fatty acids, sea buckthorn oil fatty acids, grape seed oil fatty acids, nut oil fatty acids, borage oil fatty acids, rose hip oil fatty acids, bean oil fatty acids, rice bran oil fatty acids, etc. Further disclosed in the present solution are a synthesis method for and the use of the vegetable oil ceramides. The vegetable oil ceramides exert excellent performance in areas of repairing natural skin barriers, anti-inflammation, tissue healing, aging resistance, etc., and have extensive application prospects in the fields of cosmetics, health-care products, biological medicines, etc.

Description

Vegetable oil ceramide and its synthesis method and use Technical Field

[0001] The present invention belongs to the field of biomedicine technology, and specifically relates to plant oil ceramide, a synthesis method and use thereof. Background Art

[0002] Ceramide (also known as molecular nail) is naturally present in the skin and is a crucial component of the skin barrier (stratum corneum), comprising up to 40-50% by weight. Ceramides are a class of lipids composed of a long-chain sphingosine base and fatty acids. The carbon chain length, degree of unsaturation, and number of hydroxyl groups in the sphingosine and fatty acid moieties can vary. Ceramides represent a class of compounds that exhibit excellent properties in regulating skin barrier function, restoring skin moisture, and enhancing adhesion between keratinocytes.

[0003] Due to the importance of ceramides, many cosmetics and pharmaceutical companies are researching and developing related products. Natural plant-derived ceramides, due to their more sustainable and environmentally friendly raw material sources and similar properties to skin ceramides, can form an effective skin barrier to prevent moisture loss and protect against external damage. They may become the next generation of environmentally friendly, safe and reliable ceramide products.

[0004] Vegetable oils are made from the fruits, seeds, and germs of oil-rich plants. After pre-processing, such as cleaning, shelling, crushing, softening, flaking, and extrusion, crude oil is extracted through mechanical pressing or solvent extraction, and then refined. The fatty acids in vegetable oils can moisturize and brighten the skin. Different vegetable oils vary in the content and types of fatty acids, and often contain other physiologically active substances.

[0005] Summary of the Invention

[0006] The purpose of the present invention is to provide a ceramide synthesized from vegetable oil fatty acids.

[0007] Another object of the present invention is to provide a method for synthesizing vegetable oil ceramide, which utilizes readily available vegetable oils or fatty acids from natural plant sources as raw materials.

[0008] Another object of the present invention is to provide uses of vegetable oil ceramides.

[0009] In order to achieve one of the above purposes, the present invention adopts the following technical solutions:

[0010] In a first aspect of the present invention, a vegetable oil ceramide is obtained by reacting a vegetable oil fatty acid with a sphingosine compound, wherein the sphingosine compound is selected from sphingosine, phytosphingosine, and dihydrosphingosine, and the vegetable oil fatty acid is selected from olive oil fatty acid, tea oil fatty acid, sea buckthorn oil fatty acid, grape seed oil fatty acid, nut oil fatty acid, borage oil fatty acid, rosehip oil fatty acid, soybean oil fatty acid, rice bran oil fatty acid, cottonseed oil fatty acid, South American tung oil fatty acid, watermelon seed oil fatty acid, coconut oil fatty acid, maple seed oil fatty acid, walnut oil fatty acid, avocado oil fatty acid, tomato seed oil fatty acid, sea sandalwood seed oil fatty acid, utilis utilis oil fatty acid, safflower seed oil fatty acid, Oil fatty acids, peony seed oil fatty acids, sunflower seed oil fatty acids, perilla seed oil fatty acids, linseed oil fatty acids, milk thistle oil fatty acids, shea butter fatty acids, evening primrose oil fatty acids, argan oil fatty acids, hemp seed oil fatty acids, white meadowfoam seed oil fatty acids, baobab seed oil fatty acids, cactus seed oil fatty acids, wheat germ oil fatty acids, sesame oil fatty acids, corn oil fatty acids, almond oil fatty acids, garlic fruit oil fatty acids, peanut oil fatty acids, black currant seed oil fatty acids, rapeseed oil fatty acids, hazelnut oil fatty acids, pumpkin seed oil fatty acids, DHA algae oil fatty acids, crabapple oil fatty acids, kiwi seed oil fatty acids, marula oil fatty acids, European plum seed oil fatty acids.

[0011] The reaction can be a chemical synthesis reaction (as described in detail below) or a microbial fermentation method, that is, using Pichia pastoris or Saccharomyces cerevisiae to ferment under certain conditions to obtain sphingosine compounds, and then adding fatty acids to finally obtain ceramides; or using vegetable oil as raw material, selecting a suitable strain to ferment to obtain vegetable oil ceramides.

[0012] Sphingosine refers to 2-amino-4-octadecene-1,3-diol, phytosphingosine refers to 2-amino-octadecane-1,3,4-triol, and dihydrosphingosine refers to 2-amino-octadecane-1,3-diol.

[0013] Furthermore, the vegetable oil fatty acid is obtained by hydrolyzing vegetable oil, such as tea oil fatty acid is obtained by hydrolyzing tea oil, and sea buckthorn oil fatty acid is obtained by hydrolyzing sea buckthorn seed oil or sea buckthorn fruit oil.

[0014] The fatty acid composition of olive oil is: 20-83wt% oleic acid, 7.5-20wt% palmitic acid, 3.5-70wt% linoleic acid, 0.5-5wt% stearic acid, 0.1-1.0wt% linolenic acid, 0-3.5wt% palmitoleic acid, 0-0.6wt% arachidic acid, 0-0.4wt% eicosenoic acid, 0-0.3wt% heptadecanoic acid, 0-0.3wt% heptadecanoic acid, 0-0.2wt% behenic acid, 0-0.2wt% tetracosanoic acid, and 0-0.05wt% myristic acid.

[0015] The fatty acid composition of tea oil is: 75-90 wt% oleic acid, 2-15 wt% linoleic acid, 1-10 wt% palmitic acid, 0.1-3 wt% stearic acid, 0.01-1 wt% linolenic acid and 0-0.5 wt% arachidic acid.

[0016] The fatty acid composition of sea buckthorn oil is: 20-35wt% oleic acid, 8-30wt% palmitic acid, 4-40wt% linoleic acid, 2-30wt% linolenic acid, 0.5-35wt% palmitoleic acid, 0.5-3wt% stearic acid and 0-1wt% myristic acid.

[0017] The fatty acid composition of grape seed oil is as follows: 55-85wt% of linoleic acid, 8-25wt% of oleic acid, 1-12wt% of palmitic acid, 0.5-7wt% of stearic acid, 0.01-2wt% of palmitoleic acid, 0.01-1wt% of linolenic acid and 0-1wt% of arachidic acid.

[0018] The fatty acid composition of nut oil is: 55-80wt% oleic acid, 12-35wt% palmitic acid, 2-10wt% palmitic acid, 0.4-3wt% linoleic acid, 0.1-3wt% arachidic acid, 0.2-5wt% stearic acid, 0.01-1wt% linolenic acid, 0.01-1wt% behenic acid, 0-1.5wt% myristic acid, and 0-3wt% arachidic acid.

[0019] The fatty acid composition of borage oil is: 20-40wt% gamma-linolenic acid, 30-45wt% linoleic acid, 15-25wt% oleic acid, 2-8wt% palmitic acid, 1-5wt% stearic acid, 0-2wt% arachidic acid, 0-2wt% arachidonic acid, and 0-2wt% erucic acid.

[0020] The fatty acid composition of rosehip oil is: 30-60wt% linoleic acid, 20-45wt% linolenic acid, 6-25wt% oleic acid, 0.1-3wt% stearic acid, 0.5-5wt% palmitic acid, 0.01-1wt% arachidic acid, and 0-1wt% arachidonic acid.

[0021] The composition of soybean oil fatty acids is: 50-75 wt% linoleic acid, 15-30 wt% oleic acid, 2-12 wt% palmitic acid, 1-10 wt% linolenic acid, 1-5 wt% stearic acid, 0-2 wt% arachidic acid, and 0-2 wt% behenic acid.

[0022] The fatty acid composition of rice bran oil is as follows: 40-60 wt% of oleic acid, 20-45 wt% of linoleic acid, 5-20 wt% of palmitic acid, 0.5-5 wt% of stearic acid, 0.1-2 wt% of linolenic acid and 0-2 wt% of arachidic acid.

[0023] The fatty acid composition of cottonseed oil is: 55-80 wt% of linoleic acid, 10-25 wt% of palmitic acid, 6-18 wt% of oleic acid, 1-3 wt% of stearic acid, 0.1-1 wt% of arachidic acid, 0.02-1 wt% of palmitoleic acid and 0.01-1 wt% of linolenic acid.

[0024] The fatty acid composition of the elm oil is: 45-68 wt% of linolenic acid, 20-40 wt% of linoleic acid, 5-12 wt% of oleic acid, 2-5 wt% of palmitic acid and 1-4 wt% of stearic acid.

[0025] The fatty acid composition of the watermelon seed oil is: 60-80 wt% of linoleic acid, 3-15 wt% of palmitic acid, 10-30 wt% of oleic acid and 1-5 wt% of stearic acid.

[0026] The coconut oil fatty acid comprises 20-70 wt% of lauric acid, 10-50 wt% of myristic acid, 10-20 wt% of palmitic acid, 2-10 wt% of stearic acid, 2-10 wt% of oleic acid, 0-3 wt% of capric acid and 0-3 wt% of caproic acid.

[0027] The fatty acid composition of the maple seed oil is: 25-48wt% linoleic acid, 20-40wt% oleic acid, 5-30wt% arachidic acid, 4-15wt% arachidic acid, 0.5-5wt% linolenic acid, 0.1-5wt% palmitic acid and 0.1-4wt% stearic acid.

[0028] The fatty acid composition of the walnut oil is: 40-75wt% of linoleic acid, 15-50wt% of oleic acid, 2-10wt% of palmitic acid, 0-5wt% of linolenic acid and 0-4wt% of stearic acid.

[0029] The fatty acid composition of avocado oil is: 50-80wt% oleic acid, 5-25wt% palmitoleic acid, 5-20wt% linoleic acid, 6-18wt% palmitic acid, 0.1-2wt% stearic acid, 0.1-1wt% linolenic acid, 0-1wt% arachidic acid, and 0-0.5wt% arachidic acid.

[0030] The fatty acid composition of the tomato seed oil is: 55-80 wt% of linoleic acid, 10-25 wt% of oleic acid, 3-20 wt% of palmitic acid, 1-8 wt% of stearic acid, 0.2-2 wt% of linolenic acid and 0-1 wt% of arachidic acid.

[0031] The fatty acid composition of the sea sandalwood seed oil is: 50-75wt% oleic acid, 15-40wt% linolenic acid, 0.5-10wt% stearic acid, 0-15wt% ximenynic acid, 0-15wt% nervonic acid, 0-2wt% behenic acid, 0-1wt% palmitic acid, and 0-1wt% linoleic acid.

[0032] The fatty acid composition of the prickle fruit oil is: 30-50 wt% of linoleic acid, 25-40 wt% of oleic acid, 10-25 wt% of palmitic acid, 3-10 wt% of stearic acid, 0-1 wt% of palmitoleic acid and 0-1 wt% of arachidic acid.

[0033] The fatty acid composition of safflower seed oil is: 70-90 wt% linoleic acid, 4-20 wt% oleic acid, 1-8 wt% palmitic acid, 0.01-2 wt% linolenic acid, 0-2 wt% stearic acid and 0-1 wt% arachidic acid.

[0034] The fatty acid composition of the peony seed oil is: 35-70 wt% of α-linolenic acid, 15-40 wt% of linoleic acid, 10-30 wt% of oleic acid, 0.1-5 wt% of palmitic acid, 0.1-5 wt% of stearic acid and 0-1 wt% of arachidic acid.

[0035] The fatty acid composition of the sunflower seed oil is: 55-75wt% of linoleic acid, 20-40wt% of oleic acid, 0.5-7wt% of stearic acid, 1-8wt% of palmitic acid, 0-2wt% of behenic acid and 0-1wt% of arachidic acid.

[0036] The fatty acid composition of the perilla seed oil is: 65-90 wt% alpha-linolenic acid, 4-30 wt% linoleic acid, 4-20 wt% oleic acid, 1-4 wt% stearic acid, 0-3.5 wt% palmitic acid and 0-0.6 wt% arachidonic acid.

[0037] The fatty acid composition of linseed oil is: 40-70 wt% of linolenic acid, 10-25 wt% of linoleic acid, 10-25 wt% of oleic acid, 1-8 wt% of palmitic acid, 1-8 wt% of stearic acid and 0-1 wt% of arachidic acid.

[0038] The fatty acid composition of milk thistle oil is: 50-75wt% linoleic acid, 15-45wt% oleic acid, 1-10wt% palmitic acid, 1-6wt% stearic acid, 0.2-4wt% arachidic acid, 0.5-4wt% behenic acid, 0.01-2.5wt% linolenic acid and 0-1.5wt% myristic acid.

[0039] The fatty acid composition of shea butter is: 35-60wt% oleic acid, 25-55wt% stearic acid, 2-10wt% linoleic acid, 0.5-10wt% palmitic acid, 0.1-2wt% arachidic acid, 0-1wt% linolenic acid and 0-1wt% behenic acid.

[0040] The fatty acid composition of evening primrose oil is: 55-88wt% linoleic acid, 3-20wt% oleic acid, 5-20wt% gamma-linolenic acid, 0.5-5wt% palmitic acid, 0-2wt% stearic acid, 0-2wt% arachidonic acid, and 0-1wt% behenic acid.

[0041] The fatty acid composition of argan oil is: 35-50wt% oleic acid, 30-50wt% linoleic acid, 5-15wt% palmitic acid, 2-8wt% stearic acid, 0.1-1wt% arachidic acid, 0.01-0.5wt% linolenic acid, 0-0.5wt% behenic acid, and 0-0.5wt% arachidic acid.

[0042] The fatty acid composition of the hemp seed oil is: 50-75wt% of linoleic acid, 5-30wt% of linolenic acid, 5-20wt% of oleic acid, 3-15wt% of palmitic acid and 1-5wt% of stearic acid.

[0043] The fatty acid composition of the meadowfoam seed oil is: 50-80wt% of cis-5-eicosenoic acid, 8-25wt% of cis-5,13-docosadienoic acid, 5-20wt% of erucic acid, 1-10wt% of cis-5-docosadienoic acid, 0-1wt% of oleic acid, and 0-1wt% of linoleic acid.

[0044] The fatty acid composition of baobab seed oil is: 30-50wt% oleic acid, 15-35wt% linoleic acid, 13-30wt% palmitic acid, 2-8wt% stearic acid, 0.5-5wt% linolenic acid, 0.2-2wt% arachidic acid, 0-1wt% palmitoleic acid and 0-0.5wt% myristic acid.

[0045] The fatty acid composition of the cactus seed oil is: 50-75wt% of linolenic acid, 10-30wt% of oleic acid, 5-15wt% of palmitoleic acid, 3-10wt% of palmitic acid, 3-8wt% of stearic acid and 0.1-1wt% of arachidic acid.

[0046] The fatty acid composition of wheat germ oil is as follows: 50-75wt% linoleic acid, 15-45wt% oleic acid, 2-10wt% palmitic acid, 1-8wt% linolenic acid, 0.1-1wt% arachidic acid, 0-0.5wt% stearic acid and 0-0.5wt% arachidic acid.

[0047] The fatty acid composition of sesame oil is: 45-70 wt% linoleic acid, 15-35 wt% oleic acid, 6-20 wt% palmitic acid, 0-2 wt% stearic acid, 0-1 wt% arachidic acid and 0-0.5 wt% linolenic acid.

[0048] The fatty acid composition of corn oil is: 50-70 wt% of linoleic acid, 20-35 wt% of oleic acid, 5-18 wt% of palmitic acid, 0.5-3 wt% of stearic acid, 0.01-1 wt% of linolenic acid and 0-1 wt% of arachidic acid.

[0049] The fatty acid composition of almond oil is: 55-80 wt% oleic acid, 15-35 wt% linoleic acid, 0.1-8 wt% palmitic acid, 0.5-2 wt% stearic acid, and 0.01-1 wt% linolenic acid.

[0050] The fatty acid composition of garlic fruit oil is as follows: 40-60 wt% of nervonic acid, 30-50 wt% of oleic acid, 5-12 wt% of arachidic acid, 0-2 wt% of palmitic acid and 0-2 wt% of linoleic acid.

[0051] The peanut oil fatty acid comprises 40-60 wt% of linoleic acid, 30-50 wt% of oleic acid, 4-12 wt% of palmitic acid, 0.5-5 wt% of stearic acid, 0-1 wt% of arachidic acid and 0-1 wt% of behenic acid.

[0052] The fatty acid composition of the blackcurrant seed oil is: 40-60 wt% of linoleic acid, 20-40 wt% of linolenic acid, 10-20 wt% of oleic acid, 1-8 wt% of palmitic acid, 0-2 wt% of stearic acid and 0-2 wt% of arachidic acid.

[0053] The fatty acid composition of rapeseed oil is: 50-80wt% oleic acid, 10-30wt% linoleic acid, 2-8wt% linolenic acid, 1-5wt% stearic acid, 0.5-5wt% palmitic acid, 0-1wt% arachidic acid, 0-1wt% arachidic acid and 0-1wt% erucic acid.

[0054] The fatty acid composition of hazelnut oil is: 70-90 wt% of oleic acid, 8-25 wt% of linoleic acid, 0.5-5 wt% of palmitic acid, 0.5-4 wt% of stearic acid, 0-0.5 wt% of linolenic acid and 0-0.5 wt% of palmitoleic acid.

[0055] The fatty acid composition of pumpkin seed oil is: 40-70wt% linoleic acid, 20-55wt% oleic acid, 3-10wt% palmitic acid, 1-5wt% stearic acid, 0.1-5wt% linolenic acid, 0-1wt% arachidic acid and 0-0.5wt% palmitoleic acid.

[0056] The composition of DHA algae oil fatty acids is: 50-75wt% DHA, 15-35wt% oleic acid, 3-15wt% palmitic acid, 0.1-1wt% stearic acid, 0.1-1wt% EPA, 0.01-0.5wt% linolenic acid, 0-0.5wt% arachidic acid, and 0-0.5wt% behenic acid.

[0057] The fatty acid composition of crabapple oil is: 30-50wt% oleic acid, 15-40wt% linoleic acid, 8-20wt% stearic acid, 6-20wt% palmitic acid, 0.2-1.5wt% arachidic acid, 0.05-2wt% linolenic acid, 0.05-1wt% palmitoleic acid, 0-1wt% behenic acid, and 0-0.5wt% arachidic acid.

[0058] The fatty acid composition of kiwifruit seed oil is: 45-70 wt% linolenic acid, 8-20 wt% linoleic acid, 5-20 wt% oleic acid, 2-10 wt% palmitic acid, and 0.5-5 wt% stearic acid.

[0059] The fatty acid composition of marula oil is: 65-85wt% oleic acid, 5-15wt% palmitic acid, 2-10wt% linoleic acid, 2-10wt% stearic acid, 0.2-2wt% arachidic acid, 0-1wt% arachidonic acid, and 0-0.5wt% linolenic acid.

[0060] The fatty acid composition of the European plum seed oil is: 60-80wt% oleic acid, 10-30wt% linoleic acid, 0.5-5wt% stearic acid, 0.5-3wt% palmitoleic acid, 0-7wt% palmitic acid and 0-1wt% linolenic acid.

[0061] The fatty acids in vegetable oils are affected by the plant variety, soil, climate, origin, picking season, and extraction process, and the content of each component will vary. For example, the main component of olive oil fatty acids is oleic acid. Other fatty acids include linoleic acid, palmitic acid, stearic acid, and linolenic acid, which are necessary components. However, palmitic acid, arachidic acid, eicosenoic acid, heptadecanoic acid, heptadecanedetonicoic acid, behenic acid, tetracosanoic acid, and myristic acid may not be present and are optional or non-essential components.

[0062] The vegetable oil ceramide is selected from at least two of oleic ceramide, linoleic ceramide, palmitic ceramide, linolenic ceramide, stearic ceramide, palmitoleic ceramide, arachidic ceramide, arachidonoyl ceramide, behenic ceramide, erucic ceramide, myristic ceramide, ceramide ceramide, lauric ceramide, eicosenoic ceramide, heptadecanoic ceramide, heptadecanoyl ceramide, tetracosenoic ceramide, DHA ceramide, EPA ceramide, decanoic ceramide, hexanoic ceramide, ximenynic ceramide, cis-5-eicosenoic ceramide, cis-5,13-docosadienoic ceramide, and cis-5-docosadienoic ceramide.

[0063] Specifically, the vegetable oil ceramide is selected from not more than 90 wt% of oleic acid ceramide, not more than 90 wt% of linoleic acid ceramide, not more than 30 wt% of palmitic acid ceramide, not more than 90 wt% of linolenic acid ceramide, not more than 55 wt% of stearic acid ceramide, not more than 35 wt% of palmitoleic acid ceramide, not more than 30 wt% of arachidic acid ceramide, not more than 15 wt% of oleic acid ceramide, not more than 4 wt% of behenic acid ceramide, not more than 20 wt% of erucic acid ceramide, not more than 50 wt% of myristic acid ceramide, not more than 60 wt% of ceramide, not more than 70 wt% of lauric acid ceramide, not more than 0. At least two of the following: 4wt% eicosenoic acid ceramide, not more than 0.3wt% heptadecanoic acid ceramide, not more than 0.3wt% heptadecanoic acid ceramide, not more than 0.2wt% tetracosanoic acid ceramide, not more than 75wt% DHA ceramide, not more than 1wt% EPA ceramide, not more than 3wt% decanoic acid ceramide, not more than 3wt% hexanoic acid ceramide, not more than 15wt% ximenynic acid ceramide, not more than 80wt% cis-5-eicosenoic acid ceramide, not more than 25wt% cis-5,13-docosadienoic acid ceramide, and not more than 10wt% cis-5-docosaenoic acid ceramide.

[0064] Linolenic acid ceramide refers to γ-linolenic acid ceramide and / or α-linolenic acid ceramide.

[0065] Plant oil ceramides also include vitamin A, vitamin B, vitamin C, vitamin D, vitamin E, vitamin K, proanthocyanidins, carotenoids (β-carotene), triacontanol, phytosterols, squalene, tea polyphenols, camellia glycosides, paeonol, saponins, polysaccharides, flavonoids, caffeic acid, vanillic acid, tyrosol, resorcinol, resveratrol, fruit acid, tocopherol, allantoin, lecithin (phospholipid), alkaloids, thymol, sterols (β-sitosterol, campesterol, phytosterol), amylase, maltase, protease, lectin, oryzanol, triterpenoid esters, triterpenes, aromatic acids, lycopene, bipyranocoumarins, amino acids, and trace elements, which are present in plant oil fatty acids but do not react with sphingosine compounds.

[0066] Oleic acid ceramide is obtained by the condensation reaction of oleic acid and sphingosine compounds, including oleic acid phytosphingosine ceramide, oleic acid sphingosine ceramide, and oleic acid dihydrosphingosine ceramide; linoleic acid ceramide is obtained by the condensation reaction of linoleic acid and sphingosine compounds, including linoleic acid phytosphingosine ceramide, linoleic acid sphingosine ceramide, and linoleic acid dihydrosphingosine ceramide; palmitic acid ceramide is obtained by the condensation reaction of palmitic acid and sphingosine compounds, including palmitic acid phytosphingosine ceramide, palmitic acid sphingosine ceramide, and palmitic acid dihydrosphingosine ceramide; other ceramides and so on.

[0067] The second aspect of the present invention is a method for synthesizing vegetable oil ceramide, comprising the following steps:

[0068] The vegetable oil fatty acid reacts with the sphingosine compound in the presence of a condensing agent and an organic base. The condensing agent is DCC or EDCI, and the organic base is DMAP, DIPEA, NMM or Et3N.

[0069] Furthermore, the molar ratio of the vegetable oil fatty acid, sphingosine compound, condensing agent and organic base is 1:(1-1.5):(1-2):(0.2-2), and the solvent of the reaction is at least one of dichloromethane, tetrahydrofuran, ethyl acetate and acetonitrile.

[0070] The vegetable oil purchased on the market is generally in the form of oil and needs to be hydrolyzed into vegetable oil fatty acids, so the following steps are also included:

[0071] Vegetable oils and fats are hydrolyzed through saponification to obtain vegetable oil fatty acids.

[0072] Furthermore, the saponification reaction is the hydrolysis of vegetable oil in potassium hydroxide solution.

[0073] Furthermore, the mass ratio of the vegetable oil to potassium hydroxide is 1:(1-2).

[0074] The third aspect of the present invention is the use of plant oil ceramide in cosmetics, medicines, dietary products or health products.

[0075] Furthermore, the plant oil ceramide has at least one of the following effects: skin barrier repair, tissue healing, anti-aging, anti-inflammatory, anti-photoaging, antioxidant, promotion of collagen synthesis, maintenance of elastin activity, and whitening.

[0076] A composition comprises vegetable oil ceramide, and the composition has at least one of the following effects: skin barrier repair, tissue healing, anti-aging, anti-inflammatory, anti-photoaging, anti-oxidation, promotion of collagen synthesis, maintenance of elastin activity, and whitening.

[0077] The composition contains acceptable excipients, including one or more of solubilizers, preservatives, antioxidants, pH regulators, penetration enhancers, liposomes, moisturizers, thickeners, chelating agents, skin feel regulators, surfactants, emulsifiers, flavors, and pigments; the composition is in the form of a cream, emulsion, solution, film, aerosol, or spray.

[0078] The present invention has the following beneficial effects:

[0079] The fatty acids in plant oils and sphingosine compounds naturally present in the skin are reacted mildly to produce plant oil ceramides, which exhibit excellent properties in repairing the skin's natural barrier, anti-oxidation, and anti-aging, and have broad application prospects in cosmetics, health products, biomedicine and other fields.

[0080] 1. Better results than single ceramides. Different ceramides have different effects due to their structural differences, and a single ceramide generally cannot achieve comprehensive results. This solution is based on a biomimetic approach, using natural plant oils or fatty acids as raw materials to synthesize composite ceramides to compensate for the differences in the effects of different ceramides. The trace fatty acids in plant oils can form trace ceramides, which play a complementary role in efficacy.

[0081] 2. Better effect than compound ceramide. In addition to fatty acids (or oils), vegetable oils also contain vitamin A, carotenoids, resveratrol, tocopherol, sterols, amino acids, trace elements and other ingredients. These nutrients have different physiological activities. Ceramide synthesized from vegetable oils has a synergistic effect with other active ingredients contained in vegetable oils. Compared with ceramides compounded in similar proportions, it has better effects.

[0082] 3. Lower cost. The method of the present invention quickly produces a composite of multiple ceramides. Vegetable oils or fatty acids are widely available, easily commercially available, and relatively low in cost, making them more environmentally friendly and economical. This is different from the idea of ​​mixing and compounding different single ceramides. Single-ingredient fatty acids not only have high raw material prices but also require the separate production of different ceramides and then compounding, increasing preparation costs.

[0083] 4. Simple synthesis method: The method of the present invention can be prepared by chemical synthesis to prepare multiple ceramides in one step, or by microbial fermentation. BRIEF DESCRIPTION OF THE DRAWINGS

[0084] Figures 1 and 2 are bar graphs of the cell proliferation activity test results of Example 37;

[0085] Figures 3, 4, and 5 are the results of the cell migration ability test in Example 38;

[0086] Figures 6, 7, and 8 are bar graphs of elastase inhibition rates in Example 39;

[0087] Figures 9, 10, and 11 are bar graphs showing the expression of IL-6 factor in the anti-inflammatory and repair efficacy test of Example 40;

[0088] Figures 12, 13, 14, 15, 16, and 17 are bar graphs of MMP1 expression levels in the anti-photoaging test of Example 41;

[0089] Figures 18, 19, 20, and 21 are bar graphs of DPPH radical scavenging rates in the antioxidant test of Example 42;

[0090] Figures 22, 23, and 24 are bar graphs of melanin content in the whitening activity test of Example 43. DETAILED DESCRIPTION

[0091] The present invention will be further described below with reference to specific examples. DCC refers to N,N'-dicyclohexylcarbodiimide, EDCI refers to 1-ethyl-(3-dimethylaminopropyl)carbodiimide, DMAP refers to 4-dimethylaminopyridine, Et3N refers to triethylamine, DIPEA refers to N,N-diisopropylethylamine, and NMM refers to N-methylmorpholine. Silica gel column chromatography used Qingdao Marine Silica Gel (particle size 0.040-0.063 mm). Thin layer chromatography (TLC) was performed using 60F254 silica gel plates, and TLC color development was performed using UV light (254 nm) or iodine.

[0092] Example 1

[0093] Synthesis of ceramide from olive oil fatty acids and sphingosine

[0094] Step 1: Dissolve 50 g of olive oil in 60 mL of tetrahydrofuran, cool in an ice bath, and add 100 mL of potassium hydroxide (25 wt%) solution dropwise. After the addition is complete, warm the mixture to room temperature and react until the reaction is complete as determined by TLC.

[0095] Post-treatment: dilute hydrochloric acid (3N) was added to adjust the pH value of the reaction system to 3, 150 mL of ethyl acetate was added to extract the aqueous phase, and 100 mL of saturated brine was added to wash once. The organic phase was added with anhydrous Na2SO4 to dry, filtered and concentrated in vacuo to obtain 40 g of olive oil fatty acid.

[0096] Step 2: Add 250 mL of olive oil fatty acid (50 mmol, molecular weight based on oleic acid), EDCI (75 mmol), and Et3N (75 mmol) into a round-bottom flask, then add 100 mL of dichloromethane, and stir at room temperature for 1 hour. Then, add sphingosine (50 mmol) to the reaction system and stir at room temperature until the reaction is complete as detected by TLC.

[0097] Post-treatment: water was added to quench the reaction, the organic layer was separated, dried, filtered, concentrated in vacuo, and then washed with a solvent to obtain olive oil ceramide. The product was analyzed by HPLC. HPLC chromatographic conditions: using a Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: (2 wt% water + 98 wt% methanol) both containing 0.1 wt% formic acid.

[0098] The retention times of the main components by HPLC were: oleic acid-sphingosine ceramide 20.7 min, linoleic acid-sphingosine ceramide 16.6 min.

[0099] The obtained product was analyzed by high performance liquid chromatography, and the mass ratios of oleic acid-sphingosine ceramide, palmitic acid-sphingosine ceramide, linoleic acid-sphingosine ceramide, stearic acid-sphingosine ceramide, and linolenic acid-sphingosine ceramide (NMR hydrogen spectrum was consistent with the standard spectrum) were 61.8%, 12.6%, 19.3%, 3.4%, and 0.6%, respectively. The remainder was other components with relatively small contents. This embodiment uses imported olive oil fatty acid, the main component of which is oleic acid, and the obtained product is mainly composed of oleic acid ceramide.

[0100] Oleic acid-sphingosine ceramide hydrogen spectrum: 1 H NMR(400MHz,Methanol-d4)δ7.70(d,J=8.9Hz,1H),5.69(dt,J=15.3,6.7Hz,1H),5 .45(dd,J=15.4,7.5Hz,1H),5.34(t,J=4.9Hz,2H),4.03(t,J=7.5Hz,1H),3.85(dd d,J=9.5,4.6,2.4Hz,1H),3.68(d,J=5.0Hz,2H),2.19(t,J=7.6Hz,2H),2.03(q,J= 6.9, 6.0Hz, 6H), 1.64–1.51 (m, 2H), 1.30 (d, J = 14.5Hz, 41H), 0.90 (t, J = 6.7Hz, 6H). Linoleic acid-sphingosine ceramide hydrogen spectrum: 1H NMR(400MHz, Methanol-d4)δ7.69(d,J=8.9Hz,1H),5.69(dt,J=15.3,6.7Hz,1H),5.46( dd,J=15.3,7.4Hz,1H),5.41–5.25(m,4H),4.03(t,J=7.5Hz,1H),3.85(tdd,J=7.5,4.7, 2.2Hz,1H),3.68(d,J=5.0Hz,2H),2.77(t,J=6.4Hz,2H),2.20(q,J=7.6,6.9Hz,2H),2.1 3–1.94(m,6H),1.67–1.49(m,2H),1.31(d,J=19.6Hz,40H),0.90(td,J=6.8,3.8Hz,6H).

[0101] The synthesis of ceramide from olive oil fatty acids, phytosphingosine and dihydrosphingosine was carried out in accordance with this example.

[0102] Example 2

[0103] Synthesis of Ceramide from Tea Oil Fatty Acids and Phytosphingosine

[0104] Step 1: Dissolve 50 g of tea oil in 60 mL of tetrahydrofuran, cool in an ice bath, and add 100 mL of potassium hydroxide (25 wt%) solution dropwise. After the addition is complete, warm the temperature to room temperature and react until the reaction is complete as detected by TLC.

[0105] Post-treatment: Add dilute hydrochloric acid (3N) to adjust the pH value of the reaction system to 3, add 150 mL of ethyl acetate to extract the aqueous phase, add 100 mL of saturated brine to wash once, add anhydrous Na2SO4 to dry the organic phase, filter and concentrate in vacuo to obtain 40.3 g of tea oil fatty acid.

[0106] Step 2: Add tea oil fatty acid (50 mmol, calculated as the main component fatty acid), DCC (60 mmol), and DMAP (10 mmol) into a 250 mL round-bottom flask, then add 100 mL of dichloromethane, and then stir at room temperature for 1 hour. Then, add phytosphingosine (60 mmol) to the reaction system and stir at room temperature until the reaction is completed as detected by TLC.

[0107] Post-treatment: The reaction solution was filtered to remove solids, and the filtrate was collected and washed with saturated sodium bicarbonate solution, 1N dilute hydrochloric acid and saturated brine respectively. The organic layer was separated, dried, filtered and concentrated in vacuo, and then washed with solvent to obtain tea oil ceramide. The product was analyzed by HPLC. HPLC chromatographic conditions: using Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using Innova! ODS-2 4.6*250mm, 5μm column, column temperature: 30°C, injection volume: 10μL, flow rate: 1.0mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5L / min, mobile phase: 100% methanol.

[0108] The HPLC retention times of each component are: linolenic acid-phytosphingosine ceramide 8.3 min, linoleic acid-phytosphingosine ceramide 9.5 min, palmitic acid-phytosphingosine ceramide 10.7 min, oleic acid-phytosphingosine ceramide 11.3 min, and stearic acid-phytosphingosine ceramide 13.9 min.

[0109] The obtained product was analyzed by high performance liquid chromatography, and the contents of oleic acid-phytosphingosine ceramide, linoleic acid-phytosphingosine ceramide, palmitic acid-phytosphingosine ceramide, stearic acid-phytosphingosine ceramide, and linolenic acid-phytosphingosine ceramide were 77%, 13%, 3%, 2%, and 1%, respectively, and the rest were other components with relatively small contents.

[0110] The synthesis of ceramide from tea oil fatty acids, sphingosine and dihydrosphingosine was carried out according to this example.

[0111] Example 3

[0112] Synthesis of ceramide from sea buckthorn oil fatty acids and dihydrosphingosine

[0113] Step 1: Dissolve 50 g of seabuckthorn seed oil in 60 mL of tetrahydrofuran, cool in an ice bath, and dropwise add 100 mL of potassium hydroxide (25 wt%) solution. After the addition is complete, warm the mixture to room temperature for reaction until the reaction is complete as determined by TLC.

[0114] Post-treatment: dilute hydrochloric acid (3N) was added to adjust the pH value of the reaction system to 3, 150 mL of ethyl acetate was added to extract the aqueous phase, and 100 mL of saturated brine was added to wash once. The organic phase was added with anhydrous Na2SO4 to dry, filtered and concentrated in vacuo to obtain 39.6 g of sea buckthorn oil fatty acids.

[0115] Step 2: Add sea buckthorn oil fatty acids (50 mmol, calculated as the main component fatty acids), EDCI (80 mmol), and Et3N (80 mmol) into a 250 mL round-bottom flask, then add 100 mL of dichloromethane, and then stir at room temperature for 1 hour. Then, add dihydrosphingosine (60 mmol) to the reaction system and stir at room temperature until the reaction is complete as detected by TLC.

[0116] Post-treatment: water was added to quench the reaction, the organic layer was separated, dried, filtered, concentrated in vacuo, and then washed with a solvent to obtain sea buckthorn oil ceramide. The product was analyzed by HPLC under the following chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0117] The HPLC retention times of each component are: linolenic acid-dihydrosphingosine ceramide 8.3 min, palmitoyl oleate-dihydrosphingosine ceramide 9.0 min, linoleic acid-dihydrosphingosine ceramide 9.6 min, palmitic acid-dihydrosphingosine ceramide 10.6 min, oleic acid-dihydrosphingosine ceramide 11.1 min, and stearic acid-dihydrosphingosine ceramide 13.6 min.

[0118] High performance liquid chromatography analysis of the obtained product showed that the contents of oleic acid-dihydrosphingosine ceramide, palmitic acid-dihydrosphingosine ceramide, linoleic acid-dihydrosphingosine ceramide, linolenic acid-dihydrosphingosine ceramide, palmitoyl oleate-dihydrosphingosine ceramide, and stearic acid-dihydrosphingosine ceramide were 28%, 27%, 6%, 25%, 7%, and 1%, respectively, and the rest were other components in smaller amounts.

[0119] The synthesis of ceramide from seabuckthorn oil fatty acids, sphingosine and phytosphingosine was carried out in accordance with this example.

[0120] Example 4

[0121] Synthesis of ceramide from grape seed oil fatty acids and phytosphingosine

[0122] Step 1: Dissolve 50 g of grape seed oil in 60 mL of tetrahydrofuran, cool in an ice bath, and dropwise add 100 mL of a 25 wt % potassium hydroxide solution. After the addition is complete, warm the mixture to room temperature for reaction until the reaction is complete as determined by TLC.

[0123] Post-treatment: dilute hydrochloric acid (3N) was added to adjust the pH value of the reaction system to 3, 150 mL of ethyl acetate was added to extract the aqueous phase, and 100 mL of saturated brine was added to wash once. The organic phase was added with anhydrous Na2SO4 to dry, filtered and concentrated in vacuo to obtain 40 g of grape seed oil fatty acid.

[0124] Step 2: Grape seed oil fatty acids (50 mmol, calculated as the main component fatty acid), EDCI (60 mmol), and DIPEA (60 mmol) were added to a 250 mL round-bottom flask, followed by 100 mL of dichloromethane, and then stirred at room temperature for 1 hour. Subsequently, phytosphingosine (60 mmol) was added to the reaction system and stirred at room temperature until the reaction was completed as detected by TLC.

[0125] Post-treatment: water was added to quench the reaction, the organic layer was separated, dried, filtered, concentrated in vacuo, and then washed with a solvent to obtain grape seed oil ceramide. The product was analyzed by HPLC. HPLC chromatographic conditions: using a Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova ODS-2 4.6*250mm, 5μm column, column temperature: 30°C, injection volume: 10μL, flow rate: 1.0mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5L / min, mobile phase: 100% methanol.

[0126] The HPLC retention times of each component are: palmitoyl oleate-phytosphingosine ceramide 8.0 min, linoleic acid-phytosphingosine ceramide 8.3 min, linoleic acid-phytosphingosine ceramide 9.4 min, palmitic acid-phytosphingosine ceramide 10.6 min, oleic acid-phytosphingosine ceramide 11.2 min, and stearic acid-phytosphingosine ceramide 13.8 min.

[0127] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-phytosphingosine ceramide, oleic acid-phytosphingosine ceramide, palmitic acid-phytosphingosine ceramide, stearic acid-phytosphingosine ceramide, palmitoyl oleate-phytosphingosine ceramide, and linolenic acid-phytosphingosine ceramide were 61%, 22%, 7%, 3%, 1%, and 1%, respectively, and the rest were other components with smaller contents.

[0128] Synthesis of ceramide from grape seed oil fatty acids, sphingosine and dihydrosphingosine was carried out in accordance with this example.

[0129] Example 5

[0130] Reference Example 2, nut oil fatty acids and sphingosine were used to synthesize nut oil ceramide, and the product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0131] The HPLC retention times of each component are: linolenic acid-sphingosine ceramide 7.9 min, palmitoyl sphingosine ceramide 8.2 min, linoleic acid-sphingosine ceramide 8.7 min, oleic acid-sphingosine ceramide 10.2 min, palmitic acid-sphingosine ceramide 10.4 min, arachidic acid-sphingosine ceramide 12.8 min, stearic acid-sphingosine ceramide 13.6 min, arachidic acid-sphingosine ceramide 17.8 min, and behenic acid-sphingosine ceramide 24.0 min.

[0132] The obtained product was analyzed by high performance liquid chromatography, and the contents of oleic acid-sphingosine ceramide, palmitoyl sphingosine ceramide, palmitic acid-sphingosine ceramide, linoleic acid-sphingosine ceramide, arachidic acid-sphingosine ceramide, stearic acid-sphingosine ceramide, linolenic acid-sphingosine ceramide, behenic acid-sphingosine ceramide, and arachidic acid-sphingosine ceramide were 58%, 24%, 5%, 3%, 1%, 4%, 0.5%, 0.5%, and 2%, respectively, and the rest were other components in smaller amounts.

[0133] The synthesis of ceramide from nut oil fatty acids, phytosphingosine and dihydrosphingosine was carried out in accordance with this example.

[0134] Example 6

[0135] Reference Example 3: Borage oil ceramide was synthesized from borage oil fatty acids and dihydrosphingosine. The product was analyzed by HPLC. Chromatographic conditions: Shimadzu HPLC (LC-2030C 3D Plus), using an Innova ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0136] The HPLC retention times of each component are: γ-linolenic acid-dihydrosphingosine ceramide 8.3 min, linoleic acid-dihydrosphingosine ceramide 9.5 min, palmitic acid-dihydrosphingosine ceramide 10.6 min, oleic acid-dihydrosphingosine ceramide 11.2 min, stearic acid-dihydrosphingosine ceramide 13.5 min, and erucic acid-dihydrosphingosine ceramide 18.7 min.

[0137] The obtained product was analyzed by high performance liquid chromatography, and the contents of γ-linolenic acid-dihydrosphingosine ceramide, linoleic acid-dihydrosphingosine ceramide, oleic acid-dihydrosphingosine ceramide, palmitic acid-dihydrosphingosine ceramide, stearic acid-dihydrosphingosine ceramide, and erucic acid-dihydrosphingosine ceramide were 27%, 44%, 19%, 4%, 2%, and 2%, respectively, and the rest were other components with smaller contents.

[0138] The synthesis of ceramide from borage oil fatty acids, sphingosine and phytosphingosine was carried out according to this example.

[0139] Example 7

[0140] Reference Example 2: Rosehip oil ceramide was synthesized from rosehip oil fatty acids and phytosphingosine, and the product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0141] The HPLC retention times of each component are: linolenic acid-phytosphingosine ceramide 8.3 min, linoleic acid-phytosphingosine ceramide 9.5 min, palmitic acid-phytosphingosine ceramide 10.6 min, oleic acid-phytosphingosine ceramide 11.2 min, arachidic acid-phytosphingosine ceramide 12.9 min, stearic acid-phytosphingosine ceramide 13.9 min, and arachidic acid-phytosphingosine ceramide 16.5 min.

[0142] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-phytosphingosine ceramide, linolenic acid-phytosphingosine ceramide, oleic acid-phytosphingosine ceramide, stearic acid-phytosphingosine ceramide, palmitic acid-phytosphingosine ceramide, arachidic acid-phytosphingosine ceramide, and arachidonic acid-phytosphingosine ceramide were 51%, 26%, 10%, 3%, 4%, 0.5%, and 1%, respectively, and the rest were other components with relatively small contents.

[0143] Synthesis of ceramide from rosehip oil fatty acids, sphingosine and dihydrosphingosine was carried out in accordance with this example.

[0144] Example 8

[0145] Synthesis of ceramide from soybean oil fatty acids and sphingosine

[0146] Soybean oil fatty acid (50 mmol, calculated as the main component fatty acid), EDCI (65 mmol), and DIPEA (65 mmol) were added to a 250 mL round-bottom flask, followed by 100 mL of dichloromethane, and then stirred at room temperature for 1 hour. Sphingosine (60 mmol) was then added to the reaction system and stirred at room temperature until the reaction was complete as detected by TLC.

[0147] Post-treatment: water was added to quench the reaction, the organic layer was separated, dried, filtered, concentrated in vacuo, and then washed with a solvent to obtain soybean oil ceramide. The product was analyzed by HPLC under the following chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova ODS-2 4.6*250 mm, 5 μm column, column temperature: 30 ° C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40 ° C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0148] The HPLC retention time of each component is: linolenic acid-sphingosine ceramide 7.9 min, linoleic acid-sphingosine ceramide 8.7 min, oleic acid-sphingosine ceramide 10.2 min, palmitic acid-sphingosine ceramide 10.5 min, stearic acid-sphingosine ceramide 13.5 min.

[0149] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-sphingosine ceramide, oleic acid-sphingosine ceramide, palmitic acid-sphingosine ceramide, linolenic acid-sphingosine ceramide, and stearic acid-sphingosine ceramide were 52%, 26%, 11%, 7%, and 2%, respectively, and the rest were other components with smaller contents.

[0150] The synthesis of ceramide from soybean oil fatty acid, phytosphingosine and dihydrosphingosine was carried out according to this example.

[0151] Example 9

[0152] Reference Example 8: Rice bran oil ceramide was synthesized from rice bran oil fatty acids and dihydrosphingosine. The product was analyzed by HPLC under the following chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0153] The HPLC retention times of each component are: linolenic acid-dihydrosphingosine ceramide 8.3 min, linoleic acid-dihydrosphingosine ceramide 9.5 min, palmitic acid-dihydrosphingosine ceramide 10.5 min, oleic acid-dihydrosphingosine ceramide 11.1 min, stearic acid-dihydrosphingosine ceramide 13.5 min, and arachidic acid-dihydrosphingosine ceramide 16.1 min.

[0154] The obtained product was analyzed by high performance liquid chromatography, and the contents of oleic acid-dihydrosphingosine ceramide, linoleic acid-dihydrosphingosine ceramide, palmitic acid-dihydrosphingosine ceramide, stearic acid-dihydrosphingosine ceramide, linolenic acid-dihydrosphingosine ceramide, and arachidic acid-dihydrosphingosine ceramide were 54%, 21%, 17%, 3%, 1%, and 2%, respectively, and the rest were other components with smaller contents.

[0155] The synthesis of ceramide from rice bran oil fatty acids, sphingosine, and phytosphingosine was carried out in accordance with this example.

[0156] Example 10

[0157] Synthesis of ceramide from cottonseed oil fatty acids and phytosphingosine

[0158] The first step: dissolve 50g of cottonseed oil in 60mL of tetrahydrofuran, cool in an ice bath, add 100mL of potassium hydroxide (25wt%) solution dropwise, warm to room temperature after the addition is complete, and react until the reaction is complete by TLC detection.

[0159] Post-treatment: dilute hydrochloric acid (3N) was added to adjust the pH value of the reaction system to 3, 150 mL of ethyl acetate was added to extract the aqueous phase, 100 mL of saturated brine was added to wash once, the organic phase was added with anhydrous Na2SO4 to dry, filtered and concentrated in vacuo to obtain 40.5 g of cottonseed oil fatty acid.

[0160] Step 2: Add cottonseed oil fatty acid (50 mmol, calculated as the main component fatty acid), EDCI (65 mmol), and NMM (65 mmol) to a 250 mL round-bottom flask, then add 100 mL of dichloromethane, and then stir at room temperature for 1 hour. Then, add phytosphingosine (55 mmol) to the reaction system and stir at room temperature until the reaction is complete as detected by TLC.

[0161] Post-treatment: water was added to quench the reaction, the organic layer was separated, dried, filtered, concentrated in vacuo, and then washed with a solvent to obtain cottonseed oil ceramide. The product was analyzed by HPLC under the following chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an InnovaL ODS-2 4.6*250 mm, 5 μm column, column temperature: 30 ° C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40 ° C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0162] The HPLC retention times of each component are: palmitoleic acid-phytosphingosine ceramide 8.1 min, linoleic acid-phytosphingosine ceramide 8.3 min, linoleic acid-phytosphingosine ceramide 9.5 min, palmitic acid-phytosphingosine ceramide 10.7 min, oleic acid-phytosphingosine ceramide 11.3 min, stearic acid-phytosphingosine ceramide 13.9 min, and arachidic acid-phytosphingosine ceramide 16.5 min.

[0163] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-phytosphingosine ceramide, palmitic acid-phytosphingosine ceramide, oleic acid-phytosphingosine ceramide, stearic acid-phytosphingosine ceramide, arachidic acid-phytosphingosine ceramide, palmitoleic acid-phytosphingosine ceramide, and linolenic acid-phytosphingosine ceramide were 74%, 12%, 7%, 2%, 1%, 1%, and 1%, respectively, and the rest were other components with smaller contents.

[0164] Synthesis of ceramide from cottonseed oil fatty acids, sphingosine, and dihydrosphingosine was carried out in accordance with this example.

[0165] Example 11

[0166] Reference Example 1: Synthesis of elata oil ceramide from elata oil fatty acids and sphingosine. The product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0167] The HPLC retention time of each component is: linolenic acid-sphingosine ceramide 7.9 min, linoleic acid-sphingosine ceramide 8.6 min, oleic acid-sphingosine ceramide 10.2 min, palmitic acid-sphingosine ceramide 10.4 min, stearic acid-sphingosine ceramide 13.6 min.

[0168] The obtained product was analyzed by high performance liquid chromatography, and the contents of linolenic acid-sphingosine ceramide, linoleic acid-sphingosine ceramide, oleic acid-sphingosine ceramide, palmitic acid-sphingosine ceramide, and stearic acid-sphingosine ceramide were 47%, 38%, 6%, 5%, and 1%, respectively, and the rest were other components with smaller contents.

[0169] Synthesis of ceramide from elata oil fatty acids, phytosphingosine and dihydrosphingosine was carried out in accordance with this example.

[0170] Example 12

[0171] Reference Example 10, watermelon seed oil ceramide was synthesized from watermelon seed oil fatty acids and dihydrosphingosine, and the product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0172] The HPLC retention time of each component is: linoleic acid-dihydrosphingosine ceramide 9.5 min, palmitic acid-dihydrosphingosine ceramide 10.5 min, oleic acid-dihydrosphingosine ceramide 11.1 min, stearic acid-dihydrosphingosine ceramide 13.5 min.

[0173] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-dihydrosphingosine ceramide, palmitic acid-dihydrosphingosine ceramide, oleic acid-dihydrosphingosine ceramide, and stearic acid-dihydrosphingosine ceramide were 66%, 8%, 23%, and 1%, respectively, and the rest were other components with smaller contents.

[0174] The synthesis of ceramide from watermelon seed oil fatty acids, phytosphingosine and sphingosine was carried out in accordance with this example.

[0175] Example 13

[0176] Synthesis of ceramide from coconut oil fatty acids and phytosphingosine

[0177] Coconut oil fatty acid (50 mmol, calculated as the main component fatty acid), EDCI (65 mmol), and Et3N (65 mmol) were added to a 250 mL round-bottom flask, and then 100 mL of dichloromethane was added, followed by stirring at room temperature for 1 hour. Subsequently, phytosphingosine (55 mmol) was added to the reaction system and stirred at room temperature until the reaction was completed as detected by TLC.

[0178] Post-treatment: water was added to quench the reaction, the organic layer was separated, dried, filtered, concentrated in vacuo, and then washed with a solvent to obtain coconut oil ceramide. The product was analyzed by HPLC under the following chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova ODS-2 4.6*250mm, 5μm column, column temperature: 30°C, injection volume: 10μL, flow rate: 1.0mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5L / min, mobile phase: 100% methanol.

[0179] The HPLC retention times of the components were as follows: caproic acid-phytosphingosine ceramide 5.7 min, capric acid-phytosphingosine ceramide 6.3 min, lauric acid-phytosphingosine ceramide 7.5 min, myristic acid-phytosphingosine ceramide 9.4 min, palmitic acid-phytosphingosine ceramide 10.7 min, oleic acid-phytosphingosine ceramide 11.3 min, and stearic acid-phytosphingosine ceramide 13.9 min.

[0180] The obtained product was analyzed by high performance liquid chromatography, and the contents of lauric acid-phytosphingosine ceramide, myristic acid-phytosphingosine ceramide, palmitic acid-phytosphingosine ceramide, stearic acid-phytosphingosine ceramide, oleic acid-phytosphingosine ceramide, capric acid-phytosphingosine ceramide, and caproic acid-phytosphingosine ceramide were 41%, 29%, 12%, 6%, 4%, 1%, and 3%, respectively, and the rest were other components with relatively small contents.

[0181] The synthesis of ceramide from coconut oil fatty acids, sphingosine and dihydrosphingosine was carried out according to this example.

[0182] Example 14

[0183] Reference Example 4: Acer truncatum seed oil ceramide was synthesized from Acer truncatum seed oil fatty acids and sphingosine, and the product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0184] The HPLC retention times of each component are: linolenic acid-sphingosine ceramide 7.9 min, linoleic acid-sphingosine ceramide 8.7 min, oleic acid-sphingosine ceramide 10.1 min, palmitic acid-sphingosine ceramide 10.4 min, arachidic acid-sphingosine ceramide 12.7 min, stearic acid-sphingosine ceramide 13.5 min, and arachidic acid-sphingosine ceramide 17.8 min.

[0185] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-sphingosine ceramide, oleic acid-sphingosine ceramide, arachidic acid-sphingosine ceramide, arachidonic acid-sphingosine ceramide, linolenic acid-sphingosine ceramide, palmitic acid-sphingosine ceramide, and stearic acid-sphingosine ceramide were 36%, 31%, 9%, 12%, 3%, 2%, and 3%, respectively, and the rest were other components with smaller contents.

[0186] The synthesis of ceramide from Acer truncatum seed oil fatty acids, phytosphingosine and dihydrosphingosine was carried out in accordance with this example.

[0187] Example 15

[0188] Reference Example 4, walnut oil fatty acids and dihydrosphingosine synthesis of walnut oil ceramide, the product was analyzed by HPLC, chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30 ° C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40 ° C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0189] The HPLC retention time of each component is: linolenic acid-dihydrosphingosine ceramide 8.3 min, linoleic acid-dihydrosphingosine ceramide 9.5 min, palmitic acid-dihydrosphingosine ceramide 10.6 min, oleic acid-dihydrosphingosine ceramide 11.1 min.

[0190] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-dihydrosphingosine ceramide, oleic acid-dihydrosphingosine ceramide, palmitic acid-dihydrosphingosine ceramide, and linolenic acid-dihydrosphingosine ceramide were 63%, 23%, 6%, and 4%, respectively, and the rest were other components with smaller contents.

[0191] The synthesis of ceramide from walnut oil fatty acids, phytosphingosine and sphingosine was carried out according to this example.

[0192] Example 16

[0193] Reference Example 1, avocado oil fatty acids and phytosphingosine synthesis of avocado oil ceramide, the product was analyzed by HPLC, chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innovation ODS-2 4.6 * 250 mm, 5 μm column, column temperature: 30 ° C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40 ° C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0194] The HPLC retention times of each component are: palmitoleic acid-phytosphingosine ceramide 8.0 min, linoleic acid-phytosphingosine ceramide 8.3 min, linoleic acid-phytosphingosine ceramide 9.5 min, palmitic acid-phytosphingosine ceramide 10.7 min, oleic acid-phytosphingosine ceramide 11.3 min, eicosapentaenoic acid-phytosphingosine ceramide 12.9 min, and stearic acid-phytosphingosine ceramide 13.9 min.

[0195] The obtained product was analyzed by high performance liquid chromatography, and the content ratios of oleic acid-phytosphingosine ceramide, palmitoleic acid-phytosphingosine ceramide, linoleic acid-phytosphingosine ceramide, palmitic acid-phytosphingosine ceramide, stearic acid-phytosphingosine ceramide, linolenic acid-phytosphingosine ceramide, and eicosapentaenoic acid-phytosphingosine ceramide were 70%, 10%, 7%, 8%, 1%, 0.5%, and 0.5%, respectively, and the rest were other components with relatively small contents.

[0196] The synthesis of ceramide from avocado oil fatty acids, sphingosine and dihydrosphingosine was carried out according to this example.

[0197] Example 17

[0198] Reference Example 4: Tomato seed oil ceramide was synthesized from tomato seed oil fatty acids and sphingosine, and the product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innovation ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0199] The HPLC retention times of each component are: linolenic acid-sphingosine ceramide 7.9 min, linoleic acid-sphingosine ceramide 8.7 min, oleic acid-sphingosine ceramide 10.2 min, palmitic acid-sphingosine ceramide 10.4 min, stearic acid-sphingosine ceramide 13.6 min, and arachidic acid-sphingosine ceramide 17.8 min.

[0200] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-sphingosine ceramide, oleic acid-sphingosine ceramide, palmitic acid-sphingosine ceramide, stearic acid-sphingosine ceramide, linolenic acid-sphingosine ceramide, and arachidic acid-sphingosine ceramide were 74%, 13%, 5%, 2%, 2%, and 1%, respectively, and the rest were other components with smaller contents.

[0201] The synthesis of ceramide from tomato seed oil fatty acids, phytosphingosine and dihydrosphingosine was carried out in accordance with this example.

[0202] Example 18

[0203] Reference Example 2: Synthesis of ceramide from maltodendron seed oil using fatty acids from maltodendron seed oil and dihydrosphingosine. The product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0204] The HPLC retention times of each component are: linolenic acid-dihydrosphingosine ceramide 8.3 min, oleic acid-dihydrosphingosine ceramide 11.1 min, stearic acid-dihydrosphingosine ceramide 13.5 min, ximenynic acid-dihydrosphingosine ceramide 17.2 min, behenic acid-dihydrosphingosine ceramide 21.8 min, and nervonic acid-dihydrosphingosine ceramide 24.1 min.

[0205] The obtained product was analyzed by high performance liquid chromatography, and the contents of oleic acid-dihydrosphingosine ceramide, linolenic acid-dihydrosphingosine ceramide, stearic acid-dihydrosphingosine ceramide, behenic acid-dihydrosphingosine ceramide, ximenynic acid-dihydrosphingosine ceramide, and nervonic acid-dihydrosphingosine ceramide were 50%, 31%, 3%, 2%, 8%, and 4%, respectively, and the rest were other components with smaller contents.

[0206] The synthesis of ceramide from phytosphingosine and sphingosine from sea sandalwood seed oil fatty acids was carried out in accordance with this example.

[0207] Example 19

[0208] Synthesis of ceramide from prickle fruit oil fatty acids and phytosphingosine

[0209] The first step: dissolve 50g of utilitarian fruit oil in 80mL of tetrahydrofuran, cool in an ice bath, add 100mL of potassium hydroxide (25wt%) solution dropwise, warm to room temperature after the addition is complete, and react until the reaction is complete by TLC detection.

[0210] Post-treatment: dilute hydrochloric acid (3N) was added to adjust the pH value of the reaction system to 3, 120 mL of ethyl acetate was added to extract the aqueous phase, 100 mL of saturated brine was added to wash once, the organic phase was added with anhydrous Na2SO4 to dry, filtered and concentrated in vacuo to obtain 40.6 g of utilitarian fruit oil fatty acid.

[0211] Step 2: Add utilitarian fruit oil fatty acids (50 mmol, calculated as the main component fatty acid), EDCI (55 mmol), and DMAP (55 mmol) into a 250 mL round-bottom flask, then add 100 mL of dichloromethane, and then stir at room temperature for 1 hour. Then, add phytosphingosine (55 mmol) to the reaction system and stir at room temperature until the reaction is complete as detected by TLC.

[0212] Post-treatment: water was added to quench the reaction, the organic layer was separated, dried, filtered, concentrated in vacuo, and then washed with a solvent to obtain ceramide from utilitarian fruit oil. The product was analyzed by HPLC under the following chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0213] The HPLC retention time of each component is: linoleic acid-phytosphingosine ceramide 9.5min, palmitic acid-phytosphingosine ceramide 10.7min, oleic acid-phytosphingosine ceramide 11.3min, stearic acid-phytosphingosine ceramide 13.9min, and arachidic acid-phytosphingosine ceramide 16.5min.

[0214] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-phytosphingosine ceramide, oleic acid-phytosphingosine ceramide, palmitic acid-phytosphingosine ceramide, stearic acid-phytosphingosine ceramide, and arachidic acid-phytosphingosine ceramide were 39%, 36%, 12%, 9%, and 1%, respectively, and the rest were other components with relatively small contents.

[0215] The synthesis of ceramide from utilis utilis oil fatty acids, sphingosine and dihydrosphingosine was carried out in accordance with this example.

[0216] Example 20

[0217] Reference Example 4, safflower seed oil fatty acids and sphingosine were used to synthesize safflower seed oil ceramide, and the product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0218] The HPLC retention times of each component are: linolenic acid-sphingosine ceramide 7.9 min, linoleic acid-sphingosine ceramide 8.7 min, oleic acid-sphingosine ceramide 10.2 min, palmitic acid-sphingosine ceramide 10.4 min, stearic acid-sphingosine ceramide 13.5 min, and arachidic acid-sphingosine ceramide 17.7 min.

[0219] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-sphingosine ceramide, oleic acid-sphingosine ceramide, palmitic acid-sphingosine ceramide, linolenic acid-sphingosine ceramide, stearic acid-sphingosine ceramide, and arachidic acid-sphingosine ceramide were 72%, 17%, 7%, 0.5%, 1%, and 0.5%, respectively. The rest were other components, and their contents were relatively small.

[0220] The synthesis of ceramide from safflower seed oil fatty acids, phytosphingosine and dihydrosphingosine was carried out in accordance with this example.

[0221] Example 21

[0222] Reference Example 3, peony seed oil fatty acids and dihydrosphingosine synthesis of peony seed oil ceramide, the product was analyzed by HPLC, chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30 ° C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40 ° C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0223] The HPLC retention time of each component is: α-linolenic acid-dihydrosphingosine ceramide 8.3 min, linoleic acid-dihydrosphingosine ceramide 9.5 min, palmitic acid-dihydrosphingosine ceramide 10.6 min, oleic acid-dihydrosphingosine ceramide 11.2 min, stearic acid-dihydrosphingosine ceramide 13.5 min.

[0224] The obtained product was analyzed by high performance liquid chromatography, and the contents of α-linolenic acid-dihydrosphingosine ceramide, linoleic acid-dihydrosphingosine ceramide, oleic acid-dihydrosphingosine ceramide, palmitic acid-dihydrosphingosine ceramide, and stearic acid-dihydrosphingosine ceramide were 43%, 34%, 16%, 1%, and 3%, respectively, and the rest were other components with smaller contents.

[0225] The synthesis of ceramide from peony seed oil fatty acids, phytosphingosine and sphingosine was carried out in accordance with this example.

[0226] Example 22

[0227] Reference Example 4, sunflower oil ceramide was synthesized from sunflower oil fatty acids and phytosphingosine, and the product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0228] The HPLC retention times of each component are: linoleic acid-phytosphingosine ceramide 9.4 min, palmitic acid-phytosphingosine ceramide 10.7 min, oleic acid-phytosphingosine ceramide 11.3 min, stearic acid-phytosphingosine ceramide 13.9 min, arachidic acid-phytosphingosine ceramide 16.5 min, and behenic acid-phytosphingosine ceramide 18.3 min.

[0229] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-phytosphingosine ceramide, oleic acid-phytosphingosine ceramide, stearic acid-phytosphingosine ceramide, palmitic acid-phytosphingosine ceramide, behenic acid-phytosphingosine ceramide, and arachidic acid-phytosphingosine ceramide were 58%, 27%, 4%, 5%, 2%, and 1%, respectively, and the rest were other components in smaller amounts.

[0230] Synthesis of ceramide from sunflower oil fatty acids, sphingosine and dihydrosphingosine was carried out in accordance with this example.

[0231] Example 23

[0232] Reference Example 1, perilla seed oil ceramide was synthesized from perilla seed oil fatty acids and sphingosine, and the product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova ODS-2 4.6*250mm, 5μm chromatographic column, column temperature: 30°C, injection volume: 10μL, flow rate: 1.0mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5L / min, mobile phase: 100% methanol.

[0233] The HPLC retention time of each component is: α-linolenic acid-sphingosine ceramide 7.9 min, linoleic acid-sphingosine ceramide 8.7 min, oleic acid-sphingosine ceramide 10.2 min, palmitic acid-sphingosine ceramide 10.4 min, stearic acid-sphingosine ceramide 13.6 min.

[0234] The obtained product was analyzed by high performance liquid chromatography, and the contents of α-linolenic acid-sphingosine ceramide, linoleic acid-sphingosine ceramide, oleic acid-sphingosine ceramide, stearic acid-sphingosine ceramide, and palmitic acid-sphingosine ceramide were 70%, 15%, 7%, 2%, and 2%, respectively, and the rest were other components with smaller contents.

[0235] The synthesis of ceramide from perilla seed oil fatty acids, phytosphingosine and dihydrosphingosine was carried out in accordance with this example.

[0236] Example 24

[0237] Reference Example 3: Flaxseed oil ceramide was synthesized from flaxseed oil fatty acids and dihydrosphingosine. The product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0238] The HPLC retention time of each component is: linolenic acid-dihydrosphingosine ceramide 8.3 min, linoleic acid-dihydrosphingosine ceramide 9.5 min, palmitic acid-dihydrosphingosine ceramide 10.7 min, oleic acid-dihydrosphingosine ceramide 11.1 min, stearic acid-dihydrosphingosine ceramide 13.6 min.

[0239] The obtained product was analyzed by high performance liquid chromatography, and the contents of linolenic acid-dihydrosphingosine ceramide, linoleic acid-dihydrosphingosine ceramide, oleic acid-dihydrosphingosine ceramide, palmitic acid-dihydrosphingosine ceramide, and stearic acid-dihydrosphingosine ceramide were 55%, 15%, 11%, 8%, and 7%, respectively, and the rest were other components with smaller contents.

[0240] The synthesis of ceramide from linseed oil fatty acids, phytosphingosine and sphingosine was carried out in accordance with this example.

[0241] Example 25

[0242] Reference Example 4, silybum oil ceramide was synthesized from silybum oil fatty acids and phytosphingosine, and the product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0243] The HPLC retention times of each component are: linolenic acid-phytosphingosine ceramide 8.2 min, linoleic acid-phytosphingosine ceramide 9.5 min, palmitic acid-phytosphingosine ceramide 10.7 min, oleic acid-phytosphingosine ceramide 11.3 min, stearic acid-phytosphingosine ceramide 13.9 min, arachidic acid-phytosphingosine ceramide 16.5 min, and behenic acid-phytosphingosine ceramide 18.3 min.

[0244] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-phytosphingosine ceramide, oleic acid-phytosphingosine ceramide, palmitic acid-phytosphingosine ceramide, stearic acid-phytosphingosine ceramide, arachidic acid-phytosphingosine ceramide, behenic acid-phytosphingosine ceramide, and linolenic acid-phytosphingosine ceramide were 65%, 18%, 5%, 3%, 3%, 2%, and 1%, respectively, and the rest were other components in smaller amounts.

[0245] The synthesis of ceramide from silymarin oil fatty acids, sphingosine and dihydrosphingosine was carried out in accordance with this example.

[0246] Example 26

[0247] Reference Example 4, shea butter fatty acids and sphingosine synthesis of shea butter ceramide, the product was analyzed by HPLC, chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova ODS-2 4.6*250mm, 5μm chromatographic column, column temperature: 30°C, injection volume: 10μL, flow rate: 1.0mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5L / min, mobile phase: 100% methanol.

[0248] The HPLC retention time of each component is: linoleic acid-sphingosine ceramide 8.7 min, oleic acid-sphingosine ceramide 10.2 min, palmitic acid-sphingosine ceramide 10.5 min, stearic acid-sphingosine ceramide 13.6 min, and arachidic acid-sphingosine ceramide 17.8 min.

[0249] The obtained product was analyzed by high performance liquid chromatography, and the contents of oleic acid-sphingosine ceramide, stearic acid-sphingosine ceramide, linoleic acid-sphingosine ceramide, palmitic acid-sphingosine ceramide, and arachidic acid-sphingosine ceramide were 37%, 48%, 3%, 7%, and 2%, respectively, and the rest were other components with smaller contents.

[0250] The synthesis of ceramide from shea butter fatty acids, phytosphingosine and dihydrosphingosine was carried out in accordance with this example.

[0251] Example 27

[0252] Reference Example 4, evening primrose oil ceramide was synthesized from evening primrose oil fatty acids and dihydrosphingosine, and the product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0253] The HPLC retention times of each component are: γ-linolenic acid-dihydrosphingosine ceramide 8.2 min, linoleic acid-dihydrosphingosine ceramide 9.5 min, palmitic acid-dihydrosphingosine ceramide 10.6 min, oleic acid-dihydrosphingosine ceramide 11.0 min, stearic acid-dihydrosphingosine ceramide 13.5 min, and arachidonic acid-dihydrosphingosine ceramide 14.0 min.

[0254] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-dihydrosphingosine ceramide, oleic acid-dihydrosphingosine ceramide, γ-linolenic acid-dihydrosphingosine ceramide, palmitic acid-dihydrosphingosine ceramide, stearic acid-dihydrosphingosine ceramide, and arachidonic acid-dihydrosphingosine ceramide were 65%, 16%, 10%, 2%, 2%, and 1%, respectively, and the rest were other components with smaller contents.

[0255] The synthesis of ceramide from evening primrose oil fatty acids, phytosphingosine and sphingosine was carried out in accordance with this example.

[0256] Example 28

[0257] Reference Example 1: Argan oil ceramide was synthesized from argan oil fatty acid and phytosphingosine, and the product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innoval ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0258] The HPLC retention times of each component are: linolenic acid-phytosphingosine ceramide 8.3 min, linoleic acid-phytosphingosine ceramide 9.5 min, palmitic acid-phytosphingosine ceramide 10.7 min, oleic acid-phytosphingosine ceramide 11.3 min, arachidic acid-phytosphingosine ceramide 12.9 min, stearic acid-phytosphingosine ceramide 13.9 min, arachidic acid-phytosphingosine ceramide 16.5 min, and behenic acid-phytosphingosine ceramide 18.3 min.

[0259] The obtained product was analyzed by high performance liquid chromatography, and the content ratios of oleic acid-phytosphingosine ceramide, linoleic acid-phytosphingosine ceramide, palmitic acid-phytosphingosine ceramide, stearic acid-phytosphingosine ceramide, arachidic acid-phytosphingosine ceramide, linolenic acid-phytosphingosine ceramide, behenic acid-phytosphingosine ceramide, and arachidonic acid-phytosphingosine ceramide were 50%, 33%, 5%, 6%, 0.5%, 0.5%, 0.5%, and 0.5%, respectively, and the rest were other components with relatively small contents.

[0260] The synthesis of ceramide from argan oil fatty acid, sphingosine and dihydrosphingosine was carried out in accordance with this example.

[0261] Example 29

[0262] Reference Example 2, hemp seed oil fatty acids and sphingosine synthesis of hemp seed oil ceramide, the product was analyzed by HPLC, chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30 ° C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40 ° C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0263] The HPLC retention time of each component is: linolenic acid-sphingosine ceramide 7.9 min, linoleic acid-sphingosine ceramide 8.7 min, oleic acid-sphingosine ceramide 10.2 min, palmitic acid-sphingosine ceramide 10.4 min, stearic acid-sphingosine ceramide 13.5 min.

[0264] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-sphingosine ceramide, linolenic acid-sphingosine ceramide, oleic acid-sphingosine ceramide, palmitic acid-sphingosine ceramide, and stearic acid-sphingosine ceramide were 69%, 10%, 7%, 8%, and 3.5%, respectively. The rest were other components with smaller contents.

[0265] The synthesis of ceramide from hempseed oil fatty acids, phytosphingosine and dihydrosphingosine was carried out according to this example.

[0266] Example 30

[0267] Reference Example 3, white meadowfoam seed oil fatty acids and phytosphingosine synthesis of white meadowfoam seed oil ceramide, the product was analyzed by HPLC, chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova ODS-2 4.6*250mm, 5μm chromatographic column, column temperature: 30°C, injection volume: 10μL, flow rate: 1.0mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5L / min, mobile phase: 2% water + 98% methanol.

[0268] The HPLC retention times of each component are: oleic acid-phytosphingosine ceramide 11.3 min, cis-5-eicosenoic acid-phytosphingosine ceramide 22.6 min, cis-5,13-docosadienoic acid-phytosphingosine ceramide 23.8 min, erucic acid-phytosphingosine ceramide 28.8 min, and cis-5-docosadienoic acid-phytosphingosine ceramide 32.6 min.

[0269] The obtained product was analyzed by high performance liquid chromatography, and the contents of cis-5-eicosenoic acid-phytosphingosine ceramide, cis-5,13-docosadienoic acid-phytosphingosine ceramide, erucic acid-phytosphingosine ceramide, cis-5-docosadienoic acid-phytosphingosine ceramide, and oleic acid-phytosphingosine ceramide were 55%, 21%, 15%, 4%, and 1%, respectively, and the rest were other components in small amounts.

[0270] The synthesis of ceramide from Limnanthes alba seed oil fatty acids, sphingosine and dihydrosphingosine was carried out in accordance with this example.

[0271] Example 31

[0272] Reference Example 3, baobab seed oil fatty acids and dihydrosphingosine synthesis of baobab seed oil ceramide, the product was analyzed by HPLC, chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30 ° C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40 ° C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0273] The HPLC retention times of each component are: linolenic acid-dihydrosphingosine ceramide 8.2 min, myristic acid-dihydrosphingosine ceramide 8.5 min, palmitoleic acid-dihydrosphingosine ceramide 8.9 min, linoleic acid-dihydrosphingosine ceramide 9.5 min, palmitic acid-dihydrosphingosine ceramide 10.7 min, oleic acid-dihydrosphingosine ceramide 11.1 min, stearic acid-dihydrosphingosine ceramide 13.5 min, and arachidic acid-dihydrosphingosine ceramide 16.0 min.

[0274] The obtained product was analyzed by high performance liquid chromatography, and the contents of oleic acid-dihydrosphingosine ceramide, linoleic acid-dihydrosphingosine ceramide, palmitic acid-dihydrosphingosine ceramide, stearic acid-dihydrosphingosine ceramide, linolenic acid-dihydrosphingosine ceramide, arachidic acid-dihydrosphingosine ceramide, palmitoleic acid-dihydrosphingosine ceramide, and myristic acid-dihydrosphingosine ceramide were 46%, 17%, 26%, 5%, 2%, 1%, 0.5%, and 0.5%, respectively, and the rest were other components with small contents.

[0275] The synthesis of ceramide from baobab seed oil fatty acids, phytosphingosine and sphingosine was carried out in accordance with this example.

[0276] Example 32

[0277] Reference Example 19, cactus seed oil fatty acids and sphingosine were used to synthesize cactus seed oil ceramide, and the product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0278] The HPLC retention times of each component are: linolenic acid-sphingosine ceramide 7.9 min, palmitoleic acid-sphingosine ceramide 8.2 min, oleic acid-sphingosine ceramide 10.2 min, palmitic acid-sphingosine ceramide 10.5 min, stearic acid-sphingosine ceramide 13.6 min, and arachidic acid-sphingosine ceramide 17.8 min.

[0279] The obtained product was analyzed by high performance liquid chromatography, and the contents of linolenic acid-sphingosine ceramide, oleic acid-sphingosine ceramide, palmitoleic acid-sphingosine ceramide, palmitic acid-sphingosine ceramide, stearic acid-sphingosine ceramide, and arachidic acid-sphingosine ceramide were 50%, 24%, 13%, 6%, 4.5%, and 1%, respectively, and the rest were other components with smaller contents.

[0280] The synthesis of ceramide from cactus seed oil fatty acids, phytosphingosine and dihydrosphingosine was carried out in accordance with this example.

[0281] Example 33

[0282] Reference Example 3, wheat germ oil ceramide was synthesized from wheat germ oil fatty acids and dihydrosphingosine, and the product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0283] The HPLC retention times of each component are: linolenic acid-dihydrosphingosine ceramide 8.3 min, linoleic acid-dihydrosphingosine ceramide 9.5 min, palmitic acid-dihydrosphingosine ceramide 10.6 min, oleic acid-dihydrosphingosine ceramide 11.1 min, stearic acid-dihydrosphingosine ceramide 13.5 min, arachidonic acid-dihydrosphingosine ceramide 14.0 min, and arachidonic acid-dihydrosphingosine ceramide 16.0 min.

[0284] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-dihydrosphingosine ceramide, oleic acid-dihydrosphingosine ceramide, palmitic acid-dihydrosphingosine ceramide, linolenic acid-dihydrosphingosine ceramide, arachidonic acid-dihydrosphingosine ceramide, stearic acid-dihydrosphingosine ceramide, and arachidonic acid-dihydrosphingosine ceramide were 53%, 32%, 8%, 2.5%, 1%, 0.5%, and 0.5%, respectively, and the rest were other components with small contents.

[0285] The synthesis of ceramide from wheat germ oil fatty acids, phytosphingosine and sphingosine was carried out according to this example.

[0286] Example 34

[0287] Reference Example 2, garlic fruit oil fatty acids and phytosphingosine synthesized garlic fruit oil ceramide, the product was analyzed by HPLC, HPLC chromatographic conditions: using Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), with Innovation ODS-2 4.6*250mm, 5μm chromatographic column, column temperature: 30°C, injection volume: 10μL, flow rate: 1.0mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5L / min, mobile phase: 100% methanol.

[0288] The HPLC retention times of each component are: linoleic acid-phytosphingosine ceramide 9.5 min, palmitic acid-phytosphingosine ceramide 10.7 min, oleic acid-phytosphingosine ceramide 11.3 min, arachidic acid-phytosphingosine ceramide 16.5 min, and nervonic acid-phytosphingosine ceramide 22.2 min.

[0289] The obtained product was analyzed by high performance liquid chromatography, and the contents of neuraminic acid-phytosphingosine ceramide, oleic acid-phytosphingosine ceramide, arachidic acid-phytosphingosine ceramide, palmitic acid-phytosphingosine ceramide, and linoleic acid-phytosphingosine ceramide were 52%, 35%, 8%, 2%, and 1%, respectively. The rest were other components, and the content was relatively small.

[0290] The synthesis of ceramide using garlic fruit oil fatty acids, sphingosine and dihydrosphingosine was carried out according to this example.

[0291] Example 35

[0292] Reference Example 2: Blackcurrant seed oil ceramide was synthesized from blackcurrant seed oil fatty acids and dihydrosphingosine, and the product was analyzed by HPLC. HPLC conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus) was used, using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 100% methanol.

[0293] The HPLC retention times of each component are: linolenic acid-dihydrosphingosine ceramide 8.3 min, linoleic acid-dihydrosphingosine ceramide 9.5 min, palmitic acid-dihydrosphingosine ceramide 10.6 min, oleic acid-dihydrosphingosine ceramide 11.1 min, stearic acid-dihydrosphingosine ceramide 13.5 min, and arachidic acid-dihydrosphingosine ceramide 16.0 min.

[0294] The obtained product was analyzed by high performance liquid chromatography, and the contents of linoleic acid-dihydrosphingosine ceramide, linolenic acid-dihydrosphingosine ceramide, oleic acid-dihydrosphingosine ceramide, palmitic acid-dihydrosphingosine ceramide, stearic acid-dihydrosphingosine ceramide, and arachidic acid-dihydrosphingosine ceramide were 45%, 31%, 13%, 5%, 2%, and 2%, respectively, and the rest were other components with smaller contents.

[0295] The synthesis of ceramide from blackcurrant seed oil fatty acids, phytosphingosine and sphingosine was carried out in accordance with this example.

[0296] Example 36

[0297] Reference Example 2, DHA algae oil fatty acids and sphingosine were synthesized to obtain DHA algae oil ceramide, and the product was analyzed by HPLC. Chromatographic conditions: Shimadzu high performance liquid chromatograph (LC-2030C 3D Plus), using an Innova! ODS-2 4.6*250 mm, 5 μm column, column temperature: 30°C, injection volume: 10 μL, flow rate: 1.0 mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5 L / min, mobile phase: 2% water + 98% methanol.

[0298] The HPLC retention times of each component are: linolenic acid-sphingosine ceramide 7.9 min, oleic acid-sphingosine ceramide 10.2 min, palmitic acid-sphingosine ceramide 10.5 min, stearic acid-sphingosine ceramide 13.6 min, EPA-sphingosine ceramide 15.6 min, arachidic acid-sphingosine ceramide 17.8 min, DHA-sphingosine ceramide 19.1 min, and behenic acid-sphingosine ceramide 24.0 min.

[0299] The obtained product was analyzed by high performance liquid chromatography, and the contents of DHA-sphingosine ceramide, oleic acid-sphingosine ceramide, palmitic acid-sphingosine ceramide, stearic acid-sphingosine ceramide, linolenic acid-sphingosine ceramide, EPA-sphingosine ceramide, arachidic acid-sphingosine ceramide, and behenic acid-sphingosine ceramide were 62%, 23%, 10%, 1%, 1%, 0.5%, 0.5%, and 0.5%, respectively. The rest were other components, and the content was relatively small.

[0300] The synthesis of ceramide from DHA algae oil fatty acids, phytosphingosine and dihydrosphingosine was carried out in accordance with this example.

[0301] The samples used in Examples 37 to 43 all refer to plant oil ceramides obtained by reacting corresponding plant oil fatty acids with phytosphingosine. For example, cottonseed oil ceramide refers to the ceramide obtained by reacting cottonseed oil fatty acids with phytosphingosine.

[0302] Example 37

[0303] MTT assay to detect the effects of compounds on cell proliferation

[0304] HaCaT cells were cultured at a rate of 1 × 10 4 Cells were seeded at a density of 100 μL / well in a 96-well plate and incubated overnight in an incubator. After 24 hours, the supernatant was discarded and 100 μL of culture medium containing samples of different concentrations was added. After further incubation for 24 hours, the culture medium was removed and 100 μL of thiazolyl blue (MTT) was added to each well. The absorbance at 450 nm was measured and the cell survival rate was calculated as A. 给药孔 / A 空白孔 ×100%.

[0305] As shown in Figure 1, cottonseed oil ceramide, tea oil ceramide, milk thistle oil ceramide, and perilla seed oil ceramide have a promoting effect on cell viability, with a stable concentration gradient, showing a significant effect of promoting cell proliferation and having good tissue repair ability. Among them, the cell survival rates of cottonseed oil ceramide (Figure 1a) at concentrations of 0.97657, 1.95313, 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, and 250 mg / L were 122.63%, 108.38%, 94.33%, 100.86%, 119.66%, 113.59%, 100.40%, 115.47%, and 124.87%, respectively, and the effective concentration was as low as 1 mg / L; the cell viability of tea oil ceramide (Figure 1b) at concentrations of 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, and 250 mg / L was 133.79%, 125.07%, 120.00%, 112.92%, 108.17%, 108.34%, and 102.18%, respectively. The effective concentration was as low as 4 mg / L, and the safe concentration was 250 mg / L; milk thistle oil ceramide (Figure 1c) at concentrations of The cell survival rates at concentrations of 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, 250, 500, and 1000 mg / L were 114.17%, 110.45%, 109.29%, 109.76%, 105.92%, 105.23%, 108.13%, 111.03%, and 130.31%, respectively. The effective concentration was as low as 4 mg / L, and the safe concentration was 1000 mg / L. The cell viability at the concentrations of 0.97657, 1.95313, 3.90625, 7.8125, 15.625, 31.25, 62.5 and 125 mg / L of amide (Figure 1d) was 121.42%, 129.10%, 132.97%, 129.16%, 120.44%, 122.89%, 111.23% and 118.53%, respectively. The effective concentration was as low as 4 mg / L and the safe concentration was as high as 1000 mg / L.

[0306] As shown in Figure 2, peony seed oil ceramide, borage oil ceramide, ceramide from sea sandalwood seed oil, and ceramide from South American tung oil vine oil have a promoting effect on cell viability, with a stable concentration gradient, showing a significant effect of promoting cell proliferation and having good tissue repair ability. Among them, the cell survival rates of peony seed oil ceramide (Figure 2a) at concentrations of 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, 250, 500, and 1000 mg / L were 109.76%, 106.50%, 107.43%, 105.11%, 105.34%, 107.55%, 116.61%, 124.04%, and 125.96%, respectively, and the effective concentration was as low as 4 m g / L, and the safe concentration is as high as 1000 mg / L; the cell survival rates of borage oil ceramide (Figure 2b) at concentrations of 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, 250, 500, and 1000 mg / L were 115.13%, 110.87%, 108.06%, 108.89%, 107.02%, 111.49%, 114.09%, 114.61%, The cell survival rates of ceramide from sea sandalwood seed oil (Figure 2c) at concentrations of 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, 250, 500, and 1000 mg / L were 132.61%, 124.80%, 118.90%, 123.14%, 117.91%, 129.79%, 130.79%, 138.51%, and 131.20%, respectively. The effective concentration was as low as 4 mg / L, and the safe concentration was as high as 1000 mg / L. / L, and the safe concentration is 1000 mg / L; the cell survival rates of ceramide from South American Elaeagnus truncatula oil at concentrations of 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, 250, 500, and 1000 mg / L (Figure 2d) were 115.55%, 113.88%, 111.80%, 111.39%, 112.32%, 109.52%, 113.05%, 115.03%, and 131.98%, respectively. The effective concentration was as low as 4 mg / L, and the safe concentration was as high as 1000 mg / L.

[0307] The effect of ceramide 2 on cell proliferation activity was tested using the same method. The cell survival rates at concentrations of 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, 250, 500, and 1000 mg / L were 61.49%, 60.03%, 55.41%, 54.64%, 53.37%, 46.95%, 44.05%, 40.35%, and 39.42%, respectively. It has an inhibitory effect on cell proliferation, and its tissue repair potential is inferior to that of plant oil ceramide.

[0308] Example 38

[0309] Cell migration to assess skin barrier repair

[0310] Principle: When cells grow to a fused monolayer state, a scratch tool is used to create a blank area on the fused monolayer of cells. The cells in the blank area are removed by mechanical force. After a period of culture, the migration of cells to the cell-free area is observed. The migration distance of the cells is measured to reflect the migration ability of the cells.

[0311] Steps:

[0312] 1. Mark the culture plate. First, use a marker pen and a ruler to evenly mark horizontal lines on the back of the 6-well plate, approximately every 0.5 to 1 cm, across the wells. Make at least 5 lines per well. Be careful not to make the lines too thick.

[0313] 2. Add about 5×10 cells to the well. 5 cells (the number of different cells varies and is adjusted according to the growth rate of the cells). The inoculation principle is that the fusion rate reaches 100% after overnight.

[0314] 3. Streak the cells. On the second day, use the pipette tip, perpendicular to the cell plane, to scratch the cell layer along the line drawn on the back of the plate on the first day (it is best to use the same pipette tip between different wells).

[0315] 4. Wash the cells. After the scratch is completed, wash the cells three times with sterile PBS to remove the non-adherent cells, that is, the cells that were scratched during the scratching process. The gaps left after the scratching are clearly visible, and then replace with fresh serum-free medium.

[0316] 5. Cell Culture and Observation. Samples were diluted with culture medium (5 mg / L for ceramides from milk thistle oil, perilla seed oil, peony seed oil, ceramides from tamarisk seed oil, borage oil, and ceramides from elatior oleifera oil; 20 mg / L for ceramides from tea oil, safflower seed oil, cottonseed oil, watermelon seed oil, acer truncatum seed oil, and coconut oil; and 100 mg / L for ceramide 3B) and added to cell culture dishes. The cells were cultured in a 37°C, 5 wt% CO2 incubator. After 24 hours, the cells were removed, the scratch width was observed under a microscope, and photographs were taken. The healing rate was calculated using Image J software.

[0317] As shown in Figure 3, the scratch width in the experimental group was narrower than that in the solvent control group, indicating that ceramides from milk thistle oil, perilla seed oil, peony seed oil, and ceramides from tamarisk seed oil possessed superior tissue healing abilities. The healing rate after 24 hours in the solvent control group was 27.33%, while that of ceramides from milk thistle oil (Figure 3a) was 90.23%, and that of ceramide 3B was 59.32%. The healing rates after 24 hours in the solvent control group were 48.35%, 92.41%, and 59.32% for ceramide 3B, respectively. The healing rates after 24 hours in the solvent control group were 32.58%, 93.21%, and 59.32% for ceramide 3B, respectively. The healing rate of the solvent control group after 24 hours was 29.58%, the healing rate of the ceramide of sea sandalwood seed oil (Figure 3d) after 24 hours was 94.26%, and the healing rate of ceramide 3B after 24 hours was 59.32%.

[0318] As shown in Figure 4, the scratch width in the experimental group was narrower than that in the solvent control group, indicating that borage oil ceramide, safflower oil ceramide, tea oil ceramide, and safflower oil ceramide have better tissue healing ability. The healing rate of the solvent control group after 24 hours was 29.58%, the healing rate of borage oil ceramide (Figure 4a) after 24 hours was 82.31%, and the healing rate of ceramide 3B after 24 hours was 59.32%. The healing rate of the solvent control group after 24 hours was 29.58%, the healing rate of safflower oil ceramide (Figure 4b) after 24 hours was 92.71%, and the healing rate of ceramide 3B after 24 hours was 59.32%. The healing rate of the solvent control group after 24 hours was 34.25%, the healing rate of tea oil ceramide (Figure 4c) after 24 hours was 88.75%, and the healing rate of ceramide 3B after 24 hours was 59.32%. The healing rate of the solvent control group after 24 hours was 41.25%, the healing rate of safflower seed oil ceramide (Figure 4d) after 24 hours was 94.25%, and the healing rate of ceramide 3B after 24 hours was 59.32%.

[0319] As shown in Figure 5, the scratch width in the experimental group was narrower than that in the solvent control group, indicating that cottonseed oil ceramide, watermelon seed oil ceramide, maple seed oil ceramide, and coconut oil ceramide have better tissue healing ability. The healing rate of the solvent control group after 24 hours was 38.22%, the healing rate of cottonseed oil ceramide (Figure 5a) after 24 hours was 96.21%, and the healing rate of ceramide 3B after 24 hours was 59.32%. The healing rate of the solvent control group after 24 hours was 35.21%, the healing rate of watermelon seed oil ceramide (Figure 5b) after 24 hours was 88.53%, and the healing rate of ceramide 3B after 24 hours was 59.32%. The healing rate of the solvent control group after 24 hours was 31.38%, the healing rate of maple seed oil ceramide (Figure 5c) after 24 hours was 87.22%, and the healing rate of ceramide 3B after 24 hours was 59.32%. The healing rate of the solvent control group after 24 hours was 29.58%, the healing rate of coconut oil ceramide (Figure 5d) after 24 hours was 82.31%, and the healing rate of ceramide 3B after 24 hours was 59.32%.

[0320] Therefore, the compound of the present invention significantly improves the cell healing rate, has good skin tissue repair activity, and is more effective than ceramide 3B.

[0321] Example 39

[0322] Elastase inhibition assay to test anti-aging effects

[0323] Elastase inhibition method: Take 2 mL of 2 mg / mL elastase solution, add samples of different concentrations, vortex mix thoroughly, shake at 37°C, 400 rpm for 20 min, immediately add 5 mL of 0.5 mol / L phosphate buffer (pH 6.0), vortex mix, take an appropriate amount of the mixture into a 2 mL centrifuge tube, centrifuge at 9391 × g for 10 min, accurately pipette 200 μL of the supernatant into a 96-well plate, measure the absorbance at a wavelength of 495 nm using a microplate reader, and simultaneously perform spectral scanning from 400 to 800 nm.

[0324] The substrate plus enzyme solution served as the blank control group, the substrate plus enzyme and sample solution served as the enzyme inhibition group, and the substrate plus sample without enzyme solution served as background subtraction. Each group was set up in triplicate. Inhibition rate (%) = [1 – (An – An′) / (A0 – A0′)] × 100%, where A0 is the absorbance with enzyme but no sample, A0′ is the absorbance with substrate alone but no sample or enzyme, An is the absorbance with sample solution alone, and An′ is the absorbance with sample but no enzyme. If An′ > An, it indicates a promoting effect. Promotion rate (%) = [1 – (An′ – An) / (A0 – A0′)] × 100%.

[0325] The results are shown in Figures 6 to 8 and the table below. The compounds of the present invention have good inhibitory effects on elastase at different concentrations, while the inhibitory effect of ceramide 2 is not as good as that of plant oil ceramide at the same concentration.

[0326] Example 40

[0327] LPS-induced cell assay to detect anti-inflammatory and repair effects

[0328] B16 mouse melanoma cells were cultured at a density of 1×10 4 Cells were seeded in 96-well plates at 100 μg / well and allowed to adhere overnight in an incubator. After 24 hours, the supernatant was discarded and 100 μL of samples diluted in DMEM medium at varying concentrations were added. A negative control group consisted of DMEM medium without sample. Three replicates were plated in each group and incubated in a 5 wt% CO2, 37°C environment. Two hours after administration, 10 μg / mL LPS was added to the lipopolysaccharide model group and the experimental group and incubated for 24 hours. After the reaction, 50 μL of the cell supernatant was collected and intracellular IL-6 gene expression was detected using an IL-6 ELISA kit.

[0329] As shown in Figure 9a, under the stimulation of LPS at a working concentration of 10 μg / mL, the IL-6 level was 10.95 times the basal level. Under the action of rapeseed oil ceramide at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, the IL-6 factor level was significantly reduced, which were 0.87, 0.64, 0.52, and 0.16 times that of the LPS model group, respectively, in a dose-dependent manner; As shown in Figure 9b, under the stimulation of LPS at a working concentration of 10 μg / mL, the IL-6 level was 10.16 times the basal level. Under the action of milk thistle oil ceramide at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, the IL-6 factor level was significantly reduced, which were 0.70, 0.45, 0.27, and 0.09 times that of the LPS model group, respectively, in a dose-dependent manner; As shown in Figure 9c, under the stimulation of LPS at a working concentration of 10 μg / mL, the IL-6 level was 10.16 times the basal level. Under the action of perilla seed oil ceramide at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, the IL-6 factor level was significantly reduced, which were 0.89, 0.66, 0.59, and 0.25 times that of the LPS model group, respectively, in a dose-dependent manner; as shown in Figure 9d, under the stimulation of LPS at a working concentration of 10 μg / mL, the IL-6 level was 11.51 times the basal level. Under the action of sunflower seed oil ceramide at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, the IL-6 factor level was significantly reduced, which were 0.84, 0.68, 0.52, and 0.31 times that of the LPS model group, respectively, in a dose-dependent manner.

[0330] As shown in Figure 10a, under the stimulation of LPS at a working concentration of 10 μg / mL, the IL-6 level was 10.16 times that of the basal level. Under the action of peony seed oil ceramide at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, the IL-6 factor level was significantly reduced, which were 0.99, 0.74, 0.48, and 0.22 times that of the LPS model group, respectively, in a dose-dependent manner; As shown in Figure 10b, under the stimulation of LPS at a working concentration of 10 μg / mL, the IL-6 level was 10.16 times that of the basal level. Under the action of safflower seed oil ceramide at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, the IL-6 factor level was significantly reduced, which were 0.94, 0.69, 0.56, and 0.22 times that of the LPS model group, respectively, in a dose-dependent manner; As shown in Figure 10c, under the stimulation of LPS at a working concentration of 10 μg / mL, the IL-6 level was 10.16 times the basal level. Under the action of ceramide from sea sandalwood seed oil at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, the IL-6 factor level was significantly reduced, which were 0.99, 0.74, 0.53, and 0.27 times that of the LPS model group, respectively, in a dose-dependent manner; as shown in Figure 10d, under the stimulation of LPS at a working concentration of 10 μg / mL, the IL-6 level was 10.16 times the basal level. Under the action of ceramide from walnut oil at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, the IL-6 factor level was significantly reduced, which were 0.84, 0.66, 0.45, and 0.25 times that of the LPS model group, respectively, in a dose-dependent manner.

[0331] As shown in Figure 11a, under the stimulation of LPS at a working concentration of 10 μg / mL, the IL-6 level was 10.16 times the basal level. Under the action of ceramide from South American Elaeagnus oil at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, the IL-6 factor level was significantly reduced, which were 0.84, 0.63, 0.40, and 0.14 times that of the LPS model group, respectively, in a dose-dependent manner; as shown in Figure 11b, under the stimulation of LPS at a working concentration of 10 μg / mL, the IL-6 level was 10.16 times the basal level. At concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, the IL-6 factor level was significantly reduced, which were 0.84, 0.63, 0.40, and 0.14 times that of the LPS model group, respectively. Under the action of borage oil ceramide at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, the IL-6 factor level was significantly reduced, which was 0.84, 0.58, 0.43, and 0.17 times that of the LPS model group, respectively, in a dose-dependent manner; as shown in Figure 11c, under the stimulation of LPS at a working concentration of 10 μg / mL, the IL-6 level was 10.16 times that of the basal level, and under the action of grape seed oil ceramide at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, IL-6 The factor levels were significantly reduced, which were 0.99, 0.79, 0.53 and 0.33 times that of the LPS model group, respectively, in a dose-dependent manner; as shown in Figure 11d, under the stimulation of LPS at a working concentration of 10 μg / mL, the IL-6 level was 10.16 times the basal level. Under the action of cactus seed oil ceramide at concentrations of 50 mg / L, 100 mg / L, 200 mg / L and 400 mg / L, the IL-6 factor levels were significantly reduced, which were 0.99, 0.74, 0.53 and 0.27 times that of the LPS model group, respectively, in a dose-dependent manner.

[0332] Therefore, the vegetable oil ceramide of the present invention has a good anti-inflammatory effect and can promote the repair of skin damaged by inflammation.

[0333] Example 41

[0334] MMP1, also known as interstitial collagenase or matrix metalloproteinase, belongs to the matrix metalloproteinase family. Its primary substrate is fibrillar collagen, degrading collagen fibers and gelatin within the extracellular matrix and altering the cellular microenvironment. MMP1 plays a crucial role in elastin production. Inhibiting MMP1 can enhance collagen and elastin synthesis in fibroblasts, while reducing MMP activity can increase the rate of collagen synthesis.

[0335] HaCaT cells were cultured at a rate of 1 × 10 5Cells were seeded at a density of 100 μL / well in a 96-well plate and incubated overnight in an incubator. After 24 hours, the supernatant was discarded and 100 μL of culture medium containing samples of different concentrations was added. No sample was added to the model group, and the negative control group was DMEM culture medium without sample. Each group had 3 replicates. After incubation for 2 hours in an environment of 5% CO2 and 37°C, UVA or UVB ultraviolet rays were irradiated. The distance between the ultraviolet radiation source and the cells was 15 cm, and the UVA intensity was 200 mJ / cm 2 , irradiation time is 2h, UVB intensity is 50mJ / cm 2 The irradiation time was 1 hour. After irradiation, the cells were incubated in the incubator for another 12 hours. Intracellular MMP-1 gene expression was measured using an MMP-1 ELISA kit. Inhibition rate = 1 - (MMP1 expression in the experimental group / MMP1 expression in the model group) × 100%.

[0336] As shown in Figure 12, for UVA, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 1.90. When the concentrations of silymarin oil ceramide (Figure 12a) were 125, 250, and 400 mg / L, the inhibition rates of MMP1 expression relative to the model group were 34%, 51%, and 69%; for UVB, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 2.33. When the concentrations of silymarin oil ceramide (Figure 12b) were 125, 250, and 400 mg / L, the inhibition rates of MMP1 expression relative to the model group were 44%, 52%, and 65%. For UVA, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 1.90. When the concentrations of linseed oil ceramide were 125, 250, and 400 mg / L (Figure 12c), the inhibition rates of MMP1 expression relative to the model group were 39%, 47%, and 64%; for UVB, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 2.33. When the concentrations of linseed oil ceramide were 125, 250, and 400 mg / L (Figure 12d), the inhibition rates of MMP1 expression relative to the model group were 38%, 48%, and 67%.

[0337] As shown in Figure 13, for UVA, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 1.90. When the concentrations of peony seed oil ceramide (Figure 13a) were 125, 250, and 400 mg / L, the inhibition rates of MMP1 expression relative to the model group were 35%, 49%, and 67%; for UVB, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 2.33. When the concentrations of peony seed oil ceramide (Figure 13b) were 125, 250, and 400 mg / L, the inhibition rates of MMP1 expression relative to the model group were 40%, 51%, and 63%. For UVA, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 1.90. When the tomato seed oil ceramide was at a concentration of 125, 250, and 400 mg / L (Figure 13c), the inhibition rates of MMP1 expression relative to the model group were 42%, 62%, and 81%; for UVB, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 2.33. When the tomato seed oil ceramide was at a concentration of 125, 250, and 400 mg / L (Figure 13d), the inhibition rates of MMP1 expression relative to the model group were 39%, 49%, and 69%.

[0338] As shown in Figure 14, for UVA, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 1.90. When the concentrations of Acer truncatum seed oil ceramide (Figure 14a) were 125, 250, and 400 mg / L, the inhibition rates of MMP1 expression relative to the model group were 35%, 50%, and 62%; for UVB, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 2.33. When the concentrations of Acer truncatum seed oil ceramide (Figure 14b) were 125, 250, and 400 mg / L, the inhibition rates of MMP1 expression relative to the model group were 30%, 53%, and 67%. For UVA, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 1.90. When the concentrations of coconut oil ceramide were 125, 250, and 400 mg / L (Figure 14c), the inhibition rates of MMP1 expression relative to the model group were 31%, 49%, and 67%; for UVB, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 2.33. When the concentrations of coconut oil ceramide were 125, 250, and 400 mg / L (Figure 14d), the inhibition rates of MMP1 expression relative to the model group were 38%, 58%, and 74%.

[0339] As shown in Figure 15, for UVA, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 1.90. When the concentrations of cottonseed oil (Figure 15a) were 125, 250, and 400 mg / L, the inhibition rates of MMP1 expression relative to the model group were 27%, 48%, and 62%; for UVB, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 2.33. When the concentrations of cottonseed oil (Figure 15b) were 125, 250, and 400 mg / L, the inhibition rates of MMP1 expression relative to the model group were 35%, 49%, and 56%. For UVA, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 1.90. When the concentrations of sea buckthorn oil ceramide were 125, 250, and 400 mg / L (Figure 15c), the inhibition rates of MMP1 expression relative to the model group were 31%, 46%, and 56%. For UVB, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 2.33. When the concentrations of sea buckthorn oil ceramide were 125, 250, and 400 mg / L (Figure 15d), the inhibition rates of MMP1 expression relative to the model group were 35%, 51%, and 69%.

[0340] As shown in Figure 16, for UVA, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 1.90. At the concentrations of 125, 250, and 400 mg / L, the inhibition rates of MMP1 expression in the model group (Figure 16a) were 34%, 44%, and 56% respectively. For UVB, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 2.33. At the concentrations of 125, 250, and 400 mg / L, the inhibition rates of MMP1 expression in the model group (Figure 16b) were 40%, 52%, and 67% respectively. For UVA, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 1.90. When the concentrations of wheat germ oil ceramide were 125, 250, and 400 mg / L (Figure 16c), the inhibition rates of MMP1 expression relative to the model group were 38%, 61%, and 67%; for UVB, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 2.33. When the concentrations of wheat germ oil ceramide were 125, 250, and 400 mg / L (Figure 16d), the inhibition rates of MMP1 expression relative to the model group were 43%, 48%, and 68%.

[0341] As shown in Figure 17, for UVA, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 1.90. When the concentrations of European plum seed oil ceramide (Figure 17a) were 125, 250, and 400 mg / L, the inhibition rates of MMP1 expression relative to the model group were 38%, 51%, and 67%; for UVB, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 2.33. When the concentrations of European plum seed oil ceramide (Figure 17b) were 125, 250, and 400 mg / L, the inhibition rates of MMP1 expression relative to the model group were 43%, 48%, and 68%. For UVA, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 1.90. When the concentrations of hazelnut oil ceramide were 125, 250, and 400 mg / L (Figure 17c), the inhibition rates of MMP1 expression relative to the model group were 29%, 44%, and 62%; for UVB, the MMP1 expression level of the negative control group was set to 1, and the expression level of the model group was 2.33. When the concentrations of hazelnut oil ceramide were 125, 250, and 400 mg / L (Figure 17d), the inhibition rates of MMP1 expression relative to the model group were 35%, 50%, and 68%.

[0342] After UVA exposure, keratinocytes promote the increased expression of MMP1 in fibroblasts, which in turn causes degradation of the skin's extracellular matrix and collagen, leading to photoaging. These results suggest that plant oil ceramides can inhibit UV-induced MMP1 production in fibroblasts, potentially playing a role in preventing photoaging.

[0343] Example 42

[0344] DPPH free radical scavenging assay for antioxidant activity

[0345] DPPH is 1,1-diphenyl-2-trinitrophenylhydrazine, which can be used in antioxidant experiments.

[0346] Samples of corresponding concentrations (50, 100, 200, 400, and 800 mg / L) were mixed with 0.1 mol / L DPPH and anhydrous ethanol solutions at a 1:1 volume ratio. DPPH and anhydrous ethanol were then mixed in equal volumes at a 1:1 ratio. The mixture was allowed to react at room temperature in the dark for 30 minutes, and the absorbance was measured at 517 nm. The absorbance of the sample-DPPH reaction solution was designated as A1, the absorbance of the sample-anhydrous ethanol reaction solution as A2, and the absorbance of the DPPH-anhydrous ethanol reaction solution as A3. The DPPH scavenging efficiency of the sample = [1-(A1-A2) / A3] × 100%.

[0347] As shown in Figure 18a, the DPPH free radical scavenging rates of tea oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 9.43%, 23.91%, 38.53%, 41.93%, and 55.99%, respectively. The antioxidant effect of ceramide 3B (i.e., oleic acid ceramide) was tested using the same method. The results are shown in Figure 18b. The DPPH free radical scavenging rates at concentrations of 50, 100, 200, 400, and 800 mg / L were 7.76%, 12.82%, 24.10%, 29. 18c, the DPPH radical scavenging rates of tomato seed oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 9.43%, 23.91%, 35.10%, 41.93%, and 50.27%, respectively; as shown in Figure 18d, the DPPH radical scavenging rates of argan oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 12.09%, 23.91%, 35.82%, 45.82%, and 52.24%, respectively.

[0348] As shown in Figure 19a, the DPPH radical scavenging rates of cottonseed oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 9.43%, 23.91%, 33.61%, 41.93%, and 49.19%, respectively; as shown in Figure 19b, the DPPH radical scavenging rates of olive oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 29.42%, 39.49%, 46.77%, 55.26%, and 67.01%, respectively; As shown in Figure 19c, the DPPH radical scavenging rates of argan oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 15.43%, 23.91%, 35.85%, 41.93%, and 47.56%, respectively; as shown in Figure 19d, the DPPH radical scavenging rates of cactus seed oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 13.43%, 24.32%, 35.10%, 39.00%, and 45.57%, respectively.

[0349] As shown in Figure 20a, the DPPH radical scavenging rates of sea buckthorn oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 26.76%, 34.38%, 40.77%, 51.72%, and 54.44%, respectively; as shown in Figure 20b, the DPPH radical scavenging rates of watermelon seed oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 24.09%, 32.67%, 39.00%, 44.60%, and 48.13%, respectively; As shown in Figure 20c, the DPPH radical scavenging rates of evening primrose oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 29.43%, 39.49%, 41.93%, 51.93%, and 66.83%, respectively; as shown in Figure 20d, the DPPH radical scavenging rates of coconut oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 29.09%, 32.72%, 35.10%, 41.93%, and 49.67%, respectively.

[0350] As shown in Figure 21a, the DPPH radical scavenging rates of soybean oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 13.43%, 27.91%, 35.24%, 38.26%, and 43.50%, respectively; as shown in Figure 21b, the DPPH radical scavenging rates of sunflower oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 9.43%, 23.91%, 35.82%, 42.16%, and 52.24%, respectively; As shown in Figure 21c, the DPPH radical scavenging rates of DHA algae oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 17.76%, 24.91%, 36.20%, 41.93%, and 46.14%, respectively; as shown in Figure 21d, the DPPH radical scavenging rates of pumpkin seed oil ceramide at concentrations of 50, 100, 200, 400, and 800 mg / L were 15.76%, 23.91%, 34.09%, 36.77%, and 46.48%, respectively.

[0351] Therefore, the scavenging rate of the vegetable oil ceramide of the present invention on DPPH is higher than that of ceramide 3B, and it has a better antioxidant effect.

[0352] Example 43

[0353] Whitening activity test

[0354] B16 cells in the exponential growth phase were obtained and digested with 0.25% trypsin-EDTA and pipetted evenly. The cells were plated at 3×10 5The cells were seeded in a 12-well plate at a density of 100 / well. The cells were cultured overnight at 37°C and 5% CO2. The supernatant was discarded and culture medium containing samples of different mass concentrations was added. The blank group was incubated with RPMI-1640 medium without sample and the model group was incubated with DMEM medium. Each group had 3 replicates and was incubated for 24 hours in an environment of 5% CO2 and 37°C. The culture medium in the well plate was discarded and washed once or twice with phosphate buffered saline (PBS). Then, 1 mL of NaOH solution (1 mol / L) containing 10% DMSO was added to lyse the cells. The cells were kept at 80°C or 100°C for 2 hours until the cells were completely dissolved. The plate was placed in a microplate reader and the absorbance was measured at 405 nm. The melanin inhibition rate was calculated as 1-(OD value of each well / OD value of the model group) × 100%.

[0355] As shown in Figure 22a, the melanin content of the blank control group was set to 1, and the melanin expression of the modeling group was 1.54. At concentrations of 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of evening primrose oil ceramide were 20.08%, 21.12%, 24.33%, 33.03%, and 42.26%, respectively; as shown in Figure 22b, the melanin content of the blank control group was set to 1, and the melanin expression of the modeling group was 1.51. At concentrations of 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of shea butter ceramide were 8.14%, 14.73%, 22.21%, 27.79%, and 38.33%, respectively; As shown in Figure 22c, the melanin content of the blank control group was set to 1, and the melanin expression of the modeling group was 1.54. At concentrations of 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of silymarin oil ceramide were 22.24%, 23.28%, 26.49%, 37.36%, and 44.85%, respectively; as shown in Figure 22d, the melanin content of the blank control group was set to 1, and the melanin expression of the modeling group was 1.51. At concentrations of 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of peony seed oil ceramide were 9.91%, 16.94%, 22.21%, 27.79%, and 40.54%, respectively.

[0356] As shown in Figure 23a, the melanin content of the blank control group was set to 1, and the melanin expression of the modeling group was 1.54. At concentrations of 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of tomato seed oil ceramide were 13.59%, 21.12%, 28.66%, 38.66%, and 40.53%, respectively; as shown in Figure 23b, the melanin content of the blank control group was set to 1, and the melanin expression of the modeling group was 1.54. At concentrations of 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of Acer truncatum seed oil ceramide were 22.24%, 34.10%, 39.48%, 46.02%, and 51.35%, respectively; As shown in Figure 23c, the melanin content of the blank control group was set to 1, and the melanin expression of the modeling group was 1.51. When the concentrations were 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of ceramide from South American oil vine oil were 16.54%, 25.79%, 28.85%, 34.43%, and 42.75%, respectively; as shown in Figure 23d, the melanin content of the blank control group was set to 1, and the melanin expression of the modeling group was 1.51. When the concentrations were 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of ceramide from rosehip oil were 11.68%, 19.15%, 25.53%, 27.79%, and 40.54%, respectively.

[0357] As shown in Figure 24a, the melanin content of the blank control group was set to 1, and the melanin expression of the modeling group was 1.51. At the concentrations of 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of grape seed oil ceramide were 17.43%, 19.15%, 26.64%, 32.22%, and 44.96%, respectively; as shown in Figure 24b, the melanin content of the blank control group was set to 1, and the melanin expression of the modeling group was 1.54. At the concentrations of 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of sea buckthorn oil ceramide were 15.10%, 21.55%, 24.98%, 35.20%, and 46.59%, respectively; As shown in Figure 24c, the melanin content of the blank control group was set to 1, and the melanin expression of the modeling group was 1.54. When the concentrations were 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of argan oil ceramide were 17.91%, 18.95%, 22.16%, 30.87%, and 39.66%, respectively; as shown in Figure 24d, the melanin content of the blank control group was set to 1, and the melanin expression of the modeling group was 1.54. When the concentrations were 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of marula oil ceramide were 15.53%, 22.42%, 30.82%, 40.39%, and 47.02%, respectively.

[0358] Therefore, the vegetable oil ceramide of the present invention exhibits a good whitening effect.

[0359] The above description is merely a specific embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any changes or substitutions that can be easily conceived by a person skilled in the art within the technical scope disclosed in the present invention should be included in the scope of protection of the present invention. Therefore, the scope of protection of the present invention should be based on the scope of protection of the claims.

Claims

1. Vegetable oil ceramide, which is obtained by reacting vegetable oil fatty acids with sphingosine compounds, wherein the vegetable oil fatty acids are selected from olive oil fatty acids, tea oil fatty acids, sea buckthorn oil fatty acids, grape seed oil fatty acids, nut oil fatty acids, borage oil fatty acids, rosehip oil fatty acids, soybean oil fatty acids, rice bran oil fatty acids, cottonseed oil fatty acids, South American tung oil fatty acids, watermelon seed oil fatty acids, coconut oil fatty acids, maple seed oil fatty acids, walnut oil fatty acids, avocado oil fatty acids, tomato seed oil fatty acids, sea sandalwood seed oil fatty acids, utilis utilis oil fatty acids, safflower seed oil fatty acids, peony seed oil fatty acids, and sunflower seed oil fatty acids. , perilla seed oil fatty acid, linseed oil fatty acid, milk thistle oil fatty acid, shea butter fatty acid, evening primrose oil fatty acid, argan oil fatty acid, hemp seed oil fatty acid, white meadowfoam seed oil fatty acid, baobab seed oil fatty acid, cactus seed oil fatty acid, wheat germ oil fatty acid, sesame oil fatty acid, corn oil fatty acid, almond oil fatty acid, garlic fruit oil fatty acid, peanut oil fatty acid, black currant seed oil fatty acid, rapeseed oil fatty acid, hazelnut oil fatty acid, pumpkin seed oil fatty acid, DHA algae oil fatty acid, crabapple oil fatty acid, kiwi seed oil fatty acid, marula oil fatty acid, and European plum seed oil fatty acid.

2. The vegetable oil ceramide according to claim 1, characterized in that The sphingosine compound is selected from at least one of sphingosine, phytosphingosine, and dihydrosphingosine.

3. The vegetable oil ceramide according to claim 1, characterized in that The vegetable oil fatty acid is obtained by hydrolyzing the vegetable oil.

4. The vegetable oil ceramide according to claim 1, characterized in that The olive oil fatty acid composition is: 20-83wt% oleic acid, 7.5-20wt% palmitic acid, 3.5-70wt% linoleic acid, 0.5-5wt% stearic acid, 0.1-1.0wt% linolenic acid, 0-3.5wt% palmitoleic acid, 0-0.6wt% arachidic acid, 0-0.4wt% eicosenoic acid, 0-0.3wt% heptadecanoic acid, 0-0.3wt% heptadecanoic acid, 0-0.2wt% behenic acid, 0-0.2wt% lignoceric acid, 0-0.05wt% myristic acid; the tea oil fatty acid composition is: 75-90wt% oleic acid, 2-15wt% % linoleic acid, 1-10wt% palmitic acid, 0.1-3wt% stearic acid, 0.01-1wt% linolenic acid, 0-0.5wt% arachidic acid; the composition of the sea buckthorn oil fatty acid is: 20-35wt% oleic acid, 8-30wt% palmitic acid, 4-40wt% linoleic acid, 2-30wt% linolenic acid, 0.5-35wt% palmitoyl oleate, 0.5-3wt% stearic acid, 0-1wt% myristic acid; the composition of the grape seed oil fatty acid is: 55-85wt% linoleic acid, 8-25wt% oleic acid, 1-12wt% palmitic acid, 0.5-7wt% stearic acid, 0.01- 2wt% palmitic acid, 0.01-1wt% linolenic acid, 0-1wt% arachidic acid; the composition of the nut oil fatty acid is: 55-80wt% oleic acid, 12-35wt% palmitic acid, 2-10wt% palmitic acid, 0.4-3wt% linoleic acid, 0.1-3wt% arachidic acid, 0.2-5wt% stearic acid, 0.01-1wt% linolenic acid, 0.01-1wt% behenic acid, 0-1.5wt% myristic acid, 0-3wt% arachidic acid; the composition of the borage oil fatty acid is: 20-40wt% γ-linolenic acid, 30-45wt% linoleic acid, 15- 25wt% oleic acid, 2-8wt% palmitic acid, 1-5wt% stearic acid, 0-2wt% arachidic acid, 0-2wt% arachidic acid, 0-2wt% erucic acid; the composition of the rosehip oil fatty acid is: 30-60wt% linoleic acid, 20-45wt% linolenic acid, 6-25wt% oleic acid, 0.1-3wt% stearic acid, 0.5-5wt% palmitic acid, 0.01-1wt% arachidic acid, 0-1wt% arachidic acid; the composition of the soybean oil fatty acid is: 50-75wt% linoleic acid, 15-30wt% oleic acid, 2-12wt% palmitic acid, 1-10wt% linolenic acid, 1-5wt% stearic acid, 0-2wt% arachidic acid, 0-2wt% behenic acid; the composition of the rice bran oil fatty acid is: 40-60wt% oleic acid, 20-45wt% linoleic acid, 5-20wt% palmitic acid, 0.5-5wt% stearic acid, 0.1-2wt% linolenic acid, 0-2wt% arachidic acid; the composition of the cottonseed oil fatty acid is: 55-80wt% linoleic acid, 10-25wt% palmitic acid, 6-18wt% oleic acid, 1-3wt% stearic acid, 0.1-1wt% arachidic acid, 0.02-1wt% palmitoleic acid, 0.01-1wt% linolenic acid; the composition of the South American elm oil fatty acid is: 45-68wt% linolenic acid, 20-40wt% linoleic acid, 5-12wt% oleic acid, 2-5wt% palmitic acid, 1-4wt% stearic acid; the composition of the watermelon seed oil fatty acid is: 60-80wt% linoleic acid, 3-15wt% palmitic acid, 10-30wt% oleic acid, 1-5wt% stearic acid; the coconut oil fatty acid The composition of the acid is: 20-70wt% lauric acid, 10-50wt% myristic acid, 10-20wt% palmitic acid, 2-10wt% stearic acid, 2-10wt% oleic acid, 0-3wt% capric acid, 0-3wt% caproic acid; the composition of the fatty acid of the maple seed oil is: 25-48wt% linoleic acid, 20-40wt% oleic acid, 5-30wt% arachidic acid, 4-15wt% arachidic acid, 0.5-5wt% linolenic acid, 0.1-5wt% palmitic acid, 0.1-4wt% stearic acid; the composition of the fatty acid of the walnut oil is: 40-75wt% linoleic acid, 15-50wt% oleic acid, 2-10wt% palmitic acid, 0-5wt% linolenic acid, 0-4wt% stearic acid; the crocodile The composition of the pear oil fatty acid is: 50-80wt% oleic acid, 5-25wt% palmitic acid, 5-20wt% linoleic acid, 6-18wt% palmitic acid, 0.1-2wt% stearic acid, 0.1-1wt% linolenic acid, 0-1wt% arachidic acid, and 0-0.5wt% arachidic acid; the composition of the tomato seed oil fatty acid is: 55-80wt% linoleic acid, 10-25wt% oleic acid, 3-20wt% palmitic acid, 1-8wt% stearic acid, 0.2-2wt% linolenic acid, and 0-1wt% arachidic acid; the composition of the sea sandalwood seed oil fatty acid is: 50-75wt% oleic acid, 15-40wt% linolenic acid, 0.5-10wt% stearic acid, 0-15wt% ximenynic acid, 0-1 5wt% nervonic acid, 0-2wt% behenic acid, 0-1wt% palmitic acid, 0-1wt% linoleic acid; the composition of the utilitarian fruit oil fatty acid is: 30-50wt% linoleic acid, 25-40wt% oleic acid, 10-25wt% palmitic acid, 3-10wt% stearic acid, 0-1wt% palmitoleic acid, 0-1wt% arachidic acid; the composition of the safflower seed oil fatty acid is: 70-90wt% linoleic acid, 4-20wt% oleic acid, 1-8wt% palmitic acid, 0.01-2wt% linolenic acid, 0-2wt% stearic acid, 0-1wt% arachidic acid; the composition of the peony seed oil fatty acid is: 35-70wt% α-linolenic acid, 15-40wt% linoleic acid, 10-30wt% oleic acid, 0.1-5wt% palmitic acid, 0.1-5wt% stearic acid, 0-1wt% arachidic acid; the composition of the sunflower oil fatty acid is: 55-75wt% linoleic acid, 20-40wt% oleic acid, 0.5-7wt% stearic acid, 1-8wt% palmitic acid, 0-2wt% behenic acid, 0-1wt% arachidic acid; the composition of the perilla seed oil fatty acid is: 65-90wt% α-linolenic acid, 4-30wt% linoleic acid, 4-20wt% oleic acid, 1-4wt% stearic acid, 0-3.5wt% palmitic acid, 0-0.6wt% arachidic acid; the composition of the linseed oil fatty acid is: 40-70wt% linolenic acid, 10-25wt% linoleic acid, 10-2 5wt% oleic acid, 1-8wt% palmitic acid, 1-8wt% stearic acid, 0-1wt% arachidic acid; the composition of the milk thistle oil fatty acid is: 50-75wt% linoleic acid, 15-45wt% oleic acid, 1-10wt% palmitic acid, 1-6wt% stearic acid, 0.2-4wt% arachidic acid, 0.5-4wt% behenic acid, 0.01-2.5wt% linolenic acid, 0-1.5wt% myristic acid; the composition of the shea butter fatty acid is: 35-60wt% oleic acid, 25-55wt% stearic acid, 2-10wt% linoleic acid, 0.5-10wt% palmitic acid, 0.1-2wt% arachidic acid, 0-1wt% linolenic acid, 0-1wt% behenic acid Acid; the composition of the evening primrose oil fatty acid is: 55-88wt% linoleic acid, 3-20wt% oleic acid, 5-20wt% γ-linolenic acid, 0.5-5wt% palmitic acid, 0-2wt% stearic acid, 0-2wt% arachidic acid, 0-1wt% behenic acid; the composition of the argan oil fatty acid is: 35-50wt% oleic acid, 30-50wt% linoleic acid, 5-15wt% palmitic acid, 2-8wt% stearic acid, 0.1-1wt% arachidic acid, 0.01-0.5wt% linolenic acid, 0-0.5wt% behenic acid, 0-0.5wt% arachidic acid; the composition of the hemp seed oil fatty acid is: 50-75wt% linoleic acid, 5-30wt% Linolenic acid, 5-20wt% oleic acid, 3-15wt% palmitic acid, 1-5wt% stearic acid; the fatty acid composition of the white meadowfoam seed oil is: 50-80wt% cis-5-eicosenoic acid, 8-25wt% cis-5,13-docosadienoic acid, 5-20wt% erucic acid, 1-10wt% cis-5-docosadienoic acid, 0-1wt% oleic acid, 0-1wt% linoleic acid; the fatty acid composition of the baobab seed oil is: 30-50wt% oleic acid, 15-35wt% linoleic acid, 13-30wt% palmitic acid, 2-8wt% stearic acid, 0.5-5wt% linolenic acid, 0.2-2wt% arachidic acid, 0-1wt% palmitoleic acid, 0-0.5wt% myristic acid; the composition of the cactus seed oil fatty acid is: 50-75wt% linolenic acid, 10-30wt% oleic acid, 5-15wt% palmitic acid, 3-10wt% palmitic acid, 3-8wt% stearic acid, 0.1-1wt% arachidic acid; the composition of the wheat germ oil fatty acid is: 50-75wt% linoleic acid, 15-45wt% oleic acid, 2-10wt% palmitic acid, 1-8wt% linolenic acid, 0.1-1wt% arachidic acid, 0-0.5wt% stearic acid, 0-0.5wt% arachidic acid; the composition of the sesame oil fatty acid is: 45-70wt% linoleic acid, 15-35wt% oleic acid, 6-20wt% palmitic acid, 0-2wt% stearic acid, 0-1w t% arachidic acid, 0-0.5wt% linolenic acid; the composition of the corn oil fatty acid is: 50-70wt% linoleic acid, 20-35wt% oleic acid, 5-18wt% palmitic acid, 0.5-3wt% stearic acid, 0.01-1wt% linolenic acid, 0-1wt% arachidic acid; the composition of the almond oil fatty acid is: 55-80wt% oleic acid, 15-35wt% linoleic acid, 0.1-8wt% palmitic acid, 0.5-2wt% stearic acid, 0.01-1wt% linolenic acid; the composition of the garlic fruit oil fatty acid is: 40-60wt% nervonic acid, 30-50wt% oleic acid, 5-12wt% arachidic acid, 0-2wt% palmitic acid, 0-2wt% linoleic acid; the peanut oil fatty acid is: The composition is: 40-60wt% linoleic acid, 30-50wt% oleic acid, 4-12wt% palmitic acid, 0.5-5wt% stearic acid, 0-1wt% arachidic acid, 0-1wt% behenic acid; the composition of the blackcurrant seed oil fatty acid is: 40-60wt% linoleic acid, 20-40wt% linolenic acid, 10-20wt% oleic acid, 1-8wt% palmitic acid, 0-2wt% stearic acid, 0-2wt% arachidic acid; the composition of the rapeseed oil fatty acid is: 50-80wt% oleic acid, 10-30wt% linoleic acid, 2-8wt% linolenic acid, 1-5wt% stearic acid, 0.5-5wt% palmitic acid, 0-1wt% arachidic acid, 0-1wt% arachidic acid, 0-1wt% erucic acid; The fatty acid composition of the hazelnut oil is: 70-90 wt% oleic acid, 8-25 wt% linoleic acid, 0.5-5 wt% palmitic acid, 0.5-4 wt% stearic acid, 0-0.5 wt% linolenic acid, 0-0.5 wt% palmitoleic acid; the fatty acid composition of the pumpkin seed oil is: 40-70 wt% linoleic acid, 20-55 wt% oleic acid, 3-10 wt% palmitic acid, 1-5 wt% stearic acid, 0.1-5 wt% linolenic acid, 0-1 wt% arachidic acid, 0-0.5 wt% palmitoleic acid; the fatty acid composition of the DHA algae oil is: 50-75 wt% DHA, 15-35 wt% oleic acid, 3-15 wt% palmitic acid, 0.1-1 wt% stearic acid, 0.1-1 wt% EPA, 0.The composition of the crabapple oil fatty acid is: 30-50wt% oleic acid, 15-40wt% linoleic acid, 8-20wt% stearic acid, 6-20wt% palmitic acid, 0.2-1.5wt% arachidic acid, 0.05-2wt% linolenic acid, 0.05-1wt% palmitoleic acid, 0-1wt% behenic acid, 0-0.5wt% arachidic acid; the composition of the kiwifruit seed oil fatty acid is: 45-70wt% linolenic acid, 8-20wt% linoleic acid, 5-20wt% stearic acid, 0.2-1.5wt% arachidic acid, 0.05-2wt% linolenic acid, 0.05-1wt% palmitoleic acid, 0-1wt% behenic acid, 0-0.5wt% arachidic acid; the composition of the kiwifruit seed oil fatty acid is: 45-70wt% linolenic acid, 8-20wt% linoleic acid, 5-20wt% stearic acid, 0.2-1.5wt% t% oleic acid, 2-10wt% palmitic acid, 0.5-5wt% stearic acid; the composition of the marula oil fatty acid is: 65-85wt% oleic acid, 5-15wt% palmitic acid, 2-10wt% linoleic acid, 2-10wt% stearic acid, 0.2-2wt% arachidic acid, 0-1wt% arachidonic acid, 0-0.5wt% linolenic acid; the composition of the European plum seed oil fatty acid is: 60-80wt% oleic acid, 10-30wt% linoleic acid, 0.5-5wt% stearic acid, 0.5-3wt% palmitoleic acid, 0-7wt% palmitic acid, 0-1wt% linolenic acid.

5. Vegetable oil ceramides, selected from at least two of oleic ceramide, linoleic ceramide, palmitic ceramide, linolenic ceramide, stearic ceramide, palmitoleic ceramide, arachidic ceramide, arachidonoyl ceramide, behenic ceramide, erucic ceramide, myristic ceramide, ceramide ceramide, lauric ceramide, eicosenoic ceramide, heptadecanoic ceramide, heptadecanoyl ceramide, tetracosenoic ceramide, DHA ceramide, EPA ceramide, decanoic ceramide, hexanoic ceramide, ximenynic ceramide, cis-5-eicosenoic ceramide, cis-5,13-docosadienoic ceramide, and cis-5-docosadienoic ceramide.

6. The vegetable oil ceramide according to claim 5, which is selected from the group consisting of no more than 90 wt% oleic acid ceramide, no more than 90 wt% linoleic acid ceramide, no more than 30 wt% palmitic acid ceramide, no more than 90 wt% linolenic acid ceramide, no more than 55 wt% stearic acid ceramide, no more than 35 wt% palmitoleic acid ceramide, no more than 30 wt% arachidic acid ceramide, no more than 15 wt% oleic acid ceramide, no more than 4 wt% behenic acid ceramide, no more than 20 wt% erucic acid ceramide, no more than 50 wt% myristic acid ceramide, no more than 60 wt% ceramide, no more than 70 wt% lauric acid ceramide, no more than 10 wt% ceramide, no more than 15 wt% ceramide, no more than 4 wt% behenic acid ceramide, no more than 20 wt% ceramide, no more than 50 wt% myristic acid ceramide, no more than 60 wt% ceramide, no more than 70 wt% ceramide, no more than 10 wt% ceramide, no more than 15 wt% ceramide, no more than 10 ... At least two of more than 0.4 wt% eicosenoic acid ceramide, no more than 0.3 wt% heptadecanoic acid ceramide, no more than 0.3 wt% heptadecanoic acid ceramide, no more than 0.2 wt% tetracosanoic acid ceramide, no more than 75 wt% DHA ceramide, no more than 1 wt% EPA ceramide, no more than 3 wt% decanoic acid ceramide, no more than 3 wt% hexanoic acid ceramide, no more than 15 wt% ximenynic acid ceramide, no more than 80 wt% cis-5-eicosenoic acid ceramide, no more than 25 wt% cis-5,13-docosadienoic acid ceramide, and no more than 10 wt% cis-5-docosaenoic acid ceramide.

7. The method for synthesizing the vegetable oil ceramide according to any one of claims 1 to 6, comprising the following steps: The vegetable oil fatty acid reacts with the sphingosine compound under the conditions of a condensing agent and an organic base, wherein the condensing agent is DCC or EDCI, and the organic base is DMAP, DIPEA, NMM or Et3N; The molar ratio of the vegetable oil fatty acid, sphingosine compound, condensing agent and organic base is 1:(1-1.5):(1-2):(0.2-2), and the solvent of the reaction is at least one of dichloromethane, tetrahydrofuran, ethyl acetate and acetonitrile.

8. Use of the vegetable oil ceramide according to any one of claims 1 to 6 in cosmetics, medicines, dietary products or health products.

9. The use according to claim 8, characterized in that The vegetable oil ceramide has at least one of the following effects: skin barrier repair, tissue healing, anti-aging, anti-inflammatory, anti-photoaging, anti-oxidation, promotion of collagen synthesis, maintenance of elastin activity, and whitening.

10. A composition comprising the plant oil ceramide according to any one of claims 1 to 6, wherein the composition has at least one of the following effects: skin barrier repair, tissue healing, anti-aging, anti-inflammatory, anti-photoaging, antioxidant, promotion of collagen synthesis, maintenance of elastin activity, and whitening.

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