Vegetable oil ceramide and its synthesis method and use

Abstract

The present invention belongs to the field of biopharmaceuticals and discloses a vegetable oil ceramide obtained by reacting a vegetable oil fatty acid with a sphingosine-based compound. The sphingosine-based compound is selected from sphingosine, phytosphingosine, and dihydrosphingosine. The vegetable oil fatty acid is 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, and rice bran oil fatty acids. The present invention also discloses a method for synthesizing and using vegetable oil ceramide. Vegetable oil ceramide exhibits excellent properties in repairing the skin's natural barrier, anti-inflammation, tissue healing, and anti-aging, and has broad potential for application in fields such as cosmetics, health care products, and biopharmaceuticals.

Description

[Technical Field]

[0001] The present invention relates to the technical field of biopharmaceuticals, and specifically to vegetable oil ceramides and their synthesis methods and uses. [Background technology]

[0002] Ceramides (also known as molecular nails) are naturally present in the skin and are an essential component of the skin barrier (stratum corneum), with a high content of 40-50 wt%. Ceramides are a type of sphingolipid composed of a long-chain sphingosine base and a fatty acid. The carbon chain length, degree of unsaturation, and number of hydroxyl groups in the sphingosine and fatty acid moieties can all be varied, and ceramides represent a group of compounds. Ceramides exhibit excellent properties in terms of regulating skin barrier function, restoring skin moisture, and strengthening adhesion between keratinocytes.

[0003] Due to the importance of ceramides, many cosmetic and pharmaceutical companies are researching and developing related products. Natural plant-derived ceramides are a more sustainable and environmentally friendly source of raw materials, and because they have properties similar to those of the ceramide components in the skin, they can form an effective skin barrier to prevent moisture loss and resist external damage, making them the next generation of environmentally friendly, safe, and reliable ceramide products.

[0004] Vegetable oils are made from the fruits, seeds, germs, etc. of oil-rich plants. They are pretreated by washing, removing impurities, dehulling, crushing, softening, rolling, extrusion swelling, etc., and then extracted by mechanical pressing or solvent leaching to obtain crude oil, which is then further refined. The fatty acids in vegetable oils can moisturize and brighten the skin. Different vegetable oils have different fatty acid contents and types, and often contain other physiologically active substances. Summary of the Invention

[0005] An object of the present invention is to provide ceramides synthesized using vegetable oil fatty acids.

[0006] Another object of the present invention is to provide a method for synthesizing vegetable oil ceramide using vegetable oils or vegetable oil fatty acids derived from natural plants as raw materials.

[0007] Another object of the present invention is to provide uses of vegetable oil ceramides.

[0008] In order to achieve one of the above objectives, the present invention adopts the following technical solutions. JPEG2025536776000002.jpg53170JPEG2025536776000003.jpg106170

[0009] The reaction may be a chemical synthesis reaction (as described in detail below), or may be a microbial fermentation method, i.e., using Pichia yeast or Saccharomyces cerevisiae to ferment under a certain environment to obtain a sphingosine compound, and then adding a fatty acid to finally obtain ceramide; or alternatively, vegetable oil ceramide may be obtained by selecting an appropriate strain and fermenting it using vegetable oil as a raw material.

[0010] 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.

[0011] Furthermore, the vegetable oil fatty acids are obtained by hydrolysis of vegetable oils, for example, tea oil fatty acids are obtained by hydrolysis of tea oil, and sea buckthorn oil fatty acids are obtained by hydrolysis of sea buckthorn seed oil or sea buckthorn fruit oil.

[0012] The fatty acid composition of olive oil is 20-83 wt% oleic acid, 7.5-20 wt% palmitic acid, 3.5-70 wt% linoleic acid, 0.5-5 wt% stearic acid, 0.1-1.0 wt% linolenic acid, 0-3.5 wt% palmitoleic acid, 0-0.6 wt% arachidic acid, 0-0.4 wt% eicosenoic acid, 0-0.3 wt% heptadecanoic acid, 0-0.3 wt% heptadecenoic acid, 0-0.2 wt% behenic acid, 0-0.2 wt% lignoceric acid, and 0-0.05 wt% myristic acid.

[0013] The composition of tea oil fatty acids 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.

[0014] The composition of sea buckthorn oil fatty acids is 20-35 wt% oleic acid, 8-30 wt% palmitic acid, 4-40 wt% linoleic acid, 2-30 wt% linolenic acid, 0.5-35 wt% palmitoleic acid, 0.5-3 wt% stearic acid, and 0-1 wt% myristic acid.

[0015] The composition of grape seed oil fatty acids is 55-85 wt% linoleic acid, 8-25 wt% oleic acid, 1-12 wt% palmitic acid, 0.5-7 wt% stearic acid, 0.01-2 wt% palmitoleic acid, 0.01-1 wt% linolenic acid, and 0-1 wt% arachidic acid.

[0016] JPEG2025536776000004.jpg19170

[0017] The composition of borage oil fatty acids is 20-40 wt% gamma-linolenic acid, 30-45 wt% linoleic acid, 15-25 wt% oleic acid, 2-8 wt% palmitic acid, 1-5 wt% stearic acid, 0-2 wt% arachidic acid, 0-2 wt% cis-11-eicosenoic acid, and 0-2 wt% erucic acid.

[0018] The composition of rosehip oil fatty acids is 30-60 wt% linoleic acid, 20-45 wt% linolenic acid, 6-25 wt% oleic acid, 0.1-3 wt% stearic acid, 0.5-5 wt% palmitic acid, 0.01-1 wt% arachidic acid, and 0-1 wt% cis-11-eicosenoic acid.

[0019] 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.

[0020] The composition of rice bran oil fatty acids is 40-60 wt% oleic acid, 20-45 wt% linoleic acid, 5-20 wt% palmitic acid, 0.5-5 wt% stearic acid, 0.1-2 wt% linolenic acid, and 0-2 wt% arachidic acid.

[0021] The composition of cottonseed oil fatty acids is 55-80 wt% linoleic acid, 10-25 wt% palmitic acid, 6-18 wt% oleic acid, 1-3 wt% stearic acid, 0.1-1 wt% arachidic acid, 0.02-1 wt% palmitoleic acid, and 0.01-1 wt% linolenic acid.

[0022] The composition of Inca Inchi oil fatty acids is 45-68 wt% linolenic acid, 20-40 wt% linoleic acid, 5-12 wt% oleic acid, 2-5 wt% palmitic acid, and 1-4 wt% stearic acid.

[0023] The composition of watermelon seed oil fatty acids is 60-80 wt% linoleic acid, 3-15 wt% palmitic acid, 10-30 wt% oleic acid, and 1-5 wt% stearic acid.

[0024] The composition of coconut oil fatty acids is 20-70 wt% lauric acid, 10-50 wt% myristic acid, 10-20 wt% palmitic acid, 2-10 wt% stearic acid, 2-10 wt% oleic acid, 0-3 wt% capric acid, and 0-3 wt% caproic acid.

[0025] The fatty acid composition of Genbao Seed Oil is 25-48 wt% linoleic acid, 20-40 wt% oleic acid, 5-30 wt% arachidic acid, 4-15 wt% cis-11-eicosenoic acid, 0.5-5 wt% linolenic acid, 0.1-5 wt% palmitic acid, and 0.1-4 wt% stearic acid.

[0026] The composition of walnut oil fatty acids is 40-75 wt% linoleic acid, 15-50 wt% oleic acid, 2-10 wt% palmitic acid, 0-5 wt% linolenic acid, and 0-4 wt% stearic acid.

[0027] The fatty acid composition of avocado oil is 50-80 wt% oleic acid, 5-25 wt% palmitoleic acid, 5-20 wt% linoleic acid, 6-18 wt% palmitic acid, 0.1-2 wt% stearic acid, 0.1-1 wt% linolenic acid, 0-1 wt% arachidic acid, and 0-0.5 wt% cis-11-eicosenoic acid.

[0028] The fatty acid composition of tomato seed oil is 55-80 wt% linoleic acid, 10-25 wt% oleic acid, 3-20 wt% palmitic acid, 1-8 wt% stearic acid, 0.2-2 wt% linolenic acid, and 0-1 wt% arachidic acid.

[0029] The fatty acid composition of sea buckthorn seed oil is 50-75 wt% oleic acid, 15-40 wt% linolenic acid, 0.5-10 wt% stearic acid, 0-15 wt% ximenynic acid, 0-15 wt% nervonic acid, 0-2 wt% behenic acid, 0-1 wt% palmitic acid, and 0-1 wt% linoleic acid.

[0030] The composition of blue thorn oil fatty acids is 30-50 wt% linoleic acid, 25-40 wt% oleic acid, 10-25 wt% palmitic acid, 3-10 wt% stearic acid, 0-1 wt% palmitoleic acid, and 0-1 wt% arachidic acid.

[0031] The composition of safflower seed oil fatty acids 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.

[0032] The fatty acid composition of button seed oil is 35-70 wt% α-linolenic acid, 15-40 wt% linoleic acid, 10-30 wt% oleic acid, 0.1-5 wt% palmitic acid, 0.1-5 wt% stearic acid, and 0-1 wt% arachidic acid.

[0033] The composition of the fatty acids in sunflower seed oil is 55-75 wt% linoleic acid, 20-40 wt% oleic acid, 0.5-7 wt% stearic acid, 1-8 wt% palmitic acid, 0-2 wt% behenic acid, and 0-1 wt% arachidic acid.

[0034] The fatty acid composition of perilla seed oil is 65-90 wt% α-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% cis-11-eicosenoic acid.

[0035] The composition of linseed oil fatty acids is 40-70 wt% linolenic acid, 10-25 wt% linoleic acid, 10-25 wt% oleic acid, 1-8 wt% palmitic acid, 1-8 wt% stearic acid, and 0-1 wt% arachidic acid.

[0036] The composition of milk thistle oil fatty acids is 50-75 wt% linoleic acid, 15-45 wt% oleic acid, 1-10 wt% palmitic acid, 1-6 wt% stearic acid, 0.2-4 wt% arachidic acid, 0.5-4 wt% behenic acid, 0.01-2.5 wt% linolenic acid, and 0-1.5 wt% myristic acid.

[0037] The composition of shea butter fatty acids is 35-60 wt% oleic acid, 25-55 wt% stearic acid, 2-10 wt% linoleic acid, 0.5-10 wt% palmitic acid, 0.1-2 wt% arachidic acid, 0-1 wt% linolenic acid, and 0-1 wt% behenic acid.

[0038] The composition of evening primrose oil fatty acids is 55-88 wt% linoleic acid, 3-20 wt% oleic acid, 5-20 wt% γ-linolenic acid, 0.5-5 wt% palmitic acid, 0-2 wt% stearic acid, 0-2 wt% cis-11-eicosenoic acid, and 0-1 wt% behenic acid.

[0039] The composition of argan oil fatty acids is 35-50 wt% oleic acid, 30-50 wt% linoleic acid, 5-15 wt% palmitic acid, 2-8 wt% stearic acid, 0.1-1 wt% arachidic acid, 0.01-0.5 wt% linolenic acid, 0-0.5 wt% behenic acid, and 0-0.5 wt% cis-11-eicosenoic acid.

[0040] The fatty acid composition of hemp seed oil is 50-75 wt% linoleic acid, 5-30 wt% linolenic acid, 5-20 wt% oleic acid, 3-15 wt% palmitic acid, and 1-5 wt% stearic acid.

[0041] The fatty acid composition of meadowfoam seed oil is 50-80 wt% cis-5-eicosenoic acid, 8-25 wt% cis-5,13-docosadienoic acid, 5-20 wt% erucic acid, 1-10 wt% cis-5-docosanoic acid, 0-1 wt% oleic acid, and 0-1 wt% linoleic acid.

[0042] The fatty acid composition of baobab seed oil is 30-50 wt% oleic acid, 15-35 wt% linoleic acid, 13-30 wt% palmitic acid, 2-8 wt% stearic acid, 0.5-5 wt% linolenic acid, 0.2-2 wt% arachidic acid, 0-1 wt% palmitoleic acid, and 0-0.5 wt% myristic acid.

[0043] The fatty acid composition of prickly pear seed oil is 50-75 wt% linoleic acid, 10-30 wt% oleic acid, 5-15 wt% palmitoleic acid, 3-10 wt% palmitic acid, 3-8 wt% stearic acid, and 0.1-1 wt% arachidic acid.

[0044] The composition of wheat germ oil fatty acids is 50-75 wt% linoleic acid, 15-45 wt% oleic acid, 2-10 wt% palmitic acid, 1-8 wt% linolenic acid, 0.1-1 wt% cis-11-eicosenoic acid, 0-0.5 wt% stearic acid, and 0-0.5 wt% arachidic acid.

[0045] The composition of sesame oil fatty acids 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.

[0046] The composition of corn oil fatty acids is 50-70 wt% linoleic acid, 20-35 wt% oleic acid, 5-18 wt% palmitic acid, 0.5-3 wt% stearic acid, 0.01-1 wt% linolenic acid, and 0-1 wt% arachidic acid.

[0047] The composition of almond oil fatty acids 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.

[0048] The fatty acid composition of Malania oleifera seed oil is 40-60 wt% nervonic acid, 30-50 wt% oleic acid, 5-12 wt% arachidic acid, 0-2 wt% palmitic acid, and 0-2 wt% linoleic acid.

[0049] The composition of peanut oil fatty acids is 40-60 wt% linoleic acid, 30-50 wt% oleic acid, 4-12 wt% palmitic acid, 0.5-5 wt% stearic acid, 0-1 wt% arachidic acid, and 0-1 wt% behenic acid.

[0050] The fatty acid composition of blackcurrant seed oil is 40-60 wt% linoleic acid, 20-40 wt% linolenic acid, 10-20 wt% oleic acid, 1-8 wt% palmitic acid, 0-2 wt% stearic acid, and 0-2 wt% arachidic acid.

[0051] The composition of rapeseed oil fatty acids is 50-80 wt% oleic acid, 10-30 wt% linoleic acid, 2-8 wt% linolenic acid, 1-5 wt% stearic acid, 0.5-5 wt% palmitic acid, 0-1 wt% arachidic acid, 0-1 wt% cis-11-eicosenoic acid, and 0-1 wt% erucic acid.

[0052] The composition of hazelnut oil fatty acids 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, and 0-0.5 wt% palmitoleic acid.

[0053] The fatty acid composition of 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, and 0-0.5 wt% palmitoleic acid.

[0054] The composition of DHA algal oil fatty acids 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, 0.01-0.5 wt% linolenic acid, 0-0.5 wt% arachidic acid, and 0-0.5 wt% behenic acid.

[0055] The fatty acid composition of Calophyllum indicum seed oil is 30-50 wt% oleic acid, 15-40 wt% linoleic acid, 8-20 wt% stearic acid, 6-20 wt% palmitic acid, 0.2-1.5 wt% arachidic acid, 0.05-2 wt% linolenic acid, 0.05-1 wt% palmitoleic acid, 0-1 wt% behenic acid, and 0-0.5 wt% cis-11-eicosenoic acid.

[0056] The fatty acid composition of kiwi 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.

[0057] The fatty acid composition of marula oil is 65-85 wt% oleic acid, 5-15 wt% palmitic acid, 2-10 wt% linoleic acid, 2-10 wt% stearic acid, 0.2-2 wt% arachidic acid, 0-1 wt% cis-11-eicosenoic acid, and 0-0.5 wt% linolenic acid.

[0058] The fatty acid composition of prune seed oil is 60-80 wt% oleic acid, 10-30 wt% linoleic acid, 0.5-5 wt% stearic acid, 0.5-3 wt% palmitoleic acid, 0-7 wt% palmitic acid, and 0-1 wt% linolenic acid.

[0059] The fatty acids of vegetable oils are affected by the variety of plant, soil, climate, place of origin, harvest time and extraction process, and the content of each component varies.For example, the main component of the fatty acids of olive oil is oleic acid, and other fatty acids include linoleic acid, palmitic acid, stearic acid and linolenic acid, which are essential components, while palmitoleic acid, arachidic acid, eicosenoic acid, heptadecanoic acid, heptadecenoic acid, behenic acid, lignoceric acid, myristic acid and the like do not necessarily need to be contained, and are optional or non-essential components.

[0060] The vegetable oil ceramide is at least two selected from oleic acid ceramide, linoleic acid ceramide, palmitic acid ceramide, linolenic acid ceramide, stearic acid ceramide, palmitoleic acid ceramide, arachidic acid ceramide, cis-11-eicosenoic acid ceramide, behenic acid ceramide, erucic acid ceramide, myristic acid ceramide, nervonic acid ceramide, lauric acid ceramide, eicosenoic acid ceramide, heptadecanoic acid ceramide, heptadecenoic acid ceramide, lignoceric acid ceramide, DHA ceramide, EPA ceramide, capric acid ceramide, caproic acid ceramide, xymenynic acid ceramide, cis-5-eicosenoic acid ceramide, cis-5,13-docosadienoic acid ceramide, and cis-5-docosenoic acid ceramide.

[0061] Specifically, the vegetable oil ceramides are 90 wt% or less of oleic acid ceramide, 90 wt% or less of linoleic acid ceramide, 30 wt% or less of palmitic acid ceramide, 90 wt% or less of linolenic acid ceramide, 55 wt% or less of stearic acid ceramide, 35 wt% or less of palmitoleic acid ceramide, 30 wt% or less of arachidic acid ceramide, 15 wt% or less of cis-11-eicosenoic acid ceramide, 4 wt% or less of behenic acid ceramide, 20 wt% or less of erucic acid ceramide, 50 wt% or less of myristic acid ceramide, 60 wt% or less of nervonic acid ceramide, and 70 wt% or less of lauric acid ceramide. ceramide, 0.4 wt% or less eicosenoic acid ceramide, 0.3 wt% or less heptadecanoic acid ceramide, 0.3 wt% or less heptadecenoic acid ceramide, 0.2 wt% or less lignoceric acid ceramide, 75 wt% or less DHA ceramide, 1 wt% or less EPA ceramide, 3 wt% or less capric acid ceramide, 3 wt% or less caproic acid ceramide, 15 wt% or less ximenynic acid ceramide, 80 wt% or less cis-5-eicosenoic acid ceramide, 25 wt% or less cis-5,13-docosadienoic acid ceramide, and 10 wt% or less cis-5-docosadienoic acid ceramide.

[0062] Linolenic acid ceramide refers to gamma-linolenic acid ceramide and / or alpha-linolenic acid ceramide.

[0063] JPEG2025536776000005.jpg43170

[0064] Oleic acid ceramide is obtained by the condensation reaction of oleic acid with a sphingosine-based compound, and includes 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 with a sphingosine-based compound, and includes 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 with a sphingosine-based compound, and includes palmitic acid phytosphingosine ceramide, palmitic acid sphingosine ceramide, and palmitic acid dihydrosphingosine ceramide. The same applies to other ceramides.

[0065] According to a second aspect of the present invention, a method for synthesizing vegetable oil ceramides comprises the following steps: A vegetable oil fatty acid is reacted with a sphingosine compound in the presence of a condensing agent and an organic base, where the condensing agent is DCC or EDCI, and the organic base is DMAP, DIPEA, NMM, or EtN.

[0066] Furthermore, the molar ratio of the vegetable oil fatty acid, the sphingosine compound, the condensing agent, and the organic base is 1:(1-1.5):(1-2):(0.2-2), and the solvent for the reaction is at least one of dichloromethane, tetrahydrofuran, ethyl acetate, and acetonitrile.

[0067] Since commercially available vegetable oils are generally in the form of fats and oils, which need to be hydrolyzed into vegetable oil fatty acids, the following steps are also included. Vegetable oil fats and oils are hydrolyzed by a saponification reaction to obtain vegetable oil fatty acids.

[0068] Furthermore, the saponification reaction is a hydrolysis of vegetable oil with a potassium hydroxide solution.

[0069] Furthermore, the mass ratio of the vegetable oil to potassium hydroxide is 1:(1 to 2).

[0070] A third aspect of the present invention is the use of vegetable oil ceramides in cosmetics, pharmaceuticals, dietary foods or health care products.

[0071] Furthermore, the plant oil ceramide has at least one of the following effects: skin barrier repair, tissue healing, anti-aging, anti-inflammation, anti-photoaging, antioxidant, promotion of collagen synthesis, maintenance of elastin activity, and whitening.

[0072] A composition comprising a plant oil ceramide, the composition having at least one of the following effects: skin barrier repair, tissue healing, anti-aging, anti-inflammatory, anti-photoaging, antioxidant, promoting collagen synthesis, maintaining elastin activity, and whitening.

[0073] The composition contains acceptable auxiliary materials including one or more of solubilizing agents, preservatives, antioxidants, pH adjusters, penetration enhancers, liposomes, moisturizing agents, thickeners, chelating agents, skin feel adjusters, surfactants, emulsifiers, essences, and pigments, and is in the form of a cream, emulsion, liquid, film, aerosol, or spray.

[0074] The present invention has the following beneficial effects: Plant oil ceramides are prepared by gently reacting fatty acids from plant oils with sphingosine compounds naturally present in skin, which exhibit excellent performance in repairing the skin's natural barrier, antioxidant properties, anti-aging properties, etc., and have a wide range of potential applications in the fields of cosmetics, health care products, biopharmaceuticals, etc.

[0075] 1. Superior efficacy compared to single ceramides. Different ceramides have different effects due to their different structures, and single-structure ceramides generally have difficulty in providing comprehensive effects. This solution is based on the idea of ​​bionics, and uses natural vegetable oils or fatty acids as raw materials to synthesize complex ceramides, thereby compensating for the difference in efficacy between different ceramides. Trace amounts of ceramide can be formed from trace amounts of fatty acids in vegetable oils, thereby achieving a complementary effect.

[0076] 2. Superior efficacy compared to blended ceramides. In addition to fatty acids (or fats and oils), vegetable oils also contain components such as vitamin A, carotenoids, resveratrol, tocopherol, sterols, amino acids, and trace elements, and these nutrients have different physiological activities. Ceramides synthesized using vegetable oils have a synergistic effect with other active ingredients contained in the vegetable oil, and are more effective than ceramides blended in similar proportions.

[0077] 3. Lower cost. The method of the present invention allows for the rapid production of compositions containing multiple ceramides. Vegetable oils and their fatty acids are obtained from a wide range of sources, are commercially available, low cost, environmentally friendly, and economical. This differs from the idea of ​​mixing and blending different single ceramides. Single-component fatty acids not only require high raw material prices, but also require the separate production of different ceramides before blending, which increases production costs.

[0078] 4. Simple synthesis method The method of the present invention can be realized by chemical synthesis to produce multiple ceramides in one step, or by microbial fermentation. [Brief explanation of the drawings]

[0079] [Figure 1-2] 1 is a bar graph showing the results of the cell proliferation activity test in Example 37. [Figure 3-5] 1 shows the results of the cell migration ability test in Example 38. [Figure 6-8] 1 is a bar graph showing the elastase inhibition rate of Example 39. [Figure 9-11] 1 is a bar graph showing the expression level of IL-6 factor in the measurement of anti-inflammatory repair efficacy in Example 40. [Figure 12-17] 1 is a bar graph of MMP1 expression levels in the anti-photoaging test of Example 41. [Figure 18-21] 1 is a bar graph showing the DPPH free radical scavenging rate in the antioxidant test of Example 42. [Figure 22-24]1 is a bar graph of melanin content in the whitening activity test of Example 43. DETAILED DESCRIPTION OF THE INVENTION

[0080] The present invention will be further described with reference to the following 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. Qingdao Haiyang Silica Gel (particle size 0.040-0.063 mm) was used for silica gel column chromatography. 60F254 silica gel plates were used for thin-layer chromatography (TLC), and UV light (254 nm) or iodine was used for TLC visualization.

[0081] Example 1 Synthesis of ceramides from olive oil fatty acids and sphingosine. Step 1: 50 g of olive oil was dissolved in 60 mL of tetrahydrofuran, cooled in an ice bath, and 100 mL of potassium hydroxide (25 wt%) solution was added dropwise. After the addition was complete, the temperature was raised to room temperature and the reaction was allowed to proceed until completion was confirmed by TLC.

[0082] Work-up: The pH of the reaction system was adjusted to 3 with dilute hydrochloric acid (3N), 150 mL of ethyl acetate was added to extract the aqueous phase, which was washed once with 100 mL of saturated brine, and the organic phase was dried with anhydrous Na2SO4, filtered, and concentrated under vacuum to obtain 40 g of olive oil fatty acids.

[0083] Step 2: Olive oil fatty acid (50 mmol, molecular weight calculated as oleic acid), EDCI (75 mmol), and EtN (75 mmol) were added to a 250 mL round-bottom flask, and 100 mL of dichloromethane was added. The mixture was stirred at room temperature for 1 hour. Sphingosine (50 mmol) was then added to the reaction mixture, and the mixture was stirred at room temperature until the reaction was complete as determined by TLC.

[0084] Workup: The reaction was quenched with water, and the organic layer was separated, dried, filtered, concentrated under vacuum, and washed with solvent to obtain olive oil ceramide. The product was analyzed by HPLC. HPLC conditions: A Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) was used, with an Innoval ODS-2 4.6*250mm, 5μm chromatography column. Column temperature: 30°C, injection volume: 10μL, flow rate: 1.0mL / min, evaporation temperature: 40°C, carrier gas flow rate: 2.5L / min, and mobile phase: (2wt% water + 98wt% methanol), both containing 0.1wt% formic acid.

[0085] The retention times of the main components in HPLC were 20.7 minutes for oleic acid-sphingosine ceramide and 16.6 minutes for linoleic acid-sphingosine ceramide.

[0086] The resulting product was analyzed by high-performance liquid chromatography, revealing that 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 (the nuclear magnetic resonance hydrogen spectrum was compared with the standard spectrum and matched) were 61.8%, 12.6%, 19.3%, 3.4%, and 0.6%, respectively, with the remainder consisting of other components present in small amounts. The main component of the imported olive oil fatty acid used in this example was oleic acid, and the resulting product was mainly oleic acid ceramide.

[0087] Hydrogen spectrum of oleic acid-sphingosine ceramide: 1H NMR (400 MHz, methanol-d4) δ 7.70 (d, J = 8.9 Hz, 1H), 5.69 (dt, J = 15.3, 6.7 Hz, 1H), 5.45 (dd, J = 15.4, 7.5 Hz, 1H), 5.34 (t, J = 4.9 Hz, 2H), 4.03 (t, J = 7.5 Hz, 1H), 3.85 (ddd, J = 9.5, 4.6, 2.4 Hz, 1H), 3.68 (d, J = 5.0 Hz, 2H), 2.19 (t, J = 7.6 Hz, 2H), 2.03 (q, J = 6.9, 6.0 Hz, 6H), 1.64 - 1.51 (m, 2H), 1.30 (d, J = 14.5 Hz, 41H), 0.90 (t, J = 6.7 Hz, 6H). Hydrogen spectrum of linoleic acid-sphingosine ceramide: 1 H NMR (400 MHz, methanol-d4) δ 7.69 (d, J = 8.9 Hz, 1H), 5.69 (dt, J = 15.3, 6.7 Hz, 1H), 5.46 (dd, J = 15.3, 7.4 Hz, 1H), 5.41 - 5.25 (m, 4H), 4.03 (t, J = 7.5 Hz, 1H), 3.85 (tdd, J = 7.5, 4.7, 2.2 Hz, 1H), 3.68 (d, J = 5.0 Hz, 2H), 2.77 (t, J = 6.4 Hz, 2H), 2.20 (q, J = 7.6, 6.9 Hz, 2H), 2.13 - 1.94 (m, 6H), 1.67 - 1.49 (m, 2H), 1.31 (d, J = 19.6 Hz, 40H), 0.90 (td, J = 6.8, 3.8 Hz, 6H).

[0088] In this example, ceramide was synthesized from olive oil fatty acids, phytosphingosine, and dihydrosphingosine.

[0089] Example 2 Synthesis of ceramides from tea oil fatty acids and phytosphingosine. Step 1: 50 g of tea oil was dissolved in 60 mL of tetrahydrofuran, cooled in an ice bath, and 100 mL of potassium hydroxide (25 wt%) solution was added dropwise. After the addition was complete, the temperature was raised to room temperature and the reaction was allowed to proceed until completion was confirmed by TLC.

[0090] Post-treatment: Dilute hydrochloric acid (3N) was added to adjust the pH 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. Anhydrous Na2SO4 was added to dry the organic phase, which was then filtered and concentrated under vacuum to obtain 40.3 g of tea oil fatty acids.

[0091] Step 2: Tea oil fatty acids (50 mmol, calculated as the main fatty acid), DCC (60 mmol), and DMAP (10 mmol) were added to a 250 mL round-bottom flask, and 100 mL of dichloromethane was added. The mixture was stirred at room temperature for 1 hour. Phytosphingosine (60 mmol) was then added to the reaction mixture, and the mixture was stirred at room temperature until the reaction was complete as determined by TLC.

[0092] Workup: The reaction mixture was filtered to remove solids. The filtrate was collected and washed with saturated sodium bicarbonate, 1N dilute hydrochloric acid, and saturated brine. The organic layer was separated, dried, filtered, concentrated under vacuum, and then washed with solvent to obtain tea oil ceramide. The product was analyzed by HPLC. HPLC conditions: A Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) was used, with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0093] The retention times of each component in HPLC were as follows: linolenic acid-phytosphingosine ceramide 8.3 minutes, linoleic acid-phytosphingosine ceramide 9.5 minutes, palmitic acid-phytosphingosine ceramide 10.7 minutes, oleic acid-phytosphingosine ceramide 11.3 minutes, and stearic acid-phytosphingosine ceramide 13.9 minutes.

[0094] 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, with the remainder being other components with low contents.

[0095] In accordance with this example, ceramide was synthesized from tea oil fatty acid, sphingosine, and dihydrosphingosine.

[0096] Example 3 Synthesis of ceramide from sea buckthorn oil fatty acids and dihydrosphingosine Step 1: 50 g of sea buckthorn oil was dissolved in 60 mL of tetrahydrofuran, cooled in an ice bath, and 100 mL of potassium hydroxide (25 wt%) solution was added dropwise. After the addition was complete, the temperature was raised to room temperature and the reaction was allowed to proceed until completion was confirmed by TLC.

[0097] Post-treatment: Dilute hydrochloric acid (3N) was added to adjust the pH 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. Anhydrous Na2SO4 was added to dry the organic phase, which was then filtered and concentrated under vacuum to obtain 39.6 g of sea buckthorn oil fatty acids.

[0098] Step 2: Sea buckthorn oil fatty acid (50 mmol, calculated as the main fatty acid), EDCI (80 mmol), and EtN (80 mmol) were added to a 250 mL round-bottom flask, and 100 mL of dichloromethane was added. The mixture was stirred at room temperature for 1 hour. Dihydrosphingosine (60 mmol) was then added to the reaction mixture, and the mixture was stirred at room temperature until completion was confirmed by TLC.

[0099] Workup: Water was added to quench the reaction, and the organic layer was separated, dried, filtered, concentrated under vacuum, and washed with solvent to obtain sea buckthorn oil ceramide. The product was analyzed by HPLC. Chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0100] The retention times of each component in HPLC were as follows: linolenic acid-dihydrosphingosine ceramide 8.3 minutes, palmitoleic acid-dihydrosphingosine ceramide 9.0 minutes, linoleic acid-dihydrosphingosine ceramide 9.6 minutes, palmitic acid-dihydrosphingosine ceramide 10.6 minutes, oleic acid-dihydrosphingosine ceramide 11.1 minutes, and stearic acid-dihydrosphingosine ceramide 13.6 minutes.

[0101] The obtained product was analyzed by high-performance liquid chromatography, and the contents of oleic acid-dihydrosphingosine ceramide, palmitic acid-dihydrosphingosine ceramide, linoleic acid-dihydrosphingosine ceramide, linolenic acid-dihydrosphingosine ceramide, palmitoleic acid-dihydrosphingosine ceramide, and stearic acid-dihydrosphingosine ceramide were 28%, 27%, 6%, 25%, 7%, and 1%, respectively, and the remainder was made up of other components with low contents.

[0102] In this example, ceramide was synthesized from sea buckthorn oil fatty acids, sphingosine, and phytosphingosine.

[0103] Example 4 Synthesis of ceramides from grape seed oil fatty acids and phytosphingosine. Step 1: 50 g of grape seed oil was dissolved in 60 mL of tetrahydrofuran, cooled in an ice bath, and 100 mL of potassium hydroxide (25 wt%) solution was added dropwise. After the addition was complete, the temperature was raised to room temperature and the reaction was allowed to proceed until completion was confirmed by TLC.

[0104] Work-up: The pH of the reaction system was adjusted to 3 with dilute hydrochloric acid (3N), 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 dried with anhydrous Na2SO4, filtered, and concentrated under vacuum to obtain 40 g of grape seed oil fatty acids.

[0105] Step 2: Grape seed oil fatty acids (50 mmol, calculated as the main fatty acid), EDCI (60 mmol), and DIPEA (60 mmol) were added to a 250 mL round-bottom flask, and 100 mL of dichloromethane was added. The mixture was stirred at room temperature for 1 hour. Phytosphingosine (60 mmol) was then added to the reaction mixture, and the mixture was stirred at room temperature until completion was confirmed by TLC.

[0106] Workup: The reaction was quenched by adding water, and the organic layer was separated, dried, filtered, concentrated under vacuum, and washed with solvent to obtain grape seed oil ceramide. The product was analyzed by HPLC. HPLC conditions: A Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) was used, with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0107] The retention times of each component in HPLC were as follows: palmitoleic acid-phytosphingosine ceramide 8.0 minutes, linolenic acid-phytosphingosine ceramide 8.3 minutes, linoleic acid-phytosphingosine ceramide 9.4 minutes, palmitic acid-phytosphingosine ceramide 10.6 minutes, oleic acid-phytosphingosine ceramide 11.2 minutes, and stearic acid-phytosphingosine ceramide 13.8 minutes.

[0108] 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, palmitoleic acid-phytosphingosine ceramide, and linolenic acid-phytosphingosine ceramide were 61%, 22%, 7%, 3%, 1%, and 1%, respectively, and the remainder was made up of other components with low amounts.

[0109] In this example, ceramide was synthesized from grape seed oil fatty acids, sphingosine, and dihydrosphingosine.

[0110] Example 5 Nut oil ceramide was synthesized from nut oil fatty acids and sphingosine using Example 2. The product was analyzed by HPLC. Chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0111] The retention times of each component in HPLC were as follows: linolenic acid-sphingosine ceramide 7.9 minutes, palmitoleic acid-sphingosine ceramide 8.2 minutes, linoleic acid-sphingosine ceramide 8.7 minutes, oleic acid-sphingosine ceramide 10.2 minutes, palmitic acid-sphingosine ceramide 10.4 minutes, cis-11-eicosenoic acid-sphingosine ceramide 12.8 minutes, stearic acid-sphingosine ceramide 13.6 minutes, arachidic acid-sphingosine ceramide 17.8 minutes, and behenic acid-sphingosine ceramide 24.0 minutes.

[0112] The obtained product was analyzed by high-performance liquid chromatography, and the contents of oleic acid-sphingosine ceramide, palmitoleic acid-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 cis-11-eicosenoic acid-sphingosine ceramide were 58%, 24%, 5%, 3%, 1%, 4%, 0.5%, 0.5%, and 2%, respectively, and the remainder was made up of other components with low amounts.

[0113] In this example, ceramide was synthesized from nut oil fatty acids, phytosphingosine, and dihydrosphingosine.

[0114] Example 6 Borage oil ceramide was synthesized from borage oil fatty acids and dihydrosphingosine as described in Example 3. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250 mm, 5 μm chromatography 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.

[0115] The retention times of each component in HPLC were as follows: γ-linolenic acid-dihydrosphingosine ceramide 8.3 minutes, linoleic acid-dihydrosphingosine ceramide 9.5 minutes, palmitic acid-dihydrosphingosine ceramide 10.6 minutes, oleic acid-dihydrosphingosine ceramide 11.2 minutes, stearic acid-dihydrosphingosine ceramide 13.5 minutes, and erucic acid-dihydrosphingosine ceramide 18.7 minutes.

[0116] 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, with the remainder being other components with low contents.

[0117] In this example, ceramide was synthesized from borage oil fatty acid, sphingosine, and phytosphingosine.

[0118] Example 7 Rosehip oil ceramide was synthesized from rosehip oil fatty acids and phytosphingosine using Example 2. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0119] The retention times of each component in HPLC were as follows: linolenic acid-phytosphingosine ceramide 8.3 minutes, linoleic acid-phytosphingosine ceramide 9.5 minutes, palmitic acid-phytosphingosine ceramide 10.6 minutes, oleic acid-phytosphingosine ceramide 11.2 minutes, cis-11-eicosenoic acid-phytosphingosine ceramide 12.9 minutes, stearic acid-phytosphingosine ceramide 13.9 minutes, and arachidic acid-phytosphingosine ceramide 16.5 minutes.

[0120] 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 cis-11-eicosenoic acid-phytosphingosine ceramide were 51%, 26%, 10%, 3%, 4%, 0.5%, and 1%, respectively, and the remainder was made up of other components with low amounts.

[0121] In this example, ceramide was synthesized from rosehip oil fatty acids, sphingosine, and dihydrosphingosine.

[0122] Example 8 Synthesis of ceramide from soybean oil fatty acids and sphingosine Soybean oil fatty acids (50 mmol, calculated as the main fatty acid), EDCI (65 mmol), and DIPEA (65 mmol) were added to a 250 mL round-bottom flask, and 100 mL of dichloromethane was added. The mixture was stirred at room temperature for 1 hour, and then sphingosine (60 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature until completion of the reaction was confirmed by TLC.

[0123] Workup: The reaction was quenched by adding water, and the organic layer was separated, dried, filtered, concentrated under vacuum, and then washed with solvent to obtain soybean oil ceramide. The product was analyzed by HPLC. Chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0124] The retention times of each component in HPLC were as follows: linolenic acid-sphingosine ceramide 7.9 minutes, linoleic acid-sphingosine ceramide 8.7 minutes, oleic acid-sphingosine ceramide 10.2 minutes, palmitic acid-sphingosine ceramide 10.5 minutes, and stearic acid-sphingosine ceramide 13.5 minutes.

[0125] 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, with the remainder being other components with low contents.

[0126] In this example, ceramide was synthesized from soybean oil fatty acids, phytosphingosine, and dihydrosphingosine.

[0127] Example 9 Rice bran oil ceramide was synthesized from rice bran oil fatty acids and dihydrosphingosine using the same procedure as in Example 8. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0128] The retention times of each component in HPLC were as follows: linolenic acid-dihydrosphingosine ceramide 8.3 minutes, linoleic acid-dihydrosphingosine ceramide 9.5 minutes, palmitic acid-dihydrosphingosine ceramide 10.5 minutes, oleic acid-dihydrosphingosine ceramide 11.1 minutes, stearic acid-dihydrosphingosine ceramide 13.5 minutes, and arachidic acid-dihydrosphingosine ceramide 16.1 minutes.

[0129] 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 remainder was made up of other components with low contents.

[0130] In accordance with this example, ceramide was synthesized from rice bran oil fatty acids, sphingosine, and phytosphingosine.

[0131] Example 10 Synthesis of ceramides from cottonseed oil fatty acids and phytosphingosine. Step 1: 50 g of cottonseed oil was dissolved in 60 mL of tetrahydrofuran, cooled in an ice bath, and 100 mL of potassium hydroxide (25 wt%) solution was added dropwise. After the addition was complete, the temperature was raised to room temperature and the reaction was allowed to proceed until completion was confirmed by TLC.

[0132] Post-treatment: Dilute hydrochloric acid (3N) was added to adjust the pH 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. Anhydrous Na2SO4 was added to dry the organic phase, which was then filtered and concentrated under vacuum to obtain 40.5 g of cottonseed oil fatty acids.

[0133] Step 2: Cottonseed oil fatty acids (50 mmol, calculated as the main fatty acid), EDCI (65 mmol), and NMM (65 mmol) were added to a 250 mL round-bottom flask, and 100 mL of dichloromethane was added. The mixture was stirred at room temperature for 1 hour. Phytosphingosine (55 mmol) was then added to the reaction mixture, and the mixture was stirred at room temperature until the reaction was complete as determined by TLC.

[0134] Workup: The reaction was quenched by adding water, and the organic layer was separated, dried, filtered, concentrated under vacuum, and washed with solvent to obtain cottonseed oil ceramide. The product was analyzed by HPLC. Chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0135] The retention times of each component in HPLC were as follows: palmitoleic acid-phytosphingosine ceramide 8.1 minutes, linolenic acid-phytosphingosine ceramide 8.3 minutes, linoleic acid-phytosphingosine ceramide 9.5 minutes, palmitic acid-phytosphingosine ceramide 10.7 minutes, oleic acid-phytosphingosine ceramide 11.3 minutes, stearic acid-phytosphingosine ceramide 13.9 minutes, and arachidic acid-phytosphingosine ceramide 16.5 minutes.

[0136] 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 remainder was made up of other components with low amounts.

[0137] In this example, ceramide was synthesized from cottonseed oil fatty acids, sphingosine, and dihydrosphingosine.

[0138] Example 11 Inca inchioyl ceramide was synthesized from inca inchioyl fatty acid and sphingosine according to Example 1. The product was analyzed by HPLC. Chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250 mm, 5 μm chromatography 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.

[0139] The retention times of each component in HPLC were as follows: linolenic acid-sphingosine ceramide 7.9 minutes, linoleic acid-sphingosine ceramide 8.6 minutes, oleic acid-sphingosine ceramide 10.2 minutes, palmitic acid-sphingosine ceramide 10.4 minutes, and stearic acid-sphingosine ceramide 13.6 minutes.

[0140] 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 remainder was made up of other components with low contents.

[0141] In this example, ceramide was synthesized from inca inchioil fatty acid, phytosphingosine, and dihydrosphingosine.

[0142] Example 12 Watermelon seed oil ceramide was synthesized from watermelon seed oil fatty acids and dihydrosphingosine using Example 10. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0143] The retention times of the individual components in HPLC were as follows: linoleic acid-dihydrosphingosine ceramide 9.5 minutes, palmitic acid-dihydrosphingosine ceramide 10.5 minutes, oleic acid-dihydrosphingosine ceramide 11.1 minutes, and stearic acid-dihydrosphingosine ceramide 13.5 minutes.

[0144] 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 remainder was made up of other components with low contents.

[0145] In this example, ceramide was synthesized from watermelon seed oil fatty acids, phytosphingosine, and sphingosine.

[0146] Example 13 Synthesis of ceramides from coconut oil fatty acids and phytosphingosine. Coconut oil fatty acids (50 mmol, calculated as the main fatty acid), EDCI (65 mmol), and EtN (65 mmol) were added to a 250 mL round-bottom flask, and 100 mL of dichloromethane was added. The mixture was stirred at room temperature for 1 hour. Phytosphingosine (55 mmol) was then added to the reaction mixture, and the mixture was stirred at room temperature until the reaction was complete as confirmed by TLC.

[0147] Workup: The reaction was quenched by adding water, and the organic layer was separated, dried, filtered, concentrated under vacuum, and washed with solvent to obtain coconut oil ceramide. The product was analyzed by HPLC. Chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0148] The retention times of each component in HPLC were as follows: caproic acid-phytosphingosine ceramide 5.7 minutes, capric acid-phytosphingosine ceramide 6.3 minutes, lauric acid-phytosphingosine ceramide 7.5 minutes, myristic acid-phytosphingosine ceramide 9.4 minutes, palmitic acid-phytosphingosine ceramide 10.7 minutes, oleic acid-phytosphingosine ceramide 11.3 minutes, and stearic acid-phytosphingosine ceramide 13.9 minutes.

[0149] 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 remainder was made up of other components with low contents.

[0150] In this example, ceramide was synthesized from coconut oil fatty acids, sphingosine, and dihydrosphingosine.

[0151] Example 14 Referring to Example 4, ceramide from tallow seed oil was synthesized from tallow seed oil fatty acids and sphingosine. The product was analyzed by HPLC. Chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250 mm, 5 μm chromatography 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.

[0152] The retention times of each component in HPLC were as follows: linolenic acid-sphingosine ceramide 7.9 minutes, linoleic acid-sphingosine ceramide 8.7 minutes, oleic acid-sphingosine ceramide 10.1 minutes, palmitic acid-sphingosine ceramide 10.4 minutes, cis-11-eicosenoic acid-sphingosine ceramide 12.7 minutes, stearic acid-sphingosine ceramide 13.5 minutes, and arachidic acid-sphingosine ceramide 17.8 minutes.

[0153] 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, cis-11-eicosenoic 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 remainder was made up of other components with low amounts.

[0154] In this example, ceramide was synthesized from fatty acids of Prunus persica seed oil, phytosphingosine, and dihydrosphingosine.

[0155] Example 15 Walnut oil ceramide was synthesized from walnut oil fatty acids and dihydrosphingosine as described in Example 4. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250 mm, 5 μm chromatography 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.

[0156] The retention times of the individual components in HPLC were as follows: linolenic acid-dihydrosphingosine ceramide 8.3 minutes, linoleic acid-dihydrosphingosine ceramide 9.5 minutes, palmitic acid-dihydrosphingosine ceramide 10.6 minutes, and oleic acid-dihydrosphingosine ceramide 11.1 minutes.

[0157] 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, with the remainder being other components with low contents.

[0158] In this example, ceramide was synthesized from walnut oil fatty acids, phytosphingosine, and sphingosine.

[0159] Example 16 Avocado oil ceramide was synthesized from avocado oil fatty acids and phytosphingosine as described in Example 1. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0160] The retention times of each component in HPLC were as follows: palmitoleic acid-phytosphingosine ceramide 8.0 minutes, linolenic acid-phytosphingosine ceramide 8.3 minutes, linoleic acid-phytosphingosine ceramide 9.5 minutes, palmitic acid-phytosphingosine ceramide 10.7 minutes, oleic acid-phytosphingosine ceramide 11.3 minutes, eicosenoic acid-phytosphingosine ceramide 12.9 minutes, and stearic acid-phytosphingosine ceramide 13.9 minutes.

[0161] 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 eicosenoic acid-phytosphingosine ceramide were 70%, 10%, 7%, 8%, 1%, 0.5%, and 0.5%, respectively, and the remainder were other components with low content.

[0162] In this example, ceramide was synthesized from avocado oil fatty acids, sphingosine, and dihydrosphingosine.

[0163] Example 17 Tomato seed oil ceramide was synthesized from tomato seed oil fatty acids and sphingosine as described in Example 4. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250 mm, 5 μm chromatography 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.

[0164] The retention times of each component in HPLC were as follows: linolenic acid-sphingosine ceramide 7.9 minutes, linoleic acid-sphingosine ceramide 8.7 minutes, oleic acid-sphingosine ceramide 10.2 minutes, palmitic acid-sphingosine ceramide 10.4 minutes, stearic acid-sphingosine ceramide 13.6 minutes, and arachidic acid-sphingosine ceramide 17.8 minutes.

[0165] 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 remainder was made up of other components with low contents.

[0166] In this example, ceramide was synthesized from tomato seed oil fatty acids, phytosphingosine, and dihydrosphingosine.

[0167] Example 18 Sea pine seed oil ceramide was synthesized from sea pine seed oil fatty acids and dihydrosphingosine using Example 2. The product was analyzed by HPLC. Chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0168] The retention times of each component in HPLC were as follows: linolenic acid-dihydrosphingosine ceramide 8.3 minutes, oleic acid-dihydrosphingosine ceramide 11.1 minutes, stearic acid-dihydrosphingosine ceramide 13.5 minutes, ximenynic acid-dihydrosphingosine ceramide 17.2 minutes, behenic acid-dihydrosphingosine ceramide 21.8 minutes, and nervonic acid-dihydrosphingosine ceramide 24.1 minutes.

[0169] The resulting 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, with the remainder being other components with low contents.

[0170] In this example, ceramide was synthesized from fatty acids of sea buckthorn seed oil, phytosphingosine, and sphingosine.

[0171] Example 19 Synthesis of ceramides from blue thorn oil fatty acids and phytosphingosine. Step 1: 50 g of green thorn oil was dissolved in 80 mL of tetrahydrofuran, cooled in an ice bath, and 100 mL of potassium hydroxide (25 wt%) solution was added dropwise. After the addition was complete, the temperature was raised to room temperature and the reaction was allowed to proceed until completion was confirmed by TLC.

[0172] Post-treatment: Dilute hydrochloric acid (3N) was added to adjust the pH of the reaction system to 3, 120 mL of ethyl acetate was added to extract the aqueous phase, and 100 mL of saturated brine was added to wash once. Anhydrous Na2SO4 was added to dry the organic phase, which was then filtered and concentrated under vacuum to obtain 40.6 g of blue thorn oil fatty acids.

[0173] Step 2: Add the fatty acids from blue thorn fruit oil (50 mmol, calculated as the main fatty acid), EDCI (55 mmol), and DMAP (55 mmol) to a 250 mL round-bottom flask, add 100 mL of dichloromethane, and stir at room temperature for 1 hour. Then, add phytosphingosine (55 mmol) to the reaction mixture and stir at room temperature until the reaction was complete as confirmed by TLC.

[0174] Workup: The reaction was quenched by adding water, and the organic layer was separated, dried, filtered, concentrated under vacuum, and then washed with solvent to obtain the green thorn fruit oil ceramide. The product was analyzed by HPLC. Chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography column was used; 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.

[0175] The retention times of each component in HPLC were as follows: linoleic acid-phytosphingosine ceramide 9.5 minutes, palmitic acid-phytosphingosine ceramide 10.7 minutes, oleic acid-phytosphingosine ceramide 11.3 minutes, stearic acid-phytosphingosine ceramide 13.9 minutes, and arachidic acid-phytosphingosine ceramide 16.5 minutes.

[0176] 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, with the remainder being other components with low contents.

[0177] In this example, ceramide was synthesized from fatty acids of blue thorn fruit oil, sphingosine, and dihydrosphingosine.

[0178] Example 20 Safflower seed oil ceramide was synthesized from safflower seed oil fatty acids and sphingosine using the same procedure as in Example 4. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250 mm, 5 μm chromatography 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.

[0179] The retention times of each component in HPLC were as follows: linolenic acid-sphingosine ceramide 7.9 minutes, linoleic acid-sphingosine ceramide 8.7 minutes, oleic acid-sphingosine ceramide 10.2 minutes, palmitic acid-sphingosine ceramide 10.4 minutes, stearic acid-sphingosine ceramide 13.5 minutes, and arachidic acid-sphingosine ceramide 17.7 minutes.

[0180] 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, with the remainder being other components with low contents.

[0181] In this example, ceramide was synthesized from safflower seed oil fatty acids, phytosphingosine, and dihydrosphingosine.

[0182] Example 21 Referring to Example 3, cereal ceramide was synthesized from cereal cereal oil fatty acids and dihydrosphingosine. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0183] The retention times of each component in HPLC were as follows: α-linolenic acid-dihydrosphingosine ceramide 8.3 minutes, linoleic acid-dihydrosphingosine ceramide 9.5 minutes, palmitic acid-dihydrosphingosine ceramide 10.6 minutes, oleic acid-dihydrosphingosine ceramide 11.2 minutes, and stearic acid-dihydrosphingosine ceramide 13.5 minutes.

[0184] 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, with the remainder being other components with low contents.

[0185] In this example, ceramide was synthesized from paeonia suffruticosa seed oil fatty acids, phytosphingosine, and sphingosine.

[0186] Example 22 Sunflower seed oil ceramide was synthesized from sunflower seed oil fatty acids and phytosphingosine as described in Example 4. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0187] The retention times of each component in HPLC were as follows: linoleic acid-phytosphingosine ceramide 9.4 minutes, palmitic acid-phytosphingosine ceramide 10.7 minutes, oleic acid-phytosphingosine ceramide 11.3 minutes, stearic acid-phytosphingosine ceramide 13.9 minutes, arachidic acid-phytosphingosine ceramide 16.5 minutes, and behenic acid-phytosphingosine ceramide 18.3 minutes.

[0188] 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 remainder was made up of other components with low contents.

[0189] In this example, ceramide was synthesized from sunflower seed oil fatty acids, sphingosine, and dihydrosphingosine.

[0190] Example 23 Perilla seed oil ceramide was synthesized from perilla seed oil fatty acids and sphingosine using Example 1. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250 mm, 5 μm chromatography 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.

[0191] The retention times of each component in HPLC were as follows: α-linolenic acid-sphingosine ceramide 7.9 minutes, linoleic acid-sphingosine ceramide 8.7 minutes, oleic acid-sphingosine ceramide 10.2 minutes, palmitic acid-sphingosine ceramide 10.4 minutes, and stearic acid-sphingosine ceramide 13.6 minutes.

[0192] 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 found to be 70%, 15%, 7%, 2%, and 2%, respectively, with the remainder consisting of other components with low contents.

[0193] In this example, ceramide was synthesized from perilla seed oil fatty acids, phytosphingosine, and dihydrosphingosine.

[0194] Example 24 Flaxseed oil ceramide was synthesized from linseed oil fatty acids and dihydrosphingosine as described in Example 3. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0195] The retention times of each component in HPLC were as follows: linolenic acid-dihydrosphingosine ceramide 8.3 minutes, linoleic acid-dihydrosphingosine ceramide 9.5 minutes, palmitic acid-dihydrosphingosine ceramide 10.7 minutes, oleic acid-dihydrosphingosine ceramide 11.1 minutes, and stearic acid-dihydrosphingosine ceramide 13.6 minutes.

[0196] 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 remainder was made up of other components with low contents.

[0197] In this example, ceramide was synthesized from linseed oil fatty acids, phytosphingosine, and sphingosine.

[0198] Example 25 Milk thistle oil ceramide was synthesized from milk thistle oil fatty acids and phytosphingosine as described in Example 4. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0199] The retention times of each component in HPLC were as follows: linolenic acid-phytosphingosine ceramide 8.2 minutes, linoleic acid-phytosphingosine ceramide 9.5 minutes, palmitic acid-phytosphingosine ceramide 10.7 minutes, oleic acid-phytosphingosine ceramide 11.3 minutes, stearic acid-phytosphingosine ceramide 13.9 minutes, arachidic acid-phytosphingosine ceramide 16.5 minutes, and behenic acid-phytosphingosine ceramide 18.3 minutes.

[0200] 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 remainder was made up of other components with low contents.

[0201] In this example, ceramide was synthesized from milk thistle oil fatty acids, sphingosine, and dihydrosphingosine.

[0202] Example 26 Shea butter ceramide was synthesized from shea butter fatty acids and sphingosine using the same procedure as in Example 4. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250 mm, 5 μm chromatography 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.

[0203] The retention times of each component in HPLC were as follows: linoleic acid-sphingosine ceramide 8.7 minutes, oleic acid-sphingosine ceramide 10.2 minutes, palmitic acid-sphingosine ceramide 10.5 minutes, stearic acid-sphingosine ceramide 13.6 minutes, and arachidic acid-sphingosine ceramide 17.8 minutes.

[0204] 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 remainder was made up of other components with low contents.

[0205] In this example, ceramide was synthesized from shea butter fatty acids, phytosphingosine, and dihydrosphingosine.

[0206] Example 27 As in Example 4, evening primrose oil ceramide was synthesized from evening primrose oil fatty acids and dihydrosphingosine. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0207] The retention times of each component in HPLC were as follows: γ-linolenic acid-dihydrosphingosine ceramide 8.2 minutes, linoleic acid-dihydrosphingosine ceramide 9.5 minutes, palmitic acid-dihydrosphingosine ceramide 10.6 minutes, oleic acid-dihydrosphingosine ceramide 11.0 minutes, stearic acid-dihydrosphingosine ceramide 13.5 minutes, and cis-11-eicosenoic acid-dihydrosphingosine ceramide 14.0 minutes.

[0208] 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 cis-11-eicosenoic acid-dihydrosphingosine ceramide were 65%, 16%, 10%, 2%, 2%, and 1%, respectively, and the remainder was made up of other components with low contents.

[0209] In this example, ceramide was synthesized from evening primrose oil fatty acids, phytosphingosine, and sphingosine.

[0210] Example 28 Argan oil ceramide was synthesized from argan oil fatty acids and phytosphingosine using Example 1. The product was analyzed by HPLC. Chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0211] The retention times of each component in HPLC were as follows: linolenic acid-phytosphingosine ceramide 8.3 minutes, linoleic acid-phytosphingosine ceramide 9.5 minutes, palmitic acid-phytosphingosine ceramide 10.7 minutes, oleic acid-phytosphingosine ceramide 11.3 minutes, cis-11-eicosenoic acid-phytosphingosine ceramide 12.9 minutes, stearic acid-phytosphingosine ceramide 13.9 minutes, arachidic acid-phytosphingosine ceramide 16.5 minutes, and behenic acid-phytosphingosine ceramide 18.3 minutes.

[0212] 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 cis-11-eicosenoic acid-phytosphingosine ceramide were 50%, 33%, 5%, 6%, 0.5%, 0.5%, 0.5%, and 0.5%, respectively, and the remainder were other components with low content.

[0213] In this example, ceramide was synthesized from argan oil fatty acids, sphingosine, and dihydrosphingosine.

[0214] Example 29 Hemp seed oil ceramide was synthesized from hemp seed oil fatty acids and sphingosine using Example 2. The product was analyzed by HPLC. Chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography column; column temperature: 30℃; injection volume: 10μL; flow rate: 1.0mL / min; evaporation temperature: 40℃; carrier gas flow rate: 2.5L / min; mobile phase: 100% methanol.

[0215] The retention times of each component in HPLC were as follows: linolenic acid-sphingosine ceramide 7.9 minutes, linoleic acid-sphingosine ceramide 8.7 minutes, oleic acid-sphingosine ceramide 10.2 minutes, palmitic acid-sphingosine ceramide 10.4 minutes, and stearic acid-sphingosine ceramide 13.5 minutes.

[0216] 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, with the remainder being other components with low contents.

[0217] In this example, ceramide was synthesized from hemp seed oil fatty acids, phytosphingosine, and dihydrosphingosine.

[0218] Example 30 Meadowfoam seed oil ceramide was synthesized from meadowfoam seed oil fatty acids and phytosphingosine as described in Example 3. The product was analyzed by HPLC. Chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0219] The retention times of each component in HPLC were as follows: oleic acid-phytosphingosine ceramide 11.3 minutes, cis-5-eicosenoic acid-phytosphingosine ceramide 22.6 minutes, cis-5,13-docosadienoic acid-phytosphingosine ceramide 23.8 minutes, erucic acid-phytosphingosine ceramide 28.8 minutes, and cis-5-docosenoic acid-phytosphingosine ceramide 32.6 minutes.

[0220] 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-docosanoic acid-phytosphingosine ceramide, and oleic acid-phytosphingosine ceramide were 55%, 21%, 15%, 4%, and 1%, respectively, and the remainder was made up of other components with low contents.

[0221] In this example, ceramide was synthesized from meadowfoam seed oil fatty acids, sphingosine, and dihydrosphingosine.

[0222] Example 31 Baobab seed oil ceramide was synthesized from baobab seed oil fatty acids and dihydrosphingosine using Example 3. The product was analyzed by HPLC. Chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0223] The retention times of each component in HPLC were as follows: linolenic acid-dihydrosphingosine ceramide 8.2 minutes, myristic acid-dihydrosphingosine ceramide 8.5 minutes, palmitoleic acid-dihydrosphingosine ceramide 8.9 minutes, linoleic acid-dihydrosphingosine ceramide 9.5 minutes, palmitic acid-dihydrosphingosine ceramide 10.7 minutes, oleic acid-dihydrosphingosine ceramide 11.1 minutes, stearic acid-dihydrosphingosine ceramide 13.5 minutes, and arachidic acid-dihydrosphingosine ceramide 16.0 minutes.

[0224] 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 remainder was made up of other components with low amounts.

[0225] In this example, ceramide was synthesized from baobab seed oil fatty acids, phytosphingosine, and sphingosine.

[0226] Example 32 Prickly pear seed oil ceramide was synthesized from prickly pear seed oil fatty acids and sphingosine as described in Example 19. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0227] The retention times of each component in HPLC were as follows: linolenic acid-sphingosine ceramide 7.9 minutes, palmitoleic acid-sphingosine ceramide 8.2 minutes, oleic acid-sphingosine ceramide 10.2 minutes, palmitic acid-sphingosine ceramide 10.5 minutes, stearic acid-sphingosine ceramide 13.6 minutes, and arachidic acid-sphingosine ceramide 17.8 minutes.

[0228] 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 remainder was made up of other components with low amounts.

[0229] In this example, ceramide was synthesized from prickly pear seed oil fatty acids, phytosphingosine, and dihydrosphingosine.

[0230] Example 33 Wheat germ oil ceramide was synthesized from wheat germ oil fatty acids and dihydrosphingosine as described in Example 3. The product was analyzed by HPLC. Chromatography conditions were as follows: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0231] The retention times of each component in HPLC were as follows: linolenic acid-dihydrosphingosine ceramide 8.3 minutes, linoleic acid-dihydrosphingosine ceramide 9.5 minutes, palmitic acid-dihydrosphingosine ceramide 10.6 minutes, oleic acid-dihydrosphingosine ceramide 11.1 minutes, stearic acid-dihydrosphingosine ceramide 13.5 minutes, cis-11-eicosenoic acid-dihydrosphingosine ceramide 14.0 minutes, and arachidic acid-dihydrosphingosine ceramide 16.0 minutes.

[0232] 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, cis-11-eicosenoic acid-dihydrosphingosine ceramide, stearic acid-dihydrosphingosine ceramide, and arachidic acid-dihydrosphingosine ceramide were 53%, 32%, 8%, 2.5%, 1%, 0.5%, and 0.5%, respectively, with the remainder being other components with low contents.

[0233] In this example, ceramide was synthesized from wheat germ oil fatty acids, phytosphingosine, and sphingosine.

[0234] Example 34 Malania oleifera seed oil ceramide was synthesized from Malania oleifera seed oil fatty acids and phytosphingosine using Example 2. The product was analyzed by HPLC. HPLC chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) was used, and an Innoval ODS-2 4.6*250 mm, 5 μm chromatography column was used. 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.

[0235] The retention times of each component in HPLC were as follows: linoleic acid-phytosphingosine ceramide 9.5 minutes, palmitic acid-phytosphingosine ceramide 10.7 minutes, oleic acid-phytosphingosine ceramide 11.3 minutes, arachidic acid-phytosphingosine ceramide 16.5 minutes, and nervonic acid-phytosphingosine ceramide 22.2 minutes.

[0236] The obtained product was analyzed by high-performance liquid chromatography, and the contents of nervonic 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, with the remainder being other components with low contents.

[0237] In this example, ceramide was synthesized from Malania oleifera seed oil fatty acids, sphingosine, and dihydrosphingosine.

[0238] Example 35 Blackcurrant seed oil ceramide was synthesized from blackcurrant seed oil fatty acids and dihydrosphingosine using Example 2. The product was analyzed by HPLC. HPLC chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) was used, and an Innoval ODS-2 4.6*250 mm, 5 μm chromatography column was used. 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.

[0239] The retention times of each component in HPLC were as follows: linolenic acid-dihydrosphingosine ceramide 8.3 minutes, linoleic acid-dihydrosphingosine ceramide 9.5 minutes, palmitic acid-dihydrosphingosine ceramide 10.6 minutes, oleic acid-dihydrosphingosine ceramide 11.1 minutes, stearic acid-dihydrosphingosine ceramide 13.5 minutes, and arachidic acid-dihydrosphingosine ceramide 16.0 minutes.

[0240] 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, with the remainder being other components with low contents.

[0241] In this example, ceramide was synthesized from blackcurrant seed oil fatty acids, phytosphingosine, and sphingosine.

[0242] Example 36 DHA algal oil ceramide was synthesized from DHA algal oil fatty acids and sphingosine using Example 2. The product was analyzed by HPLC. Chromatography conditions: Shimadzu high-performance liquid chromatograph (LC-2030C 3D Plus) with an Innoval ODS-2 4.6*250mm, 5μm chromatography 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.

[0243] The retention times of each component in HPLC were as follows: linolenic acid-sphingosine ceramide 7.9 minutes, oleic acid-sphingosine ceramide 10.2 minutes, palmitic acid-sphingosine ceramide 10.5 minutes, stearic acid-sphingosine ceramide 13.6 minutes, EPA-sphingosine ceramide 15.6 minutes, arachidic acid-sphingosine ceramide 17.8 minutes, DHA-sphingosine ceramide 19.1 minutes, and behenic acid-sphingosine ceramide 24.0 minutes.

[0244] 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, linoleic 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, with the remainder being other components with low contents.

[0245] In this example, ceramide was synthesized from DHA algal oil fatty acid, phytosphingosine, and dihydrosphingosine.

[0246] The samples used in Examples 37 to 43 all refer to vegetable oil ceramides obtained by reacting the corresponding vegetable oil fatty acids with phytosphingosine; for example, cottonseed oil ceramide refers to the product obtained by reacting cottonseed oil fatty acids with phytosphingosine.

[0247] Example 37 Evaluation of compound cell proliferation activity by MTT method 1 × 10 HaCaT cells 4 Cells were seeded into a 96-well plate at a density of 100 cells / well and cultured overnight in an incubator. After 24 hours, the supernatant was discarded, and 100 μL of medium containing different concentrations of the sample was added. After 24 hours of incubation, the 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 viability (A) was calculated. 投薬ウェル / A ブランクウェル ×100% was calculated.

[0248] As shown in Figure 1, cottonseed oil ceramide, tea oil ceramide, milk thistle oil ceramide, and perilla seed oil ceramide all exhibited cellular activity-promoting effects, stable concentration gradients, significant cell proliferation-promoting effects, and excellent tissue repair capabilities. Among these, cottonseed oil ceramide (Figure 1a) exhibited cell viability of 122.63%, 108.38%, 94.33%, 100.86%, 119.66%, 113.59%, 100.40%, 115.47%, and 124.87% at concentrations of 0.97657, 1.95313, 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, and 250 mg / L, respectively, with an effective concentration of only 1 mg / L. For tea oil ceramide (Figure 1b), the cell viabilities at concentrations of 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, and 250 mg / L were 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. For milk thistle oil ceramide (Figure 1c), the cell viabilities 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. For perilla seed oil ceramide (Figure 1d), the cell viabilities at concentrations of 0.97657, 1.95313, 3.90625, 7.8125, 15.625, 31.25, 62.5, and 125 mg / L were 121.42%, 129.10%, 132.97%, 129.16%, 120.44%, 122.89%, 111.23%, and 118.53%, respectively. The effective concentration was low at 4 mg / L, and the safe concentration was high at 1000 mg / L.

[0249] As shown in Figure 2, ceramides from peony seed oil, borage oil, sea buckthorn seed oil, and Inca inchi oil all exhibited cellular activity-promoting effects, stable concentration gradients, significant cell proliferation-promoting effects, and excellent tissue repair capabilities. Among these, ceramides from peony seed oil (Figure 2a) exhibited cell viability of 109.76%, 106.50%, 107.43%, 105.11%, 105.34%, 107.55%, 116.61%, 124.04%, and 125.96% at concentrations of 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, 250, 500, and 1000 mg / L, respectively. The effective concentration was low at 4 mg / L, while the safe concentration was high at 1000 mg / L. Borage oil ceramide (Figure 2b) induced cell viability of 115.13%, 110.87%, 108.06%, 108.89%, 107.02%, 111.49%, 114.09%, 114.61%, and 122.52% at concentrations of 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, 250, 500, and 1000 mg / L, respectively. The effective concentration was low at 4 mg / L, and the safe concentration was high at 1000 mg / L. For the ceramides of sea buckthorn seed oil (Figure 2c), the cell viabilities 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 low at 4 mg / L, and the safe concentration was high at 1000 mg / L. For Inca inchi oil ceramide (Figure 2d), the cell viabilities at concentrations of 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, 250, 500, and 1000 mg / L 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 low at 4 mg / L, and the safe concentration was high at 1000 mg / L.

[0250] The cell proliferation activity of ceramide 2 was tested using the same method. The cell viabilities 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. Although ceramide 2 had an inhibitory effect on cell proliferation, its potential for tissue repair was inferior to that of vegetable oil ceramide.

[0251] Example 38 Evaluation of skin barrier repair by cell migration Principle: Once the cells have fused to form a monolayer, a blank area is created on the fused monolayer using a scratch tool, and the cells in the blank area are removed by mechanical force. After culturing for a certain period of time, the cells are observed to migrate into the cell-free area, and the migration distance of the cells is measured to evaluate their migration ability.

[0252] Operation steps: 1. Lines were drawn on the culture plate. First, using a marker pen and a ruler, horizontal lines were drawn evenly across the wells on the back of a 6-well plate at intervals of approximately 0.5 to 1 cm. At least five lines were drawn across each well. Care was taken not to make the lines too thick.

[0253] 2. Cells were plated (stained cells). Approximately 5 x 10 cells were plated in the well. 5 The number of cells (which varied depending on the well) was adjusted according to the cell growth rate. The seeding principle was to allow the confluence rate to reach 100% overnight.

[0254] 3. A line was drawn on the cells. On day 2, a scratch was made on the cell layer using a pipette tip, perpendicular to the cell plane, along the line drawn on the underside of the plate on day 1 (it is best to use the same pipette tip between different wells).

[0255] 4. Washing the cells. After scratching was completed, the cells were washed three times with sterile PBS. Cells that were not attached to the wall, i.e., cells in the line created during scratching, were washed away, and the gap left after scratching was clearly visible. Then, the medium was replaced with fresh serum-free medium.

[0256] 5. Cell culture and observation. After diluting the samples with medium (Milk thistle oil ceramide, Perilla seed oil ceramide, Peony seed oil ceramide, Sea pine seed oil ceramide, Borage oil ceramide, Inca inchi oil ceramide at 5 mg / L, Tea oil ceramide, Safflower seed oil ceramide, Cottonseed oil ceramide, Watermelon seed oil ceramide, Pearl jasmine seed oil ceramide, Coconut oil ceramide at 20 mg / L, Ceramide 3B at 100 mg / L), the samples were placed in cell culture dishes and cultured in a 37°C, 5 wt% CO2 incubator. After 24 hours, the cells were removed and observed under a microscope. The scratch width was measured and photographed, and the healing rate was calculated using Image J software.

[0257] As shown in Figure 3, compared to the solvent control group, the scratch widths in the experimental groups were narrower, indicating that milk thistle oil ceramide, perilla seed oil ceramide, peony seed oil ceramide, and sea buckthorn seed oil ceramide have better tissue healing abilities. The healing rate after 24 hours for the solvent control group was 27.33%, while the healing rate after 24 hours for milk thistle oil ceramide (Figure 3a) was 90.23% and the healing rate after 24 hours for ceramide 3B was 59.32%. The healing rate after 24 hours for the solvent control group was 48.35%, while the healing rate after 24 hours for perilla seed oil ceramide (Figure 3b) was 92.41%, and the healing rate after 24 hours for ceramide 3B was 59.32%. The healing rate after 24 hours for the solvent control group was 32.58%, for the Peony Seed Oil Ceramide (Figure 3c) it was 93.21%, and for Ceramide 3B it was 59.32%. The healing rate after 24 hours for the solvent control group was 29.58%, for the Sea Pine Seed Oil Ceramide (Figure 3d) it was 94.26%, and for Ceramide 3B it was 59.32%.

[0258] As shown in Figure 4, compared to the solvent control group, the scratch widths in the experimental groups were narrower, indicating that borage oil ceramide, Inca inchi oil ceramide, tea oil ceramide, and safflower seed oil ceramide have better tissue healing abilities. The healing rate after 24 hours for the solvent control group was 29.58%, while the healing rate after 24 hours for borage oil ceramide (Figure 4a) was 82.31% and the healing rate after 24 hours for ceramide 3B was 59.32%. The healing rate after 24 hours for the solvent control group was 29.58%, while the healing rate after 24 hours for Inca inchi oil ceramide (Figure 4b) was 92.71%, and the healing rate after 24 hours for ceramide 3B was 59.32%. The rate of adhesion after 24 hours for the solvent control group was 34.25%, for the tea oil ceramide (Figure 4c) it was 88.75%, and for ceramide 3B it was 59.32%. The rate of adhesion after 24 hours for the solvent control group was 41.25%, for the safflower seed oil ceramide (Figure 4d) it was 94.25%, and for ceramide 3B it was 59.32%.

[0259] As shown in Figure 5, compared with the solvent control group, the scratch widths in the experimental groups were narrower, indicating that cottonseed oil ceramide, watermelon seed oil ceramide, Chinese laurel seed oil ceramide, and coconut oil ceramide had better tissue healing abilities. The healing rate after 24 hours for the solvent control group was 38.22%, while that for cottonseed oil ceramide (Figure 5a) was 96.21%, and that for ceramide 3B was 59.32%. The healing rate after 24 hours for the solvent control group was 35.21%, while that for watermelon seed oil ceramide (Figure 5b) was 88.53%, and that for ceramide 3B was 59.32%. The 24-hour healing rate for the solvent control group was 31.38%, for the Chinese laurel seed oil ceramide (Figure 5c) it was 87.22%, and for ceramide 3B it was 59.32%. The 24-hour healing rate for the solvent control group was 29.58%, for the coconut oil ceramide (Figure 5d) it was 82.31%, and for ceramide 3B it was 59.32%.

[0260] Therefore, the compound of the present invention obviously enhances the cell healing rate, has good skin tissue repair activity, and has better effect than ceramide 3B.

[0261] Example 39 Anti-aging effect test using elastase inhibition experiment Elastase inhibition method: 2 mL of 2 mg / mL elastase solution was taken, and samples of different concentrations were added. The mixture was thoroughly vortexed to mix uniformly. The mixture was shaken at 37°C and 400 r / min on a shaker for 20 minutes. 5 mL of 0.5 mol / L phosphate buffer solution at pH 6.0 was immediately added, and the mixture was vortexed to mix uniformly. An appropriate amount of the uniformly mixed solution was placed in a 2 mL centrifuge tube and centrifuged at 9,391 × g for 10 minutes. 200 μL of the supernatant was precisely aspirated and placed in a 96-well plate. The absorbance was measured at a wavelength of 495 nm using a microplate reader, and a spectral scan was simultaneously performed from 400 to 800 nm.

[0262] A solution containing the enzyme added to the substrate served as the blank control, a solution containing the enzyme and sample added to the substrate served as the enzyme inhibition group, and a solution containing the sample added to the substrate but no enzyme was used for background subtraction. Each group consisted of three replicate wells. The inhibition rate (%) = [1-(An-An') / (A0-A0')] × 100%, where A0 is the absorbance of the solution containing the enzyme but no sample, A0' is the absorbance of the solution containing only the substrate but no sample or enzyme, An is the absorbance of the solution containing only the sample, and An' is the absorbance of the solution containing the sample but no enzyme. If An' > An, a promotion effect was indicated, and the promotion rate (%) = [1-(An'-An) / (A0-A0')] × 100%.

[0263] The results, as shown in Figures 6 to 8 and the table below, showed that the compounds of the present invention had good inhibitory effects on elastase at all different concentrations, but the inhibitory effect of ceramide 2 was not as great as that of vegetable oil ceramide at the same concentration. JPEG2025536776000006.jpg68170 (Example 40) Evaluation of anti-inflammatory and repair effects using LPS-induced cell methods B16 mouse melanoma cells were grown at a density of 1 x 10 4 Cells were seeded into a 96-well plate at 100 μL per well and cultured overnight in an incubator to allow the cells to adhere to the wall. After 24 hours, the supernatant was discarded and 100 μL of samples diluted with DMEM medium at different concentrations was added. A negative control group contained DMEM medium without sample. Each group had three duplicate wells and was incubated in an environment of 5 wt% CO2 and 37°C. Two hours after administration, 10 μg / mL LPS was added to the lipopolysaccharide model group and experimental group, and the cells were incubated together for 24 hours. After the reaction was completed, 50 μL of the cell supernatant was taken and intracellular IL-6 gene expression was measured using an IL-6 ELISA kit.

[0264] As shown in Figure 9a, under stimulation with 10 μg / mL LPS, IL-6 levels were 10.95 times the baseline level. Under the influence of rapeseed oil ceramide at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, IL-6 levels were significantly reduced to 0.87, 0.64, 0.52, and 0.16 times those in the LPS model group, respectively, in a dose-dependent manner. As shown in Figure 9b, under stimulation with 10 μg / mL LPS, IL-6 levels were 10.16 times the baseline level. Under the influence of milk thistle oil ceramide at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, IL-6 levels were significantly reduced to 0.70, 0.45, 0.27, and 0.09 times those in the LPS model group, respectively, in a dose-dependent manner. As shown in Figure 9c, under stimulation with 10 μg / mL LPS, IL-6 levels were 10.16-fold higher than baseline. Under the influence of 50, 100, 200, and 400 mg / L perilla seed oil ceramide, IL-6 levels were significantly reduced to 0.89, 0.66, 0.59, and 0.25-fold lower than the LPS control group, respectively, in a dose-dependent manner. As shown in Figure 9d, under stimulation with 10 μg / mL LPS, IL-6 levels were 11.51-fold higher than baseline. Under the influence of 50, 100, 200, and 400 mg / L sunflower seed oil ceramide, IL-6 levels were significantly reduced to 0.84, 0.68, 0.52, and 0.31-fold lower than the LPS control group, respectively, in a dose-dependent manner.

[0265] As shown in Figure 10a, under stimulation with 10 μg / mL LPS, IL-6 levels were 10.16-fold higher than baseline. Under the influence of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L peony seed oil ceramide, IL-6 levels were significantly reduced to 0.99, 0.74, 0.48, and 0.22-fold lower than the LPS control group, respectively, in a dose-dependent manner. As shown in Figure 10b, under stimulation with 10 μg / mL LPS, IL-6 levels were 10.16-fold higher than baseline. Under the influence of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L safflower seed oil ceramide, IL-6 levels were significantly reduced to 0.94, 0.69, 0.56, and 0.22-fold lower than the LPS control group, respectively, in a dose-dependent manner. As shown in Figure 10c, under LPS stimulation at a concentration of 10 μg / mL, IL-6 levels were 10.16-fold higher than baseline. Under the influence of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L of sea buckthorn seed oil ceramide, IL-6 levels were significantly reduced to 0.99, 0.74, 0.53, and 0.27-fold lower than those in the LPS model group, respectively, in a dose-dependent manner. As shown in Figure 10d, under LPS stimulation at a concentration of 10 μg / mL, IL-6 levels were 10.16-fold higher than baseline. Under the influence of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L of walnut oil ceramide, IL-6 levels were significantly reduced to 0.84, 0.66, 0.45, and 0.25-fold lower than those in the LPS model group, respectively, in a dose-dependent manner.

[0266] As shown in Figure 11a, under stimulation with LPS at a concentration of 10 μg / mL, IL-6 levels were 10.16-fold higher than baseline. Under the influence of inca inchi oil ceramide at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, IL-6 levels were significantly reduced to 0.84, 0.63, 0.40, and 0.14-fold, respectively, compared to the LPS model group, demonstrating dose-dependent effects. As shown in Figure 11b, under stimulation with LPS at a concentration of 10 μg / mL, IL-6 levels were 10.16-fold higher than baseline. Under the influence of borage oil ceramide at concentrations of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L, IL-6 levels were significantly reduced to 0.84, 0.58, 0.43, and 0.17-fold, respectively, compared to the LPS model group, demonstrating dose-dependent effects. As shown in Figure 11c, under stimulation with 10 μg / mL LPS, IL-6 levels were 10.16-fold higher than baseline. Under the influence of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L grape seed oil ceramide, IL-6 levels were significantly reduced to 0.99, 0.79, 0.53, and 0.33-fold lower than those in the LPS control group, respectively, in a dose-dependent manner. As shown in Figure 11d, under stimulation with 10 μg / mL LPS, IL-6 levels were 10.16-fold higher than baseline. Under the influence of 50 mg / L, 100 mg / L, 200 mg / L, and 400 mg / L prickly pear seed oil ceramide, IL-6 levels were significantly reduced to 0.99, 0.74, 0.53, and 0.27-fold lower than those in the LPS control group, respectively, in a dose-dependent manner.

[0267] Therefore, the plant oil ceramide of the present invention has a good anti-inflammatory effect and can promote the repair of skin damaged by inflammation.

[0268] Example 41 MMP1, also known as interstitial collagenase or matrix metalloproteinase, belongs to the matrix metalloproteinase family. Its main substrate is fibrillar collagen. It can degrade collagen fibers and gelatin in the extracellular matrix, altering the cellular microenvironment. MMP1 plays an important role in elastin synthesis. Inhibition of MMP1 can promote collagen and elastin synthesis in fibroblasts, and reduced MMP activity can increase the rate of collagen synthesis.

[0269] 1 × 10 HaCaT cells 5 Cells were seeded into a 96-well plate at a density of 100 cells / well and cultured overnight in an incubator. After 24 hours, the supernatant was discarded, and 100 μL of medium containing different concentrations of samples was added. No sample was added to the model group, and the negative control group contained DMEM medium without any sample. Each group had three duplicate wells. After 2 hours of incubation in an environment of 5% CO2 and 37°C, they were irradiated with UVA or UVB. The distance between the UV irradiation light source and the cells was 15 cm, and the UVA intensity was 200 mJ / cm. 2 The irradiation time was 2 hours and the UVB intensity was 50 mJ / cm 2 The irradiation time was 1 hour. After irradiation, the cells were incubated in an incubator for 12 hours. The expression of the MMP-1 gene in the cells was measured using an MMP-1 ELISA kit. Inhibition rate = 1 - (MMP1 expression level in the experimental group / MMP1 expression level in the model group) x 100%.

[0270] As shown in Figure 12, for UVA, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 1.90, and the MMP1 expression inhibition rates for the model group were 34%, 51%, and 69% at concentrations of 125, 250, and 400 mg / L of milk thistle oil ceramide (Figure 12a). For UVB, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 2.33, and the MMP1 expression inhibition rates for the model group were 44%, 52%, and 65% at concentrations of 125, 250, and 400 mg / L of milk thistle oil ceramide (Figure 12b). For UVA, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 1.90, and the MMP1 expression inhibition rates for the model group were 39%, 47%, and 64% at concentrations of 125, 250, and 400 mg / L of linseed oil ceramide (Figure 12c).For UVB, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 2.33, and the MMP1 expression inhibition rates for the model group were 38%, 48%, and 67% at concentrations of 125, 250, and 400 mg / L of linseed oil ceramide (Figure 12d).

[0271] As shown in Figure 13, for UVA, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 1.90, and the MMP1 expression inhibition rates for the model group were 35%, 49%, and 67% at concentrations of 125, 250, and 400 mg / L of peony seed oil ceramide (Figure 13a).For UVB, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 2.33, and the MMP1 expression inhibition rates for the model group were 40%, 51%, and 63% at concentrations of 125, 250, and 400 mg / L of peony seed oil ceramide (Figure 13b). For UVA, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 1.90, and the MMP1 expression inhibition rates for the model group were 42%, 62%, and 81% at concentrations of 125, 250, and 400 mg / L of tomato seed oil ceramide (Figure 13c).For UVB, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 2.33, and the MMP1 expression inhibition rates for the model group were 39%, 49%, and 69% at concentrations of 125, 250, and 400 mg / L of tomato seed oil ceramide (Figure 13d).

[0272] As shown in Figure 14, for UVA, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 1.90, and the MMP1 expression inhibition rates for the model group were 35%, 50%, and 62% at concentrations of 125, 250, and 400 mg / L of Oriental Pine Seed Oil Ceramide (Figure 14a). For UVB, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 2.33, and the MMP1 expression inhibition rates for the model group were 30%, 53%, and 67% at concentrations of 125, 250, and 400 mg / L of Oriental Pine Seed Oil Ceramide (Figure 14b). For UVA, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 1.90, and at concentrations of 125, 250, and 400 mg / L, coconut oil ceramide (Figure 14c) inhibited MMP1 expression by 31%, 49%, and 67% compared to the model group. For UVB, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 2.33, and at concentrations of 125, 250, and 400 mg / L, coconut oil ceramide (Figure 14d) inhibited MMP1 expression by 38%, 58%, and 74% compared to the model group.

[0273] As shown in Figure 15, for UVA, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 1.90. Cottonseed oil (Figure 15a) at concentrations of 125, 250, and 400 mg / L suppressed MMP1 expression by 27%, 48%, and 62% compared to the model group. For UVB, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 2.33. Cottonseed oil (Figure 15b) at concentrations of 125, 250, and 400 mg / L suppressed MMP1 expression by 35%, 49%, and 56% compared to the model group. For UVA, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 1.90. Sea buckthorn oil ceramide (Figure 15c) at concentrations of 125, 250, and 400 mg / L suppressed MMP1 expression by 31%, 46%, and 56% compared to the model group. For UVB, if the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 2.33, and the MMP1 expression inhibition rates for the model group were 35%, 51%, and 69% at concentrations of 125, 250, and 400 mg / L for sea buckthorn oil ceramide (Figure 15d).

[0274] As shown in Figure 16, for UVA, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 1.90, and the MMP1 expression inhibition rates for the model group were 34%, 44%, and 56% at concentrations of 125, 250, and 400 mg / L of argan oil ceramide (Figure 16a).For UVB, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 2.33, and the MMP1 expression inhibition rates for the model group were 40%, 52%, and 67% at concentrations of 125, 250, and 400 mg / L of argan oil ceramide (Figure 16b). For UVA, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 1.90, and wheat germ oil ceramide (Figure 16c) at concentrations of 125, 250, and 400 mg / L suppressed MMP1 expression by 38%, 61%, and 67% compared to the model group. For UVB, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 2.33, and wheat germ oil ceramide (Figure 16d) at concentrations of 125, 250, and 400 mg / L suppressed MMP1 expression by 43%, 48%, and 68% compared to the model group.

[0275] As shown in Figure 17, for UVA, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 1.90, and the MMP1 expression inhibition rates relative to the model group were 38%, 51%, and 67% at concentrations of 125, 250, and 400 mg / L of prune seed oil ceramide (Figure 17a).For UVB, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 2.33, and the MMP1 expression inhibition rates relative to the model group were 43%, 48%, and 68% at concentrations of 125, 250, and 400 mg / L of prune seed oil ceramide (Figure 17b). For UVA, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 1.90, and at concentrations of 125, 250, and 400 mg / L, hazelnut oil ceramide (Figure 17c) inhibited MMP1 expression by 29%, 44%, and 62% compared to the model group. For UVB, when the MMP1 expression level in the negative control group was set to 1, the expression level in the model group was 2.33, and at concentrations of 125, 250, and 400 mg / L, hazelnut oil ceramide (Figure 17d) inhibited MMP1 expression by 35%, 50%, and 68% compared to the model group.

[0276] After UVA irradiation, keratinocytes promoted increased MMP1 expression in fibroblasts, which led to the degradation of the extracellular matrix and collagen, causing skin photoaging. As can be seen from the above results, vegetable oil ceramides can inhibit UV-induced MMP1 production in fibroblasts, playing a role in preventing skin photoaging.

[0277] Example 42 Evaluation of antioxidant performance by scavenging DPPH free radicals DPPH is 1,1-diphenyl-2-picrylhydrazyl and can be used in antioxidant experiments.

[0278] Samples of the corresponding concentrations (50, 100, 200, 400, and 800 mg / L) were mixed uniformly with 0.1 mol / L DPPH and absolute ethanol solutions at a 1:1 volume ratio. DPPH and absolute ethanol were mixed at equal volumes at room temperature for 30 minutes in the dark, and the absorbance was measured at 517 nm. The absorbance of the sample-DPPH reaction solution was designated A1, the absorbance of the sample-absorbent ethanol reaction solution was designated A2, and the absorbance of the DPPH-absorbent ethanol reaction solution was designated A3. The DPPH removal rate of the sample = [1-(A1-A2) / A3] x 100%.

[0279] 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, and 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%, 29.60%, and 33.16%, respectively. As shown in Figure 18c, the DPPH free 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 free radical scavenging rates of nut 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.

[0280] As shown in Figure 19a, the DPPH free 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 free 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 free 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 free radical scavenging rates of prickly pear seed oil ceramide were 13.43%, 24.32%, 35.10%, 39.00%, and 45.57% at concentrations of 50, 100, 200, 400, and 800 mg / L, respectively.

[0281] As shown in Figure 20a, the DPPH free 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 free 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 free 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 free 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.

[0282] As shown in Figure 21a, the DPPH free 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 free radical scavenging rates of sunflower seed 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 free radical scavenging rates of DHA algal 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 free 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.

[0283] Therefore, the vegetable oil ceramide of the present invention has a higher DPPH removal rate than ceramide 3B and has a better antioxidant effect.

[0284] Example 43 Whitening activity test B16 cells in the exponential growth phase were digested with 0.25% trypsin-EDTA, blown to homogenize, and then diluted to 3 × 10 5Cells were seeded into 12-well plates at a density of 100 cells / well and cultured overnight at 37°C in 5% CO2. The supernatant was discarded, and medium containing different concentrations of sample was added. A blank group was incubated in RPMI-1640 medium without sample, and a model group was incubated in medium supplemented with DMEM. Each group contained three duplicate wells, and the wells were incubated for 24 hours at 5% CO2 and 37°C. The medium was discarded from the well plate, and the wells were washed once or twice with phosphate buffered saline (PBS). Cells were lysed by adding 1 mL of 1 mol / L NaOH solution containing 10% DMSO. The plate was then incubated at 80°C or 100°C for 2 hours until the cells were completely lysed. The plate was then placed in a microplate reader and the absorbance was measured at 405 nm. The melanin inhibition rate = 1 - (OD value of each well / OD value of model group) x 100%.

[0285] As shown in Figure 22a, when the melanin content of the blank control group was set to 1, the melanin expression of the model group was 1.54, and when the concentrations of evening primrose oil ceramide were 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates were 20.08%, 21.12%, 24.33%, 33.03%, and 42.26%, respectively. As shown in Figure 22b, when the melanin content of the blank control group was set to 1, the melanin expression of the model group was 1.51, and when the concentrations of shea butter ceramide were 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates were 8.14%, 14.73%, 22.21%, 27.79%, and 38.33%, respectively. As shown in Figure 22c, when the melanin content of the blank control group was set to 1, the melanin expression of the model group was 1.54. At concentrations of 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of milk thistle oil ceramide were 22.24%, 23.28%, 26.49%, 37.36%, and 44.85%, respectively. As shown in Figure 22d, when the melanin content of the blank control group was set to 1, the melanin expression of the model 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.

[0286] As shown in Figure 23a, when the melanin content of the blank control group was set to 1, the melanin expression of the model 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, when the melanin content of the blank control group was set to 1, the melanin expression of the model group was 1.54. At concentrations of 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of yuanbao jasmine seed oil ceramide were 22.24%, 34.10%, 39.48%, 46.02%, and 51.35%, respectively. As shown in Figure 23c, when the melanin content of the blank control group was set to 1, the melanin expression of the model group was 1.51. At concentrations of 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of Inca inchi oil ceramide were 16.54%, 25.79%, 28.85%, 34.43%, and 42.75%, respectively. As shown in Figure 23d, when the melanin content of the blank control group was set to 1, the melanin expression of the model group was 1.51. At concentrations of 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates of rosehip oil ceramide were 11.68%, 19.15%, 25.53%, 27.79%, and 40.54%, respectively.

[0287] As shown in Figure 24a, when the melanin content of the blank control group was set to 1, the melanin expression of the model group was 1.51, and the melanin inhibition rates of grape seed oil ceramide at concentrations of 10, 20, 40, 80, and 100 mg / L were 17.43%, 19.15%, 26.64%, 32.22%, and 44.96%, respectively. As shown in Figure 24b, when the melanin content of the blank control group was set to 1, the melanin expression of the model group was 1.54, and the melanin inhibition rates of sea buckthorn oil ceramide at concentrations of 10, 20, 40, 80, and 100 mg / L were 15.10%, 21.55%, 24.98%, 35.20%, and 46.59%, respectively. As shown in Figure 24c, when the melanin content of the blank control group was set to 1, the melanin expression of the model group was 1.54, and when the concentrations of argan oil ceramide were 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates were 17.91%, 18.95%, 22.16%, 30.87%, and 39.66%, respectively. As shown in Figure 24d, when the melanin content of the blank control group was set to 1, the melanin expression of the model group was 1.54, and when the concentrations of marula oil ceramide were 10, 20, 40, 80, and 100 mg / L, the melanin inhibition rates were 15.53%, 22.42%, 30.82%, 40.39%, and 47.02%, respectively.

[0288] Therefore, the vegetable oil ceramide of the present invention exhibits excellent whitening effects.

[0289] The above are only specific embodiments of the present invention, and the scope of protection of the present invention is not limited thereto. Any modifications or conversions that are easily conceivable by a person skilled in the art within the technical scope disclosed in the present invention should be included within the scope of protection of the present invention. Therefore, the scope of protection of the present invention is based on the scope specified in the claims.

Claims

1. The vegetable oil ceramide is obtained by reacting a vegetable oil fatty acid with a sphingosine compound, and the vegetable oil fatty acid is selected from the group consisting of 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, Inca inchi oil fatty acid, watermelon seed oil fatty acid, coconut oil fatty acid, Chinese quince seed oil fatty acid, walnut oil fatty acid, avocado oil fatty acid, tomato seed oil fatty acid, sea buckthorn seed oil fatty acid, blue thorn fruit oil fatty acid, safflower seed oil fatty acid, peony seed oil fatty acid, sunflower seed oil fatty acid, perilla seed oil fatty acid, and linseed oil. A vegetable oil ceramide characterized in that the vegetable oil ceramide is at least one selected from 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, meadowfoam seed oil fatty acids, baobab seed oil fatty acids, prickly pear seed oil fatty acids, wheat germ oil fatty acids, sesame oil fatty acids, corn oil fatty acids, almond oil fatty acids, Malania oleifera seed oil fatty acids, peanut oil fatty acids, blackcurrant seed oil fatty acids, rapeseed oil fatty acids, hazelnut oil fatty acids, pumpkin seed oil fatty acids, DHA algae oil fatty acids, Calophyllum indicum seed oil fatty acids, kiwi seed oil fatty acids, marula oil fatty acids, and prune seed oil fatty acids.

2. 2. The vegetable oil ceramide according to claim 1, wherein the sphingosine-based compound is at least one selected from the group consisting of sphingosine, phytosphingosine, and dihydrosphingosine.

3. 2. The vegetable oil ceramide of claim 1, wherein the vegetable oil fatty acid is obtained by hydrolysis of vegetable oil.

4. The composition of the olive oil fatty acids is 20-83 wt% oleic acid, 7.5-20 wt% palmitic acid, 3.5-70 wt% linoleic acid, 0.5-5 wt% stearic acid, 0.1-1.0 wt% linolenic acid, 0-3.5 wt% palmitoleic acid, 0-0.6 wt% arachidic acid, 0-0.4 wt% eicosenoic acid, 0-0.3 wt% heptadecanoic acid, 0-0.3 wt% heptadecenoic acid, 0-0.2 wt% behenic acid, 0-0.2 wt% lignoceric acid, and 0-0.05 wt% myristic acid, and the composition of the tea oil fatty acids is 75-90 wt% oleic acid, 2- 15 wt% linoleic acid, 1 to 10 wt% palmitic acid, 0.1 to 3 wt% stearic acid, 0.01 to 1 wt% linolenic acid, and 0 to 0.5 wt% arachidic acid; the composition of the sea buckthorn oil fatty acids is 20 to 35 wt% oleic acid, 8 to 30 wt% palmitic acid, 4 to 40 wt% linoleic acid, 2 to 30 wt% linolenic acid, 0.5 to 35 wt% palmitoleic acid, 0.5 to 3 wt% stearic acid, and 0 to 1 wt% myristic acid; and the composition of the grape seed oil fatty acids is 55 to 85 wt% linoleic acid, 8 to 25 wt% oleic acid, and 1 to 12 wt% palmitic acid. 0.5-7 wt% stearic acid, 0.01-2 wt% palmitoleic acid, 0.01-1 wt% linolenic acid, and 0-1 wt% arachidic acid, and the composition of the nut oil fatty acids is 55-80 wt% oleic acid, 12-35 wt% palmitoleic acid, 2-10 wt% palmitic acid, 0.4-3 wt% linoleic acid, 0.1-3 wt% arachidic acid, 0.2-5 wt% stearic acid, 0.01-1 wt% linolenic acid, 0.01-1 wt% behenic acid, 0-1.5 wt% myristic acid, and 0-3 wt% cis-11-eicosenoic acid, and the composition of the borage oil fatty acids is 55-80 wt% oleic acid, 12-35 wt% palmitoleic acid, 2-10 wt% palmitic acid, 0.4-3 wt% linoleic acid, 0.1-3 wt% arachidic acid, 0.2-5 wt% stearic acid, 0.01-1 wt% linolenic acid, 0.01-1 wt% behenic acid, 0-1.5 wt% myristic acid, and 0-3 wt% cis-11-eicosenoic acid. The composition is 20-40 wt% gamma-linolenic acid, 30-45 wt% linoleic acid, 15-25 wt% oleic acid, 2-8 wt% palmitic acid, 1-5 wt% stearic acid, 0-2 wt% arachidic acid, 0-2 wt% cis-11-eicosenoic acid, and 0-2 wt% erucic acid, and the composition of the rosehip oil fatty acids is 30-60 wt% linoleic acid, 20-45 wt% linolenic acid, 6-25 wt% oleic acid, 0.1-3 wt% stearic acid, 0.5-5 wt% palmitic acid, 0.01-1 wt% arachidic acid, and 0-1 wt% cis-11-eicosenoic acid,The soybean oil fatty acid has a composition of 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. The rice bran oil fatty acid has a composition of 40-60 wt% oleic acid, 20-45 wt% linoleic acid, 5-20 wt% palmitic acid, 0.5-5 wt% stearic acid, 0.1-2 wt% linolenic acid, and 0-2 wt% arachidic acid. The cottonseed oil fatty acid has a composition of 55-80 wt% linoleic acid, 10-25 wt% palmitic acid, and 0-25 wt% behenic acid. the composition of the fatty acids of the Inca inchi oil is 45-68 wt% linolenic acid, 20-40 wt% linoleic acid, 5-12 wt% oleic acid, 2-5 wt% palmitic acid, and 1-4 wt% stearic acid; the composition of the fatty acids of the watermelon seed oil is 60-80 wt% linoleic acid, 3-15 wt% palmitic acid, 10-30 wt% oleic acid, and 1-5 wt% stearic acid; The composition of the coconut oil fatty acids is 20-70 wt% lauric acid, 10-50 wt% myristic acid, 10-20 wt% palmitic acid, 2-10 wt% stearic acid, 2-10 wt% oleic acid, 0-3 wt% capric acid, and 0-3 wt% caproic acid. The composition of the walnut oil fatty acids is 25-48 wt% linoleic acid, 20-40 wt% oleic acid, 5-30 wt% arachidic acid, 4-15 wt% cis-11-eicosenoic acid, 0.5-5 wt% linolenic acid, 0.1-5 wt% palmitic acid, and 0.1-4 wt% stearic acid. The fatty acid composition is 40-75 wt% linoleic acid, 15-50 wt% oleic acid, 2-10 wt% palmitic acid, 0-5 wt% linolenic acid, and 0-4 wt% stearic acid. The avocado oil fatty acid composition is 50-80 wt% oleic acid, 5-25 wt% palmitoleic acid, 5-20 wt% linoleic acid, 6-18 wt% palmitic acid, 0.1-2 wt% stearic acid, 0.1-1 wt% linolenic acid, 0-1 wt% arachidic acid, and 0-0.5 wt% cis-11-eicosenoic acid. The tomato seed oil fatty acid composition is 55-80 wt% linoleic acid,The fatty acid composition of the sea buckthorn seed oil is 10-25 wt% oleic acid, 3-20 wt% palmitic acid, 1-8 wt% stearic acid, 0.2-2 wt% linolenic acid, and 0-1 wt% arachidic acid, and the fatty acid composition of the sea buckthorn seed oil is 50-75 wt% oleic acid, 15-40 wt% linolenic acid, 0.5-10 wt% stearic acid, 0-15 wt% ximenynic acid, 0-15 wt% nervonic acid, 0-2 wt% behenic acid, 0-1 wt% palmitic acid, and 0-1 wt% linoleic acid, and the fatty acid composition of the blue thorn fruit oil is 30-50 wt% linoleic acid, 25-40 wt% oleic acid, 10-25 wt% arachidic ... sea buckthorn seed oil is 50-75 wt% oleic acid, 15-40 wt% linolenic acid, 0.5-10 wt% stearic acid, 0-15 wt% ximenynic acid, 0-15 wt% nervonic acid, 0-2 wt% behenic acid, 0-15 wt% palmitic acid, and 0-1 wt% linoleic acid. % palmitic acid, 3-10 wt% stearic acid, 0-1 wt% palmitoleic acid, and 0-1 wt% arachidic acid, and the composition of the fatty acids in the 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, and the composition of the fatty acids in the peony seed oil is 35-70 wt% α-linolenic acid, 15-40 wt% linoleic acid, 10-30 wt% oleic acid, 0.1-5 wt% palmitic acid, 0.1-5 wt% stearic acid, and 0-1 wt% arachidic acid. The composition of the sunflower seed oil fatty acids is 55-75 wt% linoleic acid, 20-40 wt% oleic acid, 0.5-7 wt% stearic acid, 1-8 wt% palmitic acid, 0-2 wt% behenic acid, and 0-1 wt% arachidic acid. The composition of the perilla seed oil fatty acids is 65-90 wt% α-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% cis-11-eicosenoic acid. The composition of the flaxseed oil fatty acids is 40-70 wt% 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% cis-11-eicosenoic acid. the composition of the milk thistle oil fatty acids is 50-75 wt% linoleic acid, 15-45 wt% oleic acid, 1-10 wt% palmitic acid, 1-6 wt% stearic acid, 0.2-4 wt% arachidic acid, 0.5-4 wt% behenic acid, 0.01-2.5 wt% linolenic acid, 0-1.5 wt% myristic acid; and the composition of the shea butter fatty acids is 35-60 wt% oleic acid, 25-55 wt% stearic acid,2-10 wt% linoleic acid, 0.5-10 wt% palmitic acid, 0.1-2 wt% arachidic acid, 0-1 wt% linolenic acid, and 0-1 wt% behenic acid; the composition of the evening primrose oil fatty acids is 55-88 wt% linoleic acid, 3-20 wt% oleic acid, 5-20 wt% γ-linolenic acid, 0.5-5 wt% palmitic acid, 0-2 wt% stearic acid, 0-2 wt% cis-11-eicosenoic acid, and 0-1 wt% behenic acid; and the composition of the argan oil fatty acids is 35-50 wt% oleic acid, 30-50 wt% linoleic acid, 5-15 wt% palmitic acid, and 2- 8 wt% stearic acid, 0.1-1 wt% arachidic acid, 0.01-0.5 wt% linoleic acid, 0-0.5 wt% behenic acid, and 0-0.5 wt% cis-11-eicosenoic acid; the composition of the hemp seed oil fatty acids is 50-75 wt% linoleic acid, 5-30 wt% linolenic acid, 5-20 wt% oleic acid, 3-15 wt% palmitic acid, and 1-5 wt% stearic acid; and the composition of the meadowfoam seed oil fatty acids is 50-80 wt% cis-5-eicosenoic acid, 8-25 wt% cis-5,13-docosadienoic acid, 5-20 wt% erucic acid, and 1-1 and the composition of the fatty acids in the baobab seed oil is 30-50 wt% oleic acid, 15-35 wt% linoleic acid, 13-30 wt% palmitic acid, 2-8 wt% stearic acid, 0.5-5 wt% linolenic acid, 0.2-2 wt% arachidic acid, 0-1 wt% palmitoleic acid, and 0-0.5 wt% myristic acid. The composition of the fatty acids in the prickly pear seed oil is 50-75 wt% linolenic acid, 10-30 wt% oleic acid, 5-15 wt% palmitoleic acid, 3- 10 wt% palmitic acid, 3-8 wt% stearic acid, and 0.1-1 wt% arachidic acid; the wheat germ oil fatty acid has a composition of 50-75 wt% linoleic acid, 15-45 wt% oleic acid, 2-10 wt% palmitic acid, 1-8 wt% linolenic acid, 0.1-1 wt% cis-11-eicosenoic acid, 0-0.5 wt% stearic acid, and 0-0.5 wt% arachidic acid; the sesame oil fatty acid has a composition of 45-70 wt% linoleic acid, 15-35 wt% oleic acid, 6-20 wt% palmitic acid, 0-2 wt% stearic acid, and 0-1 wt% arachidic acid;and 0-0.5 wt% linolenic acid, the composition of the corn oil fatty acid is 50-70 wt% linoleic acid, 20-35 wt% oleic acid, 5-18 wt% palmitic acid, 0.5-3 wt% stearic acid, 0.01-1 wt% linolenic acid, and 0-1 wt% arachidic acid, the composition of the almond oil fatty acid 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, and the composition of the Malania oleifera seed oil fatty acid is 40-60 wt% nervonic acid, The composition of the peanut oil fatty acids is 30-50 wt% oleic acid, 5-12 wt% arachidic acid, 0-2 wt% palmitic acid, and 0-2 wt% linoleic acid, and the composition of the blackcurrant seed oil fatty acids is 40-60 wt% linoleic acid, 30-50 wt% oleic acid, 4-12 wt% palmitic acid, 0.5-5 wt% stearic acid, 0-1 wt% arachidic acid, and 0-1 wt% behenic acid, and the composition of the blackcurrant seed oil fatty acids is 40-60 wt% linoleic acid, 20-40 wt% linolenic acid, 10-20 wt% oleic acid, 1-8 wt% palmitic acid, 0-2 wt% stearic acid, and 0-2 wt% arachidic acid. The rapeseed oil fatty acid has a composition of 50 to 80 wt% oleic acid, 10 to 30 wt% linoleic acid, 2 to 8 wt% linolenic acid, 1 to 5 wt% stearic acid, 0.5 to 5 wt% palmitic acid, 0 to 1 wt% arachidic acid, 0 to 1 wt% cis-11-eicosenoic acid, and 0 to 1 wt% erucic acid, and the hazelnut oil fatty acid has a composition of 70 to 90 wt% oleic acid, 8 to 25 wt% linoleic acid, 0.5 to 5 wt% palmitic acid, 0.5 to 4 wt% stearic acid, 0 to 0.5 wt% linolenic acid, and 0 to 0.5 wt% palmitoleic acid. The composition of the algal seed oil fatty acids 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, and 0-0.5 wt% palmitoleic acid, and the composition of the DHA algal oil fatty acids 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, 0.01-0.5 wt% linolenic acid, 0-0.5 wt% arachidic acid, and 0-0.5 wt% behenic acid.The composition of the fatty acids of Calophyllum tuberosum seed oil is 30 to 50 wt% oleic acid, 15 to 40 wt% linoleic acid, 8 to 20 wt% stearic acid, 6 to 20 wt% palmitic acid, 0.2 to 1.5 wt% arachidic acid, 0.05 to 2 wt% linolenic acid, 0.05 to 1 wt% palmitoleic acid, 0 to 1 wt% behenic acid, 0 to 0.5 wt% cis-11-ene, The fatty acid content of the kiwi 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, and the fatty acid content of the marula oil is 65-85 wt% oleic acid, 5-15 wt% palmitic acid, 2-10 wt% linoleic acid, 2-10 wt% stearic acid, and 0.2-2 wt% stearic acid.

2. The vegetable oil ceramide according to claim 1, wherein the vegetable oil ceramide is composed of 60-80 wt% arachidic acid, 0-1 wt% cis-11-eicosenoic acid, and 0-0.5 wt% linolenic acid, and the prune seed oil fatty acid composition is 60-80 wt% oleic acid, 10-30 wt% linoleic acid, 0.5-5 wt% stearic acid, 0.5-3 wt% palmitoleic acid, 0-7 wt% palmitic acid, and 0-1 wt% linolenic acid.

5. The vegetable oil ceramide is at least two selected from oleic acid ceramide, linoleic acid ceramide, palmitic acid ceramide, linolenic acid ceramide, stearic acid ceramide, palmitoleic acid ceramide, arachidic acid ceramide, cis-11-eicosenoic acid ceramide, behenic acid ceramide, erucic acid ceramide, myristic acid ceramide, nervonic acid ceramide, lauric acid ceramide, eicosenoic acid ceramide, heptadecanoic acid ceramide, heptadecenoic acid ceramide, lignoceric acid ceramide, DHA ceramide, EPA ceramide, capric acid ceramide, caproic acid ceramide, xymenynic acid ceramide, cis-5-eicosenoic acid ceramide, cis-5,13-docosadienoic acid ceramide, and cis-5-docosenoic acid ceramide.

6. 90 wt% or less oleic acid ceramide, 90 wt% or less linoleic acid ceramide, 30 wt% or less palmitic acid ceramide, 90 wt% or less linolenic acid ceramide, 55 wt% or less stearic acid ceramide, 35 wt% or less palmitoleic acid ceramide, 30 wt% or less arachidic acid ceramide, 15 wt% or less cis-11-eicosenoic acid ceramide, 4 wt% or less behenic acid ceramide, 20 wt% or less erucic acid ceramide, 50 wt% or less myristic acid ceramide, 60 wt% or less nervonic acid ceramide, 70 wt% or less lauric acid ceramide, 0.4 wt% or less eicosenoic acid ceramide 6. The vegetable oil ceramide according to claim 5, wherein the vegetable oil ceramide is at least two selected from the group consisting of cis-5-eicosenoic acid ceramide, 0.3 wt% or less heptadecanoic acid ceramide, 0.3 wt% or less heptadecenoic acid ceramide, 0.2 wt% or less lignoceric acid ceramide, 75 wt% or less DHA ceramide, 1 wt% or less EPA ceramide, 3 wt% or less capric acid ceramide, 3 wt% or less caproic acid ceramide, 15 wt% or less ximenynic acid ceramide, 80 wt% or less cis-5-eicosenoic acid ceramide, 25 wt% or less cis-5,13-docosadienoic acid ceramide, and 10 wt% or less cis-5-docosenoic acid ceramide.

7. A method for synthesizing the vegetable oil ceramide according to any one of claims 1 to 6, comprising the steps of: A vegetable oil fatty acid is reacted with a sphingosine compound in the presence of a condensing agent and an organic base, the condensing agent being DCC or EDCI, and the organic base being DMAP, DIPEA, NMM, or Et ３ N, the molar ratio of the vegetable oil fatty acid, the sphingosine compound, the condensing agent, and the organic base is 1:(1-1.5):(1-2):(0.2-2), and the reaction solvent is at least one of dichloromethane, tetrahydrofuran, ethyl acetate, and acetonitrile.

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

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

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