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Kojic acid and kojic acid derivatives, preparation method and application thereof

A technology of kojic acid and medicine, which is applied in the field of kojic acid and kojic acid derivatives and their anti-inflammatory applications, and can solve the problems of less research reports on the anti-inflammatory activity of kojic acid and its derivatives

Active Publication Date: 2022-07-05
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are few reports on the anti-inflammatory activity of kojic acid and its derivatives

Method used

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  • Kojic acid and kojic acid derivatives, preparation method and application thereof
  • Kojic acid and kojic acid derivatives, preparation method and application thereof
  • Kojic acid and kojic acid derivatives, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 Fermentation and extraction of bacterial species

[0034] Aspergillus versicolor was purchased from the American Standard Strains Collection (ATCC), and the deposit number is ATCC 28286. The strain was streaked and revived, inoculated into PDA solid medium, and activated in a 28°C incubator for 5 days. Small colonies were cut from the PDA medium with a scalpel, inoculated into the PDB liquid medium, and cultured for 5 days on a shaker at 28° C. and 160 rpm to obtain a seed solution. Then, the seed liquid was inoculated into the rice solid medium, and cultured in a constant temperature and humidity box at 28°C for 30 days. Take the rice fermented product, add 400 mL of ethyl acetate per 200 g of the fermented product, and extract twice by cold soaking.

Embodiment 2

[0035] Example 2 Separation and identification of trexone A

[0036] The extract was chromatographed on a macroporous resin column, adsorbed overnight, eluted with 10%, 30%, 50%, 70%, 90%, 100% methanol-water gradients, each gradient was combined and spin-dried until no liquid was obtained to obtain 6 a subcomponent. The fourth sub-fraction (70% part) was separated and purified by semi-preparative high performance liquid chromatography, mobile phase: 65% MeOH, flow rate 4 mL / min, detection wavelength 210 nm, peak time 34.8-35.6 min. The peak was extracted and rotary evaporated to complete dryness to obtain 12.5 mg of white solid. The white solid was analyzed by high-resolution mass spectrometry and one-dimensional two-dimensional nuclear magnetic resonance. The results are as follows: Figure 1-8 , the structure of the compound is determined to be High resolution mass spectrometry [M-H] – m / z 419.1339, calculated 419.1348 (C 21 H 23 O 9 ), the molecular formula of the ...

Embodiment 3

[0039] Example 3 NO release inhibition experiment

[0040] The mouse macrophage cell line RAW 264.7 was cultured in high glucose DMEM medium supplemented with 1% penicillin and streptomycin at 37°C, 5% CO 2 cultured under conditions. First, the MTT method was used to test the cytotoxicity of the compounds to RAW 264.7 cells. Both compounds were non-cytotoxic, IC 50 >100 μM. RAW 264.7 cells were counted with a hemocytometer, and the cell concentration was adjusted to 5 × 10 3 cells / well, cultured in 96-well plate for 24h. LPS (1.0 μg / mL) was then added, and the compounds were diluted with culture medium to the final concentrations of 50, 25, 12.5, 6.25, and 3.125 μM, respectively. The sample addition group and the blank group were provided with 3 duplicate wells. After culturing for 24 hours, the NO release amount was tested with the NO kit, the OD value of each well was measured by a microplate reader, and the measurement wavelength was 550 nm. Inhibition rate=(OD value o...

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PUM

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Abstract

Kojic acid and kojic acid derivatives, preparation method and application thereof. The present invention proposes a kojic acid derivative, travertone A, whose structural formula is anti-inflammatory activity. In the test of anti-inflammatory activity, the half-inhibitory concentrations of travertone A and the precursor compound kojic acid in inhibiting mouse macrophage RAW264.7 were 15.5± 1.2μM and 40.8±3.1μM, troxone A and kojic acid can inhibit the expression of inflammatory factors IL-1β, IL-6, TNF-α and iNOS in mouse macrophages RAW264.7, and kojic acid can treat dextran sulfate The effect of sodium-induced colitis in mice is comparable to that of the positive drug mesalazine. Troxone A and kojic acid can be used in the preparation of anti-inflammatory drug precursors, laying a material foundation for the next step in the application of anti-inflammatory drugs in cosmetic and pharmaceutical research. .

Description

technical field [0001] The invention belongs to the technical field of natural medicines, and specifically relates to kojic acid and kojic acid derivatives and their anti-inflammatory uses. Background technique [0002] The chemical name of kojic acid is 5-hydroxy-2-hydroxymethyl-4-pyrone, which has significant tyrosinase inhibitory activity and can inhibit the production of skin melanin. It is widely used in the fields of medicine and cosmetics, and its market value huge. A variety of high-end whitening cosmetics, such as Longsine, Cosmetics, and Langsi Dongxing, all contain kojic acid, a key whitening ingredient. Clinically, creams containing 1% kojic acid can be used for the treatment of melasma, dark spots, sun spots and freckles. In addition, kojic acid is also an ideal new food antioxidant and industrial raw material. [0003] At present, there are few reports on the anti-inflammatory activity of kojic acid and its derivatives. Through the research on the anti-infl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04A61P29/00A61P1/00C12P17/18C12R1/66
CPCC07D493/04A61P29/00A61P1/00C12P17/18C07B2200/07Y02A50/30
Inventor 李天笑贾学伟王颖许春平梁佳欣熊亚妹袁梦
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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