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Curcumenol microbial transformation derivatives, preparation method and use thereof

A technology of curcumenol and hydroxycurcumenol, which is applied in the field of medicine to achieve the effects of increasing structural modification sites, preventing and treating inflammation, and increasing polarity and water solubility

Active Publication Date: 2016-11-02
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method disclosed in this patent for preparing curcumenol derivatives by means of microbial transformation, and the anti-inflammatory effect of the prepared new compound on inhibiting the release of NO inflammatory mediators have not been reported in the literature

Method used

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  • Curcumenol microbial transformation derivatives, preparation method and use thereof
  • Curcumenol microbial transformation derivatives, preparation method and use thereof
  • Curcumenol microbial transformation derivatives, preparation method and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Embodiment 1: the microbial conversion of curcumenol and the separation of conversion product

[0031] The specific steps of microbial transformation are as follows:

[0032] a) The preparation of potato liquid culture medium: take fresh potato, peel, cut into 2cm 3 For small pieces, add 5 times the amount of water to boil, keep boiling for 30 minutes, filter the residue with gauze, add water to the filtrate (1 liter of culture medium per 200 grams of potatoes), and add 2% glucose after constant volume. Divide the prepared culture solution, 250mL Erlenmeyer flask can be filled with 60mL culture solution, and 500mL Erlenmeyer flask can be filled with 200mL culture solution. Seal the mouth of the bottle with gauze and kraft paper, and put it in an autoclave for sterilization. The sterilization condition is 115°C for 30 minutes.

[0033] b) Microbial cultivation: Three kinds of fungal strains Penicillium urticae IFFI 04015, Cunninghamella echinulata AS 3.3400, and Mucor...

Embodiment 2

[0067] Example 2: Inhibitory activity experiment of transformation products and substrates on release of nitric oxide (NO) from mouse mononuclear macrophage RAW 264.7 induced by lipopolysaccharide

[0068] Mouse mononuclear macrophage RAW 264.7 (ATCC TIB-71) was cultured in 10% heat-inactivated (56°C, 30min) fetal bovine serum (FBS), 100 U / mL penicillin sodium (Gibco), 100 μg / mL streptavidin in RPMI 1640 (Gibco) medium, 37°C, 5% CO 2 grown in a constant temperature incubator. Because NO is extremely unstable, it is quickly metabolized into nitrous acid (NO) in the cell culture supernatant. 2 - ), so the Griess method was used to measure NO in the sample 2 - concentration as an indicator of NO levels. Griess reagent A: 0.1% N-naphthalene ethylenediamine hydrochloride (naphthylene diaminedihydrochloride) dissolved in water: Griess reagent B: 1% p-aminobenzenesulfonamide (sulphanilamide) dissolved in 5% H 3 PO 4 middle. Mix reagents A and B in equal volumes before use. D...

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Abstract

The invention discloses a curcumenol microbial conversion derivative, and a preparation method and a use thereof. The above conversion product has a structure represented by formula (I) or formula II, has higher polarity and more modification sites than curcumenol, can be easily processed to prepare preparations, and can be further structure-derived. A substrate curcumenol is biologically converted by using Penicillium urticae IFFI 04015, Cunninghamella echinulata AS 3.3400 and Mucor polymorphosporus AS 3.3443, an organic solvent is used to extract the conversion product in a fermentation liquid, and chromatography is used to separate and purify the conversion product. The curcumenol conversion product can be used for preventing and / or treating inflammations caused by nitrogen monoxide inflammation mediator release, and preparing anti-inflammatory drugs.

Description

technical field [0001] The invention relates to curcumenol microbial transformation derivatives, a preparation method and application thereof, and belongs to the technical field of medicine. Background technique [0002] Inflammation is the body's defense-based response to the damage caused by various inflammatory factors, and often causes systemic reactions, such as fever, increase in the number of white blood cells in the blood, and varying degrees of degeneration of the heart, liver, kidney and other organs. Characterized by necrosis. Acute inflammation manifests itself as redness, swelling, heat, pain, and dysfunction as part of the body's defense response. However, chronic inflammation may lead to cancer, diabetes, lung disease, cardiovascular system and nervous system diseases, causing very serious harm to the body and even threatening the life safety of patients. [0003] Nitric oxide (NO) is an inorganic small molecule free radical generated by L-arginine (L-Arg) i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/08C07C49/733C07C65/36C12P7/40C12P7/38C12P17/18A61P29/00C12R1/785C12R1/80C12R1/645
Inventor 陈丽霞邱峰赵烽赵倩梁艳艳张萌
Owner SHENYANG PHARMA UNIVERSITY
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