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A preparation method and application of a microbial conversion product of curcumenol

A technology of microbial transformation and curcumenol, applied in the field of medicine, can solve problems affecting the formation of preparations and drug development, poor water solubility, difficulty in structural modification, etc., and achieve good research and development prospects

Active Publication Date: 2016-06-15
SHENYANG PHARMA UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its poor water solubility, it is easily soluble in small polar organic solvents such as ethyl acetate and chloroform, which affects the formation of its preparations and drug development.
In view of the limitations of chemically variable sites in its structure, it is difficult to modify its structure by organic chemical methods, and there is no literature report

Method used

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  • A preparation method and application of a microbial conversion product of curcumenol
  • A preparation method and application of a microbial conversion product of curcumenol
  • A preparation method and application of a microbial conversion product of curcumenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: a) preparation of potato liquid culture medium: get 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.

[0019] b) Microbial culture: Inoculate Mucorspinosus AS3.2450 from Potato Dextrose Agar (PDA) (inoculation area is about 0.05cm 2 ) into the potato liquid medium prepared above, placed in a shaker at 160 rpm, and cultured at 26°C for 2 days.

[0020] c) Adding the substrate: dissolve the substrate curcumen...

Embodiment 2

[0023] Example 2: a) Preparation of potato liquid medium: same as Example 1.

[0024] b) Microbial culture: Inoculate Mucorspinosus AS3.2450 from Potato Dextrose Agar (PDA) (inoculation area is about 0.05cm 2 ) into the potato liquid medium prepared above, placed in a shaker at 160 rpm, and cultured at 26°C for 2 days.

[0025] c) Adding the substrate: dissolve the substrate curcumenol with an appropriate amount of acetone to prepare a 10 mg / mL acetone solution. A total of 200 mg of curcumenol was added to the microbial fermentation broth in step b) that had been cultured for 2 days, and the culture was continued for 8 days under the same conditions (160 rpm, 26° C.).

[0026] d) Treatment of fermented liquid: Same as in Example 1, 755 mg of crude extract was obtained.

[0027] e) The silica gel column chromatographic separation method was the same as in Example 1, and the target conversion product 1α-hydroxycurcumenol (100.8 mg) was obtained with a yield of 50.4%.

Embodiment 3

[0028] Example 3: a) Preparation of potato liquid medium: same as Example 1.

[0029] b) Microbial culture: Inoculate Mucorspinosus AS3.2450 from Potato Dextrose Agar (PDA) (inoculation area is about 0.05cm 2 ) into the potato liquid medium prepared above, placed in a shaker at 160 rpm, and cultured at 26°C for 3 days.

[0030] c) Adding the substrate: dissolve the substrate curcumenol with an appropriate amount of acetone to prepare a 10 mg / mL acetone solution. A total of 200 mg of curcumenol was added to the microbial fermentation broth of step b) that had been cultured for 3 days, and the culture was continued for 4 days under the same conditions (160 rpm, 26° C.).

[0031] d) Treatment of fermented liquid: Same as in Example 1, 630 mg of crude extract was obtained.

[0032] e) The silica gel column chromatographic separation method was the same as in Example 1, and the target conversion product 1α-hydroxycurcumenol (79.2 mg) was obtained with a yield of 39.6%.

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Abstract

The invention discloses a microbial conversion product of curcumenol, its use and preparation method. The structure of the transformation product is 1 α -Hydroxycurcumenol. The conversion product 1 α -Hydroxycurcumenol can be used as an anti-inflammatory drug for the prophylaxis and / or treatment of humans and animals. Mucor echinocystis Mucor ? spinosus? AS? 3.2450 biotransforms the substrate curcumenol, and uses ethyl acetate to extract the converted product in the fermentation broth, and uses silica gel column chromatography to separate and purify the converted product. The obtained conversion product has a purity of over 98%.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular it is a microbial conversion product of curcumenol and its use and preparation method. Background technique [0002] Nitric oxide (NO) is an inorganic small molecule free radical generated by L-arginine (L-Arginine, L-Arg) in vivo under the action of inducible nitric oxide synthase (iNOS). An important messenger molecule and neurotransmitter in the body, involved in regulating many physiological or pathological processes of the body, such as vasodilation, non-specific host defense response, local ischemia-reperfusion injury, chronic or acute inflammatory response, etc. (Bioorganic & Medicinal Chemistry, 2001 , 9, 1887-1893). Studies have confirmed that some types of cells such as macrophages, epithelial cells, and smooth muscle cells respond to some pro-inflammatory factors such as interleukin-1b (IL-1b), tumor necrosis factor-a (TNF-a) and lipopolysaccharide (LPS), etc. Stimulat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/08C12P17/18A61K31/352A61P29/00C12R1/785
CPCC07D493/08C12N1/14C12P17/181C12N1/145C12R2001/785
Inventor 陈丽霞邱峰赵烽赵倩
Owner SHENYANG PHARMA UNIVERSITY
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