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A kind of sesquiterpene cyclohexenone compound and its preparation method and application

A technology of cyclohexenones and compounds, which is applied in the field of sesquiterpene cyclohexenones and their preparation, can solve the problems that terpenoids rely on natural product extraction, terpenoids are non-modular, and there is no synthesis strategy. , to achieve the effects of rich diversity, strong stereoselectivity, and short preparation cycle

Active Publication Date: 2020-06-05
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the fact that the biosynthetic pathway has not been fully elucidated, terpenoids have a non-modular structure, and there is no universal and unified synthetic strategy, the source of terpenoids still relies on the extraction of natural products.

Method used

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  • A kind of sesquiterpene cyclohexenone compound and its preparation method and application
  • A kind of sesquiterpene cyclohexenone compound and its preparation method and application
  • A kind of sesquiterpene cyclohexenone compound and its preparation method and application

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preparation example Construction

[0064] The present invention provides the preparation method of the sesquiterpene cyclohexenone compound described in the above technical scheme, comprising the following steps:

[0065] Inoculating Penicillium expansum into a fermentation medium for fermentation to obtain a Penicillium expanse fermentation product;

[0066] Mixing the fermentation product of Penicillium extensa with alcohol, and performing ultrasonic extraction to obtain the crude extract of Penicillium extensa;

[0067] Purifying the crude extract of the expanded penicillin to obtain sesquiterpene cyclohexenone compounds.

[0068] The invention inoculates the Penicillium extensa into a fermentation medium for fermentation to obtain a Penicillium expanse fermented product. In the present invention, the Penicillium expanse is preferably derived from Aconitum aconitifolia, more preferably isolated from the root of Aconitum aconitifolia, and the Penicillium expanse is an endophytic fungus of Aconitum aconitum. ...

Embodiment 1

[0080] Inoculate Penicillium expansum on the PDA slant medium, culture at 28°C for 5 days to obtain activated Penicillium expanse, and store it in a refrigerator at 5°C for later use;

[0081] Take the washed potatoes, divide them into potato pieces with a diameter of 1 cm and place them in tissue culture bottles (45 g / bottle), cover the tissue culture bottles and sterilize at 120° C. for 30 minutes, cool to obtain the fermentation medium;

[0082] inoculating the activated Penicillium expansum into the fermentation medium according to the inoculation amount of 1%, and culturing at a constant temperature at 28° C. for 30 days after being covered to obtain a Penicillium expansiens fermentation product;

[0083] 50 g of the Penicillium extensa fermentation product was mixed with 80 mL of methanol, the resulting mixed solution was sonicated at 40 kHz for 30 min, filtered, and the filtrate was concentrated under reduced pressure until it had no alcohol smell, and 27.0 g of Penicill...

Embodiment 2

[0099] The compound expanded penicillin A, B, C and D prepared in Example 1 were screened for anti-inflammatory and anti-tumor activities.

[0100] 1. The compound expands the anti-inflammatory activity of penicillin A, B, C and D:

[0101] Nitric oxide has extensive and important biological regulation functions, and plays an important role in inflammation, tumor and cardiovascular system. When immune cells are stimulated by microbial endotoxins and inflammatory mediators, they will generate a large amount of inducible nitric oxide synthase and produce NO for immune response. Therefore, inhibition of NO production is a direct indicator of the anti-inflammatory activity of a compound.

[0102] (1) Take the mouse mononuclear macrophage RAW264.7 in the logarithmic growth phase (purchased from the Shanghai Cell Bank of the Chinese Academy of Sciences), induce stimulation with 1 μg / mL LPS, and add the compound expanded penicillin prepared in Example 1 at the same time A, B, C, an...

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Abstract

The invention belongs to the technical field of terpene compounds, and particularly relates to sesquiterpene cyclohexenone compounds, and a preparation method and application thereof. The sesquiterpene cyclohexenone compound provided by the invention has a novel framework structure, and diversity of sesquiterpene cyclohexanone compounds is enriched; and moreover, the sesquiterpene cyclohexanone compounds have anti-inflammatory and anti-tumor activity. According to the sesquiterpene cyclohexenone compounds prepared through microbial fermentation, the preparation method is short in period, mildin culture condition, few in byproducts, high in stereoselectivity, low in cost; industrialization can be realized easily; requirements of modern environmental protection and low carbon economy are met; and a new way can also be provided for production of sesquiterpene cyclohexanone compounds. The sesquiterpene cyclohexenone compound provided by the invention can be applied to preparation of anti-inflammatory and anti-tumor drugs, a new choice is provided for development of anti-inflammatory drugs.

Description

technical field [0001] The invention relates to the technical field of terpenoids, in particular to a sesquiterpene cyclohexenone compound and its preparation method and application. Background technique [0002] Terpenoids - hydrocarbons with molecular formulas that are multiples of isoprene units and their oxygenated derivatives, are a large class of natural products with a high degree of diversity, including monoterpenes, sesquiterpenes, diterpenes, sesquiterpenes Semiterpene cyclohexenone, triterpenes, etc. Many terpenoids have been developed as important drugs in the treatment of cancer, bacterial infections, malaria, and various other human diseases. Therefore, the synthesis of terpenoids is very important. However, due to the fact that the biosynthetic pathway has not been fully elucidated, terpenoids have a non-modular structure, and there is no universal and unified synthesis strategy, the source of terpenoids still relies on the extraction of natural products. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00C07D303/32C12P17/02C12P33/20A61P29/00A61P35/00C12R1/80
CPCA61P29/00A61P35/00C07D303/32C07J71/001C12P17/02C12P33/20
Inventor 蔡乐丁中涛王家鹏舒燕
Owner YUNNAN UNIV
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