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Asiatic acid derivative, preparation method thereof, and application thereof in preparing hypoglycemic drugs

A kind of asiatic acid and pharmaceutical technology, applied in the field of natural medicinal chemistry, can solve the problems of unfavorable large-scale production and promotion, cumbersome preparation process, and large toxic and side effects

Active Publication Date: 2015-09-23
NAVY MEDICINE RES INST OF PLA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] At present, considerable breakthroughs have been made in the research on asiatic acid and its derivatives in the prior art. For example, WO96 / 17819 A1 discloses a kind of asiatic acid and its derivatives, which are effective for skin damage. The effect has a certain therapeutic effect, and provides a new method for modern beauty fields such as lightening scars and removing scars; CN101991578A discloses a kind of asiatic acid and its inhibitory effect on α-glucosidase, although it has a certain therapeutic effect effect, but the preparation process is cumbersome, and the residual toxic reagents in the preparation process have large toxic and side effects, which has certain limitations in actual treatment and is not conducive to large-scale production and promotion

Method used

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  • Asiatic acid derivative, preparation method thereof, and application thereof in preparing hypoglycemic drugs
  • Asiatic acid derivative, preparation method thereof, and application thereof in preparing hypoglycemic drugs
  • Asiatic acid derivative, preparation method thereof, and application thereof in preparing hypoglycemic drugs

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preparation example Construction

[0067] The present invention also provides a method for preparing Asiatic acid derivatives as described in the first aspect, characterized in that the structure of Asiatic acid is modified by the microbial enzyme of Aspergillus niger, specifically comprising:

[0068] Step 1: Microbial conversion reaction of asiatic acid

[0069] The substrate solution obtained by dissolving asiatic acid in ethanol solution is added to the fermented liquid of Aspergillus niger, and cultivated for 7-10 days under the conversion reaction conditions of 25-28°C and 150-250rpm / min;

[0070] Step 2: Extraction, separation and purification of the product

[0071] After the conversion is completed, filter, extract, concentrate, and separate and purify to obtain compound 1 and compound 2;

[0072] Step 3: Identification of the product

[0073] The obtained compound 1 and compound 2 were identified.

[0074] According to a preferred embodiment of the subject matter of the second aspect of the present...

Embodiment 1

[0096] Example 1——Preparation and extraction of asiatic acid derivative compounds 1 and 2

[0097] Insert Aspergillus niger CGMCC 3.739 bacterial classification with 2% inoculum size in 8 bottles of 1000ml (400ml culture medium in each bottle), put in constant temperature shaker, 180rpm, 27 ℃ after 72 hours of culture, add 200mg of substrate Asiatic acid (dissolved in 16ml of ethanol, adding 2ml to each bottle), continued to cultivate for 10 days. After the fermentation is completed, filter the mycelium, extract the filtrate three times with equal volumes of ethyl acetate, grind the mycelium after drying, and extract three times with 500ml ethyl acetate ultrasonically, each time for 30min, combine the ethyl acetate extract and the extract, Concentrate to a small volume on a rotary evaporator, and dry to obtain the conversion reaction extract (1.5 g).

[0098] After the conversion reaction extract was purified by silica gel column and gel column, it was prepared by semi-prepar...

Embodiment 2

[0099] Example 2——Structure Identification of Asiatic Acid Derivative Compound 1

[0100] Compound 1 is a white solid, HR-ESI-MS gives 501.3238 ([M-H]-), combined with 1 H-NMR and 13 C-NMR deduces that the molecular formula is C 30 h 46 o 6 . 1 H-NMR (600MHz, pyridine-d 5), showing that the compound has six groups of methyl hydrogen signals δ1.43(3H,s), δ1.25(3H,s), δ1.21(3H,s), δ1.01(3H,d,6.0) , δ0.96(3H, s), δ0.90(3H, d, 6.0); there is an active hydrogen signal at the low field: δ5.60(t, 3.9), which is speculated to be the hydrogen on the double bond. 13 C-NMR shows two unsaturated carbon atoms δ127.1 and δ140.8, one carboxyl carbon atom δ180.3, and one carbonyl carbon atom δ216.5. Based on the above information, it can be inferred that the compound is a ursane-type pentacyclic triterpenoid.

[0101] According to HSQC and HMBC spectra, the hydrocarbons of the compound can be further assigned.

[0102] Compared with asiatic acid, 1 In the H-NMR spectrum, a hydrogen ...

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Abstract

The invention provides an Asiatic acid derivative compound, or a pharmaceutically acceptable salt or ester thereof, or any optical isomer thereof, or any tautomer thereof represented by a general formula (I). In the formula, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 can be independently same or different, and can be hydrogen, hydroxy, carboxy, C1-6 alkylhydroxyl, C1-6 alkylcarboxyl, C1-6 alkoxy, unsubstituted or mono-substituted or poly-substituted C3-6 cycloalkyl substituted by C1-6 alkyl, halogen, hydroxy or C1-6 alkoxy, or unsubstituted or mono-substituted or poly-substituted C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl substituted by halogen. The invention also provides a preparation method of the above Asiatic acid derivative, and an application of the derivative in the preparation of hypoglycemic drugs. The preparation method is suitable for large-scale productions. The obtained Asiatic acid derivative has an outstanding effect in the application of the preparation of the hypoglycemic drugs.

Description

technical field [0001] The invention belongs to the field of natural medicinal chemistry, and relates to a compound, in particular to an asiatic acid derivative and its preparation method and its application in the preparation of hypoglycemic drugs. Background technique [0002] Asiatic acid, also known as asiatic acid, is an ursane-type pentacyclic triterpenoid extracted from the medicinal Umbelliferae plant Centella asiatica (L.) Urban. Its structural formula is: [0003] [0004] Because Asiatic acid has a wide range of biological activities, it is widely used in the field of natural medicinal chemistry, and has good effects in anti-tumor, improving cognition, anti-diabetes, anti-inflammation, antibacterial, and promoting wound healing. [0005] In addition, since 1971, it has been discovered that Asiatic acid has the effect of treating skin wounds. It is self-evident that research on the pharmacological effects and structural modification of Asiatic acid and its deriv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61P3/10C12P33/00C12R1/685
CPCC07J63/008C12P33/00
Inventor 冯旭储智勇邹赢锌栾洁陈松张术郭飞飞
Owner NAVY MEDICINE RES INST OF PLA
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