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Method for preparing andrographolide esterfied derivatives through biocatalysis

A technology of andrographolide and biocatalysis, applied in biochemical equipment and methods, methods based on microorganisms, microorganisms, etc., can solve the problems of by-products and difficult separation of products, poor selectivity, environmental pollution, etc., and achieve simple and easy reaction process control, product ease, and environmental friendliness

Inactive Publication Date: 2009-12-02
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Synthesis of glucographolide derivatives by chemical methods requires high energy consumption, poor selectivity, easy to produce by-products and difficult separation of products; and because a large amount of organic solvents and catalysts are used in the reaction process, it will bring serious environmental pollution on the one hand. On the other hand, there are often some toxic chemical substances left in the product and there are potential safety hazards

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Put 0.5g andrographolide, 20ml acetone, 10mg lipase from Candida antarctica (10,000U / g, Novozymes China Biotechnology Co., Ltd.) and 6ml vinyl acetate into a stoppered Erlenmeyer flask , placed in a 30°C, 100rpm water bath constant temperature oscillator, reacted for 6 hours, filtered to remove lipase, evaporated under reduced pressure to remove the organic medium; the residue was dissolved in ethyl acetate, evaporated under reduced pressure to remove ethyl acetate, and dried in vacuo (45° C., 0.08 MPa) to obtain 14-O-acetylandrographolide esterified derivatives (90% yield).

Embodiment 2

[0022] Put 0.5g andrographolide, 20ml acetone, 100mg lipase from Candida antarctica (10,000U / g, Novozymes China Biotechnology Co., Ltd.) and 6ml vinyl butyrate into a stoppered Erlenmeyer flask place in a water bath constant temperature oscillator at 60°C and 100rpm to oscillate, react for 24 hours, filter to remove lipase, evaporate under reduced pressure to remove the organic medium; dissolve the residue with ethyl acetate, evaporate under reduced pressure to remove ethyl acetate, vacuum Dry (45°C, 0.08MPa) to obtain 14-O-butyrylandrographolide esterified derivative (95% yield).

Embodiment 3

[0024] Put 0.5g andrographolide, 20ml acetone, 200mg lipase from Candida antarctica (10,000U / g, Novozymes China Biotechnology Co., Ltd.) and 6ml vinyl caproate into a stoppered Erlenmeyer flask place in a water bath constant temperature oscillator at 50°C and 100rpm, react for 24 hours, remove lipase by filtration, remove the organic medium by evaporation under reduced pressure; dissolve the residue with ethyl acetate, remove ethyl acetate by evaporation under reduced pressure, vacuum Dry (45°C, 0.08MPa) to obtain 14-O-hexanoylandrographolide esterified derivative (yield: 94%).

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PUM

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Abstract

The invention relates to a method for preparing andrographolide esterfied derivatives through biocatalysis, and belongs to the fields of biocatalysis and biosynthesis. The method takes acetone as solvent and aliphatic ester with C2-C18 carbon chain length as acyl donor, and utilizes lipase to catalyze andrographolide for acylation reaction at a reaction temperature of between 30 and 70 DEG C so as to synthesize the andrographolide esterfied derivatives. The method has the advantages of mild reaction conditions, environmental protection, high selectivity and controllability of the reaction, simple reaction process, easy separation of products from a reaction mixing system, and the like.

Description

technical field [0001] The invention belongs to the field of biocatalysis and biosynthesis, and relates to a method for preparing andrographolide esterified derivatives by biocatalysis in an organic medium. Background technique [0002] Andrographolide is a diterpene lactone compound extracted from Andrographis Panicutate (Burm.f.) Ness, a plant of the family Acanthaceae. It is one of the main active ingredients of the traditional Chinese medicine Andrographis paniculata. functions such as swelling. Modern pharmacological studies have shown that andrographolide derivatives have anti-inflammatory, anti-bacterial, anti-virus, anti-tumor, immune regulation, liver protection and gallbladder functions. Therefore, research work on finding more active andrographolide derivatives by modifying the structure of andrographolide compounds has attracted much attention. [0003] At present, the synthesis of esterified derivatives of andrographolide adopts chemical methods in China. Syn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/04C12R1/72C12R1/785C12R1/645C12R1/38
Inventor 陈志刚徐杰曹林韩永斌
Owner NANJING AGRICULTURAL UNIVERSITY
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