Drimane-type sesquialter terpene cyclohexenone derivative, preparation method thereof and application

A technology of microorganisms and microbial strains, applied in the field of medicine and chemical industry, to achieve the effect of inhibiting proliferation and good anti-tumor activity

Inactive Publication Date: 2014-04-09
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This document only determined the relative configuration of the alkane-type sesquiterpene skeleton in penicillium A, but failed to determine the relative configuration of the asymmetric carbon atoms on the cyclohexenone ring and the absolute configuration of the entire molecule

Method used

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  • Drimane-type sesquialter terpene cyclohexenone derivative, preparation method thereof and application
  • Drimane-type sesquialter terpene cyclohexenone derivative, preparation method thereof and application
  • Drimane-type sesquialter terpene cyclohexenone derivative, preparation method thereof and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1: Microbial fermentation culture and preparation of compound 1 and compound 2

[0061] 1. Fermentation culture and extraction of fermented products

[0062] 1.1) Production strain

[0063] The toxin-producing bacteria used for the fermentation and production of compounds 1 and 2 in this example is the Penicillium purpurogenum BD-1-6 strain preserved in the General Microorganism Center of the China Microbiological Culture Collection Management Committee, and the preservation number is 5525. CGMCC No.5525.

[0064] 1.2) Fermentation culture

[0065]From the PDA medium (composition: 2% glucose, 2% agar, 1.5% NaCl, prepared with 20% potato boiling liquid) test tube slant , Scraped an appropriate amount of spores under aseptic conditions with an inoculation loop, streaked and inoculated them on a newly prepared PDA solid medium plate, and activated them in a 28°C incubator for 4 days. From the slant of the test tube that has been activated and cultivated for...

Embodiment 2

[0082] Embodiment 2: Antitumor activity test of compound 1 and compound 2

[0083] 1. Experimental materials

[0084] 1) Preparation of the tested sample solution

[0085] The tested samples were pure compound 1 and compound 2 isolated and refined in the above-mentioned Example 1. 5-Fluorouracil (Aladdin Reagent Co., Ltd., batch number 5402) and docetaxel trihydrate (Beijing Qimiwo Technology Co., Ltd., batch number 20110326) were used as positive control samples. Precisely weigh an appropriate amount of samples, and use DMSO to prepare solutions of required concentrations for testing activity.

[0086] 2) Subculture of cell lines and cells

[0087] The activity test adopts human chronic myeloid leukemia K562 cell line, human acute promyelocytic leukemia HL-60 cell line, human cervical cancer HeLa cell line, human gastric cancer BGC-823 line, human breast cancer MCF-7 line (the above cells Both can be purchased commercially, for example, from Shanghai Yaji Biotechnology ...

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Abstract

The invention belongs to the field of pharmaceutical chemicals, and relates to drimane-type sesquialter terpene cyclohexenone derivative, a preparation method thereof and application. Particularly, the drimane-type sesquialter terpene cyclohexenone derivative relates to a compound in a formula I, wherein Arabic numerals in the formula I indicate scalar potentials, and an R and an S respectively represent absolute configurations of carbon atoms with the corresponding potentials. The invention further relates to the preparation method of the compound, a composition containing the compound and the anti-tumor application. The invention further relates to penicillium purpurogenum BD-1-6 capable of being used for preparing the compound. The compound in the formula I can effectively kill tumor cells or suppress proliferation of the tumor cells, has excellent anti-tumor activity and has the potential of being used as an anti-tumor medicine. Attached is the formula I.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and relates to a drimane-type sesquiterpene cyclohexenone derivative, a preparation method and an application thereof. Background technique [0002] Albicanol (albicanol, also translated as "albicanol") is a relatively simple structure of drimane-type sesquiterpenoids, which has a trans six-membered bicyclic double ring shown in formula A or formula B. Semiterpene skeleton structure. [0003] [0004] Formula A Formula B [0005] Arabic numerals indicate the position, R and S respectively indicate the absolute configuration of the corresponding carbon atom [0006] Wherein, (+)-albicanol (+)-albicanol has 5S shown in above-mentioned formula A, 9S, the absolute configuration of 10S (Anilkumar AT, et al, Studies in lipase catalyzed transesterifications: Synthesis of (+)- albicanol, (+)-albicanol acetate and chiral intermediates useful in the synthesis of drimanes and labdanes, Te...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12N1/14C07C49/743C07D311/00C12P7/26C12P17/06A61K31/122A61K31/366A61P35/00A61P35/02C12R1/80
Inventor 崔承彬房士明李长伟吴长景杨明姚志伟
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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