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An ascochlorin compound and its application in the preparation of antitumor drugs or dihydroorotate dehydrogenase inhibitor drugs

A technology of ascochlorin and an antitumor drug, which is applied in the field of marine natural products, can solve the problems that the antitumor potential needs to be further explored and the research on the mechanism of action is weak, and achieves a broad-spectrum significant tumor cell proliferation inhibitory activity and a broad-spectrum significant Dihydroorotate dehydrogenase inhibitory activity, highly active effect

Active Publication Date: 2021-02-05
GUANGXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ascochlorins have been reported to have antioxidant and antibacterial activities, and also have inhibitory activity on some tumor cells, but the research on the mechanism of action is very weak, and the antitumor potential needs to be further explored

Method used

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  • An ascochlorin compound and its application in the preparation of antitumor drugs or dihydroorotate dehydrogenase inhibitor drugs
  • An ascochlorin compound and its application in the preparation of antitumor drugs or dihydroorotate dehydrogenase inhibitor drugs
  • An ascochlorin compound and its application in the preparation of antitumor drugs or dihydroorotate dehydrogenase inhibitor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Sclerotinia acremonium (Acremonium sclerotigenum) GXIMD02501

[0033] Acremonium sclerotigenum GXIMD 02501 was isolated from the symbiotic bacteria collected from the Beibu Bay of Guangxi, China, and was preserved in the Guangdong Microbial Culture Collection Center (GDMCC). Address: 5th Floor, Building 59, Guangdong Institute of Microbiology, No. 100 Xianlie Middle Road, Guangzhou, Guangdong Province, Guangdong Institute of Microbiology, deposit number: GDMCC No.60670.

Embodiment 2

[0034] Preparation and separation of embodiment 2 ascochlorin compound acremochlorin A

[0035] 1. Medium

[0036] 1.1. Seed culture medium: Each liter of medium contains 15g of malt extract powder, 20g of coarse sea salt, and the balance is water, pH7.5. Mix evenly according to the above-mentioned components and contents, and then sterilize at 121°C for 30 minutes for later use.

[0037] 1.2. Fermentation medium: Each 1L Erlenmeyer flask medium contains: 120g rice, 1.5g bacteriological peptone, 3g coarse sea salt, 150mL water, pH7.5. Mix evenly according to the above-mentioned components and contents, and then sterilize at 121°C for 30 minutes for later use.

[0038]2. Fermentation

[0039] 2.1. Seed culture: Inoculate activated Acremonium sclerotigenum GXIMD02501 into 1L triangular culture flasks each containing 300mL of seed culture medium, culture at 25°C and 180rpm for 72 hours to obtain seed solution.

[0040] 2.2. Fermentation culture: the seed liquid was inserted i...

Embodiment 3

[0044] Example 3 Structural identification of ascochlorin compound acremochlorin A

[0045] The ascochlorin compound acremochlorin A is a colorless needle-like crystal, and its NMR data assignment is shown in Table 1; its high-resolution mass spectrum HRESIMS gives a quasi-molecular ion peak m / z407.1968[M+H] + (calcd forC 23 h 32 ClO 4 , 407.1989) determined that its molecular formula is C 23 h 31 ClO 4 , containing 8 degrees of unsaturation. 1 The HNMR spectrum shows a phenolic hydroxyl group 2-OH (δ H 12.89,s), 1 aldehyde group (δ H 10.17,s), 3 alkene protons H-10(δ H 5.20,t,J=7.0Hz) and terminal methylene H 2 -21(δ H 4.79, s, H-21a; 4.53, s, H-21b), a oxymethine H-18 (δ H 3.27, overlapped) and 1 methine H-14 (δ H 1.63,m), 5 methylene H 2 -9(δ H 3.36–3.40, d, J=7.0Hz), H 2 -12(δ H 2.04,m; 1.79,m), H 2 -13(δ H 1.61, m), H 2 -16(δ H 2.25,m; 1.82,m) and H 2 -17(δ H 1.73,m; 1.44,m), and four unimodal methyl groups, H 3 -7(δ H 2.63), H 3 -20(δ H 0.96), H...

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Abstract

The invention provides a bisporin compound and its application in the preparation of antitumor drugs or dihydroorotate dehydrogenase inhibitor drugs, and relates to the field of marine natural products. An ascochlorin compound is disclosed, the structural formula of which is shown in formula (I). The cyclohexanol fragment of the compound has a rare gem-dimethyl group and an extracyclic double bond, and has a broad spectrum of significant tumor cell Proliferation inhibitory activity and dihydroorotate dehydrogenase inhibitory activity, so it is an ideal candidate compound to be developed as an anti-tumor drug or a dihydroorotate dehydrogenase inhibitor drug with novel structure and high activity.

Description

technical field [0001] The invention relates to the field of marine natural products, in particular to an ascochlorin compound and its application in the preparation of antitumor drugs or dihydroorotate dehydrogenase inhibitor drugs. Background technique [0002] Malignant tumors are still non-communicable diseases with extremely high morbidity and mortality worldwide, posing a serious threat to human life and health. Natural products are an important source of drug development. According to reports, from 1981 to 2019, anticancer drugs derived from natural products accounted for more than 75% of the anticancer drugs on the market. Marine microbial resources are abundant, and they are new ideal resources for discovering novel active metabolites. [0003] Dihydroorotate dehydrogenase (dihydroorotate dehydrogenase, DHODH) is an iron-containing flavin-dependent enzyme present in the inner mitochondrial membrane, which catalyzes the key reaction in step 4 of the de novo pyrimid...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/57A61P35/00A61P35/02C12N1/14C12P7/26C12R1/645
CPCA61P35/00A61P35/02C07C47/57C12P7/26C07C2601/14C12N1/145C12R2001/645
Inventor 罗小卫刘永宏王军舰高程海蔡国弟
Owner GUANGXI UNIV OF CHINESE MEDICINE
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