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灰黄霉素衍生物和来源于青霉 CPCC 400528 的色胺生物碱。

Griseofulvin Derivative and Indole Alkaloids from Penicillium griseofulvum CPCC 400528.

机构信息

Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College , 1 Tian Tan Xi Li, Beijing 100050, People's Republic of China.

College of Herbal Medicine, Tianjin University of Traditional Chinese Medicines , 88 Yuquan Road, Tianjin 300193, People's Republic of China.

出版信息

J Nat Prod. 2017 Feb 24;80(2):371-376. doi: 10.1021/acs.jnatprod.6b00829. Epub 2017 Jan 24.

Abstract

A new griseofulvin derivative, 4'-demethoxy-4'-N-isopentylisogriseofulvin (1), three new indole alkaloids, 2-demethylcyclopiamide E (2), 2-demethylsperadine F (3), and clopiamine C (4), and five known metabolites (5-9) were isolated from Penicillium griseofulvum CPCC 400528. Compound 1 is the first reported griseofulvin analogue with an N-isopentane group and the first example of a naturally occurring N-containing griseofulvin analogue. Their structures and absolute configurations were elucidated through extensive spectroscopic analyses, calculated ECD, and single-crystal X-ray diffraction (Cu Kα). The possible biogenetic pathway of 1-3 was proposed. Compounds 1, 2, and 5 exhibited anti-HIV activities with IC values of 33.2, 20.5, and 12.6 μM, respectively.

摘要

从灰黄青霉 CPCC 400528 中分离得到一个新的灰黄霉素衍生物,4'-去甲氧基-4'-N-异戊基异灰黄霉素(1),三个新的吲哚生物碱,2-去甲基环巴胺 E(2),2-去甲基色胺 F(3)和克洛巴胺 C(4),以及五个已知的代谢产物(5-9)。化合物 1 是第一个报道的具有 N-异戊烷基团的灰黄霉素类似物,也是第一个天然存在的含 N 的灰黄霉素类似物。通过广泛的光谱分析、计算 ECD 和单晶 X 射线衍射(Cu Kα)确定了它们的结构和绝对构型。提出了 1-3 的可能生物合成途径。化合物 1、2 和 5 表现出抗 HIV 活性,IC 值分别为 33.2、20.5 和 12.6 μM。

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