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从深海沉积物来源真菌棘孢青霉 SD-321 中分离得到的抗菌性双醇类倍半萜及其相关衍生物。

Antimicrobial Phenolic Bisabolanes and Related Derivatives from Penicillium aculeatum SD-321, a Deep Sea Sediment-Derived Fungus.

机构信息

†Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.

‡University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, People's Republic of China.

出版信息

J Nat Prod. 2015 Apr 24;78(4):844-9. doi: 10.1021/acs.jnatprod.5b00004. Epub 2015 Mar 12.

DOI:10.1021/acs.jnatprod.5b00004
PMID:25763602
Abstract

Three new phenolic bisabolane sesquiterpenes, peniciaculins A (1) and B (2) and (7S)-(-)-10-hydroxysydonic acid (3), together with a new nor-bisabolane derivative, 1-hydroxyboivinianin A (4), as well as six known bisabolanes (5-10), were identified from the culture of Penicillium aculeatum SD-321, a fungus isolated from deep-sea sediments. The structures of these compounds were mainly determined by analysis of spectroscopic data, and the absolute configurations of compounds 1-4 were established by comparing their ECD spectra with those of known analogues or by TDDFT-ECD calculations. Compound 1 represents the first example of a bisabolane analogue linked to a diphenyl ether moiety via an ether bond, while compound 2 appears to be the first dimeric bisabolane analogue where the two monomers are coupled to each other via an ester bond. The isolated compounds were evaluated for antimicrobial activity against 10 human and aquatic pathogenic bacteria and three plant-pathogenic fungi.

摘要

从深海沉积物中分离得到的青霉属真菌 SD-321 的培养物中,鉴定出三种新的倍半萜酚类化合物,peniciaculins A(1)和 B(2)和(7S)-(-)-10-羟基 Sydonic 酸(3),以及一种新的诺倍半萜衍生物 1-羟基 boivinianin A(4),以及六种已知的倍半萜类化合物(5-10)。这些化合物的结构主要通过光谱数据分析确定,化合物 1-4 的绝对构型通过将其 ECD 光谱与已知类似物进行比较或通过 TDDFT-ECD 计算来确定。化合物 1 代表了第一个通过醚键连接到二苯醚部分的倍半萜类似物,而化合物 2 似乎是第一个通过酯键连接的二聚倍半萜类似物,其中两个单体相互连接。对分离得到的化合物进行了抗 10 种人类和水生致病性细菌和 3 种植物病原真菌的抗菌活性评价。

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