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贝山唑类化合物A-D，源自濒危针叶树内生真菌P-4-1的前所未有的含环庚酮聚酮化合物。

Beshanzoides A-D, unprecedented cycloheptanone-containing polyketides from P-4-1, an endophytic fungus of the endangered conifer .

作者信息

Chen Hao-Wei, Jiang Chun-Xiao, Li Jiyang, Li Na, Zang Yi, Wu Xi-Ying, Chen Wen-Xue, Xiong Juan, Li Jia, Hu Jin-Feng

机构信息

Department of Natural Medicine, School of Pharmacy, Fudan University Shanghai 201203 PR China

School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University Zhejiang 318000 PR China

出版信息

RSC Adv. 2021 Dec 14;11(63):39781-39789. doi: 10.1039/d1ra08377e. eCollection 2021 Dec 13.

DOI:10.1039/d1ra08377e
PMID:35494150
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9044568/
Abstract

A number of previously undescribed (1-7) and structurally related known (8-17) isobenzofuran-type polyketides were obtained from the fermentation of P-4-1, an endophytic fungus isolated from the fresh trunk bark of the critically endangered conifer . Beshanzoides A-D (1-4, resp.) feature a cycloheptanone-containing isobenzofuran ring system hitherto unknown, which might be biosynthesized two steps of aldol reactions starting from a common co-occurring isobenzofuran-type polyketide as the precursor. The new structures were elucidated by spectroscopic methods, electronic circular dichroism data, and single crystal X-ray diffraction analyses. Beshanzoide E (5) showed antimicrobial activity (MIC: 16 μg mL) against , whereas (±)-strobide A (10) inhibited (MIC: 16 μg mL) . Cyclopaldic acid (12) and 3--methyl-cyclopaldic acid (13) exhibited inhibitory effects against acetyl-CoA carboxylase 1 (ACC1) with IC values of 0.96 and 11.77 μM, respectively. Compound 12 also inhibited (IC: 7.56 μM) ATP-citrate lyase (ACL).

摘要

从一种从极度濒危针叶树新鲜树干树皮中分离得到的内生真菌P-4-1的发酵产物中，获得了一些先前未描述的（1-7）以及结构相关的已知异苯并呋喃型聚酮化合物（8-17）。北山酮A-D（分别为1-4）具有迄今未知的含环庚酮的异苯并呋喃环系统，其可能由一种共同存在的异苯并呋喃型聚酮化合物作为前体，通过两步羟醛反应生物合成。通过光谱方法、电子圆二色性数据和单晶X射线衍射分析阐明了这些新结构。北山酮E（5）对[具体微生物]显示出抗菌活性（最低抑菌浓度：16μg/mL），而（±）-球松素A（10）对[具体微生物]有抑制作用（最低抑菌浓度：16μg/mL）。环杷地酸（12）和3-甲基环杷地酸（13）对乙酰辅酶A羧化酶1（ACC1）表现出抑制作用，其半数抑制浓度值分别为0.96和11.77μM。化合物12也抑制（半数抑制浓度：7.56μM）ATP-柠檬酸裂解酶（ACL）。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebe2/9044568/3a4304382197/d1ra08377e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebe2/9044568/480fd6f71169/d1ra08377e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebe2/9044568/1cb3c8f8e509/d1ra08377e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebe2/9044568/dca148e953fb/d1ra08377e-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebe2/9044568/30afd80133b9/d1ra08377e-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebe2/9044568/02528f5e029e/d1ra08377e-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebe2/9044568/3a4304382197/d1ra08377e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebe2/9044568/480fd6f71169/d1ra08377e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebe2/9044568/1cb3c8f8e509/d1ra08377e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebe2/9044568/dca148e953fb/d1ra08377e-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebe2/9044568/30afd80133b9/d1ra08377e-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebe2/9044568/02528f5e029e/d1ra08377e-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ebe2/9044568/3a4304382197/d1ra08377e-s1.jpg

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