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海洋来源真菌 sp. RR-YLW-12 与红藻相关的三萜类化合物

Terpenoids from the Marine-Derived Fungus sp. RR-YLW-12, Associated with the Red Alga .

机构信息

Yantai Institute of Coastal Zone Research, Center for Ocean Mega-Science, Chinese Academy of Sciences, Yantai 264003, People's Republic of China.

Chemistry and Chemical Engineering College, Yantai University, Yantai 264005, People's Republic of China.

出版信息

J Nat Prod. 2021 Jun 25;84(6):1763-1771. doi: 10.1021/acs.jnatprod.1c00021. Epub 2021 May 25.

Abstract

Two new meroterpenoids, aspermeroterpenes D and E ( and ), two new ophiobolin-type sesterterpenoids, the C-18 epimers of 18,19-dihydro-18-methoxy-19-hydroxyophiobolin P ( and ), and two new drimane-type sesquiterpenoids, 3-hydroxystrobilactone A () and 6--strobilactone A (), along with 11 known terpenoids (- and -) were isolated from the cultures of the algicolous fungus sp. RR-YLW-12, derived from the red alga . The structures and relative configurations of new compounds were established by detailed spectroscopic analysis of NMR and HRMS experiments, and the absolute configurations were assigned by X-ray diffraction experiments and comparison of their experimental and calculated ECD spectra. Compound features a rare 6/6/6/6/5 pentacyclic system with a meroterpenoid skeleton, and the structure of terretonin E () was revised in this study. Compound showed significant inhibitory activities against three microalgae, , , and , with IC values of 10.5, 5.2, and 3.1 μg/mL, respectively.

摘要

从红藻 中分离得到一株附生真菌 sp. RR-YLW-12 的培养物,从中分离得到两个新的倍半萜 meroterpenoids,aspermeroterpenes D 和 E( 和 ),两个新的 ophiobolin 型甾体二萜,C-18 差向异构体 18,19-二氢-18-甲氧基-19-羟基ophiobolin P( 和 ),以及两个新的 drimane 型倍半萜,3-羟基strobilactone A()和 6--strobilactone A(),同时还分离得到了 11 种已知的萜类化合物(- 和 -)。新化合物的结构和相对构型通过 NMR 和 HRMS 实验的详细光谱分析确定,绝对构型通过 X 射线衍射实验和比较其实验和计算的 ECD 光谱确定。化合物 具有罕见的 6/6/6/6/5 五环体系和 meroterpenoid 骨架,本研究中对 terretonin E()的结构进行了修订。化合物 对三种微藻 、 、 和 表现出显著的抑制活性,IC 值分别为 10.5、5.2 和 3.1 μg/mL。

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