Talaroterpenoids A-F: Six New Seco-Terpenoids from the Marine-Derived Fungus Talaromyces aurantiacus.

IF 4.9 2区医学 Q1 CHEMISTRY, MEDICINAL Marine Drugs Pub Date : 2024-10-18 DOI:10.3390/md22100475

Zi-Hong Peng, Hui Jia, Yan-Liang Luo, Li-Jun Zhang, Jia-Tong Zhou, Yuan-Han Xie, Li-Jun Wang, Jiang-Ke Qin, Jun Li, Guo-Hai Zhang, Rui-Yun Yang, Wei-Feng Xu

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Abstract

Six new highly oxidized seco-terpenoids, including three 3-nor-labdane type diterpenes, talaroterpenoids A-C (1-3), and three meroterpenoids containing an orthoester group, talaroterpenoids D-F (6-8), together with five known compounds (4-5 and 9-11), were isolated from the marine-derived fungus Talaromyces aurantiacus. Their chemical structures were elucidated through 1D, 2D NMR, HRESIMS, J-based configuration analysis (JBCA), computational ECD calculations, and single-crystal X-ray diffraction analysis. Compounds 1 and 2 contain an unusual 6,20-γ-lactone-bridged scaffold. Compounds 10 and 11 presented inhibitory effects on NO release in lipopolysaccharide (LPS)-induced BV-2 cells with IC₅₀ values of 11.47 and 11.32 μM, respectively. Talaroterpenoid C (3) showed moderate antifungal activity against A. alternata and P. theae Steyaert.

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Talaroterpenoids A-F：源自海洋的真菌 Talaromyces aurantiacus 的六种新的仲萜类化合物。

从海洋源真菌 Talaromyces aurantiacus 中分离出了六种新的高度氧化仲三萜类化合物，包括三种 3-nor-labdane 型二萜类化合物 talaroterpenoids A-C （1-3）和三种含有正酯基团的 meroterpenoids，即 talaroterpenoids D-F（6-8），以及五种已知化合物（4-5 和 9-11）。通过一维、二维核磁共振、HRESIMS、基于 J 的构型分析（JBCA）、计算 ECD 计算和单晶 X 射线衍射分析，阐明了它们的化学结构。化合物 1 和 2 包含一个不寻常的 6,20-γ 内酯桥架。化合物 10 和 11 具有抑制脂多糖（LPS）诱导的 BV-2 细胞中 NO 释放的作用，IC50 值分别为 11.47 和 11.32 μM。他拉罗萜类化合物 C（3）对交替孢霉属（A. alternata）和 P. theae Steyaert 表现出中等程度的抗真菌活性。

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来源期刊

Marine Drugs 医学-医药化学

CiteScore

9.60

自引率

14.80%

发文量

671

审稿时长

1 months

期刊介绍： Marine Drugs (ISSN 1660-3397) publishes reviews, regular research papers and short notes on the research, development and production of drugs from the sea. Our aim is to encourage scientists to publish their experimental and theoretical research in as much detail as possible, particularly synthetic procedures and characterization information for bioactive compounds. There is no restriction on the length of the experimental section.