The Khamkhains, Neurotrophic Drimane-Type Sesquiterpenoids Derived from a Polyporaceous Basidiomycete Originating from Thailand

IF 3.6 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2025-07-16 DOI:10.1021/acs.jnatprod.5c00669

Pathompong Paomephan, Khadija Hassan, Marco Kirchenwitz, Sebastian Pfütze, Frank Surup, Ivana Císařová, Chuenchit Boonchird* and Marc Stadler*,

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Abstract

Eight unprecedented terpenoids were isolated from submerged cultures of a polyporoid basidiomycete originating from Thailand (which had been referred to as “Cerrena sp.” in a previous publication) by preparative chromatography. Their chemical structures were elucidated by extensive two-dimensional nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry. One of the compounds was crystallized, and its absolute configuration was established by X-ray crystallography. Among the isolated metabolites were several members of the rare nitrogen-containing drimane type and one dimeric drimane, which consists of a nitrogen-containing monomer and a regular monomer. The latter compound represents a hitherto unknown type of terpenoid natural product. The metabolites were subjected to a biological characterization, and some of them showed significant neurotrophic effects. Notably, several of the compounds significantly enhanced the outgrowth of neurites in PC12 cells when treated with 5 ng/mL nerve growth factor. On the other hand, they were devoid of significant cytotoxic and antimicrobial effects.

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Khamkhains，源自泰国多孔担子菌的神经营养驱动型倍半萜类。

用制备色谱法从泰国的一种多孢子担子菌（在以前的出版物中被称为“Cerrena sp.”）的水中培养物中分离出8种前所未有的萜类化合物。它们的化学结构通过广泛的二维核磁共振（NMR）光谱和高分辨率质谱分析得以阐明。其中一种化合物结晶，并通过x射线晶体学确定了其绝对构型。在分离的代谢物中，有几种罕见的含氮驱动型和一种二聚体驱动型，它由一个含氮单体和一个规则单体组成。后一种化合物代表一种迄今未知的萜类天然产物。代谢产物进行了生物学表征，其中一些表现出显著的神经营养作用。值得注意的是，当用5 ng/mL神经生长因子处理PC12细胞时，其中一些化合物显著增强了神经突的生长。另一方面，它们没有明显的细胞毒性和抗菌作用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.