Chromones Featuring a [6,6]-Spiroketal Moiety Produced by Coculture of the Endophytic Fungi Chaetomium virescens and Xylaria Grammica.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2025-01-24 Epub Date: 2024-12-17 DOI:10.1021/acs.jnatprod.4c00773

Sitian Zhang, Nanjing Ding, Xinyu Zheng, Yuling Lu, Jiangchun Wei, Hanxiao Zeng, Weiguang Sun, Yuan Zhou, Ya Gao, Yonghui Zhang, Zhengxi Hu

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Abstract

Under the guidance of HPLC-DAD analysis, ten new chromones featuring a rare [6,6]-spiroketal moiety, namely chaetovirexylariones A-J (1-10), together with two known congeners (11-12), were isolated from coculture of the endophytic fungi Chaetomium virescens and Xylaria grammica, from the rhizome of the medicinal plant Smilax glabra Roxb. Their structures were elucidated via a combination of NMR and HRESIMS data, and the absolute configurations of 1-10 were determined by the chemical conversion and single-crystal X-ray diffraction (Cu Kα) experiments, as well as the comparison of the experimental and calculated electronic circular dichroism (ECD) data. Compound 6 is the first report as a racemate of this type of natural product. Compound 10 represents the first example of a [6,6]-spiroketal chromone bearing a 5-amino-3-methyl-2-pentenoic acid fragment. Compound 8 demonstrated a reduction in PTX resistance of SW620/AD300 by a factor of 45, and had the potential to be an effective P-gp inhibitor and an antitumor chemotherapy sensitizer.

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含有[6,6]-螺旋体片段的内生真菌绿毛毛菌和Grammica Xylaria共培养的色素

在HPLC-DAD分析的指导下，从药用植物菝葜根茎内生真菌Chaetomium virescens和Xylaria grammica共培养中分离出10个具有罕见[6,6]-螺旋体片段的新染色体chaetovirexylariones a - j（1-10）和2个已知同源基因（11-12）。结合核磁共振和HRESIMS数据对它们的结构进行了分析，并通过化学转化和单晶x射线衍射（Cu Kα）实验，以及实验和计算的电子圆二色性（ECD）数据的比较，确定了1-10的绝对构型。化合物6是首次报道的这种天然产物的外消旋体。化合物10是含有5-氨基-3-甲基-2-戊酸片段的[6,6]-螺旋酮色素的第一个例子。化合物8可将SW620/AD300的PTX耐药性降低45倍，有可能成为有效的P-gp抑制剂和抗肿瘤化疗增敏剂。

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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.