Discovery of undescribed anthracycline-derived polyketides with cytotoxicity from endophytic Streptomyces chartreusis M7

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry Pub Date : 2024-11-15 DOI:10.1016/j.phytochem.2024.114337

Zi Kang Meng , Si Min Rao , Yu Kai Hu , Xuan Zhou , Qian Yang , Ren Xiang Tan , Yi Shuang Wang

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Abstract

Endophytic actinomycetes exhibit considerable potential for the production of biologically active metabolites due to their coevolution with plant hosts. In this study, an endophytic Streptomyces chartreusis M7 was isolated from Houttuynia cordata Thunb. Bioactivity-guided investigation of the metabolites produced by this strain led to the identification of thirteen anthracycline-derived polyketides, including five unreported anthraquinones designated streptoquinones A-E (1–5) and two undescribed angular polyketides named chartins A and B (6–7) along with six knowns. Their structures were elucidated through comprehensive spectroscopic analysis and ECD calculations. Notably, chartins A (6) and B (7) feature angular tetracyclic and pentacyclic skeletons, respectively, which have undergone several oxidative rearrangements. Moreover, streptoquinone A (1) exhibited moderate cytotoxicity against A549 cells, with an IC₅₀ value of 4.8 μM.

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从内生链霉菌 Chartreusis M7 中发现具有细胞毒性的蒽环类衍生多酮。

内生放线菌与植物宿主共同进化，在生产具有生物活性的代谢物方面具有相当大的潜力。本研究从蕺菜（Houttuynia cordata Thunb）中分离出了一种内生链霉菌 Chartreusis M7。通过对该菌株产生的代谢产物进行生物活性指导调查，鉴定出 13 种蒽环类衍生多酮，包括 5 种未报道的蒽醌类化合物，命名为链醌 A-E（1-5），两种未描述的角状多酮，命名为 chartins A 和 B（6-7），以及 6 种已知的多酮。通过全面的光谱分析和 ECD 计算，这些化合物的结构得以阐明。值得注意的是，海图素 A（6）和 B（7）分别以角四环和五环骨架为特征，它们经历了多次氧化重排。此外，链醌 A（1）对 A549 细胞具有中等程度的细胞毒性，IC50 值为 4.8 μM。

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来源期刊

Phytochemistry 生物-植物科学

CiteScore

6.40

自引率

7.90%

发文量

443

审稿时长

39 days

期刊介绍： Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.