Cytotoxic Stilbenoids, Hetero- and Homodimers of Homoisoflavonoids from Prospero autumnale.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2025-02-28 Epub Date: 2025-01-24 DOI:10.1021/acs.jnatprod.4c01263

Hasan Kırmızıbekmez, Başak Aru, Jana Křoustková, Murat Erdoğan, Ian Torrence, Kaori Ando, Dean J Tantillo, Milan Malaník, Štefan Kosturko, Jiří Kuneš, Lucie Cahlíková

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引用次数: 0

Abstract

An activity-guided isolation study on the EtOH extract prepared from the bulbs of Prospero autumnale yielded four new phenolic compounds, including a new stilbenoid (1), a new homoisoflavonoid derivative (8), a new homoisoflavonoid dimer (9), and an unprecedented homoisoflavone-stilbene heterodimer (10), together with six known (2-7) analogs. Their chemical structures were elucidated by spectroscopic analysis and theoretical NMR and ECD calculations. Compounds 9 and 10 are unique in their scaffolds. The in vitro cytotoxic activity of purified compounds was evaluated against eight tumor cell lines (HCT116, LoVo, DU145, PC3, HEP3B, HEPG2, MCF7, and MDA-MB-231) and one nontumor cell line (L929) by the MTS assay. Compounds 1, 2, 4, and 10 exhibited inhibition with IC₅₀ values ranging from 8.2 to 37.6 μM. Cytotoxic cell death mechanisms were further investigated, indicating variability in apoptosis, necrosis, or cell cycle arrest.

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秋彼螺同型异黄酮的细胞毒性二苯乙烯类、异二聚体和同型二聚体。

从秋彼螺球茎中提取的乙醇提取物进行了活性引导分离研究，得到了4个新的酚类化合物，包括一个新的二苯乙烯类化合物(1)、一个新的同型异黄酮衍生物(8)、一个新的同型异黄酮二聚体(9)和一个前所未有的同型异黄酮-二苯乙烯异二聚体（10），以及6个已知的（2-7）类似物。它们的化学结构通过光谱分析和理论核磁共振和ECD计算得到。化合物9和10在它们的支架上是独一无二的。通过MTS实验评估纯化化合物对8种肿瘤细胞系（HCT116、LoVo、DU145、PC3、HEP3B、HEPG2、MCF7和MDA-MB-231）和1种非肿瘤细胞系（L929）的体外细胞毒活性。化合物1、2、4和10的IC50值在8.2 ~ 37.6 μM之间。进一步研究了细胞毒性细胞死亡机制，表明细胞凋亡、坏死或细胞周期停滞的可变性。

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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.