Cadinane-Type Sesquiterpenoids with Cytotoxic Activity from the Infected Stems of the Semi-mangrove Hibiscus tiliaceus

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2022-01-18 DOI:10.1021/acs.jnatprod.1c00849

De-Li Chen, Mei-Ying Chen, Yong Hou, Can-Hong Wang, Zhao-Cui Sun, Yun Yang, Han-Qiao Liang, Guo-Xu Ma*, Xu-Dong Xu*, Jian-He Wei*

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引用次数: 3

Abstract

Eight new cadinane sesquiterpenoids (1–8), along with two known compounds (9 and 10), were isolated from infected stems of the semi-mangrove plant, Hibiscus tiliaceus. The structures of compounds 1–8 were elucidated through the analysis of their 1D and 2D NMR and MS data, and their absolute configurations were determined by comparing their experimental and calculated ECD spectra and by single-crystal X-ray diffraction. The two confused known compounds (9 and 10) were resolved using single-crystal X-ray crystallography. Compounds 1–3 have novel norsesquiterpene carbon skeletons arising from a ring contraction rearrangement. All obtained isolates were evaluated against the HepG2 and Huh7 cell lines, and compounds 1b, 2b, 4, 6, and 8 showed cytotoxic activity toward both cell lines, with IC₅₀ values ranging from 3.5 to 6.8 μM.

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半红树芙蓉茎中具有细胞毒活性的cadine型倍半萜类化合物

从半红树林植物木槿(Hibiscus tiliaceus)的感染茎中分离出8个新的二苯胺倍半萜类化合物(1-8)和2个已知化合物(9和10)。通过对化合物1 ~ 8的1D和2D NMR和MS数据的分析，确定了化合物1 ~ 8的结构，并通过对比实验和计算ECD谱以及单晶x射线衍射确定了化合物1 ~ 8的绝对构型。两个混淆的已知化合物(9和10)用单晶x射线晶体学进行了分辨。化合物1-3具有由环收缩重排而产生的新型降倍半萜碳骨架。化合物1b、2b、4、6和8对HepG2和Huh7细胞系均表现出细胞毒活性，IC50值在3.5 ~ 6.8 μM之间。

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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.