南非采集的药用植物 Melianthus comosus 的叶子中的细胞毒蟾蜍二烯内酯。
Cytotoxic bufadienolides from the leaves of a medicinal plant Melianthus comosus collected in South Africa.
机构信息
Department of Chemistry, Addis Ababa University, P.O. Box 33658, Addis Ababa, Ethiopia; Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, TU Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Germany.
Inorganic Chemistry, Department of Chemistry and Chemical Biology, TU Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Germany.
出版信息
Bioorg Chem. 2020 Sep;102:104102. doi: 10.1016/j.bioorg.2020.104102. Epub 2020 Jul 15.
From the leaves of South African medicinal plant Melianthus comosus, four previously undescribed bufadienolides, 16β-formyloxymelianthugenin (1), 2β-acetoxymelianthusigenin (2), 2β-hydroxy-3β,5β-di-O-acetylhellebrigenin (3), and 2β-acetoxy-5β-O-acetylhellebrigenin (4) were isolated together with two known bufadienolides. The structural elucidation of the compounds was based on 1D and 2D NMR spectroscopy, high-resolution mass spectrometry, and other spectroscopic methods. The relative configurations were determined by single-crystal X-ray crystallography analysis and NOESY correlations. The isolated compounds displayed strong cytotoxicity against MCF-7 breast cancer cells, sensitive CCRF-CEM and multidrug-resistant CEM/ADR5000 leukemia cells. Compound 1 showed the most potent activity, with IC values of 0.07 μM towards CCRF-CEM, 0.06 μM towards CEM/ADR5000 and 0.36 μM towards MCF-7 followed by compound 4 with IC values of 0.13 μM towards CCRF-CEM, 0.08 μM towards CEM/ADR5000 and 0.53 μM towards MCF-7.
从南非药用植物 Melianthus comosus 的叶子中，分离得到了四种以前未被描述的蟾蜍二烯内酯，16β-甲酰氧基美兰新苷元（1）、2β-乙酰氧基美兰他新苷元（2）、2β-羟基-3β,5β-二-O-乙酰基海蟾毒精（3）和 2β-乙酰氧基-5β-O-乙酰基海蟾毒精（4），以及两种已知的蟾蜍二烯内酯。化合物的结构鉴定基于 1D 和 2D NMR 光谱、高分辨率质谱和其他光谱方法。相对构型通过单晶 X 射线晶体学分析和 NOESY 相关确定。分离得到的化合物对 MCF-7 乳腺癌细胞、敏感的 CCRF-CEM 和多药耐药的 CEM/ADR5000 白血病细胞表现出强烈的细胞毒性。化合物 1 表现出最强的活性，对 CCRF-CEM 的 IC 值为 0.07 μM，对 CEM/ADR5000 的 IC 值为 0.06 μM，对 MCF-7 的 IC 值为 0.36 μM，其次是化合物 4，对 CCRF-CEM 的 IC 值为 0.13 μM，对 CEM/ADR5000 的 IC 值为 0.08 μM，对 MCF-7 的 IC 值为 0.53 μM。
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