Rhizovarins A-F, Indole-Diterpenes from the Mangrove-Derived Endophytic Fungus Mucor irregularis QEN-189
Rhizovarins A-F, Indole-Diterpenes from the Mangrove-Derived Endophytic Fungus Mucor irregularis QEN-189
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来自红树林内生真菌不规则毛霉 QEN-189 的根变体 A-F、吲哚二萜
DOI：
10.1021/acs.jnatprod.6b00403
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发表时间：
2016-08-01
影响因子：
5.1
通讯作者：
Wang, Bin-Gui
中科院分区：
文献类型：
--
作者：
Gao, Shu-Shan;Li, Xiao-Ming;Wang, Bin-Gui
真菌Mucor irregularis（以前称为Rhizomucor variabilis）的基因组挖掘揭示了次级代谢物生物合成的各种基因簇的存在，包括几个萜烯基簇。对从海生红树林植物茎柱根霉（Rhizophora stylosa）新鲜内部组织中分离的内生真菌M. irregularis QEN-189的化学多样性进行了研究，发现了20种结构多样的吲哚二萜，其中包括6个新化合物，即rhizovarins A-F（1-6）。其中，化合物1-3是已报道的吲哚-二萜中最复杂的成员。在前所未有的4,6,6,8,5,6,6,6,6-吲哚-二萜环体系中，不寻常的缩醛与半晶(1)或缩醛（2和3）相连，使它们在化学上独一无二。通过光谱分析、改进的Mosher法和化学计算，确定了它们的结构和绝对构型。每个分离的化合物对HL-60和A-549细胞株的抗肿瘤活性进行了评价。
Genome mining of the fungus Mucor irregularis (formerly known as Rhizomucor variabilis) revealed the presence of various gene clusters for secondary metabolite biosynthesis, including several terpene-based clusters. Investigation into the chemical diversity of M. irregularis QEN-189, an endophytic fungus isolated from the fresh inner tissue of the marine mangrove plant Rhizophora stylosa, resulted in the discovery of 20 structurally diverse indole-diterpenes including six new compounds, namely, rhizovarins A-F (1-6). Among them, compounds 1-3 represent the most complex members of the reported indole-diterpenes. The presence of an unusual acetal linked to a hemiketal (1) or a ketal (2 and 3) in an unprecedented 4,6,6,8,5,6,6,6,6-fused indole-diterpene ring system makes them chemically unique. Their structures and absolute configurations were elucidated by spectroscopic analysis, modified Mosher's method, and chemical calculations. Each of the isolated compounds was evaluated for antitumor activity against HL-60 and A-549 cell lines.