Rhizovarins A–F, indole-diterpenes from the mangrove-derived endophytic fungus Mucor irregularis QEN-189

Shu-Shan Gao, Xiao-Ming Li, Katherine Williams, Peter Proksch, Nai-Yun Ji, Bin-Gui Wang

Research output: Contribution to journalArticle (Academic Journal)peer-review

49 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)2066-2074
Number of pages9
JournalJournal of Natural Products
Volume79
Issue number8
Early online date27 Jul 2016
DOIs
Publication statusPublished - 26 Aug 2016

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