title: Rhizovarins A-F, Indole-Diterpenes from the Mangrove-Derived Endophytic Fungus Mucor irregularis QEN-189.
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.
authors.affiliation: Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences , Nanhai Road 7, Qingdao 266071, People's Republic of China.|School of Chemistry, University of Bristol , Bristol BS8 1TS, United Kingdom.
authors.forename: Shu-Shan
authors.initials: SS
authors.lastname: Gao
authors.affiliation: Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences , Nanhai Road 7, Qingdao 266071, People's Republic of China.
authors.forename: Xiao-Ming
authors.initials: XM
authors.lastname: Li
authors.affiliation: School of Chemistry, University of Bristol , Bristol BS8 1TS, United Kingdom.
authors.forename: Katherine
authors.initials: K
authors.lastname: Williams
authors.affiliation: Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf , Universitätsstraße 1, Geb. 26.23, 40225 Düsseldorf, Germany.
authors.forename: Peter
authors.initials: P
authors.lastname: Proksch
authors.affiliation: Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences , Chunhui Road 17, Yantai 264003, People's Republic of China.
authors.forename: Nai-Yun
authors.initials: NY
authors.lastname: Ji
authors.affiliation: Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences , Nanhai Road 7, Qingdao 266071, People's Republic of China.
authors.forename: Bin-Gui
authors.initials: BG
authors.lastname: Wang
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018922:HL-60 Cells; D006801:Humans; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D009089:Mucor / Q000737:chemistry*; D043982:Rhizophoraceae / Q000382:microbiology
chemical_list: D000970:Antineoplastic Agents; D004224:Diterpenes; D004365:Drugs, Chinese Herbal; D007211:Indoles