title: New isofuranonaphthoquinones and isoindolequinones from Streptomyces sp. CB01883.
abstract: Isofuranonaphthoquinones (IFQs) and Isoindolequinones (IIQs) comprise a small family of natural products, with the latter ones are especially uncommon in nature. Here we report the discovery of seven new IFQs, IFQ A-G (1-7), and three new IIQs, IIQ A-C (8-10), along with the known anthraquinone desoxyerythrolaccin (11), from Streptomyces sp. CB01883, expanding the chemical diversity of this family of natural products. The structures of these natural products were established on the basis of their HR-ESI-MS and nuclear magnetic resonance (NMR) spectroscopic data. All compounds were assessed for antibacterial activity, with 11 and 1, 5-7 exhibiting moderate and weak activities, respectively, against several Gram-positive bacteria tested. Bioinformatics analysis of the Streptomyces sp. CB01883 genome revealed the ifq gene cluster that showed identical genetic organization, with high-sequence identity, to the ifn gene cluster recently cloned from Streptomyces sp. RI-77 and confirmed to encode the biosynthesis of two IFQs, JBIR-76 and JBIR-77. Co-isolation of IFQs with IIQs from Streptomyces sp. CB01883 and facile chemical transformation of selected IFQs to IIQs, as exemplified by 1 to 9, together with the finding of the ifq cluster that most likely only encodes IFQ biosynthesis, support the proposal that IIQs may be derived nonenzymatically from IFQs in the presence of an amine.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, Jupiter, FL, USA.|Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Hainan, China.
authors.forename: Zhikai
authors.initials: Z
authors.lastname: Guo
authors.affiliation: Department of Chemistry, The Scripps Research Institute, Jupiter, FL, USA.
authors.forename: Guohui
authors.initials: G
authors.lastname: Pan
authors.affiliation: Department of Chemistry, The Scripps Research Institute, Jupiter, FL, USA.
authors.forename: Zhengren
authors.initials: Z
authors.lastname: Xu
authors.affiliation: Department of Chemistry, The Scripps Research Institute, Jupiter, FL, USA.
authors.forename: Dong
authors.initials: D
authors.lastname: Yang
authors.affiliation: Department of Chemistry, The Scripps Research Institute, Jupiter, FL, USA.
authors.lastname: Hindra
authors.affiliation: Xiangya International Academy of Translational Medicine, Central South University, Hunan, China.|Hunan Engineering Research Center of Combinatorial Biosynthesis and Natural Product Drug Discovery, Hunan, China.
authors.forename: Xiangcheng
authors.initials: X
authors.lastname: Zhu
authors.affiliation: Xiangya International Academy of Translational Medicine, Central South University, Hunan, China.
authors.forename: Yong
authors.initials: Y
authors.lastname: Huang
authors.affiliation: Yunnan Institute of Microbiology, Yunnan University, Yunnan, China.
authors.forename: Li-Xing
authors.initials: LX
authors.lastname: Zhao
authors.affiliation: Yunnan Institute of Microbiology, Yunnan University, Yunnan, China.
authors.forename: Yi
authors.initials: Y
authors.lastname: Jiang
authors.affiliation: Xiangya International Academy of Translational Medicine, Central South University, Hunan, China.|Hunan Engineering Research Center of Combinatorial Biosynthesis and Natural Product Drug Discovery, Hunan, China.
authors.forename: Yanwen
authors.initials: Y
authors.lastname: Duan
authors.affiliation: Department of Chemistry, The Scripps Research Institute, Jupiter, FL, USA.|Department of Molecular Therapeutics, The Scripps Research Institute, Jupiter, FL, USA.|Natural Products Library Initiative at The Scripps Research Institute, The Scripps Research Institute, Jupiter, FL, USA.
authors.forename: Ben
authors.initials: B
authors.lastname: Shen
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification; D019295:Computational Biology; D004926:Escherichia coli / Q000187:drug effects; D005285:Fermentation; D006094:Gram-Positive Bacteria / Q000187:drug effects; D045563:Indolequinones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D005810:Multigene Family / Q000235:genetics; D009285:Naphthoquinones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D021241:Spectrometry, Mass, Electrospray Ionization; D013302:Streptomyces / Q000737:chemistry* / Q000145:classification
chemical_list: D000900:Anti-Bacterial Agents; D001688:Biological Products; D045563:Indolequinones; D009285:Naphthoquinones