期刊
TETRAHEDRON
卷 74, 期 47, 页码 6839-6845出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.10.007
关键词
Marine-derived Streptomyces sp SCSIO 40060; Genome mining; Polycyclic tetramate macrolactams; Absolute structure
资金
- NSFC [31630004]
- Administration of Ocean and Fisheries of Guangdong Province [A201601C02]
- Science and Technology Program of Guangzhou [201707010181]
- Chinese Academy of Sciences [XDA11030403, QYZDJ-SSW-DQC004]
Polycyclic tetramate macrolactams (PTMs) are widely distributed in nature and are generated from a compact biosynthetic pathway. Bioinformatics analysis of the draft genome sequence of marine-derived Streptomyces sp. SCSIO 40060 revealed the presence of a putative PTM-encoding biosynthetic gene cluster (BGC). Comparison of this PTM BGC with those from the databank by genome mining suggests that Streptomyces sp. SCSIO 40060 should produce PTMs with a 5/6/5 type of carbocyclic ring. Subsequently, a 40-L scale of cultivation of Streptomyces sp. SCSIO 40060 led to the isolation and characterization of four known PTMs, ikarugamycin (1), epoxyikarugamycin (2), capsimycin (3), capsimycin C (4), and three new PTMs, hydroxyikarugamycins A-C (5-7). The planar structures of 5-7 were assigned by comprehensive spectroscopic analysis and the absolute configurations of 5 and 6 were unequivocally determined by X-ray diffraction analysis. The absolute structure of 7 was deduced by comparing ECD spectra of 5-7. Capsimycin (3) showed antimicrobial activity against methicillin-resistant Staphylococcus aureus with a MIC value of 16 mu g/mL and displayed cytotoxicity against several cancer cell lines with IC50 values ranging from 2.62 to 6.87 mu M. (C) 2018 Elsevier Ltd. All rights reserved.
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