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New polycyclic tetramate macrolactams from marine-derived Streptomyces sp SCSIO 40060
Zhang, Wenjun; Zhang, Guangtao; Zhang, Liping; Liu, Wei2; Jiang, Xiaodong1; Jin, Hongbo1; Liu, Zhiwen; Zhang, Haibo; Zhou, Aihua3; Zhang, Changsheng
Source PublicationTETRAHEDRON
AbstractPolycyclic 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.
KeywordMarine-derived Streptomyces sp SCSIO 40060 Genome mining Polycyclic tetramate macrolactams Absolute structure
Document Type期刊论文
Affiliation1.Chinese Acad Sci, South China Sea Inst Oceanol, Guangdong Key Lab Marine Mat Med, RNAM Ctr Marine Microbiol,CAS Key Lab Trop Marine, 164 West Xingang Rd, Guangzhou 510301, Guangdong, Peoples R China
2.Univ Chinese Acad Sci, 19 Yuquan Rd, Beijing 100049, Peoples R China
3.South China Sea Resource Exploitat & Protect Coll, State Key Lab Appl Microbiol Southern China, Guangzhou, Guangdong, Peoples R China
4.Jiangsu Univ, Pharm Sch, Xuefu Rd 301, Zhenjiang City 212013, Jiangsu, Peoples R China
Recommended Citation
GB/T 7714
Zhang, Wenjun,Zhang, Guangtao,Zhang, Liping,et al. New polycyclic tetramate macrolactams from marine-derived Streptomyces sp SCSIO 40060[J]. TETRAHEDRON,2018,74(47):6839, 6845.
APA Zhang, Wenjun.,Zhang, Guangtao.,Zhang, Liping.,Liu, Wei.,Jiang, Xiaodong.,...&Zhang, Changsheng.(2018).New polycyclic tetramate macrolactams from marine-derived Streptomyces sp SCSIO 40060.TETRAHEDRON,74(47),6839.
MLA Zhang, Wenjun,et al."New polycyclic tetramate macrolactams from marine-derived Streptomyces sp SCSIO 40060".TETRAHEDRON 74.47(2018):6839.
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