Activation and Identification of NC‐1: A Cryptic Cyclodepsipeptide from Red Soil‐Derived Streptomyces sp. FXJ1.172. Issue 23 (19th June 2016)

• Record Type: Journal Article
• Authors: Liu, Minghao; Liu, Ning; Shang, Fei; Huang, Ying
• Is Part Of: European journal of organic chemistry. Issue 23(2016)
• Page Start: 3943
• Page End: 3948
• Publication Date: 2016-06-19
• Subjects: Natural products -- Structure elucidation -- Configuration determination -- Depsipeptides -- Genome mining; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600297
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Genome sequence analysis of a lasalocid‐producing strain, Streptomyces sp. FXJ1.172, which was isolated from red soil, indicated its great untapped biosynthetic potential for novel secondary metabolites. A lasalocid‐null mutant Streptomyces sp. FXJ1.172Δ lodS, was then constructed to make way for the cryptic biosynthetic pathways. Consequently, a novel cyclodepsipeptide, named NC‐1, was activated and isolated from the lasalocid abolished mutant strain cultivated in glucose‐yeast extract‐malt extract (GYM) medium supplemented with ferric ion. The planar‐ and stereo‐structures of NC‐1 were elucidated based on detailed analyses of MS, NMR, and single‐crystal X‐ray diffraction data, revealing it as the first reported cyclodepsipeptide that is epoxidized at adjacent carbon atoms of the cinnamoyl fatty acid side chain. In assays of antimicrobial activity, NC‐1 exhibited moderate inhibition effects against Mycobacterium bovis bacille Calmette–Guérin (BCG). Abstract : A novel cyclodepsipeptide, NC‐1, was discovered from Streptomyces sp. FXJ1.172 by genome mining. It contains an entirely different amino acid composition in the core depsipeptide structure from the other cyclodepsipeptides as well as an epoxidized and longer alkyl side chain on the cinnamoyl group.