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Camporidines A and B: Antimetastatic and Anti-inflammatory Polyketide Alkaloids from a Gut Bacterium of Camponotus kiusiuensis

Title
Camporidines A and B: Antimetastatic and Anti-inflammatory Polyketide Alkaloids from a Gut Bacterium of Camponotus kiusiuensis
Authors
Hong S.-H.Ban Y.H.Byun W.S.Kim D.Jang Y.-J.An J.S.Shin B.Lee S.K.Shin J.Yoon Y.J.Oh D.-C.
Ewha Authors
윤여준반연희
SCOPUS Author ID
윤여준scopus; 반연희scopus
Issue Date
2019
Journal Title
Journal of Natural Products
ISSN
0163-3864JCR Link
Citation
Journal of Natural Products vol. 82, no. 4, pp. 903 - 910
Publisher
American Chemical Society
Indexed
SCIE; SCOPUS WOS scopus
Document Type
Article
Abstract
Chemical studies of gut bacteria of the carpenter ant Camponotus kiusiuensis led to the discovery of two new alkaloids, camporidines A and B (1 and 2), from Streptomyces sp. STA1. The structures of 1 and 2 were established as new polyketide alkaloids bearing a piperidine-cyclopentene-epoxide 6/5/3 tricyclic system based on NMR spectroscopic and mass spectrometric analysis. The relative configurations of the camporidines were determined by their 1 H- 1 H NOESY/ROESY and 1D NOE NMR correlations. The experimental ECD spectra of 1 and 2 were compared with their calculated ECD spectra to assign their absolute configurations. Camporidine A (1) displayed antimetastatic activity by suppression of cell invasion against the metastatic breast cancer cell line MDA-MB-231 and showed an anti-inflammatory effect by suppressing nitric oxide production induced by lipopolysaccharide. In addition, the putative biosynthetic gene cluster of the camporidines was identified, and the biosynthetic pathway of the camporidines was proposed based on bioinformatic analysis of the full genome of Streptomyces sp. STA1. Camporidines A and B (1 and 2) could be biosynthesized by a modular type I PKS containing an acyl transferase domain that accepts an unusual extender unit, which becomes the (C1′-C6′) hexyl side chain. The post-PKS modification enzymes were predicted to perform an amination and an oxidation along with spontaneous Schiff base formation and generate the unique piperidine-cyclopentene-epoxide 6/5/3 tricyclic framework. © 2019 American Chemical Society and American Society of Pharmacognosy.
DOI
10.1021/acs.jnatprod.8b01000
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자연과학대학 > 화학·나노과학전공 > Journal papers
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