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

DC Field Value Language
dc.contributor.authorHong, Seong-Heon-
dc.contributor.authorBan, Yeon Hee-
dc.contributor.authorByun, Woong Sub-
dc.contributor.authorKim, Donghwa-
dc.contributor.authorJang, Yong-Joon-
dc.contributor.authorAn, Joon Soo-
dc.contributor.authorShin, Bora-
dc.contributor.authorLee, Sang Kook-
dc.contributor.authorShin, Jongheon-
dc.contributor.authorYoon, Yeo Joon-
dc.contributor.authorOh, Dong-Chan-
dc.date.accessioned2024-08-08T01:29:52Z-
dc.date.available2024-08-08T01:29:52Z-
dc.date.created2019-09-30-
dc.date.created2019-09-30-
dc.date.issued2019-04-
dc.identifier.citationJournal of Natural Products, Vol.82 No.4, pp.903-910-
dc.identifier.issn0163-3864-
dc.identifier.urihttps://hdl.handle.net/10371/206264-
dc.description.abstractChemical 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. STAl. 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 H-1-H-1 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.-
dc.language영어-
dc.publisherAmerican Chemical Society-
dc.titleCamporidines A and B: Antimetastatic and Anti-inflammatory Polyketide Alkaloids from a Gut Bacterium of Camponotus kiusiuensis-
dc.typeArticle-
dc.identifier.doi10.1021/acs.jnatprod.8b01000-
dc.citation.journaltitleJournal of Natural Products-
dc.identifier.wosid000466442100025-
dc.identifier.scopusid2-s2.0-85065013062-
dc.citation.endpage910-
dc.citation.number4-
dc.citation.startpage903-
dc.citation.volume82-
dc.description.isOpenAccessN-
dc.contributor.affiliatedAuthorLee, Sang Kook-
dc.contributor.affiliatedAuthorShin, Jongheon-
dc.contributor.affiliatedAuthorYoon, Yeo Joon-
dc.contributor.affiliatedAuthorOh, Dong-Chan-
dc.type.docTypeArticle-
dc.description.journalClass1-
dc.subject.keywordPlusSECONDARY METABOLITE-
dc.subject.keywordPlusGENE-CLUSTER-
dc.subject.keywordPlusBIOSYNTHESIS-
dc.subject.keywordPlusDIHYDROABIKOVIROMYCIN-
dc.subject.keywordPlusIDENTIFICATION-
dc.subject.keywordPlusREVEALS-
dc.subject.keywordPlusPRODUCT-
dc.subject.keywordPlusGARDEN-
dc.subject.keywordPlusANTS-
dc.subject.keywordPlusSP.-
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  • College of Pharmacy
  • Department of Manufacturing Pharmacy
Research Area Chemical biology of natural products, Drug discovery from microbial natural products, Study of insect-microbial symbiosis, 미생물 유래 생리활성 천연물 발굴, 천연물 구조 분석

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