Archazolid A-15-O-β-D-glucopyranoside and iso-archazolid B: potent V-ATPase inhibitory polyketides from the myxobacteria Cystobacter violaceus and Archangium gephyra.

2.50
Hdl Handle:
http://hdl.handle.net/10033/620828
Title:
Archazolid A-15-O-β-D-glucopyranoside and iso-archazolid B: potent V-ATPase inhibitory polyketides from the myxobacteria Cystobacter violaceus and Archangium gephyra.
Authors:
Horstmann, Nicole; Essig, Sebastian; Bockelmann, Svenja; Wieczorek, Helmut; Huss, Markus; Sasse, Florenz; Menche, Dirk
Abstract:
Two structurally novel analogues of the macrolides archazolids A and B, archazolid A-15-O-β-D-glucopyranoside (archazolid E, 5) and iso-archazolid B (archazolid F, 6), were isolated from the myxobacterium Cystobacter violaceus and Archangium gephyra, respectively. Macrolactone 5 represents the first 15-O-glycoside of the archazolids. iso-Archazolid B (6) incorporates a C-3 alkene and presents the first constitutional isomer reported for this natural product class. The structures of these polyketides were determined by spectroscopic analysis, in particular by HMBC, HMQC, and ROESY NMR investigations and by chemical degradation. iso-Archazolid B (6) demonstrated extremely high antiproliferative and V-ATPase inhibitory effects, with IC(50) values in the picomolar range, while only moderate activity was observed for glycoside 5. iso-Archazolid B presents the most potent archazolid known.
Affiliation:
Helmholtz Centre for infection research, Inhoffenstr. 7, 38124 Braunschweig, Germany.
Citation:
Archazolid A-15-O-β-D-glucopyranoside and iso-archazolid B: potent V-ATPase inhibitory polyketides from the myxobacteria Cystobacter violaceus and Archangium gephyra. 2011, 74 (5):1100-5 J. Nat. Prod.
Journal:
Journal of natural products
Issue Date:
27-May-2011
URI:
http://hdl.handle.net/10033/620828
DOI:
10.1021/np200036v
PubMed ID:
21513292
Type:
Article
Language:
en
ISSN:
1520-6025
Appears in Collections:
Publications of the research group Chemical Biology (CBIO)

Full metadata record

DC FieldValue Language
dc.contributor.authorHorstmann, Nicoleen
dc.contributor.authorEssig, Sebastianen
dc.contributor.authorBockelmann, Svenjaen
dc.contributor.authorWieczorek, Helmuten
dc.contributor.authorHuss, Markusen
dc.contributor.authorSasse, Florenzen
dc.contributor.authorMenche, Dirken
dc.date.accessioned2017-02-17T14:34:39Z-
dc.date.available2017-02-17T14:34:39Z-
dc.date.issued2011-05-27-
dc.identifier.citationArchazolid A-15-O-β-D-glucopyranoside and iso-archazolid B: potent V-ATPase inhibitory polyketides from the myxobacteria Cystobacter violaceus and Archangium gephyra. 2011, 74 (5):1100-5 J. Nat. Prod.en
dc.identifier.issn1520-6025-
dc.identifier.pmid21513292-
dc.identifier.doi10.1021/np200036v-
dc.identifier.urihttp://hdl.handle.net/10033/620828-
dc.description.abstractTwo structurally novel analogues of the macrolides archazolids A and B, archazolid A-15-O-β-D-glucopyranoside (archazolid E, 5) and iso-archazolid B (archazolid F, 6), were isolated from the myxobacterium Cystobacter violaceus and Archangium gephyra, respectively. Macrolactone 5 represents the first 15-O-glycoside of the archazolids. iso-Archazolid B (6) incorporates a C-3 alkene and presents the first constitutional isomer reported for this natural product class. The structures of these polyketides were determined by spectroscopic analysis, in particular by HMBC, HMQC, and ROESY NMR investigations and by chemical degradation. iso-Archazolid B (6) demonstrated extremely high antiproliferative and V-ATPase inhibitory effects, with IC(50) values in the picomolar range, while only moderate activity was observed for glycoside 5. iso-Archazolid B presents the most potent archazolid known.en
dc.language.isoenen
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/4.0/*
dc.subject.meshAnimalsen
dc.subject.meshAntineoplastic Agentsen
dc.subject.meshDrug Screening Assays, Antitumoren
dc.subject.meshFemaleen
dc.subject.meshGlucosidesen
dc.subject.meshHumansen
dc.subject.meshInhibitory Concentration 50en
dc.subject.meshMacrolidesen
dc.subject.meshMaleen
dc.subject.meshMiceen
dc.subject.meshMolecular Structureen
dc.subject.meshMyxococcalesen
dc.subject.meshThiazolesen
dc.subject.meshVacuolar Proton-Translocating ATPasesen
dc.titleArchazolid A-15-O-β-D-glucopyranoside and iso-archazolid B: potent V-ATPase inhibitory polyketides from the myxobacteria Cystobacter violaceus and Archangium gephyra.en
dc.typeArticleen
dc.contributor.departmentHelmholtz Centre for infection research, Inhoffenstr. 7, 38124 Braunschweig, Germany.en
dc.identifier.journalJournal of natural productsen

Related articles on PubMed

This item is licensed under a Creative Commons License
Creative Commons
All Items in HZI are protected by copyright, with all rights reserved, unless otherwise indicated.