Archazolid A-15-O-beta-D-glucopyranosilde and iso-Archazolid B: Potent V-ATPase Inhibitory Polyketides from the Myxobacteria Cystobacter violaceus and Archangium gephyra

Autor(en): Horstmann, Nicole
Essig, Sebastian
Bockelmann, Svenja 
Wieczorek, Helmut 
Huss, Markus 
Sasse, Florenz
Menche, Dirk 
Stichwörter: (H+)-ATPASES; BINDS; Chemistry, Medicinal; CONFORMATION; H+-ATPASE; MEMBRANE; Pharmacology & Pharmacy; Plant Sciences; PROTON PUMPS; STEREOCHEMICAL DETERMINATION; STRUCTURAL ELUCIDATION; VACUOLAR-TYPE ATPASE
Erscheinungsdatum: 2011
Herausgeber: AMER CHEMICAL SOC
Enthalten in: JOURNAL OF NATURAL PRODUCTS
Band: 74
Ausgabe: 5
Startseite: 1100
Seitenende: 1105
Zusammenfassung: 
Two structurally novel analogues of the macrolides archazolids A and B, archazolid A-15-O-beta-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 IC50 values in the picomolar range, while only moderate activity was observed for glycoside S. iso-Archazolid B presents the most potent archazolid known.
ISSN: 01633864
DOI: 10.1021/np200036v

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