The first hydroxylated archazolid from the myxobacterium Cystobacter violaceus: isolation, structural elucidation and V-ATPase inhibition.
The novel macrocyclic polyketide, 10-hydroxymethyl-archazolid-7-O-beta-D-glucopyranoside (archazolid D), was obtained from the myxobacterium Cystobacter violaceus. The structure of this first hydroxylated archazolid was determined by spectroscopic analysis, in particular by HMBC, HMQC, and ROESY NMR investigations, and by degradation. This novel metabolite was evaluated for growth inhibition of murine connective tissue cells and V-ATPase inhibition in comparison to other known archazolids.
Menche
Dirk
D
Helmholtz-Zentrum für Infektionsforschung GmbH, Medicinal Chemistry and Chemical Biology, Braunschweig, Germany. dirk.menche@helmoltz-hzi.de
Hassfeld
Jorma
J
Steinmetz
Heinrich
H
Huss
Markus
M
Wieczorek
Helmut
H
Sasse
Florenz
F
D000818:Animals; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002851:Chromatography, High Pressure Liquid; D004791:Enzyme Inhibitors / Q000302:isolation & purification / Q000494:pharmacology*; D005285:Fermentation; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D018402:Manduca / Q000201:enzymology; D051379:Mice; D009231:Myxococcales / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D025262:Vacuolar Proton-Translocating ATPases / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D025262:Vacuolar Proton-Translocating ATPases