Novel and potent gastrin and brain cholecystokinin antagonists from Streptomyces olivaceus. Taxonomy, fermentation, isolation, chemical conversions, and physico-chemical and biochemical properties.
J Antibiot (Tokyo)
; 44(6): 613-25, 1991 Jun.
Article
em En
| MEDLINE
| ID: mdl-1906451
ABSTRACT
The discovery and physico-chemical characterization of three novel and minor virginiamycin M1 analogs as potent gastrin antagonists from a culture of a strain of Streptomyces olivaceus are described. These analogs are L-156,586, L-156,587 and L-156,588. They are, respectively, 15-dihydro-13,14-anhydro-, 13,14-anhydro- and 13-desoxy-analogs of virginiamycin M1. We also chemically converted virginiamycin M1 (via L-156,587) to L-156,586 and its unnatural epimer, L-156,906. These analogs are competitive and selective antagonists of gastrin and brain cholecystokinin binding at nanomolar concentrations. These are the most potent gastrin/brain cholecystokinin antagonists from natural products. The same compounds showed poor Gram-positive antibiotic activity versus virginiamycin M1. Structurally related Gram-positive antibiotics, griseoviridin and madumycin I, were inactive in gastrin and brain cholecystokinin binding at up to 100 microM.
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Base de dados:
MEDLINE
Assunto principal:
Streptomyces
/
Colecistocinina
/
Gastrinas
/
Virginiamicina
Limite:
Animals
Idioma:
En
Revista:
J Antibiot (Tokyo)
Ano de publicação:
1991
Tipo de documento:
Article