ABSTRACT
A new bacterium, Saccharopolyspora pogona (NRRL30141) was discovered which produced a series of very potent insecticidal compounds structurally related to the 'classical' (i.e., C-21-ethyl) spinosyns. A series of fermentations gave sufficient extract to allow the isolation and characterization of a total of 31 new metabolites. The majority of these compounds contained a but-1-enyl group at C-21 of the macrolide in place of the ethyl group in the 'classical' spinosyn series, corresponding to an additional acetate group incorporated during their biosynthesis. Additionally a variety of other new functionality was seen including hydroxylations, several novel forosamine sugar replacements, and a novel 14-membered macrolide ring analog.
Subject(s)
Insecticides/chemistry , Macrolides/chemistry , Saccharopolyspora/chemistry , Chromatography, Liquid , Drug Discovery , Fermentation , Insecticides/isolation & purification , Insecticides/pharmacology , Macrolides/isolation & purification , Macrolides/pharmacology , Mass SpectrometryABSTRACT
The ansacarbamitocins are a new family of maytansinoids that are unusually substituted with a glucose subunit and two carbamate functional groups and exhibit modest activity against some agricultural fungal disease organisms. Ansacarbamitocins A-F ( 1- 6) all consist of the same macrocyclic core as the ansamitocins, with variation occurring on the glucose unit, while ansacarbamitocins A1 and B1 ( 7, 8) additionally lack the epoxide group on C-4 and C-5.
Subject(s)
Actinomycetales/chemistry , Anti-Bacterial Agents/isolation & purification , Maytansine/analogs & derivatives , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/classification , Anti-Bacterial Agents/pharmacology , Ascomycota/drug effects , Maytansine/chemistry , Maytansine/classification , Maytansine/isolation & purification , Maytansine/pharmacology , Molecular Structure , Structure-Activity RelationshipABSTRACT
Several Penicillia and one Tricothecium strain produced a new, insecticidally active member of the cycloaspeptide family, with the proposed name cycloaspeptide E (1). The structure, which was determined on the basis of spectroscopic (NMR, UV, MS) data and Marfey amino acid analysis, was the tyrosine desoxy version of cycloaspeptide A (2). Two synthetic routes to compound 1 were developed: one a partial synthesis from 2 and the other a total synthesis from methyl alaninate hydrochloride. Cycloaspeptide E, the first member of this series not to contain a tyrosine moiety, is also the first to be reported with insecticidal activity.
