Ochrindoles A-D: New Bis-Indolyl Benzenoids from the Sclerotia of Aspergillus ochraceus NRRL 3519

Four new prenylated bis-indolyl benzenoid metabolites (ochrindoles A-D; 1-4) were isolated from antiinsectan organic extracts of the sclerotia of Aspergillus ochraceus (NRRL 3519). The structures of these compounds were determined primarily through HMBC, selective INEPT, and NOESY experiments. These...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1994-05, Vol.57 (5), p.634-639
Main Authors: de Guzman, Florecita S, Bruss, Dan R, Rippentrop, Jonathan M, Gloer, Katherine B, Gloer, James B, Wicklow, Donald T, Dowd, Patrick F
Format: Article
Language:English
Subjects:
Animals
ANTIBACTERIAL PROPERTIES
ANTIMICROBIAL PROPERTIES
ASPERGILLUS OCHRACEUS
Aspergillus ochraceus - metabolism
Bacillus subtilis - drug effects
BENCENO
BENZENE
CARPOPHILUS HEMIPTERUS
CHEMICAL COMPOSITION
COMPOSICION QUIMICA
COMPOSITION CHIMIQUE
CONTROL DE INSECTOS
Depression, Chemical
DERIVATIVES
ESPECTROMETRIA
Feeding Behavior - drug effects
HELICOVERPA ZEA
INDOL
INDOLES
Indoles - isolation & purification
Indoles - pharmacology
INSECT CONTROL
INSECT PESTS
Insecta
INSECTE NUISIBLE
INSECTICIDAL PROPERTIES
INSECTICIDAS
INSECTICIDE
INSECTICIDES
Insecticides - isolation & purification
INSECTOS DANINOS
LUTTE ANTIINSECTE
Magnetic Resonance Spectroscopy
METABOLITE
METABOLITES
METABOLITOS
MOLECULAR CONFORMATION
MOLECULAR STRUCTURE
PEST INSECTS
PROPIEDADES ANTIMICROBIANAS
PROPRIETE ANTIMICROBIENNE
SPECTRAL ANALYSIS
SPECTROMETRIE
SPECTROMETRY
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Description
Summary:Four new prenylated bis-indolyl benzenoid metabolites (ochrindoles A-D; 1-4) were isolated from antiinsectan organic extracts of the sclerotia of Aspergillus ochraceus (NRRL 3519). The structures of these compounds were determined primarily through HMBC, selective INEPT, and NOESY experiments. These compounds displayed moderate activity in feeding assays against the corn earworm Helicoverpa zea and the driedfruit beetle Carpophilus hemipterus. Compounds 1-4 also exhibited activity against Gram-positive bacteria.
ISSN:0163-3864
1520-6025
DOI:10.1021/np50107a011