Biotransformation of ent-Atisenes and ent-Beyerenes by Rhizopus nigricans and Fusarium moniliforme Cultures

• Published in: Journal of natural products (Washington, D.C.) Vol. 60; no. 2; pp. 86 - 92
• Main Authors: García-Granados, Andrés, Parra, Andrés, Arias, José María
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.02.1997; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Biological and medical sciences; CELL CULTURE; CHEMICAL STRUCTURE; Chemistry, Medicinal; CULTIVO DE CELULAS; CULTURE DE CELLULE; DERIVATIVES; DITERPENOIDE; DITERPENOIDS; DITERPENOS; ESPECTROMETRIA; ESTRUCTURA QUIMICA; Fundamental and applied biological sciences. Psychology; Fusarium moniliforme; GIBBERELLA FUJIKUROI; Growth, nutrition, metabolism, transports, enzymes. Molecular biology; Life Sciences & Biomedicine; METABOLISM; METABOLISME; METABOLISMO; METABOLITE; METABOLITES; METABOLITOS; Microbiology; Mycology; Pharmacology & Pharmacy; Plant Sciences; Rhizopus nigricans; RHIZOPUS STOLONIFER; Science & Technology; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; STRUCTURE CHIMIQUE; MICROBIOLOGICAL TRANSFORMATION; DITERPENOIDS; GIBBERELLA-FUJIKUROI; Hydroxylation; Rhizopus stolonifer; Phycomycetes; Metabolism; Fungi; Terpene; Enantiomer; Diterpene; Epoxidation; Fungi Imperfecti; Fusarium moniliforme; Ethylenic compound; Thallophyta
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np960426k

Microbial transformations of ent-atisene and ent-beyerene compounds were carried out using cultures of R. nigricans and F. moniliforme. Rhizopus nigricans metabolized all of the substrates, at higher yields than F. moniliforme, to give an ent-3β hydroxylation (60−65% for ent-atisenes and 80−85% for ent-beyerenes). Moreover, the double bond of the ent-beyerene skeleton was epoxidized by both fungi at lower yields (3−6%). Fusarium moniliforme produced a number of additional minor products by hydroxylation at other positions.