Biotransformation of 2 alpha, 5 alpha, 10 beta, 14 beta-tetraacetoxy-4(20),11-taxadiene by the fungi Cunninghamella elegans and Cunninghamella echinulata

• Published in: Journal of natural products (Washington, D.C.) Vol. 59; no. 11; pp. 1006 - 1009
• Main Authors: Hu, S.H. (Chinese Academy of Medical Sciences, Beijing, China.), Tian, X.F, Zhu, W.H, Fang, Q.C
• Format: Journal Article
• Language: English
• Published: CINCINNATI AMER SOC PHARMACOGNOSY 01.11.1996
• Subjects: AGENTES ANTINEOPLASTICOS; ANTINEOPLASTIC AGENTS; CHEMICAL STRUCTURE; Chemistry, Medicinal; CULTURE MEDIA; CUNNINGHAMELLA; Cunninghamella echinulata; Cunninghamella elegans; DITERPENOIDE; DITERPENOIDS; DITERPENOS; DRUG PLANTS; ESPECTROMETRIA; ESTRUCTURA QUIMICA; Life Sciences & Biomedicine; MEDICAMENT CYTOSTATIQUE; MEDIO DE CULTIVO; METABOLISM; METABOLISME; METABOLISMO; METABOLITE; METABOLITES; METABOLITOS; MILIEU DE CULTURE; Pharmacology & Pharmacy; Plant Sciences; PLANTAS MEDICINALES; PLANTE MEDICINALE; Science & Technology; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; STRUCTURE CHIMIQUE; TAXANES; TAXOL METABOLISM; 6-ALPHA-HYDROXYTAXOL; TAXANES; IDENTIFICATION
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np960112x

The biotransformations of the taxane diterpene 2 alpha,5 alpha,10 beta,14 beta-tetraacetoxy-4(20),11-taxadiene (1) by the fungi Cunninghamella elegans AS 3 . 2033 and Cunninghamella echinulata AS 3 . 1990 were investigated. Incubation of compound 1 with C. elegans afforded three new hydroxylated derivatives: 5 alpha,10 beta-dihydroxy-2 alpha,6 alpha,14 beta-triacetoxy-4(20),11-taxadiene (2), 6 alpha-hydroxy-2 alpha,5 alpha,10 beta,14 beta-tetraacetoxy-4-(20),11-taxadiene (3), and 5 alpha,6 alpha,10 beta-diacetoxy-4(20),11-taxadiene (4). The two new taxane metabolites, 5 alpha,10 beta,14 beta-trihydroxy-2 alpha-acetoxy-4(20),11-taxadiene (5) and 5 alpha,6 alpha,10 beta,14 beta-tetrahydroxy-2 alpha-acetoxy-4(20),11-taxadiene (6), were isolated from the incubation supernatant of C. echinulata with compound 1.