Biotransformations of Imbricatolic Acid by Aspergillus niger and Rhizopus nigricans Cultures

Molecules

Guillermo Schmeda-Hirschmann¹  Carlos Aranda¹  Marcela Kurina³  Jaime A. Rodríguez² 

[1] Laboratorio de Química de Productos Naturales, Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile;Depto. de Ciencias Básicas Biomédicas, Facultad de Ciencias de la Salud, Universidad de Talca, Casilla 747, Talca, Chile;INTEQUI-CONICET, Laboratorio de Química Orgánica, Universidad Nacional de San Luis, Chacabuco y Pedernera 5700, San Luis, Argentina

关键词: Aspergillus niger;    Rhizopus nigricans;    imbricatolic acid;    biotransformation;    diterpene;    Cunninghamellaechinulata;    mycophenolic acid;   

DOI  :  10.3390/12051092

来源: mdpi

【 摘 要 】

Microbial transformation of imbricatolic acid (1) by Aspergillus niger afforded 1α-hydroxyimbricatolic acid (2), while transformation with Rhizopus nigricans yielded 15-hydroxy-8,17-epoxylabdan-19-oic acid (3). When the diterpene 1 was added to a Cunninghamella echinulata culture, the main products were the microbial metabolites mycophenolic acid (4) and its 3-hydroxy derivative 5. All the structures were elucidated by spectroscopic methods. The cytotoxicity of these compounds towards human lung fibroblasts and AGS cells was assessed. While 4 and 5 showed low cytotoxicity, with IC₅₀ values > 1000 µM against AGS cells and fibroblasts, 1α-hydroxyimbricatolic acid (2) presented moderate toxicity towards these targets, with IC₅₀ values of 307 and 631 µM, respectively. The structure of 2 is presented for the first time.

【 授权许可】

Unknown   
© 2007 by MDPI (http://www.mdpi.org).