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Molecules 2007, 12(5), 1092-1100; doi:10.3390/12051092
Article

Biotransformations of Imbricatolic Acid by Aspergillus niger and Rhizopus nigricans Cultures

1,* , 1, 3, 4 and 4
1 Laboratorio de Química de Productos Naturales, Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile 2 Current address: Centro de Investigación y Desarrollo de Recursos y Ambientes Costeros, Universidad de Los Lagos, Casilla 557, Puerto Montt, Chile 3 INTEQUI-CONICET, Laboratorio de Química Orgánica, Universidad Nacional de San Luis, Chacabuco y Pedernera 5700, San Luis, Argentina 4 Depto. de Ciencias Básicas Biomédicas, Facultad de Ciencias de la Salud, Universidad de Talca, Casilla 747, Talca, Chile
* Author to whom correspondence should be addressed.
Received: 20 April 2007 / Revised: 18 May 2007 / Accepted: 19 May 2007 / Published: 21 May 2007
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Abstract

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.
Keywords: Aspergillus niger; Rhizopus nigricans; imbricatolic acid; biotransformation; diterpene; Cunninghamella echinulata; mycophenolic acid Aspergillus niger; Rhizopus nigricans; imbricatolic acid; biotransformation; diterpene; Cunninghamella echinulata; mycophenolic acid
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Schmeda-Hirschmann, G.; Aranda, C.; Kurina, M.; Rodríguez, J.A.; Theoduloz, C. Biotransformations of Imbricatolic Acid by Aspergillus niger and Rhizopus nigricans Cultures. Molecules 2007, 12, 1092-1100.

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