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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
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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