Microbial transformations of Aryltetralone and Aryltetralin Lignans by Cunninghamella echinulata and Beauveria bassiana

Messiano, Gisele B. [UNESP]; Wijeratne, E. M. Kithsiri; Lopes, Lucia Maria Xavier [UNESP]; Gunatilaka, A. A. Leslie

doi:10.1021/np100607s

Microbial transformations of Aryltetralone and Aryltetralin Lignans by Cunninghamella echinulata and Beauveria bassiana

Date

2010

Authors

Messiano, Gisele B.

Wijeratne, E. M. Kithsiri

Lopes, Lucia Maria Xavier

Gunatilaka, A. A. Leslie

Type

Article

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Abstract

Microbiological transformation of the aryltetralone lignan (−)-8′-epi-aristoligone (1) with Cunninghamella echinulata ATCC 10028B afforded two known natural lignans, (−)-holostyligone (3) and (−)-arisantetralone (4). Incubation of the aryltetralin lignan (−)-isogalbulin (2), obtained by chemical transformation of 1, with C. echinulata ATCC 10028B afforded the known lignan aryltetralol (5) and seven new metabolites, (−)-8-hydroxyisogalbulin (6), (−)-7-methoxyisogalbulin (7), (−)-4′-O-demethyl-8-hydroxyisogalbulin (8), (−)-7-methoxy-8-hydroxyisogalbulin (9), (−)-4′-O-demethyl-7-methoxyisogalbulin (10), (−)-4′,5-O-didemethylcyclogalgravin (11), and (−)-4′-O-demethylcyclogalgravin (12). When 2 was subjected to biotransformation with Beauveria bassiana ATCC 7159, (−)-8-hydroxyisogalbulin (6) was the only isolable product. The structures of all new compounds were established by detailed analysis of their spectroscopic data.