Microbial transformations of aryltetralone and aryltetralin lignans by Cunninghamella echinulata and Beauveria bassiana

  • J Nat Prod. 2010 Nov 29;73(11):1933-7. doi: 10.1021/np100607s.
Gisele B Messiano  1 ,  E M Kithsiri Wijeratne ,  Lucia M X Lopes ,  A A Leslie Gunatilaka
Affiliations
  • 1. SW Center for Natural Products Research and Commercialization, Office of Arid Lands Studies, School of Natural Resources and the Environment, College of Agriculture and Life Sciences, University of Arizona, 250 E. Valencia Road, Tucson, Arizona 85706-6800, United States.
PMID: 20961092 DOI: 10.1021/np100607s
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.

Products