95457-15-1Relevant articles and documents
Biotransformation of 4β-hydroxyeudesmane-1,6-dione by Gliocladium roseum and Exserohilum halodes
García-Granados, Andrés,Gutiérrez, María C.,Rivas, Francisco,Arias, José M.
, p. 891 - 895 (2001)
Biotransformation of sesquiterpene 4β-hydroxyeudesmane-1,6-dione by the filamentous fungi Gliocladium roseum and Exserohilum halodes was achieved. With Exserohilum halodes, only one metabolite was obtained, as a result of the regio- and stereo-selective reduction of the keto group at C-1, which is difficult to achieve by chemical means. Five metabolites were produced with Gliocladium roseum, three of which, the 7α-hydroxylated, the 7α, 11- and the 1α,8α-dihydroxylated derivatives, have not previously been reported. The hydroxylation at C-11 is the main action of this microorganism. These 11-hydroxylated compounds can be chemically transformed into 6β.12-eudesmanolides.
Chemical-Microbiological Synthesis of 6β-Eudesmanolides from 11-Hydroxyl Derivatives obtained by Rhizopus nigricans cultures: Synthesis of 6β-Dendroserins.
Garcia-Granados, Andres,Martinez, Antonio,Parra, Andres,Rivas, Francisco,Onorato, M. Esther,Arias, Jose M.
, p. 1091 - 1102 (2007/10/02)
The relationship between the structure of the substrates and the action of the fungus Rhizopus nigricans has been studied in order to obtain, in the highest possible yield, 11-hydroxyl derivatives which were dehydrates to the "exo" position, hydroborated with 9-BBN and oxidized with RuH2(PPh3)4 to give 11-R and 11-S-6-epi-dendroserin.In course of the biotransformation processes, 8α-hydroxyl and 7α-hydroxyl derivatives were also obtained, as well as the oxidation of the hydroxyl groups at C-1, an unusual process with Rhizopus nigricans.We have proved that the eudesmanones are more easily hydroxylated at C-11 than the hydroxyeudesmane compounds.Key Words: Biotransformation; 6β-eudesmanolides; 11-hydroxyeudesmanes; Rhizopus nigricans
