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Title

Biotransformation of an africanane sesquiterpene by the fungus Mucor plumbeus

AuthorsFraga, Braulio M. ; Díaz, Carmen E. ; Amador, Leonardo J.; Reina, Matías ; López-Rodríguez, Matías; González-Coloma, Azucena
KeywordsBiotransformations
Cytotoxic effects
Insect antifeedants
Africanane
Sesquiterpenes
Mucor plumbeus
Issue DateMar-2017
PublisherElsevier
CitationPhytochemistry 135: 73-79 (2017)
AbstractBiotransformation of 8β-hydroxy-african-4(5)-en-3-one angelate by the fungus Mucor plumbeus afforded as main products 6α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate and 1α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate, which had been obtained, together with the substrate, from transformed root cultures of Bethencourtia hermosae. This fact shows that the enzyme system involved in these hydroxylations in both organisms, the fungus and the plant, acts with the same regio- and stereospecificity. In addition another twelve derivatives were isolated in the incubation of the substrate, which were identified as the (2′R,3′R)- and (2′S,3′S)-epoxy derivatives of the substrate and of the 6α- and 1α-hydroxy alcohols, the 8β-(2′R,3′R)- and 8β-(2′S,3′S)-epoxyangelate of 8β,15-dihydroxy-african-4(5)-en-3-one, the hydrolysis product of the substrate, and three isomers of 8β-hydroxy-african-4(5)-en-3-one 2ξ,3ξ-dihydroxy-2-methylbutanoate. The insect antifeedant effects of the pure compounds were tested against chewing and sucking insect species along with their selective cytotoxicity against insect (Sf9) and mammalian (CHO) cell lines.
Publisher version (URL)https://doi.org/10.1016/j.phytochem.2016.12.015
URIhttp://hdl.handle.net/10261/185089
DOIhttp://dx.doi.org/10.1016/j.phytochem.2016.12.015
ISSN0031-9422
E-ISSN1873-3700
Appears in Collections:(ICA) Artículos
(IPNA) Artículos
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