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Manoyl-Oxide Biotransformations with Filamentous Fungi

“…Other minor metabolites hydroxylated at C-11 (29, 3%), C-6 (30, 1%) or C-2 (31, 1%) were again isolated as in the biotransformation of jhanidiol (19) with the same fungus, as well as a 3 -hydroxy (37, 0.5%) and a 14,15-epoxy derivative (38, 0.6%). The non-isolation of the l ,2 ,18-triol (32) in this incubation, also indicated that this metabolite was directly formed by 2 -hydroxylation of jhanidiol (19), and excludes an alternative way via (20). In the case of the incubation with M. plumbeus of this substrate (20), the reduction at C-1, the main transformation with G. fujikuroi was not observed, and there was a preference for 6 -hydroxylation (30, 5%) or dihydroxylation of the vinyl group (39, 3%).…”

“…The non-isolation of the l ,2 ,18-triol (32) in this incubation, also indicated that this metabolite was directly formed by 2 -hydroxylation of jhanidiol (19), and excludes an alternative way via (20). In the case of the incubation with M. plumbeus of this substrate (20), the reduction at C-1, the main transformation with G. fujikuroi was not observed, and there was a preference for 6 -hydroxylation (30, 5%) or dihydroxylation of the vinyl group (39, 3%). As in the biotransformation of this substrate (20) by G. fujikuroi, other minor metabolites hydroxylated at the C-2 (31, 1%), C-3 (37, 1%) or C-11 (29, 2%), together with a 14,15-epoxy derivative (38, 1%), were isolated.…”

“…In the case of the incubation with M. plumbeus of this substrate (20), the reduction at C-1, the main transformation with G. fujikuroi was not observed, and there was a preference for 6 -hydroxylation (30, 5%) or dihydroxylation of the vinyl group (39, 3%). As in the biotransformation of this substrate (20) by G. fujikuroi, other minor metabolites hydroxylated at the C-2 (31, 1%), C-3 (37, 1%) or C-11 (29, 2%), together with a 14,15-epoxy derivative (38, 1%), were isolated. Two new 2 -hydroxy (40, 0.5%) or 3 -hydroxy derivatives (41, 1%) were also detected (Fig.…”

“…Other substrates subjected to screening [20] with hydroxylating fungi were forskolin (1) and 7-deacetylforskolin (3). With an Aspergillus sp.…”

“…The aim of these biotransformation processes was to get compounds with a functionalization similar to that of forskolin (1). The substrates employed were jhanol, (18) (18-hydroxymanoyl oxide) and jhanidiol (19), a 1 -hydroxyl derivative, both isolated from a Venezuelan plant [25], and 1-oxo-jhanol (20), a major metabolite obtained from the incubation of jhanidiol (19) with G. fujikuroi, or chemically from jhanol (18).…”