O

Pénicillium sclerotiorum

HO OH -)-Herbertenediol (339)

' HO OH HO OH Mastigophorene A (340)

Pénicillium sclerotiorum

' HO OH HO OH Mastigophorene A (340)

' HO OH HO OH Mastigophorene B (341)

HO OH -)-Herbertenediol (339)

' HO OH HO OH Mastigophorene B (341)

FIGURE 15.99 Biotransformation of (-)-herbertenediol (339) by Penicillium sclerotiorum.

medium including Aspergillus niger gave four metabolites, 9b-hydroxy- (363, 27%), 9b,15-dihydroxy- (364, 1.7%), 10b-hydroxy- (365, 10.3%), and 9b,15-dihydroxy derivative (366, 12.6%). In this case, the stereospecificity of alcohol was observed, but the regiospecificity of alcohol moiety was not seen in this substrate (Furusawa et al., 2005b, 2006b) (Figure 15.104).

The biotransformation of spirostructural terpenoids was not carried out. £nt-1a-hydroxy-P-chamigrene (367) was inoculated in the same manner as described above to give three new metabolites (368-370), of which 370 was the major product (46.2% in isolated yield). The hydroxylation of vinyl methyl group has been known to be very common in the case of microbial and mammalian biotransformation (Furusawa et al., 2005, 2006) (Figure 15.105).

A. niger

No metabolites

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