O

149b'

149b'

FIGURE 14.126 Chemical structures of substrate reduced by the recombinant pulegone reductase and the transformed Esherichia coli cells.

14.3.4.1.5 Piperitenone and Isopiperitenone

Piperitenone (112) is metabolized to 5-hydroxypiperitenone (117), 7-hydroxypiperitenone (118), and 7,8-dihydroxypiperitone (157). Isopiperitenol (110) is reduced to give isopiperitenone (111), which is further metabolized to piperitenone (112), 7-hydroxy- (113), 10-hydroxy- (115), 4-hydroxy- (114), and 5-hydroxy-isopiperitenone (116). Compounds 111 and 112 are isomerized to each other. Pulegone (119) was metabolized to 112, 8,9-dehydromenthenone (120) and 8-hydroxymenthenone (121) as shown in the biotransformation of the same substrate using Botrytis allii (Miyazawa et al., 1991b) (Figure 14.127).

H. isolate (UOFS Y-0067) reduced (4S)-isopiperitenone (111) to (3tf,4S)-isopiperitenol (110), a precursor of (-)-menthol (137b) (van Dyk et al., 1998) (Figure 14.128).

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