FIGURE 14.180 Biotransformation of (+)-fenchol (11a) by Aspergillus niger TBUYN-2, Aspergillus cellulosae IFO 4040, and the larvae of common cutworm, Spodptera litura. (Modified from Miyazawa, M. and Y. Miyamoto, 2004. Tetrahadron, 60: 3091-3096; Noma, Y. and Y. Asakawa, 2005a. Book of Abstracts of the 36th ISEO, p. 32.)
The larvae of common cutworm, Spodoptera litura, converted (+)-fenchol (11a) to (+)-10-hydroxy-fenchol (467a), (+)-8-hydroxyfenchol (465a), (+)-6ß -hydroxyfenchol (349ab), and (-)-9-hydroxy-fenchol (466a) (Miyazawa and Miyamoto, 2004) (Figure 14.180).
(+)-trans-Pinocarveol (2), which was formed from (-)-ß-pinene (1), was metabolized by Aspergillus niger TBUYN-2 to 6ß-hydroxy- (+)-fenchol (349ab) and 6ß,7-dihydroxy-(+)-fenchol (412ba'). (-)-Fenchone (12) was also metabolized to 6a-hydroxy- (13b) and 6ß-hydroxy- (-)-fenchone (13a). (+)-Fenchol (11) was metabolized to 6ß-hydroxy-(+)-fenchol (349ab) by Aspergillus niger TBUYN-2. Relationship of the metabolisms of (+)-trans-pinocarveol (2), (-)-fenchone (12), and (+)-fenchol (11) by Aspergillus niger TBUYN-2 is shown in Figure 14.181 (Noma and Asakawa 2005a).
(+)-a-Fencyl acetate (11a-Ac) was metabolized by Glomerella cingulata to give (+)-5-ß-hydroxy-a-fencyl acetate (350a-Ac, 50%) as the major metabolite and (+)-fenchol (11a, 20%) as the minor metabolite (Miyazato and Miyazawa 1999). On the other hand, (-)-a-fencyl acetate (11a'-Ac) was metabolized to (-)-5-ß-hydroxy-a-fencyl acetate (350a'-Ac, 70%) and (-)-fenchol (11a', 10%) as the minor metabolite by Glomerella cingulata (Miyazato and Miyazawa, 1999) (Figure 14.182).
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