O

411'

411'

FIGURE 14.158 Biotransformation of (-)-ß-pinene (1') by Botrytis cinerea. (Modified from Farooq, A. et al., 2002. Z. Naturforsch., 57c: 686-690.)

As shown in Figure 14.159, (+)- (1) and (-)-ß -pinenes (1') were biotransformed by Aspergillus niger TBUYN-2 to give (+)-a-terpineol (34) and (+)-oleuropeyl alcohol (204) and their antipodes (34' and 204'), respectively. The hydroxylation process of a-terpineol (34) to oleuropeyl alcohol (204) was completely inhibited by 1-aminotriazole as cyt.P-450 inhibitor.

(-)-ß-Pinene (1') was at first biotransformed by Aspergillus niger TBUYN-2 to give (+)-trans-pinocarveol (2a') (274). (+)-trans-Pinocarveol (2a') was further transformed by three pathways: firstly, (+)-trans-pinocarveol (2a') was metabolized to (+)-pinocarvone (3'), (-)-3-isopinanone (413'), (+)-2a-hydroxy-3-pinanone (414'), and (+)-2a,5-dihydroxy-3-pinanone (415'). Secondly, (+)-trans-pinocarveol (2a') was metabolized to (+)-6ß-hydroxyfenchol (349ba') and thirdly (+)-trans-pinocarveol (2a') was metabolized to (-)-6ß,7-dihydroxyfenchol (412ba') via epoxide and diol as intermediates (Noma and Asakawa, 2005a) (Figure 14.160).

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Aromatherapy Ambiance

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