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FIGURE 14.130 Biotransformation of (+)-carvone (93), (-)-isodihydrocarvone (101b), and (-)-cw-limonene-1,2-epoxide (69b) by Aspergillus niger TBUYN-2 and Aspergillus niger Tiegh (CBAYN). (Modified from Noma, Y. et al., 1985a. Annual Meeting of Agricultural and Biological Chemistry, Sapporo, p. 68; Noma, Y. and Y. Asakawa, 2008. Proc. 52nd TEAC, pp. 206-208.)

by Pseudomonas fluorescens M-2 to (-)-3-oxo-4-isopropyl-1-cyclohexanecarboxylic acid (164a), (+)-3-oxo-4-isopropyl-1-cyclohexanecarboxylic acid (164b), and (+)-3-hydroxy-4-isopropyl-1-cyclo-hexanecarboxylic acid (165ab). On the other hand, (+)-menthone (149a') was converted to give (+)-3-oxo-4-isopropyl-1-cyclohexane carboxylic acid (164a') and (-)-3-oxo-4-isopropyl-1-cyclohexane carboxylic acid (164b'). Racemic isomenthone (149b and b') was converted to give racemic 1-hydroxy-1-methyl-4-isopropylcyclohexane-3-one (150), racemic piperitone (156), racemic 3-oxo-4-isopropyl-1-cyclohexene-1-carboxylic acid (162), 3-oxo-4-isopropyl-1-cyclohexane carboxylic acid (164b), 3-oxo-4-isopropyl-1-cyclohexane carbxylic acid (164a), and (+)-3-hydroxy-4-isopropyl-1-cyclohexane carboxylic acid (165ab) (Figure 14.131).

Soil plant pathogenic fungi, Rhizoctonia solani 189 converted (-)-menthone (149a) to 4ß -hydroxy-(-)-menthone (392, 29%) and 1 a, 4 ß-dihydroxy-(-)-menthone (393, 71%) (Nonoyama et al., 1999) (Figure 14.131). (-)-Menthone (149a) was transformed by Spodoptera litura to give 7-hydroxymenthone (151a), 7-hydroxyneomenthol (165c), and 7-hydroxy-9-carboxymenthone (394a) (Hagiwara et al., 2006) (Figure 14.132). (-)-Menthone (149a) gave 7-hydroxymenthone (151a) and (+)-neomenthol (137c) by human liver microsome (CYP2B6). Of 11 recombinant human P450 enzymes (express in Trichoplusia ni cells) tested, CYP2B6 catalyzed oxidation of (-)-menthone (149a) to 7-hydroxymenthone (151a) (Nakanishi and Miyazawa, 2004) (Figure 14.132).

14.3.4.2.4 Thujone

28a'

28a'

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