9COOH 9 445
FIGURE 14.166 Metabolic pathways of (+)-3-carene (439) by rabbit (Modified from Ishida, T. et al., 1981b. J. Pharm. Sci, 70: 406-415). 3-(+)-Carene (439) was converted by Aspergillus niger NC 1M612 to give either hydroxylated compounds of 3-carene-2-one or 3-carene-5-one, which was not fully identified. (Modified from Noma, Y. et al., 2002. Book of Abstracts of the 33rd ISEO, p. 142) (Figure 14.167).
(+)-3-Carene (439) was biotransformed by rabbits to give m-mentha-4,6-dien-8-ol (440) (71.6%) as the main metabolite together with its aromatized m-cymen-8-ol (441). The position of C-5 in the substrate is thought to be more easily hydroxylated than C-2 by enzymatic systems in the rabbit liver. In addition to ring opening compound, 3-carene-9-ol (442), 3-carene-9-carboxylic acid (443), 3-carene-9,10-dicarboxilic acid (445), chamic acid, and 3-caren-10-ol-9-carboxylic acid (444) were formed. The formation of such compounds is explained by stereoselective hydroxylation and carboxylation of gem-dimethyl group (Ishida et al., 1981b) (Figure 14.166). In case of (-)-cis-carane (446), two C-9 and C-10 methyl groups were oxidized to give dicarboxylic acid (447) (Ishida et al., 1981b) (Figure 14.166).
3-(+)-Carene (439) was converted by Aspergillus niger NC 1M612 to give either hydroxylated compounds of 3-carene-2-one or 3-carene-5-one, which was not fully identified (Noma et al., 2002) (Figure 14.167).
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