Carvone metabolic pathways

Monoterpenols were esterified by lipases from various micro-organisms (especially Aspergillus spp.),931 and ( )-carvyl acetates were hydrolysed by other species to give chiral carveols together with (unreacted) acetates of the enantiomer.932 The metabolic pathways for the conversions of (—)-carvone into (—)-... 

FIGURE 9.6 Metabolic pathway of (i )-(-)-carvone in healthy subjects. (Adapted from Jager, W. et al.,... 

FIGURE 9.7 Proposed metabolic pathway of (R) (-)- and (5)-(+)-carvone in healthy volunteers. (Adapted from Engel, W., ]. Agric. Food Chem., 49. 4069. 2001.)... 

Consequently, the metabolic pathways of carvone by microorganisms were summarized as the following eight groups (Figure 19.105) ... 

FIGURE 19.106 Metabolic pathways of (-)-carvone (93 ) by Aspergillus niger TBUYN-2 and Absidia glauca ATCC 22752. (Modi ed from Demirci, F. et al.. The biotransformation of thymol methyl ether by dif ferent fungi. Book of Abstracts of the XII Biotechnology Congr., p. 47, 2001.)... 

FIGURE 19.108 Metabolic pathways of (+)-carvone (93) by Pseudomonas ovalis strain 6-1 and other many microorganisms. (Modi ed from Noma. Y. et al., Agric. Biol. Chem., 38, 735,1974b.)... 

FIGURE 19.200 Metabolic pathways of limonene (68), perillyl alcohol (74), carvone (93), isopiperitenone (111), and piperitenone (112) by microorganisms. 

Noma, Y. and Y. T akawa, 2008. New metabolic pathways of (+)-carvone by Citrus pathogenic Aspergillus niger Tiegh CBAYN and A. niger TBUYN-2, Proceedings of the 52nd TEAC, pp. 206-208. 

FIGURE 8.4 Metabolic pathway of (i )-(-)-carvone in healthy subjects. (Adapted from Jager, W. et al., 2000. J. Pharm. Pharmacol., 52 191-197 Jahrmann, R., 2007. Metabolismus von Monterpenen und Sesquiterpenen in Mensch und Saugetier Bedeutung fiir die pharmazeutische Praxis. MPharm. diploma thesis, University of Vienna, Austria.). 

Streptomyces bottropensis SY-2-1 has also different metabolic pathways for (+)-tra 5-carveol (81a) and (-I-) -di-carveol (81b) (Noma and Iwami, 1994). Namely, Streptomyces bottropensis SY-2-1 converted (+)-trans-caiveo (81a) to (-i-)-carvone (93), (-f-)-carvone-8,9-epoxide (96), and (-i-)-5a-hydroxycarvone (98a) (Noma and Nishimura, 1982, 1984) (Figure 14.87). On the other hand, Streptomyces bottropensis SY-2-1 converted (+)-c -carveol (81b) to give (-)-isobottrospicatol (92b) and (+)-5-hydroxy-c -carveol (94b) as the main products and (-)-bottrospicatol (92a) as the minor product as shown in Figure 14.88 (Noma et al., 1980, Noma and Nishimura, 1987 Nishimura and Noma, 1996). 

FIGURE 14.113 Metabolic pathways of (+)- (93) and (-)-carvone (93 ) and dihydrocarveols (102a-d and 102a -d ) by Streptomyces bottropensis, SY-2-1 and Streptomyces ikutamanesh, Ya-2-1. (Modified from Noma, Y, 1984. Kagaku to Seibutsu, 22 742-746.)... 

In the metabolism of cw-carveol by microorganisms, there are four pathways (pathways 1-4) as shown in Figure 19.86. At rst, cA-carveol (81) is metabolized to carvone (93) by C2 dehydrogenation (Noma, 1977, 1980) (pathway 1). Second, ciY-carveol (81b) is metabolized via epoxide as intermediate to bottrospicatol (92) by rearrangement at C2 and C8 (Noma et al., 1982 Nishimura et al., 1983a,b Noma and Nishimura, 1987) (pathway 2). Third, cA-carveol (81b) is hydroxylated at C5 position to give S-hydroxy-ds-carveol (94) (Noma and Nishimura, 1984) (pathway 3). Finally, cw-carveol... 

---