Cw-Carveol

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... 

FIGURE 19.87 Metabolic pathways of t) trans- (81a) and (+) cw-carveol (81b) by Streptomyces bottro-pensis SY-2-1. (Modi ed from Noma, Y. and Nishimura, H., Agric. Biol. Chem., 51, 1845, 1987 Nishimura, H. and Noma, Y, Biotechnology for Improved Foods and Flavors, G.R. Takeoka, et al., ACS Symp. Ser. 637, pp.173-187. American Chemical Society, Washington, DC, 1996.)... 

FIGURE 19.90 Enantio and diastereoselective biotransformation of trans (81a and a ) and cw-carveols (81b and b ) by Euglena gracilis Z and Chlorella pyrenoidosa lAM C 28. (Modi ed from Noma, Y. and Asakawa, Y., Phytochemistry, 31, 2009, 1992 Noma, Y. et al., Biotransformation of terpenoids and related compounds by Chlorella species. Proceedings of 41st TEAC, 1997, pp. 227-229.)... 

Nishimura, H., S. Hiramoto, and J. Mizutani, 1983a. Biological activity of bottrospicatol and related com pounds produced by microbial transformation of (-)-cw-carveol towards plants. Proceedings of the 27th TEAC, pp. 107-109. 

Noma, Y., H. Nishimura, and C. Tatsumi, 1980. Biotransformation of carveol by Actinomycetes. 1. Biotransformation of (-)-cw-carveol and (-)-rra -carveol by Streptomyces bottropensis, SY-2-1. Proceedings of the 24th TEAC, pp. 67-70. 

Newly isolated unidentified red yeast, Rhodotorula sp., converted (+)-limonene (68) mainly to (-H)-limonene-l,2-tra i-diol (71a), i+)-trans-curveo (81a), (-l-)-cw-carveol (81b), and (+)-carvone (93 ) together with (+)-limonene-l,2-ci5 -diol (71b) as minor product (Noma and Asakawa, 2007b) (Figure 14.36). 

On the other hand, in Streptomyces, A-5-1 and Nocardia, 1-3-11, which were isolated from soil, (-)-carvone (93 ) was reduced to give mainly -)-trans-car eol (81a ) and (-)-cw-carveol (81b ), respectively. On the other hand, (-)-trani-carveol (81a ) and (-)-cw-carveol (81b ) were dehydrogenated to give 93 by strain 1-3-11 and other microorganisms (Noma et al., 1986). The reaction between trans- and ds-carveols (81a and 81b ) and (-)-carvone (93 ) is reversible (Noma, 1980) (Figure 14.82). 

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