Carveol bottrospicatol

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... 

Group 2 Carvone (93), carveols (89), bottrospicatols (92), 5-hydroxy-cfi-carveols (12)... 

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. 

Effects of (-)-di- (81b ) and (-)-tra 5 -carveol (81a ) conversion products by Streptomyces bottropensis SY-2-1 on the germination of lettuce seeds was examined and the result is shown in Table 14.3. ( f)-Bottrospicatol (92 ) and (-)-carvone-8,9-epoxide (96 ) showed strong inhibitory activity for the germination of lettuce seeds. 

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). 

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