Streptomyces carveol

Effects of (-)-c/s- (81b ) and (-)-frans-Carveol (81a ) Conversion Products by Streptomyces bottropensis SY-2-1 on the Germination of Lettuce Seeds... 

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.)... 

Streptomyces A-5-1 isolated from soil converted (-)-carvone (93 ) to 101a -102d and -)-trans-carveo (81a ). whereasNocardia, 1-3-11 converted (-)-carvone (93 ) to (-)-di-carveol (81b )... 

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. 

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). 

FIGURE 14.83 The Metabolic pathways of ci -carveol (81b ) by Pseudomonas ovalis, strain 6-1 (Modified from Noma, Y, 1977. Nippon Nogeikagaku Kaishi, 51 463-470) and Streptomyces bottropensis SY-2-1 and other microorganisms (Modified from Noma, Y. et al., 1982. Agric. Biol. Chem., 46 2871-2872 Nishimura, H. et al, 1983a. Proc. 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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