Carvone actinomycetes

The distribution of carvone convertible microorganisms is summarized in Table 19.5. When ethanol was used as a carbon source, 40% of bacteria converted (+)- (93) and (-)-carvone (93 ). On the other hand, when glucose was used, 65% of bacteria converted carvone. In the case of yeasts, 75% converted (+)- (93) and (-)-carvone (93 ). Of fungi, 90% and 85% of fungi converted 93 and 93, respectively. In actinomycetes, 56% and 90% converted 93 and 93, respectively. 

Many microorganisms except for some strains of actinomycetes were capable of hydrogenating the C = C double bond at C-1, 2 position of (+)- (93) and (-)-carvone (93 ) to give mainly (-)-isodihydrocarvone (101b) and (-r)-dihydrocarvone (101a ), respectively (Noma and Tatsumi, 1973 Noma et al., 1974b Noma and Nonomura, 1974 Noma, 1976, 1977) (Figure 19.105) (Tables 19.6 and 19.7). 

Furthermore, it was found that (-)-carvone (93 ) was converted via (+)-isodihydrocarvone (101b ) to (-+-)-isodihydrocarveol (102c ) and ( +)-neoisodihydrocarveol (102d ) by some strains of actinomycetes (Noma, 1979a,b). (-)-Isodihydrocarvone (101b) was epimerized to... 

Carvone (93 ) was metabolized by actinomycetes to give -f-trans- (81a ) and -)-cis-car-veol (81b ) and (-t)-dihydrocarvone (101a ) as reduced metabolites. Compound 81b was further metabolized to (-t-)-bottrospicatol (92a ). Furthermore, 93 was hydroxylated at C-5 position and C-8, 9 position to give 5p-hydroxy-(-)-carvone (98a ) and (-)-carvone-8,9-epoxide (96 ), respectively. Compound 98a was further metabolized to Sp hydroxyneodihydrocarveol (lOOaa ) via Sp hydroxydihydrocarvone (99a ) (Noma, 1979a,b, 1980) (Figure 19.111). 

The investigation of (-)-carvone (93 ) and (-r)-carvone (93) conversion pattern was carried out by using rare actinomycetes. The conversion pattern was class ed as follows (Figure 19.113) ... 

On the other hand, in the case of (+)-carvone (93) conversion, 44% of rare actinomycetes were capable of converting (+)-carvone (93) to give (+)-carvone-8,9-epoxide (96) via pathway 4 and (-)-5a-hydroxycarvone (98a), (-)-5p-hydroxycarvone (98b), and (-)-5a-hydroxyneodihydrocarveol (lOOaa) via pathway 3 (Noma and Sakai, 1984). 

Noma, Y., 1979b. On the pattern of reaction mechanism of (+)-carvone conversion by actinomycetes. Biochemical reduction of terpenes, part X, Ann. Res, Stud, Osaka Joshigakuen Junior College, 23 27-31. 

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