a When ethanol was used. b When glucose was used.

Group 4. 93'-(+)-Isodihydrocarvone (101b')-102c' and 102d'

Group 5. (+)-Carvone (93)-(-)-isodihydrocarvone (101b)-(-)-neoisodihydrocarveol (102d)

Group 6. 93-101b-102c

Group 7. 93-101b-102c and 102d

Group 8. 93-101b-101a

The result of the mode action of both the hydrogenation of carvone and the reduction for dihy-drocarvone by microorganism is as follows. In bacteria, only two strains were able to convert (-)-carvone (93') via (+)-dihydrocarvone (101a') to (-)-dihydrocarveol (102b') as the major product (Group 3, when ethanol was used as a carbon source, 12.5% of (-)-carvone (93') convertible microorganisms belonged to this group and when glucose was used, 8% belonged to this group) (Noma and Tatsumi 1973; Noma et al., 1975), whereas when (+)-carvone (93) was converted, one strain converted it to a mixture of (-)-isodihydrocarveol (102c) and (-)-neoisodihydrocarveol (102d) (Group 7, 6% and 4% of 93 convertible bacteria belonged to this group, when ethanol and glucose were used, respectively.) and four strains converted it via (-)-isodihydrocarvone (101b) to (-)-dihydrocarvone (101a) (Group 8, 6% and 15% of (+)-carvone (93') convertible bacteria belonged to this group, when ethanol and glucose were used, respectively.) (Noma et al., 1975). In yeasts, 43% of carvone convertible yeasts belong to group 1, 14% to group 2, and 33% to group 3 (of this group, three strains are close to group 1) and 12% to group 5, 4% to group 6, and 27% to group 7 (of this group, three strains are close to group 5 and one strain is close to group 6). In fungi, 51% of fungi metabolizing (-)-carvone (93') by way of group 1 and 3% via group 3, but there was no strain capable of metabolizing (-)-carvone (93') via group 2, whereas 20% of fungi metabolized (+)-carvone (93) via group 5 and 29% via group 7, but there was no strain capable of metabolizeing (+)-carvone (93) via group 6. In actinomycetes, (-)-carvone (93') was converted to dihydrocarveols via group 1 (49%), group 2 (0%), group 3 (9%), and group 4 (28%), whereas (+)-carvone (93) was converted to dihydrocarveols via group 5 (7%), group 6 (0%), group 7 (19%), and group 8 (0%).

Furthermore, (+)-neodihydrocarveol (102a') stereospecifically formed from (-)-carvone (93') by Aspergillus niger TBUYN-2 was further biotransformed to mosquito repellent (1R,2S,4R)-(+)-p-menthane-2,8-diol (50a'), (1R,2S,4R)-(+)-8-p-menthene-2,10-diol (107a'), and the mixture of (1R,2S,4R,8S/R)-(+)-p-menthane-2,8,9-triols (104aa' and 104ab'), while Absidia glauca ATCC 22752 gave 107a' stereoselectively from 102a' (Demirci et al., 2001) (Figure 14.106).

On the other hand, (-)-carvone (93') was biotransformed stereoselectively to (+)-neodihydrocar-veol (102a') via (+)-dihydrocarvone (101a') by a strain of Aspergillus niger (Noma and Nonomura 1974), Euglena gracilis Z. (Noma et al., 1993), and Chlorella miniata (Gondai et al., 1999). Furthermore, in Euglena gracilis Z., mosquito repellent (1R,2S,4R)-(+)-p-menthane-2,8-diol (50a') was obtained stereospecifically from (-)-carvone (93') via 101a' and 102a' (Figure 14.107).

As the microbial method for the formation of mosquito repellentl 50a' was established, the production of (+)-dihydrocarvone (101a') and (+)-neodihydrocarveol (102a') as the precursor of mosquito repellent 50a' was investigated by using 40 strains of bacteria belonging to Escherichia, Aerobacter, Serratia, Proteus, Alcaligenes, Bacillus, Agrobacterium, Micrococcus, Staphylococcus, Corynebacterium, Sarcina, Arthrobacter, Brevibacterium, Pseudomonas, and Xanthomonas spp., 68 strains of yeasts belonged to Schzosaccharomyces, Endomycopsis, Saccharomyces, Schwanniomyces, Debaryomyces, Pichia, Hansenula, Lipomyces, Torulopsis, Saccharomycodes, Cryptococcus, Kloeckera, Trigonopsis, Rhodotorula, Candida, and Trichosporon spp., 40 strains of fungi belonging to Mucor, Absidia, Penicillium, Rhizopus, Aspergillus, Monascus, Fusarium, Pullularia,Keratinomyces, Oospora,Neurospora, Ustilago,Sporotrium, Trichoderma, Gliocladium, and Phytophythora spp., and 48 strains of actinomycetes belonging to Streptomyces, Actinoplanes, Nocardia, Micromonospora, Microbispora, Micropolyspora, Amorphosporangium, Thermopolyspora, Planomonospora, and Streptosporangium spp.

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