Carvone Aspergillus

Epoxide is an important intermediate for various bioactive compounds, so the demand for the chiral epoxide is increasing. Epoxide hydrolase can hydrolyze epoxide enantioselectively (Figure 20).21 For example, Aspergillus niger was used for the hydrolysis of carvone epoxide (Figure 20(a)).2 11 In the reaction of styrene oxide, the... 

Both naturally occurring enantiomers of carvone were selectively reduced by B. sulfurescens (Scheme 71). (-)-Carvone was reduced to (-h)-dihydrocarvone (trans) and further to (-H)-neodihydrocarveol, whereas (-i-)-carvone was reduced to (-)-isodihydrocarvone (cis), which was then converted to (-)-neo-isodihydrocarveol. Similar reductions with identical stereoselectivities were observed earlier with Pseudomonas ovalis (strain 6-1) and with a strain of Aspergillus niger. ... 

Monoterpenols were esterified by lipases from various micro-organisms (especially Aspergillus spp.),931 and ( )-carvyl acetates were hydrolysed by other species to give chiral carveols together with (unreacted) acetates of the enantiomer.932 The metabolic pathways for the conversions of (—)-carvone into (—)-... 

FIGURE 19.106 Metabolic pathways of (-)-carvone (93 ) by Aspergillus niger TBUYN-2 and Absidia glauca ATCC 22752. (Modi ed from Demirci, F. et al.. The biotransformation of thymol methyl ether by dif ferent fungi. Book of Abstracts of the XII Biotechnology Congr., p. 47, 2001.)... 

Noma, Y. and Y. T akawa, 2008. New metabolic pathways of (+)-carvone by Citrus pathogenic Aspergillus niger Tiegh CBAYN and A. niger TBUYN-2, Proceedings of the 52nd TEAC, pp. 206-208. 

Noma, Y., T. Higata, T. Hirata, Y. Tanaka, T. Hashimoto, and Y. Asakawa, 1995. Biotransformation of [6- H]-(-) -carvone hy Aspergillus niger, Euglena gracilis Z and Dunaliella tertiolecta. Proceedings of the 39th TEAC. pp. 367-368. 

Noma, Y. and S. Nonomura, 1974. Conversion of (-)-carvone and (+)-carvone by a strain of Aspergillus niger. Aerie. Biol. Chem.. 38 741-744. 

FIGURE 14.109 Possible main metabolic pathways of (-)-carvone (93 ) and (+)-carvone (93) hy Aspergillus niger TBUYN-2. (Modified from Noma, Y. et al., 1985a. Annual Meeting of Agricultural and Biological Chemistry, Sapporo, p. 68.)... 

Noma, Y, M. Toyota, and Y. Asakawa, 1985b. Biotransformation of carvone. 6. Biotransformation of (—)-car-vone and (-l-)-carvone by a strain of Aspergillus niger. Proc. 29th TEAC, pp. 235-237. 

Anethole, anisaldehyde, and myristicin (in aniseed), along with z/-carvone (present in P. anisum plant), have shown mild insecticidal properties. In houseflies, the major (56% by weight) active insecticide in the oil from anise tops was shown to be frans-anethole. Anisaldehyde and anethole increased the toxicity to houseflies when applied at the same as various common insecticides. Anethole also inhibits growth of mycotoxin-producing Aspergillus species in culture. ... 

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