FIGURE 14.93 Biotransformation of (-)- and (+)-neodihydrocarveol (102a and a') by Euglena gracilis Z, Aspergillus niger TBUYN-2, and Absidia glauca. (Modified from Noma, Y. et al., 1985a. Annual Meeting of Agricultural and Biological Chemistry, Sapporo, p. 68; Noma, Y. et al., 1985b. Proc. 29th TEAC, pp. 235-237; Noma, Y. et al., 1993. Proc. 37th TEAC, pp. 23-25; Noma, Y., 2007. Aromatic Plants from Asia their Chemistry and Application in Food and Therapy, L. Jiarovetz, N.X. Dung, and V.K. Varshney, pp. 169-186. Dehradun: Har Krishan Bhalla & Sons; Noma, Y. and Y. Asakawa, 1995. Biotechnology in Agriculture and Forestry, Vol. 33. Medicinal and Aromatic Plants VIII, Y.P.S. Bajaj, ed., pp. 62-96. Berlin: Springer; Demirci, F. et al., 2004. Naturforsch., 59c: 389-392.)
Euglena gracilis Z. converted (-)- (102d) and (+)-neoisodihydrocarveol (102d') to give the corresponding 8-hydroxyneoisodihydrocarveols (50d and 50d'), respectively (Noma et al., 1993) (Figure 14.98).
Eight kinds of 8-hydroxydihydrocarveols (50a-d and 50a'-d'; 8-p-menthane-2,8-diols) were obtained from carvone (93 and 93'), dihydrocarvones (101a-b and 101a'-b'), and dihydrocarveols (102a-d, 102a'-d') by Euglena gracilis Z as shown in Figure 14.99 (Noma et al., 1993).
Aspergillus sp. Eg
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