Oh

125b

125b'

125b'

125b'-Mal

FIGURE 14.43 Formation of optical pure (+)- and (-)-2a-hydroxy-1,8-cineole (125b and b') from the biotransformation of 1,8-cineole (122) and (+)-limonene (68) by Citrus pathogenic fungi, Penicillium digitatum (Pers.; Fr.) Sacc. KCPYN and Aspergillus niger TBUYN-2. (Modified from Nishimura, H. et al., 1982. Agric. Biol. Chem., 46: 2601-2604; Miyazawa, M. et al., 1995b. Proc. 39th TEAC, pp. 352-353; Noma, Y. and Y. Asakawa, 2007b. Proc. 51st TEAC, pp. 299-301.)

When monoterpenes, such as limonene (68), a-pinene (4), and 3-carene (336), were administered to the cultured cells of Nicotiana tabacum, they were converted to the corresponding epoxides enantio- and stereoselectively. The enzyme (p38) concerning with the epoxidation reaction was purified from the cultured cells by cation exchanged chromatography. The enzyme had not only epoxida-tion activity but also peroxidase activity. Amino acid sequence of p38 showed 89% homology in their 9 amino acid overlap with horseradish peroxidase (Yawata et al., 1998) (Figure 14.44). It was found that limonene and carene were converted to the corresponding epoxides in the presence of hydrogen

H202

H202

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