Cytochrome P-450 dependent (+)-limonene-6-hydroxylation in fruits of caraway (Carum carvi)

Abstract Microsomal preparations from fruits of annual and biennial forms of caraway (Carum carvi L.) catalyze the C-6 hydroxylation of (+)-limonene to (+)-trans-carveol, the key intermediate in the biosynthesis of carvone. The enzyme activities from both caraway forms had similar properties (pH optimum, Km, cofactor requirements, etc). Both activities were dependent on NADPH and O2, and were inhibited by N-substituted imidazoles, metyrapone, cytochrome c and CO, and thus meet many of the established criteria for cytochrome P-450-dependent mixed function oxygenases.

[1]  R. Croteau,et al.  Induction and Characterization of a Cytochrome P-450-Dependent Camphor Hydroxylase in Tissue Cultures of Common Sage (Salvia officinalis) , 1993, Plant physiology.

[2]  R. Estabrook,et al.  Inhibition of rat liver microsomal cytochrome P-450 steroid hydroxylase reactions by imidazole antimycotic agents. , 1986, Biochemical pharmacology.

[3]  R. Croteau,et al.  Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves. , 1990, Archives of biochemistry and biophysics.

[4]  R. Croteau,et al.  Cytochrome P450-catalyzed hydroxylation of taxa-4(5),11(12)-diene to taxa-4(20),11(12)-dien-5alpha-ol: the first oxygenation step in taxol biosynthesis. , 1996, Chemistry & biology.

[5]  T. Meehan,et al.  Characterization of a cytochrome P-450 dependent monoterpene hydroxylase from the higher plant Vinca rosea. , 1976, Biochemistry.

[6]  T. Omura,et al.  THE CARBON MONOXIDE-BINDING PIGMENT OF LIVER MICROSOMES. II. SOLUBILIZATION, PURIFICATION, AND PROPERTIES. , 1964, The Journal of biological chemistry.

[7]  K. Higashi,et al.  5-epi-Aristolochene 3-hydroxylase from green pepper , 1995 .

[8]  M. Schuler.  Plant Cytochrome P450 Monooxygenases , 1996 .

[9]  J. Gershenzon,et al.  Biochemical and Histochemical Localization of Monoterpene Biosynthesis in the Glandular Trichomes of Spearmint (Mentha spicata). , 1989, Plant physiology.

[10]  Bouwmeester,et al.  Biosynthesis of the monoterpenes limonene and carvone in the fruit of caraway. I. Demonstration Of enzyme activities and their changes with development , 1998, Plant physiology.

[11]  R. Niedz,et al.  A Cytochrome P450 Mediated Naringenin 3′-Hydroxylase from Sweet Orange Cell Cultures , 1995 .

[12]  R. Croteau,et al.  Metabolism of monoterpenes: demonstration of the hydroxylation of (+)-sabinene to (+)-cis-sabinol by an enzyme preparation from sage (Salvia officinalis) leaves. , 1987, Archives of biochemistry and biophysics.