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Plant Physiol. 1992 April; 98(4): 1290–1297. | PMCID: PMC1080347 |
Interactions of Avocado (Persea americana) Cytochrome P-450 with Monoterpenoids David L. Hallahan, Jonathan H. A. Nugent, Beverly J. Hallahan, Glenn W. Dawson, Diane W. Smiley, Jevon M. West, and Roger M. Wallsgrove Biochemistry and Physiology Department, AFRC Institute of Arable Crops Research, Rothamsted Experimental Station, Harpenden, Herts. AL5 2JQ, United Kingdom Insecticides and Fungicides Department, AFRC Institute of Arable Crops Research, Rothamsted Experimental Station, Harpenden, Herts. AL5 2JQ, United Kingdom Department of Biology, University College London, Gower Street, London WC1E 6BT, United Kingdom Abstract The microsomal fraction of avocado (Persea americana) mesocarp is a rich source of cytochrome P-450 active in the demethylation of xenobiotics. Cytochrome P-450 from this tissue has been purified and well characterized at the molecular level (DP O'Keefe, KJ Leto [1989] Plant Physiol 89: 1141-1149; KR Bozak, H Yu, R Sirevag, RE Christoffersen [1990] Proc Natl Acad Sci USA 87: 3904-3908). Despite this extensive characterization, the role of the enzyme in vivo was not established. Optical and electron paramagnetic resonance binding studies described here suggest that the monoterpenoids, nerol and geraniol, are substrates of avocado cytochrome P-450 (spectral dissociation constant of 7.2 and 35 micromolar, respectively). Avocado microsomes have been shown to catalyze the hydroxylation of these monoterpenoids, and both nerol and geraniol have been shown to inhibit the activity of avocado cytochrome P-450 toward the artificial substrate 7-ethoxycoumarin, with nerol a competitive inhibitor of this activity. Full text Full text is available as a scanned copy of the original print version. Get a printable copy (PDF file) of the complete article (1.2M), or click on a page image below to browse page by page. Links to PubMed are also available for Selected References. These references are in PubMed. This may not be the complete list of references from this article. - Bozak KR, Yu H, Sirevåg R, Christoffersen RE. Sequence analysis of ripening-related cytochrome P-450 cDNAs from avocado fruit. Proc Natl Acad Sci U S A. 1990 May;87(10):3904–3908. [PMC free article] [PubMed]
- Cinti DL, Sligar SG, Gibson GG, Schenkman JB. Temperature-dependent spin equilibrium of microsomal and solubilized cytochrome P-450 from rat liver. Biochemistry. 1979 Jan 9;18(1):36–42. [PubMed]
- Cottrell S, Hartman GC, Lewis DF, Parke DV. Studies on the cytochrome P-450 of avocado (Persea [corrected] americana) mesocarp microsomal fraction. Xenobiotica. 1990 Jul;20(7):711–726. [PubMed]
- Dohn DR, Krieger RI. N-demethylation of p-chloro-N-methylaniline catalyzed by subcellular fractions from the avocado pear (Persea americana). Arch Biochem Biophys. 1984 Jun;231(2):416–423. [PubMed]
- Hallahan DL, Heasman AP, Grossel MC, Quigley R, Hedden P, Bowyer JR. Synthesis and biological activity of an azido derivative of paclobutrazol, an inhibitor of gibberellin biosynthesis. Plant Physiol. 1988 Dec;88(4):1425–1429. [PMC free article] [PubMed]
- Higashi K, Ikeuchi K, Karasaki Y, Obara M. Isolation of immunochemically distinct form of cytochrome P-450 from microsomes of tulip bulbs. Biochem Biophys Res Commun. 1983 Aug 30;115(1):46–52. [PubMed]
- Jefcoate CR. Measurement of substrate and inhibitor binding to microsomal cytochrome P-450 by optical-difference spectroscopy. Methods Enzymol. 1978;52:258–279. [PubMed]
- Karp F, Mihaliak CA, Harris JL, Croteau R. Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves. Arch Biochem Biophys. 1990 Jan;276(1):219–226. [PubMed]
- Laemmli UK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature. 1970 Aug 15;227(5259):680–685. [PubMed]
- Madyastha KM, Meehan TD, Coscia CJ. Characterization of a cytochrome P-450 dependent monoterpene hydroxylase from the higher plant Vinca rosea. Biochemistry. 1976 Mar 9;15(5):1097–1102. [PubMed]
- Markwell MA, Haas SM, Bieber LL, Tolbert NE. A modification of the Lowry procedure to simplify protein determination in membrane and lipoprotein samples. Anal Biochem. 1978 Jun 15;87(1):206–210. [PubMed]
- Meehan TD, Coscia CJ. Hydroxylation of geraniol and nerol by a monooxygenase from Vinca rosea. Biochem Biophys Res Commun. 1973 Aug 21;53(4):1043–1048. [PubMed]
- O'keefe DP, Leto KJ. Cytochrome P-450 from the Mesocarp of Avocado (Persea americana). Plant Physiol. 1989 Apr;89(4):1141–1149. [PMC free article] [PubMed]
- Orme-Johnson NR, Orme-Johnson WH. Detection and quantitation of free cytochrome P-450 and cytochrome P-450 complexes by EPR spectroscopy. Methods Enzymol. 1978;52:252–257. [PubMed]
- Peisach J, Appleby CA, Blumberg WE. Electron paramagnetic resonance and temperature dependent spin state studies of ferric cytochrome P-450 from Rhizobium japonicum. Arch Biochem Biophys. 1972 Jun;150(2):725–732. [PubMed]
- Rich PR, Cammack R, Bendall DS. Electron paramagnetic resonance studies of cytochrome P-450 in plant microsomes. Eur J Biochem. 1975 Nov 1;59(1):281–286. [PubMed]
- Salaün JP, Benveniste I, Reichhart D, Durst F. A microsomal (cytochrome P-450)-linked lauric-acid-monooxygenase from aged Jerusalem-artichoke-tuber tissues. Eur J Biochem. 1978 Sep 15;90(1):155–159. [PubMed]
- Sligar SG. Coupling of spin, substrate, and redox equilibria in cytochrome P450. Biochemistry. 1976 Nov 30;15(24):5399–5406. [PubMed]
- Stewart CB, Schuler MA. Antigenic Crossreactivity between Bacterial and Plant Cytochrome P-450 Monoxygenases. Plant Physiol. 1989 Jun;90(2):534–541. [PMC free article] [PubMed]
- Towbin H, Staehelin T, Gordon J. Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: procedure and some applications. Proc Natl Acad Sci U S A. 1979 Sep;76(9):4350–4354. [PMC free article] [PubMed]
- Usui E, Noshiro M, Ohyama Y, Okuda K. Unique property of liver mitochondrial P450 to catalyze the two physiologically important reactions involved in both cholesterol catabolism and vitamin D activation. FEBS Lett. 1990 Nov 12;274(1-2):175–177. [PubMed]
- Werck-Reichhart D, Gabriac B, Teutsch H, Durst F. Two cytochrome P-450 isoforms catalysing O-de-ethylation of ethoxycoumarin and ethoxyresorufin in higher plants. Biochem J. 1990 Sep 15;270(3):729–735. [PMC free article] [PubMed]
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