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CYP73As


P450 Function Plant Species
CYP73A1 : cinnamate 4-hydroxylase (C4H) artichoke
CYP73A2 cinnamate 4-hydroxylase (C4H) mung bean
CYP73A3 cinnamate 4-hydroxylase (C4H) alfalfa
CYP73A4 cinnamate 4-hydroxylase (C4H) periwinkle
CYP73A5 cinnamate 4-hydroxylase (C4H) Arabidopsis
CYP73A9 cinnamate 4-hydroxylase (C4H) pea
CYP73A10 cinnamate 4-hydroxylase (C4H) parsley
CYP73A11 cinnamate 4-hydroxylase (C4H) soybean
CYP73A13 cinnamate 4-hydroxylase (C4H) quaking aspen
CYP73A14 cinnamate 4-hydroxylase (C4H) licorice
CYP73A15 cinnamate 4-hydroxylase (C4H) French bean
CYP73A16 cinnamate 4-hydroxylase (C4H) hybrid aspen
CYP73A19 cinnamate 4-hydroxylase (C4H) chickpea
CYP73A cinnamate 4-hydroxylase (C4H) poplar
CYP73A cinnamate 4-hydroxylase (C4H) tobacco
CYP73A cinnamate 4-hydroxylase (C4H) hornwort
CYP73A cinnamate 4-hydroxylase (C4H) Ammi majus
CYP73A cinnamate 4-hydroxylase (C4H) Ruta graveolens


CYP73A1:   cinnamate 4-hydroxylase (C4H), artichoke (Helianthus tuberosus).
1)  Batard Y, Schalk M, Pierrel MA, Zimmerlin A, Durst F, Werck-Reichhart D  (1997)  Regulation of the cinamate 4-hydroxylase (CYP73A1) in Jerusalem artichoke tubers in response to wounding and chemical treatments.  Plant Physiol 113: 951-959.  PubMed
2)  Schalk M, Batard Y, Seyer A, Nedelkina S, Durst F, Werck-Reichhart D  (1997)  Design of fluorescent substrates and potent inhibitors of CYP73As, P450s that catalyze 4-hydroxylation of cinnamic acid in higher plants.  Biochemistry 36: 15253-15261.  PubMed
3)  Schalk M, Cabello-Hurtado F, Pierrel M-A, Atanossova R, Saindrenan P, Werck-Reichhart D  (1998)  Piperonylic acid, a selective, mechanism-based inactivator of the trans-cinnamate 4-hydroxylase: a new tool to control the flux of metabolites in the phenylpropanoid pathway.  Plant Physiol 118: 209-218.  PubMed
4)  Schalk M, Nedelkina S, Schoch G, Batard Y, Werck-Reichhart D  (1999)  Role of unusual amino acid residues in the proximal and distal heme regions of a plant P450, CYP73A1.  Biochemistry 38: 6093-6103.  PubMed
5)  Schoch GA, Nikov GN, Alworth WL, Werck-Reichhart D  (2002)  Chemical inactivation of the cinnamate 4-hydroxylase allows for the accumulation of salicylic acid in elicited cells.  Plant Physiol 130: 1022-1031.  PubMed
6)  Schoch GA, Attias R, Le Ret M, Werck-Reichhart D  (2003)  Key substrate recognition residues in the active site of a plant cytochrome P450, CYP73A1. Homology guided site-directed mutagenesis.  Eur J Biochem 270: 3684-3695.  PubMed
7)  Schoch GA, Attias R, Belghazi M, Dansette PM, Werck-Reichhart D  (2003)  Engineering of a water-soluble plant cytochrome P450, CYP73A1, and NMR-based orientation of natural and alternate substrates in the active site.  Plant Physiol 133: 1198-1208.  PubMed

CYP73A2:   cinnamate 4-hydroxylase (C4H), mung bean (Phaseolus aureus).
Mizutani M, Ward ER, DiMaio J, Ryals JA, Ohta D, Sato R  (1993)  Molecular cloning and sequencing of a cDNA encoding mung bean cytochrome P450 (P450C4H) possessing cinnamate 4-hydroxylase activity.  Biochem Biophys Res Commun 190: 875-880.  PubMed

CYP73A3:   cinnamate 4-hydroxylase (C4H), alfalfa (Medicago sativa).
Fahrendorf T, Dixon RA  (1993)  Stress responses in alfalfa (Medicago sativa). XVIII: Molecular cloning of the elicitor-inducible cinnamic acid 4-hydroxylase cytochrome P450 from alfalfa.  Arch Biochem Biophys 305: 509-515.  PubMed

CYP73A4:   cinnamate 4-hydroxylase (C4H), Madagascar periwinkle (Catharanthus roseus).
Hotze M, Schroeder G, Schroeder J  (1995)  Cinnamate 4-hydroxylase from Catharanthus roseus, and a strategy for the functional expression of plant cytochrome P450 proteins as translational fusions with P450 reductase in Escherichia coli.  FEBS Lett 374: 345-350.  PubMed

CYP73A5:   cinnamate 4-hydroxylase (C4H), Arabidopsis thaliana.
1)  Mizutani M, Ohta D, Sato R  (1997)  Isolation of a cDNA and a genomic clone encoding cinnamate 4-hydroxylase from Arabidopsis and its expression manner in plants.  Plant Physiol 113: 755-763.  PubMed
2)  Bell-Lelong DA, Cusumano JC, Meyer K, Chapple C  (1997)  Cinnamate-4-hydroxylase expression in Arabidopsis. Regulation in response to development and the environment.  Plant Physiol 113: 729-738.  PubMed
3)  Humphreys JM, Chapple C  (2004)  Immunodetection and quantification of cytochromes P450 using epitope tagging: immunological, spectroscopic, and kinetic analysis of cinnamate 4-hydroxylase.  J Immunol Meth 292: 97-107.  PubMed

CYP73A9:   cinnamate 4-hydroxylase, pea (Pisum sativum).
1)  Frank MR, Deyneka JM, Schuler MA  (1996)  Cloning of wound-induced cytochrome P450 monooxygenases expressed in pea.  Plant Physiol 110: 1035-1046.  PubMed
2)  Whitbred JM, Schuler MA  (2000)  Molecular characterization of CYP73A9 and CYP82A1 P450 genes involved in plant defense in pea.  Plant Physiol 124: 47-58.  PubMed

CYP73A10:   cinnamate 4-hydroxylase (C4H), parsley (Petroselinum crispum).
1)  Logemann E, Parniske M, Hahlbrock K  (1995)  Modes of expression and common structural features of the complete phenylalanine ammonia-lyase gene family in parsley.  Proc Natl Acad Sci USA 92: 5905-5909.  PubMed
2)  Koopman E, Logemann E, Hahlbrock K  (1999)  Regulation and functional expression of cinnamate 4-hydroxylase from parsley.  Plant Physiol 119: 49-55.  PubMed

CYP73A11:   cinnamate 4-hydroxylase (C4H), soybean (Glycine max).
Schopfer CR, Ebel J  (1998)  Identification of elicitor-induced cytochrome P450s of soybean (Glycine max L.) using differential display of mRNA.  Mol Gen Genet 258: 315-322.  PubMed

CYP73A13:   cinnamate 4-hydroxylase (C4H), quaking aspen (Populus tremuloides).
Ge L, Chiang VL  (1996)  A full length cDNA encoding trans-cinnamate 4-hydroxylase from developing xylem of Populus tremuloides.  Plant Physiol 112: 861.  

CYP73A14:   cinnamate 4-hydroxylase (C4H), licorice (Glycyrrhiza echinata).
Akashi T, Aoki T, Takahashi T, Kameya N, Nakamura I, Ayabe S  (1997)  Cloning of cytochrome P450 cDNAs from cultured Glycyrrhiza echinata L. cells and their transcriptional activation by elicitor treatment.  Plant Science 126: 39-47.  

CYP73A15:   cinnamate 4-hydroxylase, French bean (Phaseolus vulgaris).
1)  Nedelkina S, Jupe SC, Blee KA, Schalk M, Werck-Reichhart D, Bolwell GP  (1999)  Novel characteristics and regulation of a divergent cinnamate 4-hydroxylase (CYP73A15) from French bean: engineering expression in yeast.  Plant Mol Biol 39: 1079-1090.  PubMed
2)  Blee K, Choi JW, O'Connell AP, Jupe SC, Schuch W, Lewis NG, Bolwell GP  (2001)  Antisense and sense expression of cDNA coding for CYP73A15, a class II cinnamate 4-hydroxylase, leads to a delayed and reduced production of lignin in tobacco.  Phytochemistry 57: 1159-1166.  PubMed

CYP73A16:   cinnamate 4-hydroxylase (C4H), hybrid aspen (Populus kitakamiensis).
Kawai S, Mori A, Shiokawa T, Kajita S, Katayama Y, Morohoshi N  (1996)  Isolation and analysis of cinnamic acid 4-hydroxylase homologous genes from a hybrid aspen, Populus kitakamiensis.  Biosci Biotechnol Biochem 60: 1586-1597.  PubMed

CYP73A19:   cinnamate 4-hydroxylase (C4H), chickpea (Cicer arietinum).
Overkamp S, Hein F, Barz W  (2000)  Cloning and characterization of eight cytochrome P450 cDNAs from chickpea (Cicer arietinum L.) cell suspension cultures.  Plant Science 155: 101-108.  PubMed

CYP73A:   cinnamate 4-hydroxylase (C4H), poplar (Populus trichocarpa x Populus deltoides).
1)  Ro DK, Mah N, Ellis BE, Douglas CJ  (2001)  Functional characterization and subcellular localization of poplar (Populus trichocarpa x Populus deltoides) cinnamate 4-hydroxylase.  Plant Physiol 126: 317-329.  PubMed
2) &nbs;Yamada N, Kataoka Y, Nagami T, Hong SS, Kawai S, Kuwano E  (2004)  5-Aryl-1,3,4-oxadiazole-2-thiols as a new series of trans-cinnamate 4-hydroxylase inhibitors.  J Pest Sci 29: 2005-208.  

CYP73A:   cinnamate 4-hydroxylase (C4H), tobacco (Nicotiana tabacum).
Schoch GA, Nikov GN, Alworth WL, Werck-Reichhart D  (2002)  Chemical inactivation of the cinnamate 4-hydroxylase allows for the accumulation of salicylic acid in elicited cells.  Plant Physiol 130: 1022-1031.  PubMed

CYP73A-not cloned yet:   cinnamate 4-hydroxylase (C4H), hornwort (Anthoceros agrestis).
Peterson M  (2003)  Cinnamic acid 4-hydroxylase from cell cultures of the hornwort Anthoceros agrestis.  Planta 217: 96-101.  PubMed

CYP73A:   cinnamate 4-hydroxylase (C4H), Ammi majus.
Hubner S, Hehmann M, Schreiner S, Martens S, Lukacin R, Matern U  (2003)  Functional expression of cinnamate 4-hydroxylase from Ammi majus L.  Phytochemistry 64: 445-452.  PubMed

CYP73A:   cinnamate 4-hydroxylase (C4H), Ruta graveolens.
Gravot A, Larbat R, Hehn A, Lievre K, Gontier E, Goergen JL, Bourgaud F  (2004)  Cinnamic acid 4-hydroxylase mechanism-based inactivation by psoralen derivatives: cloning and characterization of a C4H from a psoralen producing plant - Ruta graveolens - exhibiting low sensitivity to psoralen inactivation.  Archiv Biochem Biophys 422: 71-80.  PubMed


Comments? Questions?   email:  joan.krochko@nrc-cnrc.gc.ca   website:  P450s in Plants
Plant Biotechnology Institute, National Research Council, Saskatoon, Saskatchewan   CANADA   S7N0W9
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