Comparison of Cytochrome P450 Genes from Six Plant Genomes
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Nelson DR (2006) Cytochrome P450 nomenclature 2004. In: Phillips IR, Shephard EA (eds) Methods in Molecular Biology Vol 320, Cytochrome P450 Protocols, 2nd edn. Humana Press Inc., Totowa, NJ, pp 1–10
Goremykin VV, Holland B, Hirsch-Ernst KI, Hellwig FH (2005) Analysis of Acorus calamus chloroplast genome and its phylogenetic implications. Mol Biol Evol 22:1813–1822. doi: 10.1093/molbev/msi173
Cahoon EB, Ripp KG, Hall SE, McGonigle B (2002) Transgenic production of epoxy fatty acids by expression of a cytochrome P450 enzyme from Euphorbia lagascae seed. Plant Physiol 128:615–624. doi: 10.1104/pp.010768
Nelson DR, Schuler MA, Paquette SM, Werck-Reichhart D, Bak S (2004a) Comparative genomics of Oryza sativa and Arabidopsis thaliana. Analysis of 727 Cytochrome P450 genes and pseudogenes from a monocot and a dicot. Plant Physiol 135:756–772. doi: 10.1104/pp.104.039826
Jaillon O et al (2007) French-Italian Public Consortium for Grapevine Genome Characterization. The grapevine genome sequence suggests ancestral hexaploidization in major angiosperm phyla. Nature 449:463–467. doi: 10.1038/nature06148
Velasco R et al (2007) A high quality draft consensus sequence of the genome of a heterozygous grapevine variety. PLoS One 2(12):e1326. doi: 10.1371/journal.pone.0001326
Kim J, DellaPenna D (2006) Defining the primary route for lutein synthesis in plants: the role of Arabidopsis carotenoid beta-ring hydroxylase CYP97A3. Proc Natl Acad Sci USA 103:3474–3479. doi: 10.1073/pnas.0511207103
Tian L, Musetti V, Kim J, Magallanes-Lundback M, DellaPenna D (2004) The Arabidopsis LUT1 locus encodes a member of the cytochrome p450 family that is required for carotenoid epsilon-ring hydroxylation activity. Proc Natl Acad Sci USA 101:402–407. doi: 10.1073/pnas.2237237100
Kushiro M, Nakano T, Sato K, Yamagishi K, Asami T, Nakano A, Takatsuto S, Fujioka S, Ebizuka Y, Yoshida S (2001) Obtusifoliol 14alpha-demethylase (CYP51) antisense Arabidopsis shows slow growth and long life. Biochem Biophys Res Commun 285:98–104. doi: 10.1006/bbrc.2001.5122
Kim HB, Schaller H, Goh CH, Kwon M, Choe S, An CS, Durst F, Feldmann KA, Feyereisen R (2005) Arabidopsis cyp51 mutant shows postembryonic seedling lethality associated with lack of membrane integrity. Plant Physiol 138:2033–2047. doi: 10.1104/pp.105.061598
Field B, Osbourn AE (2008) Metabolic diversification—independent assembly of operon-like gene clusters in different plants. Science 320:543–547. doi: 10.1126/science.1154990
Morikawa T, Mizutani M, Aoki N, Watanabe B, Saga H, Saito S, Oikawa A, Suzuki H, Sakurai N, Shibata D, Wadano A, Sakata K, Ohta D (2006) Cytochrome P450 CYP710A encodes the sterol C-22 desaturase in Arabidopsis and tomato. Plant Cell 18:1008–1022. doi: 10.1105/tpc.105.036012
Lee DS, Nioche P, Hamberg M, Raman CS (2008) Modes of heme binding and substrate access for cytochrome P450 CYP74A revealed by crystal structures of allene oxide synthase. Nature 455:363–368. doi: 10.1038/nature07307
Li L, Chang Z, Pan Z, Fu ZQ, Wang X (2008) Structural insights into the evolutionary paths of oxylipin biosynthetic enzymes. Proc Natl Acad Sci USA 105:13883–13888. doi: 10.1073/pnas.0804099105
Bate NJ, Sivasankar S, Moxon C, Riley JM, Thompson JE, Rothstein SJ (1998) Molecular characterization of an Arabidopsis gene encoding hydroperoxide lyase, a cytochrome P-450 that is wound inducible. Plant Physiol 117:1393–1400. doi: 10.1104/pp.117.4.1393
Noordermeer MA, Van Dijken AJ, Smeekens SC, Veldink GA, Vliegenthart JF (2000) Characterization of three cloned and expressed 13-hydroperoxide lyase isoenzymes from alfalfa with unusual N-terminal sequences and different enzyme kinetics. Eur J Biochem 267:2473–2482. doi: 10.1046/j.1432-1327.2000.01283.x
Kuroda H, Oshima T, Kaneda H, Takashio M (2005) Identification and functional analyses of two cDNAs that encode fatty acid 9-/13-hydroperoxide lyase (CYP74C) in rice. Biosci Biotechnol Biochem 69:1545–1554. doi: 10.1271/bbb.69.1545
Chehab EW, Raman G, Walley JW, Perea JV, Banu G, Theg S, Dehesh K (2006) Rice HYDROPEROXIDE LYASES with unique expression patterns generate distinct aldehyde signatures in Arabidopsis. Plant Physiol 141:121–134. doi: 10.1104/pp.106.078592
Stumpe M, Bode J, Göbel C, Wichard T, Schaaf A, Frank W, Frank M, Reski R, Pohnert G, Feussner I (2006) Biosynthesis of C9-aldehydes in the moss Physcomitrella patens. Biochim Biophys Acta 1761:301–312
US patent 6444874: http://www.freepatentsonline.com/6444874.html
Koeduka T, Stumpe M, Matsui K, Kajiwara T, Feussner I (2003) Kinetics of barley FA hydroperoxide lyase are modulated by salts and detergents. Lipids 38:1167–1172. doi: 10.1007/s11745-003-1175-9
Grechkin AN (2002) Hydroperoxide lyase and divinyl ether synthase. Prostaglandins Other Lipid Mediat 68–69:457–470. doi: 10.1016/S0090-6980(02)00048-5
Benveniste I, Tijet N, Adas F, Philipps G, Salaün JP, Durst F (1998) CYP86A1 from Arabidopsis thaliana encodes a cytochrome P450-dependent fatty acid omega-hydroxylase. Biochem Biophys Res Commun 243:688–693. doi: 10.1006/bbrc.1998.8156
Wellesen K, Durst F, Pinot F, Benveniste I, Nettesheim K, Wisman E, Steiner-Lange S, Saedler H, Yephremov A (2001) Functional analysis of the LACERATA gene of Arabidopsis provides evidence for different roles of fatty acid omega -hydroxylation in development. Proc Natl Acad Sci USA 98:9694–9699. doi: 10.1073/pnas.171285998
Xiao F, Goodwin SM, Xiao Y, Sun Z, Baker D, Tang X, Jenks MA, Zhou JM (2004) Arabidopsis CYP86A2 represses Pseudomonas syringae type III genes and is required for cuticle development. EMBO J 23:2903–2913. doi: 10.1038/sj.emboj.7600290
Duan H, Schuler MA (2005) Differential expression and evolution of the Arabidopsis CYP86A subfamily. Plant Physiol 137:1067–1081. doi: 10.1104/pp.104.055715
Rupasinghe SG, Duan H, Schuler MA (2007) Molecular definitions of fatty acid hydroxylases in Arabidopsis thaliana. Proteins 68:279–293. doi: 10.1002/prot.21335
Greer S, Wen M, Bird D, Wu X, Samuels L, Kunst L, Jetter R (2007) The cytochrome P450 enzyme CYP96A15 is the midchain alkane hydroxylase responsible for formation of secondary alcohols and ketones in stem cuticular wax of Arabidopsis. Plant Physiol 145:653–667. doi: 10.1104/pp.107.107300
Li Y, Beisson F, Koo AJ, Molina I, Pollard M, Ohlrogge J (2007) Identification of acyltransferases required for cutin biosynthesis and production of cutin with suberin-like monomers. Proc Natl Acad Sci USA 104:18339–18344. doi: 10.1073/pnas.0706984104
Höfer R, Briesen I, Beck M, Pinot F, Schreiber L, Franke R (2008) The Arabidopsis cytochrome P450 CYP86A1 encodes a fatty acid omega-hydroxylase involved in suberin monomer biosynthesis. J Exp Bot 59:2347–2360. doi: 10.1093/jxb/ern101
Olszewski N, Sun TP, Gubler F (2002) Gibberellin signaling: biosynthesis, catabolism, and response pathways. Plant Cell 14(Suppl):S61–S80
Yamaguchi S (2008) Gibberellin metabolism and its regulation. Annu Rev Plant Biol 59:225–251. doi: 10.1146/annurev.arplant.59.032607.092804
Morant M, Jørgensen K, Schaller H, Pinot F, Møller BL, Werck-Reichhart D, Bak S (2007) CYP703 is an ancient cytochrome P450 in land plants catalyzing in-chain hydroxylation of lauric acid to provide building blocks for sporopollenin synthesis in pollen. Plant Cell 19:1473–1487. doi: 10.1105/tpc.106.045948
Anastasiou E, Kenz S, Gerstung M, MacLean D, Timmer J, Fleck C, Lenhard M (2007) Control of plant organ size by KLUH/CYP78A5-dependent intercellular signaling. Dev Cell 13:843–856. doi: 10.1016/j.devcel.2007.10.001
Imaishi H, Matsuo S, Swai E, Ohkawa H (2000) CYP78A1 preferentially expressed in developing inflorescences of Zea mays encoded a cytochrome P450-dependent lauric acid 12-monooxygenase. Biosci Biotechnol Biochem 64:1696–1701. doi: 10.1271/bbb.64.1696
Miyoshi K, Ahn BO, Kawakatsu T, Ito Y, Itoh J, Nagato Y, Kurata N (2004) PLASTOCHRON1, a timekeeper of leaf initiation in rice, encodes cytochrome P450. Proc Natl Acad Sci USA 101:875–880. doi: 10.1073/pnas.2636936100
Wang JW, Schwab R, Czech B, Mica E, Weigel D (2008) Dual Effects of miR156-Targeted SPL Genes and CYP78A5/KLUH on Plastochron Length and Organ Size in Arabidopsis thaliana. Plant Cell 20:1231–1243. doi: 10.1105/tpc.108.058180
Jennewein S, Park H, DeJong JM, Long RM, Bollon AP, Croteau RB (2005) Coexpression in yeast of Taxus cytochrome P450 reductase with cytochrome P450 oxygenases involved in Taxol biosynthesis. Biotechnol Bioeng 89:588–598. doi: 10.1002/bit.20390
Rontein D, Onillon S, Herbette G, Lesot A, Werck-Reichhart D, Sallaud C, Tissier A (2008) CYP725A4 from yew catalyzes complex structural rearrangement of taxa-4(5),11(12)-diene into the cyclic ether 5(12)-oxa-3(11)-cyclotaxane. J Biol Chem 283:6067–6075. doi: 10.1074/jbc.M708950200
Ro DK, Arimura G, Lau SY, Piers E, Bohlmann J (2005) Loblolly pine abietadienol/abietadienal oxidase PtAO (CYP720B1) is a multifunctional, multisubstrate cytochrome P450 monooxygenase. Proc Natl Acad Sci USA 102:8060–8065. doi: 10.1073/pnas.0500825102
JGI Why sequence a liverwort? http://www.jgi.doe.gov/sequencing/why/99191.html
Ohnishi T, Watanabe B, Sakata K, Mizutani M (2006a) CYP724B2 and CYP90B3 function in the early C-22 hydroxylation steps of brassinosteroid biosynthetic pathway in tomato. Biosci Biotechnol Biochem 70:2071–2080. doi: 10.1271/bbb.60034
Talon M, Koornneef M, Zeevaart JA (1990) Endogenous gibberellins in Arabidopsis thaliana and possible steps blocked in the biosynthetic pathways of the semidwarf ga4 and ga5 mutants. Proc Natl Acad Sci USA 87:7983–7987. doi: 10.1073/pnas.87.20.7983
Malonek S, Bömke C, Bornberg-Bauer E, Rojas MC, Hedden P, Hopkins P, Tudzynski B (2005) Distribution of gibberellin biosynthetic genes and gibberellin production in the Gibberella fujikuroi species complex. Phytochemistry 66:1296–1311. doi: 10.1016/j.phytochem.2005.04.012
Siewers V, Smedsgaard J, Tudzynski P (2004) The P450 Monooxygenase BcABA1 Is Essential for Abscisic Acid Biosynthesis in Botrytis cinerea. Appl Environ Microbiol 70:3868–3876. doi: 10.1128/AEM.70.7.3868-3876.2004
Siewers V, Kokkelink L, Smedsgaard J, Tudzynski P (2006) Identification of an abscisic acid gene cluster in the grey mold Botrytis cinerea. Appl Environ Microbiol 72:4619–4626. doi: 10.1128/AEM.02919-05
Boettcher C, Fellermeier M, Boettcher C, Dräger B, Zenk MH (2005) How human neuroblastoma cells make morphine. Proc Natl Acad Sci USA 102:8495–8500. doi: 10.1073/pnas.0503244102
Crozier A, Yokota T, Bishop GJ, Kamiya Y (2000) Biosynthesis of hormones and elicitors molecules. In: Buchanan BB, Gruissem W, Jones RL (eds) Biochemistry and Molecular Biology of Plants. American Society of Plant Physiologists, Rockville, MD, pp 850–929
Bishop GJ, Yokota T (2001) Plants steroid hormones, brassinosteroids: current highlights of molecular aspects on their synthesis/metabolism, transport, perception and response. Plant Cell Physiol 42:114–120. doi: 10.1093/pcp/pce018
Clouse SD (2002) Brassinosteroids: September 30, 2002. The Arabidopsis Book. Rockville, MD: American Society of Plant Biologists. doi: 10.1199/tab.0009 http://www.aspb.org/publications/arabidopsis/
Asami T, Nakano T, Fujioka S (2005) Plant brassinosteroid hormones. Vitam Horm 72:479–504. doi: 10.1016/S0083-6729(05)72014-8
Cytochrome P450 Homepage: http://drnelson.utmem.edu/cytochromeP450.html
Finkelstein RR, Rock CD (2002) Brassinosteroids: September 30, 2002. The Arabidopsis Book. Rockville, MD: American Society of Plant Biologists. doi: 10.1199/tab.0058 http://www.aspb.org/publications/arabidopsis/
Kushiro T, Okamoto M, Nakabayashi K, Yamagishi K, Kitamura S, Asami T, Hirai N, Koshiba T, Kamiya Y, Nambara E (2004) The Arabidopsis cytochrome P450 CYP707A encodes ABA 8’-hydroxylases: key enzymes in ABA catabolism. EMBO J 23:1647–1656. doi: 10.1038/sj.emboj.7600121
Saito S, Hirai N, Matsumoto C, Ohigashi H, Ohta D, Sakata K, Mizutani M (2004) Arabidopsis CYP707As encode (+)-abscisic acid 8’-hydroxylase, a key enzyme in the oxidative catabolism of abscisic acid. Plant Physiol 134:1439–1449. doi: 10.1104/pp.103.037614
Ma H, Zhang S, Ji L, Zhu H, Yang S, Fang X, Yang R (2006) Fine mapping and in silico isolation of the EUI1 gene controlling upper internode elongation in rice. Plant Mol Biol 60:87–94. doi: 10.1007/s11103-005-2762-5
Luo A, Qian Q, Yin H, Liu X, Yin C, Lan Y, Tang J, Tang Z, Cao S, Wang X, Xia K, Fu X, Luo D, Chu C (2006) EUI1, encoding a putative cytochrome P450 monooxygenase, regulates internode elongation by modulating gibberellin responses in rice. Plant Cell Physiol 47:181–191. doi: 10.1093/pcp/pci233
Zhu Y, Nomura T, Xu Y, Zhang Y, Peng Y, Mao B, Hanada A, Zhou H, Wang R, Li P, Zhu X, Mander LN, Kamiya Y, Yamaguchi S, He Z (2006) ELONGATED UPPERMOST INTERNODE encodes a cytochrome P450 monooxygenase that epoxidizes gibberellins in a novel deactivation reaction in rice. Plant Cell 18:442–456. doi: 10.1105/tpc.105.038455
Plant hormones http://www.plant-hormones.info/occurrence_of_gas_in_plants.htm
Neff MM, Nguyen SM, Malancharuvil EJ, Fujioka S, Noguchi T, Seto H, Tsubuki M, Honda T, Takatsuto S, Yoshida S, Chory J (1999) BAS1: A gene regulating brassinosteroid levels and light responsiveness in Arabidopsis. Proc Natl Acad Sci USA 96:15316–15323. doi: 10.1073/pnas.96.26.15316
Nakamura M, Satoh T, Tanaka S, Mochizuki N, Yokota T, Nagatani A (2005) Activation of the cytochrome P450 gene, CYP72C1, reduces the levels of active brassinosteroids in vivo. J Exp Bot 56:833–840. doi: 10.1093/jxb/eri073
Takahashi N, Nakazawa M, Shibata K, Yokota T, Ishikawa A, Suzuki K, Kawashima M, Ichikawa T, Shimada H, Matsui M (2005) shk1-D, a dwarf Arabidopsis mutant caused by activation of the CYP72C1 gene, has altered brassinosteroid levels. Plant J 42:13–22. doi: 10.1111/j.1365-313X.2005.02357.x
Turk EM, Fujioka S, Seto H, Shimada Y, Takatsuto S, Yoshida S, Wang H, Torres QI, Ward JM, Murthy G, Zhang J, Walker JC, Neff MM (2005) BAS1 and SOB7 act redundantly to modulate Arabidopsis photomorphogenesis via unique brassinosteroid inactivation mechanisms. Plant J 42:23–34. doi: 10.1111/j.1365-313X.2005.02358.x
Ohnishi T, Nomura T, Watanabe B, Ohta D, Yokota T, Miyagawa H, Sakata K, Mizutani M (2006b) Tomato cytochrome P450 CYP734A7 functions in brassinosteroid catabolism. Phytochemistry 67:1895–1906. doi: 10.1016/j.phytochem.2006.05.042
Lazar G, Goodman HM (2006) MAX1, a regulator of the flavonoid pathway, controls vegetative axillary bud outgrowth in Arabidopsis. Proc Natl Acad Sci USA 103:472–476. doi: 10.1073/pnas.0509463102
Bennett T, Sieberer T, Willett B, Booker J, Luschnig C, Leyser O (2006) The Arabidopsis MAX pathway controls shoot branching by regulating auxin transport. Curr Biol 16:553–563. doi: 10.1016/j.cub.2006.01.058
Stirnberg P, Furner IJ, Ottoline Leyser HM (2007) MAX2 participates in an SCF complex which acts locally at the node to suppress shoot branching. Plant J 50:80–94. doi: 10.1111/j.1365-313X.2007.03032.x
Gotoh O (1992) Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analysis of amino acids and coding nucleotide sequences. J Biol Chem 267:83–90
Kieber JJ (2002) Cytokinins: March 27, 2002. The Arabidopsis Book. Rockville, MD: American Society of Plant Biologists. doi: 10.1199/tab.0063 http://www.aspb.org/publications/arabidopsis/
Takei K, Yamaya T, Sakakibara H (2004) Arabidopsis CYP735A1 and CYP735A2 encode cytokinin hydroxylases that catalyze the biosynthesis of trans-Zeatin. J Biol Chem 279:41866–41872. doi: 10.1074/jbc.M406337200
Weng JK, Li X, Stout J, Chapple C (2008) Independent origins of syringyl lignin in vascular plants. Proc Natl Acad Sci USA 105:7887–7892. doi: 10.1073/pnas.0801696105
Castellarin SD, Di Gaspero G, Marconi R, Nonis A, Peterlunger E, Paillard S, Adam-Blondon AF, Testolin R (2006) Colour variation in red grapevines (Vitis vinifera L.): genomic organisation, expression of flavonoid 3’-hydroxylase, flavonoid 3’,5’-hydroxylase genes and related metabolite profiling of red cyanidin-/blue delphinidin-based anthocyanins in berry skin. BMC Genomics 7:12. doi: 10.1186/1471-2164-7-12
Katsumoto Y, Fukuchi-Mizutani M, Fukui Y, Brugliera F, Holton TA, Karan M, Nakamura N, Yonekura-Sakakibara K, Togami J, Pigeaire A, Tao GQ, Nehra NS, Lu CY, Dyson BK, Tsuda S, Ashikari T, Kusumi T, Mason JG, Tanaka Y (2007) Engineering of the rose flavonoid biosynthetic pathway successfully generated blue-hued flowers accumulating delphinidin. Plant Cell Physiol 48:1589–1600. doi: 10.1093/pcp/pcm131
Croteau R, Kutchan TM, Lewis NG (2000) Natural products (secondary metabolites). In: Buchanan BB, Gruissem W, Jones RL (eds) Biochemistry & Molecular Biology of Plants. American Society of Plant Physiologists, Rockville, MD, pp 1250–1318
Akashi T, Aoki T, Ayabe S (1998) CYP81E1, a cytochrome P450 cDNA of licorice (Glycyrrhiza echinata L.), encodes isoflavone 2’-hydroxylase. Biochem Biophys Res Commun 251:67–70. doi: 10.1006/bbrc.1998.9414
Overkamp S, Hein F, Barz W (2000) Cloning and characterization of eight cytochrome P450 cDNAs from chickpea (Cicer arietinum L.) cell suspension cultures. Plant Sci 155:101–108. doi: 10.1016/S0168-9452(00)00214-4
Liu CJ, Huhman D, Sumner LW, Dixon RA (2003) Regiospecific hydroxylation of isoflavones by cytochrome p450 81E enzymes from Medicago truncatula. Plant J 36:471–484. doi: 10.1046/j.1365-313X.2003.01893.x
Schopfer CR, Kochs G, Lottspeich F, Ebel J (1998) Molecular characterization and functional expression of dihydroxypterocarpan 6a-hydroxylase, an enzyme specific for pterocarpanoid phytoalexin biosynthesis in soybean (Glycine max L.). FEBS Lett 432:182–186. doi: 10.1016/S0014-5793(98)00866-7
Martens S, Forkmann G (1999) Cloning and expression of flavone synthase II from Gerbera hybrids. Plant J 20:611–618. doi: 10.1046/j.1365-313X.1999.00636.x
Akashi T, Aoki T, Ayabe S (1999) Cloning and functional expression of a cytochrome P450 cDNA encoding 2-hydroxyisoflavanone synthase involved in biosynthesis of the isoflavonoid skeleton in licorice. Plant Physiol 121:821–828. doi: 10.1104/pp.121.3.821
Jung W, Yu O, Lau S-MC, O’Keefe DP, Odell J, Fader G, McGonigle B (2000) Identification and expression of isoflavone synthase, the key enzyme for biosynthesis of isoflavones in legumes. Nat Biotechnol 18:208–212. doi: 10.1038/72671
Sawada Y, Kinoshita K, Akashi T, Aoki T, Ayabe SI (2002) Key amino acid residues required for aryl migration catalysed by the cyrochrome P450 2-hydroxyisoflavanone synthase. Plant J 31:555–564. doi: 10.1046/j.1365-313X.2002.01378.x
Kim BG, Kim SY, Song HS, Lee C, Hur HG, Kim SI, Ahn JH (2003) Cloning and expression of the isoflavone synthase gene (IFS-Tp) from Trifolium pratense. Mol Cells 15:301–306
Shibuya M, Hoshino M, Katsube Y, Hayashi H, Kushiro T, Ebizuka Y (2006) Identification of beta-amyrin and sophoradiol 24-hydroxylase by expressed sequence tag mining and functional expression assay. FEBS J 273:948–959. doi: 10.1111/j.1742-4658.2006.05120.x
Latunde-Dada AO, Cabello-Hurtado F, Czittrich N, Didierjean L, Schopfer C, Hertkorn N, Werck-Reichhart D, Ebel J (2001) Flavonoid 6-hydroxylase from soybean (Glycine max L.), a novel plant P-450 monooxygenase. J Biol Chem 276:1688–1695
Luo P, Wang YH, Wang GD, Essenberg M, Chen XY (2001) Molecular cloning and functional identification of (+)-delta-cadinene-8-hydroxylase, a cytochrome P450 mono-oxygenase (CYP706B1) of cotton sesquiterpene biosynthesis. Plant J 28:95–104. doi: 10.1046/j.1365-313X.2001.01133.x
Haudenschild C, Schalk M, Karp F, Croteau R (2000) Functional expression of regiospecific cytochrome P450 limonene hydroxylases from Mint (Mentha spp.) in Escherichia coli and Saccharomyces cerevisiae. Arch Biochem Biophys 379:127–136. doi: 10.1006/abbi.2000.1864
Schalk M, Croteau R (2000) A single amino acid substitution (F363I) converts the regiochemistry of the spearmint (-)-limonene hydroxylase from a C6- to a C3-hydroxylase. Proc Natl Acad Sci USA 97:11948–11953. doi: 10.1073/pnas.97.22.11948
Halkier BA (1999) Glucosinolates. In: Ikan R (ed) Naturally Occurring Glucosides. Wiley & Sons Ltd., New York, pp 193–223
Hull AK, Vij R, Celenza JL (2000) Arabidopsis cytochrome P450s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis. Proc Natl Acad Sci USA 97:2379–2384. doi: 10.1073/pnas.040569997
Mikkelsen MD, Hansen CH, Wittstock U, Halkier BA (2000) Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid. J Biol Chem 275:33712–33717. doi: 10.1074/jbc.M001667200
Bak S, Feyereisen R (2001) The involvement of two p450 enzymes, CYP83B1 and CYP83A1, in auxin homeostasis and glucosinolate biosynthesis. Plant Physiol 127:108–118. doi: 10.1104/pp.127.1.108
Bak S, Tax FE, Feldmann KA, Galbraith DW, Feyereisen R (2001) CYP83B1, a cytochrome P450 at the metabolic branch point in auxin and indole glucosinolate biosynthesis in Arabidopsis. Plant Cell 13:101–111
Naur P, Petersen BL, Mikkelsen MD, Bak S, Rasmussen H, Olsen CE, Halkier BA (2003) CYP83A1 and CYP83B1, two nonredundant cytochrome P450 enzymes metabolizing oximes in the biosynthesis of glucosinolates in Arabidopsis. Plant Physiol 133:63–72. doi: 10.1104/pp.102.019240
Hansen CH, Wittstock U, Olsen CE, Hick AJ, Pickett JA, Halkier BA (2001) Cytochrome p450 CYP79F1 from Arabidopsis catalyzes the conversion of dihomomethionine and trihomomethionine to the corresponding aldoximes in the biosynthesis of aliphatic glucosinolates. J Biol Chem 276:11078–11085. doi: 10.1074/jbc.M010123200
Reintanz B, Lehnen M, Reichelt M, Gershenzon J, Kowalczyk M, Sandberg G, Godde M, Uhl R, Palme K (2001) Bus, a bushy Arabidopsis CYP79F1 knockout mutant with abolished synthesis of short-chain aliphatic glucosinolates. Plant Cell 13:351–367
Chen S, Glawischnig E, Jørgensen K, Naur P, Jørgensen B, Olsen CE, Hansen CH, Rasmussen H, Pickett JA, Halkier BA (2003) CYP79F1 and CYP79F2 have distinct functions in the biosynthesis of aliphatic glucosinolates in Arabidopsis. Plant J 33:923–937. doi: 10.1046/j.1365-313X.2003.01679.x
Hemm MR, Ruegger MO, Chapple C (2003) The Arabidopsis ref2 mutant is defective in the gene encoding CYP83A1 and shows both phenylpropanoid and glucosinolate phenotypes. Plant Cell 15:179–194. doi: 10.1105/tpc.006544
Bak S, Paquette SM, Morant M, Morant AV, Saito S, Bjarnholt N, Zagrobelny M, Jørgensen K, Hamann T, Osmani S, Simonsen HT, Pérez RS, van Heeswijck TB, Jørgensen B, Møller BL (2006) Cyanogenic glucosides: a case study for evolution and application of cytochromes P450. Phytochem Rev 5:309–329. doi: 10.1007/s11101-006-9033-1
Nielsen KA, Tattersall DB, Jones PR, Møller BL (2008) Metabolon formation in dhurrin biosynthesis. Phytochemistry 69:88–98. doi: 10.1016/j.phytochem.2007.06.033
Irmler S, Schröder G, St-Pierre B, Crouch NP, Hotze M, Schmidt J, Strack D, Matern U, Schröder J (2000) Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase. Plant J 24:797–804. doi: 10.1046/j.1365-313x.2000.00922.x
Schröder G, Unterbusch E, Kaltenbach M, Schmidt J, Strack D, De Luca V, Schröder J (1999) Light-induced cytochrome P450-dependent enzyme in indole alkaloid biosynthesis: tabersonine 16-hydroxylase. FEBS Lett 458:97–102. doi: 10.1016/S0014-5793(99)01138-2
Collu G, Unver N, Peltenburg-Looman AM, van der Heijden R, Verpoorte R, Memelink J (2001) Geraniol 10-hydroxylase, a cytochrome P450 enzyme involved in terpenoid indole alkaloid biosynthesis. FEBS Lett 508:215–220. doi: 10.1016/S0014-5793(01)03045-9
Tamaki K, Imaishi H, Ohkawa H, Oono K, Sugimoto M (2005) Cloning, expression in yeast, and functional characterization of CYP76A4, a novel cytochrome P450 of petunia that catalyzes (omega-1)-hydroxylation of lauric acid. Biosci Biotechnol Biochem 69:406–409. doi: 10.1271/bbb.69.406
Imaishi H, Petkova-Andonova M (2007) Molecular cloning of CYP76B9, a cytochrome P450 from Petunia hybrida, catalyzing the omega-hydroxylation of capric acid and lauric acid. Biosci Biotechnol Biochem 71:104–113. doi: 10.1271/bbb.60396
Ralston L, Kwon ST, Schoenbeck M, Ralston J, Schenk DJ, Coates RM, Chappell J (2001) Cloning, heterologous expression, and functional characterization of 5-epi-aristolochene-1,3-dihydroxylase from tobacco (Nicotiana tabacum). Arch Biochem Biophys 393:222–235. doi: 10.1006/abbi.2001.2483
Kandel S, Morant M, Benveniste I, Blée E, Werck-Reichhart D, Pinot F (2005) Cloning, functional expression, and characterization of CYP709C1, the first sub-terminal hydroxylase of long chain fatty acid in plants. Induction by chemicals and methyl jasmonate. J Biol Chem 280:35881–35889. doi: 10.1074/jbc.M500918200
Pauli HH, Kutchan TM (1998) Molecular cloning and functional heterologous expression of two alleles encoding (S)-N-methylcoclaurine 3’-hydroxylase (CYP80B1), a new methyl jasmonate-inducible cytochrome P-450-dependent mono-oxygenase of benzylisoquinoline alkaloid biosynthesis. Plant J 13:793–801. doi: 10.1046/j.1365-313X.1998.00085.x
Apuya NR, Park JH, Zhang L, Ahyow M, Davidow P, Van Fleet J, Rarang JC, Hippley M, Johnson TW, Yoo HD, Trieu A, Krueger S, Wu CY, Lu YP, Flavell RB, Bobzin SC (2008) Enhancement of alkaloid production in opium and California poppy by transactivation using heterologous regulatory factors. Plant Biotechnol J 6:160–175. doi: 10.1111/j.1467-7652.2007.00302.x
Kraus PF, Kutchan TM (1995) Molecular cloning and heterologous expression of a cDNA encoding berbamunine synthase, a C–O phenol-coupling cytochrome P450 from the higher plant Berberis stolonifera. Proc Natl Acad Sci USA 92:2071–2075. doi: 10.1073/pnas.92.6.2071
Li R, Reed DW, Liu E, Nowak J, Pelcher LE, Page JE, Covello PS (2006) Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement. Chem Biol 13:513–520. doi: 10.1016/j.chembiol.2006.03.005
Ikezawa N, Iwasa K, Sato F (2008) Molecular cloning and characterization of CYP80G2, a cytochrome P450 that catalyzes an intramolecular C-C phenol coupling of (S)-reticuline in magnoflorine biosynthesis, from cultured Coptis japonica cells. J Biol Chem 283:8810–8821. doi: 10.1074/jbc.M705082200
Minami H, Kim JS, Ikezawa N, Takemura T, Katayama T, Kumagai H, Sato F (2008) Microbial production of plant benzylisoquinoline alkaloids. Proc Natl Acad Sci USA 105:7393–7398. doi: 10.1073/pnas.0802981105
Gavilano LB, Siminszky B (2007) Isolation and characterization of the cytochrome P450 gene CYP82E5v2 that mediates nicotine to nornicotine conversion in the green leaves of tobacco. Plant Cell Physiol 48:1567–1574. doi: 10.1093/pcp/pcm128
Chakrabarti M, Bowen SW, Coleman NP, Meekins KM, Dewey RE, Siminszky B (2008) CYP82E4-mediated nicotine to nornicotine conversion in tobacco is regulated by a senescence-specific signaling pathway. Plant Mol Biol 66:415–427. doi: 10.1007/s11103-007-9280-6
Kruse T, Ho K, Yoo HD, Johnson T, Hippely M, Park JH, Flavell R, Bobzin S (2008) In planta biocatalysis screen of P450s identifies 8-methoxypsoralen as a substrate for the CYP82C subfamily, yielding original chemical structures. Chem Biol 15:149–156. doi: 10.1016/j.chembiol.2008.01.008
Nelson DR, Zeldin DC, Hoffman SM, Maltais LJ, Wain HM, Nebert DW (2004b) Comparison of cytochrome P450 (CYP) genes from the mouse and human genomes, including nomenclature recommendations for genes, pseudogenes and alternative-splice variants. Pharmacogenetics 14:1–18. doi: 10.1097/00008571-200401000-00001
Lodeiro S, Xiong Q, Wilson WK, Kolesnikova MD, Onak CS, Matsuda SP (2007) An oxidosqualene cyclase makes numerous products by diverse mechanisms: a challenge to prevailing concepts of triterpene biosynthesis. J Am Chem Soc 129:11213–11222. doi: 10.1021/ja073133u
Husselstein-Muller T, Schaller H, Benveniste P (2001) Molecular cloning and expression in yeast of 2,3-oxidosqualene-triterpenoid cyclases from Arabidopsis thaliana. Plant Mol Biol 45:75–92. doi: 10.1023/A:1006476123930
Shimura K, Okada A, Okada K, Jikumaru Y, Ko KW, Toyomasu T, Sassa T, Hasegawa M, Kodama O, Shibuya N, Koga J, Nojiri H, Yamane H (2007) Identification of a biosynthetic gene cluster in rice for momilactones. J Biol Chem 282:34013–34018. doi: 10.1074/jbc.M703344200
Otomo K, Kanno Y, Motegi A, Kenmoku H, Yamane H, Mitsuhashi W, Oikawa H, Toshima H, Itoh H, Matsuoka M, Sassa T, Toyomasu T (2004) Diterpene cyclases responsible for the biosynthesis of phytoalexins, momilactones A, B, and oryzalexins A-F in rice. Biosci Biotechnol Biochem 68:2001–2006. doi: 10.1271/bbb.68.2001
Perrin RM, Fedorova ND, Bok JW, Cramer RA, Wortman JR, Kim HS, Nierman WC, Keller NP (2007) Transcriptional regulation of chemical diversity in Aspergillus fumigatus by LaeA. PLoS Pathog 3(4):e50. doi: 10.1371/journal.ppat.0030050
Kelly DE, Kraševec N, Mullins J, Nelson DR (2008) The CYPome (Cytochrome P450 complement) of Aspergillus nidulans. Fungal Genet Biol 2008(Sep):12. Epub ahead of print.
Meyer K, Cusumano J, Somerville C, Chapple C (1996) Ferulate-5-hydroxylase from Arabidopsis thaliana defines a new family of cytochrome P450-dependent monoxygenases. Proc Natl Acad Sci USA 93:6869–6874. doi: 10.1073/pnas.93.14.6869
Ruegger M, Meyer K, Cusumano JC, Chapple C (1999) Regulation of ferulate-5-hydroxylase expression in Arabidopsis in the context of sinapate ester biosynthesis. Plant Physiol 119:101–110. doi: 10.1104/pp.119.1.101
Humphreys JM, Hemm MR, Chapple C (1999) New routes for lignin biosynthesis defined by biochemical characterization of recombinant ferulate 5-hydroxylase, a multifunctional cytochrome P450-dependent monooxygenase. Proc Natl Acad Sci USA 96:10045–10050. doi: 10.1073/pnas.96.18.10045
Bozak KR, Yu H, Sirevåg R, Christoffersen RE (1990) Sequence analysis of ripening-related cytochrome P-450 cDNAs from avocado fruit. Proc Natl Acad Sci USA 87:3904–3908. doi: 10.1073/pnas.87.10.3904
Pua EC, Lee YC (2003) Expression of a ripening-related cytochrome P450 cDNA in Cavendish banana (Musa acuminata cv. Williams). Gene 305:133–140. doi: 10.1016/S0378-1119(02)01237-4
Aharoni A, Giri AP, Verstappen FW, Bertea CM, Sevenier R, Sun Z, Jongsma MA, Schwab W, Bouwmeester HJ (2004) Gain and loss of fruit flavor compounds produced by wild and cultivated strawberry species. Plant Cell 16:3110–3131. doi: 10.1105/tpc.104.023895
Jansen RK, Kaittanis C, Saski C, Lee SB, Tomkins J, Alverson AJ, Daniell H (2006) Phylogenetic analyses of Vitis (Vitaceae) based on complete chloroplast genome sequences: effects of taxon sampling and phylogenetic methods on resolving relationships among rosids. BMC Evol Biol 6:32. doi: 10.1186/1471-2148-6-32
Lyons E, Pedersen B, Kane J, Freeling M (2008) The value of nonmodel genomes and an example using SynMap within CoGe to dissect the hexaploidy that predates the rosids. Trop Plant Biol. doi: 10.1007/s12042-008-9017-y .
This P, Lacombe T, Thomas MR (2006) Historical origins and genetic diversity of wine grapes. Trends Genet 22:511–519. doi: 10.1016/j.tig.2006.07.008
Zhu XY, Chase MW, Qiu YL, Kong HZ, Dilcher DL, Li JH, Chen ZD (2007) Mitochondrial matR sequences help to resolve deep phylogenetic relationships in rosids. BMC Evol Biol 7:217. doi: 10.1186/1471-2148-7-217