Purdue University Logo
Department of Horticulture and Landscape Architecture
 
Horticulture Home Page
Agriculture Home Page
Purdue Home Page
Blackboard
HORT640 Home Page
N Use By Plants
Nitrate Assimilation
Ammonia Assimilation
Glu, Gln, Asn, Gly, Ser
Aminotransferases
Asp, Ala, GABA
Val, Leu, Ileu, Thr, Lys
Pro, Arg, Orn
Polyamines
Non-protein AAs
Alkaloids
Sulfate Assimilation
Cys, Met, AdoMet, ACC
His, Phe, Tyr, Tryp
Secondary Products
Onium Compounds
Enzymes
Methods
Simulation
References
HORT640 - Metabolic Plant Physiology

References, cinnamate or coumarate

Abd El-Mawla AM, Beerhues L. Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum. Planta 214: 727-733 (2002).

Achnine L, Blancaflor EB, Rasmussen S, Dixon RA. Colocalization of L-phenylalanine ammonia-lyase and cinnamate 4-hydroxylase for metabolic channeling in phenylpropanoid biosynthesis. Plant Cell 16: 3098-3109 (2004).

Allina SM, Pri-Hadash A, Theilmann DA, Ellis BE, Douglas CJ. 4-Coumarate:coenzyme A ligase in hybrid poplar. Properties of native enzymes, cDNA cloning, and analysis of recombinant enzymes. Plant Physiol. 116: 743-754 (1998).

Anterola AM, Jeon JH, Davin LB, Lewis NG. Transcriptional control of monolignol biosynthesis in Pinus taeda - Factors affecting monolignol ratios and carbon allocation in phenylpropanoid metabolism. J. Biol. Chem. 277: 18272-18280 (2002).

Anterola AM, Lewis NG. Trends in lignin modification: a comprehensive analysis of the effects of genetic manipulations/mutations on lignification and vascular integrity. Phytochemistry 61: 221-294 (2002).

Baedeker M, Schulz GE. Overexpression of a designed 2.2 kb gene of eukaryotic phenylalanine ammonia-lyase in Escherichia coli. FEBS Lett. 457: 57-60 (1999).

Barillas W, Beerhues L. 3-Hydroxybenzoate:coenzyme A ligase and 4-coumarate:coenzyme A ligase from cultured cells of Centaurium erythraea. Planta 202: 112-116 (1997).

Batz O, Logemann E, Reinold S, Hahlbrock K. Extensive reprogramming of primary and secondary metabolism by fungal elicitor or infection in parsley cells. Biol. Chem. 379: 1127-1135 (1998).

Bell-Lelong DA, Cusumano JC, Meyer K, Chapple C. Cinnamate-4-hydroxylase expression in Arabidopsis. Regulation in response to development and the environment. Plant Physiol. 113: 729-738 (1997).

Beritogoli I, Magel E, Abdel-Latif A, Charpentier JP, Jay-Allemand C, Breton C. Expression of genes encoding chalcone synthase, flavanone 3-hydroxylase and dihydroflavonol 4-reductase correlates with flavanol accumulation during heartwood formation in Juglans nigra. Tree Physiol. 22: 291-300 (2002).

Bernards MA, Fleming WD, Llewellyn DB, Priefer R, Yang X, Sabatino A, Plourde GL. Biochemical characterization of the suberization-associated anionic peroxidase of potato. Plant Physiol. 121: 135-146 (1999).

Betz C, McCollum TG, Mayer RT. Differential expression of two cinnamate 4-hydroxylase genes in 'Valencia' orange (Citrus sinensis Osbeck). Plant Mol. Biol. 46: 741-748 (2001).

Bi HH, Zeng RS, Su LM, An M, Luo SM. Rice allelopathy induced by methyl jasmonate and methyl salicylate. J. Chem. Ecol. 33: 1089-1103 (2007).

Billett EE, Wallace W, Smith H. A specific and reversible macromolecular inhibitor of phenylalanine ammonia-lyase and cinnamic acid-4-hydroxylase in gherkins. Biochim. Biophys. Acta 524: 219-230 (1978).

Bilodeau P, Udvardi MK, Peacock WJ, Dennis ES. A prolonged cold treatment-induced cytochrome P450 gene from Arabidopsis thaliana. Plant Cell Environ. 22: 791-800 (1999).

Blee K, Choi JW, O'Connell AP, Jupe SC, Schuch W, Lewis NG, Bolwell GP. 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 (2001).

Blount JW, Masoud S, Sumner LW, Huhman D, Dixon RA. Over-expression of cinnamate 4-hydroxylase leads to increased accumulation of acetosyringone in elicited tobacco cell-suspension cultures. Planta 214: 902-910 (2002).

Bottcher C, Roepenack-Lahaye EV, Schmidt J, Schmotz C, Neumann S, Scheel D, Clemens S. Metabolome analysis of biosynthetic mutants reveals diversity of metabolic changes and allows identification of a large number of new compounds in Arabidopsis thaliana. Plant Physiol. 147: 2107-2120 (2008).

Burchard P, Bilger W, Weissenbock G. Contribution of hydroxycinnamates and flavonoids to epidermal shielding of UV-A and UV-B radiation in developing rye primary leaves as assessed by ultraviolet-induced chlorophyll fluorescence measurements. Plant Cell Environ. 23: 1373-1380 (2000).

Burr SJ, Fry SC. Extracellular cross-linking of maize arabinoxylans by oxidation of feruloyl esters to form oligoferuloyl esters and ether-like bonds. Plant J. 58: 554-567 (2009).

Canam T, Park JY, Yu KY, Campbell MM, Ellis DD, Mansfield SD. Varied growth, biomass and cellulose content in tobacco expressing yeast-derived invertases. Planta 224: 1315-1327 (2006).

Chen F, Srinivasa Reddy MS, Temple S, Jackson L, Shadle G, Dixon RA. Multi-site genetic modulation of monolignol biosynthesis suggests new routes for formation of syringyl lignin and wall-bound ferulic acid in alfalfa (Medicago sativa L.). Plant J. 48: 113-124 (2006).

Chong J, Pierrel MA, Atanassova R, Werck-Reichhart D, Fritig B, Saindrenan P. Free and conjugated benzoic acid in tobacco plants and cell cultures. Induced accumulation upon elicitation of defense responses and role as salicylic acid precursors. Plant Physiol. 125: 318-328 (2001).

Church DL, Galston AW. 4-Coumarate:coenzyme A ligase and isoperoxidase expression in Zinnia mesophyll cells induced to differentiate into tracheary elements. Plant Physiol. 88: 679-684 (1988).

Cunningham OD, Edwards R. Modifying the acylation of flavonols in Petunia hybrida. Phytochemistry 69: 2016-2021 (2008).

Czichi U, Kindi H. A model of closely assembled consecutive enzymes on membranes: formation of hydroxycinnamic acids from L-phenylalanine on thylakoids of Dunaliella marina. Hoppe Seylers Z. Physiol. Chem. 356: 475-485 (1975).

da Cunha A. Purification, characterization and induction of L-phenylalanine ammonia-lyase in Phaseolus vulgaris. Eur. J. Biochem. 178: 243-248 (1988).

Davin LB, Wang CZ, Helms GL, Lewis NG. [13C]-Specific labeling of 8-2' linked (-)-cis-blechnic, (-)-trans-blechnic and (-)-brainic acids in the fern Blechnum spicant. Phytochemistry 62: 501-511 (2003).

de Azevedo Souza C, Kim SS, Koch S, Kienow L, Schneider K, McKim SM, Haughn GW, Kombrink E, Douglas CJ. A novel fatty Acyl-CoA Synthetase is required for pollen development and sporopollenin biosynthesis in Arabidopsis. Plant Cell 21: 507-525 (2009).

Douglas MH, van Klink JW, Smallfield BM, Perry NB, Anderson RE, Johnstone P, Weavers RT. Essential oils from New Zealand manuka: triketone and other chemotypes of Leptospermum scoparium. Phytochemistry 65: 1255-1264 (2004).

Ehlting J, Buttner D, Wang Q, Douglas CJ, Somssich IE, Kombrink E. Three 4-coumarate:coenzyme A ligases in Arabidopsis thaliana represent two evolutionarily divergent classes in angiosperms. Plant J. 19: 9-20 (1999).

Ehlting J, Shin JJ, Douglas CJ. Identification of 4-coumarate:coenzyme A ligase (4CL) substrate recognition domains. Plant J. 27: 455-465 (2001).

Endler A, Martens S, Wellmann F, Matern U. Unusually divergent 4-coumarate:CoA-ligases from Ruta graveolens L. Plant Mol. Biol. 67: 335-346 (2008).

Franke R, Hemm MR, Denault JW, Ruegger MO, Humphreys JM, Chapple C. Changes in secondary metabolism and deposition of an unusual lignin in the ref8 mutant of Arabidopsis. Plant J. 30: 47-59 (2002).

Franke R, Humphreys JM, Hemm MR, Denault JW, Ruegger MO, Cusumano JC, Chapple C. The Arabidopsis REF8 gene encodes the 3-hydroxylase of phenylpropanoid metabolism. Plant J. 30: 33-45 (2002).

Franke R, McMichael CM, Meyer K, Shirley AM, Cusumano JC, Chapple C. Modified lignin in tobacco and poplar plants over-expressing the Arabidopsis gene encoding ferulate 5-hydroxylase. Plant J. 22: 223-234 (2000).

Franklin G, Conceicao LF, Kombrink E, Dias AC. Xanthone biosynthesis in Hypericum perforatum cells provides antioxidant and antimicrobial protection upon biotic stress. Phytochemistry 70: 60-68 (2009).

Fraser CM, Thompson MG, Shirley AM, Ralph J, Schoenherr JA, Sinlapadech T, Hall MC, Chapple C. Related Arabidopsis serine carboxypeptidase-like sinapoylglucose acyltransferases display distinct but overlapping substrate specificities. Plant Physiol. 144: 1986-1999 (2007).

Fry SC, Willis SC, Paterson AE. Intraprotoplasmic and wall-localised formation of arabinoxylan-bound diferulates and larger ferulate coupling-products in maize cell-suspension cultures. Planta 211: 679-692 (2000).

Galis I, Simek P, Narisawa T, Sasaki M, Horiguchi T, Fukuda H, Matsuoka K. A novel R2R3 MYB transcription factor NtMYBJS1 is a methyl jasmonate-dependent regulator of phenylpropanoid-conjugate biosynthesis in tobacco. Plant J. 46: 573-592 (2006).

Gatto P, Vrhovsek U, Muth J, Segala C, Romualdi C, Fontana P, Pruefer D, Stefanini M, Moser C, Mattivi F, Velasco R. Ripening and genotype control stilbene accumulation in healthy grapes. J. Agric. Food Chem. 56: 11773-11785 (2008).

Gou JY, Park S, Yu XH, Miller LM, Liu CJ. Compositional characterization and imaging of "wall-bound" acylesters of Populus trichocarpa reveal differential accumulation of acyl molecules in normal and reactive woods. Planta 229: 15-24 (2008).

Grabber JH, Lu F. Formation of syringyl-rich lignins in maize as influenced by feruloylated xylans and p-coumaroylated monolignols. Planta 226: 741-751 (2007).

Grace SC, Logan BA. Energy dissipation and radical scavenging by the plant phenylpropanoid pathway. Philos. Trans. R. Soc. Lond. B. Biol. Sci. 355: 1499-1510 (2000).

Hagmann ML, Heller W, Grisebach H. Induction and characterization of a microsomal flavonoid 3'-hydroxylase from parsley cell cultures. Eur. J. Biochem. 134: 547-554 (1983).

Hao ZG, Charles DJ, Yu LL, Simon JE. Purification and characterization of a phenylalanine ammonia- lyase from Ocimum basilicum. Phytochemistry 43: 735-739 (1996).

Harding SA, Leshkevich J, Chiang VL, Tsai CJ. Differential substrate inhibition couples kinetically distinct 4-coumarate:coenzyme A ligases with spatially distinct metabolic roles in quaking aspen. Plant Physiol. 128: 428-438 (2002).

Hatfield R, Ralph J, Grabber JH. A potential role for sinapyl p-coumarate as a radical transfer mechanism in grass lignin formation. Planta 228: 919-928 (2008).

Hatfield RD, Marita JM, Frost K, Grabber J, Ralph J, Lu F, Kim H. Grass lignin acylation: p-coumaroyl transferase activity and cell wall characteristics of C3 and C4 grasses. Planta 229: 1253-1267 (2009).

Hauffe KD, Lee SP, Subramaniam R, Douglas CJ. Combinatorial interactions between positive and negative cis-acting elements control spatial patterns of 4CL-1 expression in transgenic tobacco. Plant J. 4: 235-253 (1993).

Hemm MR, Herrmann KM, Chapple C. AtMYB4: a transcription factor general in the battle against UV. Trends Plant Sci. 6: 135-136 (2001).

Hoffmann L, Besseau S, Geoffroy P, Ritzenthaler C, Meyer D, Lapierre C, Pollet B, Legrand M. Silencing of hydroxycinnamoyl-coenzyme A shikimate/quinate hydroxycinnamoyltransferase affects phenylpropanoid biosynthesis. Plant Cell 16: 1446-1465 (2004).

Howles PA, Sewalt V, Paiva NL, Elkind Y, Bate NJ, Lamb C, Dixon RA. Overexpression of L-phenylalanine ammonia-lyase in transgenic tobacco plants reveals control points for flux into phenylpropanoid biosynthesis. Plant Physiol. 112: 1617-1624 (1996).

Hrazdina G, Wagner GJ. Metabolic pathways as enzyme complexes: evidence for the synthesis of phenylpropanoids and flavonoids on membrane associated enzyme complexes. Arch. Biochem. Biophys. 237: 88-100 (1985).

Hu WJ, Kawaoka A, Tsai CJ, Lung J, Osakabe K, Ebinuma H, Chiang VL. Compartmentalized expression of two structurally and functionally distinct 4-coumarate:CoA ligase genes in aspen (Populus tremuloides). Proc. Natl. Acad. Sci. U.S.A. 95: 5407-5412 (1998).

Jones DH, Northcote DH. Stability of the complex formed between French bean (Phaseolus vulgaris) phenylalanine ammonia-lyase and its transition-state analog. Arch. Biochem. Biophys. 235: 167-177 (1984).

Juvvadi PR, Seshime Y, Kitamoto K. Genomics reveals traces of fungal phenylpropanoid-flavonoid metabolic pathway in the filamentous fungus Aspergillus oryzae. J. Microbiol. 43 :475-486 (2005).

Kai K, Mizutani M, Kawamura N, Yamamoto R, Tamai M, Yamaguchi H, Sakata K, Shimizu BI. Scopoletin is biosynthesized via ortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabidopsis thaliana. Plant J. 55: 989-999 (2008).

Kai K, Shimizu B, Mizutani M, Watanabe K, Sakata K. Accumulation of coumarins in Arabidopsis thaliana. Phytochemistry 67: 379-386 (2006).

Kang K, Back K. Production of phenylpropanoid amides in recombinant Escherichia coli. Metab. Eng. 11: 64-68 (2009).

Kao YY, Harding SA, Tsai CJ. Differential expression of two distinct phenylalanine ammonia-lyase genes in condensed tannin-accumulating and lignifying cells of quaking aspen. Plant Physiol. 130: 796-807 (2002).

Katsuyama Y, Matsuzawa M, Funa N, Horinouchi S. Production of curcuminoids by Escherichia coli carrying an artificial biosynthesis pathway. Microbiology 154: 2620-2628 (2008).

Kauss H, Franke R, Krause K, Conrath U, Jeblick W, Grimmig B, Matern U. Conditioning of parsley (Petroselinum crispum L.) suspension cells increases elicitor-induced incorporation of cell wall phenolics. Plant Physiol. 102: 459-466 (1993).

Kawaoka A, Ebinuma H. Transcriptional control of lignin biosynthesis by tobacco LIM protein. Phytochemistry 57: 1149-1157 (2001).

Kawaoka A, Kaothien P, Yoshida K, Endo S, Yamada K, Ebinuma H. Functional analysis of tobacco LIM protein ntlim1 involved in lignin biosynthesis. Plant J. 22: 289-301 (2000).

Kienow L, Schneider K, Bartsch M, Stuible HP, Weng H, Miersch O, Wasternack C, Kombrink E. Jasmonates meet fatty acids: functional analysis of a new acyl-coenzyme A synthetase family from Arabidopsis thaliana. J. Exp. Bot. 59: 403-419 (2008).

Kim DK, Zee OP. A new cyanogenic glycoside from Sorbaria sorbifolia var. stellipila. Chem. Pharm. Bull. (Tokyo) 48: 1766-1767 (2000).

Koopmann E, Logemann E, Hahlbrock K. Regulation and functional expression of cinnamate 4-hydroxylase from parsley. Plant Physiol. 119: 49-56 (1999).

Krens FA, Keizer LCP, Capel IEM. Transgenic caraway, Carum carvi L.: a model species for metabolic engineering. Plant Cell Rep. 17: 39-43 (1997).

Kuhnl T, Koch U, Heller W, Wellmann E. Chlorogenic acid biosynthesis: characterization of a light-induced microsomal 5-O-(4-coumaroyl)-D-quinate/shikimate 3'-hydroxylase from carrot (Daucus carota L.) cell suspension cultures. Arch. Biochem. Biophys. 258: 226-32 (1987).

Kumar A, Ellis BE. 4-Coumarate:CoA ligase gene family in Rubus idaeus: cDNA structures, evolution, and expression. Plant Mol. Biol. 51: 327-340 (2003).

Landmann C, Fink B, Schwab W. FaGT2: a multifunctional enzyme from strawberry (Fragaria x ananassa) fruits involved in the metabolism of natural and xenobiotic compounds. Planta 226: 417-428 (2007).

Landry LG, Chapple CC, Last RL. Arabidopsis mutants lacking phenolic sunscreens exhibit enhanced ultraviolet-B injury and oxidative damage. Plant Physiol. 109: 1159-1166 (1995).

Lee D, Douglas CJ. Two divergent members of a tobacco 4-coumarate:coenzyme A ligase (4CL) gene family. cDNA structure, gene inheritance and expression, and properties of recombinant proteins. Plant Physiol. 112: 193-205 (1996).

Lee D, Meyer K, Chapple C, Douglas CJ. Antisense suppression of 4-coumarate:coenzyme A ligase activity in Arabidopsis leads to altered lignin subunit composition. Plant Cell 9: 1985-1998 (1997).

Liang YS, Choi YH, Kim HK, Linthorst HJ, Verpoorte R. Metabolomic analysis of methyl jasmonate treated Brassica rapa leaves by 2-dimensional NMR spectroscopy. Phytochemistry 67: 2503-2511 (2006).

Lindermayr C, Mollers B, Fliegmann J, Uhlmann A, Lottspeich F, Meimberg H, Ebel J. Divergent members of a soybean (Glycine max L.) 4-coumarate:coenzyme A ligase gene family. Eur. J. Biochem. 269: 1304-1315 (2002).

Lomascolo A, Asther M, Navarro D, Antona C, Delattre M, Lesage-Meessen L. Shifting the biotransformation pathways of L-phenylalanine into benzaldehyde by Trametes suaveolens CBS 334.85 using HP20 resin. Lett. Appl. Microbiol. 32: 262-267 (2001).

Lomascolo A, Lesage-Meessen L, Labat M, Navarro D, Delattre M, Asther M. Enhanced benzaldehyde formation by a monokaryotic strain of Pycnoporus cinnabarinus using a selective solid adsorbent in the culture medium. Can. J. Microbiol. 45: 653-657 (1999).

Loscher R, Heide L. Biosynthesis of p-hydroxybenzoate from p-coumarate and p-coumaroyl-coenzyme A in cell-free extracts of Lithospermum erythrorhizon cell cultures. Plant Physiol. 106: 271-279 (1994).

Lu S, Zhou Y, Li L, Chiang VL. Distinct roles of cinnamate 4-hydroxylase genes in Populus. Plant Cell Physiol. 47: 905-914 (2006).

Luderitz T, Schatz G, Grisebach H. Enzymic synthesis of lignin precursors. Purification and properties of 4-coumarate:CoA ligase from cambial sap of spruce (Picea abies L.). Eur. J. Biochem. 123: 583-586 (1982).

Lunkenbein S, Bellido M, Aharoni A, Salentijn EM, Kaldenhoff R, Coiner HA, Munoz-Blanco J, Schwab W. Cinnamate metabolism in ripening fruit. Characterization of a UDP-glucose:cinnamate glucosyltransferase from strawberry. Plant Physiol. 140: 1047-1058 (2006).

MacAdam JW, Grabber JH. Relationship of growth cessation with the formation of diferulate cross-links and p-coumaroylated lignins in tall fescue leaf blades. Planta 215: 785-793 (2002).

Mahroug S, Courdavault V, Thiersault M, St-Pierre B, Burlat V. Epidermis is a pivotal site of at least four secondary metabolic pathways in Catharanthus roseus aerial organs. Planta 223: 1191-1200 (2006).

Marita JM, Ralph J, Hatfield RD, Chapple C. NMR characterization of lignins in Arabidopsis altered in the activity of ferulate 5-hydroxylase. Proc. Natl. Acad. Sci. U.S.A. 96: 12328-12332 (1999).

Martinez AT, Rencoret J, Marques G, Gutierrez A, Ibarra D, Jimenez-Barbero J, Del Rio JC. Monolignol acylation and lignin structure in some nonwoody plants: a 2D NMR study. Phytochemistry 69: 2831-2843 (2008).

Mase K, Sato K, Nakano Y, Nishikubo N, Tsuboi Y, Zhou J, Kitano H, Katayama Y. The ectopic expression of phenylalanine ammonia lyase with ectopic accumulation of polysaccharide-linked hydroxycinnamoyl esters in internode parenchyma of rice mutant Fukei 71. Plant Cell Rep. 24: 487-493 (2005).

Mastrangelo LI, Lenucci MS, Piro G, Dalessandro G. Evidence for intra- and extra-protoplasmic feruloylation and cross-linking in wheat seedling roots. Planta 229: 343-355 (2009).

Mayer MJ, Narbad A, Parr AJ, Parker ML, Walton NJ, Mellon FA, Michael AJ. Rerouting the plant phenylpropanoid pathway by expression of a novel bacterial enoyl-CoA hydratase/lyase enzyme function. Plant Cell 13: 1669-1682 (2001).

MeiBner D, Albert A, Bottcher C, Strack D, Milkowski C. The role of UDP-glucose:hydroxycinnamate glucosyltransferases in phenylpropanoid metabolism and the response to UV-B radiation in Arabidopsis thaliana. Planta 228: 663-674 (2008).

Meijer AH, Lopes Cardoso MI, Voskuilen JT, de Waal A, Verpoorte R, Hoge JH. Isolation and characterization of a cDNA clone from Catharanthus roseus encoding NADPH:cytochrome P-450 reductase, an enzyme essential for reactions catalysed by cytochrome P-450 mono-oxygenases in plants. Plant J. 4: 47-60 (1993).

Melida H, García-Angulo P, Alonso-Simon A, Encina A, Alvarez J, Acebes JL. Novel type II cell wall architecture in dichlobenil-habituated maize calluses. Planta 229: 617-631 (2009).

Meyer K, Cusumano JC, Somerville C, Chapple CC. Ferulate-5-hydroxylase from Arabidopsis thaliana defines a new family of cytochrome P450-dependent monooxygenases. Proc. Natl. Acad. Sci. U.S.A. 93: 6869-6874 (1996).

Meyer K, Shirley AM, Cusumano JC, Bell-Lelong DA, Chapple C. Lignin monomer composition is determined by the expression of a cytochrome P450-dependent monooxygenase in Arabidopsis. Proc. Natl. Acad. Sci. U.S.A. 95: 6619-6623 (1998).

Milkowski C, Baumert A, Strack D. Cloning and heterologous expression of a rape cDNA encoding UDP-glucose:sinapate glucosyltransferase. Planta 211: 883-886 (2000).

Millar DJ, Long M, Donovan G, Fraser PD, Boudet AM, Danoun S, Bramley PM, Bolwell GP. Introduction of sense constructs of cinnamate 4-hydroxylase (CYP73A24) in transgenic tomato plants shows opposite effects on flux into stem lignin and fruit flavonoids. Phytochemistry 68: 1497-1509 (2007).

Mittasch J, Strack D, Milkowski C. Secondary product glycosyltransferases in seeds of Brassica napus. Planta 225: 515-522 (2007).

Mizutani M, Ohta D, Sato R. Isolation of a cDNA and a genomic clone encoding cinnamate 4-hydroxylase from Arabidopsis and its expression manner in planta. Plant Physiol. 113: 755-763 (1997).

Moffitt MC, Louie GV, Bowman ME, Pence J, Noel JP, Moore BS. Discovery of two cyanobacterial phenylalanine ammonia lyases: kinetic and structural characterization. Biochemistry 46: 1004-1012 (2007).

Mondolot L, LA Fisca P, Buatois B, Talansier E, DE Kochko A, Campa C. Evolution in caffeoylquinic acid content and histolocalization during Coffea canephora leaf development. Ann. Bot. (Lond.) 98: 33-40 (2006).

Nair RB, Xia Q, Kartha CJ, Kurylo E, Hirji RN, Datla R, Selvaraj G. Arabidopsis CYP98A3 mediating aromatic 3-hydroxylation. Developmental regulation of the gene, and expression in yeast. Plant Physiol. 130: 210-220 (2002).

Nedelkina S, Jupe SC, Blee KA, Schalk M, Werck-Reichhart D, Bolwell GP. Novel characteristics and regulation of a divergent cinnamate 4-hydroxylase (CYP73A15) from French bean: engineering expression in yeast. Plant Mol. Biol. 39: 1079-1090 (1999).

Negrel J, Javelle F. Induction of phenylpropanoid and tyramine metabolism in pectinase- or pronase-elicited cell suspension cultures of tobacco (Nicotiana tabacum). Physiol. Plant. 95: 569-574 (1995).

Neustaedter DA, Lee SP, Douglas CJ. A novel parsley 4CL1 cis-element is required for developmentally regulated expression and protein-DNA complex formation. Plant J. 18: 77-88 (1999).

O'Looney N, Fry SC. Oxaziclomefone, a new herbicide, inhibits wall expansion in maize cell-cultures without affecting polysaccharide biosynthesis, xyloglucan transglycosylation, peroxidase action or apoplastic ascorbate oxidation. Ann. Bot. (Lond.) 96: 1097-1107 (2005).

Parveen I, Winters A, Threadgill MD, Hauck B, Morris P. Extraction, structural characterisation and evaluation of hydroxycinnamate esters of orchard grass (Dactylis glomerata) as substrates for polyphenol oxidase. Phytochemistry 69: 2799-2806 (2008).

Pietrowska-Borek M, Stuible HP, Kombrink E, Guranowski A. 4-Coumarate:coenzyme A ligase has the catalytic capacity to synthesize and reuse various (di)adenosine polyphosphates. Plant Physiol. 131: 1401-1410 (2003).

Preston J, Wheeler J, Heazlewood J, Li SF, Parish RW. AtMYB32 is required for normal pollen development in Arabidopsis thaliana. Plant J. 40: 979-995 (2004).

Ralph J, Akiyama T, Kim H, Lu F, Schatz PF, Marita JM, Ralph SA, Srinivasa Reddy MS, Chen F, Dixon RA. Effects of coumarate 3-hydroxylase down-regulation on lignin structure. J. Biol. Chem. 281: 8843-8853 (2006).

Ramos RLB, Tovar FJ, Junqueira RM, Lino FB, Sachetto-Martins G. Sugarcane expressed sequences tags (ESTs) encoding enzymes involved in lignin biosynthesis pathways. Genet. Mol. Biol. 24: 235-241 (2001).

Ranjan P, Kao YY, Jiang H, Joshi CP, Harding SA, Tsai CJ. Suppression subtractive hybridization-mediated transcriptome analysis from multiple tissues of aspen (Populus tremuloides) altered in phenylpropanoid metabolism. Planta 219: 694-704 (2004).

Rasmussen S, Dixon RA. Transgene-mediated and elicitor-induced perturbation of metabolic channeling at the entry point into the phenylpropanoid pathway. Plant Cell 11: 1537-1552 (1999).

Razal RA, Ellis S, Singh S, Lewis NG, Towers GHN. Nitrogen recycling in phenylpropanoid metabolism. Phytochemistry 41: 31-35 (1996).

Reinold S, Hauffe KD, Douglas CJ. Tobacco and parsley 4-coumarate:coenzyme A ligase genes are temporally and spatially regulated in a cell type-specific manner during tobacco flower development. Plant Physiol. 101: 373-383 (1993).

Ro DK, Ehlting J, Douglas CJ. Cloning, functional expression, and subcellular localization of multiple NADPH-cytochrome P450 reductases from hybrid poplar. Plant Physiol. 130: 1837-1851 (2002).

Ro DK, Mah N, Ellis BE, Douglas CJ. Functional characterization and subcellular localization of poplar (Populus trichocarpa x Populus deltoides) cinnamate 4-hydroxylase. Plant Physiol. 126: 317-329 (2001).

Schalk M, Batard Y, Seyer A, Nedelkina S, Durst F, Werck-Reichhart D. Design of fluorescent substrates and potent inhibitors of CYP73As, P450s that catalyze 4-hydroxylation of cinnamic acid in higher plants. Biochemistry 36: 15253-15261 (1997).

Schalk M, Cabello-Hurtado F, Pierrel MA, Atanossova R, Saindrenan P, Werck-Reichhart D. 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 (1998).

Schoch GA, Attias R, Belghazi M, Dansette PM, Werck-Reichhart D. 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 (2003).

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

Seidel V, Windhovel J, Eaton G, Alfermann AW, Arroo RR, Medarde M, Petersen M, Woolley JG. Biosynthesis of podophyllotoxin in Linum album cell cultures. Planta 215: 1031-1039 (2002).

Seshime Y, Juvvadi PR, Fujii I, Kitamoto K. Genomic evidences for the existence of a phenylpropanoid metabolic pathway in Aspergillus oryzae. Biochem. Biophys. Res. Commun. 337: 747-751 (2005).

Sewalt VJH, Ni WT, Blount JW, Jung HG, Masoud SA, Howles PA, Lamb C, Dixon RA. Reduced lignin content and altered lignin composition in transgenic tobacco down-regulated in expression of L-phenylalanine ammonia-lyase or cinnamate 4-hydroxylase. Plant Physiol. 115: 41-50 (1997).

Shockey JM, Fulda MS, Browse J. Arabidopsis contains a large superfamily of acyl-activating enzymes. Phylogenetic and biochemical analysis reveals a new class of acyl-coenzyme A synthetases. Plant Physiol. 132: 1065-1076 (2003).

Silber MV, Meimberg H, Ebel J. Identification of a 4-coumarate:CoA ligase gene family in the moss, Physcomitrella patens. Phytochemistry 69: 2449-2456 (2008).

Singh S, Lewis NG, Towers GH. Nitrogen recycling during phenylpropanoid metabolism in sweet potato tubers. J. Plant Physiol. 153: 316-323 (1998).

Sircar D, Mitra A. Accumulation of p-hydroxybenzoic acid in hairy roots of Daucus carota 2: confirming biosynthetic steps through feeding of inhibitors and precursors. J. Plant Physiol. 166: 1370-1380 (2009).

Smith MA, Weaver VB, Young DM, Ornston LN. Genes for chlorogenate and hydroxycinnamate catabolism (hca) are linked to functionally related genes in the dca-pca-qui-pob-hca chromosomal cluster of Acinetobacter sp. strain ADP1. Appl. Environ. Microbiol. 69: 524-532 (2003).

Soltani BM, Ehlting J, Hamberger B, Douglas CJ. Multiple cis-regulatory elements regulate distinct and complex patterns of developmental and wound-induced expression of Arabidopsis thaliana 4CL gene family members. Planta 224: 1226-1238 (2006).

Stewart JJ, Akiyama T, Chapple C, Ralph J, Mansfield SD. The effects on lignin structure of overexpression of ferulate 5-hydroxylase in hybrid poplar. Plant Physiol. 150: 621-635 (2009).

Suita K, Kiryu T, Sawada M, Mitsui M, Nakagawa M, Kanamaru K, Yamagata H. Cyclic GMP acts as a common regulator for the transcriptional activation of the flavonoid biosynthetic pathway in soybean. Planta 229: 403-413 (2009).

Tattini M, Guidi L, Morassi-Bonzi L, Pinelli P, Remorini D, Degl'innocenti E, Giordano C, Massai R, Agati G. On the role of flavonoids in the integrated mechanisms of response of Ligustrum vulgare and Phillyrea latifolia to high solar radiation. New Phytol. 167: 457-470 (2005).

Thulke O, Conrath U. Salicylic acid has a dual role in the activation of defence-related genes in parsley. Plant J. 14: 35-42 (1998).

van der Rest B, Danoun S, Boudet AM, Rochange SF. Down-regulation of cinnamoyl-CoA reductase in tomato (Solanum lycopersicum L.) induces dramatic changes in soluble phenolic pools. J. Exp. Bot. 57: 1399-1411 (2006).

Viergutz S, Retey J. Kinetic analysis of the reactions catalyzed by histidine and phenylalanine ammonia lyases. Chem. Biodivers. 1: 296-302 (2004).

Voo KS, Whetten RW, O'Malley DM, Sederoff RR. 4-Coumarate:coenzyme A ligase from loblolly pine xylem. Isolation, characterization, and complementary DNA cloning. Plant Physiol. 108: 85-97 (1995).

Wagner A, Donaldson L, Kim H, Phillips L, Flint H, Steward D, Torr K, Koch G, Schmitt U, Ralph J. Suppression of 4-coumarate-CoA ligase in the coniferous gymnosperm Pinus radiata. Plant Physiol. 149: 370-383 (2009).

Wakabayashi K, Soga K, Kamisaka S, Hoson T. Increase in the level of arabinoxylan-hydroxycinnamate network in cell walls of wheat coleoptiles grown under continuous hypergravity conditions. Physiol. Plant. 125: 127-134 (2005).

Werck-Reichhart D. Cytochromes P450 in phenylpropanoid metabolism. Drug Metabol. Drug Interact. 12: 221-243 (1995).

Whitbred JM, Schuler MA. Molecular characterization of CYP73A9 and CYP82A1 P450 genes involved in plant defense in pea. Plant Physiol. 124: 47-58 (2000).

Winkel-Shirley B. Evidence for enzyme complexes in the phenylpropanoid and flavonoid pathways. Physiol. Plant. 107: 142-149 (1999).

Wittmann C, Hans M, Bluemke W. Metabolic physiology of aroma-producing Kluyveromyces marxianus. Yeast 19: 1351-1363 (2002).

Wright GA, Lutmerding A, Dudareva N, Smith BH. Intensity and the ratios of compounds in the scent of snapdragon flowers affect scent discrimination by honeybees (Apis mellifera). J. Comp. Physiol. A. Neuroethol. Sens. Neural. Behav. Physiol. 191: 105-114 (2005).

Xiao H, Parkin KL. Isolation and identification of potential cancer chemopreventive agents from methanolic extracts of green onion (Allium cepa). Phytochemistry 68: 1059-1067 (2007).

Yamauchi K, Yasuda S, Hamada K, Tsutsumi Y, Fukushima K. Multiform biosynthetic pathway of syringyl lignin in angiosperms. Planta 216: 496-501 (2003).

Zhang J, Turley RB, Stewart JM. Comparative analysis of gene expression between CMS-D8 restored plants and normal non-restoring fertile plants in cotton by differential display. Plant Cell Rep. 27: 553-561 (2008).

Zhang L, Robbins MP, Carver TLW, Zeyen RJ. Induction of phenylpropanoid gene transcripts in oat attacked by Erysiphe graminis at 20 degrees C and 10 degrees C. Physiol. Mol. Plant Pathol. 51: 15-33 (1997).

Zhang XH, Chiang VL. Molecular cloning of 4-coumarate:coenzyme A ligase in loblolly pine and the roles of this enzyme in the biosynthesis of lignin in compression wood. Plant Physiol. 113: 65-74 (1997).

Zhong R, Morrison WH 3rd, Himmelsbach DS, Poole FL 2nd, Ye ZH. Essential role of caffeoyl coenzyme A O-methyltransferase in lignin biosynthesis in woody poplar plants. Plant Physiol. 124: 563-578 (2000).

Number of references = 150

| PubMed Search | Entrez Protein Search | ISI Web of Knowledge Search | Scirus Search |

David Rhodes
Department of Horticulture & Landscape Architecture
Horticulture Building
625 Agriculture Mall Drive
Purdue University
West Lafayette, IN 47907-2010
Last Update: 10/01/09