Skip to main content
SpringerLink
Log in

Hydroxycinnamoyltransferases in plant metabolism

  • Published:
Phytochemistry Reviews Aims and scope Submit manuscript

Abstract

Hydroxycinnamoyltransferases are enzymes transferring hydroxycinnamoyl units like cinnamoyl, 4-coumaroyl, caffeoyl, feruloyl and sinapoyl moieties from an activating residue such as coenzyme A or glucose or activated as hydroxycinnamoyl ester (e.g. chlorogenate) to an acceptor molecule, most commonly to an OH or NH2 group as ester or amide. The hydroxycinnamoyl groups play either a “decorating” role or are building blocks of more complex structures. Proteins catalysing hydroxycinnamoyl transfer have been known for many decades and are nowadays investigated on molecular and structural levels. At least four different protein families give rise to enzymes with hydroxycinnamoyltransferase activity: serine carboxypeptidase-like proteins, tyramine hydroxycinnamoyltransferase-like enzymes, BAHD acyltransferases and GDSL-lipase/esterase-like enzymes. Interestingly, the same or very similar products can be formed by enzymes from different enzyme classes and using differently activated hydroxycinnamoyl units. This review will summarise the current literature data on the features of hydroxycinnamoyltransferases from the four different enzyme groups.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

Abbreviations

HCT:

Hydroxycinnamoyltransferase

HQT:

Hydroxycinnamoyl-CoA:quinate hydroxycinnamoyltransferase

HST:

Hydroxycinnamoyl-CoA:shikimate hydroxycinnamoyltransferase

SCPL:

Serine caryboxypeptidase-like

THT:

Tyramine hydroxycinnamoyltransferase

References

  • Abe I, Morita H (2010) Structure and function of the chalcone synthase superfamily of plant type III polyketide synthases. Nat Prod Rep 27:809–838

    Article  CAS  PubMed  Google Scholar 

  • Alber A, Ehlting J (2012) Cytochrome P450 s in lignin biosynthesis. Adv Bot Res 61:113–143

    Article  CAS  Google Scholar 

  • Back K, Jang SM, Lee BC, Schmidt A, Strack D, Kim KM (2001) Cloning and characterisation of a hydroxycinnamoyl-CoA:tyramine N-(hydroxycinnamoyl)transferase induced in response to UV-C and wounding from Capsicum annuum. Plant Cell Physiol 42:475–481

    Article  CAS  PubMed  Google Scholar 

  • Baumert A, Milkowski C, Schmidt J, Nimtz M, Wray V, Strack D (2005) Formation of a complex pattern of sinapate esters in Brassica napus seeds, catalyzed by enzymes of a serine carboxypeptidase-like acyltransferase family? Phytochemistry 66:1334–1345

    Article  CAS  PubMed  Google Scholar 

  • Berger A, Meinhard J, Petersen M (2006) Rosmarinic acid synthase is a new member of the superfamily of BAHD acyltransferases. Planta 224:1503–1510

    Article  CAS  PubMed  Google Scholar 

  • Bokern M, Strack D (1988) Synthesis of hydroxycinnamic acid esters of betacyanins via 1-O-acylglucosides of hydroxycinnamic acids by protein preparations from cell suspension cultures of Chenopodium rubrum and petals of Lampranthus sociorum. Planta 174:101–105

    Article  CAS  PubMed  Google Scholar 

  • Bokern M, Wray V, Strack D (1991) Accumulation of phenolic acid conjugates and betacyanins, and changes in the activities of enzymes involved in feruloylglucose metabolism in cell-suspension cultures of Chenopodium rubrum L. Planta 184:261–270

    Article  CAS  PubMed  Google Scholar 

  • Bouchereau AJ, Hamelin J, Renard M, Larher F (1992) Structural changes in sinapic acid conjugates during development of rape. Plant Physiol Biochem 30:467–475

    CAS  Google Scholar 

  • Budiman MA, Mao L, Wood TC, Wing RA (2000) A deep-coverage tomato BAC library and prospects toward development of an STC framework for genome sequencing. Genome Res 10:129–136

    CAS  PubMed  PubMed Central  Google Scholar 

  • Burhenne K, Kristensen BK, Rasmussen SK (2003) A new class of N-hydroxycinnamoyltransferases. Purification, cloning, and expression of a barley agmatine coumaroyltransferase (EC 2.3.1.64). J Biol Chem 278:13919–13927

    Article  CAS  PubMed  Google Scholar 

  • Campos L, Lisón P, López-Gresa MP, Rodrigo I, Zacarés L, Conejero V, Bellés JM (2014) Transgenic tomato plants overexpressing tyramine N-hydroxycinnamoyltransferase exhibit elevated hydroxycinnamic acid amide levels and enhanced resistance to Pseudomonas syringae. Mol Plant Microbe Interact 27:1159–1169

    Article  PubMed  CAS  Google Scholar 

  • Chepyshko H, Lai CP, Huang LM, Liu JH, Shaw JF (2012) Multifunctionality and diversity of GDSL esterase/lipase gene family in rice (Oryza sativa L. japonica) genome: new insights from bioinformatics analysis. BMC Genom 13:309

    Article  CAS  Google Scholar 

  • Chong J, Poutaraud A, Hugueney P (2009) Metabolism and roles of stilbenes in plants. Plant Sci 177:143–155

    Article  CAS  Google Scholar 

  • Clauß K, Baumert A, Nimtz M, Milkowski C, Strack D (2008) Role of a GDSL lipase-like protein as sinapine esterase in Brassicaceae. Plant J 53:802–813

    Article  PubMed  CAS  Google Scholar 

  • Clé C, Hill LM, Niggeweg R, Martin CR, Guisez Y, Prinsen E, Jansen MAK (2008) Modulation of chlorogenic acid biosynthesis in Solanum lycopersicum; consequences for phenolic accumulation and UV-tolerance. Phytochemistry 69:2149–2156

    Article  PubMed  CAS  Google Scholar 

  • Comino C, Lanteri S, Portis E, Acquadro A, Romani A, Hehn A, Larbat R, Bourgaud F (2007) Isolation and functional characterization of a cDNA coding a hydroxycinnamoyltransferase involved in phenylpropanoid biosynthesis in Cynara cardunculus L. BMC Plant Biol 7:14

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Comino C, Hehn A, Moglia A, Menin B, Bourgaud F, Lanteri S, Portis E (2009) The isolation and mapping of a novel hydroxycinnamoyltransferase in the globe artichoke chlorogenic acid pathway. BMC Plant Biol 9:30

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Cox RJ, Al-Fahad A (2013) Chemical mechanisms involved during the biosynthesis of tropolones. Curr Opin Chem Biol 17:532–536

    Article  CAS  PubMed  Google Scholar 

  • Cukovic D, Ehlting J, VanZiffle JA, Douglas CJ (2001) Structure and evolution of 4-coumarate:coenzyme A ligase (4CL) gene families. Biol Chem 382:645–654

    CAS  PubMed  Google Scholar 

  • D’Auria JC (2006) Acyltransferases in plants: a good time to be BAHD. Curr Opin Plant Biol 9:331–340

    Article  PubMed  CAS  Google Scholar 

  • Dahlbender B, Strack D (1986) Purification and properties of 1-(hydroxycinnamoyl)-glucose:1-(hydroxycinnamoyl)-glucose hydroxycinnamoyltransferase from radish seedlings. Phytochemistry 25:1043–1046

    Article  CAS  Google Scholar 

  • Dewick PM (2009) Medicinal natural products. A biosynthetic approach, Third edn. Wiley, Chichester

    Book  Google Scholar 

  • Di P, Zhang L, Chen J, Tan H, Xiao Y, Dong X, Zhou X, Chen W (2013) 13C tracer reveals phenolic acids biosynthesis in hairy root cultures of Salvia miltiorrhiza. ACS Chem Biol 8:1537–1548

    Article  CAS  PubMed  Google Scholar 

  • Dudareva N, D’Auria JC, Nam KH, Raguso RA, Pichersky E (1998) Acetyl-CoA:benzylalcohol acetyltransferase—an enzyme involved in floral scent production in Clarkia breweri. Plant J 14:297–304

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  • Facchini PJ, Hagel J, Zulak KG (2002) Hydroxycinnamic acid amide metabolism: physiology and biochemistry. Can J Bot 80:577–589

    Article  CAS  Google Scholar 

  • Falcone Ferreyra ML, Rius SP, Casati P (2012) Flavonoids: biosynthesis, biological functions, and biotechnological applications. Front Plant Physiol 3:222

    CAS  Google Scholar 

  • Farmer MJ, Czernik P, Michael A, Negrel J (1999) Identification and characterization of cDNA clones encoding hydroxycinnamoyl-CoA:tyramine N-hydroxycinnamoyltransferase from tobacco. Eur J Biochem 263:686–694

  • Fellenberg C, Böttcher C, Vogt T (2009) Phenylpropanoid polyamine conjugate biosynthesis in Arabidopsis thaliana flower buds. Phytochemistry 70:1392–1400

    Article  CAS  PubMed  Google Scholar 

  • Fleuriet A, Macheix JJ (1980) Metabolism of hydroxycinnamic derivatives in the tomato ‘Cerise’. Part 1. Glucose derivatives of hydroxycinnamic acids of the tomato: evolution during the life of the fruit and formation in vitro. Phytochemistry 19:1955–1958

    Article  CAS  Google Scholar 

  • Fleuriet A, Macheix JJ, Suen R, Ibrahim RK (1980) Partial purification and some properties of a hydroxycinnamoyl glucosyltransferase from tomato fruits. Z Naturforsch 35C:967–972

    CAS  Google Scholar 

  • Flores-Sanchez IJ, Verpoorte R (2009) Plant polyketide synthases: a fascinating group of enzymes. Plant Physiol Biochem 47:167–174

    Article  CAS  PubMed  Google Scholar 

  • Fraissinet-Tachet L, Baltz R, Chong J, Kauffmann S, Fritig B, Saindrenan P (1998) Two tobacco genes induced by infection, elicitor and salicylic acid encode glucosyltransferases acting on phenylpropanoids and benzoic acid derivatives, including salicylic acid. FEBS Lett 437:319–323

    Article  CAS  PubMed  Google Scholar 

  • Fraser CM, Rider LW, Chapple C (2005) An expression and bioinformatics analysis of the Arabidopsis serine carboxypeptidase-like gene family. Plant Physiol 138:1136–1148

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Fujiwara H, Tanaka Y, Fukui Y, Nakao M, Ashikari T, Kusumi T (1997) Anthocyanin 5-aromatic acyltransferase from Gentiana triflora. Purification, characterization and its role in anthocyanin biosynthesis. Eur J Biochem 249:45–51

    Article  CAS  PubMed  Google Scholar 

  • Fujiwara H, Tanaka Y, Yonekura-Sakakibara K, Fukuchi-Mizutani M, Nakao M, Fukui Y, Yamaguchi M, Ashikari T, Kusumi T (1998a) cDNA cloning, gene expression and subcellular localization of anthocyanin 5-aromatic acyltransferase from Gentiana triflora. Plant J 16:421–431

    Article  CAS  PubMed  Google Scholar 

  • Fujiwara H, Tanaka Y, Fukui Y, Ashikari T, Yamaguchi M, Kusumi T (1998b) Purification and characterization of anthocyanin 3-aromatic acyltransferases from Perilla frutescens. Plant Sci 137:87–94

    Article  CAS  Google Scholar 

  • Garvey GS, McCormick SP, Rayment I (2008) Structural and functional characterization of the TRI101 trichothecene 3-O-acetyltransferase from Fusarium sporotrichioides and Fusarium graminearum: kinetic insights to combating Fusarium head blight. J Biol Chem 283:1660–1669

    Article  CAS  PubMed  Google Scholar 

  • Garvey GS, McCormick SP, Alexander NJ, Rayment I (2009) Structural and functional characterization of TRI3 trichothecene 15-O-acetyltransferase from Fusarium sporotrichioides. Protein Sci 18:747–761

    CAS  PubMed  PubMed Central  Google Scholar 

  • Georgiev MI, Ivanovska N, Alipieva K, Dimitrova P, Verpoorte R (2013) Harpagoside: from Kalahari Desert to pharmacy shelf. Phytochemistry 92:8–15

    Article  CAS  PubMed  Google Scholar 

  • Gläßgen WE, Seitz HU (1992) Acylation of anthocyanins with hydroxycinnamic acids via 1-O-acylglucosides by protein preparations from cell cultures of Daucus carota L. Planta 186:582–585

    Article  Google Scholar 

  • Gou JY, Yu XH, Liu CJ (2009) A hydroxycinnamoyltransferase responsible for synthesizing suberin aromatics in Arabidopsis. Proc Natl Acad Sci USA 106:18855–18860

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Grienenberger E, Besseau S, Geoffroy P, Debayle D, Heintz D, Lapierre C, Pollet B, Heitz T, Legrand M (2009) A BAHD acyltransferase is expressed in the tapetum of Arabidopsis anthers and is involved in the synthesis of hydroxycinnamoyl spermidines. Plant J 58:246–259

    Article  CAS  PubMed  Google Scholar 

  • Grisebach H, Barz W, Hahlbrock K, Kellner S, Patschke L (1966) Recent investigations on the biosynthesis of flavonoids. In: Proceedings of 2nd Meeting Fed European Biochem Soc Vienna vol 3, pp 25–36

  • Hall D, De Luca V (2007) Mesocarp localization of a bi-functional resveratrol/hydroxycinnamic acid glucosyltransferase of Concord grape (Vitis labrusca). Plant J 49:579–591

    Article  CAS  PubMed  Google Scholar 

  • Haslam E (1993) Shikimic acid. Metabolism and metabolites. Wiley, Chichester

    Google Scholar 

  • Hause B, Meyer K, Viitanen PV, Chapple C, Strack D (2002) Immunolocalization of 1-O-sinapoyl-glucose:malate sinapoyltransferase in Arabidopsis thaliana. Planta 215:26–32

    Article  CAS  PubMed  Google Scholar 

  • Hoffmann L, Maury S, Martz F, Geoffroy P, Legrand M (2003) Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism. J Biol Chem 278:95–102

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Hoffmann L, Besseau S, Geoffroy P, Ritzenthaler C, Meyer D, Lapierre C, Pollet B, Legrand M (2005) Acyltransferase-catalysed p-coumarate ester formation is a committed step of lignin biosynthesis. Plant Biosyst 139:50–53

    Article  Google Scholar 

  • Hohlfeld H, Schürmann W, Scheel D, Strack D (1995) Partial purification and characterization of hydroxycinnamoyl-coenzyme A:tyramine hydroxycinnamoyl-transferase from cell suspension cultures of Solanum tuberosum. Plant Physiol 107:545–552

    PubMed  PubMed Central  Google Scholar 

  • Hohlfeld H, Scheel D, Strack D (1996) Purification of hydroxycinnamoyl-CoA:tyramine hydroxycinnamoyltransferase from cell-suspension cultures of Solanum tuberosum L. cv. Datura. Planta 199:166–168

    Article  CAS  Google Scholar 

  • Jang S, Ishihara A, Back K (2004) Production of coumaroylserotonin and feruloylserotonin in transgenic rice expressing pepper hydroxycinnamoyl-coenzyme A:serotonin N-(hydroxycinnamoyl)transferase. Plant Physiol 135:346–356

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Kang K, Jang SM, Kang S, Back K (2005) Enhanced neutraceutical serotonin derivatives of rice seed by hydroxycinnamoyl-CoA:serotonin N-(hydroxycinnamoyl)transferase. Plant Sci 168:783–788

    Article  CAS  Google Scholar 

  • Kang S, Kang K, Chung GC, Choi D, Ishihara A, Lee DS, Back K (2006) Functional analysis of the amine substrate specificity domain of pepper tyramine and serotonin N-hydroxycinnamoyltransferases. Plant Physiol 140:705–715

    Article  CAS  Google Scholar 

  • Kang K, Lee K, Ishihara A, Park S, Kim YS, Back K (2010) Induced synthesis of caffeoylserotonin in pepper fruits upon infection by the anthracnose fungus, Colletotrichum gloeosporioides. Sci Hort 124:290–293

    Article  CAS  Google Scholar 

  • Katsuyama Y, Kita T, Funa N, Horinouchi S (2009) Curcuminoid biosynthesis by two type III polyketide synthases in the herb Curcuma longa. J Biol Chem 284:11160–11170

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Kesy JM, Bandurski RS (1990) Partial purification and characterization of indol-3-ylacetylglucose: myo-inositol indol-3-ylacetyltransferase (indoleacetic acid-inositol synthase). Plant Physiol 94:1598–1604

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Kikuta Y, Ueda H, Takahashi M, Mitsumori T, Yamada G, Sakamori K, Takeda K, Furutani S, Nakayama K, Katsuda Y, Hatanaka A, Matsuda K (2012) Identification and characterization of a GDSL lipase-like protein that catalyzes the ester-forming reaction for pyrethrin biosynthesis in Tanacetum cinerariifolium—a new target for plant protection. Plant J 71:183–193

    Article  CAS  PubMed  Google Scholar 

  • Kojima M, Kondo T (1985) An enzyme in Sweet Potato root which catalyzes the conversion of chlorogenic acid, 3-caffeoylquinic acid, to isochlorogenic acid, 3,5-dicaffeoylquinic acid. Agric Biol Chem 49:2467–2469

    CAS  Google Scholar 

  • Kojima M, Villegas RJA (1984) Detection of the enzyme in sweet potato root which catalyzes trans-esterification between 1-O-p-coumaroyl-d-glucose and d-quinic acid. Agric Biol Chem 48:2397–2399

    CAS  Google Scholar 

  • Kowalczyk S, Jakubowska A, Zielińska E, Bandurski RS (2003) Bifunctional indole-3-acetyl transferase catalyses synthesis and hydrolysis of indole-3-acetyl-myo-inositol in immature endosperm of Zea mays. Physiol Plantarum 119:165–174

    Article  CAS  Google Scholar 

  • Lallemand LA, McCarthy JG, McSweeney S, McCarthy AA (2012a) Purification, crystallization and preliminary X-ray diffraction analysis of a hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyltransferase (HCT) from Coffea canephora involved in chlorogenic acid biosynthesis. Acta Cryst F 68:824–828

    Article  CAS  Google Scholar 

  • Lallemand LA, Zubieta C, Lee SG, Wang Y, Acajjaoui S, Timmins J, McSweeney S, Jez JM, McCarthy JG, McCarthy AA (2012b) A structural basis for the biosynthesis of the major chlorogenic acids found in coffee. Plant Physiol 160:249–260

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Landmann C, Hücherig S, Fink B, Hoffmann T, Dittlein D, Coiner HA, Schwab W (2011) Substrate promiscuity of a rosmarinic acid synthase from lavender (Lavandula angustifolia L.). Planta 234:305–320

    Article  CAS  PubMed  Google Scholar 

  • Lee S, Kaminaga Y, Cooper B, Pichersky E, Dudareva N, Chapple C (2012) Benzoylation and sinapoylation of glucosinolate R-groups in Arabidopsis. Plant J 72:411–422

    Article  CAS  PubMed  Google Scholar 

  • Lehfeldt C, Shirley AM, Meyer K, Ruegger MO, Cusumano JC, Viitanen PV, Strack D, Chapple C (2000) Cloning of the SNG1 gene of Arabidopsis reveals a role for a serine carboxypeptidase-like protein as an acyltransferase in secondary metabolism. Plant Cell 12:1295–1306

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lepelley M, Cheminade G, Tremillon N, Simkin A, Caillet V, McCarthy J (2007) Chlorogenic acid synthesis in coffee: an analysis of CGA content and real-time RT-PCR expression of HCT, HQT, C3H1, and CCoAOMT1 genes during grain development in C. canephora. Plant Sci 172:978–996

    Article  CAS  Google Scholar 

  • Lewis NG, Davin LB (1999) Lignans: biosynthesis and function. Compr Nat Prod Chem 1:639–712

    Article  CAS  Google Scholar 

  • Li AX, Steffens JC (2000) An acyltransferase catalyzing the formation of diacylglucose is a serine carboxypeptidase-like protein. Proc Natl Acad Sci USA 97:6902–6907

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lim EK, Li Y, Parr A, Jackson R, Ashford DA, Bowles DJ (2001) Identification of glucosyltransferase genes involved in sinapate metabolism and lignin synthesis in Arabidopsis. J Biol Chem 276:4344–4349

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  • Lotfy S, Negrel J, Javelle F (1994) Formation of ω-feruloyloxypalmitic acid by an enzyme from wound-healing potato tuber disks. Phytochemistry 35:1419–1424

    Article  CAS  Google Scholar 

  • Lotfy S, Negrel J, Javelle F (1995) Distribution of hydroxycinnamoyl-CoA: ω-hydroxypalmitic acid O-hydroxycinnamoyltransferase in higher plants. Phytochemistry 40:389–391

    Article  CAS  Google Scholar 

  • Lotfy S, Javelle F, Negrel J (1996) Purification and characterization of hydroxycinnamoyl-coenzyme A: ω-hydroxypalmitic acid O-hydroxycinnamoyltransferase from tobacco (Nicotiana tabacum L.) cell-suspension cultures. Planta 199:475–480

    Article  CAS  Google Scholar 

  • Luo J, Nishiyama Y, Fuell C, Taguchi G, Elliott K, Hill L, Tanaka Y, Kitayama M, Yamazaki M, Bailey P, Parr A, Michael AJ, Saito K, Martin C (2007) Convergent evolution in the BAHD family of acyl transferases: identification and characterization of anthocyanin acyl transferases from Arabidopsis thaliana. Plant J 50:678–695

    Article  CAS  PubMed  Google Scholar 

  • Luo J, Fuell C, Parr A, Hill L, Bailey P, Elliott K, Fairhurst SA, Martin C, Michael AJ (2009) A novel polyamine acyltransferase responsible for the accumulation of spermidine conjugates in Arabidopsis seed. Plant Cell 21:318–333

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Ma X, Koepke J, Bayer A, Linhard V, Fritzsch G, Zhang B, Michel H, Stöckigt J (2004) Vinorine synthase from Rauvolfia: the first example of crystallization and preliminary x-ray diffraction analysis of an enzyme of the BAHD superfamily. Biochim Biophys Acta 1701:129–132

    Article  CAS  PubMed  Google Scholar 

  • Ma X, Koepke J, Bayer A, Fritzsch G, Michel H, Stöckigt J (2005a) Crystallization and preliminary X-ray analysis of native and selenomethionyl vinorine synthase from Rauvolfia serpentina. Acta Cryst D 61:694–696

    Article  CAS  Google Scholar 

  • Ma X, Koepke J, Panjikar S, Fritzsch G, Stöckigt J (2005b) Crystal structure of vinorine synthase, the first representative of the BAHD superfamily. J Biol Chem 280:13576–13583

    Article  CAS  PubMed  Google Scholar 

  • Martin-Tanguy J, Cabanne F, Perdrizet E, Martin C (1978) The distribution of hydroxycinnamic acid amides in flowering plants. Phytochemistry 17:1927–1928

    Article  CAS  Google Scholar 

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

    Article  PubMed  CAS  Google Scholar 

  • Milkowski C, Strack D (2004) Serine carboxypeptidase-like acyltransferases. Phytochemistry 65:517–524

    Article  CAS  PubMed  Google Scholar 

  • Milkowski C, Strack D (2010) Sinapate esters in brassicaceous plants: biochemistry, molecular biology, evolution and metabolic engineering. Planta 232:19–35

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  • Milkowski C, Baumert A, Strack D (2000b) Identification of four Arabidopsis genes encoding hydroxycinnamate glucosyltransferases. FEBS Lett 486:183–184

    Article  CAS  PubMed  Google Scholar 

  • Milkowski C, Baumert A, Schmidt D, Nehlin L, Strack D (2004) Molecular regulation of sinapate ester metabolism in Brassica napus: expression of genes, properties of the encoded proteins and correlation of enzyme activities with metabolite accumulation. Plant J 38:80–92

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  • Mittasch J, Mikolajewski S, Breuer F, Strack D, Milkowski C (2010) Genomic microstructure and differential expression of the genes encoding UDP-glucose:sinapate glucosyltransferase (UGT84A9) in oilseed rape (Brassica napus). Theor Appl Genet 120:1485–1500

    Article  CAS  PubMed  Google Scholar 

  • Mock HP, Strack D (1993) Energetics of the uridine 5‘-diphosphoglucose:hydroxycinnamic acid acyl-glucosyltransferase reaction. Phytochemistry 32:575–579

    Article  CAS  Google Scholar 

  • Mock HP, Vogt T, Strack D (1992) Sinapoylglucose:malate sinapoyltransferase activity in Arabidopsis thaliana and Brassica napus. Z Naturforsch 47C:680–682

    Google Scholar 

  • Moglia A, Comino C, Lanteri S, de Vos R, de Waard P, van Beek TA, Goitre L, Retta SF, Beekwilder J (2010) Production of novel antioxidative phenolic amides through heterologous expression of the plant’s chlorogenic acid biosynthesis genes in yeast. Metabol Eng 12:223–232

    Article  CAS  Google Scholar 

  • Moglia A, Lanteri S, Comino C, Hill L, Knevitt D, Cagliero C, Rubiolo P, Bornemann S, Martin C (2014) Dual catalytic activity of hydroxycinnamoyl-coenzyme A quinate transferase from tomato allows it to moonlight in the synthesis of both mono- and dicaffeoylquinic acids. Plant Physiol 166:1777–1787

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Molina I, Li-Beisson Y, Beisson F, Ohlrogge JB, Pollard M (2009) Identification of an Arabidopsis feruloyl-coenzyme A transferase required for suberin synthesis. Plant Physiol 151:1317–1328

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Mugford ST, Osbourn A (2010) Evolution of serine carboxypeptidase-like acyltransferases in the monocots. Plant Sign Behav 5:193–195

    Article  CAS  Google Scholar 

  • Mugford ST, Qi X, Bakht S, Hill L, Wegel E, Hughes RK, Papadopoulou K, Melton R, Philo M, Sainsbury F, Lomonossoff GP, Roy AD, Goss RJM, Osbourn A (2009) A serine carboxypeptidase-like acyltransferase is required for synthesis of antimicrobial compounds and disease resistance in oats. Plant Cell 21:2473–2484

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Muroi A, Ishihara A, Tanaka C, Ishizuka A, Takabayashi J, Miyoshi H, Nishioka T (2009) Accumulation of hydroxycinnamic acid amides induced by pathogen infection and identification of agmatine coumaroyltransferase in Arabidopsis thaliana. Planta 230:517–527

    Article  CAS  PubMed  Google Scholar 

  • Nakane E, Kawakita K, Doke N, Yoshioka H (2003) Elicitation of primary and secondary metabolism during defense in the potato. J Gen Plant Pathol 69:378–384

    Article  CAS  Google Scholar 

  • Nakayamu T (2002) Enzymology of aurone biosynthesis. J Biosci Bioeng 94:487–491

    Article  Google Scholar 

  • Negrel J (1989) The biosynthesis of cinnamoylputrescines in callus-tissue cultures of Nicotiana tabacum. Phytochemistry 28:477–481

    Article  CAS  Google Scholar 

  • Negrel J, Javelle F (1992) Purification and properties of putrescine hydroxycinnamoyl transferase from tobacco (Nicotiana tabacum) cell suspensions. Plant Physiol 98:1264–1269

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Negrel J, Javelle F (1997) Purification, characterization and partial amino acid sequencing of hydroxycinnamoyl-CoA:tyramine N-(hydroxycinnamoyl)transferase from tobacco cell-suspension cultures. Eur J Biochem 247:1127–1135

    Article  CAS  PubMed  Google Scholar 

  • Negrel J, Martin C (1984) The biosynthesis of feruloyltyramine in Nicotiana tabacum. Phytochemistry 23:2797–2801

    Article  CAS  Google Scholar 

  • Negrel J, Lotfy S, Javelle F (1995) Modulation of the activity of two hydroxycinnamoyl transferases in wound-healing potato tuber disks in response to pectinase or abscisic acid. J Plant Physiol 146:318–322

    Article  CAS  Google Scholar 

  • Niggeweg R, Michael AJ, Martin C (2004) Engineering plants with increased levels of the antioxidant chlorogenic acid. Nature Biotechnol 22:746–754

    Article  CAS  Google Scholar 

  • Ogata A, Tsuruga A, Matsuno M, Mizukami H (2004) Elicitor-induced rosmarinic acid biosynthesis in Lithospermum erythrorhizon cell suspension cultures: activities of rosmarinic acid synthase and the final two cytochrome P450-catalyzed hydroxylations. Plant Biotechnol 21:393–396

    Article  CAS  Google Scholar 

  • Paterson AH, Bowers JE, Bruggmann R, Dubchak I, Grimwood J, Gundlach H, Haberer G, Hellsten U, Mitros T, Poliakov A, Schmutz J, Spannagl M, Tang H, Wang X, Wicker T, Bharti AK, Chapman J, Feltus FA, Gowik U, Grigoriev IV, Lyons E, Maher CA, Martis M, Narechania A, Otillar RP, Penning BW, Salamov AA, Wang Y, Zhang L, Carpita NC, Freeling M, Gingle AR, Hash CT, Keller B, Klein P, Kresovich S, McCann MC, Ming R, Peterson DG, Mehboob-ur-Rahman Ware D, Westhoff P, Mayer KF, Messing J, Rokhsar DS (2009) The Sorghum bicolor genome and the diversification of grasses. Nature 457:551–556

    Article  CAS  PubMed  Google Scholar 

  • Petersen M (2013) Rosmarinic acid: new aspects. Phytochem Rev 12:207–227

    Article  CAS  Google Scholar 

  • Petersen M, Simmonds MSJ (2003) Molecules of interest: rosmarinic acid. Phytochemistry 62:121–125

    Article  CAS  PubMed  Google Scholar 

  • Petersen M, Hans J, Matern U (2010) Biosynthesis of phenylpropanoids and related compounds. Annu Plant Rev 40:182–257

    CAS  Google Scholar 

  • Ramirez-Ahumada M, Timmermann BN, Gang DR (2006) Biosynthesis of curcuminoids and gingerols in turmeric (Curcuma longa) and ginger (Zingiber officinale): identification of curcuminoid synthase and hydroxycinnamoyl-CoA thioesterases. Phytochemistry 67:2017–2029

    Article  CAS  Google Scholar 

  • Ruppert M, Woll J, Giritch A, Genady E, Ma X, Stöckigt J (2005) Functional expression of an ajmaline pathway-specific esterase from Rauvolfia in a novel plant–virus expression system. Planta 222:888–898

    Article  CAS  PubMed  Google Scholar 

  • Saito K, Yonekura-Sakakibara K, Nakabayashi R, Higashi Y, Yamazaki M, Tohge T, Fernie AR (2013) The flavonoid biosynthetic pathway in Arabidopsis: structural and genetic diversity. Plant Physiol Biochem 72:21–34

    Article  CAS  PubMed  Google Scholar 

  • Sander M (2010) Molekularbiologische und biochemische Untersuchungen von Hydroxycinnamoyltransferasen aus Coleus blumei und Glechoma hederacea. Dissertation, Philipps-Universität Marburg

  • Sander M, Petersen M (2011) Distinct substrate specificities and unusual substrate flexibilities of two hydroxycinnamoyltransferases, rosmarinic acid synthase and hydroxycinnamoyl-CoA:shikimate hydroxycinnamoyltransferase, from Coleus blumei Benth. Planta 233:1157–1171

    Article  CAS  PubMed  Google Scholar 

  • Saylor MH, Mansell RL (1977) Hydroxycinnamoyl:coenzyme A transferase involved in the biosynthesis of kaempferol-3-(p-coumaroyl triglucoside) in Pisum sativum. Z Naturforsch 32C:764–768

    Google Scholar 

  • Schmidt A, Grimm R, Schmidt J, Scheel D, Strack D, Rosahl S (1999) Cloning and expression of a potato cDNA encoding hydroxycinnamoyl-CoA:tyramine N-(hydroxycinnamoyl)transferase. J Biol Chem 274:4273–4280

    Article  CAS  PubMed  Google Scholar 

  • Schmidt GW, Jirschitzka J, Porta T, Reichelt M, Luck K, Torre JCP, Dolke F, Varesio E, Hopfgartner G, Gershenzon J, D’Auria JC (2015) The last step in cocaine biosynthesis is catalyzed by a BAHD acyltransferase. Plant Physiol 167:89–101

    Article  CAS  PubMed  Google Scholar 

  • Schneider K, Hövel K, Witzel K, Hamberger B, Schomburg D, Kombrink E, Stuible HP (2003) The substrate specificity-determining amino acid code of 4-coumarate:CoA ligase. Proc Natl Acad Sci USA 100:8601–8606

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Serra O, Hohn C, Franke R, Prat S, Molinas M, Figueras M (2010) A feruloyl transferase involved in the biosynthesis of suberin and suberin-associated wax is required for maturation and sealing properties of potato periderm. Plant J 62:277–290

    Article  CAS  PubMed  Google Scholar 

  • Shadle G, Chen F, Reddy MSS, Jackson L, Nakashima J, Dixon RA (2007) Down-regulation of hydroxycinnamoyl-CoA:shikimate hydroxycinnamoyl transferase in transgenic alfalfa affects lignification, development and forage quality. Phytochemistry 68:1521–1529

    Article  CAS  PubMed  Google Scholar 

  • Shi S, Morita H, Wanibuchi K, Mizuuchi Y, Noguchi H, Abe I (2008) Enzymatic synthesis of plant polyketides. Curr Org Synth 5:250–266

    Article  CAS  Google Scholar 

  • Shimizu T, Kojima M (1984) Partial purification and characterization of UDPG:t-cinnamate glucosyltransferase in the root of Sweet Potato, Ipomoea batatas Lam. J Biochem 95:205–212

    CAS  PubMed  Google Scholar 

  • Shirley AM, Chapple C (2003a) An expression and bioinformatics analysis of the Arabidopsis serine carboxypeptidase-like gene family. J Biol Chem 278:19870–19877

    Article  CAS  PubMed  Google Scholar 

  • Shirley AM, Chapple C (2003b) Biochemical characterization of sinapoylglucose:choline sinapoyltransferase, a serine carboxypeptidase-like protein that functions as an acyltransferase in plant secondary metabolism. J Biol Chem 278:19870–19877

    Article  CAS  PubMed  Google Scholar 

  • Shirley AM, McMichael CM, Chapple C (2001) sng2 mutant of Arabidopsis is defective in the gene encoding the serine carboxypeptidase-like protein sinapoylglucose:choline sinapoyltransferase. Plant J 28:83–94

    Article  CAS  PubMed  Google Scholar 

  • Sonnante G, D’Amore R, Blanco E, Pierri CL, De Palma M, Luo J, Tucci M, Martin C (2010) Novel hydroxycinnamoyl-coenzyme A quinate transferase genes from artichoke are involved in the synthesis of chlorogenic acid. Plant Physiol 153:1224–1238

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • St. Pierre B, De Luca V (2000) Evolution of acyltransferase genes: origin and diversification of the BAHD superfamily of acyltransferases involved in secondary metabolism. Rec Adv Phytochem 34:285–316

    CAS  Google Scholar 

  • St. Pierre B, Laflamme P, Alarco AM, Luca V (1998) The terminal O-acetyltransferase involved in vindoline biosynthesis defines a new class of proteins responsible for coenzyme A dependent acyl transfer. Plant J 14:703–713

    Article  CAS  PubMed  Google Scholar 

  • Starzyńska E, Kowalczyk S (2012) Novel 1-O-indole-3-acetyl-β-d-glucose-dependent acyltransferase transferring indoleacetyl moiety to some mono- di- and oligosaccharides. Acta Physiol Plantarum 34:53–63

    Article  CAS  Google Scholar 

  • Steffens JC (2000) Acyltransferases in protease’s clothing. Plant Cell 12:1253–1255

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Stehle F, Brandt W, Milkowski C, Strack D (2006) Structure determinants and substrate recognition of serine carboxypeptidase-like acyltransferases from plant secondary metabolism. FEBS Lett 580:6366–6374

    Article  CAS  PubMed  Google Scholar 

  • Stehle F, Brandt W, Schmidt J, Milkowski C, Strack D (2008a) Activities of Arabidopsis sinapoylglucose:malate sinapoyltransferase shed light on functional diversification of serine carboxypeptidase-like acyltransferases. Phytochemistry 69:1826–1831

    Article  CAS  PubMed  Google Scholar 

  • Stehle F, Stubbs MT, Strack D, Milkowski C (2008b) Heterologous expression of a serine carboxypeptidase-like acyltransferase and characterization of the kinetic mechanism. FEBS J 275:775–787

    Article  CAS  PubMed  Google Scholar 

  • Stehle F, Götsch F, Wray V, Schmidt J, Strack D, Brandt W (2013) Snap-shot of serine carboxypeptidase-like acyltransferase evolution: the loss of conserved disulphide bridge is responsible for the completion of neo-functionalization. J Phylogen Evolution Biol 1:115

    Google Scholar 

  • Strack D (1980) Enzymatic synthesis of 1-sinapoylglucose from free sinapic acid and UDP-glucose by a cell free system from Raphanus sativus seedlings. Z Naturforsch 35C:204–208

    CAS  Google Scholar 

  • Strack D, Gross W (1990) Properties and activity changes of chlorogenic acid:glucaric acid caffeoyltransferase from tomato (Lycopersicon esculentum). Plant Physiol 92:41–47

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Strack D, Knogge W, Dahlbender B (1983) Enzymatic synthesis of sinapine from 1-O-β-d-glucose and choline by a cell-free system from developing seeds of red radish (Raphanus sativus L. var. sativus). Z Naturforsch 38C:21–27

    CAS  Google Scholar 

  • Strack D, Ruhoff R, Gräwe W (1986) Hydroxycinnamoyl-coenzyme-A:tartronate hydroxycinnamoyltransferase in protein preparations from mung bean. Phytochemistry 25:833–837

    Article  CAS  Google Scholar 

  • Strack D, Heilemann J, Boehnert B, Grotjahn L, Wray V (1987a) Accumulation and enzymatic synthesis of 2-O-acetyl-3-O-(p-coumaroyl)-meso-tartaric acid in spinach cotyledons. Phytochemistry 26:107–111

    Article  Google Scholar 

  • Strack D, Keller H, Weissenböck G (1987b) Enzymatic synthesis of hydroxycinnamic acid esters of sugar acids and hydroaromatic acids by protein preparations from rye (Secale cereale) primary leaves. J Plant Physiol 131:61–73

    Article  CAS  Google Scholar 

  • Strack D, Leicht P, Bokern M, Wray V, Grotjahn L (1987c) Hydroxycinnamic acid esters of isocitric acid: accumulation and enzymatic synthesis in Amaranthus cruentus. Phytochemistry 26:2919–2922

    Article  CAS  Google Scholar 

  • Strack D, Gross W, Heilemann J, Keller H, Ohm S (1988) Enzymic synthesis of hydroxycinnamic acid esters of glucaric acid and hydroaromatic acids from the respective 1-O-hydroxycinnamoylglucoside and hydroxycinnamoyl-coenzyme A thioester as acyldonors with a protein preparation from Cestrum elegans leaves. Z Naturforsch 43C:32–36

    Google Scholar 

  • Stuible HP, Kombrink E (2001) Identification of the substrate specificity-conferring amino acid residues of 4-coumarate:coenzyme A ligase allows the rational design of mutant enzymes with new catalytic properties. J Biol Chem 276:26893–26897

    Article  CAS  PubMed  Google Scholar 

  • Sullivan ML (2009) A novel red clover hydroxycinnamoyl transferase has enzymatic activities consistent with a role in phaselic acid biosynthesis. Plant Physiol 150:1866–1879

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Sullivan ML (2014) Perennial peanut (Arachis glabrata Benth.) leaves contain hydroxycinnamoyl-CoA:tartaric acid hydroxycinnamoyl transferase activity and accumulate hydroxycinnamoyl-tartaric acid esters. Planta 239:1091–1100

    Article  CAS  PubMed  Google Scholar 

  • Sullivan ML, Zarnowski R (2011) Red clover HCT2, a hydroxycinnamoyl-coenzyme A:malate hydroxycinnamoyl transferase, plays a crucial role in biosynthesis of phaselic acid and other hydroxycinnamoyl-malate esters in vivo. Plant Physiol 155:1060–1067

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Suzuki S, Umezawa T (2007) Biosynthesis of lignans and norlignans. J Wood Sci 4:273–284

    Article  CAS  Google Scholar 

  • Tamura K, Stecher G, Peterson D, Filipski A, Kumar S (2013) MEGA6: molecular evolutionary genetics analysis version 6.0. Mol Biol Evol 30:2725–2729

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Teutschbein J, Gross W, Nimtz M, Milkowski C, Hause B, Strack D (2010) Identification and localization of a lipase-like acyltransferase in phenylpropanoid metabolism of tomato (Solanum lycopersicum). J Biol Chem 285:38374–38381

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Tian L, Pang Y, Dixon RA (2008) Biosynthesis and genetic engineering of proanthocyanidins and (iso)flavonoids. Phytochem Rev 7:445–465

    Article  CAS  Google Scholar 

  • Tkotz N, Strack D (1980) Enzymatic synthesis of sinapoyl-L-malate from 1-sinapoylglucose and L-malate by a protein preparation from Raphanus sativus cotelydons. Z Naturforsch 35C:835–837

    CAS  Google Scholar 

  • Umezawa T (2010) The cinnamate/monolignol pathway. Phytochem Rev 9:1–17

    Article  CAS  Google Scholar 

  • Unno H, Ichimaida F, Suzuki H, Takahashi S, Tanaka Y, Saito A, Nishino T, Kusunoki M, Nakayama T (2007) Structural and mutational studies of anthocyanin malonyltransferases establish the features of BAHD enzyme catalysis. J Biol Chem 282:15812–15822

    Article  CAS  PubMed  Google Scholar 

  • Vanholme R, Demedts B, Morreel K, Ralph J, Boerjan W (2010) Lignin biosynthesis and structure. Plant Physiol 153:895–905

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Vanholme R, Cesarino I, Rataj K, Xiao Y, Sundin L, Goeminne G, Kim H, Cross J, Morreel K, Araujo P, Welsh L, Haustraete J, McClellan C, Vanholme B, Ralph J, Simpson GG, Halpin C, Boerjan W (2013) Caffeoyl shikimate esterase (CSE) is an enzyme in the lignin biosynthetic pathway in Arabidopsis. Science 341:1103–1106

    Article  CAS  PubMed  Google Scholar 

  • Villegas RJA, Kojima M (1985) Sweet potato root enzyme which catalyzes the formation of chlorogenic acid from 1-O-caffeoyl-d-glucose and D-quinic acid. Agric Biol Chem 49:263–265

    CAS  Google Scholar 

  • Villegas RJA, Kojima M (1986) Purification and characterization of hydroxycinnamoyl d-glucose quinate hydroxycinnamoyl transferase in the root of Sweet Potato, Ipomoea batatas Lam. J Biol Chem 261:8729–8733

    CAS  PubMed  Google Scholar 

  • von Roepenack-Lahaye E, Newman MA, Schornack S, Hammond-Kosack KE, Lahaye T, Jones JDG, Daniels MJ, Dow JM (2003) p-Coumaroylnoradrenaline, a novel plant metabolite implicated in tomato defense against pathogens. J Biol Chem 278:43373–43383

    Article  CAS  Google Scholar 

  • Wagner A, Ralph J, Akiyama T, Flint H, Phillips L, Torr K, Nanayakkara B, Te Kiri L (2007) Exploring lignification in conifers by silencing hydroxycinnamoyl-CoA:shikimate hydroxycinnamoyltransferase in Pinus radiata. Proc Natl Acad Sci USA 104:11856–11861

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Wajant H, Mundry KW, Pfizenmaier K (1994) Molecular cloning of hydroxynitrile lyase from Sorghum bicolor (L.). Homologies to serine carboxypeptidases. Plant Mol Biol 26:735–746

    Article  CAS  PubMed  Google Scholar 

  • Wakimoto T, Morita H, Abe I (2012) Engineering of plant type III polyketide synthases. Meth Enzymol 515:337–358

    Article  CAS  PubMed  Google Scholar 

  • Walker AM, Hayes RP, Youn B, Vermerris W, Sattler SE, Kang CH (2013) Elucidation of the structure and reaction mechanism of Sorghum hydroxycinnamoyltransferase and its structural relationship to other coenzyme A-dependent transferases and synthase. Plant Physiol 162:640–651

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Walton E, Butt VS (1970) The activation of cinnamate by an enzyme from leaves of Spinach Beet (Beta vulgaris L. ssp. vulgaris). J Exptl Bot 21:887–891

    Article  CAS  Google Scholar 

  • Weier D, Mittasch J, Strack D, Milkowski C (2008) The genes BnSCT1 and BnSCT2 from Brassica napus encoding the Wnal enzyme of sinapine biosynthesis: molecular characterization and suppression. Planta 227:375–385

    Article  CAS  PubMed  Google Scholar 

  • Weitzel C, Petersen M (2011) Cloning and characterisation of rosmarinic acid synthase from Melissa officinalis L. Phytochemistry 72:572–578

    Article  CAS  PubMed  Google Scholar 

  • Weng JK, Noel JP (2012) Structure-function analyses of plant type III polyketide synthases. Meth Enzymol 515:317–335

    Article  CAS  PubMed  Google Scholar 

  • Yabuya T, Yamaguchi M, Fukui Y, Katoh K, Imayama T, Ino I (2001) Characterization of anthocyanin p-coumaroyltransferase in flowers of Iris ensata. Plant Sci 160:499–503

    Article  CAS  PubMed  Google Scholar 

  • Yang Q, Reinhard K, Schiltz E, Matern U (1997) Characterization and heterologous expression of hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/benzoyltransferase from elicited cell cultures of carnation, Dianthus caryophyllus L. Plant Mol Biol 35:777–789

    Article  CAS  PubMed  Google Scholar 

  • Yang Q, Grimmig B, Matern U (1998) Anthranilate N-hydroxycinnamoyl/benzoyltransferase gene from carnation: rapid elicitation of transcription and promotor analysis. Plant Mol Biol 38:1201–1214

    Article  CAS  PubMed  Google Scholar 

  • Yang Q, Trinh HX, Imai S, Ishihara A, Zhang L, Nakayashiki H, Tosa Y, Mayama S (2004) Analysis of the involvement of hydroxyanthranilate hydroxycinnamoyltransferase and caffeoyl-CoA 3-O-methyltransferase in phytoalexin biosynthesis in oat. Mol Plant Microbe Interact 17:81–89

    Article  CAS  PubMed  Google Scholar 

  • Yonekura-Sakakibara K, Tanaka Y, Fukuchi-Mizutani M, Fujiwara H, Fukui Y, Ashikari T, Murakami Y, Yamaguchi M, Kusumi T (2000) Molecular and biochemical characterization of a novel hydroxycinnamoyl CoA:anthocyanin 3-O-glucoside-6″-O-acyltransferase from Perilla frutescens. Plant Cell Physiol 41:495–502

    Article  CAS  PubMed  Google Scholar 

  • Yoshihara N, Imayama T, Matsuo Y, Fukuchi-Mizutani M, Tanaka Y, Ino I, Yabuya T (2006) Characterization of cDNA clones encoding anthocyanin 3-p-coumaroyltransferase from Iris hollandica. Plant Sci 171:632–639

    Article  CAS  Google Scholar 

  • Young MR, Towers GHN, Neish AC (1966) Taxonomic distribution of ammonia-lyases for l-phenylalanine and l-tyrosine in relation to lignification. Can J Bot 44:341–349

    Article  CAS  Google Scholar 

  • Yu M, Facchini PJ (1999) Purification, characterization, and immunolocalization of hydroxycinnamoyl-CoA: tyramine N-(hydroxycinnamoyl)transferase from opium poppy. Planta 209:33–44

    Article  CAS  PubMed  Google Scholar 

  • Yu XH, Gou JY, Liu CJ (2009) BAHD superfamily of acyl-CoA dependent acyltransferases in Populus and Arabidopsis: bioinformatics and gene expression. Plant Mol Biol 70:421–442

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut für Pharmazeutische Biologie und Biotechnologie, Philipps-Universität Marburg, Deutschhausstr. 17A, 35037, Marburg, Germany

    Maike Petersen

Authors
  1. Maike Petersen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Maike Petersen.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Petersen, M. Hydroxycinnamoyltransferases in plant metabolism. Phytochem Rev 15, 699–727 (2016). https://doi.org/10.1007/s11101-015-9417-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11101-015-9417-1

Keywords

Search

Navigation