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HORT640 - Metabolic Plant Physiology
References, sinapoyl
Abdulrazzak N, Pollet B, Ehlting J, Larsen K, Asnaghi C, Ronseau S, Proux C, Erhardt M, Seltzer V, Renou JP, Ullmann P, Pauly M, Lapierre C, Werck-Reichhart D. A coumaroyl-ester-3-hydroxylase insertion mutant reveals the existence of nonredundant meta-hydroxylation pathways and essential roles for phenolic precursors in cell expansion and plant growth. Plant Physiol. 140: 30-48 (2006).
Bennett RN, Wenke T, Freudenberg B, Mellon FA, Ludwig-Muller J. The tu8 mutation of Arabidopsis thaliana encoding a heterochromatin protein 1 homolog causes defects in the induction of secondary metabolite biosynthesis. Plant Biol. (Stuttg.) 7: 348-357 (2005).
Bharti AK, Khurana JP. Mutants of Arabidopsis as tools to understand the regulation of phenylpropanoid pathway and UVB protection mechanisms. Photochem. Photobiol. 65: 765-776 (1997).
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).
Chapple CC, Vogt T, Ellis BE, Somerville CR. An Arabidopsis mutant defective in the general phenylpropanoid pathway. Plant Cell 4: 1413-1424 (1992).
Chen M, McClure JW. Altered lignin composition in phenylalanine ammonia-lyase-inhibited radish seedlings: implications for seed-derived sinapoyl esters as lignin precursors. Phytochemistry 53: 365-370 (2000).
Clauss K, Baumert A, Nimtz M, Milkowski C, Strack D. Role of a GDSL lipase-like protein as sinapine esterase in Brassicaceae. Plant J. 53: 802-813 (2008).
Do CT, Pollet B, Thevenin J, Sibout R, Denoue D, Barriere Y, Lapierre C, Jouanin L. Both caffeoyl coenzyme A 3-O-methyltransferase 1 and caffeic acid O-methyltransferase 1 are involved in redundant functions for lignin, flavonoids and sinapoyl malate biosynthesis in Arabidopsis. Planta 226: 1117-1129 (2007).
Fellenberg C, Milkowski C, Hause B, Lange PR, Böttcher CT, Schmidt J, Vogt T. Tapetum specific location of a cation-dependent O-methyltransferase in Arabidopsis thaliana. Plant J. 56: 132-145 (2008).
Ferrer JL, Zubieta C, Dixon RA, Noel JP. Crystal structures of alfalfa caffeoyl coenzyme A 3-O-methyltransferase. Plant Physiol. 137: 1009-1017 (2005).
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).
Fraser CM, Rider LW, Chapple C. An expression and bioinformatics analysis of the Arabidopsis serine carboxypeptidase-like gene family. Plant Physiol. 138: 1136-1148 (2005).
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).
Glassgen WE, Rose A, Madlung J, Koch W, Gleitz J, Seitz HU. Regulation of enzymes involved in anthocyanin biosynthesis in carrot cell cultures in response to treatment with ultraviolet light and fungal elicitors. Planta 204: 490-498 (1998).
Goffner D, Campbell MM, Campargue C, Clastre M, Borderies G, Boudet A, Boudet AM. Purification and characterization of cinnamoyl-coenzyme A:NADP oxidoreductase in Eucalyptus gunnii. Plant Physiol. 106: 625-632 (1994).
Gormann R, Kaloga M, Ferreira D, Marais JP, Kolodziej H. Newbouldiosides A-C, phenylethanoid glycosides from the stem bark of Newbouldia laevis. Phytochemistry 67: 805-811 (2006).
Goujon T, Sibout R, Pollet B, Maba B, Nussaume L, Bechtold N, Lu F, Ralph J, Mila I, Barriere Y, Lapierre C, Jouanin L. A new Arabidopsis thaliana mutant deficient in the expression of O-methyltransferase impacts lignins and sinapoyl esters. Plant Mol. Biol. 51: 973-989 (2003).
Grienenberger E, Besseau S, Geoffroy P, Debayle D, Heintz D, Lapierre C, Pollet B, Heitz T, Legrand M. A BAHD acyltransferase is expressed in tapetum of Arabidopsis anthers and is involved in the synthesis of hydroxycinnamoyl spermidines. Plant J. 58: 246-259 (2009).
Hause B, Meyer K, Viitanen PV, Chapple C, Strack D. Immunolocalization of 1-O-sinapoylglucose:malate sinapoyltransferase in Arabidopsis thaliana. Planta 215: 26-32 (2002).
Hemm MR, Herrmann KM, Chapple C. AtMYB4: a transcription factor general in the battle against UV. Trends Plant Sci. 6: 135-136 (2001).
Hemm MR, Ruegger MO, Chapple C. The Arabidopsis ref2 mutant is defective in the gene encoding CYP83A1 and shows both phenylpropanoid and glucosinolate phenotypes. Plant Cell 15: 179-194 (2003).
Huang J, Rozwadowski K, Bhinu VS, Schafer U, Hannoufa A. Manipulation of sinapine, choline and betaine accumulation in Arabidopsis seed: towards improving the nutritional value of the meal and enhancing the seedling performance under environmental stresses in oilseed crops. Plant Physiol. Biochem. 46: 647-654 (2008).
Kristensen C, Morant M, Olsen CE, Ekstrom CT, Galbraith DW, Moller BL, Bak S. Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome. Proc. Natl. Acad. Sci. U.S.A. 102: 1779-1784 (2005).
Lanot A, Hodge D, Jackson RG, George GL, Elias L, Lim EK, Vaistij FE, Bowles DJ. The glucosyltransferase UGT72E2 is responsible for monolignol 4-O-glucoside production in Arabidopsis thaliana. Plant J. 48: 286-295 (2006).
Lanot A, Hodge D, Lim EK, Vaistij FE, Bowles DJ. Redirection of flux through the phenylpropanoid pathway by increased glucosylation of soluble intermediates. Planta 228: 609-616 (2008).
Lehfeldt C, Shirley AM, Meyer K, Ruegger MO, Cusumano JC, Viitanen PV, Strack D, Chapple C. 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 (2000).
Lim EK, Li Y, Parr A, Jackson R, Ashford DA, Bowles DJ. Identification of glucosyltransferase genes involved in sinapate metabolism and lignin synthesis in Arabidopsis. J. Biol. Chem. 276: 4344-4349 (2001).
Lorenzen M, Racicot V, Strack D, Chapple C. Sinapic acid ester metabolism in wild type and a sinapoylglucose-accumulating mutant of Arabidopsis. Plant Physiol. 112: 1625-1630 (1996).
Louis V, Negrel J. Tyramine hydroxycinnamoyl transferase in the roots of wheat and barley seedlings. Phytochemistry 30: 2519-2522 (1991).
Lozovaya V, Ulanov A, Lygin A, Duncan D, Widholm J. Biochemical features of maize tissues with different capacities to regenerate plants. Planta 224: 1385-1399 (2006).
Luderitz T, Grisebach H. Enzymic synthesis of lignin precursors. Comparison of cinnamoyl-CoA reductase and cinnamyl alcohol:NADP+ dehydrogenase from spruce (Picea abies L.) and soybean (Glycine max L.). Eur. J. Biochem. 119: 115-124 (1981).
Luo J, Fuell C, Parr A, Hill L, Bailey P, Elliott K, Fairhurst SA, Martin C, Michael AJ. A novel polyamine acyltransferase responsible for the accumulation of spermidine conjugates in Arabidopsis seed. Plant Cell 21: 318-333 (2009).
Ma QH, Tian B. Biochemical characterization of a cinnamoyl-CoA reductase from wheat. Biol. Chem. 386: 553-560 (2005).
Mattana M, Biazzi E, Consonni R, Locatelli F, Vannini C, Provera S, Coraggio I. Overexpression of Osmyb4 enhances compatible solute accumulation and increases stress tolerance of Arabidopsis thaliana. Physiol. Plant. 125: 212-223 (2005).
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).
Milkowski C, Baumert A, Schmidt D, Nehlin L, Strack D. 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 (2004).
Milkowski C, Baumert A, Strack D. Cloning and heterologous expression of a rape cDNA encoding UDP-glucose:sinapate glucosyltransferase. Planta 211: 883-886 (2000).
Negrel J, Paynoy M, Javelle F. Purification and properties of putrescine hydroxycinnamoyl transferase from tobacco (Nicotiana tabacum) cell suspensions. Plant Physiol. 98: 1264-1269 (1992).
Ruegger M, Meyer K, Cusumano JC, Chapple C. Regulation of ferulate-5-hydroxylase expression in Arabidopsis in the context of sinapate ester biosynthesis. Plant Physiol. 119: 101-110 (1999).
Schmidt A, Grimm R, Schmidt J, Scheel D, Strack D, Rosahl S. Cloning and expression of a potato cDNA encoding hydroxycinnamoyl-CoA:tyramine N-(hydroxycinnamoyl)transferase. J. Biol. Chem. 274: 4273-4280 (1999).
Shirley AM, Chapple C. 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 (2003).
Shirley AM, McMichael CM, Chapple C. The sng2 mutant of Arabidopsis is defective in the gene encoding the serine carboxypeptidase-like protein sinapoylglucose:choline sinapoyltransferase. Plant J. 28: 83-94 (2001).
Stehle F, Brandt W, Milkowski C, Strack D. Structure determinants and substrate recognition of serine carboxypeptidase-like acyltransferases from plant secondary metabolism. FEBS Lett. 580: 6366-6374 (2006).
Stehle F, Brandt W, Schmidt J, Milkowski C, Strack D. Activities of Arabidopsis sinapoylglucose:malate sinapoyltransferase shed light on functional diversification of serine carboxypeptidase-like acyltransferases. Phytochemistry 69: 1826-1831 (2008).
Tatsuzawa F, Saito N, Toki K, Shinoda K, Shigihara A, Honda T. Triacylated cyanidin 3-(3X-glucosylsambubioside)-5-glucosides from the flowers of Malcolmia maritima. Phytochemistry 69: 1029-1036 (2008).
Wybraniec S, Nowak-Wydra B, Mitka K, Kowalski P, Mizrahi Y. Minor betalains in fruits of Hylocereus species. Phytochemistry 68: 251-259 (2007).
Yamauchi K, Yasuda S, Hamada K, Tsutsumi Y, Fukushima K. Multiform biosynthetic pathway of syringyl lignin in angiosperms. Planta 216: 496-501 (2003).
Number of references = 47
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