Related arabidopsis serine carboxypeptidase-like sinapoylglucose acyltransferases display distinct but overlapping substrate specificities

Plant Physiology

Volumn 144, Issue 4, 2007, Pages 1986-1999

  Fraser, Christopher M ^a   Thompson, Michael G ^a,c   Shirley, Amber M ^a,d   Ralph, John ^b   Schoenherr, Jessica A ^a   Sinlapadech, Taksina ^a   Hall, Mark C ^a   Chapple, Clint ^a  

^a PURDUE UNIVERSITY   (United States)

^b U S DAIRY FORAGE RESEARCH CENTER   (United States)

^c PURDUE UNIVERSITY   (United States)

^d BASF CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; GENE ENCODING; METABOLISM; PLANTS (BOTANY);

ARABIDOPSIS (ARABIDOPSIS THALIANA); SEQUENCE ANALYSIS; SERINE CARBOXYPEPTIDASE-LIKE (SCPL);

ENZYMES;

ARABIDOPSIS; ARABIDOPSIS THALIANA; MAGNOLIOPHYTA;

EID: 34547877240     PISSN: 00320889     EISSN: 15322548     Source Type: Journal    
DOI: 10.1104/pp.107.098970     Document Type: Article

References (60)

1. 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
2. Bloor SJ, Abrahams S (2002) The structure of the major anthocyanin in Arabidopsis thaliana. Phytochemistry 59: 343-346
3. Bowles D, Isayenkova J, Lim EK, Poppenberger B (2005) Glycosyltransferases: managers of small molecules. Curr Opin Plant Biol 8: 254-263
4. Brouillard R (1981) Origin of the exceptional colour stability of the Zebrina anthocyanin. Phytochemistry 20: 143-145
5. Brouillard R (1983) The in vivo expression of anthocyanin colour in plants. Phytochemistry 22: 1311-1323
6. Clough JS, Bent AF (1998) Floral dip: a simplified method for Agrobacterium-mediated transformation of Arabidopsis thaliana. Plant J 16: 735-743
7. Croteau R, Hooper CL (1978) Metabolism of monoterpenes: acetylation of (-)-menthol by a soluble enzyme preparation from peppermint (Mentha piperita) leaves. Plant Physiol 61: 737-742
8. Dahlbender B, Strack D (1984) Enzymatic synthesis of 1,2-di-dinapoylglucose from 1-sinapoylglucose by a protein preparation from cotyledons of Raphanus sativus grown in the dark. J Plant Physiol 116: 375-379
9. Dahlbender B, Strack D (1986) Purification and properties of 1-(hydroxycinnamoyl)-glucose: 1-(hydroxycinnamoyl)-glucose hydroxycinnamoyl- transferase from radish seedlings. Phytochemistry 25: 1043-1046
10. Dudareva N, Dauria 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
11. 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
12. Frey M, Chomet P, Glawischnig E, Stettner C, Grun S, Winklmair A, Eisenreich W, Bacher A, Meeley RB, Briggs SP, et al (1997) Analysis of a chemical plant defense mechanism in grasses. Science 277: 696-699
13. Fröhlich B, Niemetz R, Gross GG (2002) Gallotannin biosynthesis: two new galloyltransferases from Rhus typhina leaves preferentially acylating hexa- and heptagalloylglucoses. Planta 216: 168-172
14. Fujiwara H, Tanaka Y, Yonekura-Sakakibara K, Fukuchi-Mizutani M, Nakao M, Fukui Y, Yamaguchi M, Ashikari T, Kusumi T (1998) cDNA cloning, gene expression and subcellular localizationof anthocyanin 5-aromatic acyltransferase from Gentiana triflora. Plant J 16: 421-431
15. 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
16. Hamberger B, Hahlbrock K (2004) The 4-coumarate:CoA ligase gene family in Arabidopsis thaliana comprises one rare, sinapate-activating and three commonly occurring isoenzymes. Proc Natl Acad Sci USA 101: 2209-2214
17. Harborne JB, Mayer AM, Bar-Nun N (1983) Identification of the major anthocyanin of carrot cells in tissue culture as cyanidin 3-(sinapoylxylosylglucosylgalactoside). Z Naturforsch 38c: 1055-1056
18. Honda T, Tatsuzawa F, Kobayashi N, Kasai H, Nagumo S, Shigihara A, Saito N (2005) Acylated anthocyanins from the violet-blue flowers of Orychophragonus violaceus. Phytochemistry 66: 1844-1851
19. Hopp W, Seitz HU (1987) The uptake of acylated anthocyanin into isolated vacuoles from a cell suspension culture of Daucus carota. Planta 170: 74-85
20. Hrazdina G, Iredala H, Mattick LR (1977) Anthocyanin composition of Brassica oleracea cv. Red Danish. Phytochemistry 16: 297-299
21. Jones P, Messner B, Nakajima J, Schaffner AR, Saito K (2003) UGT73C6 and UGT78D1, glycosyltransferases involved in flavonol glycoside biosynthesis in Arabidopsis thaliana. J Biol Chem 278: 43910-43918
22. 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
23. Kliebenstein DJ, Kroymann J, Mitchell-Olds T (2005) The glucosinolatemyrosinase system in an ecological and evolutionary context. Curr Opin Plant Biol 8: 264-271
24. Kuć J (1995) Phytoalexins, stress metabolism, and disease resistance in plants. Annu Rev Phytopathol 33: 275-297
25. 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
26. Lenz R, Zenk MH (1995) Acetyl coenzyme A:salaturidinol-7-O- acetyltransferase from Papaver somniferum plant cell cultures: the enzyme catalyzing the formation of thebaine in morphine biosynthesis. J Biol Chem 270: 31091-31096
27. Li AX, Eannetta N, Ghangas GS, Steffens JC (1999) Glucose polyester biosynthesis: purification and characterization of a glucose acyltransferase. Plant Physiol 121: 453-460
28. 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
29. Li J, Ou-Lee TM, Raba R, Amundson R, Last RL (1993) Arabidopsis flavonoid mutants are hypersensitive to UV-B irradiation. Plant Cell 5: 171-179
30. 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
31. Luo J, Nishiyama Y, Fuell C, Taguchi G, Elliott K, Hill L, Tanaka Y, Kitayama M, Yamazaki M, Bailey P, et al (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
32. Matern U, Reichenbach C, Heller W (1986) Efficient uptake of flavonoids into parsley (Petroselinum hortense) vacuoles requires acylated glycosides. Planta 167: 183-189
33. 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
34. Mock HP, Strack D (1993) Energetics of the uridine 5prime;-diphosphoglucose: hydroxycinnamic acid acyl-glucosyltransferase reaction. Phytochemistry 32: 575-579
35. Murashige T, Skoog F (1962) A revised medium for rapid growth and bioassays with tobacco tissue culture. Physiol Plant 15: 473-497
36. Nakayama T, Suzuki H, Nishino T (2003) Anthocyanin acyltranferases: specificities, mechanism, phylogenetics, and applications. J Mol Catal B Enzym 23: 117-132
37. Poppenberger B, Berthiller F, Lucyshyn D, Sieberer T, Schuhmacher R, Krska R, Kuchler K, Glossl J, Luschnig C, Adam G (2003) Detoxification of the Fusarium mycotoxin deoxynivalenol by a UDP-glucosyltransferase from Arabidopsis thaliana. J Biol Chem 278: 47905-47914
38. Rabot S, Peerless ACJ, Robins RJ (1995) Tigloyl-CoA-pseudotropine acyl transferase - an enzyme of tropane alkaloid biosynthesis. Phytochemistry 39: 315-322
39. Saito N, Tatsuzawa F, Hongo A, Khin WW, Yokoi M, Shigihara A, Honda T (1996) Acylated pelargonidin 3-sambubioside-5-glucoside in Matthiola incana. Phytochemistry 41: 1613-1620
40. Saito N, Tatsuzawa F, Nishiyama A, Yokoi M, Shigihara A, Honda T (1995) Acylated cyanidin 3-sambubrioside-5-glucoside in Matthiola incana. Phytochemistry 38: 1027-1032
41. Shirley AM, McMichael CM, Chapple C (2001) The sng2 mutant of Arabidopsis is defective in the gene encoding the serine carboxypeptidase- like protein sinapoylglucose:choline sinapoyltransferase. Plant J 28: 83-94
42. Sinlapadech T, Stout J, Ruegger MO, Deak M, Chapple C (2007) The hyperfluorescent trichome phenotype of the brt1 mutant of Arabidopsis is the result of a defect in a gene encoding a sinapic acid: UDPG glucosyltransferase. Plant J 49: 655-668
43. St Pierre B, De Luca V (2000) Evolution of Acyltransferase genes: origin and diversification of the BAHD superfamily of acyltransferases involved in secondary metabolism. In JT Romeo, R Ibrahim, L Varin, V De Luca, eds, Recent Advances in Phytochemistry, Volume 34: Evolution of Metabolic Pathways. Pergamon, Oxford, pp 285-315
44. Strack D, Dahlbender B, Grotjahn L, Wray V (1984) 1,2-Disinapoylglucose accumulated in cotyledons of dark-grown Raphanus sativus seedlings. Phytochemistry 23: 657-659
45. Suzuki H, Murakoshi I, Saito K (1994) A novel O-tigloyltransferase for alkaloid biosynthesis in plants: purification, characterization and distribution in Lupinus plants. J Biol Chem 269: 15853-15860
46. Takeda K, Fischer D, Grisebach H (1988) Anthocyanin composition of Sinapis alba, light induction of enzymes and biosynthesis. Phytochemistry 27: 1351-1353
47. Tatsuzawa F, Saito N, Seki H, Yokoi M, Yukawa T, Shinoda K, Honda T (2004) Acylated anthocyanins in the flowers of Vanda (Orchidaceae). Biochem Syst Ecol 32: 651-664
48. Taylor LP, Grotewold E (2005) Flavonoids as developmental regulators. Curr Opin Plant Biol 8: 317-323
49. Tohge T, Nishiyama Y, Hirai MY, Yano M, Nakajima J, Awazuhara M, Inoue E, Takahashi H, Goodenowe DB, Kitayama M, et al (2005) Functional genomics by integrated analysis of metabolome and transcriptome of Arabidopsis plants over-expressing an MYB transcription factor. Plant J 42: 218-235
50. 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
51. Villegas RJA, Shimokawat T, Okuyama H, Kojima M (1987) Purification and characterization of chlorogenic acid: chlorogenate caffeoyl transferase in sweet potato roots. Phytochemistry 26: 1577-1581
52. 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
53. Walker K, Ketchum REB, Hezari M, Gatfield DD, Goleniowski M, Barthol A, Croteau R (1999) Partial purification and characterization of acetyl coenzyme A: taxa-4(20),11(12)-dien-5 alpha-ol O-acetyl transferase that catalyzes the first acylation step of taxol biosynthesis. Arch Biochem Biophys 364: 273-279
54. Wink M (1988) Plant breeding: importance of plant secondary metabolites for protection against pathogens and herbivores. Theor Appl Genet 75: 225-233
55. Winkel-Shirley B (2001) Flavonoid biosynthesis: a colorful model for genetics, biochemistry, cell biology, and biotechnology. Plant Physiol 126: 485-493
56. Winkel-Shirley B (2002) Biosynthesis of flavonoids and effects of stress. Curr Opin Plant Biol 5: 218-223
57. Wu X, Prior RL (2005) Identification and characterization of anthocyanins by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry in common foods in the United States: vegetables, nuts, and grains. J Agric Food Chem 53: 3101-3113
58. Yang Q, Reinhard K, Shiltz 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
59. Zambryski P, Joos H, Gentello C, Leemans J, van Montagu M, Schell J (1983) Ti plasmid vector for the introduction of DNA into plant cells without alteration of their normal regeneration capacity. EMBO J 2: 2143-2150
60. Zhou A, Li J (2005) Arabidopsis BRS1 is a secreted and active serine carboxypeptidase. J Biol Chem 280: 35554-35561