Flavonol 3-O-glycoside hydroxycinnamoyltransferases from Scots pine (Pinus sylvestris L.)

FEBS Journal

Volumn 272, Issue 6, 2005, Pages 1415-1424

  Kaffarnik, Florian ^a,b   Heller, Werner ^a   Hertkorn, Norbert ^a   Sandermann Jr , Heinrich ^a  

^a INSTITUTE OF EPIDEMIOLOGY   (Germany)

^b SAINSBURY LABORATORY   (United Kingdom)

Author keywords

Diacylated flavonol 3 O glycosides; Hydroxycinnamoyl CoA flavonol 3 O glycoside hydroxycinnamoyltransferases; Pinus sylvestris; Scots pine

Indexed keywords

FERULIC ACID; FLAVONOL 3 O GLYCOSIDE HYDROXYCINNAMOYLTRANSFERASE; FLAVONOL DERIVATIVE; GLYCOSIDE; PARA COUMARIC ACID; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; BIOSYNTHESIS; ENZYME ACTIVE SITE; ENZYME ASSAY; ENZYME KINETICS; ENZYME SPECIFICITY; ISOELECTRIC POINT; MOLECULAR WEIGHT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; PRIORITY JOURNAL; SCOTS PINE; TEMPERATURE DEPENDENCE; ULTRAVIOLET RADIATION;

ACYLTRANSFERASES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; KINETICS; PINUS; PLANT PROTEINS; SUBSTRATE SPECIFICITY; TREES;

PINUS SYLVESTRIS;

EID: 15944417036     PISSN: 1742464X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1742-4658.2005.04574.x     Document Type: Article

References (35)

1. Hohlfeld H, Schürmann W, Scheel D & Strack D (1995) Partial purification and characterization of hydroxycinnamoyl-Coenzyme A: tyramine hydroxycinnamoyltransferase from cell suspension cultures of Solanum tuberosum. Plant Physiol 107, 545-552.
2. Matsukawa T, Isobe T, Ishihara A & Iwamura H (2000) Occurence of avenanthramides and hydroxycinnamoyl-CoA: hydroxyanthranilate N-hydroxycinnamoyltransferase activity in oat seeds. Z Naturforsch 55c, 30-36.
3. 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.
4. Callebaut A, Terahara N & Decleire M (1996) Anthocyanin acyltransferases in cell cultures of Ajuga reptans. Plant Sci 118, 109-118.
5. Kamsteeg J, van Brederode J, Hommels CH & van Nigtevecht G (1980) Identification, properties and genetic control of hydroxycinnamoyl-Coenzyme A: anthocyanidin 3-rhamnosyl (1-6) glucoside, 4‴-hydroxycinnamoyltransferase isolated from petals of Silene dioica. Biochem Physiol Pflanz 175, 403-411.
6. 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 localization of anthocyanin 5-aromatic acyltransferase from Gentiana triflora. Plant J 16, 421-431.
7. Yabuya T, Yamaguchi M-A, Fukui Y, Katoh K, Imayama T & Ino I (2001) Characterization of anthocyanin p-coumaroyltransferase in flowers of Iris ensata. Plant Sci 160, 499-503.
8. Heller W & Forkmann G (1993) Biosynthesis of flavonoids. In The Flavonoids: Advances in Research since 1986 (Harborne JB, ed), pp. 499-535. Chapman & Hall, London, UK.
9. Lehfeldt C, Shirley AM, Meyer K, Ruegger MO, Cusumano JC, Viitanen PV, Strack D & Chapple CCS (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.
10. Yonekura-Sakakibara K, Tanaka Y, Fukuzi-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.
11. 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, 765-768.
12. 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.
13. Ishihara A, Miyagawa H, Matsukawa T, Ueno T, Mayama S & Iwamura H (1998) Induction of hydroxyanthranilate hydroxycinnamoyl transferase activity by oligo-N-acetylchitooligosaccharides in oates. Phytochemistry 47, 969-974.
14. Yu M & Facchini PJ (1999) Purification, characterization, and immunolocalisation of hydroxycinnamoyl-CoA: tyramine N-(hydroxycinnamoyl) transferase from opium poppy. Planta 209, 33-44.
15. Hedberg C, Hesse M & Werner C (1996) Spermine and spermidine hydroxycinnamoyl transferase in Aphelandra tetragona. Plant Sci 113, 149-156.
16. 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, 95-103.
17. Hohlfeld M, Veit M & Strack D (1996) Hydroxycinnamoyltransferases involved in the accumulation of caffeic acid esters in gametophytes and sporophytes of Equisetum arvense. Plant Physiol 111, 1153-1159.
18. 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.
19. Suzuki H, Koike Y, Murakoshi I & Saito K (1996) Subcellular localization of acyltransferases for quinolizidine alkaloid biosynthesis in Lupinus. Phytochemistry 42, 1557-1562.
20. 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 Evolution of Metabolic Pathways (Romeo JT, Ibrahim R, Varin L & De Luca V, eds), 34, pp. 285-315. Pergamon, Amsterdam, the Netherlands.
21. Fujiwara H, Tanaka Y, Fukui Y, Ashikari T, Yamaguchi M & Kusumi T (1998) Purification and characterization of anthocyanin 3-aromatic acyltransferase from Perilla frutescens. Plant Sci 137, 87-94.
22. Von Roepenack-Lahaye E, Newman MA, Schornack S, Hammond-Kosack KE, Lahaye T, Jones JD, Daniels MJ & Dow JM (2003) p-Coumaroylnoradrenaline, a novel plant metabolite implicated in tomato defense against pathogens. J Biol Chem 278, 43373-43383.
23. Jang SM, 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.
24. Schnitzler J-P, Jungblut TP, Heller W, Köfferlein M, Hutzler P, Heinzmann U, Schmelzer E, Ernst D, Langebartels C & Sandermann H (1996) Tissue localization of UV-B-screening pigments and of chalcone synthase mRNA in needles of Scots pine seedlings. New Phytol 132, 247-258.
25. Fischbach R, Kossmann B, Fanten H, Steinbrecher R, Heller W, Seidlitz HK, Sandermann H, Hertkorn N & Schnitzler J-P (1999) Seasonal accumulation of ultraviolet-B screening pigments in needles of Norway spruce (Picea abies (L.) Karst.). Plant Cell Environ 22, 27-37.
26. Jungblut TP, Schnitzler J-P, Heller W, Hertkorn N, Metzger JW, Szymczak W & Sandermann H (1995) Structures of UV-B induced sunscreen pigments of the Scots pine (Pinus sylvestris L.). Angew Chem Int Ed English 34, 312-314.
27. Romussi G, Parodi B & Caviglioli G (1991) Flavonoid-glycoside aus Quercus pubescens Willd., Quercus cerris L. und Quercus ilex L. Pharmazie 46, 679.
28. Jungblut TP (1996) Wirkung von UV-B Strahlung und Ozon auf den Sekundärstoffwechsel der Kiefer (Pinus sylvestris L.). PhD Thesis, Ludwig-Maximilians-University, Munich, Germany.
29. Romussi G, Cafaggi S & Ciarallo G (1983) Ein neues acyliertes Flavonolglycosid aus Quercus ilex L. Liebigs Ann Chem, 334-335.
30. Rhodes MJC, Wooltorton LSC & Lourenco EJ (1979) Purification and properties of hydroxycinnamoyl CoA quinate hydroxycinnamoyl transferase from potatoes. Phytochemistry 18, 1125-1129.
31. Winkel BSJ (2004) Metabolic channeling in plants. Annu Rev Plant Biol 55, 85-107.
32. Stöckigt J & Zenk MH (1975) Chemical synthesis and properties of hydroxycinnamoyl-Coenzyme A derivatives. Z Naturforsch 30c, 352-358.
33. Bradford M (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72, 248-254.
34. Dellus V, Heller W, Sandermann H & Scalbert A (1997) Dihydroflavonol 4-reductase activity in lignocellulosic tissues. Phytochemistry 45, 1415-1418,
35. Moya-Leon MA & John P (1995) Purification and biochemical characterization of 1-aminocyclopropane-1-carboxylate oxidase from banana fruit. Phytochemistry 39, 15-20.