Polymethylated myricetin in trichomes of the wild tomato species solanum habrochaites and characterization of trichome-specific 3'/5'- and 7/4'-myricetin O-methyltransferases

Plant Physiology

Volumn 155, Issue 4, 2011, Pages 1999-2009

  Schmidt, Adam ^a   Li, Chio ^b   Shi, Feng ^c   Jones, A Daniel ^c   Pichersky, Eran ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b MICHIGAN STATE UNIVERSITY   (United States)

^c Michigan State University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LYCOPERSICON ESCULENTUM; LYCOPERSICON HIRSUTUM; SOLANUM;

EID: 79953724043     PISSN: 00320889     EISSN: 15322548     Source Type: Journal    
DOI: 10.1104/pp.110.169961     Document Type: Article

References (68)

1. Ambrósio SR, Oki Y, Heleno VCG, Chaves JS, Nascimento PG, Lichston JE, Constantino MG, Varanda EM, Da Costa FB (2008) Constituents of glandular trichomes of Tithonia diversifolia: relationships to herbivory and antifeedant activity. Phytochemistry 69: 2052-2060
2. Ariyanathan S, Saraswathy A, Rajamanickam GV, Connolly JD (2010) Polyphenols from the roots of Plumbago rosea. Indian J Chem Sect B Org Chem Incl Med Chem 49: 386-389
3. Braca A, Bilia AR, Mendez J, Morelli I (2001) Myricetin glycosides from Licania densiflora. Fitoterapia 72: 182-185
4. Buer CS, Imin N, Djordjevic MA (2010) Flavonoids: new roles for old molecules. J Integr Plant Biol 52: 98-111
5. Cacace S, Schröder G, Wehinger E, Strack D, Schmidt J, Schröder J (2003) A flavonol O-methyltransferase from Catharanthus roseus performing two sequential methylations. Phytochemistry 62: 127-137
6. Cimanga K, Ying L, De Bruyne T, Apers S, Cos P, Hermans N, Bakana P, Tona L, Kambu K, Kalenda DT, et al (2001) Radical scavenging and xanthine oxidase inhibitory activity of phenolic compounds from Bridelia ferruginea stem bark. J Pharm Pharmacol 53: 757-761
7. Croteau RB, Davis EM, Ringer KL, Wildung MR (2005) (2)-Menthol biosynthesis and molecular genetics. Naturwissenschaften 92: 562-577
8. Cuyckens F, Claeys M (2005) Determination of the glycosylation site in flavonoid mono-O-glycosides by collision-induced dissociation of elec-trospray-generated deprotonated and sodiated molecules. J Mass Spec-trom 40: 364-372
9. Dachriyanus, Fahmi R, Sargent MV, Skelton BW, White AH (2004) 5-Hydroxy-3,3',4',5',7-pentamethoxyflavone (combretol). Acta Crystal-logr Sect E Struct Rep Online 60: 086-088
10. D'Auria JC, Chen F, Pichersky E (2002) Characterization of an acyltrans-ferase capable of synthesizing benzylbenzoate and other volatile esters in flowers and damaged leaves of Clarkia breweri. Plant Physiol 130: 466-476
11. De Luca V, Ibrahim RK (1985) Enzymatic synthesis of polymethylated flavonols in Chrysosplenium americanum. I. Partial purification and some properties of S-adenosyl-L-methionine:flavonol 3-, 6-, 7-, and 4'-O-methyltransferases. Arch Biochem Biophys 238: 596-605
12. Dudareva N, Cseke L, Blanc VM, Pichersky E (1996) Evolution of floral scent in Clarkia: novel patterns of S-linalool synthase gene expression in the C. breweri flower. Plant Cell 8: 1137-1148
13. Felsenstein J (1985) Confidence limits on phylogenies: an approach using the bootstrap. Evolution 39: 783-791
14. Gerats AGM, Wallroth M, Donkerkoopman W, Groot SPC, Schram AW (1983) The genetic control of the enzyme UDP-glucose-3-O-flavonoid-glucosyltransferase in flowers of Petunia hybrida. Theor Appl Genet 65: 349-352
15. Gorbatsova J, Lõugas T, Vokk R, Kaljurand M (2007) Comparison of the contents of various antioxidants of sea buckthorn berries using CE. Electrophoresis 28: 4136-4142
16. Huang TS, Anzellotti D, Dedaldechamp F, Ibrahim RK (2004) Partial purification, kinetic analysis, and amino acid sequence information of a flavonol 3-O-methyltransferase from Serratula tinctoria. Plant Physiol 134: 1366-1376
17. Ibrahim RK (1997) Plant O-methyltransferase signatures. Trends Plant Sci 2: 249-250
18. Ibrahim RK (2005) A forty-year journey in plant research: original contributions to flavonoid biochemistry. Can J Bot 83: 433-450
19. Ibrahim RK, Anzellotti D (2003) The enzymatic basis of flavonoid biodiversity. In JT Romeo, ed, Integrative Phytochemistry: From Ethnobotany to Molecular Ecology. Pergamon, Amsterdam, pp 1-36
20. Ibrahim RK, De Luca V, Khouri H, Latchinian L, Brisson L, Charest PM (1987) Enzymology and compartmentation of polymethylated flavonol glucosides in Chrysosplenium americanum. Phytochemistry 26: 1237-1245
21. Iijima Y, Gang DR, Fridman E, Lewinsohn E, Pichersky E (2004) Characterization of geraniol synthase from the peltate glands of sweet basil. Plant Physiol 134: 370-379
22. Jay M, Voirin B, Hasan A, Gonnet JF, Viricel MR (1980) Chemotaxonomic study of vascular plants. 43. Chemosystematic experiment on tribe Loteae. Biochem Syst Ecol 8: 127-132
23. Joshi CP, Chiang VL (1998) Conserved sequence motifs in plant S-adenosyl-L-methionine-dependent methyltransferases. Plant Mol Biol 37: 663-674
24. Jung HA, Kim JE, Chung HY, Choi JS (2003) Antioxidant principles of Nelumbo nucifera stamens. Arch Pharm Res 26: 279-285
25. Kobus J, Flaczyk E, Siger A, Nogala-Kalucka M, Korczak J, Pegg RB (2009) Phenolic compounds and antioxidant activity of extracts of Ginkgo leaves. Eur J Lipid Sci Technol 111: 1150-1160
26. Kumar A, Malik AK, Tewary DK (2009) A new method for determination of myricetin and quercetin using solid phase microextraction-high performance liquid chromatography-ultraviolet/visible system in grapes, vegetables and red wine samples. Anal Chim Acta 631: 177-181
27. Kumar N, Bhandari P, Singh B, Gupta AP, Kaul VK (2008) Reversed phase-HPLC for rapid determination of polyphenols in flowers of rose species. J Sep Sci 31: 262-267
28. Kumari GNK, Rao LJM, Rao NSP (1984) Myricetin methyl ethers from Solanum pubescens. Phytochemistry 23: 2701-2702
29. Lako J, Trenerry VC, Wahlqvist M, Wattanapenpaiboon N, Sotheeswaran S, Premier R (2007) Phytochemical flavonols, carotenoids and the antioxidant properties of a wide selection of Fijian fruit, vegetables and other readily available foods. Food Chem 101: 1727-1741
30. Le K, Chiu F, Ng K (2007) Identification and quantification of antioxidants in Fructus lycii. Food Chem 105: 353-363
31. Lee TH, Liu DZ, Hsu FL, Wu WC, Hou WC (2006) Structure-activity relationships of five myricetin galloylglycosides from leaves of Acacia confusa. Botanical Studies 47: 37-43
32. Lee YJ, Kim BG, Chong Y, Lim Y, Ahn JH (2008) Cation dependent O-methyltransferases from rice. Planta 227: 641-647
33. Liu Y, Li WJ, Ling XM, Lai XY, Li YZ, Zhang QY, Zhao YY (2008) Simultaneous determination of the active ingredients in Abelmoschus manihot (L.) Medicus by CZE. Chromatographia 67: 819-823
34. Luckwill L (1943) The genus Lycopersicon: an historical, biological, and taxonomic survey of the wild and cultivated tomatoes. PhD thesis. Aberdeen University, Aberdeen, UK
35. Macheix JJ, Ibrahim RK (1984) The O-methylation system of apple fruit cell suspension. Biochem Physiol Pflanz 179: 659-664
36. Mattivi F, Guzzon R, Vrhovsek U, Stefanini M, Velasco R (2006) Metabolite profiling of grape: flavonols and anthocyanins. J Agric Food Chem 54: 7692-7702
37. McDowell ET, Kapteyn J, Schmidt A, Li C, Kang JH, Descour A, Shi F, Larson M, Schilmiller A, An L, et al (2011) Comparative functional genomic analysis of Solanum glandular trichome types. Plant Physiol 155: 524-539
38. Michodjehoun-Mestres L, Souquet JM, Fulcrand H, Bouchut C, Reynes M, Brillouet JM (2009) Monomeric phenols of cashew apple (Anacar-dium occidentale L.). Food Chem 112: 851-857
39. Min BS, Lee SY, Kim JH, Lee JK, Kim TJ, Kim DH, Kim YH, Joung H, Lee HK, Nakamura N, et al (2003) Anti-complement activity of constituents from the stem-bark of Juglans mandshurica. Biol Pharm Bull 26: 1042-1044
40. Modolo LV, Li LN, Pan HY, Blount JW, Dixon RA, Wang XQ (2009) Crystal structures of glycosyltransferase UGT78G1 reveal the molecular basis for glycosylation and deglycosylation of (iso)flavonoids. J Mol Biol 392: 1292-1302
41. Motta LB, Kraus JE, Salatino A, Salatino MLF (2005) Distribution of metabolites in galled and non-galled foliar tissues of Tibouchina pulchra. Biochem Syst Ecol 33: 971-981
42. Muzac I, Wang J, Anzellotti D, Zhang H, Ibrahim RK (2000) Functional expression of an Arabidopsis cDNA clone encoding a flavonol 3'-O-methyltransferase and characterization of the gene product. Arch Biochem Biophys 375: 385-388
43. Ojot PB, Njiti V, Guo ZB, Gao M, Besong S, Barnes SL (2008) Variation of flavonoid content among sweetpotato accessions. J Am Soc Hortic Sci 133: 819-824
44. Oliveira I, Sousa A, Valentao P, Andrade PB, Ferreira I, Ferreres F, Bento A, Seabra R, Estevinho L, Pereira JA (2007) Hazel (Corylus avellana L.) leaves as source of antimicrobial and antioxidative compounds. Food Chem 105: 1018-1025
45. Owens DK, McIntosh CA (2009) Identification, recombinant expression, and biochemical characterization of a flavonol 3-O-glucosyltransferase clone from Citrus paradisi. Phytochemistry 70: 1382-1391
46. Rausher MD (2008) The evolution of flavonoids and their genes. In E Grotewold, ed, Science of Flavonoids. Springer, New York, pp 175-211
47. Reynertson KA, Yang H, Jiang B, Basile MJ, Kennelly EJ (2008) Quantitative analysis of antiradical phenolic constituents from fourteen edible Myrtaceae fruits. Food Chem 109: 883-890
48. Riihinen K, Jaakola L, Karenlampi S, Hohtola A (2008) Organ-specific distribution of phenolic compounds in bilberry (Vaccinium myrtillus) and 'northblue' blueberry (Vaccinium co rymbosum 3 V. angustifolium). Food Chem 110: 156-160
49. Saitou N, Nei M (1987) The neighbor-joining method: a new method for reconstructing phylogenetic trees. Mol Biol Evol 4: 406-425
50. Schilmiller A, Shi F, Kim J, Charbonneau AL, Holmes D, Daniel Jones A, Last RL (2010) Mass spectrometry screening reveals widespread diversity in trichome specialized metabolites of tomato chromosomal substitution lines. Plant J 62: 391-403
51. Schilmiller AL, Last RL, Pichersky E (2008) Harnessing plant trichome biochemistry for the production of useful compounds. Plant J 54: 702-711
52. Schmittgen TD, Livak KJ (2008) Analyzing real-time PCR data by the comparative C(T) method. Nat Protoc 3: 1101-1108
53. Schröder G, Wehinger E, Lukacin R, Wellmann F, Seefelder W, Schwab W, Schröder J (2004) Flavonoid methylation: a novel 4'-O-methyltransfer-ase from Catharanthus roseus, and evidence that partially methylated flavanones are substrates of four different flavonoid dioxygenases. Phytochemistry 65: 1085-1094
54. Singh AP, Luthria D, Wilson T, Vorsa N, Singh V, Banuelos GS, Pasakdee S (2009) Polyphenols content and antioxidant capacity of eggplant pulp. Food Chem 114: 955-961
55. Stevens JF, Hart H, Elema ET, Bolck A (1996) Flavonoid variation in Eurasian Sedum and Sempervivum. Phytochemistry 41: 503-512
56. Stevens JF, Hart HT, Wollenweber E (1995) The systematic and evolutionary significance of exudate flavonoids in Aeonium. Phytochemistry 39: 805-813
57. Tabart J, Kevers C, Pincemail J, Defraigne JO, Dommes J (2006) Antiox-idant capacity of black currant varies with organ, season, and cultivar. J Agric Food Chem 54: 6271-6276
58. Tamura K, Dudley J, Nei M, Kumar S (2007) MEGA4: Molecular Evolutionary Genetics Analysis (MEGA) software version 4.0. Mol Biol Evol 24: 1596-1599
59. Taylor LP, Grotewold E (2005) Flavonoids as developmental regulators. Curr Opin Plant Biol 8: 317-323
60. Thresh K, Ibrahim RK (1985) Are spinach chloroplasts involved in flavo-noid O-methylation? Z Naturforsch C 40: 331-335
61. Treutter D (2005) Significance of flavonoids in plant resistance and enhancement of their biosynthesis. Plant Biol 7: 581-591
62. Vogt T (2004) Regiospecificity and kinetic properties of a plant natural product O-methyltransferase are determined by its N-terminal domain. FEBS Lett 561: 159-162
63. Vogt T, Jones P (2000) Glycosyltransferases in plant natural product synthesis: characterization of a supergene family. Trends Plant Sci 5: 380-386
64. Wagner GJ (1991) Secreting glandular trichomes: more than just hairs. Plant Physiol 96: 675-679
65. Williams CA, Grayer RJ (2004) Anthocyanins and other flavonoids. Nat Prod Rep 21: 539-573
66. Wu JH, Huang CY, Tung YT, Chang ST (2008) Online RP-HPLC-DPPH screening method for detection of radical-scavenging phytochemicals from flowers of Acacia confusa. J Agric Food Chem 56: 328-332
67. Zhou JM, Gold ND, Martin VJJ, Wollenweber E, Ibrahim RK (2006) Sequential O-methylation of tricetin by a single gene product in wheat. Biochim Biophys Acta 1760: 1115-1124
68. Zuckerkandl E, Pauling L (1965) Evolutionary divergence and convergence in proteins. In V Bryson, HJ Vogel, eds, Evolving Genes and Proteins. Academic Press, New York, pp 97-166