4-Deoxyaurone Formation in Bidens ferulifolia (Jacq.) DC

PLoS ONE

Volumn 8, Issue 5, 2013, Pages

  Miosic, Silvija ^a   Knop, Katrin ^b   Hölscher, Dirk ^c   Greiner, Jürgen ^a   Gosch, Christian ^a   Thill, Jana ^a   Kai, Marco ^c   Shrestha, Binita Kumari ^a   Schneider, Bernd ^c   Crecelius, Anna C ^b   Schubert, Ulrich S ^b   Svatoš, Aleš ^c   Stich, Karl ^a   Halbwirth, Heidi ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^c MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4 DEOXYAURONE; 6' DEOXYCHALCONE; ANTHOCHLOR; AURONE SYNTHASE; CAROTENOID; CATECHOL OXIDASE; CHALCONE 3 HYDROXYLASE; CHALCONE DERIVATIVE; ENZYME; FLAVONE DERIVATIVE; FLAVONOID; MARITIMETIN; OKANIN; PIGMENT; UNCLASSIFIED DRUG;

ANTIRRHINIUM MAJUS; ARABIDOPSIS THALIANA; ARTICLE; BIDENS; BIDENS FERULIFOLIA; BIOSYNTHESIS; CATALYSIS; CYCLIZATION; FLOWER; HYDROXYLATION; MASS SPECTROMETRY; NECTAR; NONHUMAN; ORNAMENTAL PLANT; PETAL; PH; PHOTOGRAPHY; PLANT; PLANT LEAF; PLANT ROOT; PLANT STEM; UV PHOTOGRAPHY;

BENZOFURANS; BIDENS; CAROTENOIDS; CATECHOL OXIDASE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLAVONOIDS; FLOWERS; HYDROGEN-ION CONCENTRATION; PIGMENTS, BIOLOGICAL; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; ULTRAVIOLET RAYS;

EID: 84877293353     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0061766     Document Type: Article

References (48)

1. Briscoe AD, Chittka L, (2001) The evolution of color vision in insects. Annual Review of Entomology 46: 471-510.
2. Harborne JB (1993) Introduction to ecological biochemistry: Academic Press.
3. Menzel R, Shmida A, (1993) The ecology of flower colours and the natural colour vision of insect pollinators: the Israeli flora as a study case. Biological Reviews 68: 81-120.
4. Chittka L, Shmida A, Troje N, Menzel R, (1994) Ultraviolet as a component of flower reflections, and the colour perception of Hymenoptera. Vision Research 34: 1489-1508.
5. Harborne JB, Smith DM, (1978) Anthochlors and other flavonoids as honey guides in the Compositae. Biochemical Systematics and Ecology 6: 287-291.
6. Scogin R, Zakar K, (1976) Anthochlor pigments and floral UV patterns in the genus Bidens. Biochemical Systematics and Ecology 4: 165-167.
7. McCrea KD, Levy M, (1983) Photographic visualization of floral colors as perceived by honeybee pollinators. American Journal of Botany pp. 369-375.
8. Daumer K, (1958) Blumenfarben, wie sie die Bienen sehen. Journal of Comparative Physiology A: Neuroethology, Sensory, Neural, and Behavioral Physiology 41: 49-110.
9. Davies KM, Marshall GB, Bradley JM, Schwinn KE, Bloor SJ, et al. (2006) Characterisation of aurone biosynthesis in Antirrhinum majus. Physiologia Plantarum 128: 593-603.
10. Harborne JB (1967) Comparative Biochemistry of Flavonoids. London: Academic Press.
11. Davies K, Schwinn K, Geneve R, Preece J, Merkle S (1997) Flower colour. In: Geneve RLP, J.E.Merkle, S.A., editor. Biotechnology of ornamental plants. Wallingford CAB INTERNATIONAL. pp. 259-294.
12. Wilson J, Wong E, (1976) Peroxidase catalysed oxygenation of 4, 2′, 4′-trihydroxychalcone. Phytochemistry 15: 1333-1341.
13. Farag MA, Deavours BE, De Fátima Â, Naoumkina M, Dixon RA, et al. (2009) Integrated metabolite and transcript profiling identify a biosynthetic mechanism for hispidol in Medicago truncatula cell cultures. Plant physiology 151: 1096-1113.
14. Sanchez-Gonzalez M, Rosazza JPN, (2006) Biocatalytic synthesis of butein and sulfuretin by Aspergillus alliaceus. Journal of agricultural and food chemistry 54: 4646-4650.
15. Nakayama T, Yonekura Sakakibara K, Sato T, Kikuchi S, Fukui Y, et al. (2000) Aureusidin synthase: a polyphenol oxidase homolog responsible for flower coloration. Science 290: 1163.
16. Ono E, Hatayama M, Isono Y, Sato T, Watanabe R, et al. (2006) Localization of a flavonoid biosynthetic polyphenol oxidase in vacuoles. The Plant Journal 45: 133-143.
17. Nakayama T, Sato M, Fukui Y, Yonekura-Sakakibara K, Hayashi H, et al. (2001) Specificity analysis and mechanism of aurone synthesis catalyzed by aureusidin synthase, a polyphenol oxidase homolog responsible for flower coloration. FEBS letters 499: 107-111.
18. Ono E, Fukuchi-Mizutani M, Nakamura N, Fukui Y, Yonekura-Sakakibara K, et al. (2006) Yellow flowers generated by expression of the aurone biosynthetic pathway. Proceedings of the National Academy of Sciences 103: 11075-11080.
19. Sato T, Nakayama T, Kikuchi S, Fukui Y, Yonekura-Sakakibara K, et al. (2001) Enzymatic formation of aurones in the extracts of yellow snapdragon flowers. Plant Science 160: 229-236.
20. Nakayama T, (2002) Enzymology of aurone biosynthesis. Journal of Bioscience and Bioengineering 94: 487-491.
21. Halbwirth H, Wimmer G, Wurst F, Forkmann G, Stich K, (1997) Enzymatic glucosylation of 4-deoxyaurones and 6′-deoxychalcones with enzyme extracts of Coreopsis grandiflora, Nutt. I. Plant Science 122: 125-131.
22. Shimada N, Aoki T, Sato S, Nakamura Y, Tabata S, et al. (2003) A cluster of genes encodes the two types of chalcone isomerase involved in the biosynthesis of general flavonoids and legume-specific 5-deoxy (iso) flavonoids in Lotus japonicus. Plant Physiology 131: 941-951.
23. Welle R, Grisebach H, (1988) Isolation of a novel NADPH-dependent reductase which coacts with chalcone synthase in the biosynthesis of 6′-deoxychalcone. FEBS Letters 236: 221-225.
24. Schlangen K, Miosic S, Topuz F, Muster G, Marosits T, et al. (2009) Chalcone 3-hydroxylation is not a general property of flavonoid 3′-hydroxylase. Plant Science 177: 97-102.
25. Strack D, Schliemann W, (2001) Bifunctional polyphenol oxidases: Novel functions in plant pigment biosynthesis. Angewandte Chemie International Edition 40: 3791-3794.
26. Bomati EK, Austin MB, Bowman ME, Dixon RA, Noel JP, (2005) Structural elucidation of chalcone reductase and implications for deoxychalcone biosynthesis. Journal of Biological Chemistry 280: 30496-30503.
27. Forkmann G, Heller W (1999) Biosynthesis of flavonoids. In: D Barton, KNakanishi, O Meth-Cohn, Sankawa U, editors. Comprehensive Natural Products Chemistry: Elsevier Science, Amsterdam. pp. 713-748.
28. Forkmann G, Dangelmayr B, (1980) Genetic control of chalcone isomerase activity in flowers of Dianthus caryophyllus. Biochemical Genetics 18: 519-527.
29. Bradley J, Winefield C, Schwinn K, Martin C, Bloor S, et al. (2000) Genetic engineering for yellow flower colours; pp. 39-44.
30. Wimmer G, Halbwirth H, Wurst F, Forkmann G, Stich K, (1998) Enzymatic hydroxylation of 6′-deoxychalcones with protein preparations from petals of Dahlia variabilis. Phytochemistry 47: 1013-1016.
31. Schlangen K, Miosic S, Thill J, Halbwirth H, (2010) Cloning, functional expression, and characterization of a chalcone 3-hydroxylase from Cosmos sulphureus. Journal of Experimental Botany 61: 3451-3459.
32. Arias E, Gonzalez J, Peiro J, Oria R, Lopez-Buesa P, (2007) Browning Prevention by Ascorbic Acid and 4-Hexylresorcinol: Different Mechanisms of Action on Polyphenol Oxidase in the Presence and in the Absence of Substrates. Journal of Food Science 72: C464-C470.
33. Mayer AM, (2006) Polyphenol oxidases in plants and fungi: Going places? A review. Phytochemistry 67: 2318-2331.
34. Halbwirth H, Waldner I, Miosic S, Ibanez M, Costa G, et al. (2009) Measuring Flavonoid Enzyme Activities in Tissues of Fruit Species. Journal of agricultural and food chemistry 57: 4983-4987.
35. Leonard AS, Papaj DR, (2011) 'X'marks the spot: The possible benefits of nectar guides to bees and plants. Functional Ecology 25: 1293-1301.
36. Guldberg LD, Atsatt PR, (1975) Frequency of reflection and absorption of ultraviolet light in flowering plants. American Midland Naturalist 93: 35-43.
37. Clark C, (1979) Ultraviolet absorption by flowers of the Eschscholzioideae (Papaveraceae). Madroño 26: 22-25.
38. Rieseberg LH, Schilling EE, (1985) Floral flavonoids and ultraviolet patterns in Viguiera (Compositae). American Journal of Botany 72: 999-1004.
39. Schlangen K, Miosic S, Castro A, Freudmann K, Luczkiewicz M, et al. (2009) Formation of UV-honey guides in Rudbeckia hirta. Phytochemistry 70: 889-898.
40. Thompson WR, Meinwald J, Aneshansley D, Eisner T, (1972) Flavonols: responsible for ultraviolet absorption in nectar guide of flower. Science 177: 528-530.
41. Hölscher D, Shroff R, Knop K, Gottschaldt M, Crecelius A, et al. (2009) Matrix free UV laser desorption/ionization (LDI) mass spectrometric imaging at the single cell level: distribution of secondary metabolites of Arabidopsis thaliana and Hypericum species. The Plant Journal 60: 907-918.
42. Shang Y, Venail J, Mackay S, Bailey PC, Schwinn KE, et al. (2011) The molecular basis for venation patterning of pigmentation and its effect on pollinator attraction in flowers of Antirrhinum. New Phytologist 189: 602-615.
43. Braune W, Leman A, Taubert H (1967) Pflanzenanatomisches Praktikum. Jena: Fischer VEV. pp. 23-39.
44. Halbwirth H, Kahl S, Jager W, Reznicek G, Forkmann G, et al. (2006) Synthesis of (14C)-labeled 5-deoxyflavonoids and their application in the study of dihydroflavonol/leucoanthocyanidin interconversion by dihydroflavonol 4-reductase. Plant Science 170: 587-595.
45. Chandra A, Rana J, Li Y, (2001) Separation, identification, quantification, and method validation of anthocyanins in botanical supplement raw materials by HPLC and HPLC-MS. Journal of agricultural and food chemistry 49: 3515-3521.
46. Vande Casteele K, Geiger H, Van Sumere CF, (1982) Separation of flavonoids by reversed-phase high-performance liquid chromatography. Journal of Chromatography A 240: 81-94.
47. Sandermann H, Strominger JL, (1972) Purification and properties of C55-isoprenoid alcohol phosphokinase from Staphylococcus aureus. Journal of Biological Chemistry 247: 5123-5131.
48. Halbwirth H, Muster G, Stich K, (2008) Unraveling the Biochemical Base of Dahlia Flower Coloration. Nat Prod Comm 3: 1259-1266.