Photochemistry of flavonoids

Molecules

Volumn 15, Issue 8, 2010, Pages 5196-5245

  Sisa, Miroslav ^a   Bonnet, Susan L ^a   Ferreira, Daneel ^b   Van Der Westhuizen, Jan H ^a  

^a UNIVERSITY OF THE FREE STATE   (South Africa)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Chalcones; Flavonoids; Photochemistry; Photoinduction; Photooxygenation; Phototransformation; Polyphenols; Tannins; UV radiation

Indexed keywords

FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE; FLAVONOID; FLAVONOL DERIVATIVE; HYDROGEN;

CHEMISTRY; PHOTOCHEMISTRY; REVIEW;

FLAVANONES; FLAVONES; FLAVONOIDS; FLAVONOLS; HYDROGEN; PHOTOCHEMICAL PROCESSES;

EID: 77956098732     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15085196     Document Type: Review

References (102)

1. Haslam, E. Chemistry and Pharmacology of Natural Products. Plant Polyphenols: Vegetable Tannins Revisited; Cambridge University Press: Sydney, Australia, 1989; p. 8.
2. Smith, M.A.; Perry, G.; Richey, P.L.; Sayre, L.M.; Anderson, V.E.; Beal, M.F.; Kowall, N. Oxidative Damage in Alzheimers. Nature 1996, 382, 120-121.
3. Corder, R.; Mullen, W.; Khan, N.Q.; Marx, S.C.; Woods, E.G.; Carrier, M.J.; Crozier, A. Oenology: Red Wine Procyanidins and Vascular Health. Nature 2006, 444, 566.
4. Jankun, J.; Selman, S.H.; Swiercz, R.; Skrypczak-Jankun, E. Why Drinking Green Tea Could Prevent Cancer. Nature 1997, 387, 561.
5. Garbisa, S.; Biggin, S.; Cavallarin, N.; Sartor, L.; Benelli, R.; Albini, A. Tumor Invasion: Molecular Shears Blunted by Green Tea. Nat. Med. 1999, 5, 1216.
6. Prasain, J.K.; Carlson, S.H.; Wyss, J.M. Flavonoids and Age-related Disease: Risk, Benefits and Critical Windows. Maturitas 2010, in press.
7. Pietta, P.G. Flavonoids as Antioxidants. J. Nat. Prod. 2000, 63, 1035-1042.
8. Schroeter, H.; Heiss, C.; Balzer, J.; Kleinbongard, P.; Keen, C.L.; Hollenberg, K.; Sies, H.; Kwik-Uribe, C.; Schmitz, H.H.; Kelm, M. (-)-Epicatechin Mediates Beneficial Effects of Flavanol-rich Cocoa on Vascular Function in Humans. Proc. Natl. Acad. Sci. USA 2006, 103, 1024-1029.
9. Arai, Y.; Watanabe, S.; Kimira, M.; Shimoi, K.; Mochizuki, R.; Kinae, Naohide. Dietary Intakes of Flavonols, Flavones and Isoflavones by Japanese Women and the Inverse Correlation between Quercetin Intake and Plasma LDL Cholesterol Concentration. J. Nutr. 2000, 130, 2243-2250.
10. Kootstra, A. Protection from UV-B-induced DNA Damage by Flavonoids. Plant Mol. Biol. 1994, 26, 771-774.
11. He, J.; Santos-Buelga, C.; Mateus, N.; de Freitas, V. Isolation and Quantification of Oligomeric Pyranoanthocyanin-flavanol Pigments from Red Wines by Combination of Column Chromatographic Techniques. J. Chromatogr. A 2006, 1134, 215-225.
12. Hergert, H.L. Condensed Tannins in Adhesives: Introduction and Historical Perspectives; Repap Technologies Inc.: Valley Forge, PA, USA, 1989; Volume 385, pp. 155-171.
13. Robertson, A. The Chemistry and Biochemistry of Black Tea Production - the non-volatiles. In Tea: Cultivation to Consumption; Wilson, K.C., Clifford, M.N., Eds.; Kluwer Acad. Publ.: Dordrecht, The Netherlands, 1991; pp. 574-580.
14. Codorniu-Hernández, E.; Mesa-Ibirico, A.; Montero-Cabrera, L.A.; Martínez-Luzardo, F.; Borrmann, T.; Stohrer, W.-D. Theoretical Study of Flavonoids and Proline Interactions. Aqueous and Gas Phases. J. Mol. Struct. (Theochem) 2003, 623, 63-73.
15. Van Andel, T. The Diverse Uses of Fish-Poison Plants in Northwest Guyana. Econ. Bot. 2000, 54, 500-512.
16. Stermitz, F.R.; Adamovics, J.A.; Geigert, J. Synthesis and Photoreactions of Sorbophenones: A Photochemical Synthesis of Flavones. Tetrahedron 1975, 31, 1593-1595.
17. Winkel-Shirley, B. Biosynthesis of Flavonoids and Effects of Stress. Curr. Opin. Plant Biol. 2002, 5, 218-223.
18. Arthur, J.M. Radiation and Anthocyanin Pigments. In Biological Effects of Radiation; Duggar, B.M., Ed.; McGraw-Hill: New York, NY, USA, 1936; Volume 2, pp. 1109-1118.
19. Siegelman, H.W.; Hendricks, S.B. Photocontrol of Anthocyanin Formation in Turnip and Red Cabbage Seedlings. Plant Physiol. 1957, 32, 393-398.
20. Hahlbrock, K.; Ebel, J.; Ortmann, R.; Sutter, A.; Wellmann, E.; Grisebach, H. Regulation of enzyme activities related to the biosynthesis of flavone glycosides in cell suspension cultures of parsley Petroselium hortense. Biochim. Biophys. Acta 1971, 244, 7-15.
21. Wellmann, E.; Hrazdina, G.; Grisebach, H. Induction of Anthocyanin Formation and of Enzymes Related to its Biosynthesis by UV Light in Cell Cultures of Haplopappus gracilis. Phytochemistry 1976, 15, 913-915.
22. Taylor, L.P.; Grotewold, E. Flavonoids as Developmental Regulators. Curr. Opin. Plant Biol. 2005, 8, 317-323.
23. Hernández, I.; Alegre, L.; Van Breusegem, F.; Munné-Bosch, S. Haw Relevant are Flavonoids as Antioxidant in Plants? Trends Plant Sci. 2009, 14, 125-132.
24. Agati, G.; Tattini, M. Multiple Functional Roles of Flavonoids in Photoprotection New Phytol. 2010, 186, 786-793.
25. Roberts, M.R.; paul, N.D. Seduced by the Dark Side: Integrating Molecular and Ecological Perspectives on the Infuence of Light on Plant Defence against Pets and Pathogens. New Phytol. 2006, 170, 677-699.
26. Caldwell, M.M. Solar UV Irradiation and the Growth and Development of Higher Plants. Photophysiology 1971, 6, 131-177.
27. Cavaleri, J.J.; Prater, K.; Bowman, R.M. An Investigation of the Solvent Dependence on the Ultrafast Intersystem Crossing Kinetics of Xanthone. Chem. Phys. Lett. 1996, 259, 495-502.
28. Gupta, R.C.; Jain, A.C.; Saini, H.R. Photochemistry of flavonoids. J. Sci. Ind. Res. 1978, 37, 264-273.
29. Sundaryono, A.; Nourmamode, A.; Gardrat, C.; Grelier, S.; Bravic, G.; Chasseau, D.; Castellan, A. Studies on the Photochemistry of 1,7-diphenyl-1,6-heptadiene-3,5-dione, a Non-phenolic curcuminoid Model. Photochem. Photobiol. Sci. 2003, 2, 914-920.
30. Monici, M.; Mulinacci, N.; Baglioni, P.; Vincieri, F.F. Flavone Photoreactivity. UV-induced Reactions in Organic Solvents and Micellar Systems. J. Photochem. Photobiol. B: Biol. 1993, 20, 167-172.
31. Waiss, A.C., Jr.; Corse, J. Photooxidative Cyclization of Quercetin Pentamethyl Ether. J. Am. Chem. Soc. 1965, 87, 2068-2069.
32. Waiss, A.C., Jr.; Lundin, A.L.; Lee, A.; Corse J. Photochemistry of Quercetin Pentamethyl Ether. J. Am. Chem. Soc. 1967, 89, 6213-6218.
33. Matsuura, T.; Matsushima, H.; Sakamato, H. Photosensitized Oxygenation of 3-Hydroxyflavones a Possible Model for Biological Oxygenation. J. Am. Chem. Soc. 1967, 89, 6370-6371.
34. Matsuura, T.; Matsushima, H.; Nakashima, R. Photoinduced Reactions - XXXVI: Photosensitized Oxygenation of 3-Hydroxyflavones as a Nonenzymatic Model for Quercetinase. Tetrahedron 1970, 26, 435-443.
35. Matsuura, T.; Matsushima, H. Photoinduced Reactions - XXII: Photooxidative Cyclization of 3-Methoxyflavones. Tetrahedron 1968, 24, 6615-6618.
36. Suginome, H.; Yomezawa, T.; Masamune, T. Photoinduced Oxygenation of Dehydrorotenones. Tetrahedron Lett. 1968, 49, 5079-5082.
37. Thakur, M.; Berar, S.; Berar, U.; Arora, S.; Gupta, S.C.; Kamboj, R.C. Phototransformations of 6-Chloro-3-propargyloxy-2-aryl-4-oxo-4H-1-benzopyran: 1,4-Hydrogen Abstraction in Propargylethers. Tetrahedron 2008, 64, 5168-5173.
38. Matsuura, T.; Takemoto, T.; Nakashima, R. Photoinduced Reactions LII: Photorearrangement of 3-Hydroxyflavones. Tetrahedron Lett. 1971, 19, 1539-1540.
39. Matsuura, T.; Takemoto, T.; Nakashima, R. Photoinduced Reactions - LXXI*1: Photorearrangement of 3-Hydroxyflavones to 3-Aryl-3-hydroxy-1,2- indandiones. Tetrahedron 1973, 29, 3337-3340.
40. Porter, G.; Suppan, P. Reactivity of Excited States of Aromatic Ketones. Pure Appl. Chem. 1964, 9, 499-506.
41. Porter, G.; Suppan, P. Primary Photochemical Processes in Aromatic Molecules. Part 12. - Excited States of Benzophenone Derivatives. Trans. Faraday Soc. 1965, 61, 1664-1673.
42. Hammond, G.S.; Leermakers, P.A. Mechanisms of Photoreactions in Solution. X. Relative Efficiencies of Various Quenchers in the Photoreduction of Benzophenone. J. Phys. Chem. 1962, 66, 1148-1150.
43. Yokoe, I.; Higushi, K.; Shirataki, Y.; Komatsu, M. Photochemistry of Flavonoids. III. Photorearrangement of Flavonols. Chem. Pharm. Bull. 1981, 29, 894-898.
44. Ficarra, R.; Ficarra, P.; Tommasini, S.; Campagna, S.; Guglielmo, G. Photochemistry of Flavonoids. Solvent Effect on Photochemically of 3-Hydroxyflavone. Boll. Chim. Farm. 1994, 133, 665-669.
45. Chen, C.F.; Zhu, Y.; Liu, J.C.; Xu, J.H. Photoinduced Electron Transfer Reactions of Flavone with Amines - The Syntheses of 2,4′-and 2,2′-Biflavanoids. Tetrahedron Lett. 1995, 36, 2835-2838.
46. Yoon, U.C.; Mariano, P.S. Mechanistic and Synthetic Aspects of Amine-enone Single Electron Transfer Photochemistry. Acc. Chem. Res. 1992, 25, 233-240.
47. Chen, A.H.; Kuo, W.B.; Chen, C.W. Photochemical Synthesis of 2,2′-Biflavanones from Flavone. J. Chin. Chem. Soc. 2003, 50, 123-127.
48. Yokoe, I.; Tagushi, M.; Shirataki, Y.; Komatsu, M. Photochemical Dimerization of Flavones. J. Chem. Soc. Commun. 1979, 333-334.
49. Schönberg, A.; Khandelwal, G.D. 1,2-Cycloadditionen von Diphenylacetylen an Flavone. Chem. Ber. 1970, 103, 2780-2863.
50. Gerard, B; Jones, G.; Porco, J.A., Jr. A Biomimetic Approach to the Rocaglamides Employing Photogeneration of Oxidopyryliums Derived from 3-Hydroxyflavones. J. Am. Chem. Soc. 2004, 126, 13620-13621.
51. Gerard, B.; Sangji, S.; O'Leary, D.J.; Porco, J.A., Jr. Enantioselective Photocycloaddition Mediated by Chiral Bronsted Acids: Asymmetric Synthesis of the Rocaglamides. J. Am. Chem. Soc. 2006, 128, 7754-7755.
52. Bhattacharyya, K.; Ramaiah, D.; Das, P.K.; Goerge, M.V. A Laser Flas Photolysis Study of 2,6-Dimethyl-3,5-Diphenyl-4-pyrone and Related Chromones. Evidence for Triplet State Structural Relaxation from Quenching Behaviors. J. Phys. Chem. 1986, 90, 5984-5989.
53. Schuster, D.I.; Bonneau, R.; Dunn, D.A.; Rao, J.M.; Joussot-Dubien. Photochemistry of ketones in solution. 72. Characterization of transient intermediates in the photochemistry of cyclohexenones J. J. Am. Chem. Soc. 1984, 106, 2706-2707.
54. Schuster, D.I.; Dunn, D.A.; Bonneau, R. Kinetic properties of the triplet excited state of a linearly conjugated steroid dienone studied by laser flash photolysis. J. Photochem. 1985, 28, 413-418.
55. Christoff, M.; Toscano, V.G.; Baader, W.J. Influence of Methoxy Substitution on Flavonoid Photophysics: a Steady State and Laser Flash Photolysis Study. J. Photochem. Photobiol. A: Chem. 1996, 101, 11-20.
56. Lutz, R.E.; Jordan, R.H. Cis-benzalacetophenone. J. Am. Chem. Soc. 1950, 72, 4090-4091.
57. Du R. Volsteedt, F.; Rall, G.J.H.; Roux, D.G. Cis-Trans Isomerism of a New α-Hydroxychalcone from Berchemia Zeyheri Sond. (Red Ivory). Tetrahedron Lett. 1973, 12, 1001-1004.
58. Ferreira, D.; Roux, D.G. Novel Conversion and Coupling Reactions of Chalcones and their Epoxides. J. Chem. Soc., Perkin Trans. I 1977, 134-138.
59. Dewar, D.; Sutherland, G. The Photolysis of 2-Hydroxychalcone and Its Possible Implication in Flavonoid Biosynthesis. Chem. Commun. 1970, 272-273.
60. Mack, P.O.; Pinhey, J.T. The Photochemistry of Flavanone. J. Chem. Soc. Chem. Commun. 1972, 451-452.
61. Stermitz, F.R.; Adamovic, J.A.; Geigert, J. Synthesis and Photoreactions of Sorbophenones. A Photochemical Synthesis of Flavone. Tetrahedron 1975, 37, 1593-1595.
62. Becker, R.S. Theory and Interpretation of Fluorescence and Phosphorescence; Wiley-Interscience: New York, NY, USA, 1969; p. 240.
63. Matsushima, R.; Kishimoto, T.; Suzuki, M. Photoreactions via π-π* and n-π* Triplet States of Flavanones. Chem. Lett. 1976, 579-580.
64. Nakashima, R.; Okamoto, K.; Matsuura, T. Photoreactions of Flavanones. Bull. Chem. Soc. Jpn. 1976, 49, 3355-3356.
65. Matsushima, R.; Hirao, I. Photocyclization of 2′-Hydroxyflavones to 4-Flavanones. Bull. Chem. Soc. Jpn. 1980, 53, 518-522.
66. Padwa, A.; Au, A.; Lee, G.A.; Owens, W. Carbonyl Group Photochemistry via the Enol Form. Photoisomerization of 4-Substituted 3-Chromanones. J. Am. Chem. Soc. 1976, 98, 3555-3564.
67. Matsushima, R.; Kageyama, H. Photochemical Cyclization of 2′Hydroxychalcones. J. Chem. Soc., Perkin Trans. II 1985, 743-748.
68. Gresh, O.L.; Markovits, Y.; Shani, A. On the Mechanism of Intramolecular Photocycloaddition of Substituted o-Allylphenols to Cyclic Ethers. Tetrahedron 1975, 31, 2803-2807.
69. Smith, K.K.; Kaufmann, K.J. Solvent Dependence of the Nonradiative Decay Rate of Methyl Salicylate. J. Phys. Chem. 1981, 85, 2895-2897.
70. Nagaoka, S.; Hirota, N.; Sumitani, M.; Yoshirama, K. Investigation of the Dynamic Processes of the Excited States of o-Hydroxybenzaldehyde and o-Hydroxyacetophenone by Emission and Picosecond Spectroscopy. J. Am. Chem. Soc. 1983, 105, 4220-4226.
71. Jain, S. Photolysis of some Flavanones by Ultraviolet Irradiations. Nat. Acad. Sci. Lett. 1997, 20, 130-132.
72. Obara, H.; Takahashi, H. The Photochemical Fries Rearrangement of Phenyl Cinnamate. Bull. Chem. Soc. Jpn. 1967, 40, 1012-1012
73. Obara, H.; Takahashi, H.; Hirano, H. The Photo-Fries Rearrangement of Hydroxyphenyl Cinnamates. Bull. Chem. Soc. Jpn. 1969, 42, 560-561.
74. Onodera, J.; Obara, H. The Photo-Frie Rearrangement of Bis(methoxy)-phenyl Cinnamates. Bull. Chem. Soc. Jpn. 1974, 47, 240-241.
75. Bhatia, V.K.; Kagan, J. A Photochemical Synthesis of 2′,6′- Dihydroxy-4′-methoxy-and 2′,4′-Dihydroxy-6′- methoxychalcones. Chem. Ind. 1970, 1203-1204.
76. Ramakrishnan, V.T.; Kagan, J. The Photochemical Synthesis of 2′-Hydroxychalcones from Phenyl Cinnamates. J. Org. Chem. 1970, 35, 2901-2904.
77. Chawla, H.M.; Chibber, S.S. Biologically Patterned Sensitized Photooxygenation of Chalcones. Tetrahedron Lett. 1976, 25, 2171-2172.
78. Kearns, D.R.; Hollins, R.A.; Khan, A.U.; Chambers, R.W.; Radlick, P. Evidence for the Participation of 1G+ and 1.DELTA.g Oxygen in Dye-sensitized Photooxygenation reactions. II. J. Am. Chem. Soc. 1967, 89, 5456-5457.
79. Chawla, H.M.; Chibber, S.S.; Sharma, A. Novel Photochemical Conversion of Chalcones to Flavanonols. Tetrahedron Lett. 1978, 30, 2713-2714.
80. Climent, M.J.; García, H.; Iborra, S.; Miranda, M.A.; Primo, J. Photosensitized Dehydrogenation of Flavanones to Flavones Using 2,4,6-Triphenylpyrylium tetrafluoroborate (TPT). Heterocycles 1989, 29, 115-121.
81. Badforss, S. Über die Einwirkung des Lichts auf Ketoxidovebindungen. Chem. Ber. 1918, 51, 214-219.
82. Zimmerman, H.E.; Cowley, B.R.; Tseng, C.Y; Wilson, J.W. A General Theory of Photochemical Reactions. VII. Mechanisms of Epoxy Reactions. J. Am. Chem. Soc. 1964, 86, 947-948.
83. Ramakrishnan, V.T.; Kagan, J. The Photochemical Conversion of Phenyl Epoxycinnamate to Flavonoids and Synthesis of 2′-Hydroxyepoxychalcone. J. Org. Chem. 1970, 35, 2898-2900.
84. Van der Westhuizen, J.H.; Ferreira, D.; Roux, D.G. Some Novel Photochemical and Related Aryl Couplings and Migrations in Flavonoid Synthesis. J. Chem. Soc., Perkin Trans. I 1980, 2856-2865.
85. Jeger, O.; Schafner, K.; Wehrli, H. Photochemical Transformation of α,α-Epoxyketones and Related Carbonyl Systems. Pure Appl. Chem. 1964, 9, 555-565.
86. Fourie, T.G.; Ferreira, D.; Roux, D.G. Flavonoid Synthesis based on Photolysis of Flavan-3-ols, 3-Hydroxyflavanones, and 2-Benzylbenzofuranones. J. Chem. Soc., Perkin Trans. I 1977, 2125-2133
87. Van der Westhuizen, J.H.; Ferreira, D.; Roux, D.G. Photochemical Deoxygenation of an α-Ketol: The Dihydroflavonol-Flavanone Conversion. J. Chem. Soc., Perkin Trans. I 1980, 1003-1006.
88. Van der Westhuizen, J.H.; Ferreira, D.; Roux, D.G. A Novel Photochemical Structural Inversion: The first Methoxy-hydroxymethyl Isomerization. J. Chem. Soc., Perkin Trans. I 1980, 1540-1543.
89. Van der Westhuizen, J.H.; Ferreira, D.; Roux, D.G. Photochemical Equivalent of Benzilic Acid Rearrangement and Related Conversions. J. Chem. Soc., Perkin Trans. I 1977, 1517-1522.
90. Turro, N.J. Modern Molecular Photochemistry; Benjamin/Cummings Publishing Co.: Menlo Park, CA, USA, 1978; p. 377.
91. Van der Westhuizen, J.H.; Ferreira, D.; Roux, D.G. Synthesis of Condensed Tannins. Part 2. Synthesis by Photolytic Rearrangement, Stereochemistry, and Circular Dichroism of the First 2,3-cis-3,4-cis-4-Arykflavan-3-ols. J. Chem. Soc., Perkin Trans. I 1981, 1220-1226.
92. Grover, P.K.; Anand, N. Photochemical Rearrangement of 4-Phenyl-3-chromanone. Chem. Commun. 1969, 982.
93. Padwa, A.; Lee, G.A. Involvement of an Enol Tautomer in the Photoisomerization of 4-Phenyl-3-chromonone to 4-Phenyldihydrocoumarin. J. Am. Chem. Soc. 1974, 96, 1634-1636.
94. Padwa, A.; Au, A. Tautomeric Control of the Photochemistry of 4-Phenylchroman-3-one. J. Chem. Soc., Chem. Commun. 1975, 58-59.
95. Padwa, A.; Au, A.; Owens, W. Photochemistry of the Chroman and 3-Chromanone Ring Systems. An Example of Tautomeric Control of Excited-State Chemistry. J. Org. Chem. 1978, 43, 303-310.
96. Yokoe, I.; Higushi, K.; Shirataki, Y.; Komatsu, M. Photochemistry of Flavonoids. V. Photocyclization of 2-Styryl-4H-chromen-4-ones. Chem. Pharm. Bull. 1981, 29, 2670-2674.
97. Kamboj, R.C.; Berar, S.; Berar, U.; Thakur, M., Gupta, S.C. Phototransformations of some 3-Alkoxy-6-chloro-2-{(E)-1′-methyl-2′- phenylvinyl}chromones: A study of Type-II and Triene Bichromophoric System. J. Photochem. Photobiol. A: Chem. 2009, 204, 122-128.
98. Dhande, V.P.; Thakwani, P.; Marathe, K.G. Flavonoid Part 7: A Novel Photosythesis of 3α-Hydroxybenzylflavones from 3-Arylideneflavanones. Tetrahedron 1988, 44, 3015-3023.
99. Ishibe, N.; Yutaka, S.; Masui, J.; Ishida, Y. Photorearrangement of Isoflavones. J. Chem. Soc., Chem. Commun. 1975, 241.
100. Griesbeck, A.G.; Mattay, J. Synthetic Organic Photochemistry. In Molecular and Supramolecular Photochemsitry; Ramamurthy, V., Schanze, K.S., Eds.; Marcel-Dekker: New York, NY, USA, 2005; Volume 12.
101. Grotewold, E. The Science of Flavonoids; Springer: New York, NY, USA, 2006.
102. Inoue, Y.; Ramamurthy, V. Chiral Photochemistry. In Molecular and Supramolecular Photochemsitry; Ramamurthy, V., Schanze, K.S., Eds.; Marcel-Dekker: New York, NY, USA, 2004; Volume 11.