Bi-, tri-, tetra-, penta-, and hexaflavonoids

Flavonoids: Chemistry, Biochemistry and Applications

Volumn , Issue , 2005, Pages 1101-1133

  Ferreira, Daneel ^a   Slade, Desmond ^a   Marais, Jannie P J ^a  

^a UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85056430876     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9781420039443     Document Type: Chapter

References (114)

1. Baker, W. and Ollis, W.D., Biflavonyls, in Recent Developments in the Chemistry of Natural Phenolic Compounds, Ollis, W.D., Ed., Pergamon, London, 1961, 152-184.
2. Locksley, H.D., The chemistry of biflavonoid compounds, Fortschr. Chem. Org. Naturst., 30, 207, 1973.
3. Geiger, H. and Quinn, C., Biflavonoids, in The Flavonoids, Harborne, J.B., Mabry, T.J., and Mabry, H., Eds., Chapman & Hall, London, 1975, 692-742.
4. Geiger, H. and Quinn, C., Biflavonoids, in The Flavonoids, Harborne, J.B. and Mabry, T.J., Eds., Chapman & Hall, London, 1982, 505-534.
5. Geiger, H. and Quinn, C., Biflavonoids, in The Flavonoids: Advances in Research Since 1980, Harborne, J.B. and Mabry, T.J., Eds., Chapman & Hall, London, 1988, 99-124.
6. Hemingway, R.W., Biflavonoids and proanthocyanidins, in Natural Products of Woody Plants 1: Chemicals Extraneous to the Lignocellulosic Cell Wall, Rowe, J.W., Ed., Springer Verlag, New York, 1989, 571-651.
7. Geiger, H., Biflavonoids and triflavonoids, in The Flavonoids: Advances in Research Since 1986, Harborne, J.B., Ed., Chapman & Hall, London, 1994, 95-115.
8. Taylor, W.I. and Battersby, A.R., Oxidative Coupling of Phenols, Marcel Dekker, New York, 1967.
9. Meselhy, M.R., Constituents from Moghat, the roots of Glossostemon bruguieri (Desf.), Molecules, 8, 614, 2003.
10. Lin, L-C. and Chou, C-J., Three new biflavonoids from Selaginella delicatula, Chin. Pharm. J., 52, 211, 2000.
11. Lin, L-C., Kuo, Y-C., and Chou, C-J., Cytotoxic biflavonoids from Selaginella delicatula, J. Nat. Prod., 63, 627, 2000.
12. Mitsuyoshi, S. et al., A new class of biflavonoids: 2'-hydroxygenistein dimers from the roots of white lupin, Z. Naturforsch., 55, 165, 2000.
13. Tang, S. et al., Biflavonoids with cytotoxic and antibacterial activity from Ochna macrocalyx, Planta Med., 69, 247, 2003.
14. De Oliveira, M.C.C. et al., New biflavonoid and other constituents from Luxemburgia nobilis (EICHL), J. Braz. Chem. Soc., 13, 119, 2002.
15. He., K. et al., A biflavonoid from Dysoxylum lenticellare, Phytochemistry, 42, 1199, 1996.
16. Pegnyemb, D.E. et al., Isolation and structure elucidation of a new isobiflavonoid from Ochna afzelii, Pharm. Biol., 41, 92, 2003.
17. Geiger, H. et al., Cyclobartramiatriluteolin, a unique triflavonoid from Bartramia stricta, Phytochemistry, 39, 465, 1995.
18. Murthy, S.S.S., Naturally occurring biflavonoid derivatives. 11. New biflavonoid from Semecarpus anacardium Linn., Chim. Act. Turc., 20, 33, 1992.
19. Goh, S.H. et al., Neoflavonoid and biflavonoid constituents from Calophyllum inophylloide, J. Nat. Prod., 55, 1415, 1992.
20. Cao, S-G., Sim, K-Y., and Goh, S-H., Minor methylated pyranoamentoflavones from Calophyllum venulosum, Nat. Prod. Lett., 15, 291, 2001.
21. Cao, S-G., Sim, K-Y., and Goh, S-H., Biflavonoids of Calophyllum venulosum, J. Nat. Prod., 60, 1245, 1997.
22. Reddy, B.P. and Krupadanam, G.L.D., Chemical constituents of the leaves of Himalayan Taxus baccata: use of DQF-COSY in the structure elucidation of biflavones, Indian J. Chem., 35B, 283, 1996.
23. Ahmed, M.S. et al., A weakly antimalarial biflavanone from Rhus retinorrhoea, Phytochemistry, 58, 599, 2001.
24. Hahn, H. et al., The first biaurone, a triflavone and biflavonoids from two Aulacomnium species, Phytochemistry, 40, 573, 1995.
25. D’arc Felicio, J. et al., Biflavonoids from Ouratea multiflora, Fitoterapia, 72, 453, 2001.
26. Velandia, J.R. et al., Biflavonoids and a glucopyranoside derivative from Ouratea semiserrata, Phytochem. Anal., 13, 283, 2002.
27. Jiang, Z-H. et al., Biflavanones, diterpenes, and coumarins from the roots of Stellera chamaejasme L., Chem. Pharm. Bull., 50, 137, 2002.
28. D’arc Felicio, J. et al., Inhibition of lens aldose reductase by biflavones from Ouratea spectabilis, Planta Med., 61, 217, 1995.
29. Nishimura, S. et al., Structures of 4-arylcoumarin (neoflavone) dimers isolated from Pistacia chinensis Bunge and their estrogen-like activity, Chem. Pharm. Bull., 48, 505, 2000.
30. Moreira, I.C. et al., Isoflavanone dimers hexaspermone A, B and C from Ouratea hexasperma, Phytochemistry, 35, 1567, 1994.
31. Marston, A., Slacamin, I., and Hostettmann, K., Antifungal polyphenols from Cordia goetzei Guerke, Helv. Chim. Acta, 71, 1210, 1988.
32. Messanga, B. et al., Biflavonoids from Ochna calodendron, Phytochemistry, 35, 791, 1994.
33. Moreira, I.C. et al., A flavone dimer from Ouratea hexasperma, Phytochemistry, 51, 833, 1999.
34. Sievers, H. et al., Further biflavonoids and 3'-phenylflavonoids from Hypnum cupressiforme, Phytochemistry, 35, 795, 1994.
35. Bekker, R., Brandt, E.V., and Ferreira, D., Structure and stereochemistry of the first isoflavanone-benzofuranone biflavonoids, Tetrahedron Lett., 39, 6407, 1998.
36. Bekker, R., Brandt, E.V., and Ferreira, D., Biflavonoids. Part 4. Structure and stereochemistry of novel flavanone- and the first isoflavanone-benzofuranone biflavonoids, Tetrahedron, 55, 10005, 1999.
37. Bekker, R., Brandt, E.V., and Ferreira, D., Absolute configuration of flavanone-benzofuranonetype biflavonoids and 2-benzyl-2-hydroxybenzofuranones, J. Chem. Soc. Perkin Trans., 1, 2535, 1996.
38. Bekker, R. et al., Biflavonoids. Part 5: structure and stereochemistry of the first bibenzofuranoids, Tetrahedron, 56, 5297, 2000.
39. Rani, M.S. et al., A biflavonoid from Cycas beddomei, Phytochemistry, 47, 319, 1998.
40. Seeger, T. et al., Biflavonoids from the moss, Homalothecium lutescens, Phytochemistry, 34, 295, 1993.
41. Roitman, J.N., Wong, R.Y., and Wollenweber, E., Methylene bisflavonoids from frond exudates of Pentagramma triangularis ssp triangularis, Phytochemistry, 34, 297, 1993.
42. Messanga, B.B. et al., Calodenone, a new isobiflavonoid from Ochna calodendron, J. Nat Prod., 55, 245, 1992.
43. Iinuma, M. et al., Two biflavonoids in the farinose exudate of Pentagramma triangularis, Phytochemistry, 35, 1043, 1994.
44. Li, S-H. et al., Chemical constituents from Amentotaxus yunnanensis and Torreya yunnanensis, J. Nat. Prod., 66, 1002, 2003.
45. Carneiro, F.J.C. et al., Bi- and tetraflavonoids from Aristolochia ridicula, Phytochemistry, 55, 823, 2000.
46. Tih, A.E. et al., A novel hexaflavonoid from Lophira alata, Tetrahedron Lett., 40, 4721, 1999.
47. Tih, A.E. et al., Lophiroflavans B and C, tetraflavonoids of Lophira alata, Phytochemistry, 31, 3595, 1992.
48. Tih, R.G., Tih, A.E., and Sondengam, B.L., Structures of lophirones I and J, minor cleaved chalcone dimers of Lophira lanceolata, J. Nat. Prod., 57, 142, 1994.
49. Tih, A. et al., Tetraflavonoids of Lophira alata, Phytochemistry, 31, 981, 1992.
50. Murakami, A. et al., Possible antitumor promoters: bi- and tetraflavonoids from Lophira alata, Phytochemistry, 31, 2689, 1992.
51. Murakami, A. et al., Chalcone tetramers, lophirachalcone and alatachalcone from Lophira alata as possible antitumor promoters, Biosci. Biotechnol. Biochem., 56, 769, 1992.
52. Kaewamatawong, R. et al., Novel biflavonoids from the stem bark of Ochna integerrima, J. Nat. Prod., 65, 1027, 2002.
53. Ramírez, I. et al., Cissampeloflavone, a chalcone-flavone dimer from Cissampelos pareira, Phytochemistry, 64, 645, 2003.
54. Iinuma, M. et al., Unusual biflavonoids in the farinose exudate of Pentagramma triangularis, Phytochemistry, 44, 705, 1997.
55. Seeger, T. et al., Isomeric triluteolins from Bartramia stricta and Bartramia pomiformis, Phytochemistry, 40, 1531, 1995.
56. Asada, Y., Li, W., and Yoshikawa, T., The first prenylated biaurone, licoagrone from hairy root cultures of Glycyrrhiza glabra, Phytochemistry, 50, 1015, 1999.
57. Westenburg, H.E. et al., Activity-guided isolation of antioxidative constituents of Cotinus coggygria, J. Nat. Prod., 63, 1696, 2000.
58. Masesane, I.B. et al., A bichalcone from the twigs of Rhus pyroides, Phytochemistry, 53, 1005, 2000.
59. Tih, A.E. et al., Bongosin: a new chalcone-dimer from Lophira alata, J. Nat. Prod., 53, 964, 1990.
60. Messanga, B.L. et al., Isolation and structure elucidation of a new pentaflavonoid from Ochna calodendron, New J. Chem., 25, 1098, 2001.
61. Tih, A.E. et al., A new chalcone dimer from Lophira alata, Tetrahedron Lett., 29, 5797, 1988.
62. Tih, R.G. et al., Structures of isombamichalcone and lophirochalcone, bi- and tetraflavonoids from Lophira lanceolata, Tetrahedron Lett., 30, 1807, 1989.
63. Pegnyemb, D.E. et al., Flavonoids of Ochna afzelii, Phytochemistry, 64, 661, 2003.
64. Mbing, J.N. et al., Two biflavonoids from Ouratea flava stem bark, Phytochemistry, 63, 427, 2003.
65. Ghogomu, R. et al., Lopirone A, a biflavonoid with unusual skeleton from Lophira lanceolata, Tetrahedron Lett., 28, 2967, 1987.
66. Pegnyemb, D.E. et al., Biflavonoids from Ochna afzelii, Phytochemistry, 57, 579, 2001.
67. Mdee, L.K., Yeboah, S.O., and Abegaz, B.M., Rhuschalcones II-VI, five new bichalcones from the root bark of Rhus pyroides, J. Nat. Prod., 66, 599, 2003.
68. Bai, H. et al., A novel biflavonoid from roots of Glycyrrhiza uralensis cultivated in China, Chem. Pharm. Bull., 51, 1095, 2003.
69. Terashima, K., Aqil, M., and Niwa, M., Garcinianin, a novel biflavonoid from the roots of Garcinia kola, Heterocycles, 41, 2245, 1995.
70. Cechinel Filho, V. et al., I3-naringenin-II8-4'-OMe-eriodyctol: a new potential analgesic agent isolated from Rheedia gardneriana leaves, Z. Naturforsch., 55, 820, 2000.
71. Brinkmeier, E. et al., The cooccurrence of different biflavonoid types in Pilotrichella flexilis, Z. Naturforsch., 55, 866, 2000.
72. Terashima, K., A study of biflavanones from the stems of Garcinia kola (Guttiferae), Heterocycles, 50, 283, 1999.
73. Ito, C. et al., A new biflavonoid from Calophyllum panciflorum with antitumor-promoting activity, J. Nat. Prod., 62, 1668, 1999.
74. Ferrari, J. et al., Isolation and on-line LC/CD analysis of 3,8''-linked biflavonoids from Gnidia involucrate, Helv. Chim. Acta, 86, 2768, 2003.
75. Rao, K.V. et al., Two new biflavonoids from Ochna obtusata, J. Nat. Prod., 60, 632, 1997.
76. Jayaprakasam, B. et al., 7-O-methyltetrahydroochnaflavone, a new biflavanone from Ochna beddomei, J. Nat. Prod., 63, 507, 2000.
77. Likhitwitayawuid, K. et al., Flavonoids from Ochna integerrima, Phytochemistry, 56, 353, 2001.
78. Jayakrishna, G. et al., A new biflavonoid from Ochna beddomei, J. Asian Nat. Prod. Res., 5, 83, 2003.
79. Ariyasena, J. et al., Ether-linked biflavonoids from Quintinia acutifolia, J. Nat. Prod., 67, 693, 2004.
80. Jayaprakasam, B. et al., A biflavanone from Cycas beddomei, Phytochemistry, 53, 515, 2000.
81. Xu, Z. et al., New biflavanones and bioactive compounds from Stellera chamaejasme, Yaoxue Xuebao, 36, 668, 2001.
82. Baba, K., Taniguchi, M., and Kozawa, M., Three biflavonoids from Wikstroemia sikokiana, Phytochemistry, 37, 879, 1994.
83. Pegnyemb, D.E., Ghogomu-Tih, R., and Sondengam, B.L., Minor biflavonoids from Lophira lanceolata, J. Nat. Prod., 57, 1275, 1994.
84. Si, D. et al., Biflavonoids from the aerial parts of Stephania tetrandra, Phytochemistry, 58, 563, 2001.
85. Rampendahl, C. et al., The biflavonoids of Plagiomnium undulatum, Phytochemistry, 41, 1621, 1996.
86. Geiger, H. and Seeger, T., Triflavones and a biflavone from the moss Rhizogonium distichum, Z. Naturforsch., 55, 870, 2000.
87. Brinkmeier, E., Geiger, H., and Zinsmeister, D., Biflavonoids and 4,2'-epoxy-3-phenylcoumarins from the moss Mnium hornum, Phytochemistry, 52, 297, 1999.
88. Li, W., Asada, Y., and Yoshikawa, T., Flavonoid constituents from Glycyrrhiza glabra hairy root cultures, Phytochemistry, 55, 447, 2000.
89. Muhaisen, H.M. et al., Flavonoid from Viburnum cotinifolium, J. Chem. Res. (S), 480, 2002.
90. Lin, Y-M. et al., In vitro anti-HIV activity of biflavonoids isolated from Rhus succedanea and Garcinia multiflora, J. Nat. Prod., 60, 884, 1997.
91. Donnelly, D.M.X., Fitzpatrick, B.M., and Finet, J-P., Aryllead triacetates as synthons for the synthesis of biflavonoids. Part 1. Synthesis and reactivity of a flavonyllead triacetate, J. Chem. Soc., Perkin Trans. 1, 1791, 1994.
92. Donnelly, D.M.X. et al., Aryllead triacetates as synthons for the synthesis of biflavonoids. Part 2. Synthesis of a garcinia-type biflavonoid, J. Chem. Soc., Perkin Trans. 1, 1797, 1994.
93. Shimamura, T. et al., Biogenetic synthesis of biflavonoids, lophirones B and C, from Lophira lanceolata, Heterocycles, 43, 2223, 1996.
94. 1H-NMR spectra of the biflavones isocryptomerin and cryptomerin B. A critical comment on two recent publications on the biflavone patterns of Selaginella selaginoides and S. denticulate, Z. Natursforsch., 51, 757, 1996.
95. 1H-NMR assignments in biflavonoid spectra by proton-detected C-H correlation, Z. Natursforsch., 48, 821, 1993.
96. Zhao, L-Y. et al., Total synthesis of several 8,8''-biflavones, Chin. Chem. Lett., 9, 351, 1998.
97. Nunome, S. et al., In vitro antimalarial activity of biflavonoids from Wikstroemia indica, Planta Med., 70, 76, 2004.
98. Jiang, R-W. et al., Molecular structures and p-p interactions in some flavonoids and biflavonoids, J. Mol. Struct., 642, 77, 2002.
99. Zembower, D.E. and Zhang, H., Total synthesis of robustaflavone, a potential anti-hepatitis B agent, J. Org. Chem., 63, 9300, 1998.
100. Majinda, R.R.T. et al., Phenolic and antibacterial constituents of Vahlia capensis, Planta Med., 63, 268, 1997.
101. Dumontet, V. et al., New cytotoxic flavonoids from Cryptocarya infectoria, Tetrahedron, 57, 6189, 2001.
102. Wall, M.E. et al., Plant antitumor agents. 31. The calycopterones, a new class of biflavonoids with novel cytotoxicity in a diverse panel of human tumor cell lines, J. Med. Chem., 37, 1465, 1994.
103. Mayer, R., Calycopterones and calyflorenones, novel biflavonoids from Calycopteris floribunda, J. Nat. Prod., 62, 1274, 1999.
104. Mayer, R., Five biflavonoids from Calycopteris floribunda (Combretaceae), Phytochemistry, 65, 593, 2004.
105. Abegaz, B.N. et al., Chalcones and other constituents of Dorstenia prorepens and Dorstenia zenkeri, Phytochemistry, 59, 877, 2002.
106. Wang, L-W. et al., New alkaloids and a tetraflavonoid from Cephalotaxus wilsoniana, J. Nat. Prod., 67, 1182, 2004.
107. Yadav, S. and Bhadoria, B.K., Novel biflavonoids from the leaves of Leucaena diversifolia and Albizia procera and their protein binding efficiency, J. Indian Chem. Soc., 81, 392, 2004.
108. Parveem, M. et al., A new biflavonoid from leaves of Garcinia nervosa, Nat. Prod. Res., 18, 269, 2004.
109. Nunome, S. et al., In vitro antimalarial activity of biflavonoids from Wikstroemia indica, Planta Med., 70, 76, 2004.
110. Gaffield, W., Circular dichroism, optically rotatory dispersion and absolute configuration of flavanones, 3-hydroxyflavanones and their glycosides. Determination of agyclone chirality in flavanone glycosides, Tetrahedron, 26, 4093, 1970.
111. 13C-NMR and CD of some 3,8''-biflavonoids from Garcinia species and of related flavanones, Phytochemistry, 17, 1369, 1978.
112. Li, X-C. et al., Absolute configuration, conformation, and chiral properties of flavanone-(3!8'')-flavone biflavonoids from Rheedia acuminata, Tetrahedron, 58, 8709, 2002.
113. Slade, D., Ferreira, D., and Marais, J.P.J., Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids, Phytochemistry, 2005, in press.
114. Bekker, R. et al., Resolution and absolute configuration of naturally occurring auronols, J. Nat. Prod., 64, 345, 2001.