Flavans and proanthocyanidins

The Flavonoids: Advances in Research since 1986

Volumn , Issue , 2017, Pages 23-56

  Porter, Lawrence J ^a  

^a New Zealand Department of Scientific and Industrial Research   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

TANNINS;

CONDENSED TANNINS; FLAVONOID; NATURAL PRODUCTS; NATURAL PRODUCTS CHEMISTRY; PROANTHOCYANIDINS;

FLAVONOIDS;

EID: 85052890784     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9780203736692     Document Type: Chapter

References (118)

1. Agrawal, P.K., Bansal, M.C., Porter, L.J. and Foo, L.Y. (1989), in Carbon-13 NMR of Flavonoids (ed. P.K. Agrawal), Elsevier. Amsterdam, p. 432.
2. Baba, K., Takeuchi. K., Doi, M., Inoue, M. and Kozawa. M. (1986), Chem. Pharm. Bull. 34, 1540.
3. Baba, K., Takeuchi, K., Doi, M., Inoue, M. and Kozawa, M. (1987), Chem. Pharm. Bull. 35, 1853.
4. Balde, A.M., Pieters, L.A., Gergely, A., Kolodziej, H., Claeys, M. and Vlietinck, A.J. (1991), Phytochemistry 30, 337.
5. Barn, M., Malan, J.C.S., Young, D.A., Brandt, E.V. and Ferreira, D. (1990), Phytochhemistry 29, 283.
6. Bergmann, W.R., Barkley, M.D., Herningway, R.W. and Mattice, W.L. (1987), J. Am. Chem. Soc. 109, 6614.
7. Bonefeld, M., Friedrich, H. and Kolodziej, H. (1986), Phytochemistry 25, 1205.
8. Brandt, E.V., Ferreira, D. and Roux, D.G. (1981), J. Chem. Soc., Perkin Trans. 1, 1879.
9. Brandt, E.V., Young, D.A., Young, E. and Ferreira, D. (1987), J. Chem. Soc., Perkin Trans. 11, 1365.
10. Brieskorn, C.H. and Betz, R. (1988), Z. Lebensm.-Unters. Forsch. 187, 347.
11. Burger, J.F.W., Steynberg, J.P., Young, D.A., Brandt, E.V. and Ferreira, D. (1989), J. Chem. Soc., Perkin Trans. 1, 671.
12. Burger, J. F. W., Kolodzie J, H., Herningway, R. W., Steynberg, J.P., Young, D.A. and Ferreira, D. (1990), Tetrahedron 46, 5733.
13. Cronje, A., Burger, J.F.W., Brandt, E. V., Kolodziej, H. and Ferreira, D. (1990), Tetrahedron Lett. 31, 3789.
14. da Silva, J.M.R., Rigaud, J., Cheynier, V., Cheminat, A. and Moutounet, J. (1991), Phytochemistry 30, 1259.
15. Delcour, J.A. and Tuytens, G.M. (1984), J. Inst. Brew. 90, 153.
16. DelleMonache, F., Labbiento, L., Marta, M. and Lwande, W. (1986), Phytochemistry 25, 1711.
17. Diaz Diaz, P.P. and De Diaz, A.M.P. (1986), Phytochemistry 25, 2395.
18. Drewes, S.E. and Illsley, A.H. (1969), J. Chem. Soc. (C) 897.
19. Fletcher, A.C., Porter. L.J., Haslam, E. and Gupta, R.K. (1977), J. Chem. Soc., Perkin Trans. II 11628.
20. Foo, L.Y. (1987), Phytochemistry 26, 2825.
21. Foo, L.Y. (1989a), J. Chem. Soc., Chem. Commun 1505.
22. Foo, L.Y. (1989b), Phytochemistry 28, 2477.
23. Foo, L.Y. and Karchesy, J.J. (1989), Phytochemistry 28, 3185.
24. Foo, L. Y. and Karchesy, J.J. (1991), Phytochemistry 30, 667.
25. Foo, L.Y. and Porter, L.J. (1983), J. Chem. Soc., Perkin Trans. 1, 1535.
26. Foo, L.Y. and Wong, H. (1986), Phytochemistry 25, 1961.
27. Gaffield, W., Foo, L.Y. and Porter, L.J. (1989), J. Chem. Res. (S) 144.
28. Gomez-Garibay, F., Guijano, L., Calderon, J.S., Morales, S. and Rios, T. (1988), Phytochemistry 27, 2971.
29. Hashimoto, F., Nonaka, G. and Nishioka, I. (1987), Chem. Pharm. Bull. 35, 611.
30. Hashimoto, F., Nonaka, G. and Nishioka, I. (1988), Chem. Pharm. Bull. 36, 1676.
31. Hashimoto, F., Nonaka, G. and Nishioka, I. (1989), Chem. Pharm. Bull. 37, 3255.
32. Haslam, E. (1975), in The Flavonoids (eds J.B. Harborne, T.J. Mabry and H. Mabry), Chaprnan and Hall, London.
33. Haslarn, E. (1982), in The Flavonoids: Advances in Research (eds J.B. Harborne and T.J. Mabry), Chapman and Hall, London.
34. Haslam, E. (1989), Plant Polyphenols. Vegetable Tannins Revisited, Cambridge University Press, Cambridge.
35. Hatano, T., Shida, S., Han, L. and Okuda, T. (1991), Chem. Pharm. Bull. 39, 876.
36. Hemingway, R.W. (1989), in The Natural Products of Woody Plants I (ed. J.W. Rowe), Springer, Berlin, p. 571.
37. Herningway, R.W. and Karchesy, J.J. (eds) (1989), Chemistry and Significance of Condensed Tannins, Plenum, New York.
38. Herningway, R.W. and Porter, L.J. (1989), in The Natural Products of Woody Plants ll (ed. J.W. Rowe), Springer, Berlin, p. 651.
39. Herningway, R.W., Foo, L.Y. and Porter, L.J. (1982), J. Chem. Soc., Perkin Trans. I 1209.
40. Herz, W. and Bruno, M. (1987), Phytochemistry 26, 1175.
41. Hori, K., Satake, T., Saiki, Y., Murakami, T. and Chen, C. (1988), Chem. Pharm. Bull. 36, 4301.
42. Hwang, T., Kashiwada, Y., Nonaka, G. and Nishioka, I. (1990), Phytochemistry 29, 279.
43. Ikeya, Y., Taguchi, H., Yoshioka, I. and Kobayashi, H. (1979), Chem. Pharm. Bull. 27, 1383.
44. Ikuta, J., Hano, Y., Nomura, T., Kawakarni, Y. and Sato, T. (1986), Chem. Pharm. Bull. 34, 1968.
45. Ishimaru, K., Nonaka, G. and Nishioka, I. (1987a), Chem. Pharm. Bull. 35, 602.
46. Ishimaru, K., Nonaka, G. and Nishioka, I. (1987b), Phytochemistry 26, 1167.
47. Ishirnaru, K., Ishirnatsu, M., Nonaka, G., Mihashi, K., Iwase, Y. and Nishioka, I. (1988), Chem. Pharm. Bull. 36, 3319.
48. IUPAC (1979), Nomenclature of Organic Chemistry, Pergarnon, Oxford.
49. Jacques, D., Opie, C.T., Porter, L.J. and Haslam, E. (1977), J. Chem. Soc., Perkin Trans. 1, 1637.
50. Karchesy, J.J. and Herningway, R.W. (1986), J. Agric. Food Chem. 34, 966.
51. Karchesy, J.J., Herningway, R.W., Foo, L.Y., Barofsky, E. and Barofsky, D.F. (1986), Anal. Chem. 58, 2563.
52. Karchesy, J.J., Foo, L.Y., Barofsky, E., Arbogast, B. and Barofsky, D.F. (1989), J. Wood Chem. Technol. 9, 313.
53. Kardono, L.B.S., Tsauri, S., Padmawinata, K. and Kinghorn, A. D. (1990), Phytochemistry 29, 2995.
54. Kashiwada, Y., Nonaka, G. and Nishioka, I. (1986a), Chem. Pharm. Bull. 34, 3208.
55. Kashiwada. Y., Nonaka, G. and Nishioka, I. (1986b), Chem. Pharm. Bull. 34, 4083.
56. Kashiwada, Y., Morita, M., Nonaka, G. and Nishioka, L (1990a), Chem. Pharm. Bull. 38, 856.
57. Kashiwada, Y., Iizuka, H., Yoshioka, K., Chen, R., Nonaka, G. and Nishioka, I. (1990b), Chem. Pharm. Bull. 38, 888.
58. Kennedy, J.A., Munro, M.H.G., Powell, H.K.J., Porter, L.J. and Foo, L.Y. (1984), Aust. J. Chem. 37, 885.
59. Kolodziej, H. (1987), J. Chem. Soc., Chem. Commun. 205.
60. Kolodziej, H. (1989), Phytochemistry 28, 3487.
61. Kolodziej, H. (1990a), Phytochemistry 29, 955.
62. Kolodziej, H. (1990b), Phytochemistry 29, 1671.
63. Kolodziej, H., Bonefeld, M., Burger, J.F.W., Brandt, E.V. and Ferreira D. (1991a), Phytochemistry 30, 1255.
64. Kolodziej, H., Sakar, M.K., Burger, J.F.W., Engelshowe, R. and Ferreira, D. (1991b), Phytochemistry 30, 2041.
65. Kubo, I., Kim, M. and Naoki, H. (1987), Tetrahedron Lett. 28, 921.
66. Lin, T., Tanaka, T., Nonaka, G., Nishioka, I. and Young, T. (1991), Chem. Pharm. Bull. 39, 1144.
67. Malan, E. and Ferreira, D. (1987), Phytochemistry 26, 2049.
68. Malan, E. and Roux, D.G. (1974), Phytochemistry 13, 1575.
69. Malan, J.C.S., Young, D.A., Steenkarnp, J.A. and Ferreira, D. (1988), J. Chem. Soc., Perkin Trans. 1, 2567.
70. Malan, J.C.S., Steynberg, P.J., Steynberg, J.P., Young, D.A., Bezuidenhoudt. B.C.B. and Ferreira, D. (1990a), Tetrahedron 46, 2883.
71. Malan, J.C.S., Steenkamp. J.A., Steynberg, J.P., Young, D.A., Brandt, E.V. and Ferreira, D. (1990b), J. Chem. Soc., Perkin Trans. I 209.
72. Malan, J.C.S., Young. D.A., Steynberg, J.A. and Ferreira, D. (1990c), J. Chem. Soc., Perkin Trans I 219.
73. Malan, J.C.S., Young, D.A., Steynberg, J.P. and Ferreira, D. (1990d), J. Chem. Soc., Perkin Trans. I 227.
74. Morgan, K.R. and Newman, R.H. (1987), APPITAJ. 40, 450.
75. Morimoto, S., Nonaka, G. and Nishioka, I. (1988a), Chem. Pharm. Bull. 36, 33.
76. Morimoto, S., Nonaka, G., Chen, R. and Nishioka, I. (1988b), Chem. Pharm. Bull. 36, 39.
77. Morimoto, S., Tanabe, H., Nonaka, G. and Nishioka, I. (1988c), Phytochemistry 21, 907.
78. Newman, R.H., Porter, L.J., Foo, L.Y., Johns, S.R. and Willing, R.I. (1987), Magn. Reson. Chem. 25, 118.
79. Nishimura, H., Nonaka, G. and Nishioka, I. (1986), Chem. Pharm. Bull. 34, 3223.
80. Nonaka, G., Nishioka, I., Nagasawa, T. and Oura, H. (1981), Chem. Pharm. Bull. 29, 2862.
81. Nonaka, G., Kawahara, O. and Nishioka, I. (1983), Chem. Pharm. Bull. 31, 3906.
82. Nonaka, G., Morimoto, S., Kinjo, J., Nohara, T. and Nishioka, I. (1987a), Chem. Pharm. Bull. 35, 149.
83. Nonaka, G., Goto, Y., Kinjo, J., Nohara, T. and Nishioka, I. (1987b), Chem. Pharm. Bull. 35, 1105.
84. Nonaka, G., Ishimaru, K., Mihashi. K., Iwasi, Y., Ageta, M. and Nishioka, l. (1988), Chem. Pharm. Bull. 36, 857.
85. Nunes. D.S., Haug, A. and Bestmann, H. (1989), Phytochemistry 28, 2183.
86. Okuda, T., Yoshida, T., Hatano, T., Yazaki, K., Ikegami. Y. and Shingu, T. (1987), Chem. Pharm. Bull. 35, 443.
87. Ozawa, T., Hiroto. M. and Imagawa, H. (1990), Agric. Biol. Chem. 54, 217.
88. Porter, L.J. (1974), NZJ Sci. 17, 213.
89. Porter, L.J. (1988), in The Flavonoids: Advances in Research since 1980 (ed. J.B. Harborne), Chapman and Hall, London, p. 21.
90. Porter, L.J. (1989), in The Natural Products of Woody Plants I(ed. J.W. Rowe). Springer, Berlin. p. 651.
91. Porter, L.J., Wong, R.Y., Benson, M., Chan. B.O., Viswanadhan. V.N., Gandour, R.D. and Mattice, W.L. (1986), J. Chem. Res. (S) 86; J. Chem. Res. (M) 0830.
92. Porter, L.J., Ma. Z. and Chan, B.O. (1991), Phytochemistry 30, 1657.
93. Stafford, H.A. (1988a), in Chemistry and Signzficance of Condensed Tannins (eds R. W. Hemingway and J.J. Karchesy), Plenum, New York, p. 301.
94. Stafford, H.A. (1988b), Phytochemistry 27, 1.
95. Stafford, H. A., Lester, H.H. and Weider, R.M. (1987), Plant Sci. 52, 99.
96. Steenkamp, J.A., Steynberg, J.P., Brandt, E. V., Ferreira, D. and Roux, D.G. (1985). J. Chem. Soc., Chem. Commun. 1678.
97. Steenkamp, J.A., Malan, J.C.S., Roux, D.G. and Ferreira, D. (1988a), J. Chem. Soc., Perkin Trans. I 1325.
98. Steenkamp, J.A., Malan, J.C.S. and Ferreira, D. (1988b), J. Chem. Soc., Perkin Trans. I 2179.
99. Sternhell, S. (1975), in Dynamic Nuclear Magnetic Resonance Spectroscopy (eds L.M. Jackman and F.A. Cotton), Academic Press, New York, p. 163.
100. Steynberg, J.P., Ferreira, D. and Roux, D.G. (1987), J. Chem. Soc., Perkin Trans. 11705.
101. Steynberg, J.P., Burger, J.F.W., Young, D.A., Brandt, E. V., Steenkamp, J.A. and Ferreira, D. (1988a), J. Chem. Soc., Perkin Trans. I 3323.
102. Steynberg, J.P., Burger. J.F.W., Young, D.A., Brandt, E. V., Steenkamp, J.A. and Ferreira, D. (1988b), J. Chem. Soc., Perkin Trans I 3331.
103. Steynberg, J.P., Steenkamp, J.A., Burger, J.F.W., Young, D.A. and Ferreira, D. (1990a). J. Chem. Soc., Perkin Trans. I 235.
104. Steynberg, J.P., Burger, J.F.W., Cronje, A., Bonnet, S.L., Malan, J.C.S., Young, D.A. and Ferreira, D. (1990b), J. Chem. Soc., Perkin Trans. I 2979.
105. Steynberg, J.P., Burger, J.F.W., Malan, J.C.S., Cronje, A., Young, D.A. and Ferreira, D. (1990c), Phytochemistry 29, 275.
106. Steynberg, J.P., Bezuidenhoudt. B.C.B., Burger, J.F.W., Young, D.A. and Ferreira. D. (1990d), J. Chem. Soc., Perkin Trans. I 203.
107. Sun. D., Wong, H. and Foo, L.Y. (1987), Phytochemistry 26, 1825.
108. Tanaka, N., Orii, R., Ogasa, K., Wada. H., Murakami. T. Saiki, Y. and Chen, C. (1991), Chem. Pharm. Bull. 39, 55.
109. Van Rooyen, P.H. and Redelinghuys, H.J.P. (1983), S. Afr. J. Chem. 36, 49.
110. Viswanadhan, V.N. and Mattice, W.L. (1986). J. Comput. Chem. 1, 711.
111. Viswanadhan, V. N. and Mattice, W.L. (1987), J. Chem. Soc., Per kin Trans. 11, 739.
112. Waterman, P.G. and Mahmoud. E. N. (1987), Phytochemistry 26, 1189.
113. Yazaki, K. and Okuda. T. (1990), Phytochemistry 29, 1559.
114. Young, D.A., Ferreira, D. and Roux, D.G. (1983), J. Chem. Soc., Per kin Trans. I 2031.
115. Young, D.A., Cronje, A., Botes, A.L., Ferreira. D. and Roux, D.G. (1985), J. Chem. Soc., Perkin Trans. I 2521.
116. Young, D.A., Young, E., Roux, D.G., Brandt, E.V. and Ferreira, D. (1987), J. Chem. Soc., Perkin Trans. I 2345.
117. Young, E., Brandl, E.V., Young, D.A., Ferreira, D. and Roux, D.G. (1986), J. Chem. Soc. Perkin Trans. I 1737.
118. Zhang. B., Nonaka, G. and Nishioka, I. (1988), Phytochemistry 27, 3277.