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Abstract

Recent advances in isolation and structure elucidation of several hundred of new polyphenolic compounds of the tannin class using new techniques (1) have altered the definition of a tannin, at least that of a hydrolyzable tannin. Thus the term tannin now includes all polyphenolic compounds of defined chemical structure as well as the whole group of compounds whose chemical structures and properties are those of tannins. Tannins by the new definition are thus similar to other classes of natural products, such as alkaloids, terpenoids etc.

Keywords

Ellagic Acid Rosmarinic Acid Hydrolyzable Tannin Centrifugal Partition Chromatography Galloyl Group 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Okuda, T., T. Yoshida, and T. Hatano: New Methods of Analyzing Tannins. J. Nat. Prod. 52, 1 (1989).Google Scholar
  2. 2.
    Haslam, E.: The Metabolism of Gallic Acid and Hexahydroxydiphenic Acid in Higher Plants. Fortschritte Chem. Org. Naturst. 41, 1 (1982).Google Scholar
  3. 3.
    Haslam, E.: Plant Polyphenols, Vegetable Tannins Revisited. Cambridge: Cambridge University Press. 1989.Google Scholar
  4. 4.
    Okuda, T., T. Yoshida, and T. Hatano: Oligomeric Hydrolyzable Tannins, a New Class of Plant Polyphenols. Heterocycles 30, 1995 (1990).Google Scholar
  5. 5.
    Okuda, T., T. Yoshida, T. Hatano, M. Kubo, T. Orime, M. Yoshizaki, and N. Naruhashi: Hydrolysable Tannins as Chemotaxonomic Markers in the Rosaceae. Phytochem. 31, 3091 (1992).Google Scholar
  6. 6.
    Okuda, T., T. Yoshida, and T. Hatano: Classification of Oligomeric Hydrolyzable Tannins and Specificity of Their Occurrence in Plants. Phytochem. 32, 507 (1993).Google Scholar
  7. 7.
    Okuda, T., T. Yoshida, and T. Hatano: Chemistry and Biological Activities of Tannins in Medicinal Plants. In: Economic and Medicinal Plant Research, Vol. V (H. Wagner and N. R. Farnsworth, eds.), p. 129. London, New York: Academic Press. 1991.Google Scholar
  8. 8.
    Okuda, T., T. Yoshida, and T. Hatano: Ellagitannins as Active Constituents of Medicinal Plants. Planta Med. 55, 117 (1989).Google Scholar
  9. 9.
    Okuda, T., T. Yoshida, and T. Hatano: Pharmacologically Active Tannins Isolated from Medicinal Plants. In: Plant Polyphenols, Synthesis, Properties, Significance (R. W. Hemingway and P. E. Laks, eds.), p. 539. New York: Plenum Press. 1992.Google Scholar
  10. 10.
    Gross, G.G.: Enzymatic Synthesis of Gallotannins and Related Compounds. In: Phenolic Metabolism in Plants (H.A. Stafford and R.K. Ibrahim, eds.), p. 297. New York: Plenum Press. 1992.Google Scholar
  11. 11.
    Schmidt, O.Th., and G. Klinger: Über natürliche Gerbstoffe, XXYIII: Synthese der 1,3,6-Trigalloylglucose. Liebigs Ann. Chem. 609, 199 (1957).Google Scholar
  12. 12.
    Haddock, E. A., R. K. Gupta, S. M. K. Al-Shafi, K. Layden, E. Haslam, and D. Magnolato: The Metabolism of Gallic Acid and Hexahydroxydiphenic Acid in Plants: Biogenetic and Molecular Taxonomic Considerations. Phytochem. 21, 1049 (1982).Google Scholar
  13. 13.
    Armitage, R., G. S. Bayliss, J.W. Gramshaw, E. Haslam, H. J. R. D. Haworth, K. Jones, H. J. Rogers, and T. Searle: Gallotannins, Part III: The Constitution of Chinese, Turkish, Sumach, and Tara Tannins. J. Chem. Soc. 1961, 1842.Google Scholar
  14. 14.
    Delahaye, P., A. De Bruyn, F. Van Damme, and M. Verzele: Trigallic Acid or Trimeric Gallic Acid. Bull. Soc. Chim. Belg. 92, 469 (1983).Google Scholar
  15. 15.
    Mayer, W., N. Kunz, and F. Loebich: Die Struktur Hamamelitannins. Liebigs Ann. Chem. 688, 232 (1965).Google Scholar
  16. 16.
    Ozawa, T., S. Kobayashi, R. Seki, and H. Imagawa: A New Gallotannin from Bark of Chestnut Tree, Castanea crenata Sieb, et Zucc. Agric. Biol. Chem. 48, 1411 (1984).Google Scholar
  17. 17.
    Nonaka, G., K. Ishimaru, T. Tanaka, and I. Nishioka: Tannins and Related Compounds, XVII: Galloylhamameloses from Castanea crenata and Sanguisorba officinalis L. Chem. Pharm. Bull. (Japan) 32, 483 (1984).Google Scholar
  18. 18.
    Ishimaru, K., G. Nonaka, and I. Nishioka: Gallic Acid Esters of Proio-quercitol, Quinic Acid and (−)-Shikimic Acid from Quercus mongolica and Q. myrsinaefolia. Phytochem. 26, 1501 (1987).Google Scholar
  19. 19.
    Nishimura, H., G. Nonaka, and I. Nishioka: Scyllo-quercitol Gallates and Hexa-hydroxydiphenoates from Quercus stenophylla. Phytochem. 25, 2599 (1986).Google Scholar
  20. 20.
    Nonaka, G., and I. Nishioka: Tannins and Related Compounds X: Rhubarb (2): Isolation and Structures of a Glycerol Gallate, Gallic Acid Glucosides, Galloylglucoses and Isolindleyin. Chem. Pharm. Bull. (Japan) 31, 1652 (1983).Google Scholar
  21. 21.
    Perkin, A. G., and Y. Uyeda: Occurrence of a Crystalline Tannin in the Leaves of the Acer ginnala. J. Chem. Soc. 1922, 66.Google Scholar
  22. 22.
    Bock, K., F. N. Lacour, R. S. Jensen, and B. J. Nielsen: The Structure of Acertannin. Phytochem. 19, 2033 (1980).Google Scholar
  23. 23.
    Haddock, E. A., R. K. Gupta, S. M. K. Al-Shafi, E. Haslam, and D. Magnolato: The Metabolism of Gallic Acid and Hexahydroxydiphenic Acid in Plants, Part 1: Introduction, Naturally Occurring Galloyl Esters. J. Chem. Soc. Perkin Trans. 1 1982, 2515.Google Scholar
  24. 24.
    Hatano, T., S. Hattori, Y. Ikeda, T. Shingu, and T. Okuda: Gallotannins Having 1,5-Anhydro-D-glucitol Core and Some Ellagitannins from Acer Species. Chem. Pharm. Bull. (Japan), 1902 (1990).Google Scholar
  25. 25.
    Okuda, T., K. Mori, and T. Hatano: Relationship of the Structure of Tannins to the Binding Activities with Hemoglobin and Methylene Blue. Chem. Pharm. Bull. (Japan) 33, 1424 (1985).Google Scholar
  26. 26.
    Haslam, E., R. D. Haworth, and D. A. Lawton: Gallotannins, Part VIII: The Preparation and Properties of Some Galloyl Esters of Quinic Acid. J. Chem. Soc. 1963, 2173.Google Scholar
  27. 27.
    Hatano, T., Y. Ikegami, and T. Okuda: Studies on the Tannins of Anacardiaceous Plants, Part 2: Tannins of Pistacia chinensis. Abstract Papers of the 33rd Annual Meeting of the Japanese Society of Pharmacognosy, p. 36 (1986).Google Scholar
  28. 28.
    Nonaka, G., M. Ageta, and I. Nishioka: Tannins and Related Compounds, XXV: A New Class of Gallotannins Possessing a (−)-Shikimic Acid Core from Castanopsis cuspidata var. sieboldii Nakai. (1). Chem. Pharm. Bull. (Japan) 33, 96 (1985).Google Scholar
  29. 29.
    Kashiwada, Y., G. Nonaka, and I. Nishioka: Galloylsucroses from Rhubarb. Phytochem. 27, 1469 (1988).Google Scholar
  30. 30.
    Strack, D., V. Wray, J.W. Metzger, and W. Grosse: TWO Anthocyanins Acylated with Gallic Acid from the Leaves of Victoria amazonica. Phytochem. 31, 989 (1992).Google Scholar
  31. 31.
    Ji, S.-H., N. Saito, M. Yokoi, A. Shigihara, and T. Honda: Galloylcyanidin Glycosides from Acer. Phytochem. 31, 655 (1992).Google Scholar
  32. 32.
    Kameda, K., T. Takaku, H. Okuda, Y. Kimura, T. Okuda, T. Hatano, I. Agata, and S. Arichi: Inhibitory Effects of Various Flavonoids Isolated from Leaves of Persimmon on Agniotensin-Converting Enzyme Activity. J. Nat. Prod. 50, 680 (1987).Google Scholar
  33. 33.
    Hatano, T., T. Yasuhara, R. Yoshihara, Y. Ikegami, M. Matsuda, K. Yazaki, I. Agata, S. Nishibe, T. Noro, M. Yoshizaki, and T. Okuda: Inhibitory Effects of Galloylated Flavonoids on Xanthine Oxidase. Planta Med. 57, 83 (1991).Google Scholar
  34. 34.
    Chen, X.-M., T. Yoshida, T. Hatano, M. Fukushima, and T. Okuda: Galloylarbutin and Other Polyphenols from Bergenia purpurascens. Phytochem. 26, 515 (1987).Google Scholar
  35. 35.
    Yazaki, K., S. Shida, and T. Okuda: Galloylhomoarbutin and Related Polyphenols from Pyrola incarnata. Phytochem. 28, 607 (1989).Google Scholar
  36. 36.
    Nonaka, G., I. Nishioka, T. Nagasawa, and H. Oura: Tannins and Related Compounds, I: Rhubarb (1). Chem. Pharm. Bull. (Japan) 29, 2862 (1981).Google Scholar
  37. 37.
    Ishimaru, K., G. Nonaka, and I. Nishioka: Phenolic Glucoside Gallates from Quercus mongolica and Q. acutissima. Phytochem. 26, 1147 (1987).Google Scholar
  38. 38.
    Ageta, M., K. Ishimaru, G. Nonaka, and I. Nishioka: Tannins and Related Compounds, LXIV: Six New Phenol Glucoside Gallates from Castanopsis cuspidata var. sieboldii Nakai (2). Chem. Pharm. Bull. (Japan) 36, 870 (1988).Google Scholar
  39. 39.
    Britton, G., and E. Haslam: Gallotannins, Part XII: Phenolic Constituents of Arctostaphyllos uva-ursi L. Spreng. J. Chem. Soc. 1965, 7312.Google Scholar
  40. 40.
    Nonaka, G., H. Nishimura, and I. Nishioka: Tannins and Related Compounds, IV: Seven New Phenol Glucoside Gallates from Quercus stenophylla Makino (1). Chem. Pharm. Bull. (Japan) 30, 2061 (1982).Google Scholar
  41. 41.
    Yoshikawa, M., E. Uchida, A. Kawaguchi, I. Kitagawa, and J. Yamahara: Galloyl-oxypaeoniflorin, Suffruticosides A, B, C and D, Five Antioxidative Glycosides, and Suffruticoside E, A Paeonol Glycoside, from Chinese Moutan Cortex. Chem. Pharm. Bull. (Japan) 40, 2248 (1992).Google Scholar
  42. 42.
    Hatano, T., T. Yasuhara, R. Abe, and T. Okuda: Galloylated Monoterpene Glucoside and a Dimeric Hydrolyzable Tannin from Cornus officinalis. Phytochem. 29, 2975 (1990).Google Scholar
  43. 43.
    Yoshida, T., K. Seno, Y. Takama, and T. Okuda: Bergenin Derivatives from Mallotus japonicus. Phytochem. 21, 1180 (1982).Google Scholar
  44. 44.
    Saijo, R., G. Nonaka, and I. Nishioka: Gallic Acid Esters of Bergenin and Norbergenin from Mallotus japonicus. Phytochem. 29, 267 (1990).Google Scholar
  45. 45.
    Tanaka, T., T. Sueyasu, G. Nonaka, and I. Nishioka: Tannins and Related Compounds, XXI: Isolation and Characterization of Galloyl and p-Hydroxybenzoyl Esters of Benzophenone and Xanthone C-Glucosides from Mangifera indica L. Chem. Pharm. Bull. (Japan) 32, 2676 (1984).Google Scholar
  46. 46.
    Matsuo, T., and S. Ito: The Chemical Structure of Kaki-tannin from Immature Fruit of the Persimmon (Diospyros kaki L.). Agric. Biol. Chem. 42, 1637 (1978).Google Scholar
  47. 47.
    Okuda, T., T. Yoshida, T. Hatano, M. Kuwahara, and S. Iida: Inhibitory Effects of Crude Drugs on Proteases: Tannins and Related Polyphenols. Proc. Symp. Wakan-Yaku 15, 111 (1982).Google Scholar
  48. 48.
    Hatano, T., K. Urita, and T. Okuda: Tannins from Saxifraga stronifera. J. Med. Pharm. Soc. Wakan-Yaku 3, 434 (1986).Google Scholar
  49. 49.
    Sakagami, H., K. Asano, S. Tanuma, T. Hatano, T. Yoshida, and T. Okuda: Stimulation of Monocyte Iodination and IL-1 Production by Tannins and Related Compounds. Anticancer Res. 12, 377 (1992).Google Scholar
  50. 50.
    Fukuchi, K., H. Sakagami, T. Okuda, T. Hatano, S. Tanuma, K. Kitajima, Y. Inoue, S. Inoue, S. Ichikawa, M. Nonoyama, and K. Konno: Inhibition of Herpes Simplex Virus Infection by Tannins and Related Compounds. Antiviral Res. 11, 285 (1989).Google Scholar
  51. 51.
    Yoshizawa, S., T. Horiuchi, M. Suganuma, S. Nishiwaki, J. Yatsunami, S. Okabe, T. Okuda, Y. Muto, K. Frenkel, W. Trol, and H. Fujiki: Penta-O-galloyl- β-D-glucose and (−)-Epigallocatechin Gallate. Cancer Preventive Agents. In: ACS Symposium Series 507. Phenolic Compounds in Food and Their Effects on Health II: Antioxidants and Cancer Prevention (M.-T. Huang, C.-T. Ho, C. Y. Lee, eds.), p. 316. Washington, DC: American Chemical Society. 1992.Google Scholar
  52. 52.
    Okuda, T., T. Yoshida, M. Ashida, and K. Yazaki: Structures of Pedunculagin, Casuarictin, Strictinin, Casuarinin, Casuariin and Stachyurin. J. Chem. Soc. Perkin Trans. 1 1983, 1765.Google Scholar
  53. 53.
    Wilkins, C.K., and B.A. Böhm: Ellagitannins from Tellima grandiflora. Phytochem. 15, 211 (1976).Google Scholar
  54. 54.
    Hatano, T., N. Ogawa, T. Yasuhara, and T. Okuda: Tannins of Rosaceous Plants, VIII: Hydrolyzable Tannin Monomers Having a Valoneoyl Group from Flower Petals of Rosa rugosa Thunb. Chem. Pharm. Bull. (Japan) 38, 3308 (1990).Google Scholar
  55. 55.
    Tanaka, T., G. Nonaka, and I. Nishioka: Tannins and Related Compounds, XLII: Isolation and Characterization of Four New Hydrolyzable Tannins, Terflavins A and B, Tergallagin and Tercatain from the Leaves of Terminalia catappa L. Chem. Pharm. Bull. (Japan) 34, 1039 (1986).Google Scholar
  56. 56.
    Okuda, T., T. Hatano, N. Ogawa, R. Kira, and M. Matsuda: Cornusiin A, A Dimerie Ellagitannin Forming Tautomers, and Accompanying New Tannins in Cornus officinalis. Chem. Pharm. Bull. (Japan) 32, 4662 (1984).Google Scholar
  57. 57.
    Yoshida, T., K. Yokoyama, O. Namba, and T. Okuda: Tannins and Related Polyphenols of Euphorbiaceous Plants, VIII: Tirucallins A, B and Euphorbin F, Monomeric and Dimerie Ellagitannins from Euphorbia tirucalli L. Chem. Pharm. Bull. (Japan) 39, 1137 (1991).Google Scholar
  58. 58.
    Yoshida, T., T. Maruyama, A. Nitta, and T. Okuda: Eucalbanins A, B and C, Monomeric and Dimerie Hydrolyzable Tannins from Eucalyptus alba Reinw. Chem. Pharm. Bull. (Japan) 40, 1750 (1992).Google Scholar
  59. 59.
    Yoshida, T., T. Hatano, T. Kuwajima, and T. Okuda: Oligomeric Hydrolyzable Tannins and Their JH-NMR Spectra and Partial Degradation. Heterocycles 33, 463 (1992).Google Scholar
  60. 60.
    Hatano, T., K. Yazaki, A. Okonogi, and T. Okuda: Tannins of Stachyurus Species, II: Praecoxins A, B, C and D, Four New Hydrolyzable Tannins from Stachyurus praecox Leaves. Chem. Pharm. Bull. (Japan) 39, 1689 (1991).Google Scholar
  61. 61.
    Yoshida, T., O. Namba, L. Chen, Y. Liu, and T. Okuda: Ellagitannin Monomers and Oligomers from Euphorbia prostrata Ait., and Oligomers from Loropetalum chinense Oliv. Chem. Pharm. Bull. (Japan) 38, 3296 (1990). Prostratins A, B and C in this paper were renamed as euprostins A, B and C.Google Scholar
  62. 62.
    Okuda, T., T. Yoshida, M. Kuwahara, M.U. Memon, and T. Shingu: Structures of Potentillin, Agrimonic Acids A and B, and Agrimoniin, a Dimerie Ellagitannin. Chem. Pharm. Bull. (Japan) 32, 2165 (1984).Google Scholar
  63. 63.
    Hatano, T., S. Hattori, and T. Okuda: Tannins of Coriaria japonica A. Gray, I: Coriariins A and B, New Dimerie and Monomeric Hydrolyzable Tannins. Chem. Pharm. Bull. (Japan) 34, 4092 (1986).Google Scholar
  64. 64.
    Hatano, T., R. Yoshihara, S. Hattori, M. Yoshizaki, T. Shingu, and T. Okuda: Tannins of Coriaria japonica A. Gray, III: Structures of Coriariins G, H, I and J. Chem. Pharm. Bull. (Japan) 40, 1703 (1992).Google Scholar
  65. 65.
    Yoshida, T., A.F. Ahmed, M.U. Memon, and T. Okuda: New Monomeric and Dimerie Hydrolyzable Tannins from Reaumuria hirtella and Tamarix pakistanica. Chem. Pharm. Bull. (Japan) 39, 2849 (1991).Google Scholar
  66. 66.
    Saijo, R., G. Nonaka, and I. Nishioka: Tannins and Related Compounds, LXXXIV: Isolation and Characterization of Five New Hydrolyzable Tannins from the Bark of Mallotus japonicus. Chem. Pharm. Bull. (Japan) 37, 2063 (1989).Google Scholar
  67. 67.
    Ishimatsu, M., T. Tanaka, G. Nonaka, I. Nishioka, M. Nishizawa, and T. Yamagishi: Tannins and Related Compounds, LXXV: Isolation and Characterization of Novel Diastereomeric Ellagitannins, Nupharins A and B, and Their Homo- logues from Nuphar Japonicum DC. Chem. Pharm. Bull. (Japan) 37, 129 (1989).Google Scholar
  68. 68.
    Okuda, T., T. Yoshida, T. Hatano, K. Yazaki, and M. Ashida: Ellagitannins of Casuarinaceae, Stachyuraceae and Myrtaceae. Phytochem. 21, 2871 (1982).Google Scholar
  69. 69.
    Yoshida, T., Y. Maruyama, M.U. Memon, T. Shingu, and T. Okuda: Gemins D, E and F, Ellagitannins from Geum japonicum. Phytochem. 24, 1041 (1985).Google Scholar
  70. 70.
    Okuda, T., T. Yoshida, and T. Hatano: Hydrated Stereostructure and Equilibration of Geraniin. J. Chem. Soc. Perkin Trans. 1 1982, 9.Google Scholar
  71. 71.
    Okuda, T., K. Mori, and T. Hatano: The Distribution of Geraniin and Mallotusinic Acid in the Order Geraniales. Phytochem. 19, 547 (1980).Google Scholar
  72. 72.
    Yoshida, T., K. Haba, F. Nakata, Y. Okano, T. Shingu, and T. Okuda: Tannins and Related Polyphenols of Melastomataceous Plants, III: Nobotanins G, H and I, Dimerie Hydrolyzable Tannins from Heterocentron roseum. Chem. Pharm. Bull. (Japan) 40, 66 (1992).Google Scholar
  73. 73.
    Yazaki, K., T. Hatano, and T. Okuda: Structures of Didehydrogeraniin, Furosinin and Furosin. J. Chem. Soc. Perkin Trans. 1 1989, 2289.Google Scholar
  74. 74.
    Schmidt, O. Th., J. Schulz, and R. Wurmb: Terchebin. Liebigs Ann. Chem. 706, 169 (1967).Google Scholar
  75. 75.
    Okuda, T., T. Hatano, H. Nitta, and R. Fujii: Hydrolyzable Tannins Having Enantiomeric Dehydrohexahydroxydiphenoyl Group: Revised Structure of Terchebin and Structure of Granatin B. Tetrahedron Lett. 21, 4361 (1980).Google Scholar
  76. 76.
    Fürstenwerth, H., and H. Schildknecht: Isoterchebin, der gelbe Farbstoff des Zistrosenwürgers Cytinus hypocistis ( Rafflesiaceae, Schmarotzerblumengewächse). Liebigs Ann. Chem. 1976, 112.Google Scholar
  77. 77.
    Okuda, T., T. Hatano, and T. Yasui: Revised Structure of Isoterchebin, Isolated from Cornus officinalis. Heterocycles 16, 1681 (1981).Google Scholar
  78. 78.
    Okuda, T., T. Yoshida, K. Mori, and T. Hatano: Tannins of Medicinal Plants and Drugs. Heterocycles 15, 1323 (1981).Google Scholar
  79. 79.
    Okuda, T., and K. Seno: Mallotusinic Acid and Mallotinic Acid, New Hydrolyzable Tannins from Mallotus japonicus. Tetrahedron Lett. 1978, 139.Google Scholar
  80. 80.
    Lee, S.-H., T. Tanaka, G. Nonaka, and I. Nishioka: Tannins and Related Compounds, XCV: Isolation and Characterization of Helioscopinins and Helioscopins. Four New Hydrolyzable Tannins from Euphorbia helioscopia L. Chem. Pharm. Bull. (Japan) 38, 1518 (1990).Google Scholar
  81. 81.
    Akazawa, M., Y. Kashiwada, G. Nonaka, and I. Nishioka: Tannins and Related Compounds of Carpinus laxiflora. Abstract Papers (III) of the 109th Annual Meeting of the Pharmaceutical Society of Japan, p. 158 (1989).Google Scholar
  82. 82.
    Lee, S.-H., T. Tanaka, G. Nonaka, and I. Nishioka: Tannins and Related Compounds, CV: Monomeric and Dimeric Hydrolyzable Tannins Having a Dehydrohexahydroxydiphenoyl Group, Supinanin, Euphorscopin, Euphorhelin and Jolkianin, from Euphorbia Species. Chem. Pharm. Bull. (Japan) 39, 630 (1991).Google Scholar
  83. 83.
    Lin, J.-H., G. Nonaka, and I. Nishioka: Tannins and Related Compounds, XCIV: Isolation and Characterization of Seven New Hydrolyzable Tannins from the Leaves of Macaranga tanarius. Chem. Pharm. Bull. (Japan) 38, 1218 (1990).Google Scholar
  84. 84.
    Lin, J.-H., M. Ishimatsu, T. Tanaka, G. Nonaka, and I. Nishioka: Structures of Macaranins and Macarinins, New Hydrolyzable Tannins Possessing Macaranoyl and Tergalloyl Ester Groups, from the Leaves of Macaranga sinensis (Baill.) Muell.-Arg. Chem. Pharm. Bull. (Japan) 38, 1844 (1990).Google Scholar
  85. 85.
    Ikeya, Y., H. Taguchi, I. Yoshioka, and H. Kobayashi: The Constituents of Schizandra chinensis Baill. Isolation and Structure Determination of Five New Lig- nans, Gomisin A, B, C, F and G and the Absolute Structure of Schizandrin. Chem. Pharm. Bull. 27, 1383 (1979).Google Scholar
  86. 86.
    Okuda, T., T. Yoshida, T. Hatano, T. Koga, N. Toh, and K. Kuriyama: Circular Dichroism of Hydrolyzable Tannins, I: Ellagitannins and Gallotannins. Tetrahedron Lett. 23, 3937 (1982).Google Scholar
  87. 87.
    Harada, N., and K. Nakanishi: The Exciton Chirality Method and Its Application to Configurational and Conformational Studies of Natural Products. Acc. Chem. Res. 5, 257 (1972).Google Scholar
  88. 88.
    Okuda, T., T. Yoshida, T. Hatano, T. Koga, N. Toh, and K. Kuriyama: Circular Dichroism of Hydrolyzable Tannins, II: Dehydroellagitannins. Tetrahedron Lett. 23, 3941 (1982).Google Scholar
  89. 89.
    Yoshida, T., R. Fujii, and T. Okuda: Revised Structures of Chebulinic Acid and Chebulagic Acid. Chem. Pharm. Bull. (Japan) 28, 3713 (1980).Google Scholar
  90. 90.
    Uddin, M., and E. Haslam: Gallotannins, Part 15: Some Observations on the Structure of Chebulinic Acid and Its Derivatives. J. Chem. Soc. (C) 1967, 2381.Google Scholar
  91. 91.
    Yoshida, T., H. Itoh, S. Matsunaga, R. Tanaka, and T. Okuda: Hydrolyzable Tannins with 1C4 Glucose Core from Phyllanthus flexuosus Muell. Arg. Chem. Pharm. Bull. (Japan) 40, 53 (1992).Google Scholar
  92. 92.
    Namba, O., T. Hatano, T. Yoshida, and T. Okuda: Studies on the Constituents of Geranium thunbergii, Part 17: New Ellagitannins. Abstract Papers (III) of the 108th Annual Meeting of the Pharmaceutical Society of Japan, p. 339 (1988).Google Scholar
  93. 93.
    Yoshida, T., Z.-X. Jin, and T. Okuda: Heterophylliins A, B, C, D, and E, Ellagitannin Monomers and Dimers from Corylus heterophylla. Chem. Pharm. Bull. (Japan) 39, 876 (1991).Google Scholar
  94. 94.
    Saijo, R., G. Nonaka, and I. Nishioka: Isolation and Characterization of Four New Hydrolyzable Tannins from the Leaves of Mallotus repandus. Chem. Pharm. Bull. (Japan) 37, 2624 (1989).Google Scholar
  95. 95.
    Okuda, T., T. Yoshida, T. Hatano, K. Yazaki, R. Kira, and Y. Ikeda: Chromatography of Tannins, II: Preparative Fractionation of Hydrolyzable Tannins by Centrifugal Partition Chromatography. J. Chromatogr. 362, 375 (1986).Google Scholar
  96. 96.
    Okuda, T., T. Yoshida, T. Hatano, Y. Ikeda, T. Shingu, and T. Inoue: Constituents of Geranium thunbergii Sieb, et Zucc., XIII: Isolation of Water-soluble Tannins by Centrifugal Partition Chromatography, and Biomimetic Synthesis of Elaeocarpusin. Chem. Pharm. Bull. (Japan) 34, 4075 (1986).Google Scholar
  97. 97.
    Tanaka, T., G. Nonaka, I. Nishioka, K. Miyahara, and T. Kawasaki: Isolation and Structure Elucidation of Elaeocarpusin, a Novel Ellagitannin from Elaeocarpus sylvestris var. ellipticusu. J. Chem. Soc. Perkin Trans. 1 1986, 369.Google Scholar
  98. 98.
    Okuda, T., T. Yoshida, and T. Hatano: Biomimetic Synthesis of Elaeocarpusin. Heterocycles 24, 1841 (1986).Google Scholar
  99. 99.
    Foo, L.Y., and H. Wong: Phyllanthusiin D, an Unusual Hydrolysable Tannin from Phyllanthus amarus. Phytochem. 31, 711 (1992).Google Scholar
  100. 100.
    Yazaki, K., T. Yoshida, and T. Okuda: Tannin Production in Cell Suspension Cultures of Geranium thunbergii. Phytochem. 30, 501 (1991).Google Scholar
  101. 101.
    Mayer, W.: Über die Gerbstoffe aus dem Holz der Edelkastanie und Eiche. Das Leder 22, 277 (1971).Google Scholar
  102. 102.
    Nonaka, G., T. Sakai, T. Tanaka, K. Mihashi, and I. Nishioka: Tannins and Related Compounds, XCVII: Structure Revision of C-glycosidic Ellagitannins, Castalagin, Vescalagin, Casuarinin and Stachyurin, and Related Hydrolyzable Tannins. Chem. Pharm. Bull. (Japan) 38, 2151 (1990).Google Scholar
  103. 103.
    Okuda, T., T. Yoshida, T. Hatano, K. Yazaki, Y. Ikegami, and T. Shingu: Guavins A, C and D, Complex Tannins from Psidium guajava. Chem. Pharm. Bull. (Japan) 35, 443 (1987). The structure of guavin A in this paper has been revised to be an isomer of malabathrin E (108) (106), in which the (−)-epicatechin moiety of 108 is replaced by (+)-catechin unit.Google Scholar
  104. 104.
    Hatano, T., S, Shida, L. Han, and T. Okuda: Camelliatannins A and B, Two New Complex Tannins from Camellia japonica L. Chem. Pharm. Bull. (Japan) 39, 876 (1991).Google Scholar
  105. 105.
    Hatano, T., L. Han, S. Taniguchi, T. Chou, T. Shingu, H. Sakagami, M. Takeda, H. Nakashima, T. Murayama, N. Yamamoto, T. Yoshida, and T. Okuda: Anti- HIV Tannins from Camellia japonica and Related Plant Species. Symposium Papers of the 34th Symposium on the Chemistry of Natural Products, p. 510 (1992).Google Scholar
  106. 106.
    Yoshida, T., F. Nakata, K. Hosotani, A. Nitta, and T. Okuda: Three New Complex Tannins from Melastoma malabathricum L. Chem. Pharm. Bull. (Japan) 40, 1727 (1992).Google Scholar
  107. 107.
    Okuda, T., T. Yoshida, M. Kuwahara, M.U. Memon, and T. Shingu: Agrimoniin and Potentillin, Ellagitannin Dimer and Monomer Having a-Glucose Core. J. Chem. Soc. Chem. Commun. 1982, 163.Google Scholar
  108. 108.
    Yoshida, T., L. Chen, T. Shingu, and T. Okuda: Euphorbins A and B, Novel Dimeric Dehydroellagitannins from Euphorbia hirta L. Chem. Pharm. Bull. (Japan) 36, 2940 (1988).Google Scholar
  109. 109.
    Yoshida, T., O. Namba, L. Chen, and T. Okuda: Euphorbin C, an Equilibrated Dimeric Dehydroellagitannin Having a New Tetrameric Galloyl Group. Chem. Pharm. Bull. (Japan) 38, 86 (1990).Google Scholar
  110. 110.
    Yoshida, T., O. Namba, C.-F. Lu, L.-L. Yang, K.-Y. Yen, and T. Okuda: Antidesmin A, a New Dimeric Hydrolyzable Tannin from Antidesma pentandrum var. barbathum. Chem. Pharm. Bull. (Japan) 40, 338 (1992).Google Scholar
  111. 111.
    Tanaka, T., G. Nonaka, I. Nishioka, I. Kouno, and F.-C. Ho: Dehydroellagitannin from Bishofia javanica. Phytochem. 38, 509 (1995).Google Scholar
  112. 112.
    Tanaka, T., F. Nonaka, and I. Nishioka: Tannins and Related Compounds, Part 28: Revision of the Structures of Sanguiins H-6, H-2, and H-3, and Isolation and Characterization of Sanguiin H-ll, a Novel Tetrameric Hydrolysable Tannin, and Seven Related Tannins, from Sanguisorba officinalis. J. Chem. Res. (M) 1985, 2001.Google Scholar
  113. 113.
    Yoshida, T., Y. Maruyama, M.U. Memon, T. Shingu, and T. Okuda: Gemins A, B, and C, New Dimeric Ellagitannins from Geum japonicum. J. Chem. Soc. Perkin Trans. 1 1985, 315.Google Scholar
  114. 114.
    Yoshida, T., K. Tanaka, X.-M. Chen, and T. Okuda: Hydrolyzable Tannins with Dehydrodigalloyl Group from Rosa laevigata Mischx. Chem. Pharm. Bull. (Japan) 37, 920 (1989).Google Scholar
  115. 115.
    Yoshida, T., K. Tanaka, X.-M. Chen, and T. Okuda: Dimeric Ellagitannins, Laevigatins E, F and G, from Rosa laevigata. Phytochem. 28, 2451 (1989).Google Scholar
  116. 116.
    Yoshida, T., Z.-X. Jin, and T. Okuda: Hydrolyzable Tannin Oligomers from Rosa davurica. Phytochem. 30, 2747 (1991).Google Scholar
  117. 117.
    Hatano, T., Hattori, S., and T. Okuda: Coriariins C, D, E and F, New Dimeric and Monomeric Hydrolyzable Tannins. Chem. Pharm. Bull. (Japan) 34, 4533 (1986).Google Scholar
  118. 118.
    Ishimatsu, M., T. Tanaka, G. Nonaka, I. Nishioka, M. Nishizawa, and T. Yamagishi: Tannins and Related Compounds, LXXIX: Isolation and Characterization of Novel Dimeric and Trimeric Hydrolyzable Tannins, Nupharins C, D, E and F, from Nuphar japonicum DC. Chem. Pharm. Bull. (Japan) 37, 1735 (1989).Google Scholar
  119. 119.
    Yoshida, T., A.F. Ahmed, and T. Okuda: Tannins of Tamaricaceous Plants, III: New Dimeric Hydrolyzable Tannins from Reaumuria hirtella. Chem. Pharm. Bull. (Japan) 41, 672 (1993).Google Scholar
  120. 120.
    Yoshida, T., T. Hatano, A.F. Ahmed, A. Okonogi, and T. Okuda: Structures of Isorugosin E and Hirtellin B, Dimeric Hydrolyzable Tannins Having a Trisgalloyl Group. Tetrahedron 47, 3575 (1991).Google Scholar
  121. 121.
    Hatano, T., N. Ogawa, T. Shingu, and T. Okuda: Rugosins D, E, F and G, Dimeric and Trimeric Hydrolyzable Tannins with Valoneoyl Group from Flower Petals of Rosa rugosa Thunb. Chem. Pharm. Bull. (Japan) 38, 3341 (1990).Google Scholar
  122. 122.
    Yoshida, T., Z.-X. Jin, and T. Okuda: Unpublished data.Google Scholar
  123. 123.
    Hatano, T., N. Ogawa, R. Kira, T. Yasuhara, and T. Okuda: Tannins of Cor- naceous Plants, I: Cornusiins A, B and C, Dimeric, Monomeric and Trimeric Hydrolyzable Tannins from Cornus officinalis, and Orientation of Valoneoyl Group in Related Tannins. Chem. Pharm. Bull. (Japan) 37, 2083 (1989).Google Scholar
  124. 124.
    Hatano, T., T. Yasuhara, and T. Okuda: Tannins of Cornaceous Plants, II: Cornusiins D, E and F, New Dimeric and Trimeric Hydrolyzable Tannins from Cornus officinalis. Chem. Pharm. Bull. (Japan) 37, 2665 (1989).Google Scholar
  125. 125.
    Hatano, T., Y. Ikegami, T. Shingu, and T. Okuda: Camptothins A and B, New Dimeric Hydrolyzable Tannins from Camptotheca acuminata Decne. Chem. Pharm. Bull. (Japan) 36, 2017 (1988).Google Scholar
  126. 126.
    Hatano, T., A. Okonogi, K. Yazaki, and T. Okuda: Trapanins A and B, Oligomeric Hydrolyzable Tannins from Trapa japanica Flerov. Chem. Pharm. Bull. (Japan) 38, 2707 (1990).Google Scholar
  127. 127.
    Yoshida, T., H. Ohbayashi, K. Ishihara, W. Ohwashi, K. Haba, Y. Okano, T. Shingu, and T. Okuda: Hydrolyzable Tannins from Tibouchina semidecandra Cogn. Chem. Pharm. Bull. (Japan) 39, 2233 (1991).Google Scholar
  128. 128.
    Yoshida, T., W. Ohwashi, K. Haba, H. Ohbayashi, K. Ishihara, Y. Okano, T. Shingu, and T. Okuda: Nobotanins B, C and E, Hydrolyzable Tannin Dimer and Trimers from Tibouchina semidecandra Cogn. Chem. Pharm. Bull. (Japan) 39, 2264 (1991).Google Scholar
  129. 129.
    Hatano, T., T. Yasuhara, M. Matsuda, K. Yazaki, T. Yoshida, and T. Okuda: Oenothein B, a Dimeric Hydrolysable Tannin with Macroeyclic Structure and Accompanying Tannins from Oenothera erythrosepala. J. Chem. Soc. Perkin Trans. 1 1990, 2735.Google Scholar
  130. 130.
    Chou, T., T. Yoshida, and T. Okuda: Three Hydrolyzable Tannin Oligomers Having Macrocyclic Structure from Oenothera laciniata. Abstract Papers of the XVth International Botanical Congress, Yokohama, p. 377 (1993).Google Scholar
  131. 131.
    Okuda, T., T. Yoshida, T. Hatano, K. Yazaki, R. Kira, and Y. Ikeda: Preparative Fractionation of Hydrolyzable Tannins by Centrifugal Partition Chromatography. J. Chromatogr. 362, 375 (1986).Google Scholar
  132. 132.
    Yoshida, T., T. Chou, A. Nitta, K. Miyamoto, R. Koshiura, and T. Okuda: Woodfordin C, a Macro-ring Hydrolyzable Tannin Dimer with Antitumor Activity and Accompanying Dimers from Woodfordia fruticosa Flowers. Chem. Pharm. Bull. (Japan) 38, 1211 (1990).Google Scholar
  133. 133.
    Kadota, S., Y. Takamori, K.N. Nyein, T. Kikuchi, K. Tanaka, and H. Ekimoto: Constituents of Woodfordia fruticosa Kurz, I: Isolation, Structure, and Proton and Carbon-13 Nuclear Magnetic Resonance Signal Assignments of Woodfruticosin (Woodfordin C), an Inhibitor of Deoxyribonucleic Acid Topoisomerase II. Chem. Pharm. Bull. (Japan) 38, 2687 (1990).Google Scholar
  134. 134.
    Yoshida, T., T. Chou, Y. Maruyama, and T. Okuda: Camelliins A and B, Two New Dimeric Hydrolyzable Tannins from Flower Buds of Camellia japonica L. and Camellia sasanqua Thunb. Chem. Pharm. Bull. (Japan) 38, 2681 (1990).Google Scholar
  135. 135.
    Yoshida, T., T. Chou, A. Nitta, and T. Okuda: Monomeric and Dimeric Hydrolyzable Tannins Having a Dilactonized Valoneoyl Group from Schima wallichii Koeth. Chem. Pharm. Bull. (Japan) 39, 2247 (1991).Google Scholar
  136. 136.
    Xu, Y.-M., T. Sakai, T. Tanaka, G. Nonaka, and I. Nishioka: Tannins and Related Compounds, CVI: Preparation of Aminoalditol Derivatives of Hydrolyzable Tannins Having a- and β-Glucopyranose Cores, and Its Application to the Structure Elucidation of New Tannins, Reginins A and B and Flosin A, Isolated from Lagerstroemia flos-reginae Retz. Chem. Pharm. Bull. (Japan) 39, 639 (1991).Google Scholar
  137. 137.
    Xu, Y.-M., T. Tanaka, G. Nonaka, and I. Nishioka: Tannins and Related Compounds, CVII: Structure Elucidation of Three New Monomeric and Dimeric Ellagitannins, Flosin B and Reginins C and D, Isolated from Lagerstroemia flos-regina Retz. Chem. Pharm. Bull. (Japan) 39, 647 (1991).Google Scholar
  138. 138.
    Yoshida, T., Z.-X. Jin, and T. Okuda: Heterophylliins A, B, C, D and E, Ellagitannin Monomers from Corylus heterophylla Fisch. Chem. Pharm. Bull. (Japan) 39, 49 (1991).Google Scholar
  139. 139.
    Yoshida, T., T. Hatano, and T. Okuda: Chromatography of Tannins, IV: Separation of Labile Oligomeric Hydrolysable Tannins and Related Polyphenols by Centrifugal Partition Chromatography. J. Chromatogr. 467, 139 (1989).Google Scholar
  140. 140.
    Yoshida, T., W.-S. Feng, and T. Okuda: Tannins and Related Polyphenols of Rosaceous Medicinal Plants, XII: Roshenins A-E, Dimeric Hydrolyzable Tannins from Rosa henryi Boul. Chem. Pharm. Bull. (Japan) 40, 1997 (1992).Google Scholar
  141. 141.
    Tanaka, T., H. Tachibana, G. Nonaka, I. Nishioka, and F.-L. Hsu: Tannins and Related Compounds, CXXII: New Dimeric Trimeric and Tetrameric Ellagitannins, Lambertianins A-D, from Rubus lambertianus Seringe. Chem. Pharm. Bull. (Japan) 41, 1214 (1993).Google Scholar
  142. 142.
    Yoshida, T., T. Chou, M. Matsuda, T. Yasuhara, K. Yazaki, T. Hatano, A. Nitta, and T. Okuda: Woodfordin D and Oenothein A, Trimeric Hydrolyzable Tannins of Macro-ring Structure with Antitumor Activity. Chem. Pharm. Bull. (Japan) 39, 1157 (1991).Google Scholar
  143. 143.
    Yoshida, T., T. Chou, A. Nitta, and T. Okuda: Hydrolyzable Tannin Oligomers with Macrocyclic Structures, and Accompanying Tannins from Woodfordia fruticosa Kurz. Chem. Pharm. Bull. (Japan) 40, 2023 (1992).Google Scholar
  144. 144.
    Yoshida, T., O. Namba, L. Chen, and T. Okuda: Euphorbin E, a Hydrolyzable Tannin Dimer of Highly Oxidized Structure from Euphorbia hirta. Chem. Pharm. Bull. (Japan) 38, 1113 (1990).Google Scholar
  145. 145.
    Nonaka, G., T. Sakai, K. Mihashi, and I. Nishioka: Tannins and Related Com-pounds, CIX: Isolation of Alienanins A and B, Novel C, C-Linked Ellagitannin Dimers from Quercus aliena Blume. Chem. Pharm. Bull. (Japan) 39, 884 (1991).Google Scholar
  146. 146.
    Penhoat, C. L. M. H., V. M. F. Michon, S. Peng, C. Viriot, A. Scalbert, and D. Gage: Structural Elucidation of New Ellagitannins from Quercus robur L. Roburins A-E. J. Chem. Soc. Perkin Trans. 1 1991, 1653.Google Scholar
  147. 147.
    Lin, T.-C., T. Tanaka, G. Nonaka, I. Nishioka, and T.-J. Young: Tannins and Related Compounds, CVIII: Isolation and Characterization of Novel Complex Tannins (Flavano-ellagitannins), Anogeissinin and Anogeissusins A and B, from Anogeissus acuminata (Roxb ex DC.) Guill. et Perr. var. lanceolata Wall, ex Clarke. Chem. Pharm. Bull. (Japan) 39, 1144 (1991).Google Scholar
  148. 148.
    Yoshida, T., F. Nakata, K. Hosotani, A. Nitta, and T. Okuda: Tannins from Melastoma malabathricum. Phytochem. 31, 2829 (1992).Google Scholar
  149. 149.
    Yoshida, T., X.-M. Chen, T. Hatano, M. Fukushima, and T. Okuda: Tannins and Related Polyphenols of Rosaceous Plants, IV: Roxbins A and B from Rosa roxburghii Fruits. Chem. Pharm. Bull. (Japan) 35, 1817 (1987).Google Scholar
  150. 150.
    Tanaka, T, A. Morita, G. Nonaka, T.-C. Lin, I. Nishioka, and F.-C. Ho: Tannins and Related Compounds, CIII: Isolation and Characterization of New Monomerie, Dimeric and Trimeric Ellagitannins, Calamansanin and Calamanins A, B and C, from Terminalia calamansanai (Blanco) Rolfe. Chem. Pharm. Bull. (Japan) 39, 60 (1991).Google Scholar
  151. 151.
    Nakata, F., T. Yoshida, and T. Okuda: Ellagitannins from Tibouchina semidecandra. Abstract Papers (2) of the 112th Annual Meeting of the Pharmaceutical Society of Japan, p. 206 (1992).Google Scholar
  152. 152.
    Kobayashi, S., T. Hatano, T. Yoshida, T. Okuda, C.-F. Lu, L.-L. Yang, K.-Y. Yen: Tannins from Barringtonia asiatica. Abstract Papers (2) of the 112th Annual Meeting of the Pharmaceutical Society of Japan, p. 208 (1992).Google Scholar
  153. 153.
    Atallah, A.F., T. Yoshida, and T. Okuda: Tannins of Tamaricaceous Plants, V: New Dimeric, Trimeric and Tetrameric Ellagitannins from Reaumuria hirtella. Chem. Pharm. Bull. (Japan) 42, 246 (1994).Google Scholar
  154. 154.
    Yoshida, T., A.F. Ahmed, and T. Okuda: Tamarixinins B and C, Dimeric Hydrolyz-able Tannins from Tamarix pakistanica. Phytochem. 33, 197 (1993).Google Scholar
  155. 155.
    Agata, I., T. Hatano, Y. Nakaya, T. Sugaya, S. Nishibe, T. Yoshida, and T. Okuda: Tannins and Related Polyphenols of Euphorbiaceous Plants, VIII: Eumaculin A and Eusupinin A, and Accompanying Polyphenols from Euphorbia maculata L. and E. supina Raiin. Chem. Pharm. Bull. (Japan) 39, 881 (1991).Google Scholar
  156. 156.
    Yoshida, T., S. Tanei, Y.-Z. Liu, K. Yuan, C.-R. Ji, and T. Okuda: Hydrolyzable Tannins from Loropetalum chinense. Phytochem. 32, 1287 (1993).Google Scholar
  157. 157.
    Hatano, T., R. Kira, T. Yasuhara, and T. Okuda: Tannins of Hamamelidaceous Plants, III: Isorugosins A, B and D, New Ellagitannins from Liquidambar formosana. Chem. Pharm. Bull. (Japan) 36, 3920 (1988).Google Scholar
  158. 158.
    Hatano, T., A. Okonogi, and T. Okuda: Oligomeric Hydrolyzable Tannins from Liquidambar formosana and Spectral Analysis of the Orientation of Valoneoyl Groups in Their Molecules. In: Plant Polyphenols. Synthesis, Properties, Significance (R. W. Hemingway and P. E. Laks, eds.), p. 195. New York: Plenum Press. 1992.Google Scholar
  159. 159.
    Nonaka, G., S. Nakayama, and I. Nishioka: Tannins and Related Compounds, LXXXIII: Isolation and Structure of Hydrolyzable Tannins, Phillyraeoidins A–E from Quercus phillyraeoides. Chem. Pharm. Bull. (Japan) 37, 2030 (1989).Google Scholar
  160. 160.
    Tanaka, T., M. Ueda, G. Nonaka, and I. Nishioka: Tannins from Lagerstroemia indica L. Abstract Papers of the 108th Annual Meeting of the Pharmaceutical Society of Japan, p. 278 (1988).Google Scholar
  161. 161.
    Yoshida, T., O. Namba, K. Yokoyama, and T. Okuda: Hydrolyzable Tannin Oligomers from Euphorbiaceous Plants. Symposium Papers of the 31st Symposium on the Chemistry of Natural Products, p. 601 (1989).Google Scholar
  162. 162.
    Lin, J.-H., T. Tanaka, G. Nonaka, I. Nishioka, and I.-S. Chen: Tannins and Related Compounds, XCVIII: Structures of Three New Dimeric Ellagitannins, Excoecarianin and Excoecarinins A and B, Isolated from the Leaves of Excoecaria kawakamii Hayata. Chem. Pharm. Bull. (Japan) 38, 2162 (1990).Google Scholar
  163. 163.
    Agata, I., T. Sugaya, S. Nishibe, T. Hatano, T. Yoshida, and T. Okuda: Tannins of Euphorbia maculata and E. supina. Abstract Papers (2) of the 111th Annual Meeting of the Pharmaceutical Society of Japan, p. 177 (1991).Google Scholar
  164. 164.
    Saijo, R., G. Nonaka, I. Nishioka, I.-S. Chen, and T.-H. Hwang: Tannins and Related Compounds, LXXXVIII: Isolation and Characterization of Hydrolyzable Tannins from Mallotus japonicus (Thunb.) Muell.-Arg. Chem. Pharm. Bull. (Japan) 37, 2940 (1989).Google Scholar
  165. 165.
    Shimokawa, H., G. Nonaka, and I. Nishioka: Tannins of Casuarina glauca. Abstract Papers (2) of the 111th Annual Meeting of the Pharmaceutical Society of Japan, p. 147 (1991); Abstract Papers of the 38th Annual Meeting of the Japanese Society of Pharmacognosy, p. 104 (1991).Google Scholar
  166. 166.
    Yoshida, T., Y. Ikeda, H. Ohbayashi, K. Ishihara, W. Ohwashi, T. Shingu, and T. Okuda: Dimeric Ellagitannins in Plants of Melastomataceae. Chem. Pharm. Bull. (Japan) 34, 2676 (1986).Google Scholar
  167. 167.
    Bate-Smith, E.C.: Detection and Determination of Ellagitannins. Phytochem. 11, 1153 (1972).Google Scholar
  168. 168.
    Okuda, T., K. Mori, and N. Hayashi: Application of Determination Methods of Tannin Activity with Hemoglobin and of Ellagitannin with Nitrous Acid. Yakugaku Zasshi 96, 1143 (1976).Google Scholar
  169. 169.
    Okuda, T., T. Yoshida, and T. Hatano: Application of Centrifugal Partition Chromatography to Separation of Tannins and Related Polyphenols. J. Liq. Chromatogr. 11, 2447 (1988).Google Scholar
  170. 170.
    Okuda, T., T. Yoshida, T. Hatano, K. Mori, and T. Fukuda: Fractionation of Pharmacologically Active Plant Polyphenols by Centrifugal Partition Chromatography. J. Liq. Chromatogr. 13, 3637 (1990).Google Scholar
  171. 171.
    Yoshida, T., T. Hatano, and T. Okuda: Two-Dimensional NMR Spectra of Hy- drolyzable Tannins Which Form Equilibrium Mixtures. Mag. Reson. Chem. 30, 546 (1992).Google Scholar
  172. 172.
    Yoshida, T., T. Hatano, T. Okuda, M.U. Memon, and T. Shingu: Spectral and Chromatographic Analyses of Tannins, I:13C Nuclear Magnetic Resonance Spectra of Hydrolyzable Tannins. Chem. Pharm. Bull. (Japan) 32, 1790 (1984).Google Scholar
  173. 173.
    Hatano, T., T. Yoshida, T. Shingu, and T. Okuda: 13C Nuclear Magnetic Resonance Spectra of Hydrolyzable Tannins, II: Tannins Forming Anomer Mixtures. Chem. Pharm. Bull. (Japan) 36, 2925 (1988).Google Scholar
  174. 174.
    Yoshida, T., T. Hatano, T. Kuwajima, and T. Okuda: Oligomeric Hydrolyzable Tannins and Their 1HNMR Spectra and Partial Degradation. Heterocycles 33, 463 (1992).Google Scholar
  175. 175.
    Cronquist, A.: The Evolution and Classification of Flowering Plants, 2nd Ed. New York: The New York Botanical Garden. 1988.Google Scholar
  176. 176.
    Maki, Y., M. Suzuki, O. Toyota, and M. Takaya: Studies on the Smiles Rearrange-ment, XII: Synthesis and Structural Assignment of Two Isomeric N-Phenyl-2,3- diazaphenothiazinones. Chem. Pharm. Bull. (Japan) 21, 241 (1973).Google Scholar
  177. 177.
    Okuda, T., T. Hatano, T. Kaneda, M. Yoshizaki, and T. Shingu: Liquidambin, a New Ellagitannin from Liquidambar formosana. Phytochem. 26, 2053 (1987).Google Scholar
  178. 178.
    Okuda, T., T. Hatano, I. Agata, S. Nishibe, and K. Kimura: Tannins in Artemisia montana, A. princeps and Related Species of Plant. Yakugaku Zasshi 106, 894 (1986).Google Scholar
  179. 179.
    Timmermann, B. N., J. J. Hoffman, S. D. Jolad, K. H. Schram, R. E. Klenck, and R. B. Bates: Constituents of Chrysothamnus paniculatus 3: 3,4,5-Tricaffeoylquinic Acid (A New Shikimate Prearomatic) and 3,4-, 3,5- and 4,5-Dicaffeoylquinic Acids. J. Nat. Prod. 46, 365 (1983).Google Scholar
  180. 180.
    Merfort, I.: Caffeoylquinic Acids from Flowers of Arnica montana and Arnica chamissonis. Phytochem. 31, 2111 (1992).Google Scholar
  181. 181.
    Agata, I., S. Goto, T. Hatano, S. Nishibe, and T. Okuda: 1,3,5-Tri-O-caffeoylquinic Acid from Xanthium strumarium. Phytochem. 33, 508 (1993).Google Scholar
  182. 182.
    Okuda, T., T. Hatano, I. Agata, and S. Nishibe: The Components of Tannic Activities in Labiatae Plants, I: Rosmarinic Acid from Labiatae Plants in Japan. Yakugaku Zasshi 106, 1108 (1986).Google Scholar
  183. 183.
    Hegnauer, R.: Chemotaxonomie der Pflanzen, Bd. 4, p. 327. Basel-Stuttgart: Birkhäuser. 1966.Google Scholar
  184. 184.
    Kelly, C. J., R. C. Harruff, and M. Carmack: The Polyphenolic Acids of Lithospermum ruderale, II: Carbon-13 Nuclear Magnetic Resonance of Lithospermic and Rosmarinic Acids. J. Org. Chem. 41, 449 (1976).Google Scholar
  185. 185.
    Wagner, H.: Phenolic Compounds in Plants of Pharmaceutical Interest. In: Biochemistry of Plant Phenolics (T. Swain, J. B. Harborne, and C. F. vanSumere, eds.), p. 598. New York: Plenum Press. 1979.Google Scholar
  186. 186.
    Ai, C.-B, and L.-N. Li: Stereostructure of Salvianolic Acid B and Isolation of Salvianolic Acid C from Salvia miltiorrhiza. J. Nat. Prod. 51, 145 (1988).Google Scholar
  187. 187.
    Agata, I., H. Kusakabe, T. Hatano, S. Nishibe, and T. Okuda: Melitric Acids A and B, New Trimeric Caffeic Acid Derivatives from Melissa officinalis. Chem. Pharm. Bull. (Japan) 41, 1608 (1993).Google Scholar
  188. 188.
    Agata, T., T. Hatano, S. Nishibe, and T. Okuda: A Tetrameric Derivative of Caffeic Acid from Rabdosia japonica. Phytochem. 28, 2447 (1989).Google Scholar
  189. 189.
    Nishizawa, M., M. Tsuda, and K. Hayashi: Two Caffeic Acid Tetramers Having Enantiomeric Phenyldihydronaphthalene Moieties from Macrotomia euchroma. Phytochem. 29, 2645 (1990).Google Scholar
  190. 190.
    Agata, I., Y. Nakaya, S. Nishibe, T. Hatano, and T. Okuda: Polyphenols of Rabdosia trichocarpa. Abstract Papers (II) of the 110th Annual Meeting of the Pharmaceutical Society of Japan, p. 222 (1990).Google Scholar
  191. 191.
    Hatano, T., R. Kira, M. Yoshizaki, and T. Okuda: Seasonal Changes in the Tannins of Liquidambar formosana Reflecting Their Biogenesis. Phytochem. 25, 2787 (1986).Google Scholar
  192. 192.
    Moumou, Y., F. Trotin, J. Dubois, J. Vasseur, and E. El-Boustani: Influence of Culture Condition on Polyphenol Production by Fagopyrum esculentum Tissue Cultures. J. Nat. Prod. 55, 33 (1992).Google Scholar
  193. 193.
    Moumou, Y., J. Vasseur, F. Trotin, and J. Dubois: Catechin Production by Callus Cultures of Fagopyrum esculentum. Phytochem. 31, 1239 (1992).Google Scholar
  194. 194.
    Yazaki, K., and T. Okuda: Procyanidins in Callus and Multiple Shoot Cultures of Hypericum erectum Thunb. Planta Med. 56, 490 (1990).Google Scholar
  195. 195.
    Yazaki, K., and T. Okuda: Condensed Tannin Production in Callus and Suspension Cultures of Cinnamomum cassia Blume. Phytochem. 29, 1559 (1990).Google Scholar
  196. 196.
    Yazaki, K., and T. Okuda: Gallotannin Production in Cell Cultures of Cornus officinalis Sieb, et Zucc. Plant Cell Rep. 8, 346 (1989).Google Scholar
  197. 197.
    Yazaki, K., and T. Okuda: Cornus officinalis: In vitro Culture and the Production of Gallotannins. In: Biotechnology in Agriculture and Biochemistry, Vol. 21: Medicinal and Aromatic Plants, IV (Y. P. Bajaj ed.), p. 104. Berlin-Heidelberg-New York: Springer. 1993.Google Scholar
  198. 198.
    Yazaki, K., and T. Okuda: Ellagitannin Formation in Callus Cultures of Heterocentron roseum. Phytochem. 29, 1127 (1990).Google Scholar
  199. 199.
    Ishimaru, K., and K. Shimomura: Tannin Production in Hairy Root Culture of Geranium thunbergii. Phytochem. 30, 825 (1991).Google Scholar
  200. 200.
    Hatano, T., T. Yoshida, and T. Okuda: Chromatography of Tannins, III: Multiple Peaks in High-performance Liquid Chromatography of Some Hydrolyzable Tannins. J. Chromatogr. 435, 285 (1988).Google Scholar
  201. 201.
    Ishimaru, K., M. Hirose, K. Takahashi, K. Koyama, and K. Shimomura: Tannin Production in Root Culture of Sanguisorba officinalis. Phytochem. 29, 3827 (1990).Google Scholar
  202. 202.
    Mayer, W., E.H. Hoffmann, N. Lösch, H. Wolf, B. Wolter, and G. Schilling: Dehydrierungsreaktionen mit Gallussäureestern. Liebigs Ann. Chem. 1984, 929.Google Scholar
  203. 203.
    Yoshida, T., K. Mori, T. Hatano, T. Okumura, I. Uehara, K. Komagoe, Y. Fujita, and T. Okuda: Studies on Inhibition Mechanism of Autoxidation by Tannins and Flavonoids, V: Radical-Scavenging Effects of Tannins and Related Polyphenols on l,l,-Diphenyl-2-picrylhydrazyl Radical. Chem. Pharm. Bull. (Japan) 37, 1919 (1989).Google Scholar
  204. 204.
    Feldman, K.S., and S.M. Ensel: Ellagitannin Chemistry. The First Example of Biomimetic Diastereoselective Oxidative Coupling of a Glucose-Derived Digalloyl Substrate. J. Am. Chem. Soc. 115, 1162 (1993).Google Scholar
  205. 205.
    Okuda, T., T. Yoshida, and T. Hatano: Antioxidant Effects of Tannins and Related Polyphenols. In: Phenolic Compounds in Food and Their Effects on Health, II (M.-T. Huang, C.-T. Ho, and C.Y. Lee, eds.), p. 87. Washington, DC: American Chemical Society. 1992.Google Scholar
  206. 206.
    Okuda, T., T. Yoshida, and T. Hatano: Polyphenols from Asian Plants: Structural Diversity and Antitumor and Antiviral Activities. In: Phenolic Compounds in Food and Their Effects on Health, II (M.-T. Huang, C.-T. Ho, and C.Y. Lee, eds.), p. 160. Washington, DC: American Chemical Society. 1992.Google Scholar
  207. 207.
    Okuda, T., T. Yoshida, and T. Hatano: Antioxidant Phenolics in Oriental Medicine. In: Active Oxygens, Lipid Peroxides, and Antioxidants (K. Yagi, ed.), p. 333. Tokyo: Japan Sci. Soc. Press/Boca Raton: CRC Press. 1993.Google Scholar
  208. 208.
    Okuda, T., T. Yoshida, and T. Hatano: Chemistry and Antioxidant Effects of Phenolics from Licorice, Tea and Composite and Labiate Herbs. In: Food Phytochemicals for Cancer Prevention, II (C.-T. Ho, T. Osawa, M.-T. Huang, and R.T. Rosen, eds.), p. 133. Washington, DC: American Chemical Society. 1992.Google Scholar
  209. 209.
    Okuda, T., T. Yoshida, and T. Hatano: Antioxidant Polyphenols in Oriental Medicine. In: Proceedings of 5th International Congress on Oxygen Radicals ( K. Yagi, ed.). Tokyo: Publication Center for Academic Societies, Japan (1993).Google Scholar
  210. 210.
    Yoshida, T., S. Koyama, and T. Okuda: Inhibitory Effects of Tannins on Cupric Ion-catalyzed Autoxidation of Ascorbic Acid. Yakugaku Zasshi 101, 695 (1981).Google Scholar
  211. 211.
    Fujita, Y., K. Komagoe, Y. Sasaki, I. Uehara, T. Okuda, and T. Yoshida: Inhibition Mechanism of Tannins on Cu(II)-Catalyzed Oxidation of Ascorbic Acid. Yakugaku Zasshi 107, 17 (1987).Google Scholar
  212. 212.
    Okuda, T., Y. Kimura, T. Yoshida, T. Hatano, H. Okuda, and S. Arichi: Studies on the Activities of Tannins and Related Compounds, I: Inhibitory Effects on Lipid Peroxidation in Mitochondria and Microsomes of Liver. Chem. Pharm. Bull. (Japan) 31, 1625 (1983).Google Scholar
  213. 213.
    Kimura, Y., H. Okuda, T. Okuda, T. Hatano, I. Agata, and S. Arichi: Inhibitory Effects on Lipid Peroxidation in Mitochondria and Microsomes of Liver. Planta Med. 50, 459 (1984).Google Scholar
  214. 214.
    Kimura, Y., H. Okuda, K. Mori, T. Okuda, and S. Arichi: Effects of Various Extracts of Geranii Herba and Geraniin on Liver Injury and Lipid Metabolism in Rats Fed Peroxidized Oil. Chem. Pharm. Bull. (Japan) 32, 1866 (1984).Google Scholar
  215. 215.
    Kimura, Y., H. Okuda, T. Okuda, T. Hatano, I. Agata, and S. Arichi: Effects of Extracts of Leaves of Artemisia Species, and Caffeic Acid and Chlorogenic Acid on Lipid Metabolic Injury in Rats Fed Peroxidized Oil. Chem. Pharm. Bull. (Japan) 33, 2028 (1985).Google Scholar
  216. 216.
    Fujita, Y., K. Komagoe, Y. Niwa, I. Uehara, R. Hara, H. Mori, and T. Okuda: Inhibition Mechanism of Tannins Isolated from Medicinal Plants and Related Com-pounds on Autoxidation of Methyl Linoleate. Yakugaku Zasshi 108, 528 (1988).Google Scholar
  217. 217.
    Hatano, T., H. Kagawa, T. Yasuhara, and T. Okuda: Two New Flavonoids and other Constituents in Licorice Root: Their Relative Astringency and Radical Scavenging Effects. Chem. Pharm. Bull. (Japan) 36, 2090 (1988).Google Scholar
  218. 218.
    Hatano, T., R. Edamatsu, M. Hiramatsu, A. Mori, Y. Fujita, T. Yasuhara, T. Yoshida, and T. Okuda: Effects of Tannins and Related Polyphenols on Superoxide Anion Radical, and on l,l-Diphenyl-2-picrylhydrazyl Radical. Chem. Pharm. Bull. (Japan) 37, 2016 (1989).Google Scholar
  219. 219.
    Hikino, H., Y. Kiso, T. Hatano, T. Yoshida, and T. Okuda: Antihepatotoxic Actions of Tannins. J. Ethnopharmacol. 14, 19 (1985).Google Scholar
  220. 220.
    Kimura, Y., H. Okuda, T. Okuda, and S. Arichi: Effects of Geraniin, Corilagin, and Ellagic Acid Isolated from Geranii Herba on Arachidonate Metabolism in Leukocytes. Planta Med. 52, 337 (1986).Google Scholar
  221. 221.
    Kimura, Y., H. Okuda, T. Okuda, T. Hatano, and S. Arichi: Effects of Caffetannins and Related Compounds on Arachidonate Metabolism in Human Polymorphonuclear Leukocytes. J. Nat. Prod. 50, 392 (1987).Google Scholar
  222. 222.
    Kimura, Y., H. Okuda, T. Okuda, and S. Arichi: Effects of Chalcones Isolated from Licorice Roots on Leukotriene Biosynthesis in Human Polymorphonuclear Neutrophils. Phytother. Res. 2, 140 (1988).Google Scholar
  223. 223.
    Fujita, Y., I. Uehara, Y. Morimoto, M. Nakashima, T. Hatano, and T. Okuda: Inhibition Mechanism of Caffetannins Isolated from Leaves of Artemisia Species on Lipoxygenase Dependent Lipid Peroxidation. Yakugaku Zasshi 108, 129 (1988).Google Scholar
  224. 224.
    Iwata, S., Y. Fukaya, K. Nakazawa, and T. Okuda: Effects of Tannins on the Oxidative Damage of Mouse Ocular Lens, I. J. Ocular Pharmacol. 3, 227 (1987).Google Scholar
  225. 225.
    Fukaya Y., K. Nakazawa, T. Okuda, and S. Iwata: Effect of Tannin on Oxidative Damage of Ocular Lens. Jpn. J. Ophthalmol. 32, 166 (1988).Google Scholar
  226. 226.
    Hatano, T., T. Yasuhara, T. Fukuda, T. Noro, and T. Okuda: Structures of Licopyranocoumarin, Licoarylcoumarin and Glisoflavone, and Inhibitory Effects of Licorice Phenolics and Xanthine Oxidase. Chem. Pharm. Bull. (Japan) 37, 3005 (1989).Google Scholar
  227. 227.
    Hatano, T., T. Yasuhara, R. Yoshihara, I. Agata, T. Noro, and T. Okuda: Inhibitory Effects of Tannins and Related Polyphenols on Xanthine Oxidase. Chem. Pharm. Bull. (Japan) 38, 1224 (1990).Google Scholar
  228. 228.
    Hatano, T., T. Fukuda, T. Miyase, T. Noro, and T. Okuda: Structures of Glicoricone and Licofuranone, and Inhibitory Effects of Licorice Constituents on Monoamine Oxidase. Chem. Pharm. Bull. (Japan) 39, 1238 (1991).Google Scholar
  229. 229.
    Chen, G.: The Pathobiology of Parkinson’s Disease: Biochemical Aspects of Dopamine Neuron Senescence. J. Neural. Transm., Suppl. 19, 89 (1983).Google Scholar
  230. 230.
    Morton, J. F.: Widespread Tannin Intake via Stimulants and Masticatories, Especially Guarana, Kola Nut, Betel Vine, and Accessories. In: Plant Polyphenols, Synthesis, Properties, Significance (R. W. Hemingway and P. E. Laks, eds.), p. 739. New York: Plenum Press. 1992.Google Scholar
  231. 231.
    Hirose, M., S. Fukushima, T. Shirai, R. Hasegawa, T. Kato, H. Tanaka, E. Asakawa, and N. Ito: Stomach Carcinogenicity of Caffeic Acid, Sesamol and Catechol in Rats and Mice. Jpn. J. Cancer Res. 81, 207 (1990).Google Scholar
  232. 232.
    Okuda, T., K. Mori, and H. Hayatsu: Inhibitory Effects of Tannins and Related Compounds on Mutagenic Substances (2). Abstract Papers of the 102nd Annual Meeting of Pharmaceutical Society of Japan, p. 588 (1982).Google Scholar
  233. 233.
    Okuda, T., K. Mori, and H. Hayatsu: Inhibitory Effect of Tannins on Direct-acting Mutagens. Chem. Pharm. Bull. (Japan) 32, 3755 (1984).Google Scholar
  234. 234.
    Sayer, J. M., H. Yagi, A. W. Wood, A.H. Conney, and D.M. Jerina: Extremely Facile Reaction Between the Ultimate Carcinogen Benzo[a]pyrene 7,8-Diol-9,10-epoxide and Ellagic Acid. J. Am. Chem. Soc. 104, 5562 (1982).Google Scholar
  235. 235.
    Okuda, T., K. Mori, and M. Ishino: Studies on the Constituents of Geranium thunbergii, Part 8: Transformations of Geraniin upon Decoction. Yakugaku Zasshi 99, 505 (1979).Google Scholar
  236. 236.
    Daniel, E. M., S. Ratnayake, T. Kinstle, and G. D. Stoner: The Effects of pH and Rat Intestinal Contents on the Liberation of Ellagic Acid from Purified and Crude Ellagitannins. J. Nat. Prod. 54, 946 (1991).Google Scholar
  237. 237.
    Huang, M.-T, R. L. Chang, A. W. Wood, H. L. Newmark, J. M. Sayer, H. Yagi, D.M. Jerina, and A. H. Conney: Inhibition of the Mutagenicity of Bay-region Diol-epoxide of Polycyclic Aromatic Hydrocarbons by Tannic Acid, Hydroxylated Anthraquinones and Hydroxylated Cinnamic Acid Derivatives. Carcinogenesis 6, 237 (1985).Google Scholar
  238. 238.
    Kashiwada, Y., G. Nonaka, I. Nishioka, J.-J. Chang, and K.-H. Lee: Tannins and Related Compounds as Selective Cytotoxic Agents. J. Nat. Prod. 55, 1033 (1992).Google Scholar
  239. 239.
    Yoshizawa, S., T. Horiuchi, H. Fujiki, T. Yoshida, T. Okuda, and T. Sugimura: Antitumor Promoting Activity of (−)-Epigallocatechin Gallate, the Main Constituent of “Tannin” in Green Tea. Phytother. Res. 1, 44 (1987).Google Scholar
  240. 240.
    Fujiki, H., M. Suganuma, S. Yoshizawa, J. Yatsunami, S. Nishiwaki, H. Furuya, S. Okabe, R. Nishiwaki-Matsushima, S. Matsunaga, Y. Muto, T. Okuda, and T. Sugimura: Sarcophytol A and (−)-Epigallocatechin Gallate (EGCG), Nontoxic In-hibitors of Cancer Development. In: Cancer Chemoprevention (L. Wattenberg, M. Lipkin, C.W. Boone, and G.J. Kelloff, eds.), p. 393. Boca Raton: CRC Press. 1992.Google Scholar
  241. 241.
    Fujita, Y., T. Yamane, M. Tanaka, K. Kuwata, J. Okuzumi, T. Takahashi, H. Fujiki, and T. Okuda: Inhibitory Effect of (−)-Epigallocatechin Gallate on Carcinogenesis with N-ethyl-N’-nitro-N-nitrosoguanidine in Mouse Duodenum. Jpn. J. Cancer Res. 80, 503 (1989).Google Scholar
  242. 242.
    Komori, A., J. Yatsunami, S. Okabe, S. Abe, K. Hara, M. Suganuma, S. Kim, and H. Fujiki: Anticarcinogenic Activity of Green Tea Polyphenols. Jpn. J. Clin. Oncol. 23, 186 (1993).Google Scholar
  243. 243.
    Wang, Z.-Y., M.-T. Huang, T. Ferraro, C.-Q. Wong, Y.R. Lou, K. Reuhl, M. Iatropoulos, C. S. Yang, and A. H. Conney: Inhibitory Effect of Green Tea in the Drinking Water on Tumorigenesis by Ultraviolet Light and 12-O-Tetradecanoyl- phorbol-13-acetate in the Skin of SKH-1 Mice. Cancer Res. 52, 1162 (1992).Google Scholar
  244. 244.
    Miyamoto, K., N. Kishi, R. Koshiura, T. Yoshida, T. Hatano, and T. Okuda: Relationship Between the Structures and the Antitumor Activities of Tannins. Chem. Pharm. Bull. (Japan) 35, 814 (1987).Google Scholar
  245. 245.
    Miyamoto, K., M. Sasakura, E. Matsui, R. Koshiura, T. Murayama, T. Hatano, T. Yoshida, and T. Okuda: Antitumor Activity of Oenothein B, a Unique Macrocyclic Ellagitannin. Jpn. J. Cancer Res. 84, 99 (1993).Google Scholar
  246. 246.
    Miyamoto, K., M. Nomura, T. Murayama, T. Furukawa, T. Hatano, T. Yoshida, R. Koshiura, and T. Okuda: Antitumor Activities of Ellagitannins Against Sarcoma- 180 in Mice. Biol. Pharm. Bull. 16, 379 (1993).Google Scholar
  247. 247.
    Miyamoto, K., T. Murayama, M. Nomura, T. Hatano, T. Yoshida, T. Furuya, R. Koshiura, and T. Okuda: Antitumor Activity and Interleukin-1 Induction by Tannins. Anticancer Res. 31, 37 (1993).Google Scholar
  248. 248.
    Asanaka, M., T. Kurimura, R. Koshiura, T. Okuda, M. Mori, and H. Yokoi: Inhibitory Effect of Ellagitannins on the in vitro Replication of Human Immunodeficiency Virus (HIV). AIDS Research Newsletter 1, 72 (1987).Google Scholar
  249. 249.
    Hatano, T., T. Yasuhara, K. Miyamoto, and T. Okuda: Anti-Human Immunodefi-ciency Virus Phenolics from Licorice. Chem. Pharm. Bull. (Japan) 36, 2286 (1988).Google Scholar
  250. 250.
    Nakashima, H., T. Murakami, N. Yamamoto, H. Sakagami, S. Tanuma, T. Hatano, T. Yoshida, and T. Okuda: Inhibition of Human Immunodeficiency Viral Replication by Tannins and Related Compounds. Antiviral Res. 18, 91 (1992).Google Scholar
  251. 251.
    Takechi, M., Y. Tanaka, M. Takehara, G. Nonaka, and I. Nishioka: Structure and Antiherpetic Activity Among the Tannins. Phytochem. 24, 2245 (1985).Google Scholar
  252. 252.
    Kakiuchi, N., M. Hattori, T. Namba, M. Nishizawa, T. Yamagishi, and T. Okuda: Inhibitory Eifects of Tannins on Reverse Transcriptase from RNA Tumor Virus. J. Nat. Prod. 48, 614 (1985).Google Scholar
  253. 253.
    Nishizawa, M., T. Yamagishi, G. E. Dutchman, W. B. Parker, A.J. Bodner, R. E. Kilkuskie, Y.-C. Cheng, and K.-H. Lee: Isolation and Characterization of Four New Tetragalloylquinic Acids as a New Class of HIV Reverse Transcriptase Inhibitors from Tannic Acid. J. Nat. Prod. 52, 762 (1989).Google Scholar
  254. 254.
    Nonaka, G., I. Nishioka, M. Nishizawa, T. Yamagishi, Y. Kashiwada, G.E. Dutchman, A.J. Bodner, R.E. Kilkuskie, Y.-C. Cheng, and K.-H. Lee: Inhibitory Effects of Tannins on HIV Reverse Transcriptase and HIV Replication in H9 Lymphocyte Cells. J. Nat. Prod. 53, 587 (1990).Google Scholar
  255. 255.
    Kakiuchi, N., X. Wang, M. Hattori, T. Okuda, and T. Namba: Circular Dichroism Studies on the Ellagitannins-Nucleic Acids Interaction. Chem. Pharm. Bull. (Japan) 35, 2875 (1987).Google Scholar
  256. 256.
    Kakiuchi, N., M. Hattori, M. Nishizawa, T. Yamagishi, T. Okuda, and T. Namba: Inhibitory Effect of Various Tannins on Glucan Synthesis by Glucosyltransferase from Streptococcus mutans. Chem. Pharm. Bull. (Japan) 34, 720 (1986).Google Scholar
  257. 257.
    Kimura, Y., H. Okuda, T. Okuda, T. Yoshida, T. Hatano, and S. Arichi: Effects of Various Tannins and Related Compounds on Adrenaline-induced Lipolysis in Fat Cells. Chem. Pharm. Bull. (Japan) 31, 2497 (1983).Google Scholar
  258. 258.
    Kimura, Y., H. Okuda, T. Okuda, T. Yoshida, T. Hatano, and S. Arichi: Effects of Various Tannins and Related Compounds on Adrenocorticotropic Hormone-induced Lipolysis and Insulin-induced Lipogenesis from Glucose in Fat Cells. Chem. Pharm. Bull. (Japan) 31, 2501 (1983).Google Scholar
  259. 259.
    Hatano, T., T. Okuda, Y. Fujita, Y. Kimura, H. Okuda, and S. Arichi: Effects of Tannins Suppressing Lipid-peroxidation, and Their Effects on Fat Cells. J. Med. Pharm. Soc. Wakan-Yaku 1, 40 (1984).Google Scholar
  260. 260.
    Hatano, T., T. Okuda, Y. Fujita, Y. Kimura, H. Okuda, and S. Arichi: Effects of Caffetannins of Arachidonate Metabolism. J. Med. Pharm. Soc. Wakan-Yaku 4, 350 (1987).Google Scholar
  261. 261.
    Okuda, T., K. Mori, M. Shiota, and K. Ida: Reduction of Heavy Metal Ions and Solubilization of Precipitates. Yakugaku Zasshi 102, 735 (1982).Google Scholar
  262. 262.
    Okuda, T., K. Mori, and M. Shiota: Effects of the Interaction of Tannins with Co-existing Substances, Part 3: Formation and Solubilization of Precipitates with Alkaloids. Yakugaku Zasshi 102, 854 (1982).Google Scholar
  263. 263.
    Kimura, Y., H. Okuda, T. Okuda, T. Hatano, I. Agata, and S. Arichi: Studies on the Activities of Tannins and Related Compounds from Medicinal Plants and Drugs, VI: Inhibitory Effects of Caffeoylquinic Acids on Histamine Release from Rat Peritoneal Mast Cells. Chem. Pharm. Bull. (Japan) 33, 690 (1985).Google Scholar
  264. 264.
    Booth, A. N., M. S. Masri, D. J. Robbins, O. H. Emerson, F. T. Jones, and F. Deeds: The Metabolic Fate of Gallic Acid and Related Compounds. J. Biol. Chem. 234, 3014 (1959).Google Scholar
  265. 265.
    Doyle, B., and L.A. Griffiths: The Metabolism of Ellagic Acid in the Rat. Xenobiotica 10, 247 (1980).Google Scholar
  266. 266.
    Okuda, T., T. Hatano, M. Matsuda, and P. B. English: Studies on the Adsorption and the Metabolism of Tannins, I: A New Tannin and Related Compounds from Terminalia Species. Abstract Papers of the 32nd Annual Meeting of the Japanese Society of Pharmacognosy, p. 9 (1985).Google Scholar

Copyright information

© Springer-Verlag/Wien 1995

Authors and Affiliations

  • Takuo Okuda
    • 1
  • Takashi Yoshida
    • 1
  • Tsutomu Hatano
    • 1
  1. 1.Faculty of Pharmaceutical SciencesOkayama UniversityTsushima, Okayama 700Japan

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