Skip to main content
SpringerLink
Log in
Book cover

Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products pp 1–117Cite as

Hydrolyzable Tannins and Related Polyphenols

  • Chapter

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.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Okuda, T., T. Yoshida, and T. Hatano: New Methods of Analyzing Tannins. J. Nat. Prod. 52, 1 (1989).

    CAS  Google Scholar 

  2. Haslam, E.: The Metabolism of Gallic Acid and Hexahydroxydiphenic Acid in Higher Plants. Fortschritte Chem. Org. Naturst. 41, 1 (1982).

    CAS  Google Scholar 

  3. Haslam, E.: Plant Polyphenols, Vegetable Tannins Revisited. Cambridge: Cambridge University Press. 1989.

    Google Scholar 

  4. Okuda, T., T. Yoshida, and T. Hatano: Oligomeric Hydrolyzable Tannins, a New Class of Plant Polyphenols. Heterocycles 30, 1995 (1990).

    Google Scholar 

  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).

    CAS  Google Scholar 

  6. Okuda, T., T. Yoshida, and T. Hatano: Classification of Oligomeric Hydrolyzable Tannins and Specificity of Their Occurrence in Plants. Phytochem. 32, 507 (1993).

    CAS  Google Scholar 

  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. Okuda, T., T. Yoshida, and T. Hatano: Ellagitannins as Active Constituents of Medicinal Plants. Planta Med. 55, 117 (1989).

    CAS  Google Scholar 

  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. 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. Schmidt, O.Th., and G. Klinger: Über natürliche Gerbstoffe, XXYIII: Synthese der 1,3,6-Trigalloylglucose. Liebigs Ann. Chem. 609, 199 (1957).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. Delahaye, P., A. De Bruyn, F. Van Damme, and M. Verzele: Trigallic Acid or Trimeric Gallic Acid. Bull. Soc. Chim. Belg. 92, 469 (1983).

    CAS  Google Scholar 

  15. Mayer, W., N. Kunz, and F. Loebich: Die Struktur Hamamelitannins. Liebigs Ann. Chem. 688, 232 (1965).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  19. Nishimura, H., G. Nonaka, and I. Nishioka: Scyllo-quercitol Gallates and Hexa-hydroxydiphenoates from Quercus stenophylla. Phytochem. 25, 2599 (1986).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. Bock, K., F. N. Lacour, R. S. Jensen, and B. J. Nielsen: The Structure of Acertannin. Phytochem. 19, 2033 (1980).

    CAS  Google Scholar 

  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. 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. 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).

    CAS  Google Scholar 

  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. 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. 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).

    CAS  Google Scholar 

  29. Kashiwada, Y., G. Nonaka, and I. Nishioka: Galloylsucroses from Rhubarb. Phytochem. 27, 1469 (1988).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  31. Ji, S.-H., N. Saito, M. Yokoi, A. Shigihara, and T. Honda: Galloylcyanidin Glycosides from Acer. Phytochem. 31, 655 (1992).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  34. Chen, X.-M., T. Yoshida, T. Hatano, M. Fukushima, and T. Okuda: Galloylarbutin and Other Polyphenols from Bergenia purpurascens. Phytochem. 26, 515 (1987).

    CAS  Google Scholar 

  35. Yazaki, K., S. Shida, and T. Okuda: Galloylhomoarbutin and Related Polyphenols from Pyrola incarnata. Phytochem. 28, 607 (1989).

    CAS  Google Scholar 

  36. Nonaka, G., I. Nishioka, T. Nagasawa, and H. Oura: Tannins and Related Compounds, I: Rhubarb (1). Chem. Pharm. Bull. (Japan) 29, 2862 (1981).

    CAS  Google Scholar 

  37. Ishimaru, K., G. Nonaka, and I. Nishioka: Phenolic Glucoside Gallates from Quercus mongolica and Q. acutissima. Phytochem. 26, 1147 (1987).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  43. Yoshida, T., K. Seno, Y. Takama, and T. Okuda: Bergenin Derivatives from Mallotus japonicus. Phytochem. 21, 1180 (1982).

    CAS  Google Scholar 

  44. Saijo, R., G. Nonaka, and I. Nishioka: Gallic Acid Esters of Bergenin and Norbergenin from Mallotus japonicus. Phytochem. 29, 267 (1990).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  48. Hatano, T., K. Urita, and T. Okuda: Tannins from Saxifraga stronifera. J. Med. Pharm. Soc. Wakan-Yaku 3, 434 (1986).

    Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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. Wilkins, C.K., and B.A. Böhm: Ellagitannins from Tellima grandiflora. Phytochem. 15, 211 (1976).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  68. Okuda, T., T. Yoshida, T. Hatano, K. Yazaki, and M. Ashida: Ellagitannins of Casuarinaceae, Stachyuraceae and Myrtaceae. Phytochem. 21, 2871 (1982).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. Okuda, T., K. Mori, and T. Hatano: The Distribution of Geraniin and Mallotusinic Acid in the Order Geraniales. Phytochem. 19, 547 (1980).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. Schmidt, O. Th., J. Schulz, and R. Wurmb: Terchebin. Liebigs Ann. Chem. 706, 169 (1967).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  76. Fürstenwerth, H., and H. Schildknecht: Isoterchebin, der gelbe Farbstoff des Zistrosenwürgers Cytinus hypocistis ( Rafflesiaceae, Schmarotzerblumengewächse). Liebigs Ann. Chem. 1976, 112.

    Google Scholar 

  77. Okuda, T., T. Hatano, and T. Yasui: Revised Structure of Isoterchebin, Isolated from Cornus officinalis. Heterocycles 16, 1681 (1981).

    CAS  Google Scholar 

  78. Okuda, T., T. Yoshida, K. Mori, and T. Hatano: Tannins of Medicinal Plants and Drugs. Heterocycles 15, 1323 (1981).

    CAS  Google Scholar 

  79. Okuda, T., and K. Seno: Mallotusinic Acid and Mallotinic Acid, New Hydrolyzable Tannins from Mallotus japonicus. Tetrahedron Lett. 1978, 139.

    Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  89. Yoshida, T., R. Fujii, and T. Okuda: Revised Structures of Chebulinic Acid and Chebulagic Acid. Chem. Pharm. Bull. (Japan) 28, 3713 (1980).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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. 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. 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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. Okuda, T., T. Yoshida, and T. Hatano: Biomimetic Synthesis of Elaeocarpusin. Heterocycles 24, 1841 (1986).

    CAS  Google Scholar 

  99. Foo, L.Y., and H. Wong: Phyllanthusiin D, an Unusual Hydrolysable Tannin from Phyllanthus amarus. Phytochem. 31, 711 (1992).

    CAS  Google Scholar 

  100. Yazaki, K., T. Yoshida, and T. Okuda: Tannin Production in Cell Suspension Cultures of Geranium thunbergii. Phytochem. 30, 501 (1991).

    CAS  Google Scholar 

  101. Mayer, W.: Über die Gerbstoffe aus dem Holz der Edelkastanie und Eiche. Das Leder 22, 277 (1971).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  111. Tanaka, T., G. Nonaka, I. Nishioka, I. Kouno, and F.-C. Ho: Dehydroellagitannin from Bishofia javanica. Phytochem. 38, 509 (1995).

    CAS  Google Scholar 

  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. 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. 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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  116. Yoshida, T., Z.-X. Jin, and T. Okuda: Hydrolyzable Tannin Oligomers from Rosa davurica. Phytochem. 30, 2747 (1991).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  122. Yoshida, T., Z.-X. Jin, and T. Okuda: Unpublished data.

    Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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. 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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  148. Yoshida, T., F. Nakata, K. Hosotani, A. Nitta, and T. Okuda: Tannins from Melastoma malabathricum. Phytochem. 31, 2829 (1992).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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. 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. Yoshida, T., A.F. Ahmed, and T. Okuda: Tamarixinins B and C, Dimeric Hydrolyz-able Tannins from Tamarix pakistanica. Phytochem. 33, 197 (1993).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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. 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. 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).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  167. Bate-Smith, E.C.: Detection and Determination of Ellagitannins. Phytochem. 11, 1153 (1972).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  174. Yoshida, T., T. Hatano, T. Kuwajima, and T. Okuda: Oligomeric Hydrolyzable Tannins and Their 1HNMR Spectra and Partial Degradation. Heterocycles 33, 463 (1992).

    CAS  Google Scholar 

  175. Cronquist, A.: The Evolution and Classification of Flowering Plants, 2nd Ed. New York: The New York Botanical Garden. 1988.

    Google Scholar 

  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).

    CAS  Google Scholar 

  177. Okuda, T., T. Hatano, T. Kaneda, M. Yoshizaki, and T. Shingu: Liquidambin, a New Ellagitannin from Liquidambar formosana. Phytochem. 26, 2053 (1987).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  180. Merfort, I.: Caffeoylquinic Acids from Flowers of Arnica montana and Arnica chamissonis. Phytochem. 31, 2111 (1992).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  183. Hegnauer, R.: Chemotaxonomie der Pflanzen, Bd. 4, p. 327. Basel-Stuttgart: Birkhäuser. 1966.

    Google Scholar 

  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. 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. 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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  188. Agata, T., T. Hatano, S. Nishibe, and T. Okuda: A Tetrameric Derivative of Caffeic Acid from Rabdosia japonica. Phytochem. 28, 2447 (1989).

    CAS  Google Scholar 

  189. Nishizawa, M., M. Tsuda, and K. Hayashi: Two Caffeic Acid Tetramers Having Enantiomeric Phenyldihydronaphthalene Moieties from Macrotomia euchroma. Phytochem. 29, 2645 (1990).

    CAS  Google Scholar 

  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. Hatano, T., R. Kira, M. Yoshizaki, and T. Okuda: Seasonal Changes in the Tannins of Liquidambar formosana Reflecting Their Biogenesis. Phytochem. 25, 2787 (1986).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  193. Moumou, Y., J. Vasseur, F. Trotin, and J. Dubois: Catechin Production by Callus Cultures of Fagopyrum esculentum. Phytochem. 31, 1239 (1992).

    CAS  Google Scholar 

  194. Yazaki, K., and T. Okuda: Procyanidins in Callus and Multiple Shoot Cultures of Hypericum erectum Thunb. Planta Med. 56, 490 (1990).

    CAS  Google Scholar 

  195. Yazaki, K., and T. Okuda: Condensed Tannin Production in Callus and Suspension Cultures of Cinnamomum cassia Blume. Phytochem. 29, 1559 (1990).

    CAS  Google Scholar 

  196. Yazaki, K., and T. Okuda: Gallotannin Production in Cell Cultures of Cornus officinalis Sieb, et Zucc. Plant Cell Rep. 8, 346 (1989).

    CAS  Google Scholar 

  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. Yazaki, K., and T. Okuda: Ellagitannin Formation in Callus Cultures of Heterocentron roseum. Phytochem. 29, 1127 (1990).

    CAS  Google Scholar 

  199. Ishimaru, K., and K. Shimomura: Tannin Production in Hairy Root Culture of Geranium thunbergii. Phytochem. 30, 825 (1991).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  201. Ishimaru, K., M. Hirose, K. Takahashi, K. Koyama, and K. Shimomura: Tannin Production in Root Culture of Sanguisorba officinalis. Phytochem. 29, 3827 (1990).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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. 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. 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. 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. Yoshida, T., S. Koyama, and T. Okuda: Inhibitory Effects of Tannins on Cupric Ion-catalyzed Autoxidation of Ascorbic Acid. Yakugaku Zasshi 101, 695 (1981).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  219. Hikino, H., Y. Kiso, T. Hatano, T. Yoshida, and T. Okuda: Antihepatotoxic Actions of Tannins. J. Ethnopharmacol. 14, 19 (1985).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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. 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).

    CAS  Google Scholar 

  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. Okuda, T., K. Mori, and H. Hayatsu: Inhibitory Effect of Tannins on Direct-acting Mutagens. Chem. Pharm. Bull. (Japan) 32, 3755 (1984).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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. Hatano, T., T. Yasuhara, K. Miyamoto, and T. Okuda: Anti-Human Immunodefi-ciency Virus Phenolics from Licorice. Chem. Pharm. Bull. (Japan) 36, 2286 (1988).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  251. Takechi, M., Y. Tanaka, M. Takehara, G. Nonaka, and I. Nishioka: Structure and Antiherpetic Activity Among the Tannins. Phytochem. 24, 2245 (1985).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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. 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. Okuda, T., K. Mori, M. Shiota, and K. Ida: Reduction of Heavy Metal Ions and Solubilization of Precipitates. Yakugaku Zasshi 102, 735 (1982).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  265. Doyle, B., and L.A. Griffiths: The Metabolism of Ellagic Acid in the Rat. Xenobiotica 10, 247 (1980).

    CAS  Google Scholar 

  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 

Download references

Author information

Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Okayama University, Tsushima, Okayama 700, Japan

    Takuo Okuda, Takashi Yoshida & Tsutomu Hatano

Authors
  1. Takuo Okuda
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Takashi Yoshida
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tsutomu Hatano
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Chemistry, The Florida State University, Tallahassee, Florida, USA

    W. Herz

  2. Chemistry Department, The University, Glasgow, Scotland

    G. W. Kirby

  3. Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii, USA

    R. E. Moore

  4. Institut für Organische Chemie, Universität München, München, Federal Republic of Germany

    W. Steglich

  5. Institute für Organische Chemie, Universität Basel, Basel, Switzerland

    Ch. Tamm

Rights and permissions

Reprints and permissions

Copyright information

© 1995 Springer-Verlag/Wien

About this chapter

Cite this chapter

Okuda, T., Yoshida, T., Hatano, T. (1995). Hydrolyzable Tannins and Related Polyphenols. In: Herz, W., Kirby, G.W., Moore, R.E., Steglich, W., Tamm, C. (eds) Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 66. Springer, Vienna. https://doi.org/10.1007/978-3-7091-9363-1_1

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-9363-1_1

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-9365-5

  • Online ISBN: 978-3-7091-9363-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation