Tannins and Related Compounds from Medicinal Plants of Africa

Medicinal Plant Research in Africa: Pharmacology and Chemistry

Volumn , Issue , 2013, Pages 479-555

  Shahat, Abdelaaty A ^a,b   Marzouk, Mohamed S ^a,b  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

^b NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

Africa; Biosynthesis; Condensed tannins; Hydrolyzable tannins; Medicinal plants; Pharmacological activity

Indexed keywords

EID: 84902915697     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-12-405927-6.00013-8     Document Type: Chapter

References (252)

1. Hagerman A.E., Carlson D.M. Biological responses to tannins and other polyphenols. Recent Res Dev Agric Food Chem 1998, 2:689-704.
2. Kolodziej H. Isolation, structural identification, NMR-spectroscopy of phenolic compounds. Polyphenols Communications 2000, Freising-Weihenstphan (Germany), September 11-15, 2000; 1: p. 85-6.
3. Haslam E. Natural polyphenols (vegetable tannins) as drugs: possible modes of action. J Nat Prod 1996, 59:205-215.
4. Antonello C. <> (Updated on 17.9.01). http://www.anscLcornell.edu/plants/toxicagents/tannin/definition.htmL.
5. Haslam E., Cai Y. Plant polyphenols (vegetable tannins): gallic acid metabolism. Nat Prod Rep 1994, 11:41-66.
6. Mole S., Waterman P.G. Tannins as antifeedants to mammalian herbivores: still an open question?. Allelochemicals: role in agriculture and forestry 1987, 572-587. American Chemical Society, Washington, DC. G.R. Waller (Ed.).
7. Roberts MT. A dictionary of descriptive terminology. <> (Updated on 7.01.02). http://www.document/Etherington&Roberts%20Dectionarv-Vegetabletannins.htm.
8. Scharffenberger J, Steinberg R. The chocolate paradox, the next red wine?. <> (Updated on 2002). http://www.Scharffenberger.com/library/paradox./.
9. Grundhofer P., Niemetz R., Schilling G., Gross G. Biosynthesis and subcellular distribution of hydrolyzable tannins. Phytochemistry 2001, 57:915-927.
10. Haslam E. Plant polyphenols - vegetable tannins revisited chemistry and pharmacology of natural products 1989, Cambridge University Press, Cambridge, p. 165.
11. Haslam E. Che faro senza polifenoli?. Plant polyphenols 2. "Chemistry, biology, pharmacology, ecology" 1999, 15-40. Kluwer Academic/Plenum Publisher, New York, NY. G.G. Gross, R.W. Hemingway, T. Yoshida (Eds.).
12. Carando S., Teisseder P.L. Catechin and procyanidin levels in French wines: contribution to dietary in take. Plant polyphenols 2. "Chemistry, biology, pharamacology, ecology" 1999, p. 725-37, Kluwer Academic/Plenum Publisher, New York, NY.
13. Gross G.G. Biosynthesis, biodegradation, and cellular localization of hydrolysable tannins. Phytochemistry in human health protection, nutrition and plant defence. Recent advances in phytochemistry 1999, vol. 33. Kluwer Academic/Plenum Publisher, New York, NY.
14. Rohr GE. Analysis of proanthocyanidins. XXth Polyphenols Communications 2000, Freising-Weihenstphan (Germany). In: Martens S, Treutter D, Forkmann G, editors. September 11-15, 2000; p. 60-97.
15. Clifford M.N., Scalbert A. Ellagitannins-nature, occurrence and dietary burden. J Sci Food Agric 2000, 80:1118-1125.
16. Mueller-Harvey I. Analysis of hydrolysable tannins. Anim Feed Sci Technol 2001, 91:3-20.
17. Berlink R.G.S., Hatano T., Okuda T., Yoshida T. Progress in the chemistry of organic natural products 1995, 66. Springer-Verlag, Wien, New York.
18. De Bruyne T., Pieters L., Deelstra H., Vlietinck A. Condensed vegetable tannins: biodiversity in structure and biological activities. Biochem Syst Ecol 1999, 27:445-459.
19. Hatano T., Yasuhara T., Abe R., Okuda T. A galloylated monoterpene glucoside and a dimeric hydrolysable tannin from Cornus officinalis. Phytochemistry 1990, 29:2975-2978.
20. Hou A.-J., Liu Y.-Z., Yang H.H., Lin Z.-W., Sun H.-D. Hydrolyzable tannins and related polyphenols from Eucalyptus globulus. J Asian Nat Prod Res 2000, 2:205-212.
21. Ageta M., Nonaka G.I., Nishioka I. Tannins and related compounds. LXVII. Isolation and characterization of castanopsinins A-H, novel ellagitannins containing a triterpenoid glycoside core, from Castanopsis cuspidate var. sieboldii Nakai. Chem Pharm Bull 1988, 36:1646-1663.
22. Nonaka G., Hayashy M., Tanaka T., Saijo R., Nishioka I. Tannins and related compounds. XCII.: isolation and characterization of Cyanogenic ellagitannins, aleurinins A and B, and a related O-glycosidic ellagitannin, aleurinin C, from Aleurites fordii HEMSLEY. Chem Pharm Bull 1990, 38:861.
23. Okuda T., Yoshida T., Hatano T. Oligomeric hydrolyzable tannins, a new class of plant polyphenols. Heterocycles 1990, 30:1195-1218.
24. Porter L.J. Tannins. Methods in plant biochemistry, vol. 1, plant phenolics 1989, 389-420. Academic Press, London. J.B. Harborne (Ed.).
25. Kashiwada Y., Nonaka G.-I., Nishioka I., Ballas L.M., Jiang J.B., Janzen W.P., et al. Tannins as selective inhibitors of protein kinase C. Bioorg Med Chem Lett 1992, 2:239-244.
26. Kashiwada Y., Nonaka G.-I., Nishioka I., Chang J.-J., Lee K.-H. Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents. J Nat Prod 1992, 55:1033.
27. Khanbabaee K., Teunis van Ree T. Tannins: classification and definition. Nat Prod Rep 2001, 18:641-649.
28. Tanaka T., Tong H.-H., Xu Y.-M., Ishimaru K., Nonaka G.-I., Nishioka I. Tannins and related compounds. CXVII. Isolation and characterization of three new ellagitannins, lagerstannins A, B and C, having a gluconic acid core, from Lagerstroemia speciosa (L.) PERS. Chem Pharm Bull 1992, 40:2975-2980.
29. Ferreira D., Bekker R. Oligomeric proanthocyanidins: naturally occurring O-heterocycles. Nat Prod Rep 1996, 13:411.
30. Itoh A., Tanahashi T., Ikejima S., Inoue M., Nagakura N., Inoue K., et al. Five phenolic glycosides from Alangium chinense. J Nat Prod 2000, 63:95.
31. Saijo R., Nonaka G., Nishioka I. Phenol glucoside gallates from Malloyus japonicas. Phytochemistry 1989, 28:2443-2446.
32. Tanaka T., Sueyasu T., Nonaka G.-I., Nishioka I. Tannins and related compounds. Isolation and characterization of galloyl and p-hydroxybenzoyl ester of benzophenone and xantone C-glucosides from Mangifera indica. Chem Pharm Bull 1984, 32:2676.
33. Ishimaru K., Nonaka G., Nishioka I. Gallic acid esters of proto-quercitol, quinic acid and (-)-shikimic acid from Quercus mongolica and Q. myrsin aefolia. Phytochemistry 1987, 26:1501.
34. Nishimura H., Nonaka G., Nishioka I. Scyllo-quercitol gallates and hexahydroxydiphenoates from Quercus stenophylla. Phytochemistry 1986, 25:2599.
35. Nonaka G., Nishioka I. Tannins and related compounds. 10. Rhubarb. Isolation and structure of a glycerol gallic, gallic acid glucoside gallate and isolindleyin. Chem Pharm Bull 1983, 31:1652.
36. Porter L.J. Flavans and proanthocyanidins. The flavonoids: advances in research since 1986 1994, 23-55. Chapman and Hall, London. J.B. Harborne (Ed.).
37. Xie D.-Y., Dixon R.A. Proanthocyanidin biosynthesis-still more questions than answers?. Phytochemistry 2005, 66:2127-2144.
38. Hemingway R.W., Foo L.Y., Porter L.J. Linkage isomerism in trimeric and polymeric 2,3-cis procyanidins. J Chem Soc Perkin Trans I 1982, 1209.
39. Haslam E. The metabolism of gallic acid and hexahydroxydiphenic acid in higher plants. Fortschr Chem Org Naturst 1982, 41:1.
40. He F., Pan Q.-H., Shi Y., Duan C.-Q. Biosynthesis and genetic regulation of proanthocyanidins in plants. Molecules 2008, 13:2674-2703.
41. Lewis N.G., Yamamoto E. Chemistry and significance of condensed tannins 1989, 23. Plenum Press, New York, NY, Oxford, 1999; 791-7. R.W. Hemingway, J.J. Karchesy (Eds.).
42. Jacques D., Haslam E., Bedford G.R., Greatbanks D. Plant proanthocyanidins. Part 4. Biosynthesis of procyanidins and observations on the metabolism of cyanidin in plants. J Chem Soc Perkin Trans I 1977, 1637.
43. Porter L.J., Ma Z., Chan B.G. Cacao procyanidins: major flavanoids and entification of some minor metabolites. Phytochemistry 1991, 30:1657-1663.
44. De Bruyne T., Pieters L., Deelstra H., Vlietinck A. Condensed vegetable tannins: biodiversity in structure and biological activities. Biochem Syst Ecol 1999, 27:445-459.
45. Osawa T. Neuroprotective effect of wormwood against lead exposure. Mech Ageing Dev 1999, 111:133.
46. Kruedener S.V., Schempp H., Elstner E.F. Gas chromatographic differentiation between myeloperoxidase activity and fenton-type oxidants. Free Radic Biol Med 1995, 19:141.
47. Hippeli S., Dornisch K., Kaiser S., Draeger U., Estner E.F. Biological durability and oxidative potential of a stonewool mineral fiber compared to crocidolite asbestos fiber. Arch Toxicol 1997, 71:532.
48. Schempp H, Weiser D, Elstner EF. Antioxidative activities of plant phenolics. XXth Polyphenols Communications 2000, Freising-Weihenstphan (Germany), In: Martens S, Treutter D, Forkmann G editors. September 11-15, 2000; p. 137-57.
49. Yoshida T., Koyama S., Okuda T. Inhibitory effect of tannins on cupric ion-catalyzed autoxidation of ascorbic acid. Yakugaku Zasshi 1981, 101:695.
50. Fujita Y., Komagoe K., Sasaki Y., Uehara I., Okuda T., Yoshida T. Inhibition mechanism of tannins on Cu(II)-catalyzed autoxidation of ascorbic acid. Yakugaku Zasshi 1987, 107:17.
51. Yoshida T., Okuda H., Okuda T., Hatano T., Agata I., Arichi S. Inhibition mechanism of tannins isolated from medicinal plants and related compounds on autoxidation of methyl linoleate. Planta Med 1984, 50:459.
52. Hatano T., Kagawa H., Yasuhara T., Okuda T. Two new flavonoids and other constituents in licorice root: their relative astringency and radical scavenging effects. Chem Pharm Bull 1988, 36:2090.
53. Hatano T., Edamatsu R., Hiramatsu M., Mori A., Fujita Y., Yasuhara T., et al. Effects of the interaction of tannins with co-existing substances. VI. Effects of tannins and related polyphenols on superoxide anion radical and on 1,1-diphenyl 2-picrylhydrazyl radical. Chem Pharm Bull 1989, 37:2016.
54. Yoshida T., Mori K., Hatano T., Okumura T., Uehara Lkomagoe K., Fujita Y., et al. Radical-scavenging effects of tannins and related polyphenols on 1,1-diphenyl-2-picrylhydrazyl radical. Chem Pharm Bull 1989, 37:1919.
55. Kim K.H., Lee Y.A., Kim J.S., Lee I., Choi Y.W., Kim H.H., et al. Yakhak Hoechi 2001, 44:354.
56. Gil M.I., Francisco T., Betty H., Deirdre M., Adel K. Antioxidant activity of pomegranate juice and its relationship with phenolic composition and processing. J Agric Food Chem 2000, 48:4581-4589.
57. Lin C.C., Hsu Y.F., Lin T.C., Hsu F.L., Hsu H.Y. Antioxidant and hepatoprotective effects of punicalagin and punicalin on acetaminophen-induced liver damage in rats. Phytother Res 2001, 15:206.
58. Lin C.C., Hsu Y.F., Lin T.C., Hsu F.L., Hsu H.Y. Antioxidant and hepatoprotective activity of punicalagin and punicalin on carbon tetrachloride-induced liver damage in rats. J Pharm Pharmacol 1998, 50:789.
59. Lin C.C., Hsu Y.F., Lin T.C. Antioxidant and free radical scavenging effects of the tannins of Terminalia catappa L. Anticancer Res 2000, 21:237.
60. Amarowicz R., Naczk M., Shahidi F. Antioxidant activity of crude tannins of canola and rapeseed hulls. J Am Oil Chem Soc 2000, 77:957.
61. Ohtani I.I., Gotoh N., Tanaka J., Higa T., Gyamfi M.A., Aniya Y. Thonningianins A and B, new antioxidants from the African medicinal herb Thonningia sanguinea. J Nat Prod 2000, 63:676-679.
62. Ur-Rahman A., Ngounou F.N., Choudhary M.I., Malik S., Makhmoor T., Nur-E-Alam M., et al. New antioxidant and antimicrobial ellagic acid derivatives from Pteleopsis hylodendron. Planta Med 2001, 67:335-339.
63. Iwata S.Y., Fukaya Y., Nakazawa K., Okuda T. Effects of tannins on the oxidative damage of mouse ocular lens I. Using the oxidative damage model induced by the xanthine-xanthine oxidase system. J Ocular Pharmacol Therap 1987, 3:227-238.
64. Nelofer S.K., Aamir A., Hadi S.M. Anti-oxidant, pro-oxidant properties of tannic acid and its binding to DNA. Chem Biol Interact 2000, 125:177-189.
65. Amakura Y., Unia Y., Tsiji S., Ito H., Hatano T., Yoshida T., et al. Constituents and their antioxidative effects in eucalyptus leaf extract used as a natural food additive. Food Chern 2002, 77:47-56.
66. Lister C, Sutton KH, Rohr GE. XXth Polyphenols Communications 2000, Freising-Weihenstphan (Germany). In: Martens S, Treutter D, Forkmann G, editors. September 11-15, 2000; p. 291.
67. Batista MT, Amaral MT, Proenca AMA. XXth Polyphenols Communications 2000, Freising-Weihenstphan (Germany). In: Martens S, Treutter D, Forkmann G, editors. September 11-15, 2000; p. 341.
68. Ariga T., Koshiyama I., Fukushitna D. Antioxidative properties of procyanidins B1 and B3 from azuki beans in aqueous system. Agric Biol Chem 1988, 52:2717.
69. Ariga T., Haman M. Radical scavenging action and its mode in procyanidins B-1 and B-3 from azuki beans to peroxyl radicals. Agric Biol Chem 1990, 54:2499.
70. Uchida S., Edamatsu R., Hiramatsu M., Mori A., Nonaka G., Nishioka I., et al. Condensed tannins scavenge active oxygen radicals. Med Sci Res 1987, 15:831.
71. Saliva R.J., Dannon N., Fernandez Y., Mitjavila S. Oxygen free radical scavenger capacity in aqueous models of different procyanidins from grape seeds. J Agric Food Chem 1991, 39:1549-1552.
72. Ho K.Y., Hung J.S., Tsai C.C., Lin T.C., Hsu Y.E., Lin C.C. Antioxidant activity of tannin components from Vaccinium vitis-idaea L. J Pharm Pharmacol 1999, 51:1075.
73. Qiong G., Baolu Z., Sheengrang S., Jingwu H., Jungai H., Wenjuan X. ESR study on the structure-antioxidant activity relationship of tea catechin and their epimers. Biochem Biophys Acta 1999, 1427:13.
74. Nanjo F., Mori M., Goto K., Biosci Y. Radical scavenging activity of tea catechin and their related compounds. Biotechnol Biochem 2000, 63:1621.
75. Young J.H., Takako Y., Yu S., Seek K., Kyung N., Sook B.B. Peroxynitrite-scavenging activity of green tea tannin. Agric Food Chem 1998, 46:4484.
76. Yokozawa T., Cho E.J., Nakagawa T., Terasawa K., Takeuchi S. Inhibitory effect of green tea tannin on free radical-induced injury to the renal epithelial cell line, LLC-PK1. Pharm Pharmacol Commun 2000, 6:521-526.
77. Borsato M.L.C., Grael C.F.F., Souza G.E.P., Lopes N.P. A-type proanthocyanidin antioxidant from Dioclea lasiophylla. Phytochemistry 2000, 55:805.
78. Goncalves GM, Proenca CA, Patista MT. XXth Polyphenols Communications 2000, Freising-Weihenstphan (Germany). In: Martens S, Treutter D, Forkmann, editors. September 11-15, 2000; p. 349.
79. Haraguchi H, Sagara N, Tanaka T, Fujioka T, Yagi A. XXth Polyphenols Communications 2000, Freising-Weihenstphan (Germany), In: Martens S, Treutter D, Forkmann G, editors. September 11-15, 2000; p. 357.
80. Hernadez T, Duenas M, Estrella I, Rabanal R. XX″' Polyphenols Communications 2000, Freising-Weihenstphan (Germany), In: Martens S, Treutter D, Forkmann G, editors. September 11-15, 2000; p. 535.
81. Morton S.F. Widespread tannin intake via stimulants and masticatories, especially guarana, kola nut, betel vine and accessories. Plantpolyphenols: synthesis, properties, significance 1992, 739. Plenum Press, New York, NY. R.W. Hemingway, P.T. Laks (Eds.).
82. Hirose M., Fukushima S., Shirai T., Hasegawa R., Kato T., Tanaka H., et al. Cell proliferation and forestomach carcinogenesis. J Cancer Res 1990, 81:207.
83. Sayer J.M., Yagi H., Wood A.W., Conney A.H., Jerina D.M. Extremely facile reaction between the ultimate carcinogen benzo[a]pyrene-7,8-diol 9,10-epoxide and ellagic acid. J Am Chem Soc 1982, 104:5562.
84. Okuda T., More K., Ishino M., Hayatsu H. Inhibitory effect of tannins on direct-acting mutagens. Chem Pharm Bull 1984, 32:3755-3758.
85. Okuda T., More K., Ishino M. Constituents of Geranium thunbergii Sieg. et Zucc. VIII. Transformations of geraniin upon decoction. Yakugaku Zasshi 1979, 99:505.
86. Huang M.-T., Chang R.L., Wood A.W., Newmark H.L., Sayer J.I.M., Yagi H., et al. Inhibition of the mutagenicity of bay-region diol-epoxides of polycyclic aromatic hydrocarbons by tannic acid hydroxylated anthraquinones and hydroxylated cinnamic acid derivatives. Carcinogenesis 1985, 6:237.
87. Chen S.-C., Chung K.-T. Mutagenicity and antimutagenicity studies of tannic acid and its related compounds. Food Chem Toxicol 2000, 38:1-5.
88. Kaur S., Grover I.S., Singh M., Kaur S. Antimutagenicity of hydrolyzable tannins from Terminalia chebula in Salmonella typhimurium. Mutat Res 1998, 419:169-179.
89. Kaur S.J., Grover I.S., Kumar S. Modulatory effects of a tannin fraction isolated from Terminalia arjuna on the genotoxicity of mutagens in Salmonella typhimurium. Food Chem Toxicol 2000, 38:1113.
90. Kuroda Y., Hara A.Y. Anticarcinogenic activity of tea polyphenols. Mutat Res 1999, 436:69.
91. Yoshizawa S., Horiuchi T., Fujki H., Yoshida T., Okuda T., Sugimura T. Antitumor promoting activity of (-)-epigallocatechin gallate, the main constituent of tannin in green tea. Phytother Res 1987, 1:44.
92. Pan N., Lin J., Lin S., Lin J. Induction of apoptosis by penta-O-galloyl-beta-d-glucose through activation of caspase-3 in human leukemia HL-60 cells. Europ J Pharmacol 1999, 381:171.
93. Yoshizawa S, Horiuchi T, Suganuma M, Nishiwaki S, Yatsunami J, Okaba S, et al. In: Hunang M-T, Ho C-T, Lee CY, editors. ACS Symposium Series 507, p. 316, Washington, DC: Am. Chem. Soc., 1992.
94. Fujiki H., Suganuma M., Yoshizawa S., Yatsunami J., Nishiwaki S., Furuya S., et al. Cancer chemoperventation 1992, 393. CRC Press, Boca Raton, FL. L. Wattenberg (Ed.).
95. Fujita Y., Yamane T., Tanaka M., Kuwata K., Okuzumi J., Takahashi T., et al. Inhibitory effect of (-)-epigallocatechin gallate on carcinogenesis with N-ethyl-N'-nitro-N-nitrosoguanidine in mouse duodenum. J Cancer Res 1989, 80:503.
96. Yoshiyuki N., Michiaki M., Takeshi H., Isao T., Naomi S., Tsutomu W., et al. Basic life science 1999, Kluwer Academic/Plenum Publisher, New York, 66 (Plant polyphenols 2), p. 629.
97. Tadataka N., Takeshi O., Yuko N., Tsutomu W., Kazuko N., Isao T., et al. Basic life science 1999, Kluwer Academic/Plenum Publisher, New York, 66 (Plant polyphenols 2), p. 665.
98. Komori A., Yatsunami J., Okabe S., et al. Anticarcinogenic activity of green tea polyphenols. Jpn J Clin Oncol 1993, 23:186-190.
99. Wang Z.-Y., Huang M.-T., Ferraro T., Wong C.-Q., Lou Y.R., Reuhl K., et al. Inhibitory effect of green tea in the drinking water on tumorigenesis by ultraviolet light and 12-O-tetradecanoylphorbol-13-acetate in the skin of SKH-1 mice. Cancer Res 1992, 52:1162.
100. Gali-Muhtasib H.U., Yamout S.Z., Sidani M.M. Plant tannins as inhibitors of hydroperoxide production and tumor promotion induced by ultraviolet B radiation in mouse skin in vivo. Oncol Rep 1999, 6:847.
101. Gali-Muhtasib H.U., Yamout S.Z., Sidani M.M. Tannins protect against skin tumor promotion induced by ultraviolet-B radiation in hairless mice. Nutr Cancer 2000, 37:73.
102. Miyamoto K., Kishi N., Koshiura R., Yoshida T., Hatano T., Okuda T. Relationship between the structures and the antitumor activities of tannins. Chem Pharm Bull 1987, 35:814.
103. Miyamoto K., Sasakura M., Matsui E., Koshiura R., Murayama T., Hatano T., et al. Antitumor activity of oenothein B, a unique macrocyclic ellagitannin. J Cancer Res 1993, 48:99-103.
104. Yoshida T., Chou T., Matsuda M., Yasuhara T., Yazaki K., Hatano T., et al. Trimeric hydrolyzable tannins of macro-ring structure with anti-tumor activity. Chem Pharm Bull 1991, 39:1157.
105. Yoshida T., Chou T., Nitta A., Miyamoto K., Koshiura R., Okuda T. Woodfordin C, a macroring hydrolyzable tannin dimer with antitumor activity, and accompanying dimers from Woodfordia fruticosa flowers. Chem Pharm Bull 1990, 38:1211.
106. Miyamoto K., Murayama T., Nomura M., Hatano T., Yoshida T., Furuya T., et al. Antitumor activity and interleukin-1 induction by tannins. Anticancer Res 1993, 31:37.
107. Yang N.-L., Lee C.-Y., Yen K.-Y. Induction of apoptosis by hydrolyzable tannins from Eugenia jambos L. on human leukemia cells. Cancer Lett 2000, 157:65.
108. 1, the macrocyclic hydrolyzable tannin induced apoptosis in HL-60 cell line. Cancer Lett 2000, 149:77.
109. Magiatis P.P., Pratsinis H.H., Kalpoutzakis E.E., Konstantinidou A.A., Davaris P.P., Skaltsounis A.L. Hydrolyzable tannins, the active constituents of three Greek Cytinus taxa against several tumor cell lines. Biol Pharm Bull 2001, 24:707.
110. Shakagami H., Jiang Y., Kusama K., Atsumi T., Ueha T., Taguchi M., et al. Cytotoxic activity of hydrolyzable tannins against human oral tumor cell lines-a possible mechanism. Phytomedicine 2000, 7:39.
111. Hamada S.-I., Kataoka T., Woo J.-T., Yamada A., Yoshida T., Nishimura T., et al. Immunosuppressive effects of gallic acid and chebulagic acid on CTL-mediated cytotoxicity. Biol Pharm Bull 1997, 20:1017.
112. Nonaka G., Nishioka I., Nishizawa M., Yamagishi T., Kashiwada Y., Deutschman G., et al. Anti-AIDS agents. 2. Inhibitory effects of tannins on HIV reverse transcriptase and HIV replication in H9 lymphocyte cells. J Nat Prod 1990, 53:587.
113. Takechi M., Tanaka Y., Takehara M., Nonaka G., Nishioka I. Structure and antiherpetic activity among the tannins. Phytochemistry 1985, 24:2245.
114. Vlietinck A., De Bruyne T., Apers S., Pieters L. Plant derived leading compounds for chemotherapy of human immunodeficiency virus (HIV) infection. Planta Med 1998, 64:97.
115. Yoshida T., Ito H., Hatano T., Kurata M., Nakanishi T., Inada A., et al. New hydrolyzable tannins, shephagenins A and B, from Shepherdia argentea as HIV-1 reverse transcriptase inhibitors. Chem Pharm Bull 1996, 44:1436-1439.
116. El-Mekawy S., Meselhy M., Kusumoto I.T., Kadota S., Hattori M., Namba T. Inhibitory effects of Egyptian folk medicines on human immunodeficiency virus (HIV) reverse transcriptase. Chem Pharm Bull 1995, 43:641.
117. Yamaguchi K., Honda M., Ikigai H., Hara Y., Shimamura T. Inhibitory effects of (-)-epigallocatechin gallate on the life cycle of human immunodeficiency virus type 1 (HIV-1). Antiviral Res 2002, 53:19.
118. Ma C., Nakamura N., Hatori M., Kakuda H., Qio J., Yu H. Inhibitory effects on HIV-1 protease of constituents from the wood of Xanthoceras sorbifolia. J Nat Prod 2000, 63:238.
119. Xu H.X., Wan M., Dong H., But P.P., Foo L.Y. Inhibitory activity of flavonoids and tannins against HIV-1 protease. Biol Pharm Bull 2000, 23:1072.
120. Ahn M.J., Kim C.Y., Lee J.S., Kim T.J., Kim S.H., Lee C.K., et al. Inhibition of HIV-1 integrase by galloyl glucoses from Terminalia chebula and flavonol glycoside gallates from Euphorbia pekinensis. Planta Med 2002, 68:457-459.
121. Karin C.S., Chen L., Mei-Tsu L., Lee S.-S., Chiou J.-F., Ren S., et al. Antiviral tannins from two Phyllanthus species. Planta Med 1999, 65:43.
122. Lee M.-H., Chiu J.F., Yen K.Y., Yang L.-L. EBV DNA polymerase inhibition of tannins from Eugenia uniflora. Cancer Lett 2000, 154:131.
123. Fukuchi K., Sakagami H., Okuda T., Hatano T., Tanuma S., Kitajirna K., et al. Inhibition of Herpes simplex virus infection by tannins and related compounds. Antiviral Res 1989, 11:285.
124. Xu H.-X., Kadota S., Wang H., Kurokawa M., Shiraki K., Matsumoto T., et al. A new hydrolyzable tannin from Geum japonicum and its antiviral activity. Heterocycles 1994, 38:167-175.
125. Ferreira D., Slade D. Oligomeric proanthocyanidins: naturally occurring O-heterocycles. Nat Prod Rep 2002, 19:517-541.
126. Asanaka M., Kurimura T., Koshiura R., Okuda T., Mori M., Yokoi H. Inhibitory effect of ellagitannins on the in vitro replication of human immuno-deficiency virus (HIV). AIDS Res Newslett 1987, 1:72.
127. Nakashima H., Murakami T., Yamamoto M., Sakagami H., Tanuma S., Hatano T., et al. Inhibition of human immunodeficiency viral replication by tannins and related compounds. Antiviral Res 1992, 18:91-103.
128. Ubillas R., Jolad S., Breuning R., Kernan M., King S., Sesin D., et al. SP-303, an antiviral oligomeric proanthocyanidin from the latex of Croton lechleri (Sangre de Drago). Phytomedicine 1994, 1:77.
129. Scalbert A. Antimicrobial properties of tannins. Phytochemistry 1991, 30:3875.
130. Nakahara K., Kawabata S., Ono H., Ogura K., Tanaka T., Ooshima T., et al. Inhibitory effect of oolong tea polyphenols on glycosyltransferases of mutans Streptococci. Appl Environ Microbiol 1993, 59:968.
131. Foo L.Y., Lu Y., Howell A.B., Vorsa N. The structure of cranberry proanthocyanidins which inhibit adherence of uropathogenic P-fimbriated Escherichia coli in vitro. Phytochemistry 2000, 54:173.
132. Foo L.Y., Lu Y., Howell A.B., Vorsa N. A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli. J Nat Prod 2000, 63:1225.
133. Molan A.L., Attwood G.T., Men B.R., McNabb W.C. The effect of condensed tannins from Lotus pedunculatus and Lotus corniculatus on the growth of proteolytic rumen bacteria in vitro and their possible mode of action. Can J Microbiol 2001, 47:626.
134. Mbatha K.R., Downs C.T., Nsahlai I.V. The effects of graded levels of dietry tannin on the epithelial tissue of the gastrointestinal tract, liver and kidney masses of Boer goats. Anim Sci (British) 2002, 74:579-586.
135. Barroso H., Machado J., Pires I., Cabrita J., Gomes E. Antimicrobial activity of Terminalia macroptera root. J Ethnopharmacol 1997, 57:203-207.
136. Kolodziej H., Kayser O., Latte K.P., Ferreira D. Evaluation of the antimicrobial potency of tannins and related compounds using the microdilution broth method. Planta Med 1999, 65:444.
137. Conrad J., Vogler B., Reab S., Klaibir I., Papajewski S., Roos G., et al. Isoterchebulin and 4,6-O-isoterchebuloyl-d-glucose, novel hydrolyzable tannins from Terminalia macroptera. J Nat Prod 2001, 64:294.
138. Latte K.P., Kolodziej H. Antifungal effects of hydrolysable tannins and related compounds on dermatophytes, mould fungi and yeasts. Z Naturforsch 2000, 55c:467.
139. Calzada F., Rojas C., Rivera R., Bye R., Mata K. Geranins A and B, new antiprotozoal A-type proanthocyanidins from Geranium niveum. J Nat Prod 1999, 62:705.
140. Kolodziej H., Kayser O., Kiderlen A.F., Ito H., Hatano T., Yoshida T., et al. Antileishmanial activity of hydrolyzable tannins and their modulatory effects on nitric oxide and tumour necrosis factor-alpha release in macrophages in vitro. Planta Med 2001, 67:825.
141. Kolodziej H., Kayser O., Kiderlen A.F., Ito H., Hatano T., Yoshida T., et al. Proanthocyanidins and related compounds: antileishmanial activity and modulatory effects on nitric oxide and tumor necrosis factor-a-releasein the murine macrophage-like cell line RAW 264.7. Biol Pharm Bull 2001, 24:1016.
142. Kiderlen A.F., Kayser A., Ferrira D., Kolodziej H. Tannins and related compounds: killing of amastigotes of Leishmania donovani and release of nitric oxide and tumour necrosis factor a in macrophages in vitro. Z Naturforsch 2000, 156c:444.
143. Mohamed A.S.A., Mori T., Islam S.Q., Masashi S., Toni Y. Lethal activity of gallo- and condensed tannins against the free-living soil-inhabiting nematode, Caenorhabditis elegans. J Pestic Sci 2000, 25:410-416.
144. Kahn LP, Diaz-Hernandez A. Tannins with anthelmintic properties. In Brooker JD, editor. Tannins in livestock and human nutrition; ACIAR Proceedings No. 92, Canberra, Australia, 2000; p. 140-9.
145. Kimura Y., Okuda H., Okuda T., Yoshida T., Hatano T., Arichi S. Studies on the activities of tannins and related compounds of medicinal plants and drugs. II. Effects of various tannins and related compounds on adrenaline-induced lipolysis in fat cells. Chem Pharm Bull 1983, 31:2497.
146. Kimura Y., Okuda H., Okuda T., Yoshida T., Hatano T., Arichi S. Studies on the activities of tannins and related compounds of medicinal plants and drugs. III. Effects of various tannins and related compounds on adrenocorticotropic hormone-induced lipolysis and insulin-induced lipogenesis from glucose in fat cells. Chem Pharm Bull 1983, 31:2501.
147. Kimura Y., Okuda H., Okuda T., Hatano T., Agata I., Arichi S. Studies on the activities of tannins and related compounds. V. Inhibitory effects on lipid peroxidation in mitochondria and microsomes of liver. Planta Med 1984, 50:473-477.
148. Hatano T., Yamashita A., Hashimoto T., Ito H., Kupo N., Yoshiyama M., et al. Flavan dimers with lipase inhibitory activity from Cassia nomame. Phytochemistry 1997, 46:893.
149. Miou T., Jum K., Takanori K. α-Glucosidase inhibitor from clove (Syzygium aromaticum). Biosci Biotechnol Biochem 2000, 64:294. CA: 132, 275864z (2000).
150. Kiyoshi K., Takashi T. Inhibitory effects of tannins on the NADH dehydrogenase activity of bovine heart mitochondrial complex I. Biol Pharm Bull 1999, 22:240. CA: 131, 2076b (1999).
151. Zenh J., Ramiraz V. Inhibition of mitochondrial proton F0F1-ATPase/ATP synthase by polyphenolic phytochemicals. Br J Pharmacol 2000, 130:1115.
152. Abe I., Kashiwagi Y., Noguchi H., Tanaka T., Ikeskiro Y., Kashiwada Y. Ellagitannins and hexahydroxydiphenoyl esters as inhibitors of vertebrate squalene epoxidase. J Nat Prod 2001, 64:1010.
153. Maffei F.R., Carini M., Aldini J., Beni F., Rossoni G., Bonpardelli E., et al. Procyanidines from Vitis vinifera seeds protect rabbit heart from ischemia/reperfusion injury: antioxidant intervention and/or iron and copper sequestering ability. Planta Med 1996, 62:495-502.
154. Kang W.S., Lim I.-H., Yuk D.-Y., Chung K.-H., Bark J.-B., Yoo H.-S., et al. Antithrombotic activities of green tea catechins and (-)-epigallocatechin gallate. Thromb Res 2001, 96:229.
155. Lin C.C., Hsu Y.F., Lin T.C., Hsu F.L., Hsu H.Y. Protective effect of green tea polyphenol (-)-epigallocatechin gallate and other antioxidants on lipid peroxidation in gerbil brain homogenates. Phytother Res 2001, 15:206.
156. Galvaz J., Crespo M., Zarzuela A., Witte P., Spiessens C. Pharmacological activity of a procyanidin isolated from Sclerocarya birrea bark: antidiarrhoeal activity and effects on isolated guinea-pig ileum. Phytother Res 1993, 7:25.
157. Borrelli F., Izzo A. The plant kingdom as a source of anti-ulcer remedies. The plant kingdom as a source of anti-ulcer remedies. Phytother Res 2000, 14:581-591.
158. Murakami S., Muramatsu M., Otomo S. Gastric H+, K(+)-ATPase inhibition by catechins. J Pharm Pharmacol 1992, 44:926.
159. Suzuki M., Yoshino K., Maeda-Yamamoto M., Miyase T., Sano M. Inhibitory effects of tea catechins and O-methylated derivatives of (-)-epigallocatechin-3-O-gallate on mouse Type-IV allergy. J Agric Food Chem 2000, 48:5649-5653.
160. Sano M., Suzuki M., Miyase T., Yoshino K., Maeda-Yamamoto M. Novel antiallergic catechin derivatives isolated from oolong tea. J Agric Food Chem 1999, 47:1906.
161. Tits M., Angento L., Damas J., Dierckxsens Y., Poukens P. Antiinflammatory prodelphinidins from black currant (Ribes nigrum) leaves. Planta Med 1991, 57(Suppl. 2):A 134.
162. Ascacio-Valdés J.A., Buenrostro-Figueroa J.J., Aguilera-Carbo A., Prado-Barragán A., Rodríguez-Herrera R., Aguilar C.N. Ellagitannins: biosynthesis, biodegradation and biological properties. J Med Plants Res 2001, 5:4696-4703.
163. Niemetz R., Gross G.G. Enzymology of gallotannin and ellagitannin biosynthesis. Phytochemistry 2005, 66:2001-2011.
164. Salminen J.P., Roslin T., Karonen M., Sinkkonen J., Pihlaja K., Pulkkinen P. Seasonal variation in the content of hydrolysable tannins, flavonoid glycosides, and proanthocyanidins in oak leaves. J Chem Ecol 2004, 30:1693-1711.
165. Barbehenn R.V., Jones C.P., Hagerman A.E., Karonen M., Salminen J.P. Ellagitannins have larger oxidative activities than condensed tannins and galloyl glucoses at high pH: potential impact on caterpillars. J Chem Ecol 2004, 32:2253-2267.
166. Niemetz R., Gross G.G. Ellagitannins biosynthesis, laccasecatalyzed dimerization of tellimagrandin II to cornusilin E in Tellima grandiflora. Phytochemistry 2003, 64:1197-1201.
167. Gross G.G. Biosynthesis of hydrolyzable tannins. Carbohydrates and their derivatives including tannins, cellulose, and related lignins 1999, vol. 3:799-826. Elsevier, Amsterdam.
168. Loescher R., Heide L. Biosynthesis of p-hydroxybenzoate from p-coumarate and p-coumaroyl-Coenzyme A in cell-free extracts of Lithospermum erythrorhizon cell cultures. Plant Physiol 1994, 106:271-279.
169. 13C-labeled glucose: formation of gallic acid in plants and fungi. J Biol Chem 1997, 272:25474-25482.
170. Gross GG. In: Lewis NG, Paice MG, editors. Plant cell wall polymers: biogenesis and biodegradation. ACS Symposium Series, Washington, DC, 1989; 399: p. 108.
171. Gross GG. In Stafford HA, Ibrahim RK, editors. Phenolic metabolism in plants. Rec. Adv. Phytochem. Plenum Press, New York, NY, 1992; 26: p. 297.
172. Gross G.G. Synthesis of galloyl-coenzyme A thioester. Z Naturforsch 1982, 37c:778.
173. Gross G.G. Synthesis of β-glucogallin from UDP-glucose and gallic acid by an enzyme preparation from oak leaves. FEBS Lett 1982, 148:67.
174. Gross G.G. Partial purification and properties of UDP-glucose: vanillate 1-O-glucosyl transferase from oak leaves. Phytochemistry 1983, 22:2179-2182.
175. Gross G.G. Synthesis of mono-, di- and trigalloylβ-d-glucose by β-glucogallin-dependent galloyltransferases from oak leaves. Z Naturforsch 1983, 38c:519-523.
176. Hagenah S., Gross G.G. Biosynthesis of 1,2,3,6-tetra-O-galloylβ-d-glucose. Phytochemistry 1993, 32:637-641.
177. Reinefeld E., Ahrens D. Der Einfluss der Konfiguration auf die partielle Verestererung von d-Glucopyranosiden. Liebigs Ann Chem 1971, 747:39-44.
178. Hofmann A.S., Gross G.G. Biosynthesis of gallotannins: formation of polygalloyl-glucoses by enzymatic acylation of 1,2,3,4,6-penta-O-galloylglucose. Arch Biochem Biophys 1990, 283:530-532.
179. Niemetz R., Gross G.G. Gallotannin biosynthesis: β-glucogallin: hexagalloyl 3-O galloyltransferase from Rhus typhina leaves. Phytochemistry 2001, 58:657-661.
180. Froehlich B., Niemetz R., Gross G.G. Gallotannin biosynthesis: two new galloyltransferases from Rhus typhina leaves preferentially acylating hexa- and heptagalloylglucoses. Planta 2002, 216:168-172.
181. Niemetz R., Gross G.G. Gallotannin biosynthesis: a new β-glucogallin-dependent galloyltransferase from sumac leaves acylating gallotannins at positions 2 and 4. J Plant Physiol 1999, 155:441-444.
182. Niemetz R., Gross G.G. Gallotannin biosynthesis. Purification of β-glucogallin: 1,2,3,4,6-pentagalloylβ-d-glucose galloyltransferase from sumac leaves. Phytochemistry 1998, 49:27-332.
183. 14C]-labelled 1,2,3,4,6-penta-O-galloylβ-d-glucose and related gallotannins. Z Naturforsch 1996, 51c:473-476.
184. Okuda T., Yoshida T., Hatano T. New methods for analyzing tannins. J Nat Prod 1989, 52:31.
185. Feldman S., Sahasrabudhe K. Ellagitannin chemistry. Syntheses of tellimagrandin II and a dehydrodigalloyl ether-containing dimeric gallotannin analogue of coriarin A. J Org Chem 1999, 64:209-216.
186. Niemetz R., Schilling G., Gross G.G. Biosynthesis of the dimeric ellagitannin, cornusiin E, in Tellima grandiflora. Phytochemistry 2003, 64:109-114.
187. Marzouk M.S.A., El-Toumy S.A., Moharram F.A., Shalaby N.M., Ahmed A.A. Pharmacologically active ellagitannins from Terminalia myriocarpa. Planta Med 2002, 68:523-527.
188. 4-induced liver damage in rats. Bull Fac Pharm Cairo Univ 2002, 40:175-187.
189. Moharram F.A., Marzouk M.S.A., El-Toumy S.A.A., Ahmed A.A.E., Aboutabl E.A. Polyphenols of Melaleuca quinquenervia leaves-pharmacological studies of grandinin. Phytother Res 2003, 17:767-773.
190. Marzouk M.S.A., Gamal-Eldeen A.M., Mohamed M.A., El-Sayed M.M. Anti-proliferative and antioxidant constituents from Tecoma stans. Z Naturforsch 2006, 61c:783-791.
191. Marzouk M.S.A., Moharram F.A., Mohamed M.A., Gamal-Eldeen A.M., Aboutabl E.A. Anti-cancer and antioxidant tannins from Pimenta dioica leaves. Z Naturforsch 2007, 62c:526-536.
192. Marzouk M.S.A., Moharram F.A., Gamal-Eldeen A.M., DamLakhy I.M. Spectroscopic identification of new ellagitannins and a trigalloylglucosylkaempferol from an extract of Euphorbia cotinifolia L. with antitumour and anetioxidant activity. Z Naturforsch 2012, 67c:151-162.
193. Hussein S.A.M., Hashim A.N.M., El-Sharawy R.T., Seliem M.A., Linscheid M., Lindequist U., et al. Ericifolin: an eugenol 5-O-galloylglucoside and other phenolics from Melaleuca ericifolia. Phytochemistry 2007, 68:1464-1470.
194. Bessong P.O., Obi C.L., Andréola M.-L., Rojas L.B., Pouységu L., Igumbor E., et al. Evaluation of selected South African medicinal plants for inhibitory properties against human immunodeficiency virus type 1 reverse transcriptase and integrase. J Ethnopharmacol 2005, 99:83-91.
195. Nawwar M.A., Ayoub N.A., El-Rai M.A., Bassyouny F., Mostafa E.S., Al-Abd A.M., et al. Cytotoxic ellagitannins from Reaumuria vermiculata. Fitoterapia 2012, 83:1256-1266.
196. Shahat A.A., Cos P., De Bruyne T., Apers S., Hammouda F.M., Ismail S., et al. Antiviral and antioxidant activity of flavonoids and proanthocyanidins from Crataegus sinaica Boiss. Planta Med 2002, 68:539-541.
197. Idowu T.O., Ogundaini A.O., Salau A., Obuotor E.M., Bezabih M., Abega B.M. Doubly linked, A-type proanthocyanidin trimer and other constituents of Ixora coccinea leaves and their antioxidant and antibacterial properties. Phytochemistry 2010, 71:2092-2098.
198. Shahat A., Hammouda F.M., Ismail S.I., Azzam S.A., De Bruyne T., Lasure A., et al. Anti-complementary activity of Crataegus sinaica. Planta Med 1996, 62(1):10-13.
199. Lu Y., Yeap Foo L. Antioxidant and radical scavenging activities of polyphenols from apple pomace. Food Chem 2000, 68:81-85.
200. Shahat A.A., Ahmed H.H, Hassan R.A., Hussein A.A. Antioxidant activity of proanthocyanidins from Adansonia digitata fruit. Asian Pac J Trop Med 2008, 1:55-59.
201. Funatogawa K., Hayashi S., Shimomura H., Yoshida T., Hatano T., Ito H., et al. Antibacterial activity of hydrolyzable tannins derived from medicinal plants against Helicobacter pylori. Microbiol Immunol 2004, 48:251-261.
202. Hatano T., Miyatake H., Natsume M., Takizawa T., Ito H., Yoshida T. Proanthocyanidin glycosides and related polyphenols from cacao liquor and their antioxidant effect. Phytochemistry 2002, 59:749-758.
203. Shahat A.A., Ismail S.I., Hammouda F.M., Azzam S.A., Lemiere G., De Swaef S., et al. Anti-HIV activity of flavonoids and proanthocyanidins from Crataegus sinaica. Phytomedicine 1998, 5:133-136.
204. Souleman A.M.A., Barakat H.H., El-Mousallamy A.M.D., Marzouk M.S.A., Nawwar M.A.M. Phenolics from the bark of Tamarix aphylla. Phytochemistry 1991, 30:3763-3766.
205. Nawwar M.A.M., Marzouk M.S.A., Nigge W., Linscheid M. High performance liquid chromatography/electrospray ionization mass spectrometric screening for polyphenolic compounds of Epilobium hirsutum-the structure of the unique ellagitannin epilobamide-A. J Mass Spectrom 1997, 32:645-654.
206. Barakat H.H., Hussein S.A.M., Marzouk M.S.A., Merfort I., Linscheid M., Nawwar M.A.M. Polyphenolic metabolites of Epilobium hirsutum. Phytochemistry 1997, 46:935-941.
207. Nawwar M.A.M., Buddrus J., Bauer H. Dimeric phenolic constituents from the roots of Tamarix nilotica. Phytochemistry 1982, 21:1755-1758.
208. Hussein S.A.M., Barakat H.H., Merfort I., Nawwar M.A.M. Tannins from the leaves of Punica granatum. Phytochemistry 1997, 45:819-823.
209. Hussein S.A.M., Ayoub N.A., Nawwar M.A.M. Caffeoyl sugar esters and an ellagitannin from Rubus sanctus. Phytochemistry 2003, 63:905-911.
210. El-Toumy S.A.A., Marzouk M.S.A., Rauwald H.W. Ellagi- and gallotannins from Punica granatum hartwood. Pharmazie 2001, 56:823-824.
211. Moharram F.A. Hydrolysable tannins and related phenolic acids from Punica granatum var. nana Pers. pericarp. Az J Nat Prod 2006, 10:1-11.
212. Moharram F.A., Marzouk M.S.A. A novel phenylethanoid dimer and flavonoids from Jacaranda memosaefolia leaves. Z Naturforsch 2007, 62b:1213-1220.
213. Marzouk M.S.A. Acylated flavonol glycosides and hydrolysable tannins from Euphorbia cotinifolia L. leaves. Bull Fac Pharm Cairo Univ 2008, 46:191-201.
214. Orabi M.A.A., Taniguchi S., Hatano T. Monomeric and dimeric hydrolysable tannins of Tamarix nilotica. Phytochemistry 2009, 70:1286-1293.
215. Balde A.M., Pieters L.A., Gergely A., Kolodziej J.H., Claeys M., Vlietinck A.J. A-Type proanthocyanidins from stem-bark of Pavetta owariensis. Phytochemistry 1991, 30:337-342.
216. Balde A.M., De Bruyne T., Pieters L., Kolodziej H., Vanden Berghe D., Claeys M., et al. Tetrameric proanthocyanidins containing a double interflavonoids (A-type) linkage from Pavetta owariensis. Phytochemistry 1995, 40:933-938.
217. Balde A.M., De Bruyne T., Pieters L., Kolodziej H., Vanden Berghe D., Claeys M., et al. Oligomeric proanthocyanidins possing a doubly linked structure from Pavetta owariensis. Phytochemistry 1995, 38:719-723.
218. Bennie L., Coetzee J., Malan E., Woolfrey J.R., Ferreira D. Oligomeric flavanoids. Part 34: Doubly-linked proteracacinidin analogues from Acacia caffra and Acacia galpinii. Tetrahedron 2001, 57:661-667.
219. Bennie L., Coetzee J., Malan E., Slade D., Marais J.P.J., Ferreira D. Trimeric proteracacinidins and a (6→6)-bis-leucotera-cacinidin from Acacia galpinii and Acacia caffra. Phytochemistry 2004, 65:215-220.
220. Lakenbrink C., Engelhardt U.H., Wra V. Identification of two novel proanthocyanidins in green tea. J Agric Food Chem 1999, 47:4621-4624.
221. Mahmoud I., Moharram F.A., Marzouk M.S.A., Soliman H.S.M., El-Dib R.A. Two new flavonol glycosides from leaves of Koelreuteria paniculata. Pharmazie 2001, 56:580-582.
222. Nawwar M.A.M., Hussein S.A.M., Merfort I. NMR spectral analysis of polyphenols of Punica granatum. Phytochemistry 1994, 36:793-798.
223. Mahmoud I.I., Marzouk M.S.A., Moharram F.A., El-Gindi M.R., Hassan A.M.K. New acylated flavonol glycosides from Eugenia jambolana leaves. Phytochemistry 2001, 58:1239-1244.
224. Marzouk M.S.A. An acylated flavonol glycoside and hydrolysable tannins from Callistemon lanceolatus flowers and leaves. Phytochem Anal 2008, 19:541-549.
225. Khallouki F., Haubner R., Hull W.E., Erben G., Spiegelhalder B., Bartsch H., et al. Isolation, purification and identification of ellagic acid derivatives, catechins, and procyanidins from the root bark of Anisophyllea dichostyla R. Br. Food Chem Toxicol 2007, 45:472-485.
226. Foo L.Y., Newman R., Waghorn G., McNabb W.C., Ulyatt M.J. Proanthocyanidins from Lotus corniculatus. Phytochemistry 1996, 41:617-624.
227. Foo L.Y., Lu Y., McNabb W.C., Waghorn G., Ulyatt M.J. Proanthocyanidins from Lotus pedunculatus. Phytochemistry 1997, 45:1689-1696.
228. de Pascual T.S., Gutierrez F.Y., Rivas G.J.C., Santos B.C. Characterization of monomeric and oligomeric flavan-3-ols from unripe almond fruits. Phytochem Anal 1998, 9:21-27.
229. Helsper J.P.F.G., Kolodziej H., Hoogendijk J.M., Van-Norel A. Characterization and trypsin inhibitor activity of proanthocyanidins from Vicia faba. Phytochemistry 1993, 34:1255-1260.
230. Natsume M., Osakabe N., Yamagishi M., Takizawa T., Nakamura T., Miyatake H., et al. Analyses of polyphenols in cacao liquor, cocoa, and chocolate by normal-phase and reversed-phase HPLC. Biosci Biotechnol Biochem 2000, 64:2581-2587.
231. Hör M., Heinrich M., Rimpler H. Proanthocyanidin polymers with antisecretory activity and proanthocyanidin oligomers from Guazuma ulmifolia bark. Phytochemistry 1996, 42:109-119.
232. Kamiya K., Watanabe C., Endang H., Umar M., Satake T. Studies on the constituents of bark of Parameria laevigata Moldenke. Chem Pharm Bull 2001, 49:551-557.
233. Kandil F.E., Song L., Pezzuto J.M., Marley K., Seigler D.S., Smith M.A.L. Isolation of oligomeric proanthocyanidins from flavonoid-producing cell cultures. In Vitro Cell Dev Biol Plant 2000, 36(6):492-500.
234. Falleh H., Oueslati S., Guyot S., Dali A.B., Magné C., Abdelly C., et al. LC/ESI-MS/MS characterisation of procyanidins and propelargonidins responsible for the strong antioxidant activity of the edible halophyte Mesembryanthemum edule L. Food Chem 2011, 127:1732-1738.
235. Hartisch C., Kolodziej H. Galloylhamameloses and proanthocyanidins from Hamamelis virginiana. Phytochemistry 1996, 42:191-198.
236. Stevens J.F., Miranda C.L., Wolthers K.R., Schimerlik M., Deinzer M.L., Buhler D.R. Identification and in vitro biological activities of hop proanthocyanidins: inhibition of nNOS activity and scavenging of reactive nitrogen species. J Agric Food Chem 2002, 50:3435-3443.
237. Kayser O., Abreu P.M. Antileishmania and immunostimulating activities of two dimeric proanthocyanidins from Khaya senegalensis. Pharm Biol 2001, 39:284-288.
238. Sato M., Islam S.Q., Awata S., Yamasaki T. Flavanonol glucoside and proanthocyanidins: oviposition stimulants for the cerambycid beetle, Monochamus alternatus. J Pestic 1996, 24:123-129.
239. Danne A., Petereit F., Nahrstedt A. Proanthocyanidins from Citrus incanus. Phytochemistry 1993, 34:1129-1133.
240. Coetzee J., Malan E., Ferreira D. Oligomeric flavanoids. Part XXVIII: structure and synthesis of ether-linked [4-O-3]-bis-teraca-cinidins, a novel class of naturally occurring proanthocyanidins. J Chem Res 1998, (S) 526-7, (M) 2287-96.
241. de-Mello J.P., Petereit F., Nahrstedt A. Flavan-3-ols and prodelphinidins from Stryphnodendron adstringens. Phytochemistry 1996, 41:807-813.
242. Weinges K., Schick H. Dodecaacetylprodelphinidin B3 from the dried leaves of Ziziphus spina-christi. Phytochemistry 1995, 38:505-507.
243. Bennie L., Coetzee J., Malan E., Ferreira D. (4-6)-Coupled proteracacinidins and promelacacinidins from Acacia galpinii and Acacia caffra. Phytochemistry 2002, 60:521-532.
244. Coetzee J., Malan E., Ferreira D. Oligomeric flavanoids. Part XXIX: structure and synthesis of novel ether-linked [4-O-4] bis-teracacinidins. Tetrahedron 1998, 54:9153-9160.
245. Bennie L., Malan E., Coetzee J., Ferreira D. Structure and synthesis of ether-linked proteracacinidin and promelacacinidin proanthocyanidins from Acacia caffra. Phytochemistry 2000, 53:785-793.
246. Ferreira D., Nel R.J.J., Bekker R. Condensed tannins. Comprehensive natural products chemistry 1999, 791-797. Elsevier, Kidlington, Oxford. D.H.R. Barton Sir, K. Nakanishi, O. Meth-Cohn, B.M. Pinto (Eds.).
247. Lou H.X., Yamazaki Y., Sasaki T., Uchida M., Tanaka H., Oka S. A-type proanthocyanidins from peanut skins. Phytochemistry 1999, 51:297-308.
248. Nakashima S., Oda C., Masuda S., Tagashira M., Kanda T. Isolation and structure elucidation of tetrameric procyanidins from unripe apples (Malus pumilacv. Fuji) by NMR spectroscopy. Phytochemistry 2012, 83:144-152.
249. Prasad D. Two A-type proanthocyanidins from Prunus armeniaca roots. Fitoterapia 2000, 71:245-253.
250. Rawat M.S.M., Prasad D., Joshi R.K., Pant G. Proanthocyanidins from Prunus armeniaca roots. Phytochemistry 1999, 50:321-324.
251. Gonzalez A.G., Irizar A.C., Ravelo A.G., Fernandez M.F. Type A proanthocyanidins from Prunus spinosa. Phytochemistry 1992, 31:1432-1434.
252. Bilia A.R., Morelli I., Hamburger M., Hostettmann K. Flavans and A-type proanthocyanidins from Prunus prostrata. Phytochemistry 1996, 43:887-892.