Distribution, bioactivities and therapeutical potentials of pentagalloylglucopyranose

Current Bioactive Compounds

Volumn 3, Issue 2, 2007, Pages 81-89

  Ren, Yulin ^a   Chen, Xiaozhen ^a  

^a OHIO UNIVERSITY   (United States)

Author keywords

12 O tetradecanoyl phorbol 13 acetate; Aldose reductase; Antioxidants; Antitumor bioassay guided isolation; Euphorbiaceae; MCP 1 genes

Indexed keywords

ADENOSINE TRIPHOSPHATASE (POTASSIUM SODIUM); ALDEHYDE REDUCTASE; ALPHA PENTAGALLOYLGLUCOPYRANOSE; BETA PENTAGALLOYLGLUCOPYRANOSE; CARBON; CYCLOOXYGENASE 2; ENDOTHELIN 1; ESTER; GLUCOSE; GLUCOSE TRANSPORTER 4; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDUCIBLE NITRIC OXIDE SYNTHASE; INSULIN RECEPTOR; INTERLEUKIN 8; MONOCYTE CHEMOTACTIC PROTEIN 1; MONOPHENOL MONOOXYGENASE; POLYPHENOL DERIVATIVE; PROTEIN C JUN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE; TANNIN; TRANSCRIPTION FACTOR AP 1; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANTICOAGULATION; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ANTIVIRAL ACTIVITY; CANCER INHIBITION; CARDIOVASCULAR DISEASE; COVALENT BOND; DIABETES MELLITUS; DRUG ACTIVITY; DRUG POTENCY; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; HERB; HUMAN; ISOMER; LIVER MITOCHONDRION; NEUROPROTECTION; NONHUMAN; PLANT TISSUE; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN LOCALIZATION; PROTEIN SYNTHESIS INHIBITION; REVIEW; STOMACH DISEASE; STRUCTURE ACTIVITY RELATION;

EID: 34250319262     PISSN: 15734072     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340707780809635     Document Type: Review

References (166)

1. Nishizawa, M.; Yamagishi T.; Nonaka G.; Nishioka I.; Bando H. (1982) Novel hydrolyzable tannins from Nuphar Japonicum DC. Chem. Pharm. Bull., 30, 1094-1097.
2. Xu, G.; He, H.; Xu, L.; Jing, R. Chinese Medical Material. (1996) Press of Chinese Medical Technology, Beijing, pp. 1738.
3. Sun, W.; Sheng, J. Brief Handbook of Natural Bioactive compounds. (1998) Press of Chinese Medical Technology, Beijing, pp. 436.
4. Kim, Y.J.; Woo, E.R.; Shin, C. G.; Park, H. (1998) A new flavonol glycoside gallate ester from Acer okamotoanum and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase. J. Nat. Prod., 61, 145-148.
5. Yu, W.; Chen, X.; Yang, L.; Li, Y. Tannin constituents of Ampelopsis japonica. (1995) Tianran Chanwu Yanjiu Yu Kaifa, 7, 15-18.
6. Matsuo, K.; Kobayashi, M.; Takuno, Y.; Kuwajima, H.; Ito, H.; Yoshida, T. (1997) Anti-tyrosinase activity constituents of Arctostaphylos uva-ursi. Yakugaku Zasshi, 117, 1028-1032.
7. Chumbalov, T.K; Pashinina, A.T.; Bikbulatova, T.N.; Llyasova, M.I.; Petunina, A.G.; Frizen, I.D.; Ponomareva, N.M. (1977) Study of the chemical components of the dry extract of Bergenia roots. Vitamin, Rastitel'n, Resursy I Ikh zspolg, 354-356.
8. Ossipov, V.; Salminen, J.P.; Ossipova, S.; Haukioja, E.; Pihlaja, K. (2003) Gallic acid and hydrolysable tannins are formed in birch leaves from an intermediate compound of shikimate pathway. Biochem. System. Ecolog., 31, 3-16.
9. Salminen, J.P.; Ossipov, V.; Haukoja, E.; Pihlaja, K. (2001) Seasonal variation in the content of hydrolyzable tannins in leaves of Betula pubescens. Phytochemistry, 57, 15-22.
10. Mohamed A.S.A.; Mori, T.; Islam, S.Q.; Sato, M.; Yamasaki, T. (2000) Lethal activity of gallo- and condensed tannins against the free living soil-inhabiting nematode Caenorhabditis elegans. Nippon Noyaku Gakkaishi, 25, 410-415.
11. Salminen, J.P.; Ossipov, V.; Loponen, J.; Haukioja, E.; Pihlaja, K. (1999) Characterization of hydrolysable tannins from leaves of Betula pubescens by high performance liquid chromatography mass spectrometry. J. Chromatogr., A, 864, 283-291.
12. Nonaka, G.; Akayawa, M.; Nishioka, I. (1992) Tannins and related compound, Part III, two new ellagitannin metabolites, carpinusin and carpinusnin from Carpinus laxiflora. Heterocycles, 33, 597-606.
13. Nonaka, G.; Ishimatsu, M.; Ageta, M.; Nishioka, I. (1989) Tannins and related compounds. LXXVI, Isolation and characterization of cercidinins A and B and cuspinin, unusual 2,3-(R)-hexahydroxy-diphenoyl glucose from Cercidphyllum japonicum and Castanopsis cuspidata Var Sieboldii. Chem. Pharm. Bull., 37, 50-53.
14. Kandil, F.E.; Grace, M.H. (2001) Polyphenols from Cornulaca monacantha. Phytochemistry, 58, 611-613.
15. Tanaka, N.; Kamiya, T.; Shimomura, K.; Ishimaru, K. (1998) Polyphenols in adventitious roots cultures of Cornus capitata. Nat. Med., 52, 510-517.
16. Tanaka, N.; Shimomura, K.; Kamiya, T.; Kayano, T.; Ishimaru, K. (1997) Tannins and related compounds in callus and root cultures of Cornus capitala. Plant Biotech. (Tokyo), 14, 59-62.
17. Yazaki, K.; Okubo, T. (1989) Gallotannin production in cell culture of Cornus officinalis Sieb, et ZUcc. Plant Cell Rep., 8, 346-349.
18. Jin, Z.; Zhang, X. (2001) Studies on tannin components of Corylus heterophylla leaves. Zhongcaoyao, 32, 193-195
19. Chen, L.G.; Yen, K.Y.; Yang, L.L.; Hatano, T.; Okuda, T.; Yoshida, T. (1998) Monocyclic ellagitannin dimmers cuphiins D1 and D2, and accompanying tannins from Cuphea hyssopifolia. Phytochemistry, 50, 307-312.
20. Yoshida, T.; Maruyama, T.; Nitta, A.; Okuda, T. (1992) Eutalbanins A. B. and C, monomeric and dimeric hydrolysable tannins from Eucalyptus alba Reinw. Chem. Pharm. Bull., 40, 3358.
21. Yoshida, T.; Maruyama, T.; Nitta, A.; Okuda, T. (1992) Eucalbanins A, B and C, monomeric and dimerica hydrolysable tannins from Eucalyptus alba Reinw. Chem. Pharm. Bull., 40, 1750-1754.
22. lee, S.H.; Tanaka, T.; Nonaka, G.; Nishioka, I. (1991) Tannins and related compounds. CV. Monomeric and dimeric Hydrolysable tannins having a dehydrohexa-hydroxydiphenoyl group, sapinanin, euphorscopin, euphorhelin and jolkianin from Euphorbia species. Chem. Pharm. Bull., 39, 630-638.
23. Chen, L. (1991) Polyphenols from leaves of Euphobia hirta L. ZhongGuo ZhongYao Zazhi, 16, 38-39.
24. Yoshida, T.; Chen, L.; Shingu, T.; Okuda, T. (1988) Tannins and related polyphenols of Euphorbiaceous plants. IV. Euphorbins A and B, novel dimeric dehydroellagitannis from Euphorbia hirta L. Chem. Pharm. Bull., 36, 2940-2949.
25. Amakura, Y.; Kawada, K.; Hatano, T.; Agata, I.; Sugaya, T.; Nishibge, S.; Okuda, T.; Yoshida, T. (1997) Four new hydrolysable tannins and an acylated flavonol glycoside from Euphorbia maculata. Can. J. Chem., 75, 727-733.
26. Yoshida, T.; Namba, O.; Kurokawa, K.; Amakura. Y.; Liu, Y.; Okuda, T. (1994) Tannins and related Polyphenols of Euphorbiaceous plants. XLL, Euphorbins G and H, new dimeric hydrolysable tannins from Euphorbia prostrata and Euphorbia makinoi. Chem. Pharm. Bull., 42, 2005-2010.
27. Ahn, B.T.; Zhang, B.K.; Lee, S.C.; Kim, T.G.; Ro, J.S.; Lee, K.S. (1996) Phenolic compounds of aerial parts of Euphorbia pekinensis. Yakhak Hoechi, 40, 170-176.
28. Lee, S.H.; Tanaka, T.; Nonaka, G.; Nishioka, I. (1990) Hydrolysable tannins from Euphorbia thymifolia. Phytochemistry, 29, 3621-3625.
29. Amakura, Y.; Yoshida, T. (1996) Tannins and related polyphenols of Euphorbiaceous plants XIV. Euphorbin I, a new dimeric hydrolysable tannin from Euphorbia. Chem. Pharm. Bull., 44, 1293-1297.
30. Ishimaru, K.; Shimomura, K. (1991) Tannin production in hairy root culture of Geranium thunbergii. Phytochemistry, 30, 825-828.
31. Okuda, T.; Mori, K.; Hayatsu, H. (1984) Inhibitory effect of tannins on direct-acting mutagens. Chem. Pharm. Bull., 32, 3255-2758.
32. Dong, H.; Chen, S.X.; Kim, R.M.; Xu, H.X. (1998). Effects of tannins from Geum japonicum on the catalytic activity of thrombin and factor Xa of blood coagulation castade. J. Nat. Prod., 61, 1356-1360.
33. Kandil, F.E.; EI-Sayed, N.H.; Michael, H.N.; Ishak, M.S.; Mabry, T.J. (1996) Gallotannins and Flavonoids from Hoematoxylin campechianum. Phytochemistry, 42, 1243-1245.
34. Nabil, H.; Sayed, E.L.; Michael, H.N.; Kandil, F.E.; Ishak, M.S.; Mabry, T.J. (1994) Flavonoids and other phenolics of Haematoxylon campechianum. Biochem. System. Ecol., 22, 763-764.
35. Sayed, N.H.E.I.; Ansari, M.A.E.I.; Shalaby, A.N.; Mabry, T.J. (1988) Phenolics and flavonoids of the pericapr of Harpullia pendula. Revista Latinoamericana de Quimica, 19, 66.
36. Hirschmann, G.S.; Zuniga, J.; Dutra-Behrens, M.; Haberment, G. (1996) Xanthine oxidese inhibitory activity of flavonoids and tannins from Hexachlamys edulis (Myrtaceae). Phyrothera. Res., 10, 260-262.
37. Bakkali, A.T.; Jaziri, M.; Ishimaru, K.; Tanaka, N.; Shimomura, K.; Yoshimatsu, K.; Homes, J.; Vanhaelen, M. (1997) Tannin production in hairy root cultures of Lawsonia inermis. J. Plant Physiol., 151, 505-508.
38. Neera, S.; Arakawa, H.; Ishimaru, K. (1993) Tannin production in cell cultures of liquidambar styraciflua. Phytochemistry, 32, 921-934.
39. Yoshida, T.; Tanei, S.; Liu, Y.; Yuan, K.; Ji, C.R.; Okuda, T. (1993) Tannins and related polyphenols of hamamelidaceous plants. Part-6. Hydrolysable tannin from Loropetalum Chinense. Phytochemistry, 32, 1287-1292.
40. Lin, J.H.; Nonaka, G.; Nishioka, I. (1990) Tannins and related compounds, XCIV. Isolation and characterization of seven new hydpalylable tannins from the leaves of Macarange tanarius L. Muell. Et Arg. Chem. Pharm. Bull., 38, 1218-1223.
41. Saijo, R.; Nonaka, G.; Nishioka, I. (1990) Tannins and related compounds, Part 81. Gallic acid esters of bergenin from Mallocus japonicus. Phytochemistry, 29, 267-270.
42. Yoshida, T.; Maruyama, T.; Nitta, A.; Okuda, T. (1996). Anhydrolysable tannin and accompanying polyphenols from Melaleuca leucadendron. Phytochemistry, 42, 1171-1173.
43. Nonaka, G.; Ishimatsu, M.; Tanaka, T.; Nishioka, I.; Nishiyawa, M.; Yamagishi, T. (1987) Tannins and related compound LVIII. Novel gallotannins possessing an α-glucose core from Nuphar japonicum DC. Chem. Pharm. Bull., 35, 3127-3131.
44. Nishizawa, M.; Yamagishi, T.; Nonaka, G.; Nishioka, I.; Bando, H. (1982) Novel hydrolyzable tannins from Nuphar japonicum DC. Chem. Pharm. Bull., 30, 1094-1097.
45. Nishizawa, M.; Yamagishi, T.; Nonaka, G.; Nishioka, I. (1980) Structure of Gallotannins in Paeoniae Radix. Chem. Pharm. Bull., 28, 2850-2852.
46. Hayashi, T.; Katsura, E.; Kaneshima, H.; Yamagishi, T. (1983) Chemical studies on Paeoniae root. Hokkaidoritsu Eisei Kenkyushoho, 33, 35-38.
47. Nishizawa, M.; Yamagishi, T.; Nonaka, G.; Nishioka, I. (1984) Quantitative determination of Gallotannin in Paeoniae Radix. Yakugaku Zasshi, 104, 1244-1250
48. +-ATPase. Clin. Chim. Acta, 290, 159-167.
49. Tanaka, T.; Kataoka, M.; Tsuboi, N.; Kouno, I. (2000) New monoterpene glycoside esters and phenolic constituents of Paeoniae radix, and increase of water solubility of proanthocyanidins in the presence of paeoniflorin. Chem. Pharm. Bull., 48, 201-207.
50. Okubo, T.; Nagai, F.; Seto, T.; Satoh, K.; Ushiyama, K.; Kano, I. (2000) The inhibition of phenylhydroquinone - induced oxidative DNA cleavage by constituents of Moutan cortex and Paeoniae radix. Chem. Pharm. Bull., 23, 199-203
51. Bang, M.H.; Song, J.C.; Lee, S.Y.; Park, N.K.; Baek, N.I. (1999) Isolation and structure determination of antioxidants from the root of Paeoniae lactiflora. Han'Guk Nonghwa Hakhoechi, 42, 170-175.
52. +-ATPase by 1, 2, 3, 4, 6-penta-O-galloyl-β-D-glucose, a major constituent of both Moutan cortex and Paeoniae Radix. Biochem. Pharmacol., 53, 611-614.
53. Nishizawa, M.; Yamagishi, T.; Nonaka, G.; Nishioka, I.; Nagasawa, T.; Dura, H. (1982) Tannins and related compound. XII, Isolation and characterization of galloylglucoses from Paeoniae radix and their effect on urea-nitrogen concentration in rat serum. Chem. Pharm. Bull., 31, 2593-2600.
54. Shibutani, S.; Nagasawa, T.; Oura, H.; Nonaka, G.; Nishioka, I. (1981) Effect of extract from Paeoniae radix on urea-nitrogen concentration in rat serum. Chem. Pharm. Bull., 29, 874-878.
55. Oh, G.S.; Pae, H.O.; Chai, B.N.; Jeong, S.; Oh, H.; Oh, C.S.; Rho, Y.D.; Kim, D.H.; Shin, M.K.; Chung, H.T. (2003) Inhibitory effects of the root cortex of Paeonia suffruticosa, on interleukin-8 and macrophage chemoattractant protein-1 secretions in U937 cells. J. Ethnopharm., 84, 85-89.
56. Oh, G.S.; Pae, H.; Oh, H.; Hong, S.G.; Kim, K.; Chai, K.Y.; Yun, Y.G.; Kwon, T.O.; Chung, H.T. (2001) In vitro anti-proliferative effect of 1,2,3,4,6-penta-o-galloyl-β-glucose on human hepato-cellular carcinoma cell line, SK-HEP-1 cells. Cancer Lett., 174, 17-24.
57. Kim, S.I.; Song, K.S. (2000) 1, 2, 3, 4, 6-Pentagalloyl-β-D-glucopyranose: a prolyl endopeptidase inhibitor from Mouton cortex. Hanguk Nonghwa Hakhoechi, 43, 158-161
58. Kwon, O.G.; Kim, S.H.; Chun, B.Y.; Park, C.K.; Son, KH. (1999) Isolation of antimicrobial components from Moutan cortex. Saengyak Hakhoechi, 30, 340-344.
59. Satoh, K.; Yasuda, I.; Nagai, F.; Seto, T.; Kano, I. (1999) Purification of 1, 2, 3, 4, 6-penta-O-galloyl-β-D-glucose from Moutan cortex (Paeunia Suffruiticosa) and its inhibitory mechanism of Na-K-ATPase activity. Tokyo-toritsu Eisei Kenkyu Nenpo, 49, 60-64.
60. Lee, S.H.; Park, J.S.; Kim, S.Y.; Kim, J.J.; Chung, S.R. (1998) Isolation of inhibitory components on tyrosinase activity from the bark of Paeonia moutan. Yakhak Hoechi, 42, 353-358.
61. Shoyama, Y.; Yamada, Y.; Nishioka, I.; Matsunaka, H. (1990) Depigmentation and inhibition of cell growth of β-16 Melanoma cells by compounds isolated from Paeonia suffruticosa callus. Plant Cell Rep., 8, 711-713.
62. Zhang, Y.J.; Tanaka, T.; Zwamoto, Y.; Yang, C.R.; Kouno, I. (2000) Novel Norsesquiterpenoids from the roots of Phyllanthus emblica. J. Nat. Prod., 63, 1507-1510.
63. Tanaka, T.; Kouna, I. (1996) Whisky lactone precursors from the wood for Platycarya strobilacea. J. Nat. Prod., 59, 997-999.
64. Tanaka, T.; Nonaka, G.; Nishioka, I. (1985) Tannins and related compounds, part 30, punicafolin, an ellagitannin from the leaves of Punica granatum. Phytochemistry, 24, 2075-2078.
65. Tanaka, N.; Shimomura, K.; Ishimaru, K. (1995) Tannin production in callus cultures of Quercus acutissima. Phytochemistry, 40, 1151-1154.
66. Nonaka, G.; Sakai, T.; Mihashi, K.; Nishioka, I. (1991) Tannins and related compounds. CIX Isolation of alienating A and B, Novel C, C-linked ellagitannin dimmers from Quercus Aliena Blume. Chem. Pharm. Bull., 39, 884-888.
67. Regerat, F.; Pourrat, H.; Pourrat, A. (1989) Hydrolysis by fermentation of tannins from gall nuts. J. Ameri. Leather Chem. Assoc., 84, 323-328.
68. Nishizawa, M.; Yamagishi, T.; Nonaka, G.; Nishioka, I. (1983) Tannins and related compounds. Part 9. Isolation and characte-rization of polygalloylglucoses from Turkish galls (Quercus infectoria). J. Chem. Soc. Perk. Trans. Organ. Bioorg. Chem., 961-965.
69. Nonaka, G.; Nakayama, S.; Nishioka, I. (1989) Tannins and related compounds. LXXXIII. Isolation and structures of hydrolysable tannins, phillyraeoidins A-E from Quercus phillyraeoides. Chem. Pharm. Bull., 37, 2030-2036.
70. Farag, S.F.; El-Emary, N.A.; Niwa, M. (1998) Gallotannins from Quercus robur cultivated in Egypt. Bull. Pharm. Sci., 21, 1-6.
71. Vivas, N.; Laguerre, M.; Glories, Y.; Bourgeois, G.; Vitry, C. (1995) Structure simulation of two ellagitannins from Quercus robur L. Phytochemistry, 39, 1193-1199.
72. Scalbert, A.; Duval, L.; Monsties, B.; Favre, J.M. (1988) Polyphenols of Quercus robur. Ellagitannin of adult trees, calli and mircopropagated plants. Polyphenols, 14, 262-2645.
73. Cammann, J.; Denzel, K.; Schilling, G.; Gross, G.G. (1989) Biosynthesis of gallotannins: β-glucogallin-dependent formation of 1, 2, 3, 4, 6-pentagalloylglucose by enzymatic galloylation of 1, 2, 3, 6-tetragalloylglucose. Arch. Biochem. Biophys., 273, 58-63.
74. Schmidt, S.W.; Denzel, K.; Schilling, G.; Gross, G.G. (1987) Enzymatic synthesis of 1,6-digalloylglucose from β-glucogallin by β-glucogallin: β-glucogallin-6-O-galloyltransferase from oak leaves. J. Biosci., 42, 87-92.
75. Krajci, I.; Gross, G.G. (1986) Formation of gallotannins in callus culture from oak (Quercus robur). Phytochemistry, 26, 141-143.
76. Yu, W.S.; Chen, X.; Li, H.; Yang, Lei. (1993) Polyphenols from Rhodiola crenulata. Planta Med., 59, 80-82.
77. Yu, W.; Chen, X.; Yang, L.; Li, H.; Li, Y. (1992) Polyphenols constituents of Rhodiola crenulata. Tianran Chanwu Yanjiu Yu Kaifa, 4, 23-28.
78. Lou, H.; Zuo, C. (1990) Studies on the chemical constituents of Rhodiola henry (I). Zhongcaoyao, 21, 194-199.
79. Mook-Jung, I.; Kim, H.; Fan, W.; Tezuka Y.; Kadota, S.; Nishijo, H.; Jung, M. (2002) Neuroprotective effects of constituents of the oriental crude drugs, Rhodiola sacra, Rhodiola sachalinesis and tokaku-jok-to, against β-amyloid toxicity, oxidative stress and apoptosis. Biol. Pharm. Bull., 25, 1101-1104.
80. Tan, W.; Tezuka, Y.; Ni, K.M.; Kadota, S. (2001) Prolyl endopeptidase inhibitors from the underground part of Rhodiola sachalinesis. Chem. Pharm. Bull., 49, 396-401.
81. Jiang, Z.; Tanaka, T.; Kouno, I. (1999) Three novel C-glcosidic ellagitannins, Rhoipteleanins H, I and J from Rhoiptlea chiliantha. J. Nat. Prod., 62, 425-429.
82. Cha, B.C.; Lee, S.B.; Rhim, T.J.; Lee, K.H. (2000) Constituents of anti oxidative activity and free radical scavenging effect from Galla Rhois (Rhus javanica Linne). Saengyak Hakhoechi, 31, 185-189.
83. Chung, S.C.; Hwang, B.Y.; Oh, G.J.; Kang, S.J.; Kim, M.J.; Choi, W.H.; Lee, K.S.; Ro, J.S. (1999) Chemical components from stem bark of Rhus Javanica. Saengyak Hakhoechi, 30, 295-300.
84. Kim, H.J.; Yang, D.; Choi, S.W. (1997) Inhibitors of tyrosinase and melanogenesis from Galla rhois. J. Food Scien. Nutr., 2, 285-290.
85. Fröhlich, B.; Niemetz, R.; Gross, G.G. (2002) Gallotannin biosynthesis: two new galloyltransferases from Rhus typhina leaves, preferentially acylating hexa- and heptagalloylglucoses. Planta, 216, 168-172.
86. Niemetz, R.; Gross, G.G.; Molekulare, B. (2001) Gallotannin biosynthesis: β-glucogallin: Hexagalloyl 3-O-galloyltransferase from Rhus typhina leaves. Phytochemistry, 58, 657-661.
87. Hofmann, A.S.; Gross, G.G. (1990) Biosynthesis of gallotannins: formation of polygalloylglucose by enzymes acylating of 1, 2, 3, 4, 6-penta-O-galloylglucose. Arch. Biochem. Biophys., 283, 530-532.
88. Fröhlich, B.; Niemetz, R.; Gross, G.G. (2001) Gallotannin biosynthesis-two new galloyltransaferases from Rhus typhina leaves preferentially acylating Hexa- and heptagalloylglucoses. Planta, 216, 168-172.
89. Jin, Z.; Piao, Y.; Wang, Z.; Dong, S. (1994) Tannin constituents of Rosa davurica fruits. Zhongcaoyao, 25, 64-67.
90. Yoshida, T.; Jin, Z.; Okuda, T. (1989) Tannins of rosaceous medical plants, Part 6, Taxifolin apioside and davuriciin M1, a hydrolysable tannin from Rosa davurica. Phytochemistry, 28, 2177-2181.
91. Cui, C.; Zhao, Q.; Cai, B.; Yao, X.; Osadsa, H. (2002) Two new and four known polyphenolics obtained as new cell-cycle inhibitors from Rubus alceaefolius Poir. J. Asia. Nat. Prod. Res. 4, 243-252.
92. Zhao, Q.; Cui, C.; Cai, B.; Yao, X.; Osade, H. (2001) One new and known hydrolysable tannins obtained as new cell cycle inhibitors from Rubus aleaefolius poir. Zhongguo Yaowu Huaxue Zashi, 11, 343-344.
93. Ishimaru, K.; Hirose, M.; Takahashi, K.; Koyama, K.; Shimomura, K. (1990) Tannin production in root culture of Sanguisorba officinalis. Phytochemistry, 29, 3827-3830.
94. Tanaka, T.; Nonaka, G.; Nishioka, I. (1983) Tannins and related compounds. Part 14, 7-O-galloyl-(+)-catechin and 3-O-galloylpro-cyanidin B-3 from Sanguisorba officinalis. Phytochemistry, 22, 2575-2578.
95. Yokozawa, T.; Chen, C.; Tanaka, T.; Kitani, K. (2000) A study on the nitric oxide production-suppressing activity of Sanguisorba radix components. Chem. Pharm. Bull., 23, 717-722.
96. Neera, S.; Arakawa, H.; Ishimaru, K. (1992) Tannin production in Sapium sebiferum callus cultures. Phytochemistry, 31, 4143-4149.
97. Neera, S.; Ishimaru, K. (1992) Tannin production in cell cultures of Sapium sebiferum. Phytochemistry, 31, 833-836.
98. Hayashi, Y.; Nagagama, K.; Arisawa, M.; Shimizu, M.; Suzuki, S.; Yoshizak, M.; Morita, N.; Ferro, E.; Basualdo, I.; Berganza, L.H. (1989) Pentagalloylglucose, a xanthine oxidase inhibitor from a Paraguayan crud drug (Molle/Schinus terebinthifolius). J. Nat. Prod., 52, 210-211.
99. Kurata, H.; Wang, J.; Narui, T.; Hashimotom, T.; Okuyama, T. (1990) Haematological studies on naturally occurring substances, Part IV. Constituents of Chinese astringent drugs (Kojuyaku) on blood coagulation and fibrinolysis systems. Shoyakugaku Zasshi, 44, 101-104.
100. Connell, R.J.P.; Farmer, P.; Walker, J.M. (1988) Purification and characterization of pentagalloylglucose and α-glycosidase inhibitor/ antibiotic from the freshwater green alga spirogyra varians. Biochem. J., 255, 937-941.
101. Nishizawa, M.; Yamagishi, T.; Nonaka, G.; Nishioka, I.; Ragan, M.A. (9185) Tannins and related Compounds, Part 34, gallotannins of the freshwater green alga Spirogyra SP. Phytochemistry, 24, 2411-2413.
102. Tanaka, T.; Urii, Y.; Nonaka, G.; Nishioka, I. (1993) Tannins and related compounds CXXIII. Chromone acctophenone and phenyl-propanoid glycosides and their galloyl and/or hexahydroxy-diphenoyl esxers from the leaves of Syzygium aromaticum Merr. ET Perry. Chem. Pharm. Bull., 41, 1232-1237.
103. Niemetz, R.; Gross, G.G.; Schilling, G. (2001) Ellagitannin biosynthesis: oxidation of pentagalloylglucose to tellimagrandin II by an enzyme from Tellima grandiflora leaves. Chem. Comm., 35-36.
104. Kandil, F.E.; Nassar, M.I. (1998) A tannin anticancer promoter from Terminalia aijuna. Phytochemistry, 47, 1567-1568.
105. Ahn, M.J.; Kim, C.Y.; Lee, J.S.; Kim, T.G.; Kim, S.H.; Lee, C.K.; Lee, B.B.; Shin, C.G.; Huh, H.; Kim, J. (2002) Inhibition of HIV-1 integrase by galloylglucoses from Terminalia chebula and flavonol glycoside gallates from Euphorbia Pekinensis. Planta Med., 68, 457-459.
106. Lee, S.H.; Ryu, S.Y.; Choi, S.U.; Lee, C.O.; No, Z.; Kim, S.K.; Ahn, J.W. (1995) Hydrolysable tannins and related compound having cytotoxic activity from the fruits of Terminalia chebula. Arch. Pharm. Res., 18, 118-120.
107. Burapadaja, S.; Bunchoo, A. (1995) Antimicrobial activity of tannins from Terminalia citrina. Plant. Med., 61, 365-366.
108. Yoshida, T.; Chou, T.; Nitta, A.; Miyamoto, K.; Koshiura, R.; Okuda, T. (1990) Woodfordin C, a macro-ring hydrolysable tannin dimmer with antitumor activity, and accompanying dimmers from Woodfordia fruticosa flowers. Chem. Pharm. Bull., 38, 1211-1217.
109. Yoshida, T.; Chou, T.; Nitta, A.; Okuda, T. (1989) Woodfordins A, B, and C, dimeric hydrolysable tannins from Woodfordia fruticosa flowers. Heterocycles, 29, 2267-2271.
110. Okuda, T.; Mori, K.; Hayazu, H. (1985) Inhibitory effects of oriental pharmaceutical tannins on mutagen. Wakan Lyaku Gakkaishi, 2, 168-169.
111. Lee, S.H.; Park, J.S.; Kim, S.Y.; Chung, S.R.; Choi, S.U. (1997) Cytotoxic effects of hydrolysable tannins from some euphorbia plants on the human tumour cell lines. Yakhak Hoechi, 41, 524-529.
112. Sakai, Y.; Ose, Y.; Nagase, H.; Kito, H.; Sato, T.; Kawai, M.; Mizuno, M. (1989) Effects of constituents of Peony root on the mutagenicity of benzo[a]pyrene. Eisei Kayaku, 35, 433-443.
113. Hatano, T.; Yasuhara, T.; Yoshihara, R.; Agata, I.; Noro, T.; Okuda, T. (1990) Effects of interaction of tannins with co-existing substances VII, inhibitory effects of tannins and related polyphenols on xanthine oxidase. Chem. Pharm. Bull., 38, 1224-1229.
114. Chen, W.J.; Chang, C.Y.; Lin, J. (2003) Induction of G1. phase arrest in MCF human breast cancer cells by pentagalloylglucose through the down-regulation of CDK4 and CDK2 activities and up-regulation of the CDK inhibitors p27kip and p21Cip. Biochem. Pharmacol., 65, 1777-1785.
115. Pan, M.H.; Lin, J.H.; Lin-shiau, S.Y.; Lin, T.K. (199) Induction of apoptosis by penta-O-gallyl-β-D-glucose through activation of caspase-3 in human leukaemia HL-60 cells. Eur. J. Pharmacol., 381, 171-183.
116. Feldman, K.S.; Sahasrabudhe, K.; Smith, R.S.; Scheuchenzuber, W.J. (1999) Immunostimulation by plant polyphenols: a relationship between tumour necrosis factor-α production and tannin structure. Bioorg. Med. Chem. Lett., 9, 985-990.
117. Feldman, K.S.; Sahasrabudhe, K; Lawlor, M.D.; Wilson, S.L.; Lang, C.H.; Scheuchenzuber, W.J. (2001) In vitro and in vivo inhibition of LPS-stimulated tumor necrosis factor-α accretion by the gallotannin β-D-pentagalloylglucose. Bioorg. Med. Chem. Lett., 11, 1813-1815.
118. Noro, T.; Ohki, T.; Nods, Y.; Warashina, T.; Noro, K.; Tomita, I.; Nukamura, Y. (1999) Inhibitory effects of hydrolysable tarmins on tumour promoting activates induced by 12-O-tetradecanoyl-phorbol-13-acetate in JB6 mouse epidermal cells. Basic Life Sci., 66, 665-673.
119. Bhimani, R.S.; Troll, W.; Grunberger, D.; Frenkel, K. (1993) Inhibition of oxidative stress in Hela cells by chemopreventive agents. Cancer Res., 53, 4528-4533.
120. Yoshizawa, S.; Horiuchi, T.; Suganuma, M.; Nishiwaki, S.; Yatsunami, J.; Okabe, S.; Okuda, T.; Muto, Y.; Frenkel, K. (1992) Penta-O-galloyl-β-D-glucoses and (-)-epigallocatechin gallate, cancer preventive agents. ACS Symp. Ser., 507, 316-325.
121. Lee, S.J.; Lee, I.S.; Mar, W. (2003) Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 activity by 1, 2, 3, 4, 6-penta-O-galloyl-β-D-glucose in murine macrophage cells. Arch. Pharm. Rev., 26, 832-839.
122. Ho, L.L.; Chen, W.; Lin, S.Y.; Lin, J. (2002) Penta-O-galloyl-β-D-glucose inhibits the invasion of mouse melanoma by suppressing metalloproteinase-9 through down regulation of activator protein-1. Eur. J. Pharmacol., 453, 149-158.
123. Oh, G.S.; Pae, H.O.; Oh, H.; Hong, S.G.; Kim, I.K.; Chai, K.Y.; Yun, Y.G.; Kwon, T.O.; Chung, H.T. (2001) In vitro anti-proliferative effect of 1, 2, 3, 4, 6-penta-O-galloyl-β-D-glucose on human hepatocellular carcinoma cell line, SK-HEP-1 cells. Cancer Lett., 174, 17-24.
124. Kickuskie, R.E.; Kashiwada, Y.; Nonaka, G.; Nishioka, I.; Bodner, A.J.; Cheng, Y.C.; Lee, K.H. (1992) Anti-AIDs agents. 8, HIV and reverse transcriptase inhibition by tannins. Bioorg. Med. Chem. Lett., 2, 1529-1534.
125. Kakiuchi, N.; Hattori, M.; Namba, T.; Nishizawa, M.; Yamagishi, T.; Okuda, T. (1985) Inhibitory effect of tannins on reverse transcriptase from RNA tumour virus. J. Nat. Prod., 48, 614-621.
126. Nakashima, H.; Murakami, T.; Yamamoto, N.; Sakagami, H.; Tanuma, S.; Hatano, T.; Yoshida, T.; Okuda, T. (1992) Inhibition of human immunodeficiency viral replication by tannins and related compounds. Antiviral Res., 18, 91-103.
127. Nakashima, H.; Ichiyama, K.; Hirayama, F.; Uthino, K.; Ito, M.; Saitoh, T.; Ueki, M.; Yamamoto, N.; Ogawara, H. (1996) Sulfated penta galloylglucose (Y-ART-3) inhibits HIV replication and cytopathic effects in vitro, and reduces HIV infection in hu-PBL-SCID mice. Antiviral Res., 30, 95-108.
128. Fukuchi, K.; Sakagami, H.; Okuda, T.; Hatano, T.; Tanuma, S.; Kitajima, K.; Inoue, Y.; Znoue, S.; Ichikawa, S. (1989) Inhibition of herpes simplex virus infection by tannins and related compounds. Antiviral Res., 11, 285-297.
129. Takehara, M.; Takechi, M.; Tanaka, Y. (1986) In vitro antiviral effects of 1, 2, 3, 4, 6-pentagalloylglucose against herpes simplex virus. ICMR Ann., 6, 207-214.
130. Takehara, M.; Takechi, M.; Tanaka, Y. (1985) Studies on antiviral activity of several hydrolysable tannins. Int. Cong. Ser., 667, 223-224.
131. Takechi, M.; Tanaka, Y.; Takehara, M.; Nonaka, G.; Nishioka I. (1985) Structure and antiherpetic activity among tannins. Phytochemistry, 24, 2245-2250.
132. Park, J.K.; Cho, H.J.; Lim, Y.; Cho, Y.H.; Lee, C.H. (2002) Hypocholecterolemic effects of CJ90002 in hamsters: a potent inhibitor for squalene synthase from Paeonia moutan. J. Microbiol. Biotechnol., 12, 222-227.
133. Li, Y.S.; Kim, J.; Li, J.; Liu, F.; Liu, X.Q.; Himmeldirk, K.; Rea, Y.; Wagner, T.E.; Chen X.Z. (2005) Natural anti-diabetic compound 1,2,3,4,6-penta-O-galloyl-D-glucopyranose binds to insulin receptor and activates insulin-mediated glucose transport signaling pathway. Biochem. Biophy. Res. Comm., 336, 430-437.
134. Ren, Y.; Himmeldirk, K.; Chen, X.Z. (2006) Synthesis and SAR study of antidiabetic pentagalloylglucose (PGG) and its analogs. J. Med. Chem., 49, 2829-2837.
135. Pan, M.H.; Lin-Shiau, S.Y.; Ho, C.T.; Lin, J.H.; Lin, J.K. (2000) Suppression of lipopolysaccharide-induced nuclear factor-KB activity by theaflavin-3,3™-digallate from black tea and other polyphends through down-regulation of IKB kinase activity in macrophages. Biochem. Pharmacol., 59, 357-367.
136. Kakegawa, H.; Matsumoto, H.; Endo, K.; Satoh, T.; Nonaka, G.; Nishioka, I. (1995) Inhibitory effects of tannins on Hyaluronidase activation and on the degranulation from rat mesentery mast cells. Chem. Pharm. Bull., 33, 5079-5082.
137. Bors, W.; Michel. C. (2001) Structure-activity-relationships governing antioxidant capacities of plant polyphenols. Methods Enzymol., 335, 166-180.
138. Fujita, Y.; Komagoe, K.; Niwa, Y.; Uehara, I.; Hara, R.; Mori, H.; Okuda, T.; Yoshida, T. (1988) Studies on inhibition mechanism of autoxidation by tannin and flavonoids III: inhibition mechanism of tannins isolated from medicinal plants and related compounds on autoxidation of methyl linoleate. Yakugaku Zasshi, 108, 528-537.
139. Tanaka, N.; Nishikawa, K.; Ishimaru K. (2003) Antioxidative capacity of extracts and constituents in Cornus capitata adventitious roots. J. Agri. Food Chem., 51, 5906-5910.
140. Okubo, T.; Nagai, F.; Seto, T.; Satoh, K.; Ushiyama, K.; Kano, I. (2000) The inhibition of phenylhydroguinone-induced oxidative DNA cleavage by constituents of Moutan cortex and Paeoniae radix. Biol. Pharm. Bull., 23, 199-203.
141. Westenburg, H.E.; Lee, K.J.; Lee, S.K.; Fong, H.H.S.; Breemen, R.B.V.; Pezzuto, J.M A.; Kinghorm, D. (2000) Activity-guided isolation of antioxidative constitutents of Cotinus coggygria. J. Nat. Prod., 63, 1696-1698.
142. Yokozawa, T.; Chen, C.; Dong, E.; Tanaka, T.; Nonaka, G.I.; Nishioka, I. (1998) Study on the inhibitory effect of tannins and flavonoids against the 1, 1-diphenyl-2-picrylhydrazyl radical. Biochem. Pharmacol., 56, 213-222.
143. Hong, C.Y.; Wang, C.P.; Huang, S.S.; Hsu, F.L. (1995) The inhibitory effect of tannins lipid peroxidation of rat heart mitochondria. J. Pharm. Pharmacol., 47, 138-142.
144. Hatano, T.; Edamatsu, R.; Hiramatsu, M.; Mori, A.; Fujita, Y.; Yasuhara, T.; Yoshida, T.; Okuda, T. (1989) Effects of the interaction of tannins with co-existing substances. VI. Effects of tannins and related polyphends on superoxide anion radical, and on 1, 1-diphenyl-2-picrylhydrazyl radical. Chem. Pharm. Bull., 37, 2016-2021.
145. 2 and ascorbic acid on the scavenger effect of tannins, measured on superoxide anion, application to red wines. Vitis, 36, 91-96.
146. Yoshida, T.; Mori, K.; Hatano, T.; Okumura, T.; Uehara, I.; Komagoe, K.; Fujita, Y.; Okuda, T. (1989) Studies on inhibition mechanism of autoxidation by tannins and flavonoids. V. Radical-scavenging effects of tannins and related polyphenols on 1, 1-diphenyl-2-picrylhydrazyl radical. Chem. Pharm. Bull., 37, 1919-1921.
147. Choi, B.M.; Kim, H.J.; Oh, G.S.; Pae, H.O.; Oh, H.; Teong, S.; Kwon, T.O.; Kim, Y.; Chung, H.T. (2002) 1, 2, 3, 4, 6-penta-0-galloyl-β-D-glucose protects rat neuronal cells (neuro2A) from hydrogen peroxide mediated cells death via the induction of heme oxygenase-1. Neurosci. Lett., 328, 185-189.
148. Konishi, K.; Tanaka, T. (1999) Inhibitory effects of tannins on the NADH dehydrogenase activity of bovine heart mitochondrial complex I. Biol. Pharm. Bull., 22, 240-243.
149. Adachi, H.; Konishi, K.; Horikoshi, I. (1992) Inhibitory effects of pentagalloylglucose on reduced nicotinamide adenine dinucleatide dehydrogenase of photobacterium phosphoreum. Chem. Pharm. Bull., 40, 718-720.
150. Konishi, K.; Adachi, H.; Kita, K.; Horikoshi I. (1990) Inhibitory effects of galloylglucose on nicotinamide adenine dinucleotide dehydrogenase of the aerobic respiratory chain of Escherichia coli. Chem. Pharm. Bull., 38, 474-476.
151. Konishi, K.; Adachi, H.; Ishigaki, N.; Kanamura, Y.; Adachi, I.; Tanaka, T.; Nishioka, I.; Nonaka, G.; Horikoshi, I. (1993) Inhibitory effects of tannins on NADH dehydrogenases of various organisms. Biol. Pharm. Bull., 16, 716-718.
152. Adachi, H.; Konishi, K.; Kita, K.; Horikoshi, I. (1988) Inhibitory effects of pentagalloylglucose on the respiratory chain of photobacterium phosphoreum. Chem. Pharm. Bull., 36, 2499-2505.
153. Matsuo, K.; Kobayashi, M.; Takuno, Y.; Kuwajima, H.; Ito, H.; Yoshida,T. (1997) Anti-tyrosinase activity constituents of Arctostaphylos uva-ursi. J. Pharm. Socie. Jap., 117, 1028-1032.
154. Kim, J.J.; Lee, J.S.; Kim, S.Y.; Kim, J.A.; Chung, S.R.; Jang, T.S. (2001) Inhibitory effects of hydrolysable tannins from Euphorbia helioscopia on mushroom tyrosinase activity in vitro. Yakhak Hoechi, 45, 214-219.
155. Yokozawa, T.; Chen, C.P.; Tanaka, T. (2000) Direct scavenging of nitric oxide by traditional crude drugs. Phytomedicine, 6, 453-463.
156. Adachi, H.; Konishi, K.; Horikoshi I. (1989) The effects of 1,2,3,4,6-penta-O-galloyl-β-D-glucose on rat liver mitochondrial respiration. Chem. Pharm. Bull., 37, 1341-1344.
157. Nishizawa, M.; Yamagishi, T.; Ohyama, T. (1983) Inhibitory effect of gallotannins on the respiration of rat liver mitochondria. Chem. Pharm. Bull, 31, 2150-2152.
158. Sawada, H.; Hamatake, M.; Hara, A.; Nakayama, T.; Deyashiki, Y. (1992) Inhibition of aldose reductase by gallotannins. Gifu Yakka Daigaku Kiyo, 41, 30-36.
159. Aida, K.; Tawata, M.; Shindo, H.; Onaya, T.; Sasaki, H.; Nishimura, H.; Chin, M.; Mitsuhashi, H. (1989) The existence of aldose reductase inhibitors in some kampo medicines. (Oriental herb prescriptions). Planta Med., 55, 22-26.
160. Sawada, H.; Hamatake, M.; Hara, A.; Nakagawa, M.; Nakayama, T. (1989) Inhibition of human placenta aldose reductase by tannic acid. Chem. Pharm. Bull., 37, 1662-1664.
161. Toda, M.; Kawabata, J.; Kasai, T. (2001) Inhibitory effects of ellagi- and gallotannins on rat intestinal α-glycosidase complexes. Bioscien. Biotech. Biochem., 65, 542-547.
162. Toda, M.; Kawabata, J.; Kasai, T. (2000) Inhibitory effect of ellagi- and gallotannins on rat intestinal α-glycosidase inhibitors from clove (Syzygium aromaticum). Biosci. Biotech. Biochem., 64, 294-298.
163. Kolodziej, H.; Kayser, O.; Kiderlen, A. F.; Ito, H.; Hatano, T.; Yoshida, T.; Foo, L.Y. (2001) Anti-leishmanial activity of hydrolysable tannins and their modulatory effects on nitric oxide and tumour-necrosis factor-α release in macrophages in vitro. Planta Med., 67, 825-832.
164. Goto, H.; Shimada, Y.; Akechi, Y.; Kohta, K.; Hattori, M.; Tarasawa, K. (1996) Endothelium-dependent vasodilator effect of extract prepared from the roots of Paeonia lacliflora on isolated rat sorta. Planta Med., 62, 436-439.
165. Rigalleau, G.H.; Caubet, V.; Masquelier, O.; Aubertin, J. (1999) Effects of red wine, tannic acid, or ethanol on glucose tolerance in non-insulin-dependent diabetic patients and on starch digestibility in vitro. Metabolism, 48, 1179-1183.
166. Corder, R.; Douthwaite, J.A.; Lees, D.M.; Khan, N.Q.; Santos, A.C.V.; Wood, E.G.; Carrier, M.J. (2001) Endothelin-1 synthesis reduced by red wine. Nature, 414, 863-864.