Study on the inhibitory effect of tannins and flavonoids against the 1,1-diphenyl-2-picrylhydrazyl radical

Biochemical Pharmacology

Volumn 56, Issue 2, 1998, Pages 213-222

  Yokozawa, Takako ^a   Chen, Cui Ping ^a   Dong, Erbo ^a   Tanaka, Takashi ^b   Nonaka, Gen Ichiro ^c   Nishioka, Itsuo ^c  

^a UNIVERSITY OF TOYAMA   (Japan)

^b NAGASAKI UNIVERSITY   (Japan)

^c KYUSHU UNIVERSITY   (Japan)

Author keywords

1,1 diphenyl 2 picrylhydrazyl; Flavonoid; Radical; Structure activity relationship; Tannin

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; ANTIOXIDANT; FLAVONOID; FREE RADICAL; TANNIN DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; CHINESE MEDICINE; HERB; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

BEPRIDIL; FLAVONOIDS; FREE RADICAL SCAVENGERS; FREE RADICALS; MOLECULAR STRUCTURE; PICRATES; STRUCTURE-ACTIVITY RELATIONSHIP; TANNINS;

EID: 0031727043     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(98)00128-2     Document Type: Article

References (48)

1. Okuda T, Yoshida T and Hatano T, Plants and traditional medicine. In: Economic and Medicinal Plant Research (Eds. Wagner H and Farnsworth NR), Vol. 5, pp. 129-165. Academic Press, New York, 1991.
2. Middleton E Jr, The flavonoids. Trends Pharmacol Sci 5: 335-338, 1984.
3. Halliwell B and Gutteridge JMC, Role of free radicals and catalytic metal ions in human disease: An overview. Methods Enzymol 186 (Part B): 1-85, 1990.
4. Okuda T, Kimura Y, Yoshida T, Hatano T, Okuda H and Arichi S, Studies on the activities of tannins and related compounds from medicinal plants and drugs. I. Inhibitory effects on lipid peroxidation in mitochondria and microsomes of liver. Chem Pharm Bull 31: 1625-1631, 1983.
5. Scott G, Antioxidants in vitro and in vivo. Chem Brit 21: 648-653, 1985.
6. Limasset B, Doucen C, Dore JC, Ojasoo T, Damon M and Crastes de Paulet A, Effects of flavonoids on the release of reactive oxygen species by stimulated human neutrophils. Biochem Pharmacol 46: 1257-1271, 1993.
7. Hong CY, Wang CP, Huang SS and Hsu FL, The inhibitory effect of tannins on lipid peroxidation of rat heart mitochondria. J Pharm Pharmacol 47: 138-142, 1994.
8. Robak J and Gryglewski RJ, Bioactivity of flavonoids. Pol J Pharmacol 48: 555-564, 1996.
9. Rice-Evans CA, Miller NJ and Paganga G, Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 20: 933-956, 1996.
10. Cao G, Sofic E and Prior RL, Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships. Free Radic Biol Med 22: 749-760, 1997.
11. Deby C and Magotteau G, Relation entre les acides gras essentiels et le taux des antioxydants tissulaires chez la souris. CR Soc Biol 164: 267-268, 1970.
12. Tanaka T, Nonaka G, Nishioka I, Miyahara K and Kawasaki T, Tannins and related compounds. Part 37. Isolation and structure elucidation of elaeocarpusin, a novel ellagitannin from Elaeocarpus sylvestris var. ellipticus. J Chem Soc Perkin Trans 1: 369-376, 1986.
13. Saijo R, Nonaka G, Nishioka I, Chen I and Hwang T, Tannins and related compounds. LXXXVII. Isolation and characterization of hydrolyzable tannins from Mallotus japonicus (Thunb.) Mueller-Arg. and M. philippinensis (Lam.) Mueller-Arg. Chem Pharm Bull (Tokyo) 37: 2940-2947, 1989.
14. Nonaka G, Matsumoto Y and Nishioka I, Trapain, a new hydrolyzable tannin from Trapa japonica Flerov. Chem Pharm Bull (Tokyo) 29: 1184-1187, 1981.
15. Tanaka T, Orii Y, Nonaka G and Nishioka I, Tannins and related compounds. CXXIII. Chromone, acetophenone and phenylpropanoid glycosides and their galloyl and/or hexahydroxydiphenoyl esters from the leaves of Syzygium aromaticum Merr. et Perry. Chem Pharm Bull (Tokyo) 41: 1232-1237, 1993.
16. Nishimura H, Nonaka G and Nishioka I, Seven quinic acid gallates from Quercus stenophylla. Phytochemistry 23: 2621-2623, 1984.
17. Ishimaru K, Nonaka G and Nishioka I, Gallic acid esters of proto-quercitol, quinic acid and (-)-shikimic acid from Quercus mongolica and Q. myrsinaefolia. Phytochemistry 26: 1501-1504, 1987.
18. Nonaka G, Ageta M and Nishioka I, Tannins and related compounds. XXV. A new class of gallotannins possessing a (-)-shikimic acid core from Castanopsis cuspidata ver. sieboldii Nakai. Chem Pharm Bull (Tokyo) 33: 96-101, 1985.
19. Nonaka G, Ishimaru K, Tanaka T and Nishioka I, Tannins and related compounds. XVII. Galloylhamameloses from Castanea creneta L. and Sanguisorba officinalis L. Chem Pharm Bull (Tokyo) 32: 483-489, 1984.
20. Tanaka T, Nonaka G and Nishioka I, Tannins and related compounds. XL. Revision of the structures of punicalin and punicalagin, and isolation and characterization of 2-O-galloylpunicalin from the bark of Punica granatum L. Chem Pharm Bull (Tokyo) 34: 650-655, 1986.
21. Lin T, Nonaka G, Nishioka I and Ho F, Tannins and related compounds. CII. Structures of terchebulin, an ellagitannin having a novel tetraphenylcarboxylic acid (terchebulic acid) moiety, and biogenetically related tannins from Terminalia chebula Retz. Chem Pharm Bull (Tokyo) 38: 3004-3008, 1990.
22. Nonaka G, Mihashi K and Nishioka I, Novel metabolites of hexahydroxydiphenic acid esters (ellagitannins) from Carpinus japonica. J Chem Soc Chem Commun 790-791, 1990.
23. Lin J, Ishimatsu M, Tanaka T, Nonaka G and Nishioka I, Tannins and related compounds. XCVI. 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 (Tokyo) 38: 1844-1851, 1990.
24. Nonaka G, Nakayama S and Nishioka I, Tannins and related compounds. LXXXIII. Isolation and structures of hydrolyzable tannins, phillyraeoidins A-E from Quercus phillyraeoides. Chem Pharm Bull (Tokyo) 37: 2030-2036, 1989.
25. Tanaka T, Ishida N, Ishimatsu M, Nonaka G and Nishioka I, Tannins and related compounds. CXVI. Six new complex tannins, guajavins, psidinins and psiguavin from the bark of Psidium guajava L. Chem Pharm Bull (Tokyo) 40: 2092-2098, 1992.
26. Tanaka T, Nonaka G and Nishioka I, 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-11, a novel tetrameric hydrolyzable tannin, and seven related tannins, from Sanguisorba officinalis. J Chem Res (S) 176-177: (M) 2001-2029, 1985.
27. Tanaka T, Tachibana H, Nonaka G, Nishioka I, Hsu F, Kohda H and Tanaka O, Tannins and related compounds. CXXII. New dimeric, trimeric and tetrameric ellagitannins, lambertianins A-D, from Rubus lambertianus Seringe. Chem Pharm Bull (Tokyo) 41: 1214-1220, 1993.
28. Nonaka G, Kawahara O and Nishioka I, Tannins and related compounds. XV. A new class of dimeric flavan-3-ol gallates, theasinensins A and B, and proanthocyanidin gallates from green tea leaf. (1). Chem Pharm Bull (Tokyo) 31: 3906-3914, 1983.
29. Kashiwada Y, Nonaka G and Nishioka I, Tannins and related compounds. XIVIII. Rhubarb. (7). Isolation and characterization of new dimeric and trimeric procyanidins. Chem Pharm Bull (Tokyo) 34: 4083-4091, 1986.
30. Morimoto S, Nonaka G and Nishioka I, Tannins and related compounds. LX. Isolation and characterization of proanthocyanidins with a doubly-linked unit from Vaccinium vitis-idaea L. Chem Pharm Bull (Tokyo) 36: 33-38, 1988.
31. Nonaka G, Nishioka I, Nagasawa T and Oura H, Tannins and related compounds. I. Rhubarb (1). Chem Pharm Bull (Tokyo) 29: 2862-2870, 1981.
32. Tanaka T, Nishimura A, Kouno I, Nonaka G and Young T, Isolation and characterization of yunnaneic acids A-D, four novel caffeic acid metabolites from Salvia yunnanensis. J Nat Prod 59: 843-849, 1996.
33. Nicollier G and Thompson AC, Flavonoids of Desmanthus illinoensis. J Nat Prod 46: 112-117, 1983.
34. Hatano T, Edamatsu R, Hiramatsu M, Mori A, Fujita Y, Yasuhara T, Yoshida T and Okuda T, 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 (Tokyo) 37: 2016-2021, 1989.
35. Nishioka I, The chemistry of tannins (1). J Tradit Sino-Jpn Med 11: 75-81, 1990.
36. Yokozawa T, Fujioka K, Oura H, Nonaka G and Nishioka I, Effects of rhubarb tannins on uremic toxins. Nephron 58: 155-160, 1991.
37. Yokozawa T, Fujioka K, Oura H, Nonaka G and Nishioka I, Effects of rhubarb tannins on renal function in rats with renal failure. Jpn J Nephrol 35: 13-18, 1993.
38. Yokozawa T, Oura H, Hattori M, Iwano M, Dohi K, Sakanaka S and Kim M, Inhibitory effect of tannin in green tea on the proliferation of mesangial cells. Nephron 65: 596-600, 1993.
39. Yokozawa T, Oura H, Sakanaka S, Ishigaki S and Kim M, Depressor effect of tannin in green tea on rats with renal hypertension. Biosci Biotech Biochem 58: 855-858, 1994.
40. Yokozawa T, Fujioka K, Oura H, Tanaka T, Nonaka G and Nishioka I, Uraemic toxin reduction: A newly found effect of hydrolysable-type tannin-containing crude drug and gallotannin. Phytother Res 9: 327-330, 1995.
41. Yokozawa T, Fujioka K, Oura H, Tanaka T, Nonaka G and Nishioka I, Decrease in uraemic toxins, a newly found beneficial effect of Ephedrae Herba. Phytother Res 9: 382-384, 1995.
42. Okuda T, Flavonoids. In: Chemistry of Organic Natural Products (Eds. Mitsuhashi H, Tanaka O, Nozoe S and Nagai M), pp. 219-228. Nankodo, Tokyo, 1992.
43. Yoshida T, Mori K, Hatano T, Okumura T, Uehara I, Komagoe K, Fujita Y and Okuda T, 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 (Tokyo) 37: 1919-1921, 1989.
44. Heilmann J, Merfort I and Weiss M, Radical scavenger activity of different 3′,4′-dihydroxyflavonols and 1,5-dicaffeoylquinic acid studied by inhibition of chemiluminescence. Planta Med 61: 435-438, 1995.
45. Streitwieser A Jr and Heathcock CH, Benzene and the aromatic ring. In: Introduction to Organic Chemistry (Eds. Streitwieser A Jr and Heathcock CH), pp. 637-689, Macmillan Publishing, New York, 1981.
46. Williams RF, Shinkai S and Bruice TC, Radical mechanisms for 1,5-dihydroflavin reduction of carbonyl compounds. Proc Natl Acad Sci USA 72: 1763-1767, 1975.
47. Krol W, Czuba Z, Scheller S, Paradowski Z and Shani J, Structure-activity relationship in the ability of flavonols to inhibit chemiluminescence. J Ethnopharmacol 41: 121-126, 1994.
48. Hu JP, Calomme M, Lasure A, De Bruyne T, Pieters L, Vlietinck A and Vanden Berghe DA, Structure-activity relationship of flavonoids with superoxide scavenging activity. Biol Trace Elem Res 47: 327-331, 1995.