The Inhibitory Effects of Tea Polyphenols (Flavan-3-ol Derivatives) on Cu2+ Mediated Oxidative Modification of Low Density Lipoprotein
Tea polyphenols (flavan-3-ol derivatives) suppressed the oxidative modification of low density lipoprotein (LDL) which is assumed to be an important step in the pathogenesis of atherosclerosis lesions. Inhibitory experiments on the oxidative impairment of porcine serum LDL by flavan-3-ols were carri...
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| Published in | Biological & pharmaceutical bulletin Vol. 17; no. 12; pp. 1567 - 1572 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Tokyo
The Pharmaceutical Society of Japan
01.12.1994
Maruzen Japan Science and Technology Agency |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0918-6158 1347-5215 |
| DOI | 10.1248/bpb.17.1567 |
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| Abstract | Tea polyphenols (flavan-3-ol derivatives) suppressed the oxidative modification of low density lipoprotein (LDL) which is assumed to be an important step in the pathogenesis of atherosclerosis lesions. Inhibitory experiments on the oxidative impairment of porcine serum LDL by flavan-3-ols were carried out by incubating them at 37°C in the presence of 5 μM Cu2+. The oxidation of LDL was monitored either by an absorption increase at 234nm due to the conjugated diene formation, or the formation of hydroperoxides and thiobarbituric acid reactive substances (TBARS). It was found that the oxidation was strongly inhibited by various flavan-3-ols, and a lag time over 100 min appeared, depending on the types of flavan-3-ols used. The activities based on the prolongation of the lag time were in the order of (-)-epigallocatechin (EGC)<(+)-catechin (C)<(-)-epicatechin (EC)<(-)-epicatechingallate (ECG)<(-)-epigallocatechingallate (EGCG). IC50 of flavan-3-ols on Cu2+ mediated hydroperoxides and TBARS formation of LDL were 0.90, 0.95μM for ECG and 2.38, 2.74μM for EGC, respectively. It was found that the Cu2+ mediated cholesterol ester degradation in LDL was almost completely inhibited by 5.0μM C or EGCG. Cu2+ mediated apolipoprotein B-100 fragmentation was also inhibited (up to 60%) in the presence of C or EGCG. |
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| AbstractList | Tea polyphenols (flavan-3-ol derivatives) suppressed the oxidative modification of low density lipoprotein (LDL) which is assumed to be an important step in the pathogenesis of atherosclerosis lesions. Inhibitory experiments on the oxidative impairment of porcine serum LDL by flavan-3-ols were carried out by incubating them at 37 degrees C in the presence of 5 microM Cu2+. The oxidation of LDL was monitored either by an absorption increase at 234 nm due to the conjugated diene formation, or the formation of hydroperoxides and thiobarbituric acid reactive substances (TBARS). It was found that the oxidation was strongly inhibited by various flavan-3-ols, and a lag time over 100 min appeared, depending on the types of flavan-3-ols used. The activities based on the prolongation of the lag time were in the order of (-)-epigallocatechin (EGC) < (+)-catechin (C) < (-)-epicatechin (EC) < (-)-epicatechingallate (ECG) < (-)-epigallocatechingallate (EGCG). IC50 of flavan-3-ols on Cu2+ mediated hydroperoxides and TBARS formation of LDL were 0.90, 0.95 microM for ECG and 2.38, 2.74 microM for EGC, respectively. It was found that the Cu2+ mediated cholesterol ester degradation in LDL was almost completely inhibited by 5.0 microM C or EGCG. Cu2+ mediated apolipoprotein B-100 fragmentation was also inhibited (up to 60%) in the presence of C or EGCG. Tea polyphenols (flavan-3-ol derivatives) suppressed the oxidative modification of low density lipoprotein (LDL) which is assumed to be an important step in the pathogenesis of atherosclerosis lesions. Inhibitory experiments on the oxidative impairment of porcine serum LDL by flavan-3-ols were carried out by incubating them at 37°C in the presence of 5 μM Cu2+. The oxidation of LDL was monitored either by an absorption increase at 234nm due to the conjugated diene formation, or the formation of hydroperoxides and thiobarbituric acid reactive substances (TBARS). It was found that the oxidation was strongly inhibited by various flavan-3-ols, and a lag time over 100 min appeared, depending on the types of flavan-3-ols used. The activities based on the prolongation of the lag time were in the order of (-)-epigallocatechin (EGC)<(+)-catechin (C)<(-)-epicatechin (EC)<(-)-epicatechingallate (ECG)<(-)-epigallocatechingallate (EGCG). IC50 of flavan-3-ols on Cu2+ mediated hydroperoxides and TBARS formation of LDL were 0.90, 0.95μM for ECG and 2.38, 2.74μM for EGC, respectively. It was found that the Cu2+ mediated cholesterol ester degradation in LDL was almost completely inhibited by 5.0μM C or EGCG. Cu2+ mediated apolipoprotein B-100 fragmentation was also inhibited (up to 60%) in the presence of C or EGCG. Tea polyphenols (flavan-3-ol derivatives) suppressed the oxidative modification of low density lipoprotein (LDL) which is assumed to be an important step in the pathogenesis of atherosclerosis lesions. Inhibitory experiments on the oxidative impairment of porcine serum LDL by flavan-3-ols were carried out by incubating them at 37 degrees C in the presence of 5 microM Cu2+. The oxidation of LDL was monitored either by an absorption increase at 234 nm due to the conjugated diene formation, or the formation of hydroperoxides and thiobarbituric acid reactive substances (TBARS). It was found that the oxidation was strongly inhibited by various flavan-3-ols, and a lag time over 100 min appeared, depending on the types of flavan-3-ols used. The activities based on the prolongation of the lag time were in the order of (-)-epigallocatechin (EGC) < (+)-catechin (C) < (-)-epicatechin (EC) < (-)-epicatechingallate (ECG) < (-)-epigallocatechingallate (EGCG). IC50 of flavan-3-ols on Cu2+ mediated hydroperoxides and TBARS formation of LDL were 0.90, 0.95 microM for ECG and 2.38, 2.74 microM for EGC, respectively. It was found that the Cu2+ mediated cholesterol ester degradation in LDL was almost completely inhibited by 5.0 microM C or EGCG. Cu2+ mediated apolipoprotein B-100 fragmentation was also inhibited (up to 60%) in the presence of C or EGCG.Tea polyphenols (flavan-3-ol derivatives) suppressed the oxidative modification of low density lipoprotein (LDL) which is assumed to be an important step in the pathogenesis of atherosclerosis lesions. Inhibitory experiments on the oxidative impairment of porcine serum LDL by flavan-3-ols were carried out by incubating them at 37 degrees C in the presence of 5 microM Cu2+. The oxidation of LDL was monitored either by an absorption increase at 234 nm due to the conjugated diene formation, or the formation of hydroperoxides and thiobarbituric acid reactive substances (TBARS). It was found that the oxidation was strongly inhibited by various flavan-3-ols, and a lag time over 100 min appeared, depending on the types of flavan-3-ols used. The activities based on the prolongation of the lag time were in the order of (-)-epigallocatechin (EGC) < (+)-catechin (C) < (-)-epicatechin (EC) < (-)-epicatechingallate (ECG) < (-)-epigallocatechingallate (EGCG). IC50 of flavan-3-ols on Cu2+ mediated hydroperoxides and TBARS formation of LDL were 0.90, 0.95 microM for ECG and 2.38, 2.74 microM for EGC, respectively. It was found that the Cu2+ mediated cholesterol ester degradation in LDL was almost completely inhibited by 5.0 microM C or EGCG. Cu2+ mediated apolipoprotein B-100 fragmentation was also inhibited (up to 60%) in the presence of C or EGCG. |
| Author | TOMITA, Takako MIURA, Shinji WATANABE, Junichi TOMITA, Isao SANO, Mitsuaki |
| Author_xml | – sequence: 1 fullname: SANO, Mitsuaki – sequence: 1 fullname: MIURA, Shinji – sequence: 1 fullname: WATANABE, Junichi – sequence: 1 fullname: TOMITA, Isao – sequence: 1 fullname: TOMITA, Takako |
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| Copyright | The Pharmaceutical Society of Japan 1995 INIST-CNRS Copyright Japan Science and Technology Agency 1994 |
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| Keywords | Lipoprotein LDL Tea Polyphenol Plant origin Lipids Oxidation Antioxidant Metabolism |
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| References_xml | – reference: 33) K. Muramatsu, M. Fukuyo, Y. Hara, J. Nutr. Sci. Vitaminol., 32, 613 (1986). – reference: 5) I.N. Trakht, K.A. Kovaleva, E.V. Janushevskaya, T.S. Balmukhanov, O.Y. Printseva, S.N. Preobrazhensky, M.M. Peklo, V.P. Tsibulsky, S.N. Pokrovsky, "Atherosclerosis Reviews," Vol. 17, eds. by R. I. Levy, A.N. Klimov, V.N. Smirnov, H.A. Tyroler, Raven Press, New York, 1988, p. 51. – reference: 27) K. Akasaka, T. Suzuki, H. Ohrui, H. Meguro, Anal. Lett., 20, 797 (1987). – reference: 14) U.P. Steinbrecher, S. Parthasarathy, D.S. Leake, J.L. Witztum, D. Steinberg, Proc. Natl. Acad. Sci. U.S.A., 81, 3883 (1984). – reference: 17) T.E. Carew, D.C. Schwenke, D. Steinberg, Proc. Natl. Acad. Sci. U.S.A., 84, 7725 (1987). – reference: 2) M.E. Haberland, D. Fong, G.L. Chen, Science, 241, 215 (1988). – reference: 28) E.G. Bligh, W.J. Dyer, Can. J. Biochem. Physiol., 37, 911 (1959). – reference: 38) E.R. Stadtman, "Medical, Biochemical and Chemical Aspects of Free Radicals," eds. by O. Hayashi, E. Niki, M. Kondo, T. Yoshikawa, Elsevier Science Publ., Amsterdam, 1989, p. 11. – reference: 1) D. Steinberg, S. Parthasarathy, T.E. Carew, J.C. Khoo, J.L. Witztum, New Engl. J. Med., 320, 915 (1989). – reference: 4) M. Shaikh, S. Martini, J.R. Quiney, P. Baskerville, A.E. la Ville, N. L. Browse, R. Duffield, P.R. Turner, B. Lewis, Atherosclerosis, 69, 165 (1988). – reference: 35) G.S. Boyd, E.B. Mawer, Biochem. J., 81, 11 (1961). – reference: 6) D.C. Schwenke, T.E. Carew, Arteriosclerosis, 9, 895 (1989). – reference: 9) H. Esterbauer, M. Dieber-Rotheneder, G. Waeg, G. Striegl, G. Jurgens, Chem. Res. Toxicol., 3, 77 (1990). – reference: 29) H. Ohkawa, N. Ohishi, K. Yagi, Anal. Biochem., 95, 351 (1979). – reference: 22) K. Shimoi, Y. Nakamura, I. Tomita, Y. Hara, T. Kada, Mutat. Res., 173, 239 (1986). – reference: 13) D.W. Morel, J.R. Hessler, G.M. Chisolm, J. Lipid Res., 24, 1070 (1983). – reference: 26) K. Akasaka, T. Suzuki, H. Ohrui, H. Meguro, Anal. Lett., 20, 731 (1987). – reference: 18) T. Lunder, Farm. Tijdschr. Belg., 66, 34 (1989). – reference: 30) L.L. Abell, B.B. Levy, B.B. Brodie, F.E. Kendall, Anal. Biochem., 357 (1951). – reference: 24) B.H. Chung, J.P. Segrest, M.J. Ray, J.D. Brunzell, J.E. Hokanson, R.M. Krauss, K. Beaudrie, J.T. Cone, "Methods in Enzymology," Vol. 128, eds. by J.P. Segrest, J.J. Albers, Academic Press, Inc., Orlando, 1986, p. 181. – reference: 3) W. Palinski, M.E. Rosenfeld, S. Yla-Herttuala, G.C. Gurtner, S.S. Socher, S.W. Butler, S. Parthasarathy, T.E. Carew, D. Steinberg, J.L. Witztum, Proc. Natl. Acad. Sci. U.S.A., 86, 1372 (1989). – reference: 11) H. Esterbauer, G. Striegl, H. Puhl, M. Rotheneder, Free Rad. Res. Commun., 6, 67 (1989). – reference: 34) H. Mangiapane, J. Thomson, A. Salter, S. Brown, G.D. Bell, D. A. White, Biochem. Pharmacol., 43, 445 (1992). – reference: 12) S. Bedwell, R.T. Dean, W. Jessup, Biochem. J., 262, 707 (1989). – reference: 15) S. Parthasarathy, D.J. Printz, D. Boyd, L. Joy, D. Steinberg, Arteriosclerosis, 6, 505 (1986). – reference: 31) T. Okuda, Y. Kimura, T. Yoshida, T. Hatano, H. Okuda, S. Arichi, Chem. Pharm. Bull., 31, 1625 (1983). – reference: 36) G.S. Boyd, Fed. Proc., Am. Soc. Exp., 21, Part II, 86 (1962). – reference: 20) K. Yoshino, Y. Hara, M. Sano, I. Tomita, Biol. Pharm. Bull., 17, 146 (1994). – reference: 16) T. Kita, Y. Nagano, M. Yokode, K. Ishii, N. Kume, A. Ooshima, H. Yoshida, C. Kawai, Proc. Natl. Acad. Sci. U.S.A., 84, 5928 (1987). – reference: 8) H. Esterbauer, J. Gebicki, H. Puhl, G. Jurgens, Free Rad. Biol. Med., 13, 341 (1992). – reference: 23) Y. Nakamura, S. Harada, I. Kawase, M. Matsuda, I. Tomita, "Proceedings of the International Symposium on Tea Science (ISTS)," ed. by the Organizing Committee of ISTS, Kurofune Printing Co., Ltd., Shizuoka, 1991, pp. 205-209. – reference: 7) M.T. Quinn, S. Parthasarathy, D. Steinberg, Proc. Natl. Acad. Sci. U.S.A., 82, 5949 (1985). – reference: 25) O.H. Lowry, N.J. Rosebrough, A.L. Farr, R.J. Randall, J. Biol. Chem., 193, 265 (1951). – reference: 32) T. Matsuzaki, Y. Hara, Nippon Nogei Kagaku Kaishi, 59, 129 (1985). – reference: 21) K. Yoshino, I. Tomita, M. Sano, I. Oguni, Y. Hara, M. Nakano, Age, 17, 79 (1994). – reference: 37) K. Sato, E. Niki, Arch. Biochem. Biophys., 279, 402 (1990). – reference: 10) H. Esterbauer, G. Jurgens, O. Quehenberger, E. Koller, J. Lipid Res., 28, 495 (1987). – reference: 19) M. Sano, Y. Takahashi, C. Komatsu, Y. Nakamura, K. Shimoi, I. Tomita, I. Oguni, K. Nasu, K. Obata, H. Konomoto, T. Masuzawa, N. Suzuki, "Proceedings of the International Symposium on Tea Science (ISTS)," ed. by the Organizing Committee of ISTS, Kurofune Printing Co., Ltd., Shizuoka, 1991, pp. 304-308. |
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| SubjectTerms | Animals antioxidative activity Apolipoproteins B - chemistry atherosclerosis Benzopyrans - chemistry Biological and medical sciences Catechols - chemistry Cholesterol - blood Copper - chemistry Electrophoresis, Polyacrylamide Gel epigallocatechingallate flavan-3-ol derivative Flavonoids General pharmacology lipid peroxidation Lipid Peroxides - chemistry Lipoproteins, LDL - blood Lipoproteins, LDL - chemistry low density lipoprotein Medical sciences Oxidation-Reduction Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Phenols - chemistry Polymers - chemistry Swine Tea - chemistry Thiobarbituric Acid Reactive Substances - chemistry Thiobarbituric Acid Reactive Substances - metabolism |
| Title | The Inhibitory Effects of Tea Polyphenols (Flavan-3-ol Derivatives) on Cu2+ Mediated Oxidative Modification of Low Density Lipoprotein |
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