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DOI: 10.1055/s-2001-14337
© Georg Thieme Verlag Stuttgart · New York
Studies on the Hepatocyte Protective Activity and the Structure-Activity Relationships of Quinic Acid and Caffeic Acid Derivatives from the Flower Buds of Lonicera bournei
Publication History
June 8, 2000
August 9, 2000
Publication Date:
31 December 2001 (online)
Abstract
13 quinic acid derivatives along with caffeic acid, methyl caffeate, myo-inositol, bis[5-formylfurfuryl] ether and 6,7-dihydroxycoumarin were isolated from the ethanol extract of the flower buds of Lonicera bournei Hemsl., among which 8 compounds were firstly obtained from this genus. The effects of different solvent soluble fractions of the ethanol extract and the pure compounds on heptocyte death induced by D-galactosamine (D-GalN)/tumor necrosis factor α (TNF-α) were studied, and the structure-activity relationships were also discussed.
Key words
Lonicera bournei Hemsl - Caprifoliaceae - quinic acid derivatives - caffeic acid derivatives - D-galactosamine (D-GalN) - tumor necrosis factor α (TNF-α) - hepatoprotective activity
References
- 1 Chang C W, Lin M T, Lee Sh Sh, Liu K C, Hsu F L, Lin J Y. Differential inhibition of reverse transcriptase and cellular DNA polymerase-α activities by lignans isolated from Chinese herbs, phyllanthus myrtifolius Moon, and tannins from Lonicera japonica Thunb and Castanopsis hystrix . Antiviral Res.. 1995; 27 367-74
- 2 Basnet P, Matsushige K, Hase K, Kadota S, Namba T. Four Di-O-caffeoylquinic acid derivatives from propolis. Potent Hepatoprotective activity in experimental liver injury models. Biol. Pharm. Bull.. 1996; 19 1479-84
- 3 Wang H X, Tang F J, Qiu A Y. Antioxidant composition of honeysuckle. Shipin Yu Fajiao Gongye. 1988; 4 21-31
- 4 Segln P O. Preparation of isolated rat liver cells. Cell Biol.. 1976; 13 29-83
- 5 Wang Y, Hamburger M, Gueho J, Hostettmann K. Cyclohexanecarboxylic acid derivatives from Psiadia trinervia . Helv. Chim. Acta. 1992; 75 269-75
- 6 Deyama T, Ikawa T, Kitagawa S, Sansei N. The constituents of Eucommia ulmoids OLIV. V. Isolation of dihydroxydehydrodiconifferyl alcohol isomers and phenolic compounds. Chem. Pharm. Bull.. 1987; 35 1785-9
- 7 Fuchs C, Spiteller G. Rapid and easy identification of isomers of coumaroyl- and caffeoyl-D-quinic acid by gas chromatography/mass spectrometry. Journal of Mass Spectrometry. 1996; 31 602-8
- 8 Ida Y, Satoh Y, Ohtsuka M, Nagasao M, Shoji J. Phenolic constituents of Phellodenron amurense bark. Phytochemistry. 1994; 35 209-15
- 9 Chen M, Wu W W, Shen G Q, Luo S Q, Li H T. Chemical constituents of Lonicera macranthoides Hand.-Mazz Part V. Isolation and structures of macranthoin F and G. Acta Pharmaceutica Sinica. 1994; 29 617-20
- 10 Keppler D, Lesch R, Reutter W, Decker K. Experimental hepatitis induced by D-galactosamine. Exp. Mol. Pathol.. 1968; 9 279-90
- 11 Felver M E, Mezey E, Mcguire M, Mitchell M C, Herlong H F, Veech G A, Veech R L. Plasma tumor necrosis factor alpha predicts decreased long-term survival in severe alcoholic hepatitis. Alcoholism. Clin. Exp. Res.. 1990; 14 255-9
- 12 González-Amaro R, García-Monzón C, García-Buey L, Moreno-Otero R, Alonso J L, Yagüe E, Pivel J P, López-Cabrera M, Fernández-Ruiz E, Sánchez-Madrid F. Induction of tumor necrosis factor alpha production by human hepatocytes in chronic viral hepatitis. J. Exp. Med.. 1994; 179 841-8
- 13 Löhr H F, Schlaak J F, Gerken G, Fleischer B, Dienes H P, Büschenfelde K HM. Phenotypical analysis and cytokine release of liver-infiltrating and peripheral blood T lymphocytes from patients with chronic hepatitis of different etiology. Liver. 1994; 14 161-6
- 14 Bradham C A, Plümpe J, Manns M P, Brenner D A, Trautwein C. Mechanisms of hepatic toxicity. I. TNF-α induced liver injury. Am. J. Physiol.. 1998; 275 G387-92
- 15 Zhang H Q, Ding Y M, Chen G Y, Dong Y F, Zhu Y L. Active constituents of root of Euphorbia ebracteolata Hayata (Euphorbiaceae). Acta Botanica Sinica. 1987; 29 429-31
- 16 Cossarizza A, Mussini C, Mongirardo N, Borghi V, Sabbatini A, De Rienzo B, Franceschi C. Mitochondria alterations and dramatic tendency to undergo apoptosis in peripheral blood lymphocytes during acute HIV syndrome. AIDS. 1997; 11 19-26
- 17 Larrick J W, Wright S C. Cytotoxic mechanism of tumor necrosis factor α. FASEB. J.. 1990; 4 3215-23
- 18 O'donnell V B, Spycher S, Azzi A. Involvement of oxidants and oxidant generating enzyme(s) in tumor-necrosis-factor-α-mediated apoptosis: Role of lipoxygenase pathway but not mitochondrial respiratory chain. Biochem. J.. 1995; 310 133-41
- 19 Slater A FG, Nobel C SI, Orrenius S. The role of intracellular oxidants in apoptosis. Biochimica et Biophysica Acta. 1995; 1271 59-62
- 20 Kimura Y, Okuda H, Okuda K, Hatano T, Agata I, Arichi S. Studies on the activies of tannins and related compounds; V. Inhibitory effects on lipid peroxidation in mitochondria and microsomes of liver. Planta Medica. 1984; 50 473-7
Prof. Li-Jun Wu
Department of Natural Medicine
Shenyang Pharmaceutical University
103 Wenhua Road
Shenyang, 110015
People’s Republic of China
Email: xiangting2000@hotmail.com
Fax: +86-24-83890024