Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
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Antioxidant Caffeic acid Derivatives from Leaves of Parthenocissus tricuspidata

  • Saleem, Muhammad (Medicinal Chemistry Research Center, Division of Life Sciences, Korea Institute of Science and Technology) ;
  • Kim, Hyoung-Ja (Medicinal Chemistry Research Center, Division of Life Sciences, Korea Institute of Science and Technolog) ;
  • Jin, Changbae (Medicinal Chemistry Research Center, Division of Life Sciences, Korea Institute of Science and Technolog) ;
  • Lee, Yong-Sup (Medicinal Chemistry Research Center, Division of Life Sciences, Korea Institute of Science and Technology)
  • Published : 2004.03.01
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Abstract

Five caffeic acid derivatives; methyl ester of caffeoylglycolic acid (1), dimethyl ester of caffeoyltartaric acid (2), dimethyl ester of caffeoyltartronic acid (3), monomethyl ester of caffeoyltartronic acid (4), methyl ester of caffeic acid (5), and some other secondary metabolites including; quercetin, quercetin 3-O-$\beta$-D-glucuronide methyl ester, kaempferol, 3,5,7,4'-O-tetramethylkaempferol, $\beta$-sitosterol glucoside, 2$\alpha$-hydroxyursolic acid and 2,24-dihydroxyursolic acid, have been isolated and characterized. All the isolated compounds were characterized with the help of NMR spectroscopy and mass spectrometry. Structure of compound 3 was also confirmed by a single X-ray crystallographic technique. Isolates were evaluated for anti-oxidant activities and most of the tested compounds were found to be potent in DPPH free radical scavenging ($IC_{50}{\;}={\;}4.56-14.17{\;}{\mu\textrm{g}}/mL$) and superoxide anion scavenging ($IC_{50}{\;}={\;}0.58-7.39{\;}{\mu\textrm{g}}/mL$) assays.

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References

  1. Baldi, A., Romani, A., Mulinacci, N., and Vincier, F. F., Polyphenols in Tuscan varieties of Vitis vinifera L. Jounrnal International des Sceinces de la Vigne ef du Vin, 27, 201-215 (1993)
  2. Budzianowski, J., Coumarins, caffeoyltartaric acids and the artifactual methyl esters from Taraxacum officinale leaves. Planta Medica, 63, 288-289 (1997) https://doi.org/10.1055/s-2006-957681
  3. Gamez, E. J. C., Luyengi, L., Lee,S. K., Zhu, L.-F., Zhou, B.-N., Fong, H. H. S., Pezzuto, J. M., and Kinghorn, A D., Antioxidant flavonoid glycosides from Daphniphyl/um calycinum. J. Nat. Prod., 61, 706-708 (1998) https://doi.org/10.1021/np9800203
  4. Hwang, H. K., Sung, H. K.,Wang, W. K. and Kim, I. H., Flavonol glycosides from Parthenocissus tricuspidata. Yakhak Hoechi, 39 (3), 289-296 (1995)
  5. Kolodynska, Z. and Wieniawski, W, Preparation of caffeoylglycolic acids. Acta Poloniae Pharmaceutica, 24, 261-265 (1967)
  6. Luo, W., Ang, Y. W. C., Gehring, A. T., Theresa, A., Heinze, M. T., Lin, J. L., and Matia, A., Determination of phenolic com-pounds in dietary supplements and tea blends containing Echinacea by liquid chromatography with coulometric electrochemical detection. J. AOAC Interl., 86, 202-208 (2003)
  7. Motoyuki, T. and Yasuyuki, O., A new antioxidative 1,3-benzodioxol from Melissa officinalis. Planta Medica, 64, 555-558 (1998) https://doi.org/10.1055/s-2006-957513
  8. Paulino, L. A., Dare, J. M., Maia, B., and Carlos, R. L., A re-sveratrol dimer from Parthenocissus tricuspidata. Phyto-chemistry, 30, 3144-3146 (1991)
  9. Sheldrick, G. M. SHELXS-90: A Program for Structure Determination, University of$G{\"{o}}ttingen$, $G{\"{o}}ttingen$, Germany(1997)
  10. Sheldrick, G. M. SHELXL-97: A Program for Structure Refinement, University of $G{\"{o}}ttingen$, $G{\"{o}}ttingen$, Germany (1997)
  11. Shisuo,T., Michio, K., and Moto, O., Effects of phenolcarboxylic acids on superoxide anion and lipid peroxidation induced by superoxide anion. Planta Medica, 57, 8-10 (1991) https://doi.org/10.1055/s-2006-960005
  12. Snook, E. M., Blum, S. M., Whitman, W. D., Arrendale, F. R., Costello, E. C., and Harwood, J. S., Caffeoyltartronic acid from catnip (Nepeta cataria): A precursor for catechol in lubber grasshopper (Romalea guttata) defensive secretions. J. Chem. Ecol., 19, 1957-1966 (1993) https://doi.org/10.1007/BF00983799
  13. Sumaryono, W., Wahono, P., Proksch, P., Wray, V., Witte, I., and Hartmann, T., Qualitative and quantitative analysis of the phenolic constituents from Ortosiphon aristatus. Planta Medica, 57, 176-180 (1991) https://doi.org/10.1055/s-2006-960060
  14. Toshiyki, T., Masayoshi, O., Kuniyasu, M., Fujio, A., and Munekazu, I., A resveratrol dimer from Parthenocissus tricuspidata. Phytochemistry, 48, 1241-1243 (1998) https://doi.org/10.1016/S0031-9422(97)00898-4
  15. Veit, M., Bauer, K., Beckert, C., Kast, B., Geiger, H., and Czygan, F. C., Phenolic characters of British hybrid taxa in Equisetum subgenus Equisetum. Biochemi. Sys. Ecol., 23, 79-87 (1995) https://doi.org/10.1016/0305-1978(95)93661-L
  16. Wang, Y. H., Zang, C. G. Yao, R. R., and Zohn, W. S., Studies on chemical constituents of Parthenocissus tricuspidata (Sieb et Zncc) Planch. Yao Yue Xue Bao, 17, 446 (1982)