Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
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A Phenolic Glucoside Isolated from Prunus serrulata var. spontanea and its Peroxynitrite Scavenging Activity

  • Jung Hyun Ah (Faculty of Food Science and Biotechnology, Pukyong National University) ;
  • Chung Hae Young (College of Pharmacy, Pusan National University) ;
  • Kang Sam Sik (Natural Product Research Institute and College of Pharmacy, Seoul National University) ;
  • Hyun Sook Kyung (Faculty of Food Science and Biotechnology, Pukyong National University) ;
  • Kang Hye Sook (Faculty of Food Science and Biotechnology, Pukyong National University) ;
  • Choi Jae Sue (Faculty of Food Science and Biotechnology, Pukyong National University)
  • Published : 2005.10.01
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Abstract

A new phenolic glucoside (1), pursargentoside, was isolated from the leaves of Prunus serrulata var. spontanea, along with three other known compounds, orobol 7-O-glucoside (2), $1{\beta}$, $2{\alpha}$, $3{\alpha}$, 24-tetrahydroxy-urs-12-en-28-oic acid (3), and chlorogenic acid (4). The structure of pursargentoside (1) was identified by spectroscopic data analysis including 1D and 2D NMR spectroscopy, as 2-O-${\beta}$-(6'-benzoyl)-glucopyranosyl o-(Z)-coumaric acid. Compounds 1, 2, and 4 exhibited ONOO- scavenging activity, whereas compound 3 was determined to be virtually inactive.

Keywords

References

  1. Anhut, S., Zinsmeister, H. D., Mues, R., Barz, W., Machenbroch, K., Koster, J., and Markham, K. R., The first identification of isoflavones from a bryophyte. Phytochemistry, 23, 1073-1075 (1984) https://doi.org/10.1016/S0031-9422(00)82611-4
  2. Donovan, J. L., Meyer, A. S., and Waterhouse, A. L., Phenolic composition and antioxidant activity of prunes and prunes juice (Prunus domestica). J. Agric. Food Chem., 46, 1247-1252 (1998) https://doi.org/10.1021/jf970831x
  3. Good, P. F., Hsu, A., Werner, P., Perl, D. P., and Olanow, C. W., Protein nitration in Parkinson's disease. J. Neurapathol. Exp. Neurol., 57, 338-342 (1998) https://doi.org/10.1097/00005072-199804000-00006
  4. Jung, H. A., Chung, H. Y., Jung, J. H., and Choi, J. S., A new pentacyclic triterpenoid glycoside from Prunus serrulata var. spontanea. Chem. Pharm. Bull., 52, 157-159 (2004) https://doi.org/10.1248/cpb.52.157
  5. Jung, H. A., Kim, A. R., Chung, H. Y., and Choi, J. S., In vitro antioxidant activity of some selected Prunus species in Korea. Arch. Pharm. Res., 25, 865-872 (2002) https://doi.org/10.1007/BF02977006
  6. Kayano, S. I., Kikuzaki, H., Fukutsuka, N., Mitani, T., and Nakatani, N., Antioxidant activity or prune(Prunus domestica L.) constituents and a new synergist. J. Agric. Food Chem., 50, 3708-3712 (2002) https://doi.org/10.1021/jf0200164
  7. Kim, S. S., Lee, C. K., Kang, S. S., Jung, H. A., and Choi, J. S., Chlorogenic acid, an antioxidant principle from the aerial parts of Artemisia iwayomogi that acts on 1,1-diphenyl-2-picrylhydrazyl radical. Arch. Pharm. Res., 20, 148-154 (1997) https://doi.org/10.1007/BF02974002
  8. Kim, T. J., In Korean Resources Plants, Seoul National University Publisher, Seoul, Korea, Vol. II, p. 171 (1996)
  9. Kooy, N. W., Royall, J. A., Ischiropoulos, H., and Beckman, J. S., Peroxynitrite-mediated oxidation of dihydrorhodamine 123. Free Radic. Biol. Med., 16, 149-156 (1994) https://doi.org/10.1016/0891-5849(94)90138-4
  10. Kritikar, K. R. and Basu, B. D., In Indian Medicinal Plants, M/S Periodical Experts, New Delhi, Vol. II, p. 951 (1974)
  11. Lahlou, H. E., Hirai, N., Tsuda, M., anel Ohigashi, H., Triterpene phytoalexins from nectarine fruits. Phytochemistry, 52, 623-629 (1999) https://doi.org/10.1016/S0031-9422(99)00316-7
  12. Nakatani, N., Kayano, S. I., Kikuzaki, H., Sumino, K., Katagiri, K., and Mitani, T., Identification, quantitative determination, and antioxidative of chlorogenic acid isomers in prune (Prunes domestica L.). J. Agric. Food Chem., 48, 5512-5516 (2000) https://doi.org/10.1021/jf000422s
  13. Ronson, R. S., Nakamura, M., and \/inten-Johansen, J., The cardiovascular effects and irnplications of peroxynitrite. Cardiovasc. Res., 44, 47-59 (1999) https://doi.org/10.1016/S0008-6363(99)00184-4
  14. Sang, S., Lapsley, K., Jeong, W. S., Lachance, P. A., Ho, C. T., and Rosen, R. T., Antioxidative phenolic compounds isolated from almond skins (Prunus amygdalus Batsch). J. Agric. Food Chem., 50, 2459-2463 (2002) https://doi.org/10.1021/jf011533+
  15. Shimomura, H., Sashida, Y., and Adachi, T., Cyanogenic and phenylpropanoid glucosides from Prunus grayana. Phytochemistry, 26, 2363-2366 (1987b) https://doi.org/10.1016/S0031-9422(00)84720-2
  16. Shimomura, H., Sashida, Y., and Adachi, T., Phenolic glucosides from Prunus grayana. Phytochemistry, 26, 249-251 (1987a) https://doi.org/10.1016/S0031-9422(00)81521-6
  17. Shimomura, H., Sashida, Y., and Adachi, T., Phenylpropanoid glucose esters from Prunus buergeriana. Phytochemistry, 27, 641-644 (1988) https://doi.org/10.1016/0031-9422(88)83165-0
  18. Takaishi, K., Studies on the coumarine components in the leaves of cherry-tree. Yakugaku Zasshi, 88, 1467-1471 (1968)
  19. Wang, H., Nair, M. G., Strasburg, G. M., Booren, A. M., and Gray, H. I., Antioxidant polyphenols from tart cherries (Prunus cerasus). J. Agric. Food Chem., 47, 840-844 (1999a) https://doi.org/10.1021/jf980936f
  20. Wang, H., Nair, M. G., Strasburg, G. M., Booren, A. M., and Gray, H. I., Novel antioxidant compounds from tart cherries (Prunuscerasus). J. Nat. Prod., 62, 86-88 (1999b) https://doi.org/10.1021/np980268s