Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Phytochemical Constituents of Bistorta manshuriensis

  • Chang, Sang-Wook (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University) ;
  • Kim, Ki-Hyun (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University) ;
  • Lee, Il-Kyun (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University) ;
  • Choi, Sang-Un (Korea Research Institute of Chemical Technology) ;
  • Ryu, Shi-Yong (Korea Research Institute of Chemical Technology) ;
  • Lee, Kang-Ro (Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University)
  • Published : 2009.12.31
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Abstract

Phytochemical investigation of the MeOH extract of the aerial parts of Bistorta manshuriensis resulted in the isolation of two cerebrosides, two lactams, six phenolic compounds and seven flavonoids. Their chemical structures were characterized by spectroscopic methods to be pinelloside (1), soyacerebroside I (2), pterolactam (3), 5-hydroxypyrrolidine-2-one (4), vanillic acid (5), caffeic acid methyl ester (6), protocatechuic acid (7), caffeic acid (8), 3,5-di-O-caffeoyl quinic acid methyl ester (9), chlorogenic acid methyl ester (10), avicularin (11), afzelin (12), quercetin (13), isoorientin (14), quercetin 3-O-${\beta}$-D-glucoside (15), quercitrin (16), and luteolin (17). The isolated compounds (1 - 4, 7, 12, 14) were isolated for the first time from this plant source and the compounds 1 - 4, 9 and 10 were first reported from the genus Bistorta. Compound 17 exhibited moderate cytotoxicity and compound 6 exhibited weak cytotoxicity against four human cancer cell lines in vitro using an SRB bioassay.

Keywords

References

  1. Choi, S.Z., Choi, S.U., and Lee, K.R., Phytochemical constituents of the aerial parts from Solidago virga-aurea var. gigantea. Arch. Pharm. Res. 27, 164-168 (2004) https://doi.org/10.1007/BF02980100
  2. Harrison, L.J., Sia, G.L., Sim, K.Y., Tan, H.T.W., Connolly, J. D., Lavaud, C., and Massiot, G., A ferulic acid ester of sucrose and other constituents of Bhesa paniculata. Phytochemistry 38, 1497-1500 (1995) https://doi.org/10.1016/0031-9422(94)00314-J
  3. Hirotaka, S., Michio, K., Kazuyuki, M., Seiji, K., and Isao, K., Sphingolipids and glycerolipids. IV. Syntheses and ionophoretic activities of several analogues of soya-cerebroside II, a calcium ionophoretic sphingoglycolipid isolated from Soybean. Chem. Pharm. Bull. 41, 1534-1544 (1993)
  4. Ju, Y., Sacalis, J.N., and Still, C.C., Bioactive flavonoids from endophyteinfected blue grass (Poaampla). J. Agric. Food Chem. 46, 3785-3788 (1998) https://doi.org/10.1021/jf980189m
  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. Kim, G.B., Shin, K.S., Kim, C.M., and Kwon, Y.S., Flavonoids from the leaves of Rhododendron schlipenbachii. Kor. J. Pharmacogn. 37, 177-183 (2006)
  7. Kim, S.K., Kim, H.J., Choi, S.E., Park, K.H., Choi, H.K., and Lee, M.W., Anti-oxidative and inhibitory activities on nitric oxide (NO) and prostaglandin $E_2$ (COX-2) production of flavonoids from seeds of Prunus tomentosa Thunberg. Arch. Pharm. Res. 31, 424-428 (2008) https://doi.org/10.1007/s12272-001-1174-9
  8. Kuhnt, M., Probstle, A., Rimpler, H., Bauer, R. and Heinrich, M., Biological and pharmacological activities and further constituents of Hyptis verticillata. Planta Med., 61, 227-232 (1995) https://doi.org/10.1055/s-2006-958061
  9. Kwak, J.H., Kim, H.J., Lee, K.H., Kang, S.C., and Zee, O.P., Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina. Arch. Pharm. Res. 32, 207-213 (2009) https://doi.org/10.1007/s12272-009-1137-x
  10. Laurence, V., Catherine, L., Georges, M., Thierry, S., and Hamid, A.H., Cytotoxic polyisoprenes and glycosides of long-chain fatty alcohols from Dimocarpus fumatus. Phytochemistry 50, 63-69 (1999) https://doi.org/10.1016/S0031-9422(98)00483-X
  11. Lee, I.K., Yang, M.C., Lee, K.H., Choi, S.U., and Lee, K.R., Phenolic constituents from the flowers of Synurus excelsus. Kor. J. Pharmacogn. 38, 181-186 (2007)
  12. Lee, J.H., Ku, C.H., Baek, N.I., Kim, S.H., Park, H.W., and Kim, D.K., Phytochemical constituents from Diodia teres. Arch. Pharm. Res. 27, 40-43 (2004) https://doi.org/10.1007/BF02980043
  13. Lee, M.H., Son, Y.K., and Han, Y.N., Tissue factor inhibitory flavonoids from the fruits of Chaenomeles sinensis. Arch. Pharm. Res. 25, 842-850 (2002) https://doi.org/10.1007/BF02977002
  14. Lee, T.B., Coloured Flora of Korea, Hyang-Moon Publishing Co., Seoul, pp. 253, 2003
  15. Liu, X., Li, W., Sheng, K., Liu, J., and Chen, F., Studies on the chemical constituents of the n-BuOH extract of Polygonum bistorta. Shenyang Yaoke Daxue Xuebao 23,15-17 (2006)
  16. Manoharan, K.P., Benny, T.K.H., and Yang, D., Cycloartane type triterpenoids from the rhizomes of Polygonum bistorta. Phytochemistry 66, 2304-2308 (2005) https://doi.org/10.1016/j.phytochem.2005.07.008
  17. Markham, K.R., Ternai, B., Stanley, R., Geiger, H. and Mabry, T.J., Carbon-13 NMR Studies of Flavonoids-III. Tetrahedron 34, 1389-1397 (1978) https://doi.org/10.1016/0040-4020(78)88336-7
  18. Meena, H., Paul, F., and Cathy, C.L., A caffeoylcyclohexane-1-carboxylic acid derivative from Asimina triloba. Phytochemistry 49, 103-108 (1998) https://doi.org/10.1016/S0031-9422(97)00804-2
  19. Skehan, P., Storeng, R., Scudiero, D., Monks, A., Mcmahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., and Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 82, 1107-1112 (1990) https://doi.org/10.1093/jnci/82.13.1107
  20. Song, M.C., Yang, H.J., Jeong, T.S., Kim, K.T., and Baek, N.I., Heterocyclic compounds from Chrysanthemum coronarium L. and their inhibitory activity on hACAT-1, hACAT-2, and LDL-oxidation. Arch. Pharm. Res. 31, 573-578 (2008) https://doi.org/10.1007/s12272-001-1195-4
  21. Staubmann, R., Schubert-Zsilavecz, M., Hiermann, A., and Kartnig, T., A complex of 5-hydroxypyrrolidin-2-one and pyrimidine-2,4-dione isolated from Jatropha curcas. Phytochemistry 50, 337-338 (1999) https://doi.org/10.1016/S0031-9422(98)00531-7
  22. Stephen, J.P., Louise, N.J., and David, C.P., High-resolution $^1H$- and $^{13}C$NMR. Spectra of D-glucopyranose, 2-acetamido-2-deoxy-Dglucopyranose, and related compounds in aqueous media. Carbohydr. Res. 59, 19-34 (1977) https://doi.org/10.1016/S0008-6215(00)83289-9
  23. Sun, L.X., Fu, W.W., Ren, J., Xu, L., Bi, K.S., and Wang, M.W., Cytotoxic constituents from Solanum lyratum. Arch. Pharm. Res. 29, 135-139 (2006) https://doi.org/10.1007/BF02974274
  24. Voutquenne, L., Lavaud, C., Massiot, G., Senenet, T., and Hadi, H. A., Cytotoxic polyisoprenes and glycosides of long-chain fatty alcohols from Dimocarpus fumatus. Phytochemistry 50, 63-69 (1999) https://doi.org/10.1016/S0031-9422(98)00483-X