Korean Journal of Pharmacognosy (생약학회지)

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Flavonoids from the Seeds of Zizyphus jujuba var. spinosa

산조인 (酸棗仁)의 Flavonoid성분

  • Lee, So-Young (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Lee, Joo-Young (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Kim, Ju-Sun (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Lee, Je-Hyun (Department of Korean Medicine, Dongguk University) ;
  • Kang, Sam-Sik (Natural Products Research Institute and College of Pharmacy, Seoul National University)
  • 이소영 (서울대학교 약학대학 천연물과학연구소) ;
  • 이주영 (서울대학교 약학대학 천연물과학연구소) ;
  • 김주선 (서울대학교 약학대학 천연물과학연구소) ;
  • 이제현 (동국대학교 한의과대학) ;
  • 강삼식 (서울대학교 약학대학 천연물과학연구소)
  • Received : 2012.04.27
  • Accepted : 2012.06.09
  • Published : 2012.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

Eight flavonoids were isolated from the BuOH fraction of the 70% EtOH extract of Zizyphus jujuba var. spinosa seeds along with three known compounds, daucosterol (1), butyl ${\beta}$-D-fructofuranoside (2), and magnoflorine (4). On the basis of spectroscopic methods and comparison with literature values their structures were elucidated as 6"'-feruloylspinosin (3), nicotiflorin (5), 6"'-p-coumaroylspinosin (6), isospinosin (7), 6"'-vanilloylspinosin (8), spinosin (9), hovetrichoside C (10), and camelliaside B (11). Compounds 1, 2, 10, and 11 were isolated from this plant for the first time.

Keywords

Acknowledgement

Grant : 한약재 생리활성성분 분리 및 효능연구(6) - 산조인

Supported by : 식품의약품안전청

References

  1. Bae, K.-H. (2000) Medicinal Plants of Korea, 325, Kyo-Hak Publishing Co., Ltd., Seoul.
  2. Tang, W. and Eisenbrand, G. (1992) Chinese Drugs of Plant Origin, 1017-1024, Springer-Verlag, Berlin.
  3. Woo, W. S. (1996) Phytochemical researches in Korea. In Natural Products Research Institute (ed.), Natural Products Research in Korea. -A half century of academic achievements-, 11-50, Seoul National University Press, Seoul.
  4. Woo, W. S., Kang, S. S., Shim, S. H., Wagner, H., Chari, V. M., Seligmann, O. and Obermeiner, G. (1979) The structure of spinosin (2"-O-${\beta$-glucosylswertisin) from Zizyphus vulgaris var. spinosus. Phytochemistry 18: 353-355. https://doi.org/10.1016/0031-9422(79)80103-X
  5. Woo, W. S., Kang, S. S., Wagner, H., Seligmann, O. and Chari, V. M. (1980) Acylated flavone-C-glycosides from the seeds of Zizyphus jujuba. Phytochemistry 19: 2791-2793. https://doi.org/10.1016/S0031-9422(00)83976-X
  6. Han, B. H., Park, M. H. and Park, J. H. (1985) Studies on the sedative alkaloids from Zizyphus spinosus semen. Kor. J. Pharmacogn. 16: 233-238.
  7. Han, B. H. and Park, M. H. (1987) Alkaloids are the sedative principles of the seeds of Zizyphus vulgaris var. spinosus. Arch. Pharm. Res. 10: 203-207. https://doi.org/10.1007/BF02857740
  8. Shin, K. H., Lee, C. K., Woo, W. S. and Kang, S. S. (1978) Sedative action of spinosin. Arch. Pharm. Res. 1: 7-11. https://doi.org/10.1007/BF02856299
  9. Han, B. H., Park, M. H. and Park, J. H. (1989) Chemical and pharmacological studies on sedative cyclopeptide alkaloids in some Rhamnaceae plants. Pure & Appl. Chem. 61: 443-448. https://doi.org/10.1351/pac198961030443
  10. Zhang, C.-Z., Xu, X.-Z. and Li, C. (1996) Fructosides from Cynomorium songaricum. Phytochemistry 41: 975-976. https://doi.org/10.1016/0031-9422(95)00705-9
  11. Zhang, Z., Wang, D., Zhao, Y., Gao, H., Hu, Y.-H. and Hu, J.-F. (2009) Fructose-derived carbohydrates from Alisma orientalis. Nat. Prod. Res. 23: 1013-1020. https://doi.org/10.1080/14786410802391120
  12. Cheng, G., Bai, Y.-J., Zhao, Y.-J., Tao, J., Liu, Y., Tu, G.-Z., Ma, L.-B., Liao, N. and Xu, X.-J. (2000) Flavonoids from Zizyphus jujuba Mill var. spinosa. Tetrahedron 56: 8915- 8920. https://doi.org/10.1016/S0040-4020(00)00842-5
  13. Barbosa-Filho, J. M., Da-Cunha, E. V. L., Cornelio, M. L., Da Silva Dias, C. and Gray, A. I. (1997) Cissaglaberrimine, an aporphine alkaloid from Cissampelos glaberrima. Phytochemistry 44: 959-961. https://doi.org/10.1016/S0031-9422(96)00689-9
  14. Seo, H. K., Kim, J. S. and Kang, S. S. (2010) Labdane diterpenes and flavonoids from Leonurus japonicus. Helv. Chim. Acta 93: 2045-2051. https://doi.org/10.1002/hlca.201000043
  15. Tanaka, Y. and Sanada, S. (1991) Studies on the constituents of Zizyphus jujuba Miller. Shoyakugaku Zasshi 45: 148-152.
  16. Wu, Y., He, F., Pan, Q., Shi, Y., Min, Z. and Liang, J. (2011) C-Glucosyl flavones from the seeds of Zizyphus jujuba var. spinosa. Chem. Nat. Comp. 47: 369-372. https://doi.org/10.1007/s10600-011-9936-y
  17. Lewis, K. C., Maxwell, A. R., McLean, S., Reynolds, W. F. and Enriquez, R. G. (2000) Room-temperature ($^1H$, $^{13}C$) and variable-temperature ($^1H$) NMR studies on spinosin. Magn. Reson. Chem. 38: 771-774. https://doi.org/10.1002/1097-458X(200009)38:9<771::AID-MRC729>3.0.CO;2-4
  18. Yoshikawa, K., Eiko, K., Mimura, N., Kondo, Y. and Arihara, S. (1998) Hovetrichosides C-G, five new glycosides of two auronols, two neolignans, and a phenylpropanoid from the bark of Hovenia trichocarea. J. Nat. Prod. 61: 786-790. https://doi.org/10.1021/np9800396
  19. Shin, K. H., Kim, H. Y. and Woo, W. S. (1982) Determination of flavonoids in seeds of Zizyphus vulgaris var. spinosus by high performance liquid chromatography. Planta Med. 44: 94-96. https://doi.org/10.1055/s-2007-971410
  20. Zucolotto, S. M., Goulart, S., Montanher, A. B., Reginatto, F. H., Schenkel, E. P. and Frde, T. S. (2009) Bioassay-guided isolation of anti-inflammatory C-glucosylflavones from Passiflora edulis. Planta Med. 75: 1221-1226. https://doi.org/10.1055/s-0029-1185536
  21. Sena, L. M., Zucolotto, S. M., Reginatto, F. H., Schenkel, E. P., and De Lima, T. C. M. (2009) Neuropharmacological activity of the pericarp of Passiflora edulis flavicarpa Degener: Putative involvement of C-glycosylflavonoids. Exp. Biol. Med. 234: 967-975. https://doi.org/10.3181/0902-RM-84
  22. Dos Santos, R. I., Dos Santos, M. A. and Schenkel, E. P. (1996) Analysis of the plant drug Wilbrandia ebracteata (COGN.) COGN. Int. J. Pharmacog. 34: 300-302. https://doi.org/10.1076/phbi.34.4.300.13233
  23. Aqila, S., Giner, R. M., Recio, M. C., Spegazzini, E. D. and Rios, J. L. (2009) Anti-inflammatory activity of flavonoids from Cayaponia tayuya roots. J. Ethnopharmacol. 121: 333-337 https://doi.org/10.1016/j.jep.2008.11.002
  24. Bauer, R., Berganza, L. H., Seligmann, O. and Wagner, H. (1985) Cucurbitacins and flavone C-glycosides from Cataponia tayuya. Phytochemistry 24: 1587-1591.
  25. Kaewkrud, W., Otsuka, H., Ruchirawat, S. and Kanchanapoom, T. (2008) Megastigmane and flavone glycosides from Strophioblachia fimbricalyx Boerl. J. Nat. Med. 62: 124-125.
  26. Zeng, L., Zhang, R.-Y. and Wang, X. (1987) Studies on the constituents of Zizyphus spinosus Hu. Acta Pharm. Sin. 22: 114-120.
  27. Xie, Y.-Y., Xu, Z.-L., Wang, H., Kano, Y. and Yuan, D. (2011) A novel spinosin derivative from Semen Zizyphi Spinosae. J. Asian Nat. Prod. Res. 13: 1151-1157. https://doi.org/10.1080/10286020.2011.623128
  28. Zhang, L., Xu, Z.-L., Wu, C.-F., Yang, J.-Y., Kano, Y. and Yuan, D. (2012) Two new flavonoid glycosides from Semen Zizyphi Spinosae. J. Asian Nat. Prod. Res. 14: 121-128. https://doi.org/10.1080/10286020.2011.637491
  29. Fang, R., Veitch, N. C., Kite, G. C., Howes, M.-J. R., Porter, E. A. and Simmonds, M. S. J. (2011) Glycosylated constituents of Iris fulva and Iris brevicaulis. Chem. Pharm. Bull. 59: 124-128. https://doi.org/10.1248/cpb.59.124
  30. Liu, Q.-X., Wang, B., Liang, H., Zhao, Y.-Y. and Liu, M.-J. (2004) Structure identification of jujuboside D. Acta Pharm. Sin. 39: 601-604.
  31. Lee, S.-S., Wang, J.-S. and Chen, K. C.-S. (1995) Chemical constituents from the roots of Zizyphus jujuba Mill. var. spinosa (1). J. Chin. Chem. Soc. 42: 77-82. https://doi.org/10.1002/jccs.199500013
  32. Lee, S.-S., Tsai, F.-Y. and Chen, I.-S. (1995) Chemical constituents from Berchemia formosana. J. Chin. Chem. Soc. 42: 101-105. https://doi.org/10.1002/jccs.199500018
  33. Li, X-C., Cai, L. and Wu, C. D. (1997) Antimicrobial compounds from Ceanothus americanus against oral pathogens. Phytochemistry 46: 97-102. https://doi.org/10.1016/S0031-9422(97)00222-7
  34. Thuy, T. T., Kamperdick, C., Ninh, P. T., Lien, T. P., Thao, T. T. P. and Sung, T. V. (2004) Immnunosuppressive auronol glycosides from Artocarpus tokinensis. Pharmazie 59: 297-300
  35. Janes, N. F., King, F. E. and Morgan, J. W. W. (1963) The chemistry of extractives from hardwoods. Part XXXV. The constitution of maesopsin (2-benzyl-2,4,6,4'-tetrahydroxycoumaranone) and of its alkali fusion products. J. Chem. Soc. 1356-1363.
  36. Bekker, R., Li, X.-C., ElSohly, H. N., Clark, A. M., Brandt, E. V. and Ferreira, D. (2001) Resolution and absolute configuration of naturally occurring auronols. J. Nat. Prod. 64: 345-347. https://doi.org/10.1021/np000463i
  37. Elsinghorst, P. W., Cavlar, T., Muller, A., Braune, A., Blaut, M. and G tschow, M. (2011) The thermal and enzymatic taxifolin- alphitonin rearrangement. J. Nat. Prod. 74: 2243-2249. https://doi.org/10.1021/np200639s