Phenolic Compounds from Seeds of Astragalus sinicus and Its Antioxidative Activities

자운영(Astragalus sinicus)종자의 페놀성 화합물 및 항산화 활성

  • Published : 2003.12.30

Abstract

Phytochemical examination of seeds of Astragalus sinicus has led to the isolation and characterization of kaempferol $3-O-{\beta}-D-apiofuranosyl-(1{\rightarrow}2)-{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}6)-{\beta}-D-glucopyranoside$ (1), quercetin $3-O-{\beta}-D-xylopyranosyl-(1{\rightarrow}2)-{\beta}-D-glucopyranoside$ (2), ampelopsin (3), ampelopsin $3'-O-{\beta}-D-xylopyranoside$ (4), ampelopsin $3'-O-{\beta}-Dxylopyranoside$ (5), myricetin (6), myricetin $3'-O-{\beta}-D-glucopyranoside$ (7), myricetin $3'-O-{\beta}-D-xylopyranoside$ (8). Antioxidative activity of these compounds was determined by measuring the radical scavenging effect on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Flavanonols(3,4, and 5) showed potent antioxidative activity.

Keywords

References

  1. Lee, Y.N. (1996) Flora of Korea, 410, Kyo-Hak Publishing Co., Seoul
  2. Kim, C.M, Shin, M.K, Ahn, D.K., and Lee, K.S. (1998) 中藥大辭典, 4630, Jung-Dam Publishing Co., Seoul
  3. Lee, W.C. (1996) Standard Illustrations of Korean Plants, 186, Academic Publishing Co., Seoul
  4. Tong, Wand Eisenbrand, G. (1992) Chinese Drugs of plant Origin, Springer Verlag, Berlin
  5. Erdal, B., Ihsan, C., Chuck, D., Rudraksh, S., John, K. B., and Ikhlas, A. K. (2001) Two novel cycloartane-type triter-pene glycosides from the roots of Astragalus prusianus, Tetrahedron 57: 5961-5966 https://doi.org/10.1016/S0040-4020(01)00607-X
  6. Erdal, B., Ihsan, C, Rita, A, Sonia, P., and Cosimo, P. (1999) Trojanoside H : A cycloartane-type glycoside from the aerial parts of Astragalus trojanus, Phytochemistry 51: 1017-1020 https://doi.org/10.1016/S0031-9422(99)00035-7
  7. Pierluigi, G., Francesca, P., Marco, T., Luisella, V., Nadia, E. S., Aya, M. A., Rokia, M. A, and Soas, M. T. (1995) Cycloratane triterpene glycosides from Astraglaus trigonus, Phytochemistry 40: 1755-1760 https://doi.org/10.1016/0031-9422(95)00544-H
  8. Lusia, P., Stefania, P., Guido, F., Aleessandra, B., and Antonio, M. (1997) Three cycloasrtagenol glucosides from Astragalus verrucosus, Phytochemistry 45: 585-587 https://doi.org/10.1016/S0031-9422(96)00862-X
  9. Luisa, P., Stefania, P., Alessandra, B., and Donatella, P.(1998) Cicloastragenol glycosides from Astragalus verrucosus, Phytochemistry 49: 2467-2471 https://doi.org/10.1016/S0031-9422(98)00297-0
  10. Nadia A.E., Aya, M.A., Rokia, M.A., Soad, M.T., and Fulvia, O. (2000) Constituents of Egyptian Astragalus tribuloides Del., Nat. Prod. Sci. 6: 11-15
  11. Luisa, P, Alessandra, B., Elena, L., Ivano, M., and Lirio, P. (2002) Antimicrobial and antifungal activity of crude extracts and isolated saponin from Astragalus verrucosus, Fitoteria 73: 336-339 https://doi.org/10.1016/S0367-326X(02)00087-4
  12. Ihsan, C., Hasan, Y., Oliver, Z., and Otto, S. (1999) Cepha-lotoside : A tridesmosidic cycloartane type glycoside from Astragalus cephalotes var. brevicalyx, Phytochemistry 50: 843-847 https://doi.org/10.1016/S0031-9422(98)00601-3
  13. Luisella, V., Marco, T., Nadia, A. E., and Soad, M. T. (1998) Cycloartane triterpene glycosides from Astragalus sieberi, Phytochemistry 48: 1403-1409 https://doi.org/10.1016/S0031-9422(98)00042-9
  14. Yu, Z., Masao, H., Hekai, R, and Tsutomu, F. (1995) Two triglycosidic triterpene astragalosides from hairy root culture of Astragalus membranaceus, Phytochemistry 38: 1407-1410 https://doi.org/10.1016/0031-9422(94)00833-F
  15. Baoliang C., Yusuke, S., Takashi, T., Junei, K, and Toshihiro N. (1992) Four new oleanene derivatives from the seeds of Astraglaus complanatus, Chem. Pharm. Bull. 40: 136-138 https://doi.org/10.1248/cpb.40.136
  16. Baoliang, C., Junko, I., Takashi, T., Junei, K, and Toshihiro, N. (1992) Triterpene glycosdies from the seeds of Astragalus sinicus L., Chem. Pharm. Bull. 40: 3330-3333 https://doi.org/10.1248/cpb.40.3330
  17. Kim, J. S., Park, J. S., Kim, C. S., and Kim, J. M. (2000) NMR assignments including HMBC and 1D-TOCSY data of astraloside, and isoastragaloside from from roots of Astragalus membranaceus, Kor. J. Pharmacogn 31: 34-38
  18. Kim, J. S., Kim, Y. T., and Kim, C. S. (1996) A study on the constituents from the roots of Astragalus membranaceus (I), Kor. J. Pharmacogn 27: 336-341
  19. Kim,J. S. and Kim, C. S. (2000) Astudy on the constituents from the roots of Astragalus membranaceus (Ill), Kor. J. Pharmacogn 31: 109-111
  20. Shoji, Y., Mareshige, K, and Hiroshi, K. (2000) Flavonoid glycosides and saponins from Astragalus shikokianus, Phytochemistry 53: 469-471 https://doi.org/10.1016/S0031-9422(99)00512-9
  21. Baoliang, C., Motoyuki, N., Junei, K, and Toshihiro, N. (1992) Structures of three new acylated flavonoid glycosides from Astragalus complanatus R. Br., Chem. Pharm. Bull. 40: 1943-1945 https://doi.org/10.1248/cpb.40.1943
  22. Xiaofeng, M., Pengfei, T., Ymgjie, C., Tianyou, Z., Yun, W, and Yoichiro, I. (2003) Preparative isolation and purification of two isoflavanones from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed counter-current chromatography, Journal of Chromatography A, 992: 193-197 https://doi.org/10.1016/S0021-9673(03)00315-7
  23. Baek, N. I., Kim, Y. S., Kung, J. S., and Park, K. H. (1996) Isolation of anti-hepatotoxic agent from the root of Astragalus membranaceus, Kor. J. Pharmacogn. 27: 111-116
  24. Kim, J. S. and Kim C. S. (1997) A study on the constituents from the roots of Astragalus membranaceus (II), Kor. J. Pharmacogn 28: 75-79
  25. McCracken, D.S., Schermiester, L.J., and Bhatti, W.H. (1970) Phytochemical and cytotoxic evaluation of sevral Astragalus species of north dakota, Lliydia 33: 19-24
  26. Abdallah, R.M., Harraz, F.M., and El Sebakhy, N.A. (1990) Astragalus trigonus DC: Cytotoxicity screeinig of its cycloartane diglucoside and macro and micromorphology of the leaf, stem and root. Alex. J. Pharm. Sci. 4: 192-196
  27. Abdallah, R.M., Ghazy, N.M, EI-Sebakhy, N.A., Pirillo, A, and Verotta, L. (1993) Astragalosides from Egyptian Astragalus spinosus Vahl. Pharmarie 48: 452-454
  28. Hatano, T., Edamatsu, R, Hiramatsu, M., Mori, A, Fujita, Y, Yasuhara, T., Yoshida, T., and Okuda, T. (1989) Effects of the interaction of tannins with coexisting substances. Effects of tannins and ralated polyphenols on superoxide anion radical, and on 1,1-diphenyl-2-picrylhydrazyl radical. Chem. Pharm. Bull. 37: 2016-2021 https://doi.org/10.1248/cpb.37.2016
  29. Yong-Long, L., Barbara N.T., Joseph, J.H., and Steven P.M. (1993) A flavonol triglycoside from Bassharis thesioides. Phytochemistry 33: 1549-1551 https://doi.org/10.1016/0031-9422(93)85134-D
  30. Simone. F.D.. Dini. A.. Pizza. C.. Satumino. P.. and Schettino. O. (1990) Two flavonol glycosides from Chenopodium quinoa, Phytochemistry 29: 1690-1692
  31. Rosemary, F.W. (1991) A flavonol triglycoside from Actinidia arguta var. giraldii., Phytochemisty 30: 2443-2444 https://doi.org/10.1016/0031-9422(91)83680-J
  32. Agrawal, P.K. (1989) CARBON-13 NMR of Flavonoids, elsevier