Korean Journal of Pharmacognosy (생약학회지)

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Phenolic Constituents from the Flowers of Synurus excelsus

큰수리취 꽃의 페놀성 성분

  • Lee, Il-Kyun (Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University) ;
  • Yang, Min-Cheol (Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University) ;
  • Lee, Kyu-Ha (Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University) ;
  • Choi, Sang-Un (Korea Research Institute of Chemical Technology) ;
  • Lee, Kang-Ro (Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University)
  • 이일균 (성균관대학교 약학대학 천연물 약품 화학 연구실) ;
  • 양민철 (성균관대학교 약학대학 천연물 약품 화학 연구실) ;
  • 이규하 (성균관대학교 약학대학 천연물 약품 화학 연구실) ;
  • 최상운 (한국화학연구소) ;
  • 이강노 (성균관대학교 약학대학 천연물 약품 화학 연구실)
  • Published : 2007.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

Seven phenolic compounds, scopoletin (1), caffeic acid methyl ester (2), apigenin 7-O-${\alpha}$-L-rhamnosyl-(1${\rightarrow}$6)-O-${\alpha}$-D-glucoside (3), isorhamnetin 7-O-${\alpha}$-D-glucoside (4), isorhamnetin 3-O-${\alpha}$-D-glucoside (5), luteolin (6), and quercetin 3-methyl ether (7) were isolated from the methanol extract of the flowers of S. excelsus. Their structures were established by chemical and spectroscopic methods. The isolated compounds were tested for their cytotoxicity against four human cancer cell lines in vitro using a SRB method. The compounds 4 and 7 showed moderate cytotoxicity with ED$_{50}$ values ranging from 1.59 to 13.14${\mu}$g/ml.

Keywords

References

  1. 이창복(2003) 원색대한식물도감, 294. 향문사, 서울
  2. 이우철(1996) 原色韓國基準植物圖鑑, 1207, 아카데미서적, 서울
  3. Ham, S. S., Han, H. S., Choi, K. P. and Oh, D. H.(1997) Inhibitory effect of synurus deltoides extracts on the mutagenesis induced by various mutagens. Korean J. Soc. Food., 26: 528-533
  4. Choi, Y. H., Son, K. H., Chag, H. W., Bae, K. H., Kang, S. S. and Kim, H. P.(2005) New anti-inflammatory formulation containing synurus deltoids extract. Arch. Pharm. Res., 28(7): 848-853 https://doi.org/10.1007/BF02977352
  5. Nam, J. H., Choi, S. Z. and Lee, K. R.(2004) Phytochemical constituents of Synurus excelsus. Kor. J. Pharmacogn., 35(2): 116-121
  6. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMabon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S. and Boyd, M. R.(1990) New colorimetric cytotoxicity assay for anticancer-drug screeninf. J. Nar'l. Cancer Inst., 82: 1107 https://doi.org/10.1093/jnci/82.13.1107
  7. Kwon, Y. S., Shin, S. J., Kim, M. J. and Kim, C. M.(2001) A new coumarin from stem of Angelica dahurica. Arch. Pharm. Res., 25(1): 53-56 https://doi.org/10.1007/BF02975261
  8. Kim, J. S, Kim, J. C., Shin, S. H., Lee, E. J., Jin, W. Y., Bae, K. W., Son, K. H., Kim, H. P., Kang, S. S. and Chang, H. W.(2006) Chemical cinstitucents of the root of Dystaenia takeshimana and their anti-inflammatory activity. Arch. Pharm. Res., 29(8): 617-623 https://doi.org/10.1007/BF02968244
  9. Sin, K. M., Kim, I. T., Park, Y. M., Ha, J. H., Choi, J. W., Park, H. J., Lee, Y. S. and Lee, K. T.(2004) Anti-inflammatory effect of caffeicacid methyl ester and its mode of action through the inhibition of prostagladin E2, nitric oxide and tumor necrosis factor-${\alpha}$ production. Biochem. Pharmacol., 68: 2327-2336 https://doi.org/10.1016/j.bcp.2004.08.002
  10. Saleem, M., Kim, H. J., Jin, C. B. and Lee, Y. S.(2004) Anti-oxidant caffeic acid derivatives from leaves of Parthenocissus tricuspidata. Arch. Pharm. Res., 27(3): 300-304 https://doi.org/10.1007/BF02980064
  11. Kim, N. M., Kim, J., Chung, H. Y. and Choi, J. S.(2000) Isolation of luteolin 7-O-rutinoside and esculetin with potential antioxide activity from the aerial parts of Artemisia montana. Arch. Pharn, Res., 23(3): 237-239 https://doi.org/10.1007/BF02976451
  12. Bennini, B., Chulia, A. J., Kaouadji, M. and Thomasson, F.(1992) Flavonoid glycosides from Erica cinerea. Phytochemistry, 31(7): 2483-2486 https://doi.org/10.1016/0031-9422(92)83305-I
  13. Wanjala, C. W. and Majinda, R. T.(1999) Flavonoid glycosides from Crotalaria podocarpa. Phytochemistry, 51: 705-707 https://doi.org/10.1016/S0031-9422(99)00065-5
  14. Nordby, H. E., Fisher, J. F. and Kew, T. J.(1968) Apigenin 7${\yen}{\hat{a}}$-glucoside, a new flavonoid from the leaves of Citrus Paradisi. Phytochemistry, 7: 1653-1657 https://doi.org/10.1016/S0031-9422(00)88619-7
  15. Wang, M., Simon, J. E., Aviles, I. F., He, K., Zheng, Q. Y. and Tadmor, Y.(2003) Analysis of actioxidative phenolic compounds in Artichoke (Cynara scolymus L.). J. Agric. Food Chem., 51: 601-608 https://doi.org/10.1021/jf020792b
  16. Kanchanaroom, T., Noiarsa, P., Ruchirawat, S., Kasai, R. and Otsuka, H.(2004) Phenylethanoid and iridoid glycosides from the thai medicinal plant, Barleria strigosa. Chem. Pharm. Bull., 52(5): 612-614 https://doi.org/10.1248/cpb.52.612
  17. Fan, C. Q. and Yue, J. M.(2003) Biologically active phenols from Saussurea medusa. Bioorgan. Med. Chem., 11: 703-708 https://doi.org/10.1016/S0968-0896(02)00470-4
  18. Nishida, R.(1994) Oviposition stimulant of a zeryntine swallowtail butterfly, Luehdorfia japonica. Phytochemistry, 36(4): 873-877 https://doi.org/10.1016/S0031-9422(00)90454-0
  19. Oh, H. M., Kwon, B. M., Baek, N. I., Kim, S. H., Chung, I. S., Park, M. H., Park, H. W., Lee, J. H., Park, H. W., Kim, E. J. and Kim, D. K.(2005) Inhibitory activity of isorhamnetin from Persicaria thunbergii on farnesyl protein transferase. Arch. Pharm. Res., 28(2): 169-171 https://doi.org/10.1007/BF02977709
  20. Xiong, Q., Shi, D. and Mizuno, Mizuo.(1995) Flavonol glucosides in pepicarps of Zanthoxylum bungeanum. Phytochemistry, 39(3): 723-725 https://doi.org/10.1016/0031-9422(94)00965-V
  21. Choi, J. S., Jung, M. J., Park, H. J., Chung, H. J. and Kang, S. S.(2002) Futher isolation of perxynitrite and 1,1-diphenyl-2-picrylhydrazyl radical scavenging isorhamnetin 7-O-glucoside from the leaves of Brassica juncea L. Arch. Pharm. Res., 25(5): 625-627 https://doi.org/10.1007/BF02976933
  22. D'agostino, M., Simone, F. De., Dini, A., Ramundo, E. and Zollo, F.(1990) Flavonoid glucosides from Eupatorium tiniforolium. Phytochemistry, 29(1): 353-354 https://doi.org/10.1016/0031-9422(90)89076-L
  23. Chae, S. W., Lee, S. H., Kang, S. S. and Lee, H. J.(2002) Flavonoid glucosides from the leaves of Helianthus tuberoses. Nat. Prod. Sci., 8(4): 141-143
  24. Sen, S., Sahu, N. P. and Mathato, S. B.(1992) Flavonol glycosides from Calotropis gigantea. Phytochemistry, 31(8): 2919-2921 https://doi.org/10.1016/0031-9422(92)83668-O
  25. Kang, S. S., Choi, J. S., Woo, W. S. and Chi, H. J.(1983) Isorhamnetin glycosides from the leaves of Typha latifolia. Kor. J. Pharmacog., 14(4): 137-139
  26. Kim, C. W., Choi, K. S.(1993) Studies on the constituents of Impatiens textori. Kor. J. Pharmacogn., 24(1): 26-31
  27. Kim, K. S., Lee, S. H., Kang, K. H. and Kim, B. K.(2005) Flavonoid galactosides from Artemisia apiacea. Nat. Prod. Sci., 11(1): 10-12
  28. Oscar, B., J. Alberto, M., Juan, F. S. and Juan, S. P.(1986) 3- Methoxyl flavones and coumarins from Artemisia incanescens. Phytochemistry, 25(10): 2357-2360 https://doi.org/10.1016/S0031-9422(00)81695-7
  29. Park, J. C., Park, J. G., Hur, J. S., Choi, M. R., Yoo, E. J., Kim, S. H., Son, J. C. and Kim, M. S.(2004) Inhibitory effects of methanol extract, phenolic acids and favonoids from the leaves of Eucalyptus darylmpleana against 1,1- diphenyl-2-picrylhydrazyl radical. Nat. Prod. Sci., 10(5): 244-247
  30. Huong, D. T. L., Dat, N. T., Cai, X. F. and Shen, G.(2004) Phenolic components from the leaves and twings of Rhamnus taquetii. Kor. J. Pharmacogn., 35(2): 139-142
  31. Lee, E. H, Kim, H. J., Song, Y. S., Jin, C. B., Lee, K. T., Cho, J. S. and Lee, Y. S.(2003) Constituents of the stems and fruits of Opuntia ficus-indica var.saboten. Arch. Pharm. Res., 26(12): 1018-1023 https://doi.org/10.1007/BF02994752