Korean Journal of Pharmacognosy (생약학회지)

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Phenolic Compounds from the Leaves of Nelumbo nucifera Showing DPPH Radical Scavenging Effect

연잎에서 DPPH 라디칼 소거활성을 가지는 페놀성 화합물의 분리

  • Park, Chan-Hum (Department of Oriental Medicine Resources and Research Institute of Korean Oriental Medicine, Sunchon National University) ;
  • Hur, Jong-Moon (Department of Oriental Medicine Resources and Research Institute of Korean Oriental Medicine, Sunchon National University) ;
  • Song, Kyong-Sik (Division of Applied Biology and Chemistry, College of Agriculture and Life Sciences, Kyungpook National University) ;
  • Park, Jong-Cheol (Department of Oriental Medicine Resources and Research Institute of Korean Oriental Medicine, Sunchon National University)
  • 박찬흠 (국립순천대학교 한약자원학과 및 한의약연구소) ;
  • 허종문 (국립순천대학교 한약자원학과 및 한의약연구소) ;
  • 송경식 (경북대학교 농업생명과학대학 응용생명과학부) ;
  • 박종철 (국립순천대학교 한약자원학과 및 한의약연구소)
  • Published : 2007.09.30
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Abstract

Nelumbo nucifera (Nymphaeaceae) has been widely used in a traditional oriental medicine to treat bleeding, fever, diarrhea, hemorrhoid, sunstroke, dysentery and dizziness. The leaves of this plant were refluxed with methanol, and then fractionated with organic solvents to screen the antioxidant activity using DPPH radical. Ethyl acetate and n-butanol fractions showed good DPPH radical scavenging effects and were carried out column chromatographies to isolate nine compounds. Their chemical structures were characterized as p-hydroxybenzoic acid (1), uracil (2), luteolin (3), quercetin $3-O-{\beta}-D-glucopyranoside$ (4), $rhamnetin 3-O-{\beta}-D-glucopyranoside$ (5), $isorhamnetin 3-O-{\beta}-D-glucopyranoside$ (6), $quercetin 3-O-{\beta}-D-glucuropyranoside$ (7), $quercetin 3-O-{\beta}β-D-xylofuranosyl(1{\rightarrow}2)-{\beta}-D-galactopyranoside$ (8), and adenine (9) by comparison NMR spectral data and with those in references. Compounds 1, 2, 5 and 9 were firstly isolated from this plant. Compounds 1, 3 and 4 showed potent DPPH radical scavenging activity. Especially, compound 3, luteolin showed the higher effect than ascorbic acid used as a positive control.

Keywords

References

  1. Slater, T. F. (1984) Free radical mechanisms in tissue injury. Biochem. J. 222: 1-15 https://doi.org/10.1042/bj2220001
  2. Halliwell B. and Gutteridge J. M. C. (1999) Free radicals in biology and medicine. 105-245. Oxford University Press, New York
  3. Valko, M., Leibfritz, D., Moncol, J., Cronin, M. T. D., Mazur, M. and Telser, J. (2007) Free radicals and antioxidants in normal physioilogical functions and human disease. Int. J. Biochem. Cell Biol., 39: 44-84 https://doi.org/10.1016/j.biocel.2006.07.001
  4. Arrigo, A. P. (1999) Gene expression and the thiol redox state. Free Radic. Biol. Med., 27: 936-944 https://doi.org/10.1016/S0891-5849(99)00175-6
  5. Chapple, I. L. C. (1997). Reactive oxygen species and antioxidants in inflammatory diseases. J. Clin. Periodontol., 24: 287-296 https://doi.org/10.1111/j.1600-051X.1997.tb00760.x
  6. Cadenas, E. and Davies, K. J. A. (2000) Mitochondrial free radical generation, oxidative stress, and aging. Free Radic. Biol. Med., 29: 222-230 https://doi.org/10.1016/S0891-5849(00)00317-8
  7. 이창복 (1993) 대한식물도감. 339-340. 향문사, 서울
  8. 김창민 (1998) 중약대사전. 4623-4624. 정담, 서울
  9. 정보섭 (1990) 도해 향약대사전(식물편). 514-517. 영림사, 서울
  10. 허준 (2004) 原本東醫寶鑑. 710. 南山堂, 서울
  11. Furukawa, H. (1966) On the alkaloids of Nelumbo nucifera Gaertn. . alkaloids of Loti Embryo. Yakugaku Zasshi, 86: 75- 77 https://doi.org/10.1248/yakushi1947.86.1_75
  12. Cho, E. J., Yokozawa, T., Rhyu, D. Y., Kim, S. C., Shibahara, N. and Park, J. C. (2003) Study on the inhibitory effects of Korean medicinal plants and their main compounds on the 1,1-diphenyl-2-picrylhydrazyl radical. Phytomedicine, 10: 544-551 https://doi.org/10.1078/094471103322331520
  13. Kashiwada, Y., Aoshima, A., Ikeshiro, Y., Chen, Y. P., Furukawa, H., Itoigawa, M., Fujioka, T., Mihashi, K., Cosentino, L. M., Morris-Natschke, S. L. and Lee K. H. (2005) Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera and structure–activity correlations with related alkaloids. Bioorg. Med. Chem., 13: 443-448 https://doi.org/10.1016/j.bmc.2004.10.020
  14. 이양숙 (2006) 싸리 추출물의 폴리페놀 함량과 생리활성. 한국식품저장유통학회지, 13: 612-622
  15. 김성빈, 노승배, 류동영, 김동욱 (2005) 고지혈증 및 동맥 경화 감응 Bio F1B 햄스터에서 연잎 (Nelumbo nucifera)의 지질저하 효과. 생약학회지, 36: 229-234
  16. Ono, Y., Hattori, E., Fukaya, Y., Imai, S. and Ohizumi, Y. (2006) Anti-obesity effect of Nelumbo nucifera leaves extract in mice and rats. J. Ethnopharmacol., 106: 238-244 https://doi.org/10.1016/j.jep.2005.12.036
  17. 고병섭, 전동화, 장진선, 김주호, 박선민 (2006) In vitro에 서 조릿대, 연근과 연잎이 인슐린 작용 및 분비에 미치는 영향. 한국식품과학회지, 38: 144-120
  18. 권오근, 김성환, 천병열, 박채규, 손건호 (1999) 목단피로부터 항균활성 성분의 분리. 생약학회지, 30: 340-344
  19. Lee, S. H., Kang, S. S. and Shin, K. H. (2002) Coumarins and a pyrimidine from Angelica gigas roots. Natural Product Sciences, 8: 58-61
  20. Loizzo, M. R., Said, A., Tundis, R., Rashed, K., Statti, G. A., Hufner, A. and Menichini, F. (2007) Inhibition of angiotensin converting enzyme (ACE) by flavonoids isolated from Ail-anthus excelsa (Roxb) (Simaroubaceae). Phytother. Res., 21:32-36 https://doi.org/10.1002/ptr.2008
  21. Kim, S. J., Cho, J. Y., Wee, J. H., Jang, M. Y., Kim, C., Rim, Y. S., Shin, S. C., Ma, S. J., Moon, J. H. and Park, K. H. (2005) Isolation and characterization of antioxidative compounds from the aerial parts of Angelica keiskei. Food Sci. Biotechnol., 14: 58-63
  22. Goda, Y., Kaore Hoshino, K., Ishikawa, T., ABE, Y., Nakamura, H., Otsuka, H., Takeda, Y., Tanimurq, A. and Toyoda, M. (1999) Constituents watercress: inhibitors of histamine release from RBL-2H3 cells induced by antigen stimulation. Bio. Pharm. Bull., 22: 1319-1326 https://doi.org/10.1248/bpb.22.1319
  23. Lim, S. S., Jung, Y. J., Hyun, S. K., Lee, Y. S. and Choi, J. S. (2006) Rat Lens aldose reductase inhibitory constituents of Nelumbo nucifera stamens. Phytother. Res., 20: 825-830 https://doi.org/10.1002/ptr.1847
  24. Miliauskas, G., Beek, T. A., Venskutonis, P. P., Linssen, J. P. H. and Sudhölter, E. J. R. (2004) Antioxidant activity of Potentilla fruticosa. J. Sci. Food Agric., 84: 1997-1999 https://doi.org/10.1002/jsfa.1914
  25. 허종문, 이종호, 최종원, 황기욱, 정신교, 김문성, 박종철 (1998) 서양고추냉이 추출물과 분리한 kaempferol 배당체들의 브로모벤젠 처리 흰쥐에서 in vitro 지질과산화억제 효과. 생약학회지, 29: 231-236
  26. Moriyama, H., Iizuka, T., Nagai, M. and Hoshi, K., (2003) Adenine, an inhibitor of platelet aggregation, from the leaves of Cassia alata. Biol. Pharm. Bull., 26: 1361-1364 https://doi.org/10.1248/bpb.26.1361
  27. Donnini, S., Finetti, F., Lusini, L., Morbidelli, L., Cheynier, V., Barron, D., Williamson, S., Waltenberger, J. and Ziche, M. (2006) Divergent effects of quercetin conjugates on angiogenesis. Br. J. Nutr., 95: 1016-1023 https://doi.org/10.1079/BJN20061753
  28. Moon, J. H., Tsushida, T., Nakahara, K. and Terao, J. (2001) Identification of quercetin 3-O-${\beta}$-D-glucuronide as an antioxidative metabolite in rat plasm after oral administration of quercetin. Free Radic. Biol. Med., 30: 1274-1285 https://doi.org/10.1016/S0891-5849(01)00522-6
  29. Akbay, P., Basaran, A. A., Undeger, U. and Basaran, N. (2003) In vitro immunomodulatory activity of flavonoid glycosides from Urtica dioica L. Phytother. Res., 17: 34-37 https://doi.org/10.1002/ptr.1068
  30. Ahmed, M. S., El Tanbouly, N. D., Islam, W. T., Sleem, A. A. and El Senousy, A. S. (2005) Antiinflammatory flavonoids from Opuntia dillenii (Ker-Gawl) Haw. flowers growing in Egypt. Phytother. Res., 19: 807-808 https://doi.org/10.1002/ptr.1708