Biological Activities of Flavonoid Glycosides Isolated from Angelica keiskei

신선초에서 분리된 flavonoid glycosides의 생리활성

  • Published : 2005.02.28

Abstract

Recently, much attention has been focused on plant antioxidants, because they are expected to protect against oxidative damage, possibly preserving biological functions of cells. Antioxidant compounds were isolated from Angelica keiskei through extraction with 80% EtOH, and fractionations were carried out sequentially with n-hexane, chloroform, ethyl acetate, n-butanol, and water. Two active compounds were isolated from ethyl acetate fraction by silica gel column chromatography, and were identified as isoquercitrin ($quercetin-3-O-{\beta}-D-glucose$) and hyperoside ($quercetin-3-O-{\beta}-D-glucose$). Isoquercitrin and hyperoside showed strong antioxidative potency, as revealed by evaluation of their ABTS, DPPH, OH, and $H_{2}O_{2}$ radical-scavenging activities, and ex vivo DNA damage-protecting effects.

Keywords

antioxidant activity;Angelica keiskei;isoquercitrin;hyperoside;DNA;damage protection

References

  1. Freeman BA, Grapo JD. Biology of disease: free radicals and tissue injury. Lab. Invest. 47: 412-426 (1982)
  2. Iagashi K, Takanashi K, Makino M, Yasui T. Antioxidative activity of major anthocyanin isolated from wild grapes. Nippon Shokukin Kogryo Gakkaishi 36: 852-860 (1989) https://doi.org/10.3136/nskkk1962.36.10_852
  3. Bang MH, Song JC, Lee, SY, Park NG, Baek NI. Isolation of antioxidant compound from Paeonia lactiflora root. J. Korean Soc. Agric. Chem. Biotechnol. 42: 170-175 (1999)
  4. Arnao MB, Cano A, Acosta M. The hydrophilic and lipophilic contribution to total antioxidant acitivty. Food Chem. 73: 239-244 (2001) https://doi.org/10.1016/S0308-8146(00)00324-1
  5. Kim HY, Moon BH, Lee HJ, Choi DH. Flavonol glycosides from the leaves of Eucommia ulmoides with glycation inhibitory activity. J. Ethnopharm. 93: 227-230 (2004) https://doi.org/10.1016/j.jep.2004.03.047
  6. Hu JJ, Kurland DD, Ma BL, Roush GC. The effects of hydrogen peroxide on DNA repair activities. Mutation Res. 336: 193-201 (1995) https://doi.org/10.1016/0921-8777(94)00054-A
  7. Kim JH, Kang BH, Jeong JM. Antioxidant, antimutagenic and chemopreventive activities of a phyto-extract mixture derived from various vegetables, fruits and oriental herbs. Food Sci. Biotechnol. 12: 631-638 (2003)
  8. Masaki H, Skaki S, Atsumi T, Sakurai H. Active oxygen scavenging activity of plant extracts. Bull. Pharm. Bull. 18: 162-166 (1995) https://doi.org/10.1248/bpb.18.162
  9. Park JC, Yu YB, Lee JH. Chemical components from the aerial parts of Angelica Keiskei. Korean. J. Pharmacogn. 27: 80-82 (1996)
  10. Chung SY, Kim HW, Yoon S. Analysis of antioxidant nutrients in green yellow vegetable juice. Korean J. Food Sci. Technol. 31: 880-886 (1999)
  11. Cohen AM, Aberdroth RE, Hochstein P. Inhibition of free radical-induced DNA damage by uric acid. FEBS. Lett. 174: 147-150 (1984) https://doi.org/10.1016/0014-5793(84)81094-7
  12. Ames BN, Shigenaga MK, Hagwn TM. Oxidants, antioxidants and the degenerative disease of aging. Proc. Natl. Acad. Sci. 90: 7915-7922 (1993)
  13. Yamane T, Naktani H, Kikuoka N, Matsumoto H, Iwata Y, Jitao K, Oya K, Tachahashi T. Inhibitory effects and toxicity of green tea polyphenols for gastrointestinal carcinogenesis. Cancer 77: 1662-1667 (1996)
  14. John ML, William SB, Gaoyao W, Song W, Scott D. Direct antioxidant properties of creatine. Biochem. Biophy. Res. Commun. 290: 47-52 (2002) https://doi.org/10.1006/bbrc.2001.6164
  15. Hanato T. Constituents of natural medicines with scavenging effects on active oxygen species-tannins and related polyphenols. Nat. Med. 49: 357-363 (1995)
  16. Kim JS, Kim HY, Park YK, Kim TS, Kang MH. The effects of green vegetable juice (Angelica Keiskei) supplementation on plasma lipids and antioxidant status in smokers. Korean J. Nutr. 36: 933-941 (2003)
  17. Jeon EJ, Kim JS, Park YK, Kim TS, Kang MH. Protective effect of yellow-green vegetable juices on DNA dagame in Chinese hamster lung cell using Comet assay. Korean J. Nutr. 36: 24-31 (2003)
  18. Bhat VB, Sridhar GR, Madyastha KM. Efficient scavenging of hydroxyl radicals and inhibition of lipid peroxidation by novel analogues of 1,3,7-trimethyluric acid. Life Sci. 70: 381-393 (2001) https://doi.org/10.1016/S0024-3205(01)01484-9
  19. Park JC, Hur JM, Park JG. Biological activities of Umbelliferae family plants and their bioactive flavonoids. Food Ind. Nutr. 7: 30-34 (2002)
  20. Pratt DE. Role of flavones and related compounds in retarding lipid-oxidative flavor changes in food. p. 1. In: Phenolic, Sulfur and Nnitrogen Compounds in Food Flavors. American Chemical Society, Washington, DC, USA (1976)
  21. Yang HS. Effects of green juices. Food Hyg. 6: 62-67 (1993)
  22. Welch RW, Turley E, Sweetman SF, Kennedy G, Collins AR, Dunne A, Livingstone MB, McKenna PG, McKelvey-Martin VJ, Strain JJ. Dietary antioxidant supplementation and DNA damage in smokers and nonsmokers. Nutr. Cancer 34: 167-172 (1999) https://doi.org/10.1207/S15327914NC3402_7
  23. Fang YZ, Yang S, Wu G. Free radical, antioxidant and nutrition. Nutrition 18: 872-879 (2002) https://doi.org/10.1016/S0899-9007(02)00916-4
  24. Chun SS, Park JC, Kim SH, Lee DY, Choi HM, Hwang EY. Changes in biologically active component of Angelica keiskei by cooking methods. J. Korean Soc. Food Sci. Nutr. 27: 121-125 (1998)
  25. Yen GC, Duh PD, Tsai HL. Antioxidant and pro-oxidant properties of ascorbic acid and gallic acid. Food Chem. 79: 307-313 (2002) https://doi.org/10.1016/S0308-8146(02)00145-0
  26. Markham KR, Temai B, Stanley R, Geiger K, Mabry TJ. Carbon 13 NMR study of flavonoids-III. Naturally occurring flavonoid glycosides and their acylated derivatives. Tetrahedron 34: 1389-1397 (1978) https://doi.org/10.1016/0040-4020(78)88336-7