Identification of Antioxidative Substances in Allium fistulosum L. by GC-MS

GC-MS에 의한 대파의 항산화 물질 동정

  • Seo, Gee-Woo (Department of Food Science and Technology and Institute of Agricultural Science and Technology, Chonnam National University) ;
  • Cho, Jeong-Yong (Department of Food Science and Technology and Institute of Agricultural Science and Technology, Chonnam National University) ;
  • Kuk, Ju-Hee (Department of Food Science and Technology and Institute of Agricultural Science and Technology, Chonnam National University) ;
  • Wee, Ji-Hyang (Department of Food Science and Technology and Institute of Agricultural Science and Technology, Chonnam National University) ;
  • Moon, Jae-Hak (Department of Applied Biology and Chemistry, The Research Institute of Agricultural Resource Development, Konkuk University) ;
  • Kim, Sung-Ho (Jindo Agricultural Technology Center) ;
  • Park, Keun-Hyung (Department of Food Science and Technology and Institute of Agricultural Science and Technology, Chonnam National University)
  • 서지우 (전남대학교 식품공학과 및 농업과학기술연구소) ;
  • 조정용 (전남대학교 식품공학과 및 농업과학기술연구소) ;
  • 국주희 (전남대학교 식품공학과 및 농업과학기술연구소) ;
  • 위지향 (전남대학교 식품공학과 및 농업과학기술연구소) ;
  • 문제학 (건국대학교 응용생물화학과.농업자원개발연구소) ;
  • 김성호 (진도군 농업기술센터) ;
  • 박근형 (전남대학교 식품공학과 및 농업과학기술연구소)
  • Published : 2003.10.01

Abstract

The ethyl acetate-soluble acidic fraction of juice, hot water, and MeOH extract of Allium fistulosum L. showed DPPH radical-scavenging activity. Each fraction was purified through silica gel adsorption column chromatography, and the active substances in the juice and hot water extract were identified as succinic acid, fumaric acid, 4-hydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid, 4-hydroxycinnamic acid, and 4-hydroxy-3-methoxycinnamic acid. For the MeOH extract, 4-hydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid, 4-hydroxycinnamic acid, and 4-hydroxy-3-methoxycinnmic acid were identified as the active substances by GC-MS. The contents of these compounds were determined by GC analysis, and their anti-oxidative activities were measured using the DPPH radical-scavenging assay. The results obtained showed that 4-hydroxy-3-methoxycinnamic acid was the dominant antioxidant in Allium fistulosum L.

대파에 함유된 항산화 물질을 구명하고자 대파를 3가지 다른 방법으로 추출하여 대파 착즙액, 열수추출물, MeOH 추출물을 얻었다. 이들 추출물을 각각 용매분획하여 얻어진 EtOAc 가용 산성획분을 silica gel adsorption column chromatography로 정제하여 얻어진 활성획분을 GC-MS 분석하였다. 그 결과, 대파 착즙액과 열수추출물에서는 succinic acid ,fumaric acid, 4-hydroxybenzoic acid, 4-hydroxy-3-methoxy-benzoic acid, 4-hydroxycinnamic acid 그리고 4-hydroxy-3-methoxycinnamic acid의 6종 화합물이 동정되었으며, MeOH 추출물로부터는 4-hydroxybenzoic acid, 4-hydroxy-3-methoxy-benzoic acid, 4-hydroxycinnamic acid, 4-hydroxy-3-methoxy-cinnamic acid의 4종 화합물이 동정되었다. 동정된 이들 화합물을 대상으로 DPPH radical-scavenging 활성을 검정한 결과, 4-hydroxy-3-methoxycinnamic acid가 가장 강한 항산화 활성을 나타냈다. 또한 각각의 대파추출물에 함유된 항산화 물질의 함량을 GC에 의해 정량분석한 결과, 대파 착즙액과 열수추출물 및 MeOH 추출물 모두 강한 항산화 활성을 나타내는 4-hydroxy-3-methoxycinnamic acid가 가장 많이 함유되어 있었다.

Keywords

References

  1. Gutteridge, J.M.C. and Halliwell, B. Antioxidants in Nutrition, Health and Disease, pp. 1-39. Oxford University Press, UK (1994)
  2. Ames, B.N. Dietary carcinogens and anticarcinogens, oxygen radicals and degenerative disease. Science 221: 1256-1264 (1983) https://doi.org/10.1126/science.6351251
  3. Halliwell, B. and Gutteridge, J.M.C. Oxygen toxicity, oxygen radicals, transition metals and disease. Biochem. J. 219: 1-14 (1984) https://doi.org/10.1042/bj2190001
  4. Gordon, M.H. Dietary antioxidants in disease prevention. Nat. Prod. Rep. 13: 265-273 (1996) https://doi.org/10.1039/np9961300265
  5. Branen, A.L. Toxicological and biochemistry of butylated hydroxytoluene, butylated hydroxyanisole. J. Am. Oil Chem. Soc. 52: 59-63 (1975) https://doi.org/10.1007/BF02901825
  6. Omaye, S.T., Reddy, K.A. and Cross, C.E. Effect of butylated hydroxytolene and other antioxidants on mouse lung metabolism. J. Toxicol. Environ. Health 3: 829-836 (1997) https://doi.org/10.1080/15287397709529617
  7. Yen, G.C., Chen, H.Y. and Peng, H.H. Antioxidant and pro-oxidant effects of various tea extracts. J. Agric. Food Chem. 45: 30-34 (1997) https://doi.org/10.1021/jf9603994
  8. Chung, S.K., Osawa, T. and Kawakishi, S. Hydroxyl radical-scavenging effects of spices and scavengers from brown mustard (Brassica nigra). Biosci. Biotech. Biochem. 61: 118-123 (1997) https://doi.org/10.1271/bbb.61.118
  9. Lindley, M.G. The impact of food processing on antioxidants in vegetable oils, fruits and vegetables. Trends Food Sci. Technol. 9: 336-340 (1998) https://doi.org/10.1016/S0924-2244(98)00050-8
  10. Kuo, J.M., Yeh, D.B. and Pan, B.S. Rapid photometric assay evaluating antioxdative activity in edible plants material. J. Agric. Food Chem. 47: 3206-3209 (1999) https://doi.org/10.1021/jf981351o
  11. Yokozawa, T, Dong, E., Liu, Z.W. and Shimizu, M. Antioxidative activity of flavones and flavonols in vitro. Phytother. Res. 11: 446-449 (1997) https://doi.org/10.1002/(SICI)1099-1573(199709)11:6<446::AID-PTR128>3.0.CO;2-8
  12. Choi, C.W., Kim, S.C., Hwang, S.S., Choi, B.K., Ahn, H.J., Lee, M.Y., Park, S.H. and Kim, S.K. Antioxidant activity and free radical scavenging capacity between Korean medicinal plants and flavonoids by assay-guided comparison. Plant Sci. 163: 1161-1168 (2002) https://doi.org/10.1016/S0168-9452(02)00332-1
  13. Seo, D.C., Chung, S.M., Lee, J.Y., Kim, Y.S. and Chung, J.H. Effect of oriental onion (Allium fistulosum) on platelet aggregation. J. Food Hyg. Saf. 11: 273-276 (1996)
  14. Ching, L.S. and Moharned, S. Alpha-tocopherol content in 62 edible tropical plants. J. Agric. Food Chem. 49: 3101-3105 (2001) https://doi.org/10.1021/jf000891u
  15. Yoon, I., Cho, J.Y., Kuk, J.H., Wee, J.H., Jang, M.Y, Ahn, T.H. and Park, K.H. Identification and activity of antioxidative compounds from Rubus coreanum fruit. Korean J. Food Sci. Technol.34: 898-904 (2002)
  16. Kuk, J.H., Ma, S.J., Moon, J.H., Kim, K.Y, Choi, S.H. and Park, K.H. Antibacterial and antifungal activities of a naphthoquinone derivative isolated from the fruits of Catalpa ovata G. DON. J. Microbiol. Biotechnol. 12:858-863 (2002)
  17. Cho, J.Y., Kim, H.K., Ma, S.J., Moon, J.H. and Park, K.H. Isolation and identification of azelaic acid and 3,4-dihydroxybenzoic acid from buckwheat hull as antimicrobial substances. Food Sci. Biotechnol. 9: 313-316 (2000)
  18. Abe, N., Nemoto, A., Tsuchiya, Y., Hojo, H. and Hirota, A. Studies of the 1,1-dipheny1-2-picrylhydrazyl radical scavenging mechanism for a 2-pyrone compound. Biosci. Biotech. Biochem. 64: 306-333 (2000) https://doi.org/10.1271/bbb.64.306
  19. Takao, T., Kitatani, F., Watanabe, N., Yagi, A. and Sakata, K. A simple screening method for antioxidants and isolation of several antioxidants produced by marine bacteria from fish and shellfish. Biosci. Biotech. Biochem. 58: 1780-1783 (1994) https://doi.org/10.1271/bbb.58.1780
  20. Cho, J.Y, Moon, J.H., Seong, K.Y. and Park, K.H. Antimicrobial activity of 4-hydroxybenzoic acid and trans 4-hydroxycinnamic acid isolated and identified from rice hull. Biosci. Biotechnol. Biochem. 62:2273-2276 (1998) https://doi.org/10.1271/bbb.62.2273
  21. Wee, J.H. and Park, K.H. Isolation of 4-hydroxycinnamic acid, 3-methoxy-4-hydroxycinnaimic acid, and 3,4-dihydroxybenzoic acid with antioxidative and antimicrobial activity from peanut (Arachis hypogaea) shell. Food Sci. Biotechnol. 10: 551-556 (2001)
  22. Cho, J.Y, Moon, J.H. and Park, K.H. Isolation and identification of 3-methoxy-4-hydroxybenzoic acid and 3-methoxy-4-hydroxy- cinnamic acid from hot water extracts of Hovenia dulcis Thunb and confirmation of their antioxidative and antimicrobial activity. Korean J. Food Sci. Technol. 32: 1403-1408 (2000)
  23. Xing, Y.M. and White, P.J. Identification and function of antioxidants from oat groats and hulls. J. Am. Oil Chem. Soc. 74: 303-307 (1997) https://doi.org/10.1007/s11746-997-0141-x
  24. Maillard, N.M. and Berset, C. Evolution of antioxidant activity during kilning: role of insoluble bound phenolic acids of barley and malt. J. Agric. Food Chem. 43: 1789-1793 (1995) https://doi.org/10.1021/jf00055a008
  25. Castelluccio, C., Bolwell, G.P., Gerrish, C. and Rice-evans, C. Differential distribution of ferulic acid to major plasma constituents in relation to its potential as an antioxidant. Biochem. J. 316: 691-694 (1996) https://doi.org/10.1042/bj3160691
  26. Pokorny, J. Autooxidation of Unsaturated Lipids, pp. 141-206. Academic Press, New York, USA (1987)
  27. Natella, F., Nardini, M., Felice, M.D. and Scaccini, C. Benzoic and cinnamic acid derivatives as antioxidants: structure-activity relation. J. Agric. Food Chem. 47: 1453-1459 (1999) https://doi.org/10.1021/jf980737w