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Isolation and Identification of Antioxidative Compounds 3,4-Dihydroxybenzoic acid from Black Onion

흑양파로부터 항산화 활성 물질인 3,4-Dihydroxybenzoic acid의 분리 및 동정

  • Yang, Ya-Ru (Department of Food Engineering and Food Industrial Technology Research Center, Mokpo National University) ;
  • Cho, Jeong-Yong (Department of Food Engineering and Salt Biotechnology Research Center, Mokpo National University) ;
  • Park, Yang-Kyun (Department of Food Engineering and Food Industrial Technology Research Center, Mokpo National University)
  • 양아여 (목포대학교 식품공학과 및 식품산업지역혁신센터) ;
  • 조정용 (목포대학교 식품공학과 및 천일염생명과학연구소) ;
  • 박양균 (목포대학교 식품공학과 및 식품산업지역혁신센터)
  • Received : 2011.10.17
  • Accepted : 2012.03.02
  • Published : 2012.04.30

Abstract

The antioxidant substance in black onion was identified. The assays that used 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzthiazo line-6-sulphonic acid) ($ABTS^+$) radicals showed that the ethyl acetate fraction of black onion methanol extract had a higher level of radical-scavenging activity than the other fractions. Two antioxidative compounds were purified and isolated from the ethyl acetate fraction via column chromatographies of silica gel and Sephadex LH-20 using the guided DPPH radical-scavenging assay. The isolated compounds were identified as 3,4-dihydroxybenzoic acid (1) and quercetin (2) based on mass spectrometry and nuclear magnetic resonance. The isolated compounds showed a high level of DPPH and ABTS+ radical-scavenging activity. Compound 2 had a higher level of radical-scavenging activity than 1.

양파의 매운 맛과 냄새를 감소시켜 섭취가 용이하도록 제조된 흑양파가 항산화 활성이 있다고 보고되어있어서 흑양파로부터 항산화 활성물질을 구명하고자 하였다. 흑양파 MeOH 추출물을 용매분획하여 얻어진 분획물들 중 EtOAc층이 높은 DPPH와 $ABTS^+$ radical scavenging 활성이 있었다. 그래서 EtOAc층을 silica gel과 Sephadex LH-20 등의 column chromatography를 이용하여 2종의 항산화 활성물질을 분리하였다. 단리한 이들 화합물을 대상으로 ESI-MS 및 NMR 분석을 통하여 3,4-dihydroxybenzoic acid (1)와 quercetin (2)로 각각 동정하였다. 이 화합물들은 $ABTS^+$ 및 DPPH radical scavenging 활성이 있었으며, 화합물 2는 화합물 1에 비해 더 높은 radical scavenging 활성이 있었다.

Keywords

References

  1. Kim JK, Seo Y, Noh SK, Cha YJ (2010) A concentrated onion extract lowers serum lipid levels in rats fed a high-fat diet. Korean J Food Preserv, 17, 398-404
  2. Kim SJ, Kim GH (2006) Quantification of quercetin indifferent parts of onion and its DPPH radical scavenging and antibacterial activity. Food Sci Biotechnol, 15, 39-43
  3. Xiao H, Parkin KL (2007) Isolation and identification of potential cancer chemopreventive agents from methanolic extracts of green onion (Allium cepa). Phytochemistry, 68, 1059-1067 https://doi.org/10.1016/j.phytochem.2007.01.021
  4. Yang YR, Park YK (2011) Black onions manufactured via the browning reaction and antioxidant effects of their water extracts. Korean J Food Preserv, 18, 310-318 https://doi.org/10.11002/kjfp.2011.18.3.310
  5. Yang YR, Park YK (2011) Comparison of antioxidant activities of black onion extracts. Korean J Food Preserv, 18, 954-960 https://doi.org/10.11002/kjfp.2011.18.6.954
  6. Yamaguchi N, Koyama Y (1967) Studies on the browning reaction products yields by reducing sugars and amino acid. Japan J Food Sci Technol, 14, 110-113 https://doi.org/10.3136/nskkk1962.14.110
  7. Lee JW, Do JH (2006) Current studies on browning reaction products and acidic polysaccharide in korean red ginseng. J Ginseng Res, 1, 41-48 https://doi.org/10.5142/JGR.2006.30.1.041
  8. Lee SJ, Shin JH, Kang MJ, Jung WJ, Ryu JH, Kim RJ, Sung NJ (2010) Antioxidants activity of aged red garlic. J Life Sci, 20, 775-781 https://doi.org/10.5352/JLS.2010.20.5.775
  9. Lee JW, Park CK, Do JH (2005) Antioxidative activity of the water soluble browning reaction products from korean red ginseng. J Ginseng Res, 1, 44-48 https://doi.org/10.5142/JGR.2005.29.1.044
  10. Shin JH, Kang MJ, Kim RJ, Ryu JH, Kim MJ, Lee SJ, Sung NJ (2011) Biological activity of browning compounds from processed garlics separated by dialysis membrane. J Korean Soc Food Sci Nutr, 40, 357-365 https://doi.org/10.3746/jkfn.2011.40.3.357
  11. Chung DM, Kwon SH, Chung YC, Chun HK (2011) Quercetin glucoside profiling of fresh onion (Allium cepa) and aged black onion using HPLC-ESI/MS/MS. J Life Sci, 3, 464-467 https://doi.org/10.5352/JLS.2011.21.3.464
  12. Gutfinger T (1981) Polyphenols in olive oils. J Am Oil Chem Soc, 58, 966-968 https://doi.org/10.1007/BF02659771
  13. Moreno MIN, Isla MI, Sampietro AR, Vattuone MA (2000) Comparison of the free radical scavenging activity of propolis from several region of Argentina. J Ethnopharmacol, 71, 109-114 https://doi.org/10.1016/S0378-8741(99)00189-0
  14. Choi Y, Kim MH, Shin JJ, Park JM, Lee J (2003) The antioxidant activities of the some commercial teas. J Korean Soc Food Sci Nutr, 32, 723-727 https://doi.org/10.3746/jkfn.2003.32.5.723
  15. Dewanto V, Xianzhong W, Liu RH (2002) Processed sweet corn has higher antioxidant activity. J Agric Food Chem, 50, 4959-4964 https://doi.org/10.1021/jf0255937
  16. Mukhtar H, Ahmad N (2000) Tea polyphenol: prevention of cancer and optimizing health. Am J Clin Nutr, 71, 1698-170 https://doi.org/10.1093/ajcn/71.6.1698S
  17. Lee J, Ahn MS, Hong KH (1998) A study on the content of general compounds, amino acid, vitamins, catechins, alkaloids in green, oolong and black tea. J Food Hyg Safety, 13, 377-382
  18. Wee JH, Park KH (2001) Isolation of 4-hydroxycinnamic acid, 3-methoxy-4-hydroxycinnamic acid, and 3,4- dihydroxybenzoic acid with antioxidative and antimicrobial activity from peanut (Arachis hypogaea) shell. Food Sci Biotechnol, 10, 551-556
  19. Nazaru KJ (2006) Flavonoid aglycones and phytosterols from the Erigeron acris L herb. Acta Polaniae Pharmaceutica, 63, 317-319
  20. Rhodes MJ, Price KR (1996) Analytical problems in the study of flavonoid compounds in onions. Food Chem, 57, 113-117 https://doi.org/10.1016/0308-8146(96)00147-1
  21. Sellappan S, Akoh CC (2002) Flavonoids and antioxidant capacity of Georgia-grown Vidalia onions. J Agric Food Chem, 50, 5338-5342 https://doi.org/10.1021/jf020333a
  22. Hwang IG, Kim HY, Lee SH, Hwang CR, Oh SH, Woo HS, Kim DJ, Lee JS, Jeong HS (2011) Isolation and identification of an antioxidant substance from heated onion (Allium cepa L). J Korean Soc Food Sci Nutr, 40, 470-474 https://doi.org/10.3746/jkfn.2011.40.3.470
  23. Mun SP, Ku CS (2006) Characterization of low molecular weight polyphenols from pine (Pinus radiata) bark. Food Sci Biotechnol, 15, 424-430
  24. Kim SJ, Lee HJ, Park KH, Rhee CO, Lim IJ, Chung JH, Moon JH (2008) Isolation and identification of low molecular phenolic antioxidants from ethylacetate layer of Korean black raspberry (Rubus coreanus Miquel) wine. Korean J Food Sci Technol, 40, 129-134
  25. Lee HH, Cho JY, Moon JH, Park KH (2011) Isolation and identification of antioxidative phenolic acids and flavonoid glycosides from Camellia japonica flowers. Hort Environ Biotechnol, 52, 270-277 https://doi.org/10.1007/s13580-011-0157-x
  26. Takahama U, Hirota S (2000) Deglucosidation of quercetin glucosides to the aglycone and formation of antifungal agents by peroxidase-dependent oxidation of quercetin on browning of onion scales. Plant Cell Physiol, 41, 1021-1029 https://doi.org/10.1093/pcp/pcd025

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