DOI QR코드

DOI QR Code

Isolation and Identification of Antioxidative Compounds in Fermented Glasswort (Salicornia herbacea L.) Juice

함초발효액으로부터 항산화 활성 물질의 분리 및 동정

  • Cho, Jeong-Yong (Dept. of Food Engineering and Solar Salt Biotechnology Research Center, Mokpo National University) ;
  • Park, Sun-Young (Dept. of Food Engineering and Solar Salt Biotechnology Research Center, Mokpo National University) ;
  • Shin, Mi-Jeong (Dept. of Food Engineering and Solar Salt Biotechnology Research Center, Mokpo National University) ;
  • Gao, Tian-Cheng (Dept. of Food Engineering and Solar Salt Biotechnology Research Center, Mokpo National University) ;
  • Moon, Jae-Hak (Dept. of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Ham, Kyung-Sik (Dept. of Food Engineering and Solar Salt Biotechnology Research Center, Mokpo National University)
  • 조정용 (목포대학교 식품공학과 및 천일염생명과학연구소) ;
  • 박선영 (목포대학교 식품공학과 및 천일염생명과학연구소) ;
  • 신미정 (목포대학교 식품공학과 및 천일염생명과학연구소) ;
  • 고천성 (목포대학교 식품공학과 및 천일염생명과학연구소) ;
  • 문제학 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 함경식 (목포대학교 식품공학과 및 천일염생명과학연구소)
  • Received : 2010.04.29
  • Accepted : 2010.06.09
  • Published : 2010.08.31

Abstract

The chloroform layer of fermented glasswort (Salicornia herbacea) juice was found to have higher radical-scavenging activity than the other layers by the assays using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) ($ABTS^+$) radicals. Two antioxidative compounds were isolated and purified from the chloroform layer by Sephadex LH-20 column chromatography using the guided assay of DPPH radical scavenging. Based on mass spectrometer and nuclear magnetic resonance, the isolated compounds were identified as cirsiumaldehyde (1) and chrysoeriol (2). This is the first study to report the presence of those compounds in fermented glasswort juice. Compound 2 showed higher radical-scavenging activity than 1.

함초발효액의 기능성 해명과 유용 기능성 성분 탐색연구의 일환으로 함초발효액으로부터 항산화 활성물질을 분리하여 구조해석 하였다. 함초발효액을 용매분획 하여 얻어진 용매분획물들 중 $CHCl_3$층이 높은 항산화 활성을 나타냈다. 그래서 $CHCl_3$층을 Sephadex LH-20 column chromatography의 분자체 효과 및 흡착능의 특성을 각각 이용하여 정제함으로써 2종의 항산화 활성물질을 분리하였다. 단리한 이들 화합물을 대상으로 MS 및 NMR 분석을 통하여 cirsiumaldehyde(1)와 chrysoeriol(2)로 각각 동정하였다. 이 화합물들은 $ABTS^+$ 및 DPPH radical-scavenging 활성을 나타냈으며, 화합물 2는 화합물 1에 비해 더 높은 활성을 나타냈다.

Keywords

References

  1. Kim CS, Song TG. 1983. Ecological studies on the halophyte communities at western and southern coasts in Korea. Korean J Ecol 6: 167-176.
  2. Min JG, Lee DS, Kim TJ, Park JH, Cho TY, Park DI. 2002. Chemical composition of Salicornia herbacea L. J Food Sci Nutr 7: 105-107. https://doi.org/10.3746/jfn.2002.7.1.105
  3. Bang MH, Kim HA, Cho YJ. 2002. Hypoglycemic and antioxidant effect of dietary hamcho in streptozotocin-induced diabetic rats. J Korean Soc Food Sci Nutr 31: 840-846. https://doi.org/10.3746/jkfn.2002.31.5.840
  4. Jo YC, Ahn JH, Chon SM, Lee KS, Bae TJ, Kang DS. 2002. Studies on pharmacological effects of glasswort (Salicornia herbacea L.). Korean J Med Corp Sci 10: 93-99.
  5. Park SH, Ko SK, Choi JG, Chung SH. 2006. Salicornia herbacea prevents high fat diet-induced hyperglycemia and hyperlipidemia in ICR mice. Arch Pharm Res 29: 256-264. https://doi.org/10.1007/BF02969402
  6. Ha JA, Lee SH, Kim HJ, Lee JY. 2006. The role of Salicornia herbacea in ovariectomy-induced oxidative stress. Biol Pharm Bull 29: 1305-1309. https://doi.org/10.1248/bpb.29.1305
  7. Jang HS, Kim KR, Choi SW, Woo MH, Choi JH. 2007. Antioxidant and antithrombus activities of enzyme-treated Salicornia herbacea extracts. Ann Nutr Metab 51: 119-125. https://doi.org/10.1159/000100826
  8. Kong CS, Kim YA, Kim MM, Park JS, Kim JA, Kim SK, Lee BJ, Nam YW. 2008. Flavonoid glycosides isolated from Salicornia herbacea inhibit matrix metalloproteinase in HT1080 cells. Toxicol in Vitro 22: 1742-1748. https://doi.org/10.1016/j.tiv.2008.07.013
  9. Im SA, Lee YR, Lee YH, Oh ST, Gerelchuluum T, Kim BH, Kim YS, Yun YP, Song SG, Lee CK. 2007. Synergistic activation of monocytes by polysaccharides isolated from Salicornia herbacea and interferon-$\gamma$. J Ethnopharmacol 111: 365-370. https://doi.org/10.1016/j.jep.2006.11.027
  10. Im SA, Kim KJ, Lee CK. 2006. Immunomodulatory activity of polysaccharides isolated from Salicornia herbacea. Int Immunopharmacol 6: 1451-1458. https://doi.org/10.1016/j.intimp.2006.04.011
  11. Lee JT, Jeong YS, An BJ. 2002. Physiological activity of Salicornia herbacea and its application for cosmetic materials. Korean J Herbol 17: 61-69.
  12. Lee YS, Lee HS, Shin KH, Kim BK, Lee SH. 2004. Constituents of the halophyte Salicornia herbaceae. Arch Pharm Res 27: 1034-1036. https://doi.org/10.1007/BF02975427
  13. Lee KY, Lee MH, Chang IY, Yoon SP, Lim DY, Jeon YJ. 2006. Macrophage activitation by polysaccharide fraction isolated from Salicornia herbacea. J Ethnopharm 103: 372-378. https://doi.org/10.1016/j.jep.2005.08.037
  14. Park SH, Kim KS. 2004. Isolation and identification of antioxidant flavonoids from Salicornia herbacea L. J Korean Soc Appl Biol Chem 47: 120-123.
  15. Chung YC, Chun HK, Yang JY, Kim JY, Han EH, Kho YH, Jeong HG. 2005. Tungtungmadic acid, a novel antioxidant, from Salicornia herbacea. Arch Pharm Res 28: 1122-1126. https://doi.org/10.1007/BF02972972
  16. Kong CS, Kim JA, Qian ZJ, Kim YA, Lee JI, Kim SK, Nam TJ, Seo YW. 2009. Protective effect of isorhamnetin 3-O-$\beta$-D-glucopyranoside from Salicornia herbacea against oxidation-induced cell damage. Food Chem Taxicol 47: 1914-1920. https://doi.org/10.1016/j.fct.2009.05.002
  17. Hwang YP, Yun HJ, Chun HK, Chung YC, Kim HK, Jeong MH, Yoon TR, Jeong HG. 2009. Protective mechanisms of 4-caffeoyl, 4-dihydrocaffeoyl quinic acid from Salicornia herbacea against tert-butylhydroperoxide-induced oxidative damage. Chemico-Biological Interactions 181: 366-376. https://doi.org/10.1016/j.cbi.2009.07.017
  18. Lee YS, Lee SH, Kim BK, Oguchi K, Shin KH. 2005. Inhibitory effects of isorhamnetin-3-O-$\beta$-D-glucoside from Salicornia herbacea on rat lens aldose reductase and sorbitol accumulation in streptozotocin-induced diabetic rat tissues. Biol Pharm Bull 28: 916-918. https://doi.org/10.1248/bpb.28.916
  19. Song TC, Lee CH, Kim YE, Kim IH, Han DS, Yang DH. 2007. The Functionality of the saltwort (Salicornia herbacea L.) extract fermented juice. J Korean Soc Food Sci Nutr 36: 395-399. https://doi.org/10.3746/jkfn.2007.36.4.395
  20. Park IB, Park JW, Lee YJ, Shin GW, Kim HS, Jo YC. 2009. Quality characteristic of glasswort (Salicornia herbacea L.) fermented by Bacillus subtilis. J Korean Soc Food Sci Nutr 38: 902-908. https://doi.org/10.3746/jkfn.2009.38.7.902
  21. Abe N, Nemoto A, Tsuchiya Y, Hojo H, Hirota A. 2000. Studies of the 1,1-diphenyl-2-picrylhydrazyl radical scavenging mechanism for a 2-pyrone compound. Biosci Biotech Bioch 64: 306-333. https://doi.org/10.1271/bbb.64.306
  22. Takao T, Kitatani F, Watanabe N, Yagi A, Sakata K. 1994. 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. https://doi.org/10.1271/bbb.58.1780
  23. Park YH, Moon BH, Yang HJ, Lee YS, Lee EJ, Lim JY. 2007. Complete assignments of NMR data of 13 hydroxymethoxyflavones. Magn Reson Chem 45: 1072-1075. https://doi.org/10.1002/mrc.2063
  24. Shen YM, Mu QZ. 1990. New furans from Cirsium chlorolepis. Planta Med 56: 472-474. https://doi.org/10.1055/s-2006-961014
  25. Yun-Choi HS, Pyo MK, Park KM. 1997. Cirsiumaldehyde from Gastrodia elata. Nat Prod Sci 3: 104-105.
  26. Chambel P, Oliveira MB, Andrade PB, Fernandes JO, Seabra RM, Ferreira MA. 1998. Identification of 5,5'-oxydimethylene-bis(2-furaldehyde) by thermal decomposition of 5-hydroxymethyl-2-furfuraldehyde. Food Chem 63: 473-477. https://doi.org/10.1016/S0308-8146(98)00062-4
  27. Yu NJ, Guo SX. 2002. Studies on the chemical constituents from culture filtrate of a fungus isolated from Ganoderma lucidum. Nat Prod Res Develop 14: 24-26.
  28. Takemura H, Uchiyama H, Ohura T, Sakakibara H, Kuruto R, Amagi T, Shimoi K. 2010. A methoxyflavonoid, chrysoeriol, selectively inhibits the formation of a carcinogenic estrogen metabolite in MCF-7 breast cancer cells. J Steroid Biochem Biol 118: 70-76. https://doi.org/10.1016/j.jsbmb.2009.10.002
  29. Mishra B, Priyadarsini I, Kumar MS, Unnikrishnan MK, Mohan H. 2003. Effect of O-glycosilation on the antioxidant activity and free radical reactions of a plant flavonoid, chrysoeriol. Bioorg Med Chem 11: 2677-2685. https://doi.org/10.1016/S0968-0896(03)00232-3
  30. Zhang CZ, Zhong Y, Sun ZJ, Ma YY. 2009. Purification and characterization of SDG-β-D-glucosidase hydrolyzing secoisolariciresinol diglucoside to secoisolariciresinol from Aspergillus oryzae. Pro Biochem 44: 607-611. https://doi.org/10.1016/j.procbio.2009.01.007
  31. Ito J, Sahara H, Kaya M, Hata Y, Shibasaki S, Kawata K, Ishida S, Ogino C, Fukuda H, Kondo A. 2008. Characterization of yeast cell surface displayed Aspergillus oryzae $\beta$-glucosidase 1 high hydrolytic activity for soybean isoflavone. J Mol Catal B: Enzymatic 55: 69-75. https://doi.org/10.1016/j.molcatb.2008.01.003

Cited by

  1. Isolation and identification of antioxidative compounds and their activities from Suaeda japonica vol.22, pp.6, 2013, https://doi.org/10.1007/s10068-013-0250-2
  2. Anti-stress and Anti-histamine Effects of Phragmites communis, Salicornia herbacea, and Prunus mume vol.14, pp.2, 2016, https://doi.org/10.20402/ajbc.2016.0029
  3. Microbial Population of Foodborne Pathogens during Fermentation of Mulberry Wort vol.31, pp.6, 2016, https://doi.org/10.13103/JFHS.2016.31.6.458
  4. Protective Effect of Quercus salicina Blume Extract in Calcium Oxalate Urolithiasis Model vol.25, pp.5, 2012, https://doi.org/10.7732/kjpr.2012.25.5.507
  5. Germination is enhanced by removal of the funiculus in the halophyte glasswort (Salicornia herbacea) vol.57, pp.4, 2016, https://doi.org/10.1007/s13580-016-0108-7
  6. Physicochemical Characteristics and Physiological Activities of Naturally Fermented Glasswort (Salicornia herbacea L.) Juice vol.40, pp.11, 2011, https://doi.org/10.3746/jkfn.2011.40.11.1493
  7. 함초 씨의 항균, 항산화 및 항혈전 활성 vol.44, pp.4, 2010, https://doi.org/10.4014/mbl.1609.09002
  8. 함초의 부위별 항산화 및 항혈전 활성 vol.44, pp.3, 2010, https://doi.org/10.4014/mbl.1607.07003
  9. 수확시기에 따른 함초의 항산화 및 항혈전 활성의 변화 vol.26, pp.9, 2010, https://doi.org/10.5352/jls.2016.26.9.1033
  10. ISSR 마커를 이용한 서식 면적에 따른 퉁퉁마디의 유전적 다양성 vol.31, pp.6, 2010, https://doi.org/10.13047/kjee.2017.31.6.492