Food Science and Biotechnology

, Volume 22, Issue 6, pp 1547–1557 | Cite as

Isolation and identification of antioxidative compounds and their activities from Suaeda japonica

  • Jeong-Yong Cho
  • Xing Yang
  • Kyung-Hee Park
  • Hye Jin Park
  • Sun-Young Park
  • Jae-Hak Moon
  • Kyung-Sik Ham
Research Article

Abstract

The ethyl acetate (EtOAc) and chloroform (CHCl3) layers obtained after solvent fractionation of a H2O suspension of powdered Suaeda japonica juice showed higher 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicalscavenging activity than other layers. Eighteen compounds were purified and isolated from the EtOAc and CHCl3 layers using chromatography following DPPH radicalscavenging assay. These compounds were identified as dihydroferulic acid methyl ester (1), pyrocatechol (2), syringic acid (3), apigenin (4), isorhamnetin (5), kaempferol (6), dihydroferulic acid (7), vanillic acid (8), 4-hydroxybenzoic acid (9), acetophlorglucine (10), homoeriodictyol (11), naringenin (12), quercetin (13), luteolin (14), 9-epiblumenol C (15), scopoletin (16), dihydroisorhamnetin (17), and chrysoeriol (18). The structures of these compounds were determined by mass spectrometry and nuclear magnetic resonance analyses. The isolated compounds were newly identified from this plant. Compounds 13 and 14 exhibited higher DPPH radical-scavenging activity and an inhibition effect against ferric ion-induced lipid oxidation of rat liver when compared to α-tocopherol and other compounds.

Keywords

Suaeda japonica antioxidant flavonoid phenolics DPPH radical-scavenging activity 

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References

  1. 1.
    Kim JA, Choo YS, Lee IJ, Bae JJ, Kim IS, Choo BH, Song SD. Adaptations and physiolpgical chararcteristivs of three Chenopodiaceae species under saline environments. Korean J. Ecol. 25: 101–107 (2002)CrossRefGoogle Scholar
  2. 2.
    Wada N, Zhang J, Jinno N, Okubo A, Yamazaki S. Component analysis of a halophyte, Suaeda japonica, grown on the shore of Ariake Sea. Bunseki Kagaku 52: 843–846 (2003)CrossRefGoogle Scholar
  3. 3.
    Choi JI, Kim YJ, Kim JH, Song BS, Yoon Y, Byun MW, Kwon JH, Chun SS, Lee JW. Antioxidant activities of the extract fractions from Suaeda japonica. J. Korean Soc. Food Sci. Nutr. 38: 131–135 (2009)CrossRefGoogle Scholar
  4. 4.
    Korea Food and Drug Administration. Available from: http://fse.foodnara.go.kr/origin. Assessed Feb. 20, 2013.
  5. 5.
    Kim JH, Song JY, Lee JM, Oh SH, Lee HJ, Choi HJ, Go JM, Kim YH. A study on physiochemical property of Salicornia herbacea & Suaeda japonica. J. Fd. Hyg. Safety 25: 170–179 (2010)Google Scholar
  6. 6.
    Choi JI, Kim YJ, Kim JH, Kwon JH, Ahn DH, Chun SS, Lee JW. Physiological activities of Suaeda japonica extracts on harvest season. J. Korean Soc. Food Sci. Nutr. 39: 99–104 (2010)CrossRefGoogle Scholar
  7. 7.
    Lee KS, Gim JC, Son SM, Lee KY. Antioxidative effects of Suaeda japonica ethanol extract and solvent partitioned fractions. J. Korean Soc. Food Sci. Nutr. 40: 804–808 (2011)CrossRefGoogle Scholar
  8. 8.
    Lee KS, Kim AJ, Lee KY. Analysis of chemical composition and antioxidant activity of of Suaeda japonica. J. East Asian Soc. Dietary life 22: 521–526 (2012)Google Scholar
  9. 9.
    Tanimoto S, Itoh Y, Yokoishi Y. Possible involvement of greening in cell growth of Suaeda japonica under salt stress. Plant Cell Physiol. 38: 129–132 (1997)CrossRefGoogle Scholar
  10. 10.
    Kim JS, Lee SH, Son EM, Pan X, Kim YA, Lee GS, Seo YW, Lee BJ. Phytochemical constituents of Suaeda japonica Makino. J. Crop Sci. 50: 208–210 (2005)Google Scholar
  11. 11.
    Hayakawa K, Agarie S. Physiological roles of betacyanin in a halophyte, Suaeda japonica Makino. Plant Prod. Sci. 13: 351–359 (2010)CrossRefGoogle Scholar
  12. 12.
    Park SH, Ko SK, Choi JG, Chung SH. Salicornia herbacea prevents high fat diet-induced hyperglycemia and hyperlipidemia in ICR mice. Arch. Pharm. Res. 29: 256–264 (2006)CrossRefGoogle Scholar
  13. 13.
    Lee YS, Lee SH, Kim BK, Oguchi K, Shin KH. Inhibitory effects of isorhamnetin-3-O-β-d-glucoside from Salicornia herbacea on rat lens aldose reductase and sorbitol accumulation in streptozotocininduced diabetic rat tissues. Biol. Pharm. Bull. 28: 916–918 (2005).CrossRefGoogle Scholar
  14. 14.
    Ha JA, Lee SH, Kim HJ, Lee JY. The role of Salicornia herbacea in ovariectomy-induced oxidative stress. Biol. Pharm. Bull. 29: 1305–1309 (2006).CrossRefGoogle Scholar
  15. 15.
    Kong CS, Kim YA, Kim MM, Park JS, Kim JA, Kim SK, Lee BJ, Nam YW. Flavonoid glycosides isolated from Salicornia herbacea inhibit matrix metalloproteinase in HT1080 cells. Toxicol. In Vitro 22: 1742–1748 (2008)CrossRefGoogle Scholar
  16. 16.
    Lee YS, Lee HS, Shin KH, Kim BK, Lee SH. Constituents of the halophyte Salicornia herbaceae. Arch. Pharm. Res. 27: 1034–1036 (2004).CrossRefGoogle Scholar
  17. 17.
    Im SA, Lee YR, Lee YH, Oh ST, Gerelchuluum T, Kim BH, Kim YS, Yun YP, Song SG, Lee CK. Synergistic activation of monocytes by polysaccharides isolated from Salicornia herbacea and interferon-γ. J. Ethnopharmacol. 111: 365–370 (2007)CrossRefGoogle Scholar
  18. 18.
    Park SH, Kim KS. Isolation and identification of antioxidant flavonoids from Salicornia herbacea L. J. Korean Soc. Appl. Biol. Chem. 47: 120–123 (2004)Google Scholar
  19. 19.
    Chung YC, Chun HK, Yang JY, Kim JY, Han EH, Kho YH, Jeong HG. Tungtungmadic acid, a novel antioxidant, from Salicornia herbacea. Arch. Pharm. Res. 28: 1122–1126 (2005)CrossRefGoogle Scholar
  20. 20.
    Kim JY, Cho JY, Ma YK, Park KY, Lee SH, Ham KS, Lee HJ, Park KH, Moon JH. Dicaffeoylquinic acid derivatives and flavonoid glucosides from glasswort (Salicornia herbacea L.) and their antioxidative activity. Food Chem. 125: 55–62 (2011)CrossRefGoogle Scholar
  21. 21.
    Abe N, Nemoto A, Tsuchiya Y, Hojo H, Hirota A. Studies of the 1,1-diphenyl-2-picrylhydrazyl radical scavenging mechanism for a 2-pyrone compound. Biosci. Biotech. Bioch. 64: 306–333 (2000)CrossRefGoogle Scholar
  22. 22.
    Takao T, Kitatani F, Watanabe N, Yagi A, Sakata K. A simple screening method for antioxidants and isolation of several antioxidants produced by marine bacteria from fish and shellfish. Biosci. Biotech. Bioch. 58: 1780–1783 (1994)CrossRefGoogle Scholar
  23. 23.
    Bafna A, Mishra S. Antioxidant and immunomodulatory activity of the alkaloidal fraction of Cissampelos pareira Linn. Sci. Pharm. 78: 21–31 (2009)CrossRefGoogle Scholar
  24. 24.
    Beck JJ, Kim JH, Campbel BC, Chou SC. Fungicidal activities of dihydroferulic acid alkyl ester analogues. J. Nat. Prod. 70: 779–782 (2007)CrossRefGoogle Scholar
  25. 25.
    Kim SJ, Lee HJ, Park KH, Rhee CO, Lim IJ, Chung HJ, Moon JH. Isolation and identification of low molecular phenolic antioxidants from ethylacetate layer of Korean black raspberry (Rubus coreanus) wine. Korean J. Food Sci. Technol. 40: 129–134 (2008)Google Scholar
  26. 26.
    Liu Z, Li S, Han N, Sun D, Gao Y, Yin Y. Studies on the chemical constituents of the vines of Streptocaulon juventas (Lour) Merr. Asian J. Trad. Med. 3(5): 193–198 (2008)Google Scholar
  27. 27.
    Owen RW, Haubner R, Mier W, Giacosa A, Hull WE, Spiegelhalder B, Bartsch H. Isolation, structure elucidation and antioxidant potential of the major phenolic and flavonoid compounds in brined olive drupes. Food Chem. Toxicol. 41: 703–717 (2003)CrossRefGoogle Scholar
  28. 28.
    Hyun MO. Inhibitory activity of isorhamnetin from Persicaria thunbergii on farnesyl protein transferase. Arch. Pham. Res. 28: 169–171 (2005)Google Scholar
  29. 29.
    Kim DK. A furan derivative from Cornus ifficinalis. Arch. Pham. Res. 21: 787–789 (1998)CrossRefGoogle Scholar
  30. 30.
    Maridani MY, Scobie H, O’Brien PJ. Metabolism of caffeic acid by isolated rat hepatocytes and subcellular fractions. Toxicol. Lett. 133: 141–151 (2002)CrossRefGoogle Scholar
  31. 31.
    Sang SM. Antioxodative phenolic compounds isolated from almond skins (Prunus amygdalus Batsch). J. Agr. Food Chem. 50: 2459–2463 (2002)CrossRefGoogle Scholar
  32. 32.
    Lee HH, Cho JY, Moon JH, Park KH. Isolation and identification of antioxidative phenolic acids and flavonoid glycosides from Camellia japonica flowers. Hort. Environ. Biotechnol. 52: 270–277 (2011)CrossRefGoogle Scholar
  33. 33.
    Yoon WJ, Lee JA, Kim JY, Oh DJ, Jung YH, Lee WJ, Park SY. Anti-oxidant activities and anti-inflammatory effects on Artemisia scoparia. Korean J. Pharmacogn. 37: 235–240 (2006).Google Scholar
  34. 34.
    Wang XG. Anitfungal falvonoids from Ficus sarmentosa var. henryi (King) corner. Agr. Sci. China 9: 690–694 (2010)CrossRefGoogle Scholar
  35. 35.
    Olsen HT, Stafford GI, van Staden J, Christensen SB, Jager AK. Isolation of the MAO-inhibitor narigenin from Mentha aquatic L. J. Ethnopharmacol. 117: 500–502 (2008)CrossRefGoogle Scholar
  36. 36.
    Cho JY, Yoon I, Jung DH, Lee KH, Moon JH, Park KH. Jaboticabin and flavonoids from the ripened fruit of Rubus coreanum. Food Sci. Biotechnol. 21: 1081–1086 (2012)CrossRefGoogle Scholar
  37. 37.
    Nazaruk J. Flavonoid aglycones and phytosterols from the Erigreron acrus L. herb. Acta Pol. Pharm. 63: 317–319 (2006)Google Scholar
  38. 38.
    Chung SC, Hwang BY, Oh GJ, Kang SJ, Kim MJ, Choi WH, Lee KS, Ro JS. Chemical components from the stem bark of Rhus javanica L. Korean J. Pharmacogn. 30: 295–300 (1999)Google Scholar
  39. 39.
    Saewan N, Koysomboon S, Chantrapromma K. Anti-tyrosinase and anti-cancer activities of flavonoids from Blumea balsamifera DC. J. Med. Plants Res. 5: 1018–1025 (2011)Google Scholar
  40. 40.
    Cho JY, Park SY, Shin MJ, Gao TC, Moon JH, Ham KS. Isolation and identification of antioxidative compounds in fermented glasswort (Salicornia herbacea L.) juice. J. Korean Soc. Food Sci. Nutr. 39: 1137–1142 (2010)CrossRefGoogle Scholar
  41. 41.
    Matsunami K, Otsuka H, Takeda Y. Structural revisions of blumenol C glucoside and by xantionoside B. Chem. Pharm. Bull. 58: 438–441 (2010)CrossRefGoogle Scholar
  42. 42.
    Kim SJ, Cho JY, Wee JH, Jang MY, Kim C, Rim YS, Shin SC, Ma SJ, Moon JH, Park KH. Isolation and characterization of antioxidative compounds from the aerial parts of Angelica keiskei. Food Sci. Biotechnol. 14: 58–63 (2005)Google Scholar
  43. 43.
    Wee JH, Moon JH, Eun JB, Chung JH, Kim YG, Park KH. Isolation and identification of antioxidants from peanut shells and the relationship between structure and antioxidant activity. Food Sci. Biotechnol. 16: 116–122 (2007)Google Scholar
  44. 44.
    Galbraith MN, Horn DHS. Structures of the natural products blumenols A, B, and C. J. Chem. Soc. Chem. Commun. 1: 113–114 (1972)CrossRefGoogle Scholar
  45. 45.
    Shirai M, Moon JH, Tsushida T, Terao J. Inhibitory effect of a quercetin metabolite, quercetin 3-O-β-d-glucuronide, on lipid peroxidation in liposomal membranes. J. Agr. Food Chem. 49: 5602–5608 (2001)CrossRefGoogle Scholar
  46. 46.
    Rice-Evans CA, Miller NJ, Paganga G. Structure antioxidant activity relationships of flavonoids and phenolic acids. Free Rad. Biol. Med. 20: 933–956 (1996)CrossRefGoogle Scholar
  47. 47.
    Mladěnka P, Macŕková K., Filipský T, Zatloulalová L, Jahodář L, Bovicelli P, Silvestri IP, Hrdina R, Saso L. In vitro analysis of iron chelating activity of flovonoids. J. Inorg. Biochem. 105: 693–701 (2011)CrossRefGoogle Scholar
  48. 48.
    Nijveldt RJ, Nood E, Hoorn DEC, Boelens PG, Norren K, Leeuwen PAM. Flavonoids: a review of probable mechanisms of action and potential applications. Am. J. Clin. Nutr. 74: 418–25 (2001)Google Scholar
  49. 49.
    Waśkiewicz A, Muzolf-Panek M, Goliński P. Phenolic content changes in plants under salt stress. Biol. Med. 3: S232–S249 (2011)Google Scholar

Copyright information

© The Korean Society of Food Science and Technology and Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  • Jeong-Yong Cho
    • 1
  • Xing Yang
    • 1
  • Kyung-Hee Park
    • 1
  • Hye Jin Park
    • 1
  • Sun-Young Park
    • 1
  • Jae-Hak Moon
    • 2
  • Kyung-Sik Ham
    • 1
  1. 1.Department of Food Science & Biotechnology, and Solar Salt Biotechnology Research CenterMokpo National UniversityMuan, JeonnamKorea
  2. 2.Department of Food Science & Technology, and Functional Food Research CenterChonnam National UniversityGwangjuKorea

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