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Antioxidant Activity of Flavonoids and Their Glucosides from Sonchus oleraceus L.

  • Yin, Jie (School of Biotechnology, Kangwon National University) ;
  • Si, Chuan-Ling (Tianjin Key Laboratory of Pulp & Paper, Tianjin University of Science & Technology) ;
  • Wang, Myeong-Hyeon (School of Biotechnology, Kangwon National University)
  • Published : 2008.04.30

Abstract

Eight compounds, including 2 flavones, luteolin (1) and apigenin (2), 2 flavonols, kaempferol (3) and quercetin (4), and 4 flavonoid glucosides, luteolin-7-O-${\beta}$-D-glucoside (5), apigetrin (6), astragalin (7), and isoquercitrin (8), isolated from the whole herb of Sonchus oleraceus L. were analyzed on the basis of chemical and spectroscopic evidence. This was the first time to report compounds 3, 4, 6, 7 and 8 from the Sonchus oleraceus L. The antioxidant activities of the isolated flavonoids and their glucoside derivatives were evaluated by DPPH free radical-scavenging assay, showing that compounds 1, 3, 4 and 8 exhibited stronger antioxidant activities compared with ${\alpha}$, tocopherol and curcumin. Flavonoids containing more hydroxyl groups exhibited better antioxidant activities. The antioxidant activity of flavonols was superior to their corresponding flavones, and that of aglycone are more potent than their glucoside derivatives.

Keywords

References

  1. Agrawal PK (1989) Carbon-13 NMR of flavonoids. Elsevier, New York, USA
  2. Akdemir AS, Tati II, Saraccoglu I, Ismailoglu UB, Sahin- Erdemli I, and Dalis I (2001) Polyphenolic compounds from Geranium pratense and their free radical scavenging activities. Phytochemistry 56, 189-193 https://doi.org/10.1016/S0031-9422(00)00367-8
  3. Bai YH, Masayoshi A, and Zhang WB (2007) Study on the chemical constituents of the whole plant of Sonchus oleraceus L. Journal of Qiqihar University 23, 1-3
  4. Gutteridge JMC and Halliwell B (1994) Antioxidants in Nutrition, Health, and Diesease. Oxford University Press, Oxford, pp. 1-62
  5. Halliwell B (1994) Free radical, antioxidants, and human disease: Curiosity, cause, or consequence. Lancet 344, 721-724 https://doi.org/10.1016/S0140-6736(94)92211-X
  6. Holm LG, Plucknett DL, Pancho JV, and Herberger JP (1977) The world's worst weeds: Distribution and Biology, University Press of Hawaii, Honolulu, pp. 436-439
  7. Hu PZ, Zou CZ, and Zhu Y (2005) Lipid-soluble chemical constituents in Sonchus oleraceus. Acta Bot. Boreal. Occident Sin 25, 1234-1237
  8. Jiangsu New Medical College (1977) The Chinese Medicine Dictionary, Shanghai People's Publishing House, Shanghai, pp. 1286-1288
  9. Li CG, Qu GR, Niu HY, Dong CX, and Zhu Y (2005) Journal of Henan Normal University (Natural Science) 33, 128-132
  10. Markham KR and Chari VM (1982) Carbon-13 NMR spectroscopy of flavonoids, in Harboren JB and Mabry T (eds.), The Flavonoids: Advances in research, Chapman and Hall Ltd., London, UK, pp. 119-134
  11. Pietta PG (2000) Flavonoids as antioxidants. J Nat Prod 63, 1035-1042 https://doi.org/10.1021/np9904509
  12. Scalbert A and Williamson G (2000) Dietary intake and bioavailability of polypenols. J Nutr 130, 2073S-2085S
  13. Seidel V, Bailleul F and Waterman PG (2000) (Rel)-$1\beta,2\alpha$-di-(2,4-dihydroxy-6methoxybenzoyl)-$3\beta,4\alpha$-di-(di-(4-methoxyphenyl)- cyclobutane and other flavonoids from the aerial parts of Goniothalamus gardneri and Goniothalamus thwaitesii. Phytochemistry 55, 439-446 https://doi.org/10.1016/S0031-9422(00)00346-0
  14. Si CL, Kim JK, Kwon DJ, and Bae YS (2006) Phenolic compounds from the fruits of Paulownia coreana Uyeki. Mokchae Konghak 34, 79-85
  15. Ternai B and Markham KR (1976) Carbon-13 NMR studies of flavonoids-I: flavones and flavonols. Tetrahedron 32, 565-569 https://doi.org/10.1016/S0040-4020(01)93772-X
  16. Wanasundara UN and Shahidi F (1998) Antioxidant and prooxidant activity of green tea extracts in maine oils. Food Chem 63, 335-342 https://doi.org/10.1016/S0308-8146(98)00025-9
  17. Weisburger JH, Hara Y, Sulan L, Luo FQ, Pittman B and Zang E (1996) Tea polyphenols as inhibitors of mutigenicity of major classes carcionogens. Mutat Res 371, 57-63 https://doi.org/10.1016/S0165-1218(96)90094-4
  18. Wenkert E and Gottlieb HE (1977) Carbon-13 nuclear magnetic resonance spectroscopy of flavonoid and isoflavonoid compounds. Phytochemistry 16, 1811-1816 https://doi.org/10.1016/0031-9422(71)85095-1
  19. Xu Y and Liang JJ (2005) Chemical Constituent s of Sonchus oleraceus L. J China Pharmaceutial Univ 36, 411-413
  20. Yin J, Kwon GJ and Wang MH (2007) Studies of the antioxidant and antiproliferative activities of Sonchus oleraceus L. extracts. Nutri Res Prac, 1, 189-194 https://doi.org/10.4162/nrp.2007.1.3.189

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