Advertisement

Journal of Zhejiang University SCIENCE B

, Volume 9, Issue 5, pp 407–415 | Cite as

Tannins from Canarium album with potent antioxidant activity

  • Liang-liang Zhang
  • Yi-ming Lin
Article

Abstract

The contents of total phenolics and extractable condensed tannins in the leaves, twigs and stem bark of Canarium album were determined. The structural heterogeneity of condensed tannings from stem bark was characterized by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and nuclear magnetic resonance (NMR) analyses. The results show the predominance of signals representative of procyanidins and prodelphinidins. In addition, epicatechin and epigallocatechin polymers with galloylated procyanidin or prodelphinidin were also observed. The tannins were screened for their potential antioxidant activities using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and ferric reducing/antioxidant power (FRAP) model systems. Tannins extracted from leaves, twigs and stem bark all showed a very good DPPH radical scavenging activity and ferric reducing power.

Key words

Canarium album Tannins Antioxidant capacity Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) 

CLC number

Q946.84 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Bagchi, D., Bagchi, M., Stohs, S.J., Das, D.K., Ray, S.D., Kuszynski, C.A., Joshi, S.S., Pruess, H.G., 2000. Free radicals and grape seed proanthocyanidin extract: importance in human health and disease prevention. Toxicology, 148(2–3):187–197. [doi:10.1016/S0300-483X(00)00210-9]PubMedCrossRefGoogle Scholar
  2. Behrens, A., Maie, N., Knicker, H., Kögel-Knabner, I., 2003. MALDI-TOF mass spectrometry and PSD fragmentation as means for the analysis of condensed tannins in plant leaves and needles. Phytochemistry, 62(7):1159–1170. [doi:10.1016/S0031-9422(02)00660-X]PubMedCrossRefGoogle Scholar
  3. Benzie, I.F.F., Strain, J.J., 1996. The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: the FRAP assay. Analytical Biochemistry, 239(1):70–76. [doi:10.1006/abio.1996.0292]PubMedCrossRefGoogle Scholar
  4. Braca, A., Tommasi, N.D., Bari, L.D., Pizza, C., Politi, M., Morelli, I., 2001. Antioxidant principles from Bauhinia terapotensis. Journal of Natural Products, 64(7):892–895. [doi:10.1021/np0100845]PubMedCrossRefGoogle Scholar
  5. Brand-Williams, W., Cuvelier, M.E., Berset, C., 1995. Use of free radical method to evaluate antioxidant activity. Food Science and Technology, 28(1):25–30. [doi:10.1016/S0023-6438(95)80008-5]Google Scholar
  6. Ding, B.P., 1999. Pharmacology of Qingguo pills on relieving cough. China Traditional Patent Medicine, 21:27–28 (in Chinese).Google Scholar
  7. Es-Safi, N.E., Guyot, S., Ducrot, P.H., 2006. NMR, ESI/MS, and MALDI-TOF/MS analysis of pear juice polymeric proanthocyanidins with potent free radical scavenging activity. Journal of Agricultural and Food Chemistry, 54(19):6969–6977. [doi:10.1021/jf061090f]PubMedCrossRefGoogle Scholar
  8. Graham, H.D., 1992. Stabilization of the Prussian blue color in the determination of polyphenols. Journal of Agricultural and Food Chemistry, 40(5):801–805. [doi:10.1021/jf00017a018]CrossRefGoogle Scholar
  9. Haslam, E., 1998. Practical Polyphenolics: From Structure to Molecular Recognition and Physiological Action. Cambridge University Press, Cambridge, p.422.Google Scholar
  10. Hernes, P.J., Benner, R., Cowie, G.L., Goni, M.A., Bergamaschi, B.A., Hedges, J.I., 2001. Tannin diagenesis in mangrove leaves from a tropical estuary: a novel molecular approach. Geochimica et Cosmochimica Acta, 65(18):3109–3122. [doi:10.1016/S0016-7037(01)00641-X]CrossRefGoogle Scholar
  11. Ishida, Y., Kitagawa, K., Goto, K., Ohtani, H., 2005. Solid sampling technique for direct detection of condensed tannins in bark by matrix-assisted laser desorption/ionization mass spectrometry. Rapid Communications in Mass Spectrometry, 19(5):706–710. [doi:10.1002/rcm.1845]PubMedCrossRefGoogle Scholar
  12. Krueger, C.G., Vestling, M.M., Reed, J.D., 2003. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of heteropolyflavan-3-ols and glucosylated heteropolyflavans in sorghum [Sorghum bicolor (L.) Moench]. Journal of Agricultural and Food Chemistry, 51(3):538–543. [doi:10.1021/jf020746b]PubMedCrossRefGoogle Scholar
  13. Lin, Y.M., Liu, J.W., Xiang, P., Lin, P., Ye, G.F., Sternberg, L. da S.L., 2006. Tannin dynamics of propagules and leaves of Kandelia candel and Bruguiera gymnorrhiza in the Jiulong River Estuary, Fujian, China. Biogeochemistry, 78(3):343–359. [doi:10.1007/s10533-005-4427-5]CrossRefGoogle Scholar
  14. Meir, S., Kanner, J., Akiri, B., Hadas, S.P., 1995. Determination and involvement of aqueous reducing compounds in oxidative defense systems of various senescing leaves. Journal of Agricultural and Food Chemistry, 43(7):1813–1815. [doi:10.1021/jf00055a012]CrossRefGoogle Scholar
  15. Ohnishi-Kameyama, M., Yanagida, A., Kanda, T., Nagata, T., 1997. Identification of catechin oligomers from apple (Malus pumila cv. Fuji) in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and fast-atom bombardment mass spectrometry. Rapid Communications in Mass Spectrometry, 11(1):31–36. [doi:10.1002/(SICI)1097-0231(19970115)11:1〈31::AID-RCM784〉3.0.CO;2-T]PubMedCrossRefGoogle Scholar
  16. Oszmianski, J., Wojdylo, A., Lamer-Zarawska, E., Swiader, K., 2007. Antioxidant tannins from Rosaceae plant roots. Food Chemistry, 100(2):579–583. [doi:10.1016/j.food-chem.2005.09.086]CrossRefGoogle Scholar
  17. Ricarda Da Silva, J.M., Darmon, N., Fernandez, Y., 1991. Oxygen free radical scavenger capacity in aqueous models of different procyanidins from grape seeds. Journal of Agricultural and Food Chemistry, 39(9):1549–1552. [doi:10.1021/jf00009a002]CrossRefGoogle Scholar
  18. Santos-Buelga, C., Scalbert, A., 2000. Proantocyanidins and tannin-like compounds: nature, occurrence dietary intake and effects on nutrition and health. Journal of the Science of Food and Agriculture, 80(7):1094–1117. [doi:10.1002/(SICI)1097-0010(20000515)80:7〈1094::AID-JSFA569〉3.0.CO;2-1]CrossRefGoogle Scholar
  19. Spencer, P., Sivakumaran, A., Fraser, K., Foo, L.Y., Lane, G.A., Edwards, P.J.B., Meagher, L.P., 2007. Isolation and characterization of procyanidins from Rumex obtusifolius. Phytochemical Analysis, 18(3):193–203. [doi:10.1002/pca.967]PubMedCrossRefGoogle Scholar
  20. Terrill, T.H., Rowan, A.M., Douglas, G.B., Barry, T.N., 1992. Determination of extractable and bound condensed tannin concentrations in forage plants, protein concentrate meals and cereal grains. Journal of the Science of Food and Agriculture, 58(3):321–329. [doi:10.1002/jsfa.2740580306]CrossRefGoogle Scholar
  21. Visioli, F., Bellomo, G., Galli, C., 1998. Free radical-scavenging properties of olive oil polyphenols. Biochemical and Biophysical Research Communications, 247(1):60–64. [doi:10.1006/bbrc.1998.8735]PubMedCrossRefGoogle Scholar
  22. Wei, H., Peng, W., Mao, Y.M., 1999. Chemical constituents of fruit from Canarium album. Journal of Chinese Material Medicine, 24(7):421–423 (in Chinese).Google Scholar
  23. Wu, L., 2007. Effect of chlorogenic acid on antioxidant activity of Flos lonicerae extracts. Journal of Zhejiang University SCIENCE B, 8(9):673–679. [doi:10.1631/jzus.2007.B0673]PubMedCrossRefGoogle Scholar
  24. Xiang, P., Lin, Y.M., Lin, P., Xiang, C., 2006. Effects of adduct ions on matrix-assisted laser desorption/ionization time of flight mass spectrometry of condensed tannins: a prerequisite knowledge. Chinese Journal of Analytical Chemistry, 34(7):1019–1022. [doi:10.1016/S1872-2040(06)60047-9]CrossRefGoogle Scholar
  25. Xiang, P., Lin, Y.M., Lin, P., Xiang, C., Yang, Z.W., Lu, Z.M., 2007. Effect of cationization reagents on the matrix-assisted laser desorption/ionization time-of-flight mass spectrum of Chinese gallotannins. Journal of Applied Polymer Science, 105(2):859–864. [doi:10.1002/app.26373]CrossRefGoogle Scholar
  26. Yang, Y., Chien, M., 2000. Characterization of grape procyanidins using high-performance liquid chromatography/mass spectrometry and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Journal of Agricultural and Food Chemistry, 48(9):3990–3996. [doi:10.1021/jf000316q]PubMedCrossRefGoogle Scholar
  27. Yuan, J.G., Liu, X., Tang, Z.Q., 2001. Preliminarily study on the antimicrobial activity of olive and its functional compositions. Chinese Journal of Food Science, 22(3):82–84 (in Chinese).Google Scholar

Copyright information

© Zhejiang University 2008

Authors and Affiliations

  1. 1.Department of Biology, School of Life SciencesXiamen UniversityXiamenChina
  2. 2.Research Centre for Wetlands and Ecological EngineeringXiamen UniversityXiamenChina

Personalised recommendations