Journal of Zhejiang University SCIENCE B
ISSN 1673-1581(Print), 1862-1783(Online), Monthly
2008 Vol. 9 No. 5 p. 407~415
On-line Access Date: May 20, 2008Tannins from Canarium album with potent antioxidant activity
Liang-liang ZHANG1, Yi-ming LIN†‡1,2
(1Department of Biology, School of Life Sciences, Xiamen University, Xiamen 361005, China)
(2Research Centre for Wetlands and Ecological Engineering, Xiamen University, Xiamen 361005, China)
‡ Corresponding Author
†E-mail: linym@xmu.edu.cn
Received Jan. 1, 2008; revision accepted Mar. 18, 2008
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 tannins 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)
doi:10.1631/jzus.B0820002 CLC number: Q946.84
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.
[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.
[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.
[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.
[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.
[6] Ding, B.P., 1999. Pharmacology of Qingguo pills on relieving cough. China Traditional Patent Medicine, 21:27-28 (in Chinese).
[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.
[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.
[9] Haslam, E., 1998. Practical Polyphenolics: From Structure to Molecular Recognition and Physiological Action. Cambridge University Press, Cambridge, p.422.
[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.
[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.
[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.
[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.
[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.
[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.
[16] Oszmianski, J., Wojdylo, A., Lamer-Zarawska, E., Swiader, K., 2007. Antioxidant tannins from Rosaceae plant roots. Food Chemistry, 100(2):579-583.
[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.
[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.
[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.
[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.
[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.
[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).
[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.
[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.
[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.
[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.
[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).