Study on the Structure of Mangrove Polyflavonoid Tannins with MALDI-TOF Mass Spectrometry and NMR

Abstract:

The properties of polyflavonoid tannins from the mangrove species depend on their structure in terms of monomer units, their mean degree of polymerization and the linkage-type between flavan-3-ol units with a considerable range of structural variation. Polyflavonoid tannins were characterized by matrix-assisted laser desorption/ionization time of flight mass spectrometry (MALDI-TOF MS), which were too difficult to be resolved by other techniques. MALDI-TOF mass spectra of polyflavonoid tannins of four mangrove species in Rhizophoraceae, Kandelia candel, Ceriops tagal, Bruguiera cylindrica and Rhizophora apiculata showed as follows: (1) procyanidin oligomers formed by catechin/epicatechin, and catechin-3-O-rhamnoside monomers were present in great proportions; epigallocatechin and epicatechin gallate monomers were not detected; (2) the doubly linked structure of A-type procyanidins were also evident from the mass spectra of K. candel; (3) there were major differences in polyflavonoid tannin structure among mangrove species; and (4) the distribution of tannin oligomers, and the number-average degree of polymerization obtained by MALDI-TOF MS appeared to compare well with the results obtained by 13C nuclear magnetic resonance (NMR) analysis.

• Periodical: Advanced Materials Research (Volumes 554-556)
• Pages: 1988-1993
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.554-556.1988
• Online since: July 2012
• Authors: Liang Liang Zhang, Yong Mei Wang, Dong Mei Wu, Man Xu, Jia Hong Chen
• Keywords: MALDI-TOF, Mangrove, Mass Spectrometry, NMR, Polyflavonoids

References

[1] E. Haslam. Plant Polyphenols, Cambridge University Press, Cambridge, UK. (1989)

[2] L.J. Porter, in: The Flavonoids, Advances in Research Since 1980, edited by J.B. Harborne, Chapman and Hall, New York, (1988), p.21

[3] J.J. Karchesy and R.W.J. Hemingway. J. Agric. Food Chem. 34 (1986) 966-970

[4] P.J. Hernes, R. Benner, G.L. Cowie, M.A. Goni, B.A. Bergamaschi and J.I. Hedges. Geochim. Cosmochim. Acta. 65 (2001) 3109-3122

[5] K. McKee and I. Feller. NOAA, Silver Spring, MD, (1995)

[6] I.C. Feller, D. Whigham, J. O'Neill and K. McKee. Ecology, 80 (1999) 2193-2205

[7] J. Mainoya, S. Mesaki and F.F. Banyikwa. in: Man in the mangroves: the socio-economic situation of human settlements in mangrove forests, edited by P.E. Kunstadter, C.F. Bird and S. Sabhasri, United Nations University, Tokyo, (1986), pp.87-95

DOI: 10.2307/2057387

[8] M. Martínez. Las Plantas Medicinales de Mexico, Ediciones Botas, Mexico City, (1969)

[9] H. Pittier. Manual de las Plantas Usuales de Venezuela, Fundación Eugenio Mendoza, Caracas, (1978)

[10] R. Lemmens, N and Wilijarni-Soetjipto. Dye and tannin-producing plants, Pudoc, Wageningen, (1991)

[11] D. Banerjee, S. Chakrabarti, A.K. Hazra, S. Banerjee, J. Ray and B. Mukherjee. Afr. J. Biotechnol. 7 (2008) 805-810

[12] M. Noferi, E. Masson, A. Merlin, A. Pizzi and X. Deglise. J. Appl. Polym. Sci. 63 (1997) 475-482

DOI: 10.1002/(sici)1097-4628(19970124)63:4<475::aid-app9>3.0.co;2-o

[13] C.A. Rice-Evans, N.J. Miller and G. Paganga. Free Radical Bio. Med. 20 (1996) 933-956

[14] A.A. Rahim, E. Rocca, J. Steinmetz, M.J. Kassim, R. Adnan and M. Sani Ibrahim. Corrosion Sci. 49 (2007) 402-417

DOI: 10.1016/j.corsci.2006.04.013

[15] H. Pasch, A. Pizzi and K. Rode. Polymer, 42 (2001) 7531-7539

[16] P. Xiang, Y.M. Lin, P. Lin and C. Xiang. Chinese J. Anal. Chem. 34 (2006) 1019-1022

[17] L.L. Zhang and Y.M. Lin. J. Zhejiang Univ. Sci. B. 9 (2008) 407-415

[18] H. Hedqvist, I. Mueller-Harvey, J.D. Reed, C.G. Krueger and M. Murphy. Anim. Feed Sci. Technol. 87 (2000) 41-56

[19] P. Xiang, Y.M. Lin, P. Lin, C. Xiang, Z.W. Yang and Z.M. Lu. J. Appl. Polymer Sci. 105(2007) 859-864