Fast Atom Bombardment Mass Spectrometry of Condensed Tannin Sulfonate Derivatives


  • J. J. Karchesy
  • L. Y. Foo
  • R. W. Hemingway
  • E. Barofsky
  • D. F. Barofsky


Condensed tannins, sulfonate derivatives, fast atom bombardment, mass spectrometry, bark chemicals


Condensed tannin sulfonate derivatives were studied by fast atom bombardment mass spectrometry (FAB-MS) to assess the feasibility of using this technique for determining molecular weight and structural information about these compounds. Both positive- and negative-ion spectra provided useful data with regard to molecular weight, cation species present, and presence of the sulfonate moiety. Additional structural information was provided in the spectra of the dimer sulfonates by fragment ions resulting from retro-Diels Alder fission and cleavage of the interflavanoid bond. Overall, negative-ion spectra proved to be superior to positive-ion spectra because of less interference from matrix ions. FAB-MS holds promise as a technique for analyzing condensed tannin sulfonates yet to be isolated and will help facilitate development of new adhesives made with these compounds.


Barber, M., R. S. Bordoli, G. J. Elliott, R. D. Sedgwick, and A. N. Taylor. 1982. Fast atom bombardment mass spectrometry. Anal. Chem. 54: 645-657.nBurlingame, A. L., T. A. Baillie, and P. J. Derrick. 1986. Mass spectrometry. Anal. Chem. 58: 165R-211R.nDeKoster, C. G., W. Heerma, G. Dijkstra, and G. J. Niemann. 1985. Fast atom bombardment of flavonols. Biomed. Mass Spectrom. 12: 596-601.nFoo, L. Y., G. W. McGraw, and R. W. Hemingway. 1983. Condensed tannins: Preferential substitution at the interflavanoid bond by sulfite ion. J. Chem. Soc., Chem. Commun. 12: 672-673.nHaslam, E. 1982. Proanthocyanidins. Pages 417-447 in J. B. Harborne and T. J. Mabry, eds. The flavanoids: Advances in research. Chapman and Hall, London.nHemingway, R. W., and R. C. Lloyd. 1982. Economic prospects for conifer bark extracts. Final rept. 50-3201-47. USDA For. Serv., South. For. Exp. Stn., Pineville, LA.nKarchesy, J. J., R. W. Hemingway, Y. L. Foo, E. Barofsky, and D. F. Barofsky. 1986. Sequencing procyanidin oligomers by fast atom bombardment mass spectrometry. Anal. Chem. 58: 2563-2567.nKreibich, R. E., and R. W. Hemingway. 1987. Condensed tannin-sulfonate derivatives in cold-setting wood-laminating adhesives. Forest Prod. J. 37(2): 43-46.nLaks, P. E., and R. W. Hemingway. 1987. Condensed tannins: Base-catalyzed reactions of polymeric procyanidins with toluene-α-thiol. Lability of the interflavanoid bond and pyran ring. J. Chem. Soc. Perkin Trans. 1: 465-470.nMabry, T. J., and K. R. Markham. 1975. Mass spectrometry of flavonoids. Pages 78-126 in J. B. Harborne, T. J. Mabry, and H. Mabry, eds. The flavonoids, part 1. Academic Press, NY.nMcGraw, G. W., P. E. Laks, and R. W. Hemingway. 1988. Condensed tannins: Desulfonation of hydroxybenzyl sulfonic acids related to proanthocyanidin derivatives. J. Wood Chem. Tech. 8(1): 91-109.nMonaghan, J. J., M. Barber, R. S. Bardoli, R. D. Sedgwick, and A. N. Tyler. 1982a. Fast atom bombardment mass spectra of involatile sulphonated azo dyestuffs. Org. Mass Spectrom. 17: 569-574.nMonaghan, J. J., M. Barber, R. S. Bardoli, R. D. Sedgwick, and A. N. Tyler. 1982b. Fast atom bombardment mass spectra of involatile naphthalene sulphonic acids and sulphonate salts. Org. Mass Spectrom. 17: 529-533.nWilliams, V. M., L. J. Porter, and R. W. Hemingway. 1983. Molecular weight profiles of proanthocyanidin polymers. Phytochemistry 22(2): 569-572.n






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