The aim of this work was to determine
the structural characteristics of the condensed tannins isolated from the
aqueous extract of black spruce (Picea
mariana Mill) bark. This is the first report on the structural
characterization of condensed tannins from black spruce bark. The condensed
tannins from the hot water extract prepared from Picea mariana bark were isolated by column chromatography on
Sephadex LH-20 media. In this study, UV-visible and 13C-NMR spectroscopic techniques, along with pyrolysis-gas
chromatography/mass spectrometry (Py-GC/MS) and liquid chromatogramphy analyses were applied to determine the
structural characteristics of black spruce bark tannins. We have confirmed for
the first time the presence of methoxylated B-rings in the flavanol units of
condensed tannins from black spruce bark, which could be regarded as further
contribution to the chemotaxonomy of the genus Picea. The methoxylation of Norway spruce bark condensed tannins have been demonstrated previously.
Cite this paper
P. Diouf, C. Tibirna, M. García-Pérez, M. Royer, P. Dubé and T. Stevanovic, "Structural Elucidation of Condensed Tannin from Picea mariana Bark," Journal of Biomaterials and Nanobiotechnology, Vol. 4 No. 3, 2013, pp. 1-8. doi: 10.4236/jbnb.2013.43A001.
 G. D. Manners and E. P. Swan, “Stilbenes in Barks of 5 Canadian Picea Species,” Phytochemistry, Vol. 10, No. 3, 1971, pp. 607-610. doi:10.1016/S0031-9422(00)94705-8
 E. Anderson and W. W. A. Pigman, “A Study of the Inner Bark and Cambial Zone of Black Spruce (Piceamariana BSP),” Science, Vol. 105, No. 2736, 1947, pp. 601-602.
 W. Pigman, E. Anderson, R. Fischer, M. A. Buchanan and B. L. Browning, “Color Precursors in Spruce Wood and Western Hemlock Woods and Inner Barks,” Tappi, Vol. 36, No. 4, 1953, pp. 4-12.
 P. N. Diouf, T. Stevanovic and A. Cloutier, “Study on Chemical Composition, Antioxidant and Anti-Inflammatory Activities of Hot Water Extract from Picea mariana Bark and Its Proanthocyanidin-Rich Fractions,” Food Chemistry, Vol. 113, No. 4, 2009, pp. 897-902.
 M.-E. García-Pérez, M. Royer, A. Duque-Fernandez, P. N. Diouf, T. Stevanovic and R. Pouliot, “Antioxidant, Toxicological and Antiproliferative Properties of Canadian Polyphenolic Extracts on Normal and Psoriatic Keratinocytes,” Journal of Ethnopharmacology, Vol. 132, No. 1, 2010, pp. 251-258. doi:10.1016/j.jep.2010.08.030
 P. Schofield, D. M. Mbugua and A. N. Pell, “Analysis of Condensed Tannins: A Review,” Animal Feed Science and Technology, Vol. 91, No. 1-2, 2001, pp. 21-40.
 A. Yanagida, T. Shoji and Y. Shibusawa, “Separation of Proanthocyanidins by Degree of Polymerization by Means of Size-Excluzion Chromatography and Related Techniques,” Journal of Biochemical and Biophysical Methods, Vol. 56, No. 1-3, 2003, pp. 311-322.
 M. Karonen, J. Loponen, V. Ossipov and K. Pihlaja, “Analysis of Procyanidins in Pine Bark with ReversedPhase and Normal Phase High-Performance Liquid Chromatography-Electrospray Ionization Mass Spectrometry,” Analytica Chimica Acta, Vol. 522, No. 1, 2004, pp. 105112. doi:10.1016/j.aca.2004.06.041
 L. P. Meagher, G. Lane, S. Sivakumaran, M. H. Tavendale and K. Fraser, “Characterization of Condensed Tannins from Lotus Species by Thiolytic Degradation and Electrospray Mass Spectrometry,” Animal Feed Science and Technology, Vol. 117, No. 1-2, 2004, pp. 151-163.
 N.-E. Es-Safi, S. Guyot and P.-H. Ducrot, “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, Vol. 54, No. 19, 2006, pp. 969-977.
 P. Navarrete, A. Pizzi, H. Pasch, K. Rode and L. Delmotte, “MALDI-TOF and 13C NMR Characterization of Maritime Pine Industrial Tannin Extract,” Industrial Crops and Products, Vol. 32, No. 2, 2010, pp. 105-110.
 F. H. Romer, A. P. Underwood, N. D. Senekal, S. L. Bonnet, M. J. Duer, D. G. Reid and J. H. van der Westhuizen, “Tannin Fingerprinting in Vegetable Tanned Leather by Solid State NMR Spectroscopy and Comparison with Leathers Tanned by Other Processes,” Molecules, Vol. 16, No. 2, 2011, pp. 1240-1252.
 L. J. Porter, L. N. Hrstich and B. G. Chan, “The Conversion of Proanthocyanidins and Delphinidins to Cyanidin and Delphinidin,” Phytochemistry, Vol. 25, No. 1, 1986, pp. 223-230. doi:10.1016/S0031-9422(00)94533-3
 Z. Czochanska, L. Y. Foo, R. H. Newman and L. G. Porter, “Polymeric Proanthocyanidins. Stereochemistry, Structural Units, and Molecular Weight,” Journal of the Chemical Society, Perkin Transactions 1, 1980, pp. 22782286. doi:10.1039/p19800002278
 K. Lorenz and C. M. Preston, “Characterization of HighTannin Fractions from Humus by Carbon-13 Cross-Polarization and Magic-Angle Spinning Nuclear Magnetic Resonance,” Journal of Environmental Quality, Vol. 31, No. 2, 2002, pp. 431-436. doi:10.2134/jeq2002.0431
 S. Ohara, Y. Yasuta and H. Ohi, “Structure Elucidation of Condensed Tannins from Barks by Pyrolysis/Gas ChroMatography,” Holzforschung, Vol. 57, No. 2, 2003, pp. 145-149. doi:10.1515/HF.2003.023
 R. J. Robbins, J. Leonczak, J. C. Johnson, J. Li, C. Kwik-Uribe, R. L. Prior and L. Gu, “Method Performance and Multi-Laboratory Assessment of a Normal Phase High Pressure Liquid Chromatography-Fluorescence Detection Method for the Quantitation of Flavanols and Procyanidins in Cocoa and Chocolate Containing Samples,” Journal of Chromatography A, Vol. 1216, No. 24, 2009, pp. 4831-4840. doi:10.1016/j.chroma.2009.04.006
 W. Heller and G. Forkmann, “Biosynthesis of Flavonoids,” In: J. B. Harborne, Ed., The Flavonoids: Advances in Research Since 1986, Chapman and Hall, London, 1993, pp. 499-535.
 L. Hussein, M. A. Fattah and E. Salem, “Characterization of Pure Proanthocy-anidins Isolated from the Hulls of Faba Beans,” Journal of Agricultural and Food Chemistry, Vol. 38, No. 1, 1990, pp. 95-98.
 L. Zhang and G. Gellerstedt, “2D Heteronuclear (1H-13C) Single Quantum Correlation (HSQC) NMR Analysis of Norway Spruce Bark Components,” In: T. Q. Hu, Ed., Characterization of Lignocellulosic Materials, Blackwell, Oxford, 2008, pp. 3-6. doi:10.1002/9781444305425.ch1
 H. Pan and L. N. Lundgren, “Phenolic Extractives from Root Bark of Piceaabies,” Phytochemistry, Vol. 39, No. 6, 1995, pp. 1423-1428.
 G. C. Galletti and A. Antonelli, “The Potential of Pyrolysis-(methylation)/Gas Chromatography/Mass Spectrometry in the Analysis of Wine Polyphenolics,” Rapid Communications in Mass Spectrometry, Vol. 7, No. 7, 1993, pp. 656-658. doi:10.1002/rcm.1290070720
 L. M. de Souza, T. R. Cipriani, M. Iacomini, P. A. J. Gorin and G. L. Sassaki, “HPLC/ESI-MS and NMR Analysis of Flavonoids and Tannins in Bioactive Extract from Leaves of Maytenus ilicifolia,” Journal of Pharmaceutical and Biomedical Analysis, Vol. 47, No. 1, 2008, pp. 59-67. doi:10.1016/j.jpba.2007.12.008