2D Heteronuclear (1H-13C) Single Quantum Correlation (HSQC) NMR Analysis of Norway Spruce Bark Components

Characterization of Lignocellulosic Materials

Volumn , Issue , 2009, Pages 1-16

  Zhang, Liming ^a   Gellerstedt, Göran ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

Condensed tannin purification; Milled bark tannin lignin; NMR identification; Norway spruce bark components 2D heteronuclear single quantum correlation (HSQC) NMR analysis; Solvent extraction; Solvent extractions and bark component separation; Stilbenes and tannins; Wood, pulp fibers, and paper novel and improved methods of characterization

Indexed keywords

EID: 84889449388     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781444305425.ch1     Document Type: Chapter

References (35)

1. Pizzi, A. and Scharfetter, H.J. (1978) The chemistry and development of tannin-based adhesives for exterior plywood. J. Appl. Polym. Sci. 22:1745.
2. Sakagami, H., Kuribayashi, N., Iida, M. et al. (1995) Induction of DNA fragmentation by tanninand lignin-related substances. Anticancer Res. 15:2121-2128.
3. Hagerman, A.E., Riedl, K.M., Jones, G.A. et al. (1998)High molecular weight plant polyphenolics (tannins) as biological antioxidants. J. Agric. Food Chem. 46:1887-1892.
4. Gil, M.I., Tomas-Barberan, F.A., Hess-Pierce, B., Holcroft, D.M., and Kader, A.A. (2000) Antioxidant activity of pomegranate juice and its relationship with phenolic composition and processing. J. Agric. Food Chem. 48:4581-4589.
5. Quideau, S., Jourdes, M., Lefeuvre, D. et al. (2005) The chemistry of wine polyphenolic C-glycosidic ellagitannins targeting human topoisomerase II. Chem. Eur. J. 11:6503-6513.
6. Afaq, F., Saleem, M., Krueger, C.G., Reed, J.D., and Mukhtar, H. (2005) Anthocyanin-and hydrolyzable tannin-rich pomegranate fruit extractmodulates MAPK and NF-κB pathways and inhibits skin tumorigenesis in CD-1 mice. Int. J. Cancer 113:423-433.
7. Malik, A., Afaq, F., Sarfaraz, S., Adhami, V.M., Syed, D.N., and Mukhtar, H. (2005) Pomegranate fruit juice for chemoprevention and chemotherapy of prostate cancer. PNAS 102:14813-14818.
8. Raghuraman, A., Tiwari, V., Thakkar, J.N. et al. (2005) Structural characterization of a serendipitously discovered bioactive macromolecule, lignin sulfate. Biomacromolecules 6:2822-2832.
9. von Alcubilla, M., Diaz-Palacio, M.P., Kreutzer, K., Laatsch, W., Rehfuess, R.E., and Denzel, G. (1971) Relation between nutrition and heart rot attack of Norway spruce (Picea abies) and the fungistatic effect of its inner bark. European J. For. Path. 1:100.
10. Mannila, E., Talvitie, A., and Kolehmainen, E. (1993) Anti-leukaemic compounds derived from stilbenes in Picea abies bark. Phytochemistry 33:813-816.
11. Merillon, J.-M., Fauconneau, B., Teguo, P.W., Barrier, L., Vercauteren, J., and Huguet, F. (1997) Antioxidant activity of the stilbene astringin, newly extracted from Vitis vinifera cell cultures. Clin. Chem. 43:1092-1093.
12. Waffo-Teguo, P., Hawthorne, M.E., Cuendet, M. et al. (2001) Potential cancer-chemopreventive activities od wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutrition Cancer 40:173-179.
13. Peltonen, S. (1981) Studies on bark extracts from Scots pine (Pinus sylvestris) and Norway spruce (Picea abies), Part 1. Main chemical composition. Pap. Puu 63:593-595.
14. Peltonen, S. (1981) Studies on bark extracts from Scots pine (Pinus sylvestris) and Norway spruce (Picea abies), Part 2. Chromatographic analysis of hot water and alkali soluble polyflavonoids. Pap. Puu 63:681-687.
15. Kylliainen, O. and Holmbom, B. (2004) Chemical composition of components in spruce waters. Pap. Puu 86:289-292.
16. Norin, T. and Winell, B. (1972) Extractives fromthe bark of common spruce, Picea abies L. Karst. Acta Chem. Scand. 26:2289-2296.
17. Björkman, A. (1956) Studies on finely divided wood. Part 1. Extraction of lignin with neutral solvents. Svensk Papperstidn. 59:477-485.
18. Theander, O. and Westerlund, E.A. (1986) Study on dietary fiber. Improved procedure for analysis of dietary fiber. J. Agric. Food Chem. 343:330-336.
19. Laouenan, P., Michon, V., Herve de Penhoat, C., Mila, I., and Scalbert, A. (1997) NMR structural investigations and conformational analysis of condensed tannins. A continuing challenge due to restricted rotation about the interflavanoid linkage. Analysis 25(8):M29-M32.
20. Mannila, E. and Talvitie, A. (1992) Stilbenes from Picea abies bark. Phytochemistry 31:3288-3289.
21. Dore, S. (2005) Unique properties of polyphenol stilbenes in the brain: more than direct antioxidant actions; gene/protein regulatory activity. Neurosignals 14:61-70.
22. Roupe, K.A., Remsberg, C.M., Yanez, J.A., and Davies, N.M. (2006) Pharmacometrics of stilbenes: seguing towards the clinic. Curr. Clin. Pharmacol. 1:81-101.
23. Ferreira, D. and Li, X.-C. (2000) Oligomeric proanthocyanidins: naturally occurring O-heterocycles. Nat. Prod. Rep. 17:193-212.
24. Shen, C.-C., Chang Y.-S., and Ho, L.-K. (1993) Nuclear magnetic resonance studies of 5,7-dihydroxyflavonoids, Phytochemistry 34:843-845.
25. Pan, H. and Lundgren, L.N. (1995) Phenolic extractives from root bark of Picea abies. Phytochemistry 39:1423-1428.
26. Khan, M.L., Haslam, E., and Williamson, M.P. (1997) Structure and conformation of the procyanidin B-2 dimer. Magn. Res. Chem. 35:854-858.
27. De Bruyne, T., Pieters, L.A.C., Dommisse, R.A. et al. (1996) Unambiguous assignments for free dimeric proanthocynidin phenols from 2D NMR. Phytochemistry 43:265-272.
28. Saito, A., Nakajima, N., Tanaka, A., and Ubukata, M. (2002) Synthesis study of proanthocyanidins. Part 2: Stereoselective gram-scale synthesis of procyanidin-B3. Tetrahedron 58:7829-7837.
29. Behrens, A., Maie, N., Knicker, H., and 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 62:1159-1170.
30. Ohyama, M., Tanaka, T., and Iinuma, M. (1995) Five resveratrol oligomers from roots of Sophora leachiana. Phytochemistry 38:733-740.
31. Waffo-Teguo, P., Lee, D., Cuendet, M., Merillon J.-M., Pezzuto, J.M., and Kinghorn, D. (2001) Two new stilbene dimer glucosides from grape (Vitis vinifera) cell cultures. J. Nat. Prod. 64:136-138.
32. Zhang, L., Henriksson, G., and Gellerstedt, G. (2003) The formation of β-β structures in lignin biosynthesis - are there two different pathways? Org. Biomol. Chem. 1:3621-3624.
33. Ralph, J., Marita, J., Ralph, S.A. et al. (1999) Solution-State NMR of Lignins. In D.S. Argyropoulos (Ed.) Advances in Lignocellulosics Characterization. TAPPI Press, Atlanta, GA, pp. 55-108.
34. Steyberg, J.P., Ferreira, D., and Roux, D.G. (1983) The first condensed tannins based on a stilbene. Tetrahedron Lett. 24:4147-4150.
35. Waffo-Teguo, P., Decendit, A., Krisa, S., Deffieux, G., Vercauteren, J., and Merillon J.-M. (1996). The accumulation of stilbene glycosides in Vitis vinifera cell suspension culture. J. Nat. Prod. 59:1189-1191.