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Fractionation of Grape Seed Proanthocyanidins for Bioactivity Assessment

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The Biological Activity of Phytochemicals

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 41))

Abstract

Grape seed extract (GSE) is rich in flavonoids, particularly proanthocyanidins (PAs). PAs and their monomers are strong antioxidants and have been ascribed a number of potential activities beneficial to health, including protection against cancers, cardiovascular disease, and Alzheimer’s disease. However, little is known about the chemical nature and the concentration of bioactive polyphenols to which the body is exposed after ingestion of GSE. This chapter summarizes recent advances in fractionation techniques for PAs, including work from our laboratory on fractionation of GSE in quantities sufficient for analysis of its protective effects in whole animal models of Alzheimer’s disease. Several techniques, ranging from fractionation using liquid–liquid extraction to separation on Toyopearl resin and normal-phase HPLC, have been optimized to separate and purify monomeric, oligomeric, and polymeric PAs from GSE. The extraction and separation efficiencies of the various techniques are discussed.

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References

  1. Xie DY, Dixon RA (2005) Proanthocyanidin biosynthesis-still more questions than answers? Phytochemistry 66:2127–2144

    Article  CAS  PubMed  Google Scholar 

  2. Vidal SFL, Francis L, Guyot S et al (2003) The mouth-feel properties of grape and apple proanthocyanidins in a wine-like medium. J Sci Food Agric 83:564–573

    Article  CAS  Google Scholar 

  3. Okello EJ, Savelev SU, Perry EK (2004) In vitro anti-beta-secretase and dual anti-cholinesterase activities of Camellia sinensis L. relevant to treatment of dementia. Phytother Res 18:624–627

    Article  PubMed  Google Scholar 

  4. Wang J, Ho L, Zhao W et al (2008) Grape-derived polyphenolics prevent Aβ oligomerization and attenuate cognitive deterioration in a mouse model of Alzheimer’s disease. J Neurosci 28:6388–6392

    Article  CAS  PubMed  Google Scholar 

  5. Ricardo DS, Darmon N, Fernandez Y et al (1991) Oxygen free radical scavenger capacity in aqueous models of different procyanidins from grape seeds. J Agric Food Chem 39:1549–1552

    Article  Google Scholar 

  6. Ono K, Yoshiike Y, Takashima A et al (2003) Potent anti-amyloidogenic and fibril-destabilizing effects of polyphenols in vitro: implications for the prevention and therapeutics of Alzheimer’s disease. J Neurochem 87:172–181

    Article  CAS  PubMed  Google Scholar 

  7. Porat Y, Abramowitz A, Gazit E (2006) Inhibition of amyloid fibril formation by polyphenols: structural similarity and aromatic interactions as a common inhibition mechanism. Chem Biol Drug Des 67:27–37

    Article  CAS  PubMed  Google Scholar 

  8. Sun B, Leandro C, Ricardo JM (1998) Separation of grape and wine proanthocyanidins according to their degree of polymerization. J Agric Food Chem 46:1390–1396

    Article  CAS  Google Scholar 

  9. Ricardo DS, Rigaud JM, Cheynier V et al (1991) Procyanidin dimers and trimers from grape seeds. Phytochemistry 30:1259–1264

    Article  Google Scholar 

  10. Saucier C, Mirabel M, Daviaud F et al (2001) Rapid fractionation of grape seed proanthocyanidins. J Agric Food Chem 49:5732–5735

    Article  CAS  PubMed  Google Scholar 

  11. Rigaud J, Escribano-Bailon MT, Prieur C et al (1993) Normal phase high performance liquid chromatographic separation of procyanidins from cacao beans and grape seeds. J Chromatogr 654:255–260

    Article  CAS  Google Scholar 

  12. Kolodziej H (1985) Fractionation of condensed tannins by counter current chromatography. J Chromatogr 318:85–93

    Article  Google Scholar 

  13. Giner-Chavez BI, Van Soest PJ, Robertson JB et al (1997) A method for isolating condensed tannins from crude plant extracts with trivalent ytterbium. J Sci Food Agric 74:359–368

    Article  CAS  Google Scholar 

  14. Cheynier V, Doco T, Fulcrand H et al (1997) ESI-MS analysis of polyphenolic oligomers and polymers. Analysis 25:32–37

    Google Scholar 

  15. Silva JMR, Rigaud J, Cheynier V et al (1991) Procyanidin dimers and trimers from grape seeds. Phytochemistry 30:1259–1264

    Article  Google Scholar 

  16. Prieur C, Rigaud J, Cheynier V et al (1994) Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry 36:781–784

    Article  CAS  Google Scholar 

  17. Sun B, Belchior P, Ricardo-da-Silva JM et al (1999) Isolation and purification of dimeric and trimeric procyanidins from grape seeds. J Chromatogr A 841:115–121

    Article  CAS  Google Scholar 

  18. Gabetta B, Fuzzati N, Griffini A et al (2000) Characteriztion of proanthocyanidins from grape seeds. Fitoterapia 71:162–175

    Article  CAS  PubMed  Google Scholar 

  19. Yang Y, Chien M (2000) Characterization of grape procyanidins using high performance liquid chromatography/mass spectrometery and matrix assisted laser desorption/ionization time of flight mass spectrometry. J Agric Food Chem 48:3990–3996

    Article  CAS  PubMed  Google Scholar 

  20. Kennedy JA, Hayasaka Y, Vidal S et al (2001) Composition of grape skin proanthocyanidins at different stages of berry development. J Agric Food Chem 49:5348–5355

    Article  CAS  PubMed  Google Scholar 

  21. Labarbe B, Cheynier V, Brossaud F et al (1999) Quantitative fractionation of grape proanthocyanidins according to their degree of polymerization. J Agric Food Chem 47:2719–2723

    Article  CAS  PubMed  Google Scholar 

  22. Sun B, Spranger MI, Ricardo-da-Silva JM (1996) Extraction of grape seed procyanidins using different organic solvents. In: Vercauteren J, Cheze C, Dumon MC, Weber JF (eds) Proceedings of the 18th International Conference on Polyphenols. Groupe Polyphénols, Bordeaux (France)

    Google Scholar 

  23. Sun B, Spranger MI (2005) Review: quantitative extraction and analysis of grape and wine proanthocyanidins and stilbenes. Ciencia Tec Vitiv 20:59–89

    Google Scholar 

  24. Jing H, Deinzer ML (2007) Tandem mass spectrometry for sequencing proanthocyanidins. Anal Chem 79:1739–1748

    Article  Google Scholar 

  25. Kennedy JA, Jones GP (2001) Analysis of proanthocyanidin cleavage products following acid-catalysis in the presence of excess phloroglucinol. J Agric Food Chem 49:1740–1746

    Article  CAS  PubMed  Google Scholar 

  26. Derdelinckx G, Jerumanis J (1984) Separation of malt hop proanthocyanidins on Fractogel TSK HW-40(S). J Chromatogr 285:231–244

    Article  CAS  Google Scholar 

  27. Price ML, Butler LG (1977) Rapid visual estimation and spectrophotometric determination of tannin content of sorghum grain. J Agric Food Chem 25:1268–1273

    Article  CAS  Google Scholar 

  28. Graham HD (1992) Stabilization of the Prussian blue color in the determination of polyphenols. J Agric Food Chem 40:801–805

    Article  CAS  Google Scholar 

  29. Scalbert A (1992) Quantitative methods for the estimation of tannins in plant tissues. In: Hemingway RW, Laks PE (eds) Plant polyphenols: synthesis, properties, significance, vol 59. Plenum Press, New York, NY, pp 259–280

    Google Scholar 

  30. Broadhurst RB, Jones WT (1978) Analysis of condensed tannins using acidified vanillin. J Sci Food Agr 29:788–794

    Article  CAS  Google Scholar 

  31. McMurrough I, McDowell J (1978) Chromatographic separation and automated analysis of flavanols. Anal Biochem 91:92–100

    Article  CAS  PubMed  Google Scholar 

  32. Butler LG, Price ML, Brotherton JE (1982) Vanillin assay for proanthocyanidins (condensed tannins): modification of the solvent for estimation of the degree of polymerization. J Agric Food Chem 30:1087–1089

    Article  CAS  Google Scholar 

  33. Makkar HPS, Becker K (1993) Vanillin-HCl method for condensed tannins: effect of organic solvents used for extraction of tannins. J Chem Ecol 19:613–621

    Article  CAS  Google Scholar 

  34. Thies M, Fischer R (1971) A new colour reaction for the microchemical detection and the quantitative determination of catechins. Mikrochim Acta 1:9–13

    Article  Google Scholar 

  35. Treutter D (1989) Chemical reaction detection of catechins and proanthocyanidins with 4-dimethylaminocinnamaldehyde. J Chromatogr 467:185–193

    Article  CAS  Google Scholar 

  36. Nagel CW, Glories Y (1991) Use of a modified dimethylaminocinnamaldehyde reagent for analysis of flavanols. Am J Enol Vitic 42:364–366

    CAS  Google Scholar 

  37. Guyot S, Doco T, Souquet JM et al (1997) Characterization of highly polymerized procyanidins in cider apple skin and pulp. Phytochemistry 44:351–357

    Article  CAS  Google Scholar 

  38. Peel GJ, Dixon RA (2007) Detection and quantification of engineered proanthocyanidins in transgenic plants. Nat Prod Commun 2:1009–1014

    CAS  Google Scholar 

  39. Mathews S, Mila I, Scalbert A et al (1997) Method for estimation of proanthocyanidins based on their acid depolymerization in the presence of nucleophiles. J Agric Food Chem 45:1195–1201

    Article  Google Scholar 

  40. Hermingway RW (1989) Reactions at the interflavanoid bond of proanthocyanidins. In: Hermingway RW, Karchesy JJ (eds) Chemistry and significance of condensed tannins. Plenum Press, New York, NY

    Google Scholar 

  41. Kohler N, Wray V, Winterhalter P (2008) Preparative isolation of procyanidins from grape seed extracts by high-speed counter-current chromatography. J Chromatogr A 1177:114–125

    Article  CAS  PubMed  Google Scholar 

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Acknowledgments

We thank David Huhman for assistance with mass spectrometry analysis. This work was supported by the National Institutes of Health National Center for Complementary and Alternative Medicine (award # 1 PO1 AT004511) and the Samuel Roberts Noble Foundation.

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Correspondence to Richard A. Dixon .

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Sharma, V., Zhang, C., Pasinetti, G.M., Dixon, R.A. (2011). Fractionation of Grape Seed Proanthocyanidins for Bioactivity Assessment. In: Gang, D. (eds) The Biological Activity of Phytochemicals. Recent Advances in Phytochemistry, vol 41. Springer, New York, NY. https://doi.org/10.1007/978-1-4419-7299-6_3

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