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Ciência e Técnica Vitivinícola

versão impressa ISSN 0254-0223

Ciência Téc. Vitiv. v.20 n.2 Dois Portos  2005

 

REVIEW: QUANTITATIVE EXTRACTION AND ANALYSIS OF GRAPE AND WINE PROANTHOCYANIDIN AND STILBENES

 

Baoshan Sun1, M. Isabel Spranger1

 

1Estação Vitivinícola Nacional, Instituto Nacional de Investigação Agrária e das Pescas, 2565-191 Dois Portos, Portugal. E-mail: inia.evn.quim@oninet.pt

(Manuscrito recebido em 16.09.05. Aceite para publicação em 14.11.05.)

 

 

SUMMARY

From the point of view of biological importance, proanthocyanidins (condensed tannins) and stilbenes (1,2-diarylethenes) are the two most important classes of polyphenols in grape and wine, which have attracted considerable attention of the international scientific community during the last fifteen years, due essentially to their potential beneficial health effects, related to their protective action towards cardiovascular disease and the oxygen free radical scavenger capacity. Numerous research works on proanthocyanidins and stilbenes have been published, but the majority of them have focused on the structural identification and biological activities of these compounds. Furthermore, less attention has been paid on their quantitative aspects and few analytical methods have been validated. This paper introduces briefly grape and wine proanthocyanidins and stilbenes and presents some works realized in our laboratory concerning quantitative extraction and analysis of these compounds.

Key words: grape, wine, proanthocyanidins, stilbenes, extraction, analysis.

 

 

RESUMO

Revisão: extracção e análise quantitativa de proantocianidinas e estilbenos da uva e do vinho

Do ponto de vista de importância biológica, as proantocianidinas (taninos condensados) e os estilbenos (1,2-diarilletenos) são as duas classes de polifenóis mais importantes na uva e no vinho, o que tem chamado a muito atenção da comunidade científica internacional durante os últimos 15 anos, devido essencialmente aos potenciais efeitos benéficos destes compostos para a saúde humana, relativamente à sua acção protectiva contra a doença cardiovascular e a sua capacidade de captar radicais livres de oxigénio. Numerosos trabalhos de investigação sobre as proantocianidinas e os estilbenos foram publicados, mas a maior parte deles têm incidido na identificação estrutural e nas actividades biológicas destes compostos. Porém, pouca atenção tem sido dispensada aos aspectos quantitativos e poucos métodos analíticos têm sido validados. Este artigo apresenta uma breve introdução sobre as proantocianidinas e os estilbenos da uva e do vinho e trabalhos realizados no nosso laboratório relativamente à extracção e análise quantitativa destes compostos.

Palavras chave: uva, vinho, proantocianidinas, estibenos, extracção, análise.

 

RÉSUMÉ

Revue bibliographique: extraction et analyse quantitative des proanthocyanidines et des stilbenes du rasin et du vin

Du point de vue de l’importance biologique, les proanthocyanidines (tannins condensés) et les stilbènes (1,2-diarylethenes) sont les deux classes de polyphénols les plus importantes du rasin et du vin, qui ont fait beaucoup retenu l’ attention de la communauté scientifique internationale pendant les dernières 15 années, principalement à cause des effets bénéfiques pour la santé humaine, relativement à leur action protective contre les maladies cardiovasculaires et à leur capacité de capture des radicaux libres de oxygènés. Bien que beaucoup de travaux scientifiques ont été publiés, le plupart de ces travaux ont été realisés sur l’identification structurale et les activités biologiques de ces composés. Peu attention a été prise sur l’aspect quantitatif et peu de méthodes analytiques ont été validées. Cet article présente en une brève introduction les connaissances actualisées sur les proanthocyanidines et les stilbenes du rasin et du vin, ainsi que les travaux réalisés dans notre laboratoire sur l’extraction et l’analyse quantitative de ces composés.

 

 

Texto completo disponível apenas em PDF.

Full text only available in PDF format.

 

 

REFERENCES

Adrian M., Jeandet P., Bessis R., Joubert J.M., 1996. Induction of Phytoalexin (resveratrol) synthesis in grapevine leaves treated with aluminum chloride (AlCl3). J. Agric. Food Chem. 44, 1979-1981.         [ Links ]

Adrian M., Jeandet P., Breuil A.C., Levite D., Debord S., Bessis R., 2000. Assay of resveratrol and derivative stilbenes in wines by direct injection high performance liquid chromatography. Am. J. Enol. Vitic., 51 (1), 37 – 41.

Amrani-Joutei K., Glories Y., Mercier M., 1994. Localisation des tanins dans la pellicule de baie de raisin. Vitis, 33, 133-138.

Asquith T.N., Butler L.G., 1985. Use of dye-labeled protein as spectrophotometric assay for protein precipitants such as tannin. J. Chem. Ecology, 11, 1535-1544.

Aubert S., Poux C., 1969. Extraction des composés phénoliques du raisin. Ann. Technol. Agric., 18 (2), 93-109.

Bais A.J., Murphy P.J., Dry I.B., 2000. The molecular regulation of stilbene phytoalexin biosynthesis in Vitis vinifera during grape berry development. Am. J. Plant Physiol., 27, 425-433.

Bavaresco L., Cante E., Fregoni M., Trevisan M., 1997. Constitutive stibene contents of grapevine cluster stems as potential source of resveratrol in wine. Vitis, 36 (3): 115-118.

Bavaresco L., Pezzutto S., Ragga A., Ferrari F., Trevisan M., 2001. Effect of nitrogen supply on trans-resveratrol concentration in berries of Vitis vinífera L. cv. Cabernet Sauvignon. Vitis, 40, 229-230.

Bessis R., Blache D., Jeandet P., Adrian M., Meunier P., Breuil A.C., Pirio N., 1998. Un polyphénol remarqué : le resveratrol. Porquoi ? In : Guide Vins et Santé. Les Editions du Voyage. Institut Européen de recherche et de communication sur le vin, la société et la santé, pp 61-73.

Bessis R., Jeandet P., Adrian M., Breuil A.C., Debord S., 1997. resvératrol, défenses naturelles de la vingne et image santé du vin. Revue des Oenologues, 85, 5-8.

Blond J.P., Denis M.P., Bezaed J., 1995. Action antioxydante du resvératrol sur la lipoperoxydation. Sciences des Aliments, 15, 347-358.

Boukharta M., 1988. Etude des flavanoïdes de Vitis vinifera: structure des proanthocyanidines des pépins de raisin, de sarments et de feuilles de vigne. PhD. Thesis, INPL, Lorraine, Nancy.

Boukharta M., Girardin M., Metche M., 1988. Procyanidines galloylées du sarment de vigne (Vitis vinifera). Séparation et identification par chromatographie liquide haute performance and chromatographie en phase gazeuse. J Chromatogr., 455, 406-409.

Bourzeix M., Dubernet M.O., Heredia N., 1975. Sur l’extraction de de divers constituants phénoliques des raisins et de leurs rafles. Industries alimentaires et Agricoles, 9-10, 1057-1064.

Bourzeix M., Weyland D., Heredia N., 1986. Étude des catéchines et des procyanidols de la grappe de raisin, du vin et d’autres dérivés de la vigne. Bull O.I.V., 59, 1171-1254.

Bradshaw M.P., Prenzler P.D., Scollary G.R., 2001. Ascorbic acid-induced browning of (+)catechin in a model wine system. J. Agric. Food Chem., 49, 934-939

Cassidy A., Hanley B., Lamuela-Raventos R.M., 2000. Review. Isoflavones, lignans and stilbenes – origins, metabolism and potential importance to human health. J. Sci. Food Agric., 80, 1044-1062.

Cheynier V., Doco T., Fulcrand H., Guyot S., Le Roux E., Souquet J.M., Rigaud J., Moutounet M., 1997. ESI-MS analysis of polyphenolic oligomers and polymers. Analusis, 25 (8), 32-37.

Creasy L.L., Coffee M., 1988. Phytoalexin production potential of grape berries. J. Am. Soc. Hortic. Sci., 113, 230-234.

Csiktusnàdi Kiss G.A., Forgàcs E., Cserhati T., Mota T., Morais H., Ramos A., 2000. Optimization of the microwave-assisted extraction of pigments from paprika (Capsicum annuum L.) powders, J. Chromatogr. A, 889, 41-49

Czochanska Z., Foo L.Y., Newman R.H., Porter L.J., Tomas W.A., Jones W.T., 1979. Direct proof of a homogeneous polyflavan-3-ol structure for polymeric proanthocyanidins. J. Chem. Soc. Chem. Comm., 375 -377.

Czochanska Z., Foo L.Y., Newman R.N., Porter L.J., 1980. Polymeric proanthocyanidins stereochemistry, structural units and molecular weight. J. Chem. Soc. Perkin Trans. I., 2278-2286.

Darné G., Madero-Tamargo J., 1979. Mise au point d’une méthode d’extraction des lipides soluble totaux, des glucides solubles totaux et des composés phénoliques solubles totaux des organes de la vigne. Vitis, 18, 221 -228.

De Freitas V., Glories Y., Bourgeois G., Vitry C., 1998. Characterization of oligomeric and polymeric procyanidins from grape seeds by liquid secondary ion mass spectrometry. Phytochemistry, 49, 1435 – 1441.

De Pascual-Teresa S., Rivas-Gonzalo J.C., 2003. Application of LC-MS for the identification of polyphenols. In: Methods in Polyphenol Analysis, Chapter 3. C. SANTOS-BUELGA and G. WILLIAMSON (eds.) , Athenaeum Press, UK, pp 48-62.

Deshpande S.S., Cheryan M., Salunkhe D.K., 1986. Tannin analysis of food products, CRC Critical Reviews in Food Science and Nutrition, 24, 401-449.

Ferreira D., Guyot S., Marnet N., Delgadillo I,. Renard C.M.G.C., Coimbra M.A., 2002. Composition of phenolic compounds in a Portuguese pear (Pyrus communis L. Var.. S. Bartolomeu) and changes after sun-drying, J. Agric. Food Chem., 50, 4537-4544.

Fulcrand H., Remy S., Souquet J.M., Cheynier V., Moutounet M., 1999. Study of wine tannin oligomers by on-line liquid chromatography electrospray ionization mass spectrometry. J. Agric. Food Chem., 47, 1023-1028.

Fuleki T., Ricardo-da-Silva J.M., 1997 Catechin and Procyanidin composition of seeds from grape cultivars grown in Ontario. J. Agric. Food Chem. 45, 1156-1160.

Geissman T.A., Dittmar H.F.K., 1965. A proanthocyanidin from avocado seed. Phytochemistry, 4, 359-368.

Glories Y., 1978. Recherches sur la matière colorante des vins rouges. PhD. Thesis of State, Université de Bordeaux II.

Goldberg D.M., Karumanchiri A., NG E., Yan J., Diamandis E.P., Soleas G.J., 1995b. Direct gas chromatographic-mass spectrometric method to assay cis-resveratrol in wines: Preliminary survey of its concentration in commercial wines. J. Agric. Food Chem., 43, 1245-1250.

Goldberg D.M., NG E., Karumanchiri A., Diamandis E.P., Soleas G.J., 1996. Resveratrol glucosides are important components of commercial wines. Am. J. Enol. Vitic., 47 (4), 415-420.

Goldberg D.M., Yan J., Ng E., Diamandis E.P., Karumanchiri A., Soleas G., Waterhouse A.L., 1995a. A global survey of trans-reveratrol concentrations in commercial wines. Am. J. Enol. Vitic., 46, 159-165.

Guyot S., Doco T., Souquet J.M., Moutounet M., Drilleu J.F., 1997. Characterization of highly polymerized procyanidins in cider apple (Malus Sylvestris Var Kermerrien) skin and pulp. Phytochemistry, 44 (2), 351-357.

Guyot S., Marnet N., Drilleu J.F., 2001. Thiolysis-HPLC characterization of apple procyanidins covering a large range of polymerization states. J. Agric. Food Chem., 49, 14-20.

Hammerstone J.F., Lazarus S.A., Mitchell A.E., Rucker R., Schmitz H.H., 1999. Identification of procyanidins in cocoa (Theobroma cacao) and Chocolate using high-performance liquid chromatography/mass spectrometry J. Agric. Food Chem., 47, 490-496.

Haslam E., 1980. In Vino Veritas. Oligomeric procyanidins and the aging of red wines. Phytochemistry, 19, 1577 -1582.

Hayasaka Y., Waters E.J., Cheynier V., Herderich M.J., Vidal S., 2003. Characterization of proanthocyanidins in grape seeds using electrospray mass spectrometry, Rapid communications in mass spectrometry, 17, 9-16.

Jaworski A.W., Lee C.Y., 1987. Fractionation and HPLC determination of grape phenolics. J. Agric. Food Chem., 35, 257-259.

Jeandet P., Bessis R., Gautheron B., 1991. The production of resveratrol (3,5,4’-trihydroxystilbene) by grape berries in different developmental stages. Am. J. Enol. Vitic., 42, 41-46.

Jeandet P., Bessis R., Maume B.F., Meunier P., Peyron D., Trollat P., 1995a. Effect of enological practices on the resveratrol isomer content of wine. J. Agric. Food Chem., 43, 316-319.

Jeandet P., Douillet-Breuil A.C., Bessis R., Debord S., Sbaghi M., Adrian M., 2002. Phytoalexins from the Vitaceae: Biosynthesis, phytoalexin gene expression in transgenic plants, antifungal activity, and metabolism. J. Agric. Food Chem., 50, 2731-2741.

Jeandet P., Douillet-Breuil A.C., Bessis R., Debord S., Sbaghi M., Adrian M., 2002. Phytoalexins from the Vitaceae: Biosynthesis, phytoalexin gene expression in transgenic plants, antifungal activity, and metabolism. J. Agric. Food Chem., 50, 2731-2741.

Jeandet P., Sbaghi M., Bessis R., Meunier P. 1995b. The potential relationship of stilbene (resveratrol) synthesis to anthocyanin content in grape berry skins. Vitis, 34 (2), 91- 94.

Jones W.T., Broadhurst R.B., Lyttleton J.W., 1976. The condensed tannins of Pasture legume species. Phytochemistry, 15, 1407-1409.

Jordão A.M., Ricardo-da-Silva J.M., Laureano O., 2001a. Evolution of catechins and oligomeric procyanidins during grape maturation of Castelão Francês and Touriga Francesa. Am. J. Enol. Vitic., 52, 230-234.

Jordão A.M., Ricardo-da-Silva J.M., Laureano O., 2001b. Evolution of proanthocyanidins in bunch stems during berry development (Vitis vinifera L.). Vitis, 40, 17-22.

Kolodziej H., 2002. Isolation, structural identification and NMR spectroscopy of proanthocyanidins. In: Polyphenols 2000. Marten S., Treutter D. and Forkmann G. eds; freisingweihenstephan, 2002; pp 98-119.

Lamuela-Raventós R.M., Romero-Pérez A.I., Waterhouse A.L., Torre-Boronat M.C., 1995. Direct HPLC analysis of cis-and trans-resveratrol and piceid isomers in Spanish red Vitis vinifera wines. J. Agric. Food Chem., 43, 281-283.

Landrault N., Larronde F., Merillon J.M., Teissedre P.L., 1999. Étude de stilbenes-trans (astringine, resvératrol, picéïde) par CLHP-fluorimétrie au cours de la transformation du raisin en vin. Ann. Fals. Exp. Chim., 949, 443-453.

Langcake P., 1981. Disease resistance of Vitis spp. And the production of the stress metabolites resveratrol, e-viniferin, a-viniferin and pterostilbene. Physiol Plant Pathol., 18, 213-226.

Langcake P., Mccarthy W.V., 1979. The relationship of resveratrol production to infection of grapevine leavas by Botrytis cinerea. Vitis, 18, 244-253.

Langcake P., Pryce R.J., 1976. The production of resveratrol by Vitis vinifera and other members of the Vitaceae as a response to infection or injury. Physiol. Plant Pathol., 9, 77-86.

Larronde F., Gaudillere J.P., Krisa S., Decendit A., Deffieux G., Merillon J., 2003. Airborne Methyl Jasmonate induces stilbene accumulation in leaves and berries of grapevine plants. Am. J. Enol. Vitic., 54, 63-66.

Lazarus S.A., Adamson G.E., Hammerstone J.F., Schmitz H.H., 1999. High-performance liquid chromatography/mass spectrometry analysis of proanthocyanidins in foods and beverages. J. Agric. Food Chem., 47, 3693-3701.

Le Roux E., Doco T., Sarni P., Lozano Y., Cheynier V., 1998. A-type proanthocyanidins from pericarp of Litchi Chinensis, Phytochemistry, 48, 1251-1258

Lea A.G.H., Bridle P., Timberlake C.F., Singleton V.L., 1979. The procyanidins of white grapes and wines. Am. J. Enol. Vitic., 30, 289-300.

Lea A.G.H., Timberlake C.F., 1974. The phenolics of cider. I. Procyanidins. J. Sci. Food Agric., 25, 1537-1545.

Lee C.Y., Jaworski A.W., 1987. Phenolic compounds in white grapes grown in New York. Am. J. Enol. Vitic., 38, 277-281.

Lee C.Y., Jaworski A.W., 1989. Major phenolic compounds in ripening white grapes. Am. J. Enol. Vitic., 40, 43 -46.

Lee C.Y., Jaworski A.W., 1990. Identification of some phenolics in white grapes. Am. J. Enol. Vitic., 41, 87-89.

Lunte S.M., Blankenship K., Reed S.A., 1988. Detection and identification of procyanidins and flavanols in wine by dual-electrode liquid chromatography-electrochemistry. Analyst, 133, 99-102.

Matthews S., Mila I., Scalbert A., Pollet B., Lapierre C., Herve Du Penhoat C.L.M., Rolando C., Donnelly D.M.X., 1997. Method for estimation of proanthocyanidins based on their acid depolymerization in the presence of nucleophiles. J. Agric. Food Chem., 45, 1195-1201.

Mattivi F., 1993. Solid phase extraction of trans-resveratrol from wines for HPLC analysis. Z. Lebensm Unters Forsch., 196, 522-525.

Mattivi F., Reniero F.E., Korhammer S., 1995. Isolation, Characterisation and evolution in red wine vinification of resveratrol isomers. J. Agric. Food Chem., 43, 1820-1823.

Meirelles C., Sarni F., Ricardo-da-Silva J.M., Moutounet M., 1992. Evaluation des procyanidines galloylées dans les vins rouges issue de différents modes de vinification.In : Proceedings of International Polyphenolic Group Convention. Lisbon, Vol. 16, Tome II, pp 175-178.

Metivier R.P., Francis F.J., Clydesdale F.M., 1980. Solvent extraction of anthocyanins from wine pomace. J. Food Sci., 45, 1099-1100.

Monteiro M.J.P., Bertrand A., 1994. Validation d’une méthode de dosage. Application a l’analyse des amines biogénes du vin. Feuillet Vert nº 970.

Nitao J.K., Birr B.A., Nair M.G., Herms D.A., Mattson W.J., 2001. Rapid quantification of proanthocyanidins (condensed tannins) with a continuous flow analyzer J. Agric. Food Chem., 49, 2207-2214.

Okuda T., Yokotsuka K., 1996. Trans-resveratrol concentration in berry skins and wines from grapes grown in Japan. Am. J. Enol. Vitic., 47 (1), 93-98.

Ó-Marques J., Reguinga R., Laureano O., Ricardo-da-Silva J.M., 2005. Changes in grape seed, skin and pulp condensed tannins during berry ripening: effect of fruit pruning. Ciência Téc. Vitiv. 20 (1), 35-52.

Oszmianski J., Lee C.Y., 1990. Isolation and HPLC determination of phenolic compounds in red grapes. Am. J. Enol. Vitic., 41, 204 -206.

Oszmianski J., Ramos T., Bourzeix M., 1988. Fractionation of phenolic compounds in red wine. Am. J. Enol. Vitic., 39 (3), 259-262. .

Oszmianski J., Sapis J.C., 1989. Fractionation and identification of some low molecular weight grape seed phenolics. J. Agric. Food Chem., 37, 1293-1297.

Pezet R., Cuenat P., 1996. Resveratrol in wine: extraction from skin during fermentation and post-fermentation standing of must from Gamay grapes. Am. J. Enol. Vitic., 47, 287-290.

Pianet T., Absalon C., Vitry C., Vivas N., Vivas de Gaulejac N., Nonier M.F., 2002. Structural mapping of grape procyanidin polymers, In: Proceedings of XXI International Conference on Polyphenols. Vol. 2, pp 451-452, Marrakech-Morocco.

Piretti M.V., Guedini M., Serrazanetti G.P., 1976. Isolation and identification of the polyphenolic and terpenoid constituents of Vitis vinifera V. trebbianno Variety. Ann. Chim. (Rome), 66, 429-437.

Porter L.J. 1994. Flavans and proanthocyanidins. In: The flavonoids: Advances in Research since 1986.Harborne, J. B. ed.; Chapman and Hall press: London and New York, pp 23 -64.

Porter L.J., 1988. Flavans and proanthocyanidins. In: The flavonoids: Advances in Research since 1980. Harborne, J. B. ed.; Chapman and Hall press: London and New York, pp 21-62.

Porter L.J., 1992. Proanthocyanidins: the fifth class of plant biopolymers. .Polyphenol actualité, 8, 9-10.

Porter L.J., Newman R.H., Foo L.Y., Wong H., 1982. Polymeric proanthocyanidins. 13C N.M.R. studies of procyanidins. J. Chem. Soc. Perkin Trans., 1, 1217-1221.

Prieur C., Rigaud J., Cheynier V., Moutounet M., 1994. Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry, 3, 781-784.

Püssa T.; Floren J.; Kuldkepp P.; Raal A.; Aaviksaaar A.; Haga M., 2005. Vine stems – excellent source of resveratrols. In: Procedings of the In Vino Analytica Scientia 2005, p191.

Revilla E., Alonso E., Bourzeix M., Heredia N., 1991. Dosage des catéchines et des proanthocyanidols dans les vins. Feuillet Vert O.I.V., 829.

Ricardo-da-Silva J.M., Belchior A.P., Spranger M.I., Bourzeix M., 1992. Oligomeric procyanidins of three grapevine varieties and wines from Portugal. Sciences des Aliments, 12, 223-237.

Ricardo-da-Silva J.M., Bourzeix M., Cheynier V., Moutounet M., 1991b. Procyanidin composition of Chardonnay, Mauzac and Grenache blanc grapes, Vitis, 30, 245-252.

Ricardo-da-Silva J.M., Rigaud J., Cheynier V., Cheminat A., Moutounet M., 1991a. Procyanidin dimers and trimers from grape seeds, Phytochemistry, 4, 1259-1264.

Ricardo-da-Silva J.M., Rosec J.P., Bourzeix M., Heredia N., 1990. Separation and quantitative determination of grape and wine procyanidins by high performance reversed phase liquid chromatography. J. Sci. Food Agric., 53, 85-92.

Rigaud J., Escribano-Bailon M.T., Prieur C., Souquet J.M., Cheynier V., 1993. Normal-phase high-performance liquid chromatographic separation of procyanidins from cacao beans and grape seeds. J. Chromatogr., 654, 255-260.

Roggero J.P., Garcia-Parrilla C., 1995. Effects of ultraviolet irradiation on resveratrol and changes in resveratrol and various of its derivatives in the skins of ripening grapes. Sciences des aliments, 15, 411-422.

Rohr G.E., 2002. Analysis of proanthocyanidins. In: Polyphenols 2000. Marten S., Treutter D. and Forkmann G. (eds), freising-weihenstephan, pp 60-97

Romero-Pérez A., Lamuela-Raventos R.M., Buxaderas S., De La Torre-Boronat C.M., 1996a. Resveratrol and piceid as varietal markers of white wines. J. Agric. Food Chem., 44, 1975-1978.

Romero-Pérez A., Lamuela-Raventos R.M., Waterhouse A.L., De La Torre-Boronat M.C., 1996b. Levels of cis and trans-resveratrol and piceid isomers in rosé and white Vitis vinifera wines. J. Agric. Food Chem., 44, 2124-2128.

Romeyer F.M., Macheix J.J., Sapis J.C., 1986. Changes and importance of oligomeric procyanidins during maturation of grape seeds. Phytochemistry, 25, 219-221.

Saint-Cricq De Gaulejac N., Freitas V., Glories Y., Bourgeois G., Vivas N., 1998. Fractionement et dosage des procyandines oligomère des raisins et des vins: relation avec la qualité des vins. Sciences des Aliments, 18, 59-76.

Saucier C., Mirabel M., Daviaud F., Longieras A., Glories Y., 2001. Rapid fractionation of grape seed proanthocyanidins, J. Agric. Food Chem., 49, 5732-5735.

Siemann E.H., Creasy L.L., 1992. Concentration of the phytoalexin resveratrol in wine. Am. J. Enol. Vitic., 43 (1), 49–52.

Soleas G.J., Goldberg D.M., Diamandis E.P., Karumanchiri A., Yan J., E NG., 1995. A derivatized Gas Chromatographic – Mass spectrometric method for the analisys of both isomers of resveratrol in juice and wine. Am. J. Enol. Vitic., 46, 346-352.

Somers T.C., 1968. Pigment profiles of grapes and wines. SONDERDRUCK aus der Zeitschrift VITIS, 7, 303-320.

Souquet J., Cheynier V., Brossaud F., Moutounet M., 1996. Polymeric proanthocyanidins from grape skins. Phytochemistry, 43, 509 -512.

Souquet J., Cheynier V., Moutounet M., 1998. Phenolic composition of grape stems. In: Proceedings of the XIXth International Conference on Polyphenols, F. Charbonnier, J.M. Delacotte and C. Rolando (Eds), Lille (France), Vol. 2, pp359-360.

Souquet J., Labarbe B., Le Guernevé C., Cheynier V., Moutounet M., 2000. Phenolic composition of grape stems. J. Agric. Food Chem., 48, 1076-1080.

Spranger M.I., Sun B.S., Leandro M.C., Cavalho E.C., Bechior A.P., 1998. Changes in anthocyanins, catechins and proanthocyanidins during fermentation and early post-fermentation of red grapes. In:Proceeding of XXIII Word Congress on Vine and Wine, Lisbon, Portugal, Vol. II, pp183-189.

Stonestreet E., 1965. Contribution à l’étude des tannins et de la matiè re colorante des vins rouges. Ph D thesis, Université de Bordeaux.

Su C.T., Singleton V.L., 1969. Identification of three flavan-3-ols from grapes. Phytochemistry, 8, 1553-1558.

Sun B.S., 1999. Grape and wine proanthocyanidins: isolation, chemical characterization, quantification and their importance in enology. PhD. thesis, Universidade Técnica de Lisboa, p 203.

Sun B.S., Belchior G.P., Ricardo-da-Silva J.M., Spranger M.I. 1999b. Isolation and purification of dimeric and trimeric procyanidins from grape seeds, J. Chromatogr. A, 841, 115-121.

Sun B.S., Ferrão C., Spranger M.I., 2001c. Effect of various winemaking technologies on resveratrol content in red wines. In:International Congress of In Vino Analytica Scientia 2001, 14-16 June 2001, Bordeaux, França, p. 157.

Sun B.S., Spranger M.I., Leandro M.C., 1994. Dosage des catéchines et des procyanidines du raisin et du vin. Optimization de la méthode de reaction avec la vanilline. In : Polyphenols 94, INRA Ed., Paris (France), pp 455-456.

Sun B.S., Ferrão C., Spranger M.I., 2003b. Effect of wine style and winemaking technology on resveratrol level in wines. Ciência Téc. Vitiv., 18, 77-91.

Sun B.S., Leandro M.C., De Freitas V., Spranger M.I., 2005b. Rapid fractionation of red wine polyphenols by solid phase extraction and liquid chromatography. J. Separation Sci. (to be submitted).

Sun B.S., Leandro M.C., Ricardo-da-Silva J.M., Spranger M.I., 1998a. Separation of grape and wine proanthocyanidins according to their degree of polymerization. J. Agric. Food Chem. 46, 1390-1396.

Sun B.S., Pinto T., Leandro M.C., Ricardo-da-Silva J.M., Spranger M.I., 1999a. Transfer of catechins and proanthocyanidins from grape solids into wine, Am. J. Enol. Vitic., 50 (2), 179-184.

Sun B.S., Ribes A., Leandro M.C., Belchior A.P., Spranger M.I., 2005c. Stilbenes: quantitative extraction from grape skins, contribution of grape solids to wine and variation during wine maturation. Analytica Chimica Acta, (in press).

Sun B.S., Ricardo-da-Silva J.M., Spranger M.I. 2001a. Quantification of catechins and proanthocyanidins in several Portuguese grapevine varieties and red wines, Ciência Téc. Vitiv. 16, 23-34.

Sun B.S., Spranger M.I., 2005a. Changes in phenolic composition of Tinta Miúda red wines after 2 years of ageing in bottle: effect of winemaking technologies. Eur. Food Res. Technol., 221, 305-312.

Sun B.S., Spranger M.I., Roque-do-Vale F., Leandro M.C., Belchior P., 2001b. Effect of different winemaking technologies on phenolic composition in Tinta Miúda red wines. J. Agric. Food Chem. 49, 5809-5816.

Sun B.S., Spranger M.I., Roque-do-Vale F., Ricardo-da-Silva J.M., 1999c. Thioacidolysis-HPLC characterization of oligomeric and polymeric procyanidin fractions from grape seeds. In: Actas do 1º Encontro Nacional de Cromatografia, Lisboa, 34-35.

Sun B.S., Spranger M.I.,, Leandro M.C., Belchior P., 2003a. Evolution of phenolic compounds in red wines during ageing. In: Abstract books of the 1st International Conference on Polyphenols and Health, Vichy, France, p198.

Sun, B.S., Ricardo-da-Silva, J.M., Spranger, M.I., 1998b. Critical factors of vanillin assay for catechins and proanthocyanidins. J. Agric. Food Chem., 46, 4267-4274.

Sun, B.S., Spranger, M.I., Ricardo-da-Silva, J.M., 1996. Extraction of grape seed procyanidins using different organic solvents. In: Proceedings of the 18th International Conference on Polyphenols,J.Vercauteren, C. Chèze, M.C. Dumon and J.F. Weber (Eds), Bordeaux (France).

Thompson R.S., Jacques D., Haslam E., Tanner R.J.N., 1972. Plant proanthocyanidins. Part I. Introduction: The isolation, structure and distribution in nature of plant procyanidins. J. Chem. Soc. Perkin trans, 1, 1387-1399.

Thorngate J.H., Singleton V.L., 1994. Localisation of procyanidins in Grape Seeds. Am. J. Enol. Vitic., 45, 259-262.

Tiarks A.E., Meier C.E., Flagler R.B., Steynberg E.C., 1992. Sequential extraction of condensed tannins from pine litter at different stages of decomposition. In: Plant Polyphenols: Synthesis, Properties, Significance; Hemingway, R. W. and Laks, P. S. (eds.), Plenum Press: New York, pp 597-608.

Vidal S., Cartalade D., Souquet J.M., Fulcrand H., Cheynier V., 2002. Changes in proanthocyanidin chain length in winelike model solutions. J. Agric. Food Chem., 50, 2261-2266.

Vrhovsek U., Wendelin S., Eder R., 1997. effects of various vinification techniques on the concentration of cis- and trans-resveratrol and resveratrol glucoside isomers in wine. Am. J. Enol. Vitic., 48 (2), 214-219.

Weinges K., Piretti M.V., 1971. Isolierung des procyanidins B1 Aus Weintrauben. Liebigs. Ann. Chem. Dtsch., 748, 218-220.

Xu L., Diosady L.L., 1997. Rapid method for total phenolic acid determination in rapeseed/ canola meals. Food Res. Int., 30, 571-574.

Yokotsuka K., Singleton V.L., 1987. Interactive precipitation between grape peptides from gelatin and specific grape tannin fractions in wine-like model solutions. Am. J. Enol. Vitic., 38, 199-206.