Upgrading of grape skins: Significance of plant cell-wall structural components and extraction techniques for phenol release

In grape skins, phenols may be classified as (1) cell-wall phenols, which are bound to polysaccharides by hydrophobic interactions and hydrogen bonds, and (2) non-cell-wall phenols, encompassing phenols confined in the vacuoles of plant cells and phenols associated with the cell nucleus. The phenolic composition of wines determines the colour quality, the sensory, and the potential health promoting properties of wines, and the extraction of phenols from the grapes into the must and wine is to a large extent governed by how the phenols are bound and entangled in the grape skins. Degradation of cell-wall polysaccharides is a fundamental step to improve the release of phenols from grape skin whether this is in winemaking or in upgrading of wine pomace. Cellulases, hemicellulases, pectinases, and other enzymes able to catalyze the hydrolysis of bonds in plant cell-wall polysaccharides can be employed to decompose the cell-wall structure. In addition, novel extraction principles and optimization of extraction conditions such as temperature, solvent-to-solid ratio, use of supercritical fluids and new extraction cell designs have shown promise for optimizing the release of phenols from grape skins for valorization of wine pomace. An in-depth knowledge of how phenols are bound in grape skins will allow us to employ the most suitable techniques to release phenols in order to optimize the phenol-related properties of wine and maximize the phenol recovery from grape byproducts.

[1]  C. Barroso,et al.  Study of the polyphenol content of red and white grape varieties by liquid chromatography-mass spectrometry and its relationship to antioxidant power. , 2003, Journal of chromatography. A.

[2]  S. Guyot,et al.  Non-covalent interaction between procyanidins and apple cell wall material: Part I. Effect of some environmental parameters. , 2004, Biochimica et biophysica acta.

[3]  P. Kefalas,et al.  Radical scavenging activity of various extracts and fractions of sweet orange peel (Citrus sinensis) , 2006 .

[4]  N. Carpita,et al.  Changes in Esterification of the Uronic Acid Groups of Cell Wall Polysaccharides during Elongation of Maize Coleoptiles. , 1992, Plant physiology.

[5]  M. González-Sanjosé,et al.  Identification of anthocyanin derivatives in grape skin extracts and red wines by liquid chromatography with diode array and mass spectrometric detection , 1999 .

[6]  M. Pinelo,et al.  Mass transfer during continuous solid–liquid extraction of antioxidants from grape byproducts , 2006 .

[7]  R. Sun,et al.  Determination of cell wall ferulic and p-coumaric acids in sugarcane bagasse , 2005 .

[8]  B. Bartolomé,et al.  Adsorption of anthocyanins by yeast cell walls during the fermentation of red wines. , 2003, Journal of agricultural and food chemistry.

[9]  F. Pardo,et al.  Effect of diverse enzyme preparations on the extraction and evolution of phenolic compounds in red wines , 1999 .

[10]  A. Meyer,et al.  Inhibition of Human Low-Density Lipoprotein Oxidation in Relation to Composition of Phenolic Antioxidants in Grapes (Vitis vinifera) , 1997 .

[11]  D. An,et al.  Influence des enzymes pectolytiques sélectionnées pour l'oenologie sur la qualité et la composition des vins rouges , 1997 .

[12]  S. Conn,et al.  Anthocyanic vacuolar inclusions (AVIs) selectively bind acylated anthocyanins in Vitis vinifera L. (grapevine) suspension culture , 2003, Biotechnology Letters.

[13]  J. Ralph,et al.  Cross-linking of maize walls by ferulate dimerization and incorporation into lignin. , 2000, Journal of agricultural and food chemistry.

[14]  K. Keegstra,et al.  The Structure of Plant Cell Walls: III. A Model of the Walls of Suspension-cultured Sycamore Cells Based on the Interconnections of the Macromolecular Components. , 1973, Plant Physiology.

[15]  S. Fry,et al.  Evidence for covalent linkage between xyloglucan and acidic pectins in suspension-cultured rose cells , 2000, Planta.

[16]  J. Polster,et al.  Nuclei of tea flowers as targets for flavanols. , 2004, Plant biology.

[17]  A. Pell,et al.  Analysis of condensed tannins: a review , 2001 .

[18]  L. Foo,et al.  The polyphenol constituents of grape pomace , 1999 .

[19]  S. Fry,et al.  Novel O-D-Galacturonoyl Esters in the Pectic Polysaccharides of Suspension-Cultured Plant Cells , 1993, Plant physiology.

[20]  R. Toledo,et al.  Major flavonoids in grape seeds and skins: antioxidant capacity of catechin, epicatechin, and gallic acid. , 2004, Journal of agricultural and food chemistry.

[21]  D. Treutter,et al.  Flavanol binding of nuclei from tree species , 2003, Plant Cell Reports.

[22]  M. Moutounet,et al.  Aggregation of grape seed tannins in model wine—effect of wine polysaccharides , 2002 .

[23]  A. Waterhouse,et al.  Changes in grape seed polyphenols during fruit ripening. , 2000, Phytochemistry.

[24]  K. Gould,et al.  Cytoplasmic accumulation of flavonoids in flower petals and its relevance to yellow flower colouration. , 2001, Phytochemistry.

[25]  V. Cheynier,et al.  Phenolic composition of grape stems. , 2000, Journal of agricultural and food chemistry.

[26]  Reinhold Carle,et al.  A novel process for the recovery of polyphenols from Grape (Vitis vinifera L.) Pomace , 2005 .

[27]  S. Guyot,et al.  Interactions between apple cell walls and native apple polyphenols: quantification and some consequences. , 2001, International journal of biological macromolecules.

[28]  N. Mateus,et al.  Study of carbohydrate influence on protein–tannin aggregation by nephelometry , 2003 .

[29]  R. Carle,et al.  Polyphenol screening of pomace from red and white grape varieties (Vitis vinifera L.) by HPLC-DAD-MS/MS. , 2004, Journal of agricultural and food chemistry.

[30]  M. Pinelo,et al.  Effect of solvent, temperature, and solvent-to-solid ratio on the total phenolic content and antiradical activity of extracts from different components of grape pomace. , 2005, Journal of agricultural and food chemistry.

[31]  N. Carpita,et al.  Structural models of primary cell walls in flowering plants: consistency of molecular structure with the physical properties of the walls during growth. , 1993, The Plant journal : for cell and molecular biology.

[32]  M. Pinelo,et al.  Effect of bubbling nitrogen and pulsed flow on the antiradical activity of grape residues , 2006 .

[33]  N. Mateus,et al.  Proanthocyanidin Composition of Red Vitis vinifera Varieties from the Douro Valley during Ripening: Influence of Cultivation Altitude , 2001, American Journal of Enology and Viticulture.

[34]  Hansang Jung,et al.  Forage Lignins and Their Effects on Fiber Digestibility , 1989 .

[35]  J. López-Roca,et al.  Phenolic Compounds and Color Stability of Red Wines: Effect of Skin Maceration Time , 2001, American Journal of Enology and Viticulture.

[36]  J. Ralph,et al.  Ferulate Cross-Links Limit the Enzymatic Degradation of Synthetically Lignified Primary Walls of Maize , 1998 .

[37]  Xiao-Feng Sun,et al.  Fractional and physico-chemical characterization of hemicelluloses from ultrasonic irradiated sugarcane bagasse. , 2004, Carbohydrate research.

[38]  Peter H. Raven,et al.  Biology of plants , 1976 .

[39]  M. di Bella,et al.  Study of flavonoids/beta-cyclodextrins inclusion complexes by NMR, FT-IR, DSC, X-ray investigation. , 2002, Journal of pharmaceutical and biomedical analysis.

[40]  P Albersheim,et al.  Rhamnogalacturonan-II, a Pectic Polysaccharide in the Walls of Growing Plant Cell, Forms a Dimer That Is Covalently Cross-linked by a Borate Ester , 1996, The Journal of Biological Chemistry.

[41]  C. Léger,et al.  Wine phenolic antioxidants inhibit AP-1 transcriptional activity. , 2001, Journal of agricultural and food chemistry.

[42]  E. Castanas,et al.  Potent inhibitory action of red wine polyphenols on human breast cancer cells , 2000, Journal of cellular biochemistry.

[43]  S. Kallithraka,et al.  Determination of low molecular weight polyphenolic constituents in grape (Vitis vinifera sp.) seed extracts: Correlation with antiradical activity , 2005 .

[44]  A. Meyer,et al.  Enzymatic Release of Antioxidants for Human Low-Density Lipoprotein from Grape Pomace , 1998 .

[45]  K. Gould,et al.  Cell wall sited flavonoids in lisianthus flower petals. , 2000, Phytochemistry.

[46]  J. Stull,et al.  Activation of smooth muscle contraction: relation between myosin phosphorylation and stiffness. , 1986, Science.

[47]  A. Meyer,et al.  Enzyme-assisted extraction of antioxidative phenols from black currant juice press residues (Ribes nigrum). , 2001, Journal of agricultural and food chemistry.

[48]  J. German,et al.  Inhibition of in vitro human LDL oxidation by phenolic antioxidants from grapes and wines , 1996 .

[49]  J. F. Tomera Current knowledge of the health benefits and disadvantages of wine consumption , 1999 .

[50]  M. Pinelo,et al.  Interaction among phenols in food fortification: negative synergism on antioxidant capacity. , 2004, Journal of agricultural and food chemistry.

[51]  Silvia Pérez-Magariño,et al.  Polyphenols and colour variability of red wines made from grapes harvested at different ripeness grade , 2006 .

[52]  B. Girard,et al.  Vinification effects on the sensory, colour and GC profiles of Pinot noir wines from British Columbia , 2001 .

[53]  I. Arts,et al.  Catechin contents of foods commonly consumed in The Netherlands. 1. Fruits, vegetables, staple foods, and processed foods. , 2000, Journal of agricultural and food chemistry.

[54]  J. Grabber How Do Lignin Composition, Structure, and Cross‐Linking Affect Degradability? A Review of Cell Wall Model Studies , 2005 .

[55]  B. Bouchet,et al.  Non-covalent interaction between procyanidins and apple cell wall material. Part III: Study on model polysaccharides. , 2005, Biochimica et biophysica acta.

[56]  L. Tommasi,et al.  Phenolic compounds and antioxidant activity from red grape marc extracts. , 2003, Bioresource technology.

[57]  J. Ralph,et al.  Model studies of ferulate-coniferyl alcohol cross-product formation in primary maize walls: implications for lignification in grasses. , 2002, Journal of agricultural and food chemistry.

[58]  Y. Glories,et al.  Developmental Changes of Procyanidins in Grapes of Red Vitis vinifera Varieties and Their Composition in Respective Wines , 2000, American Journal of Enology and Viticulture.

[59]  R. Hartley,et al.  Linkage of p-coumaroyl and feruloyl groups to cell-wall polysaccharides of barley straw , 1986 .

[60]  V. Cheynier,et al.  Polymeric proanthocyanidins from grape skins , 1996 .

[61]  Linda F. Bisson,et al.  A Review of the Effect of Winemaking Techniques on Phenolic Extraction in Red Wines , 2005, American Journal of Enology and Viticulture.

[62]  J. Oszmiański,et al.  Fractionation and identification of some low molecular weight grape seed phenolics , 1989 .

[63]  J. Brillouet,et al.  Cell wall composition of grape berry skins , 1994 .

[64]  M. Pinelo,et al.  Optimization of continuous phenol extraction from Vitis vinifera byproducts , 2005 .

[65]  C. Renard,et al.  Non-covalent interaction between procyanidins and apple cell wall material. Part II: Quantification and impact of cell wall drying. , 2005, Biochimica et biophysica acta.

[66]  T. Goodwin,et al.  Introduction to plant biochemistry , 1972 .

[67]  M. Pauly,et al.  Polysaccharides from grape berry cell walls. Part II. Structural characterization of the xyloglucan polysaccharides , 2003 .

[68]  K. Waldron,et al.  Physiology and Biochemistry of Plant Cell Walls , 1990, Topics in Plant Physiology.

[69]  Fincher,et al.  Changes in cell wall composition during ripening of grape berries , 1998, Plant physiology.

[70]  M. O’Neill,et al.  Polysaccharides from grape berry cell walls. Part I: tissue distribution and structural characterization of the pectic polysaccharides , 2001 .

[71]  J. López-Roca,et al.  Improving colour extraction and stability in red wines: the use of maceration enzymes and enological tannins , 2005 .

[72]  B. Bartolomé,et al.  Chemical characterization of commercial dietary ingredients from Vitis vinifera L. , 2006 .

[73]  S. Reuber,et al.  Tissue localization of phenolic compounds in plants by confocal laser scanning microscopy , 1998 .

[74]  P. A. Roelofsen The plant cell-wall , 1959 .

[75]  Giuseppe Mazza,et al.  Mass transfer process during extraction of phenolic compounds from milled berries , 2003 .

[76]  James E. Bidlack,et al.  Molecular structure and component integration of secondary cell walls in plants , 1992 .

[77]  A. Berna,et al.  Supercritical fluid extraction of resveratrol from grape skin of Vitis vinifera and determination by HPLC. , 2001, Talanta.

[78]  J. Ralph,et al.  Diferulate cross-links impede the enzymatic degradation of non-lignified maize walls , 1998 .

[79]  J. Grandmaison,et al.  Evidence for Nuclear Protein Binding of Flavonol Sulfate Esters in Flaveria chloraefolia , 1995 .

[80]  J. Thompson,et al.  Xyloglucan undergoes interpolymeric transglycosylation during binding to the plant cell wall in vivo: evidence from 13C/3H dual labelling and isopycnic centrifugation in caesium trifluoroacetate. , 1997, The Biochemical journal.

[81]  E. Meudec,et al.  Reactions of anthocyanins and tannins in model solutions. , 2003, Journal of agricultural and food chemistry.

[82]  K. Gould,et al.  Anthocyanic vacuolar inclusions--their nature and significance in flower colouration. , 2000, Phytochemistry.

[83]  Celestino Santos-Buelga,et al.  Flavanol content and antioxidant activity in winery byproducts. , 2004, Journal of agricultural and food chemistry.

[84]  John Ralph,et al.  Plant biology and pathology / Biologie et pathologie végétales Genetic and molecular basis of grass cell-wall degradability. I. Lignin-cell wall matrix interactions ✩ , 2004 .