食品科学 ›› 0, Vol. ›› Issue (): 0-0.
• 专题论述 • 下一篇
张欣珂1,赵旭2,刘沛通3,段长青4,李德美1
收稿日期:
2022-11-29
修回日期:
2023-10-11
出版日期:
2023-12-15
发布日期:
2023-12-28
通讯作者:
李德美
E-mail:demeili@sina.com
基金资助:
Received:
2022-11-29
Revised:
2023-10-11
Online:
2023-12-15
Published:
2023-12-28
Contact:
DeMei LI
E-mail:demeili@sina.com
摘要: 花色苷是贡献红葡萄酒颜色的一类重要物质,其对红葡萄酒的品质有重要的影响。在葡萄生长发育过程中,花色苷通过苯丙烷—类黄酮路径生物合成。在葡萄酒中,花色苷存在多种状态之间的平衡,其颜色表现也与花色苷分子的结构和形态密切相关。同时,花色苷并不稳定,会经过包括氧化在内的多种形式的降解。从酿造工艺角度来看,在发酵过程中花色苷从葡萄皮通过浸渍进入到酒液中,而在不同发酵阶段花色苷的含量及葡萄酒的颜色由于发酵条件和葡萄酒中组分的改变也不断变化。在陈酿过程中,花色苷会和其它的物质反应生成新的花色苷衍生物。花色苷和这些衍生物的变化也导致了在发酵、陈酿和储存过程中葡萄酒颜色不断变化。至今,尚未有文献系统性地对红葡萄酒中花色苷的来源及呈色原理,发生的反应以及在葡萄酒加工过程中的变化进行归纳总结,因此,本文针对葡萄酒中的花色苷类物质,围绕上述内容进行了综述,以期为红葡萄酒呈色和花色苷研究进行梳理,为未来研究提供一定的研究基础和理论依据。
中图分类号:
张欣珂 赵旭 刘沛通 段长青 李德美. 红葡萄酒的花色苷:来源、呈色与反应[J]. 食品科学, 0, (): 0-0.
[1] HOLTON T A, CORNISH E C. Genetics and biochemistry of anthocyanin biosynthesis [J]. The Plant Cell, 1995, 7(7): 1071. DOI: 10.1105/tpc.7.7.1071[2] TANAKA Y, SASAKI N, OHMIYA A. Biosynthesis of plant pigments: anthocyanins, betalains and carotenoids [J]. The Plant Journal, 2008, 54(4): 733-749. DOI: 10.1111/j.1365-313X.2008.03447.x[3] HE F, MU L, YAN G-L, et al. Biosynthesis of anthocyanins and their regulation in colored grapes [J]. Molecules, 2010, 15(12): 9057-9091. DOI: 10.3390/molecules15129057[4] BOSS P K, DAVIES C, ROBINSON S P. Analysis of the expression of anthocyanin pathway genes in developing Vitis vinifera L. cv Shiraz grape berries and the implications for pathway regulation [J]. Plant physiology, 1996, 111(4): 1059-1066. DOI: 10.1104/pp.111.4.1059[5] MAZZA G, FRANCIS F. Anthocyanins in grapes and grape products [J]. Critical Reviews in Food Science & Nutrition, 1995, 35(4): 341-371. DOI: 10.1080/10408399509527704[6] ANDREW L. WATERHOUSE G L S, AND DAVID W. JEFFERY. Anthocyanins [M]. Understanding Wine Chemistry. Wiley. 2016: 131. DOI: https://doi.org/10.1002/9781118730720.ch16[7] JOSHI P. Physical aspects of color in foods [M]. ACS Publications. 2000. DOI: 10.1021/bk-2001-0775.ch003[8] HEREDIA F, FRANCIA-ARICHA E, RIVAS-GONZALO J, et al. Chromatic characterization of anthocyanins from red grapes—I. pH effect [J]. Food Chemistry, 1998, 63(4): 491-498.[9] DE FREITAS V, MATEUS N. Chemical transformations of anthocyanins yielding a variety of colours (Review) [J]. Environmental Chemistry Letters, 2006, 4(3): 175-183. DOI: 10.1016/S0308-8146(98)00051-X[10] ZHAO Xu, DING Bowen, QIN Jiawei, et al. Intermolecular copigmentation between five common 3-O-monoglucosidic anthocyanins and three phenolics in red wine model solutions: The influence of substituent pattern of anthocyanin B ring [J]. Food Chemistry, 2020, 326: 126960. DOI: 10.1016/j.foodchem.2020.126960[11] GIUSTI M M, RODRíGUEZ-SAONA L E, WROLSTAD R E. Molar absorptivity and color characteristics of acylated and non-acylated pelargonidin-based anthocyanins [J]. Journal of Agricultural and Food Chemistry, 1999, 47(11): 4631-4637. DOI: 10.1021/jf981271k[12] AHMADIANI N, ROBBINS R J, COLLINS T M, et al. Molar absorptivity (ε) and spectral characteristics of cyanidin-based anthocyanins from red cabbage [J]. Food Chemistry, 2016, 197: 900-906. DOI: 10.1016/j.foodchem.2015.11.032[13] ZHAO XU, ZHANG Xinke, HE Xiaoming, et al. Acetylation of Malvidin-3-O-glucoside impedes intermolecular copigmentation: Experimental and theoretical investigations [J]. Journal of Agricultural and Food Chemistry, 2021, 69(27): 7733-7741. DOI: 10.1021/acs.jafc.1c02378[14] RUSTIONI L, DI MEO F, GUILLAUME M, et al. Tuning color variation in grape anthocyanins at the molecular scale [J]. Food Chemistry, 2013, 141(4): 4349-4357. DOI: 10.1016/j.foodchem.2013.07.006[15] HE Fei, LIANG Nana, MU Lin, et al. Anthocyanins and their variation in red wines I. Monomeric anthocyanins and their color expression [J]. Molecules, 2012, 17(2): 1571-1601. DOI: 10.3390/molecules17021571[16] BROUILLARD R, LANG J. The hemiacetal–cis-chalcone equilibrium of malvin, a natural anthocyanin [J]. Canadian Journal of Chemistry, 1990, 68(5): 755-761. DOI: 10.1002/chin.199044058[17] SANTOS H, TURNER D L, LIMA J C, et al. Elucidation of the multiple equilibria of malvin in aqueous solution by One- and two-dimensional NMR [J]. Phytochemistry, 1993, 33(5): 1227-1232. DOI: 10.1016/0031-9422(93)85054-U[18] BROUILLARD R, DUBOIS J-E. Mechanism of the structural transformations of anthocyanins in acidic media [J]. Journal of the American Chemical Society, 1977, 99(5): 1359-1364. DOI: 10.1002/chin.197721103[19] TROUILLAS P, SANCHO-GARCíA J C, DE FREITAS V, et al. Stabilizing and modulating color by copigmentation: Insights from theory and experiment [J]. Chemical Reviews, 2016, 116(9): 4937-4982. DOI: 10.1021/acs.chemrev.5b00507[20] BROUILLARD R, IACOBUCCI G, SWEENY J. Chemistry of anthocyanin pigments. 9. UV-visible spectrophotometric determination of the acidity constants of apigeninidin and three related 3-deoxyflavylium salts [J]. Journal of the American Chemical Society, 1982, 104(26): 7585-7590. DOI: 10.1002/chin.198315104[21] PINA F, MELO M J, LAIA C A, et al. Chemistry and applications of flavylium compounds: a handful of colours [J]. Chemical Society Reviews, 2012, 41(2): 869-908. DOI: 10.1039/C1CS15126F[22] PINA F, OLIVEIRA J, DE FREITAS V. Anthocyanins and derivatives are more than flavylium cations [J]. Tetrahedron, 2015, 71(20): 3107-3114. DOI: 10.1016/j.tet.2014.09.051[23] FORINO M, GAMBUTI A, LUCIANO P, et al. Malvidin-3-O-glucoside chemical behavior in the wine pH range [J]. Journal of Agricultural and Food Chemistry, 2019, 67(4): 1222-1229. DOI: 10.1021/acs.jafc.8b05895[24] MARKARIS P, LIVINGSTON G E, FELLERS C R. Quantitative aspects of strawberry pigment degradation [J]. Journal of Food Science, 1957, 22(2): 117-130. DOI: 10.1111/j.1365-2621.1957.tb16991.x[25] SADILOVA E, STINTZING F C, CARLE R. Thermal degradation of acylated and nonacylated anthocyanins [J]. Journal of Food Science, 2006, 71(8): C504-C512. DOI: 10.1111/j.1750-3841.2006.00148.x[26] SADILOVA E, CARLE R, STINTZING F C. Thermal degradation of anthocyanins and its impact on color and in vitro antioxidant capacity [J]. Molecular Nutrition & Food Research, 2007, 51(12): 1461-1471. DOI: 10.1002/mnfr.200700179[27] SUN Jianxia, BAI Weibin, ZHANG Yan, et al. Identification of degradation pathways and products of cyanidin-3-sophoroside exposed to pulsed electric field [J]. Food Chemistry, 2011, 126(3): 1203-1210. DOI: 10.1016/j.foodchem.2010.12.002[28] BARBOSA P, ARAúJO P, OLIVEIRA J, et al. Metabolic pathways of degradation of malvidin-3-O-monoglucoside by Candida oleophila [J]. International Biodeterioration & Biodegradation, 2019, 144: 104768. DOI: 10.1016/j.ibiod.2019.104768[29] WATERHOUSE A L, LAURIE V F. Oxidation of wine phenolics: A critical evaluation and hypotheses [J]. American Journal of Enology and Viticulture, 2006, 57(3): 306-313. DOI: 10.1016/S0306-9877(02)00144-5[30] DEL ALAMO-SANZA M, CáRCEL L M, NEVARES I. Characterization of the oxygen transmission rate of oak wood species used in cooperage [J]. Journal of Agricultural and Food Chemistry, 2017, 65(3): 648-655. DOI: 10.1021/acs.jafc.6b05188[31] OLIVEIRA V, LOPES P, CABRAL M, et al. Kinetics of oxygen ingress into wine bottles closed with natural cork stoppers of different qualities [J]. American Journal of Enology and Viticulture, 2013, 64(3): 395-399. DOI: 10.5344/ajev.2013.13009[32] OLIVEIRA C M, FERREIRA A C S, DE FREITAS V, et al. Oxidation mechanisms occurring in wines [J]. Food Research International, 2011, 44(5): 1115-1126. DOI: 10.1016/j.foodres.2011.03.050[33] DU TOIT W, MARAIS J, PRETORIUS I, et al. Oxygen in must and wine: A review [J]. South African Journal of Enology and Viticulture, 2006, 27(1): 76-94. DOI: 10.21548/27-1-1610[34] ROBARDS K, PRENZLER P D, TUCKER G, et al. Phenolic compounds and their role in oxidative processes in fruits [J]. Food Chemistry, 1999, 66(4): 401-436. DOI: 10.1016/S0308-8146(99)00093-X[35] LI Hua, GUO Anque, WANG Hua. Mechanisms of oxidative browning of wine [J]. Food Chemistry, 2008, 108(1): 1-13. DOI: 10.1016/j.foodchem.2007.10.065[36] DANILEWICZ J C. Review of reaction mechanisms of oxygen and proposed intermediate reduction products in wine: Central role of iron and copper [J]. American Journal of Enology and Viticulture, 2003, 54(2): 73-85. DOI: 10.1016/0013-4686(91)85172-4[37] KARBOWIAK T, GOUGEON R D, ALINC J-B, et al. Wine oxidation and the role of cork [J]. Critical Reviews in Food Science and Nutrition, 2009, 50(1): 20-52. DOI: 10.1080/10408390802248585[38] DANILEWICZ J C. Fe (II): Fe (III) ratio and redox status of white wines [J]. American Journal of Enology and Viticulture, 2016, 67(2): 146-152. DOI: 10.5344/ajev.2015.15088[39] WATERHOUSE A L, NIKOLANTONAKI M. Quinone reactions in wine oxidation [M]. Advances in Wine Research. American Chemical Society. 2015: 291-301. DOI: 10.1021/bk-2015-1203.ch018[40] OSZMIANSKI J, CHEYNIER V, MOUTOUNET M. Iron-Catalyzed Oxidation of (+)-Catechin in Model Systems [J]. Journal of Agricultural and Food Chemistry, 1996, 44(7): 1712-1715. DOI: 10.1021/jf9507710[41] SINGLETON V L. Oxygen with phenols and related reactions in musts, wines, and model systems: Observations and practical implications [J]. American Journal of Enology and Viticulture, 1987, 38(1): 69-77.[42] ANDREW L. WATERHOUSE G L S, AND DAVID W. JEFFERY. Wine Oxidation [M]. Understanding Wine Chemistry. John Wiley & Sons. 2016: 279. DOI: 10.1002/9781118730720.ch24[43] LOPES P, RICHARD T, SAUCIER C, et al. Anthocyanone A:? A quinone methide derivative resulting from malvidin 3-O-glucoside degradation [J]. Journal of Agricultural and Food Chemistry, 2007, 55(7): 2698-2704. DOI: 10.1021/jf062875o[44] GAMBUTI A, PICARIELLO L, ROLLE L, et al. Evaluation of the use of sulfur dioxide and glutathione to prevent oxidative degradation of malvidin-3-monoglucoside by hydrogen peroxide in the model solution and real wine [J]. Food Research International, 2017, 99: 454-460. DOI: 10.1016/j.foodres.2017.06.010[45] ZHAO Mengyao, LUO Yinghua, LI Yan, et al. The identification of degradation products and degradation pathway of malvidin-3-glucoside and malvidin-3, 5-diglucoside under microwave treatment [J]. Food Chemistry, 2013, 141(3): 3260-3267. DOI: 10.1016/j.foodchem.2013.05.147[46] SATAKE R, YANASE E. Mechanistic studies of hydrogen-peroxide-mediated anthocyanin oxidation [J]. Tetrahedron, 2018, 74(42): 6187-6191. DOI: 10.1016/j.tet.2018.09.012[47] ALEIXANDRE-TUDO J L, DU TOIT W. Cold maceration application in red wine production and its effects on phenolic compounds: A review [J]. LWT, 2018, 95: 200-208. DOI: 10.1016/j.lwt.2018.04.096[48] UNTERKOFLER J, MUHLACK R, JEFFERY D. Processes and purposes of extraction of grape components during winemaking: current state and perspectives [J]. Applied Microbiology and Biotechnology, 2020, 104: 4737-4755. DOI: 10.1007/s00253-020-10558-3[49] MORATA A. Red wine technology [M]. Academic Press, 2018.[50] BOULTON R. The copigmentation of anthocyanins and its role in the color of red wine: a critical review [J]. American Journal of Enology and Viticulture, 2001, 52(2): 67-87.[51] BROUILLARD R, WIGAND M-C, DANGLES O, et al. pH and solvent effects on the copigmentation reaction of malvin with polyphenols, purine and pyrimidine derivatives [J]. Journal of the Chemical Society, Perkin Transactions 2, 1991, (8): 1235-1241. DOI: https://doi.org/10.1039/P29910001235[52] ZHANG Bo, YANG Xueshan, LI Ningning, et al. Colorimetric study of malvidin-3-O-glucoside copigmented by phenolic compounds: The effect of molar ratio, temperature, pH, and ethanol content on color expression of red wine model solutions [J]. Food Research International, 2017, 102: 468-477. DOI: 10.1016/j.foodres.2017.09.034[53] ZAMORA F. Biochemistry of alcoholic fermentation [M]. Wine Chemistry and Biochemistry. Springer. 2009: 3-26. DOI: 10.1007/978-0-387-74118-5_1[54] COMUZZO P, BATTISTUTTA F. Acidification and pH control in red wines [M]. Red wine technology. Elsevier. 2019: 17-34. DOI: 10.1016/B978-0-12-814399-5.00002-5[55] WATERHOUSE A L, SACKS G L, JEFFERY D W. Non-flavonoid phenolics [M]. Understanding Wine Chemistry. Wiley. 2016: 112-113. DOI: https://doi.org/10.1002/9781118730720.ch13[56] WATERHOUSE A L, SACKS G L, JEFFERY D W. Conversion of variety specific components, Other [M]. Understanding Wine Chemistry. Wiley. 2016: 269-270. DOI: 10.1002/9781118730720.ch23c[57] ABRAHAMSE C E, BARTOWSKY E J. Timing of malolactic fermentation inoculation in Shiraz grape must and wine: influence on chemical composition [J]. World Journal of Microbiology and Biotechnology, 2012, 28(1): 255-265. DOI: 10.1007/s11274-011-0814-3[58] IZQUIERDO-CA?AS P M, GARCíA-ROMERO E, MENA-MORALES A, et al. Effects of malolactic fermentation on colour stability and phenolic composition of Petit Verdot red wines [J]. Wine Studies, 2016, 5(1). DOI: 10.4081/ws.2016.5795[59] BURNS T R, OSBORNE J P. Impact of malolactic fermentation on the color and color stability of pinot noir and merlot wine [J]. American Journal of Enology and Viticulture, 2013, 64(3): 370-377. DOI: 10.5344/ajev.2013.13001[60] MONAGAS M, BARTOLOMé B, GóMEZ-CORDOVéS C. Updated knowledge about the presence of phenolic compounds in wine [J]. Critical Reviews in Food Science and Nutrition, 2005, 45(2): 85-118. DOI: 10.1080/10408690490911710[61] HE Jianjun, LIU Yanxia, PAN Qiuhong, et al. Different anthocyanin profiles of the skin and the pulp of Yan73 (Muscat Hamburg× Alicante Bouschet) grape berries [J]. Molecules, 2010, 15(3): 1141-1153. DOI: 10.3390/molecules15031141[62] SETFORD P, JEFFERY D, GRBIN P, et al. Modelling the mass transfer process of malvidin-3-glucoside during simulated extraction from fresh grape solids under wine-like conditions [J]. Molecules, 2018, 23(9): 2159. DOI: 10.3390/molecules23092159[63] ZHANG Xinke, JEFFERY D W, MUHLACK R A, et al. The effects of copigments, sulfur dioxide and enzyme on the mass transfer process of malvidin-3-glucoside using a modelling approach in simulated red wine maceration scenarios [J]. Food and Bioprocess Processing, 2021, 130: 34-47. DOI: 10.1016/j.fbp.2021.09.001[64] GUADALUPE Z, PALACIOS A, AYESTARáN B. Maceration enzymes and mannoproteins:? a possible strategy to increase colloidal stability and color extraction in red wines [J]. Journal of Agricultural and Food Chemistry, 2007, 55(12): 4854-4862. DOI: 10.1021/jf063585a[65] KELEBEK H, CANBAS A, CABAROGLU T, et al. Improvement of anthocyanin content in the cv. ?küzg?zü wines by using pectolytic enzymes [J]. Food Chemistry, 2007, 105(1): 334-339. DOI: 10.1016/j.foodchem.2006.11.068[66] BIMPILAS A, TSIMOGIANNIS D, BALTA-BROUMA K, et al. Evolution of phenolic compounds and metal content of wine during alcoholic fermentation and storage [J]. Food Chemistry, 2015, 178: 164-171. DOI: 10.1016/j.foodchem.2015.01.090[67] CASASSA L F, BEAVER C W, MIRELES M S, et al. Effect of extended maceration and ethanol concentration on the extraction and evolution of phenolics, color components and sensory attributes of Merlot wines [J]. Australian Journal of Grape and Wine Research, 2013, 19: 25-39. DOI: 10.1111/ajgw.12009[68] ECHEVERRIGARAY S, SCARIOT F J, MENEGOTTO M, et al. Anthocyanin adsorption by Saccharomyces cerevisiae during wine fermentation is associated to the loss of yeast cell wall/membrane integrity [J]. International Journal of Food Microbiology, 2020, 314: 108383. DOI: 10.1016/j.ijfoodmicro.2019.108383[69] MORATA A, GóMEZ-CORDOVéS M, SUBERVIOLA J, et al. Adsorption of anthocyanins by yeast cell walls during the fermentation of red wines [J]. Journal of Agricultural and Food Chemistry, 2003, 51(14): 4084-4088. DOI: 10.1021/jf021134u[70] ZHANG Pangzhen, MA Wen, MENG Yiqi, et al. Wine phenolic profile altered by yeast: Mechanisms and influences [J]. Comprehensive Reviews in Food Science and Food Safety, 2021, 20(4): 3579-3619. DOI: 10.1111/1541-4337.12788[71] YANG Y, DEED R C, ARAUJO L D, et al. Effect of microoxygenation on acetaldehyde, yeast and colour before and after malolactic fermentation on Pinot Noir wine [J]. Australian Journal of Grape and Wine Research, 2022, 28(1): 50-60. DOI: 10.1111/ajgw.12512[72] MORENO-ARRIBAS M, GóMEZ-CORDOVéS C, MARTíN-áLVAREZ P J. Evolution of red wine anthocyanins during malolactic fermentation, postfermentative treatments and ageing with lees [J]. Food Chemistry, 2008, 109(1): 149-158. DOI: 10.1016/j.foodchem.2007.12.040[73] RINALDI A, COPPOLA M, MOIO L. Aging of Aglianico and Sangiovese wine on mannoproteins: Effect on astringency and colour [J]. LWT, 2019, 105: 233-241. DOI: 10.1016/j.lwt.2019.02.034[74] 曹鹏, 张波, 张欣珂, et al. 陈酿前添加咖啡酸对干红葡萄酒颜色品质及多酚构成的影响 [J]. 中国食品学报, 2019, (7), 153-160. DOI:10.16429/j.1009-7848.2019.07.020[75] 王晓月, 张珊珊, 张欣珂, et al. 发酵前添加黄酮醇类辅色素对'赤霞珠'干红葡萄酒颜色品质及多酚组成的影响 [J]. 食品科学, 2020, 41(18), 188-195. DOI:10.7506/spkx1002-6630-20190714-187[76] ZHANG Xinke, LAN Yibin, HUANG Yue, et al. Targeted metabolomics of anthocyanin derivatives during prolonged wine aging: Evolution, color contribution and aging prediction [J]. Food Chemistry, 2021, 339: 127795. DOI: 10.1016/j.foodchem.2020.127795[77] ZHANG Xinke, HE Fei, ZHANG Bo, et al. The effect of prefermentative addition of gallic acid and ellagic acid on the red wine color, copigmentation and phenolic profiles during wine aging [J]. Food Research International, 2018, 106: 568-579. DOI: 10.1016/j.foodres.2017.12.054[78] SANZA M D A, DOMíNGUEZ I N. Wine aging in bottle from artificial systems (staves and chips) and oak woods: Anthocyanin composition [J]. Analytica Chimica Acta, 2006, 563(1): 255-263. DOI: 10.1016/j.aca.2005.11.030[79] DEL áLAMO SANZA M, DOMíNGUEZ I N, MERINO S G. Influence of different aging systems and oak woods on aged wine color and anthocyanin composition [J]. European Food Research and Technology, 2004, 219(2): 124-132. DOI: 10.1007/s00217-004-0930-5[80] ALEIXANDRE-TUDO J, DU TOIT W. Evolution of phenolic composition during barrel and bottle aging [J]. South African Journal of Enology and Viticulture, 2020, 41(2): 233-237. DOI: 10.21548/41-2-4128[81] ECHAVE J, BARRAL M, FRAGA-CORRAL M, et al. Bottle aging and storage of wines: A review [J]. Molecules, 2021, 26(3): 713. DOI: 10.3390/molecules26030713[82] DEL ALAMO-SANZA M, NEVARES I. Oak wine barrel as an active vessel: A critical review of past and current knowledge [J]. Critical Reviews in Food Science and Nutrition, 2017, 2018, 58(16): 2711-2726. DOI: 10.1080/10408398.2017.1330250[83] LAQUI-ESTA?A J, LóPEZ-SOLíS R, PE?A-NEIRA á, et al. Wines in contact with oak wood: the impact of the variety (Carménère and Cabernet Sauvignon), format (barrels, chips and staves), and aging time on the phenolic composition [J]. Journal of the Science of Food and Agriculture, 2019, 99(1): 436-448. DOI: 10.1002/jsfa.9205[84] GAMBUTI A, CAPUANO R, LISANTI M T, et al. Effect of aging in new oak, one-year-used oak, chestnut barrels and bottle on color, phenolics and gustative profile of three monovarietal red wines [J]. European Food Research and Technology, 2010, 231(3): 455-65. DOI: 10.1007/s00217-010-1292-9[85] PFAHL L, CATARINO S, FONTES N, et al. Effect of barrel-to-barrel variation on color and phenolic composition of a red wine [J]. Foods, 2021, 10(7): 1669. DOI: 10.3390/foods10071669[86] DE FREITAS V, MATEUS N. Formation of pyranoanthocyanins in red wines: a new and diverse class of anthocyanin derivatives [J]. Analytical and Bioanalytical Chemistry, 2011, 401(5): 1463-1473. DOI: 10.1007/s00216-010-4479-9[87] FULCRAND H, DOS SANTOS P-J C, SARNI-MANCHADO P, et al. Structure of new anthocyanin-derived wine pigments [J]. Journal of the Chemical Society, Perkin Transactions 1, 1996, (7): 735-739. DOI: 10.1002/chin.199630221[88] SALAS E, FULCRAND H, MEUDEC E, et al. Reactions of anthocyanins and tannins in model solutions [J]. Journal of Agricultural and Food Chemistry, 2003, 51(27): 7951-7961. DOI: 10.1021/jf0345402[89] REMY S, FULCRAND H, LABARBE B, et al. First confirmation in red wine of products resulting from direct anthocyanin–tannin reactions [J]. Journal of the Science of Food and Agriculture, 2000, 80(6): 745-751. DOI: 10.1002/(SICI)1097-0010(20000501)80:6<745::AID-JSFA611>3.0.CO;2-4[90] DUENAS M, FULCRAND H, CHEYNIER V. Formation of anthocyanin–flavanol adducts in model solutions [J]. Analytica Chimica Acta, 2006, 563(1): 15-25. DOI: 10.1016/j.aca.2005.10.062[91] PISSARRA J, LOUREN?O S, GONZáLEZ-PARAMáS A M, et al. Formation of new anthocyanin-alkyl/aryl-flavanol pigments in model solutions [J]. Analytica Chimica Acta, 2004, 513(1): 215-221. DOI: 10.1016/j.aca.2003.09.039[92] ES-SAFI N-E, CHEYNIER V, MOUTOUNET M. Role of aldehydic derivatives in the condensation of phenolic compounds with emphasis on the sensorial properties of fruit-derived foods [J]. Journal of Agricultural and Food Chemistry, 2002, 50(20): 5571-85. DOI: 10.1021/jf025503y[93] MATEUS N, SILVA A M, RIVAS-GONZALO J C, et al. A new class of blue anthocyanin-derived pigments isolated from red wines [J]. Journal of Agricultural and Food Chemistry, 2003, 51(7): 1919-1923. DOI: 10.1021/jf020943a[94] ZHANG Xinke, LI Siyu, ZHAO Xu, et al. HPLC-MS/MS-based targeted metabolomic method for profiling of malvidin derivatives in dry red wines [J]. Food Research International, 2020, 134: 109226. DOI: 10.1016/j.foodres.2020.109226[95] ALCALDE‐EON C, ESCRIBANO‐BAILóN M T, SANTOS‐BUELGA C, et al. Identification of dimeric anthocyanins and new oligomeric pigments in red wine by means of HPLC‐DAD‐ESI/MSn [J]. Journal of Mass Spectrometry, 2007, 42(6): 735-748. DOI: 10.1002/jms.1208[96] DE VILLIERS A, CABOOTER D, LYNEN F, et al. High-efficiency high performance liquid chromatographic analysis of red wine anthocyanins [J]. Journal of Chromatography A, 2011, 1218(29): 4660-4670. DOI: 10.1016/j.chroma.2011.05.042[97] 张欣珂, 赵旭, 成池芳, et al. 葡萄酒中的酚类物质Ⅰ:种类,结构及其检测方法研究进展 [J]. 食品科学, 2019, 40(15): 255-268. DOI: http://www.spkx.net.cn/EN/abstract/abstract48605.shtml[98] HE Fei, LIANG Nana, MU Lin, et al. Anthocyanins and their variation in red wines II. Anthocyanin derived pigments and their color evolution [J]. Molecules, 2012, 17(2): 1483-1519. DOI: 10.3390/molecules17021483[99] QUAGLIERI C, JOURDES M, WAFFO-TEGUO P, et al. Updated knowledge about pyranoanthocyanins: Impact of oxygen on their contents, and contribution in the winemaking process to overall wine color [J]. Trends in Food Science & Technology, 2017, 67: 139-149. DOI: 10.1016/j.tifs.2017.07.005[100] BERRUETA L A, RASINES-PEREA Z, PRIETO-PEREA N, et al. Formation and evolution profiles of anthocyanin derivatives and tannins during fermentations and aging of red wines [J]. European Food Research and Technology, 2020, 246(1): 149-165. DOI: 10.1007/s00217-019-03405-x[101] CHATONNET P, DUBOURDIEU D, BOIDRON J-N, et al. Synthesis of volatile phenols by Saccharomyces cerevisiae in wines [J]. Journal of the Science of Food and Agriculture, 1993, 62(2): 191-202. DOI: 10.1002/jsfa.2740620213[102] MCRAE J M, DAMBERGS R G, KASSARA S, et al. Phenolic compositions of 50 and 30 year sequences of Australian red wines: the impact of wine age [J]. Journal of Agricultural and Food Chemistry, 2012, 60(40): 10093-102. DOI: 10.1021/jf301571q[103] GUYOT S, VERCAUTEREN J, CHEYNIER V. Structural determination of colourless and yellow dimers resulting from (+)-catechin coupling catalysed by grape polyphenoloxidase [J]. Phytochemistry, 1996, 42(5): 1279-1288. DOI: 10.1016/0031-9422(96)00127-6 |
[1] | 张静月,董鹏程,左惠心,梁荣蓉,毛衍伟,张一敏,杨啸吟,罗欣,朱立贤. 白藜芦醇通过SIRT1/PGC-1α影响牛肌管细胞线粒体生物发生和肌纤维类型转化[J]. 食品科学, 2024, 45(4): 1-9. |
[2] | 姜熠,潘学军,洪艳阳,史斌斌,李雪,张文娥. ‘黔核7号’去皮种仁多酚含量、抗氧化活性与多酚代谢关键酶活性的关系分析[J]. 食品科学, 2024, 45(4): 10-17. |
[3] | 黄倩,梁安健,朱鹏程,李东亮,唐俊妮. 魏斯氏菌胞外多糖在发酵食品中的应用进展[J]. 食品科学, 2024, 45(4): 352-359. |
[4] | 裴慧敏,李亚蕾,曹松敏,罗瑞明,毕永昭,伏棋画. 滩羊尾脂共轭亚油酸微胶囊的理化性质及其潜在生物活性评估[J]. 食品科学, 2024, 45(4): 68-76. |
[5] | 张清燕,赵君,张哲,陈雄,姚兰. 葡萄糖对Starmerella bacillaris香草醛耐受能力的影响[J]. 食品科学, 2024, 45(4): 96-107. |
[6] | 周晓,李跑,吴梓仟,唐辉,徐巨才,蒋立文,覃业优,刘洋. 不同黄曲霉菌株强化发酵对浏阳豆豉鲜味形成的影响[J]. 食品科学, 2024, 45(4): 116-124. |
[7] | 毛凤娇,黄均,周荣清,张宿义,秦辉. 人工窖泥微生物群落对浓香型白酒发酵过程风味代谢物形成的影响[J]. 食品科学, 2024, 45(4): 125-134. |
[8] | 王迎,董明盛,张国强,韩月峰. 红茶菌发酵对天麻活性成分及感官品质的影响[J]. 食品科学, 2024, 45(4): 232-238. |
[9] | 曹汝鸽,武小晖,黄文达. 微波处理对大米储藏过程中脂质变化的影响[J]. 食品科学, 2024, 45(4): 247-256. |
[10] | 何静怡,魏涯,岑剑伟,郝淑贤,陈胜军,黄卉,赵永强,王悦齐,杨少玲,林织. 基于梯度降温的草鱼暂养及有水保活运输技术[J]. 食品科学, 2024, 45(4): 271-278. |
[11] | 王芷静,陈倩茜,蔡杰. 淀粉-多酚复合膜的研究进展:从功能特性到食品包装应用[J]. 食品科学, 2024, 45(4): 336-343. |
[12] | 刘芬芬,蒲首丞,赵雯靓,王怡婷,薛琛,徐丽珊. 金花茶花对2型糖尿病小鼠的降糖及抗氧化作用[J]. 食品科学, 2024, 45(3): 94-101. |
[13] | 张艳艳,张斯琦,孙萌辉,刘兴丽,张华. 磁场处理对面团发酵特性的影响及作用机制[J]. 食品科学, 2024, 45(3): 110-116. |
[14] | 何近刚,冯云霄,程玉豆,关军锋. 采前氨基乙氧基乙烯甘氨酸处理对‘黄冠’梨长期冷藏后果实品质和果心褐变的影响[J]. 食品科学, 2024, 45(3): 159-166. |
[15] | 张乐,崔金娜,刘伟,朱明达,刘占英. 酿酒酵母耐受机制研究进展[J]. 食品科学, 2024, 45(3): 317-325. |
阅读次数 | ||||||
全文 |
|
|||||
摘要 |
|
|||||