综述与专题评论

葡萄酒中挥发性硫化物及其分析方法的研究进展

  • 谭凤玲 ,
  • 褚瑞超 ,
  • 司梦雅 ,
  • 王宝石 ,
  • 张明霞
展开
  • (河南科技学院 生命科技学院,现代生物育种河南省协同创新中心, 河南 新乡,453003)
硕士研究生(王宝石博士和张明霞教授为共同通讯作者,E-mail:wangbaoshifsd@126.com;zhangmingx@163.com)

收稿日期: 2020-10-09

  修回日期: 2020-11-03

  网络出版日期: 2021-06-17

Research progress of volatile sulfur compounds in wine and their analysis methods

  • TAN Fengling ,
  • CHU Ruichao ,
  • SI Mengya ,
  • WANG Baoshi ,
  • ZHANG Mingxia
Expand
  • (School of Life Science and Technology, Henan Collaborative Innovation Center in Modern Biological Breeding, Henan Institute of Science and Technology, Xinxiang 453003, China)

Received date: 2020-10-09

  Revised date: 2020-11-03

  Online published: 2021-06-17

摘要

成品葡萄酒中含有痕量的挥发性硫化物(volatile sulfur compounds,VSCs),如硫醇、硫化氢、硫醚、硫醇酯、含硫杂醇油及杂环化合物等,这些硫化物对葡萄酒的香气、颜色和口感等感官品质产生重要影响。该文从挥发性硫化物来源、感官特性及其分析方法等视角系统分析了葡萄酒中VSCs的最新研究进展。近年来,气相色谱-质谱联用和高效液相色谱-质谱联用在VSCs检测中发挥了重要作用;但由于葡萄酒基质复杂,VSCs存在挥发性强、稳定性差和检测阈值低等难题,亟待开发高效、便捷的复杂样品中VSCs检测方法,以期为有效控制与调控葡萄酒中VSCs,创制高品质葡萄酒提供参考。

本文引用格式

谭凤玲 , 褚瑞超 , 司梦雅 , 王宝石 , 张明霞 . 葡萄酒中挥发性硫化物及其分析方法的研究进展[J]. 食品与发酵工业, 2021 , 47(10) : 297 -303 . DOI: 10.13995/j.cnki.11-1802/ts.025786

Abstract

Trace amounts of volatile sulfide compounds (VSCs), such as mercaptan, hydrogen sulfide, thioether, mercaptan ester, sulfur-containing fuel oil, and heterocyclic compounds, are found in wine. These VSCs have an important influence on the aroma, color, and taste of wines. This paper systematically analyzes the latest research progress of VSCs in wine from the perspective of source, sensory characteristics and analysis methods. Recently, gas chromatography-mass spectrometry and high-performance liquid chromatography-mass spectrometry have played an important role in the detection of VSCs. However, due to the complexity of wine substrates, the difficulties of VSCs detection, such as high volatility, poor stability and low detection threshold, so it is urgent to develop efficient and convenient detection methods for VSCs in complex samples. This review aims to provide reference for the effective control and regulation of VSCs in wine and the development of high-quality wines.

参考文献

[1] KINZURIK M I, DEED R C, HERBST-JOHNSTONE M, et al.Addition of volatile sulfur compounds to yeast at the early stages of fermentation reveals distinct biological and chemical pathways for aroma formation[J].Food Microbiology, 2020, 89:103 435.
[2] JO Y, CARTER B G, BARBANO D M, et al.Identification of the source of volatile sulfur compounds produced in milk during thermal processing[J].Journal of Dairy Science, 2019, 102(10):8 658-8 669.
[3] YE D Q, ZHENG X T, XU X Q, et al.Evolutions of volatile sulfur compounds of Cabernet Sauvignon wines during aging in different oak barrels[J].Food Chemistry, 2016, 202:236-246.
[4] ARAUJO L D, VANNEVEL S, BUICA A, et al.Indications of the prominent role of elemental sulfur in the formation of the varietal thiol 3-mercaptohexanol in Sauvignon blanc wine[J].Food Research International, 2017, 98:79-86.
[5] BEKKER M Z, WILKES E N, SMITH P A.Evaluation of putative precursors of key ′reductive′ compounds in wines post-bottling[J].Food Chemistry, 2018, 245:676-686.
[6] BEKKER M Z, MIERCZYNSKA-VASILEV A, SMITH P A, et al.The effects of pH and copper on the formation of volatile sulfur compounds in Chardonnay and Shiraz wines post-bottling[J].Food Chemistry, 2016, 207:148-156.
[7] TUFARIELLO M, PATI S, D′AMICO L, et al.Quantitative issues related to the headspace-SPME-GC/MS analysis of volatile compounds in wines:The case of Maresco sparkling wine[J].LWT-Food Science and Technology, 2019, 108:268-276.
[8] CHEN L, CAPONE D L, NICHOLSON E L, et al.Investigation of intraregional variation, grape amino acids, and pre-fermentation freezing on varietal thiols and their precursors for Vitis vinifera Sauvignon blanc[J].Food Chemisty, 2019, 295:637-645.
[9] SANTIAGO M, GARDNER R C.Yeast genes required for conversion of grape precursors to varietal thiols in wine[J].FEMS Yeast Research, 2015, 15(5):34.
[10] HERDERICH M J, FRANCIS I L, UGLIANO M, et al.Analysis and formation of key sulfur aroma compounds in wine[J].ACS Symposium Series, 2011, 1 068:267-286.
[11] FRANCO-LUESMA E, SÁENZ-NAVAJAS M P, VALENTIN D, et al.Study of the effect of H2S, MeSH and DMS on the sensory profile of wine model solutions by Rate-All-That-Apply (RATA)[J].Food Research International, 2016, 87:152-160.
[12] JASTRZEMBSKI J A, ALLISON R B, FRIEDBERG E, et al.Role of elemental sulfur in forming latent precursors of H2S in wine[J].Journal of Agricultural and Food Chemistry, 2017, 65(48):10 542-10 549.
[13] PATRIGNANI F, CHINNICI F, SERRAZANETTI D I, et al.Production of volatile and sulfur compounds by 10 Saccharomyces cerevisiae strains inoculated in trebbiano must[J].Frontiers in Microbiology, 2016, 7:243.
[14] LANDAUD S, HELINCK S, BONNARME P.Formation of volatile sulfur compounds and metabolism of methionine and other sulfur compounds in fermented food[J].Applied Microbiology and Biotechnology, 2008, 77(6):1 191-1 205.
[15] MESTRES M, BUSTO O, GUASCH J.Analysis of organic sulfur compounds in wine aroma[J].Journal of Chromatography A, 2000, 881(1-2):569-581.
[16] MENN N L, LEEUWEN C V, PICARD M, et al.Effect of vine water and nitrogen status, as well as temperature, on some aroma compounds of aged red bordeaux wines[J].Journal of Agricultural and Food Chemistry, 2019, 67(25):7 098-7 109.
[17] DEED R C, PILKINGTON L I, HERBST-JOHNSTONE M, et al.A new analytical method to measure S-methyl-l-methionine in grape juice reveals the influence of yeast on dimethyl sulfide production during fermentation[J].Journal of the Science of Food and Agriculture, 2019, 99(15):6 944-6 953.
[18] CAPONE D L, RISTIC R, PARDON K H, et al.Simple quantitative determination of potent thiols at ultratrace levels in wine by derivatization and high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) analysis[J].Analytical Chemistry, 2015, 87(2):1 226-1 231.
[19] 马捷, 刘延琳.葡萄酒中重要挥发性硫化物的代谢及基因调控[J].微生物学报, 2011, 51(1):14-20.
MA J, LIU Y L.Metabolism and gene regulation of important volatile sulfur compounds in wine-A review[J].Acta Microbiologica Sinica, 2011, 51(1):14-20.
[20] KINZURIK M I, HERBST-JOHNSTONE M, GARDNER R C, et al.Hydrogen sulfide production during yeast fermentation causes the accumulation of ethanethiol, S-ethyl thioacetate and diethyl disulfide[J].Food Chemistry, 2016, 209:341-347.
[21] KINZURIK M I, HERBST-JOHNSTONE M, GARDNER R C, et al.Evolution of volatile sulfur compounds during wine fermentation[J].Journal of Agricultural and Food Chemistry, 2015, 63(36):8 017-8 024.
[22] FERREIRA V, FRANCO-LUESMA E, VELA E, et al.Elusive chemistry of hydrogen sulfide and mercaptans in wine[J].Journal of Agricultural and Food Chemistry, 2018, 66(10):2 237-2 246.
[23] LYTRA G, TEMPERE S, MARCHAND S, et al.How do esters and dimethyl sulphide concentrations affect fruity aroma perception of red wine? Demonstration by dynamic sensory profile evaluation[J].Food Chemistry, 2016, 194:196-200.
[24] PICARD M, THIBON C, REDON P, et al.Involvement of dimethyl sulfide and several polyfunctional thiols in the aromatic expression of the aging bouquet of red bordeaux wines[J].Journal of Agricultural and Food Chemistry, 2015, 63(40):8 879-8 889.
[25] WANG C X, LIU M L, LI Y, et al.Hydrogen sulfide synthesis in native Saccharomyces cerevisiae strains during alcoholic fermentations[J].Food Microbiology, 2018, 70:206-213.
[26] 魏阳吉, 马丽艳, 李景明.葡萄酒中硫化氢检测方法的研究[J].酿酒科技, 2010(2):109-111.
WEI Y J, MA L Y, LI J M.Determination method of hydrogen sulfide content in grape wine[J].Liquor-Making Science and Technology, 2010(2):109-111.
[27] 逢晓薇, 孙辉, 武锋, 等.两种葡萄酒中二氧化硫检测方法研究[J].酿酒科技, 2018(6):91-99.
PENG X W, SUN H, WU F, et al.Comparisonof the two determination methods of sulfur dioxide in grapewine[J].Liquor-Making Science and Technology, 2018(6):91-99.
[28] 周霞, 孙芬芳, 张玲玲, 等.半微量碘量法测定葡萄酒中总二氧化硫含量[J].食品与发酵工业, 2019, 45(7):284-287.
ZHOU X, SUN F F, ZHANG L L, et al.Determination of total sulfur dioxide in grape wine by semi- micro iodimetric analysis[J].Food and Fermentation Industries, 2019, 45(7):284-287.
[29] CHEN Y, LI J, HOU X L, et al.Trapping and preconcentration of volatile organic sulfur compounds in water samples by portable and battery-powered trapping device prior to gas chromatography-sulfur chemiluminescence determination[J].Journal of Chromatography A, 2020, 1 619:460 947.
[30] TOLEDO M, GUILLOT J M, SILES J A, et al.Permeability and adsorption effects for volatile sulphur compounds in Nalophan sampling bags:Stability influenced by storage time[J].Biosystems Engineering, 2019, 188:217-228.
[31] CHENOT C, BRIFFOZ L, LOMARTIRE A, et al.Occurrence of ehrlich-derived and varietal polyfunctional thiols in belgian white wines made from chardonnay and solaris grapes[J].Journal of Agricultural and Food Chemistry, 2019, 68(38):10 310-10 317.
[32] DU X F, SONG M, BALDWIN E, et al.Identification of sulphur volatiles and GC-olfactometry aroma profiling in two fresh tomato cultivars[J].Food Chemistry, 2015, 171:306-314.
[33] PEÑALVER R, CAMPILLO N, LÓPEZ-GARCÍA I, et al.Solid-phase microextraction for the determination of iron organic compounds in seawaters and soils by gas chromatography coupled to microwave-induced plasma with atomic emission detection spectrometry[J].Microchemical Journal, 2020, 154:104 630.
[34] HART R S, JOLLY N P, NDIMBA B K.Characterisation of hybrid yeasts for the production of varietal Sauvignon blanc wine - A review[J].Journal of Microbiological Methods, 2019, 165:105 699.
[35] FARHADI F, IRANSHAHI M, TAGHIZADEH S F, et al.Volatile sulfur compounds:The possible metabolite pattern to identify the sources and types of asafoetida by headspace GC/MS analysis[J].Industrial Crops and Products, 2020, 155:112 827.
[36] TOMINAGA T, DUBOURDIEU D.A novel method for quantification of 2-methyl-3-furanthiol and 2- uranmethanethiol in wines made from vitis vinifera grape varieties[J].Journal of Agricultural and Food Chemistry, 2006, 54(1):29-33.
[37] CAPONE D L, SEFTON M A, JEFFERY D W.Application of a modified method for 3-mercaptohexan-1-ol determination to investigate the relationship between free thiol and related conjugates in grape juice and wine[J].Journal of Agricultural and Food Chemistry, 2011, 59(9):4 649-4 658.
[38] CANNON R J, HO C T.Volatile sulfur compounds in tropical fruits[J].Journal of Food and Drug Analysis, 2018, 26(2):445-468.
[39] DYMERSKI T.Two-dimensional gas chromatography coupled with mass spectrometry in food analysis[J].Critical Reviews in Analytical Chemistry, 2018, 48(4):252-278.
[40] YAN Y, CHEN S, NIE Y, et al.Characterization of volatile sulfur compounds in soy sauce aroma type Baijiu and changes during fermentation by GC×GC-TOFMS, organoleptic impact evaluation, and multivariate data analysis[J].Food Research International, 2020, 131:109 043.
[41] AL-DALALI S, ZHENG F P, SUN B G, et al.Effects of different brewing processes on the volatile flavor profiles of Chinese vinegar determined by HS-SPME-AEDA with GC-MS and GC-O[J].LWT-Food Science and Technology, 2020, 133:109 969.
[42] AL-DALALI S, ZHENG F P, SUN B G, et al.Comparison of aroma profiles of traditional and modern zhenjiang aromatic vinegars and their changes during the vinegar aging by SPME-GC-MS and GC-O[J].Food Analytical Methods, 2018, 12(2):544-557.
[43] SONG H L, LIU J B.GC-O-MS technique and its applications in food flavor analysis[J].Food Research International, 2018, 114:187-198.
[44] VILLIÈRE A, SYMONEAUX R, ROCHE A, et al.Comprehensive sensory and chemical data on the flavor of 16 red wines from two varieties:Sensory descriptive analysis, HS-SPME-GC-MS volatile compounds quantitative analysis, and odor-active compounds identification by HS-SPME-GC-MS-O[J].Data in Brief, 2019, 24:103 725.
[45] LAJIN B, GOESSLER W.Exploring the sulfur species in wine by HPLC-ICPMS/MS[J].Analytica Chimica Acta, 2019, 1 092:1-8.
[46] 陈文硕, 崔颖, 王淞, 等.连续流动分析仪法测定葡萄酒中总二氧化硫[J].食品研究与开发, 2017, 38(11):158-160.
CHEN W S, CUI Y, WANG S, et al.Determination of total sulfur dioxide in wine with continous flow analyzer method[J].Food Research and Development, 2017, 38(11):158-160.
[47] MANDRILE L, CAGNASSO I, BERTA L, et al.Direct quantification of sulfur dioxide in wine by surface enhanced raman spectroscopy[J].Food Chemistry, 2020, 326:127 009.
[48] NIU Y W, YAO Z M, XIAO Q, et al.Characterization of the key aroma compounds in different light aroma type Chinese liquors by GC-olfactometry, GC-FPD, quantitative measurements, and aroma recombination[J].Food Chemistry, 2017, 233:204-215.
[49] VELA E, HERNANDEZ-ORTE P, FRANCO-LUESMA E, et al.Micro-oxygenation does not eliminate hydrogen sulfide and mercaptans from wine;it simply shifts redox and complex-related equilibria to reversible oxidized species and complexed forms[J].Food Chemistry, 2018, 243:222-230.
[50] CAMPILLO N, PEÑALVER R, LÓPEZ-GARCÍA I, et al.Headspace solid-phase microextraction for the determination of volatile organic sulphur and selenium compounds in beers, wines and spirits using gas chromatography and atomic emission detection[J].Journal of Chromatography A, 2009, 1 216(39):6 735-6 740.
[51] SLAGHENAUFI D, TONIDANDEL L, MOSER S, et al.Rapid analysis of 27 volatile sulfur compounds in wine by headspace solid-phase microextraction gas chromatography tandem mass spectrometry[J].Food Analytical Methods, 2017, 10(11):3 706-3 715.
[52] ONTANON I, VELA E, HERNANDEZ-ORTE P, et al.Gas chromatographic-sulfur chemiluminescent detector procedures for the simultaneous determination of free forms of volatile sulfur compounds including sulfur dioxide and for the determination of their metal-complexed forms[J].Journal of Chromatography A, 2019, 1 596:152-160.
[53] ZHOU Z L, JIAN D Z, GONG M, et al.Characterization of the key aroma compounds in aged Zhenjiang aromatic vinegar by gas chromatography-olfactometry-mass spectrometry, quantitative measurements, aroma recombination and omission experiments[J].Food Research International, 2020, 136:109 434.
文章导航

/