食品中挥发性硫化物的研究进展
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摘要
挥发性硫化合物对食品中的特征风味或异味的产生具有重要的影响。该文综述了食品中挥发性硫化物的主要结构类型、性质、生成路径、提取方法和分析检测技术及其感官特性,为食品的风味特性、异味的研究及硫化物的深度开发利用提供参考。
Volatile sulfur compounds( VSCs) have significant effects on characteristic flavors or off-flavor of many foods. The main structures,properties,synthesis paths,extraction methods,analysis methods,and sensory characteristics of VSCs in foods were reviewed. It can offer references for studying flavor characteristics and off-flavor of foods as well as exploiting the development and use of sulfide further.
Volatile sulfur compounds( VSCs) have significant effects on characteristic flavors or off-flavor of many foods. The main structures,properties,synthesis paths,extraction methods,analysis methods,and sensory characteristics of VSCs in foods were reviewed. It can offer references for studying flavor characteristics and off-flavor of foods as well as exploiting the development and use of sulfide further.
引文
[1]ENGEL E,MARTIN N,ISSANCHOU S.Sensitivity to allyl isothiocyanate,dimethyl trisulfide,sinigrin,and cooked cauliflower consumption[J].Appetite,2006,46(3):263-269.
[2]DU Xiao-Fen,SONG Mei,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.
[3]张晓林,刘萍.大蒜有机硫化物的研究进展[J].医学综述,2011(3):432-434.
[4]WERKHOFF P,GUNTERT M,KRAMMER G,et al.Vacuum headspace method in aroma research:Flavor chemistry of yellow passion fruits[J].Journal of Agricultural and Food Chemistry,1998,46(3):1 076-1 093.
[5]DU Xiao-Fen,WHITAKER V,ROUSEFF R.Changes in strawberry volatile sulfur compounds due to genotype,fruit maturity and sample preparation[J].Flavour and Fragrance Journal,2012,27(6):398-404.
[6]JUNG K,FASTOWSKI O,ENGEL K H.Occurrence of 4-methoxy-2-methyl-2-butanethiol in blackcurrant(Ribes nigrum L.)berries[J].Flavour and Fragrance Journal,2016,31(6):438-441.
[7]WITHYCOMBE D A,MUSSINAN C J.Identification of 2-methyl-3-furanthiol in the steam distillate from canned tuna fish[J].Journal of Food Science,1988,53(2):658.
[8]HILL R W,DACEY J W H,HILL S D,et al.Dimethylsulfoniopropionate in six species of giant clams and the evolution of dimethylsulfide after death[J].Canadian Journal of Fisheries and Aquatic Sciences,2004,61(5):758-764.
[9]SUN Zheng-Chun,HAYAT K,YU Jiang-Yang,et al.Quantification of free 2-furfurylthiol in coffee brew using a prefabricated coffee model[J].Food Analytical Methods,2018,11(3):654-662.
[10]RODRIGUES H,SAENZ-NAVAJAS M-P,FRANCO-LU-ESMA E,et al.Sensory and chemical drivers of wine minerality aroma:An application to Chablis wines[J].Food Chemistry,2017,230:553-562.
[11]BLANK I.Sensory relevance of volatile organic sulfur compounds in food[J].Acs Symposium,2002,826:25-53.
[12]VERMEULEN C,GIJS L,COLLIN S.Sensorial contribution and formation pathways of thiols in foods:A review[J].Food Reviews International,2005,21(1):69-137.
[13]MUELLER C,HOFMANN T.Quantitative studies on the formation of phenol/2-furfurylthiol conjugates in coffee beverages toward the understanding of the molecular mechanisms of coffee aroma staling[J].Journal of Agricultural and Food Chemistry,2007,55(10):4 095-4 102.
[14]DREHER J G,ROUSEFF R,NAIM M.GC-olfactometric characterization of aroma volatiles from the thermal degradation of thiamin in model orange juice[J].Journal of Agricultural and Food Chemistry,2003,51(10):3 097-3 102.
[15]MURAT M L,MASNEUF I,DARRIET P,et al.Effect of Saccharomyces cerevisiae yeast strains on the liberation of volatile thiols in Sauvignon blanc wine[J].American Journal of Enology and Viticulture,2001,52(2):136-139.
[16]HALL D I,SMITH I K.Partial-purification and characterization of cystine lyase from cabbage(brassicaoleracea-var-capitata)[J].Plant Physiology,1983,72(3):654-658.
[17]BLOCK E.The organosulfur chemistry of the genus allium-implications for the organic-chemistry of sulfur[J].Angewandte Chemie-International Edition,1992,31(9):1 135-1 178.
[18]GRANT-PREECE P,BARRIL C,SCHMIDTKE L M,et al.Light-induced changes in bottled white wine and underlying photochemical mechanisms[J].Critical Reviews in Food Science and Nutrition,2017,57(4):743-754.
[19]MAUJEAN A,SEGUIN N.Sunlight flavors in champagne wines.3.photochemical-reactions responsible for sunlight flavors in champagne wine[J].Sciences Des Aliments,1983,3(4):589-601.
[20]AMES J M.Effect of p H and temperature on the formation of volatile compounds in cysteine/reducing sugar/starch mixtures during extrusion cooking[J].Journal of Agricultural and Food Chemistry,2001,49(4):1 885-1 894.
[21]SCHIEBERLE P,HOFMANN T.Characterization of key odorants in dry-heated cysteine/carbohydrate mixturesComparison with aqueous reaction systems[J].Abstracts of Papers of the American Chemical Society,1997,705:320-330.
[22]ENGEL W,SCHIEBERLE P.Identification and quantitation of key aroma compounds formed in Maillard-type reactions of fructose with cysteamine or isothiaproline(1,3-thiazolidine-2-carboxylic acid)[J].Journal of Agricultural and Food Chemistry,2002,50(19):5 394-5 399.
[23]PRIPISNICOLAU L,REVEL GD,BERTRAND A,et al.Formation of flavor components by the reaction of amino acid and carbonyl compounds in mild conditions[J].Journal of Agricultural and Food Chemistry,2000,48(9):3761-3 766.
[24]MARCHAND S,REVEL G,BERTRAND A.Approaches to wine aroma:Release of aroma compounds from reactions between cysteine and carbonyl compounds in wine[J].Journal of Agricultural and Food Chemistry,2000,48(10):4 890-4 895.
[25]DWIVEDI B K,ARNOLD R G.chemistry of thiamine degradation in food products and model systems-review[J].Journal of Agricultural and Food Chemistry,1973,21(1):54-60.
[26]HOFMANN T,SCHIEBERLE P.Quantitative model studies on the effectiveness of different precursor systems in the formation of the intense food odorants 2-furfurylthiol and 2-methyl-3-furanthiol[J].Journal of Agricultural and Food Chemistry,1998,46(1):235-241.
[27]MUNCH P,SCHIEBERLE P.Quantitative studies on the formation of key odorants in thermally treated yeast extracts using stable isotope dilution assays[J].Journal of Agricultural and Food Chemistry,1998,46(11):4 695-4 701.
[28]BUTTERY R G,HADDON W F,SEIFERT R M,et al.thiamin odor and bis(2-methyl-3-furyl)disulfide[J].Journal of Agricultural and Food Chemistry,1984,32(3):674-676.
[29]JEZUSSEK M,JULIANO B O,SCHIEBERLE P.Comparison of key aroma compounds in cooked brown rice varieties based on aroma extract dilution analyses[J].Journal of Agricultural and Food Chemistry,2002,50(5):1 101-1 105.
[30]JUNG M Y,YOON S H,LEE H O,et al.Singlet oxygen and ascorbic acid effects on dimethyl disulfide and offflavor in skim milk exposed to light[J].Journal of Food Science,1998,63(3):408-412.
[31]HOLSCHER W,VITZTHUM O G,STEINHART H.prenyl alcohol source for odorants in roasted coffee[J].Journal of Agricultural and Food Chemistry,1992,40(4):655-658.
[32]YOO S R,PRAKASH S M,MIN D B.Off-odor study with gamma-irradiated orange juice using sensory and volatile compound analyses[J].Journal of Food Science,2003,68(4):1 259-1 264.
[33]BURBANK H M,QIAN M C.Volatile sulfur compounds in Cheddar cheese determined by headspace solid-phase microextraction and gas chromatograph-pulsed flame photometric detection[J].Journal of Chromatography A,2005,1066(1-2):149-157.
[34]PELUSIO F,NILSSON T,MONTANARELL L,et al.headspace solid-phase microextraction analysis of volatile organic sulfur-compounds in black-and-white truffle aroma[J].Journal of Agricultural and Food Chemistry,1995,43(8):2 138-2 143.
[35]LESTREMAU F,ANDERSSON F A T,DESAUZIERS V.Investigation of artefact formation during analysis of volatile sulphur compounds using solid phase microextraction(SPME)[J].Chromatographia,2004,59(9-10):607-613.
[36]JABALPURWALA F,GURBUZ O,ROUSEFF R.Analysis of grapefruit sulphur volatiles using SPME and pulsed flame photometric detection[J].Food Chemistry,2010,120(1):296-303.
[37]SPANIER A M,BOYLSTON T D.Effect of temperature on the analysis of beef flavor volatiles-focus on carbonyl and sulfur-containing-compounds[J].Food Chemistry,1994,50(3):251-259.
[38]SUMITANI H,SUEKANE S,SAKAI Y,et al.FPD-GCdetermination of S-methylmethioninesulfonium in satsuma mandarin juice[J].Agricultural and Biological Chemistry,2014,55(11):2 899-2 900.
[39]ALLEGRONE G,BELLIARDO F,CABELLA P.Comparison of volatile concentrations in hand-squeezed juices of four different lemon varieties[J].Journal of Agricultural and Food Chemistry,2006,54(5):1 844-1 848.
[40]MAHATTANATAWEE K,ROUSEFF R L.Comparison of aroma active and sulfur volatiles in three fragrant rice cultivars using GC-olfactometry and GC-PFPD[J].Food Chemistry,2014,154:1-6.
[41]LEHMANN D,DIETRICH A,HENER U,et al.stereoisomeric flavor compounds.LXX:1-p-menthene-8-thiolseparation and sensory evaluation of the enantiomers by enantioselective gas-chromatography olfactometry[J].Phytochemical Analysis,1995,6(5):255-257.
[42]WEBER B,MAAS B,MOSANDL A.stereoisomeric flavor compounds.72.stereoisomeric distribution of some chiral sulfur-containing trace components of yellow passion fruits[J].Journal of Agricultural and Food Chemistry,1995,43(9):2 438-2 441.
[43]ANNESS B J,BAMFORTH C W.Dimethyl sulfide-A review[J].Journal of the Institute of Brewing,1982,88(4):244-252.
[44]PEREZ-CACHO P R,MAHATTANATAWEE K,SMOOTK M,et al.Identification of sulfur volatiles in canned orange juices lacking orange flavor[J].Journal of Agricultural and Food Chemistry,2007,55(14):5 761-5 767.
[45]LI Jia-Xiao,SCHIEBERLE P,STEINHAUS M.Development of stable isotope dilution assays for the quantitation of the food odorants hydrogen sulphide,methanethiol,ethanethiol,and propane-1-thiol and application to durian(Durio zibethinus L.)pulp[J].European Food Research and Technology,2017,243(1):69-79.
[46]THOMAS B,ROTHE M.Aromasto e des brotes[J].Z.Lebensm.Unters.Forsch,1963,119:302-310.
[47]GOMEZ-MIGUEZ M J,CACHO J F,FERREIRA V,et al.Volatile components of Zalema white wines[J].Food Chemistry,2007,100(4):1 464-1 473.
[2]DU Xiao-Fen,SONG Mei,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.
[3]张晓林,刘萍.大蒜有机硫化物的研究进展[J].医学综述,2011(3):432-434.
[4]WERKHOFF P,GUNTERT M,KRAMMER G,et al.Vacuum headspace method in aroma research:Flavor chemistry of yellow passion fruits[J].Journal of Agricultural and Food Chemistry,1998,46(3):1 076-1 093.
[5]DU Xiao-Fen,WHITAKER V,ROUSEFF R.Changes in strawberry volatile sulfur compounds due to genotype,fruit maturity and sample preparation[J].Flavour and Fragrance Journal,2012,27(6):398-404.
[6]JUNG K,FASTOWSKI O,ENGEL K H.Occurrence of 4-methoxy-2-methyl-2-butanethiol in blackcurrant(Ribes nigrum L.)berries[J].Flavour and Fragrance Journal,2016,31(6):438-441.
[7]WITHYCOMBE D A,MUSSINAN C J.Identification of 2-methyl-3-furanthiol in the steam distillate from canned tuna fish[J].Journal of Food Science,1988,53(2):658.
[8]HILL R W,DACEY J W H,HILL S D,et al.Dimethylsulfoniopropionate in six species of giant clams and the evolution of dimethylsulfide after death[J].Canadian Journal of Fisheries and Aquatic Sciences,2004,61(5):758-764.
[9]SUN Zheng-Chun,HAYAT K,YU Jiang-Yang,et al.Quantification of free 2-furfurylthiol in coffee brew using a prefabricated coffee model[J].Food Analytical Methods,2018,11(3):654-662.
[10]RODRIGUES H,SAENZ-NAVAJAS M-P,FRANCO-LU-ESMA E,et al.Sensory and chemical drivers of wine minerality aroma:An application to Chablis wines[J].Food Chemistry,2017,230:553-562.
[11]BLANK I.Sensory relevance of volatile organic sulfur compounds in food[J].Acs Symposium,2002,826:25-53.
[12]VERMEULEN C,GIJS L,COLLIN S.Sensorial contribution and formation pathways of thiols in foods:A review[J].Food Reviews International,2005,21(1):69-137.
[13]MUELLER C,HOFMANN T.Quantitative studies on the formation of phenol/2-furfurylthiol conjugates in coffee beverages toward the understanding of the molecular mechanisms of coffee aroma staling[J].Journal of Agricultural and Food Chemistry,2007,55(10):4 095-4 102.
[14]DREHER J G,ROUSEFF R,NAIM M.GC-olfactometric characterization of aroma volatiles from the thermal degradation of thiamin in model orange juice[J].Journal of Agricultural and Food Chemistry,2003,51(10):3 097-3 102.
[15]MURAT M L,MASNEUF I,DARRIET P,et al.Effect of Saccharomyces cerevisiae yeast strains on the liberation of volatile thiols in Sauvignon blanc wine[J].American Journal of Enology and Viticulture,2001,52(2):136-139.
[16]HALL D I,SMITH I K.Partial-purification and characterization of cystine lyase from cabbage(brassicaoleracea-var-capitata)[J].Plant Physiology,1983,72(3):654-658.
[17]BLOCK E.The organosulfur chemistry of the genus allium-implications for the organic-chemistry of sulfur[J].Angewandte Chemie-International Edition,1992,31(9):1 135-1 178.
[18]GRANT-PREECE P,BARRIL C,SCHMIDTKE L M,et al.Light-induced changes in bottled white wine and underlying photochemical mechanisms[J].Critical Reviews in Food Science and Nutrition,2017,57(4):743-754.
[19]MAUJEAN A,SEGUIN N.Sunlight flavors in champagne wines.3.photochemical-reactions responsible for sunlight flavors in champagne wine[J].Sciences Des Aliments,1983,3(4):589-601.
[20]AMES J M.Effect of p H and temperature on the formation of volatile compounds in cysteine/reducing sugar/starch mixtures during extrusion cooking[J].Journal of Agricultural and Food Chemistry,2001,49(4):1 885-1 894.
[21]SCHIEBERLE P,HOFMANN T.Characterization of key odorants in dry-heated cysteine/carbohydrate mixturesComparison with aqueous reaction systems[J].Abstracts of Papers of the American Chemical Society,1997,705:320-330.
[22]ENGEL W,SCHIEBERLE P.Identification and quantitation of key aroma compounds formed in Maillard-type reactions of fructose with cysteamine or isothiaproline(1,3-thiazolidine-2-carboxylic acid)[J].Journal of Agricultural and Food Chemistry,2002,50(19):5 394-5 399.
[23]PRIPISNICOLAU L,REVEL GD,BERTRAND A,et al.Formation of flavor components by the reaction of amino acid and carbonyl compounds in mild conditions[J].Journal of Agricultural and Food Chemistry,2000,48(9):3761-3 766.
[24]MARCHAND S,REVEL G,BERTRAND A.Approaches to wine aroma:Release of aroma compounds from reactions between cysteine and carbonyl compounds in wine[J].Journal of Agricultural and Food Chemistry,2000,48(10):4 890-4 895.
[25]DWIVEDI B K,ARNOLD R G.chemistry of thiamine degradation in food products and model systems-review[J].Journal of Agricultural and Food Chemistry,1973,21(1):54-60.
[26]HOFMANN T,SCHIEBERLE P.Quantitative model studies on the effectiveness of different precursor systems in the formation of the intense food odorants 2-furfurylthiol and 2-methyl-3-furanthiol[J].Journal of Agricultural and Food Chemistry,1998,46(1):235-241.
[27]MUNCH P,SCHIEBERLE P.Quantitative studies on the formation of key odorants in thermally treated yeast extracts using stable isotope dilution assays[J].Journal of Agricultural and Food Chemistry,1998,46(11):4 695-4 701.
[28]BUTTERY R G,HADDON W F,SEIFERT R M,et al.thiamin odor and bis(2-methyl-3-furyl)disulfide[J].Journal of Agricultural and Food Chemistry,1984,32(3):674-676.
[29]JEZUSSEK M,JULIANO B O,SCHIEBERLE P.Comparison of key aroma compounds in cooked brown rice varieties based on aroma extract dilution analyses[J].Journal of Agricultural and Food Chemistry,2002,50(5):1 101-1 105.
[30]JUNG M Y,YOON S H,LEE H O,et al.Singlet oxygen and ascorbic acid effects on dimethyl disulfide and offflavor in skim milk exposed to light[J].Journal of Food Science,1998,63(3):408-412.
[31]HOLSCHER W,VITZTHUM O G,STEINHART H.prenyl alcohol source for odorants in roasted coffee[J].Journal of Agricultural and Food Chemistry,1992,40(4):655-658.
[32]YOO S R,PRAKASH S M,MIN D B.Off-odor study with gamma-irradiated orange juice using sensory and volatile compound analyses[J].Journal of Food Science,2003,68(4):1 259-1 264.
[33]BURBANK H M,QIAN M C.Volatile sulfur compounds in Cheddar cheese determined by headspace solid-phase microextraction and gas chromatograph-pulsed flame photometric detection[J].Journal of Chromatography A,2005,1066(1-2):149-157.
[34]PELUSIO F,NILSSON T,MONTANARELL L,et al.headspace solid-phase microextraction analysis of volatile organic sulfur-compounds in black-and-white truffle aroma[J].Journal of Agricultural and Food Chemistry,1995,43(8):2 138-2 143.
[35]LESTREMAU F,ANDERSSON F A T,DESAUZIERS V.Investigation of artefact formation during analysis of volatile sulphur compounds using solid phase microextraction(SPME)[J].Chromatographia,2004,59(9-10):607-613.
[36]JABALPURWALA F,GURBUZ O,ROUSEFF R.Analysis of grapefruit sulphur volatiles using SPME and pulsed flame photometric detection[J].Food Chemistry,2010,120(1):296-303.
[37]SPANIER A M,BOYLSTON T D.Effect of temperature on the analysis of beef flavor volatiles-focus on carbonyl and sulfur-containing-compounds[J].Food Chemistry,1994,50(3):251-259.
[38]SUMITANI H,SUEKANE S,SAKAI Y,et al.FPD-GCdetermination of S-methylmethioninesulfonium in satsuma mandarin juice[J].Agricultural and Biological Chemistry,2014,55(11):2 899-2 900.
[39]ALLEGRONE G,BELLIARDO F,CABELLA P.Comparison of volatile concentrations in hand-squeezed juices of four different lemon varieties[J].Journal of Agricultural and Food Chemistry,2006,54(5):1 844-1 848.
[40]MAHATTANATAWEE K,ROUSEFF R L.Comparison of aroma active and sulfur volatiles in three fragrant rice cultivars using GC-olfactometry and GC-PFPD[J].Food Chemistry,2014,154:1-6.
[41]LEHMANN D,DIETRICH A,HENER U,et al.stereoisomeric flavor compounds.LXX:1-p-menthene-8-thiolseparation and sensory evaluation of the enantiomers by enantioselective gas-chromatography olfactometry[J].Phytochemical Analysis,1995,6(5):255-257.
[42]WEBER B,MAAS B,MOSANDL A.stereoisomeric flavor compounds.72.stereoisomeric distribution of some chiral sulfur-containing trace components of yellow passion fruits[J].Journal of Agricultural and Food Chemistry,1995,43(9):2 438-2 441.
[43]ANNESS B J,BAMFORTH C W.Dimethyl sulfide-A review[J].Journal of the Institute of Brewing,1982,88(4):244-252.
[44]PEREZ-CACHO P R,MAHATTANATAWEE K,SMOOTK M,et al.Identification of sulfur volatiles in canned orange juices lacking orange flavor[J].Journal of Agricultural and Food Chemistry,2007,55(14):5 761-5 767.
[45]LI Jia-Xiao,SCHIEBERLE P,STEINHAUS M.Development of stable isotope dilution assays for the quantitation of the food odorants hydrogen sulphide,methanethiol,ethanethiol,and propane-1-thiol and application to durian(Durio zibethinus L.)pulp[J].European Food Research and Technology,2017,243(1):69-79.
[46]THOMAS B,ROTHE M.Aromasto e des brotes[J].Z.Lebensm.Unters.Forsch,1963,119:302-310.
[47]GOMEZ-MIGUEZ M J,CACHO J F,FERREIRA V,et al.Volatile components of Zalema white wines[J].Food Chemistry,2007,100(4):1 464-1 473.