云南新鲜松露和干制松露挥发性风味成分的对比分析
|
摘要
采用顶空固相微萃取(HS-SPME)法萃取云南新鲜采摘黑松露和真空冷冻干燥黑松露中的挥发性成分,利用气相色谱-质谱联用仪(GC-MS)和气相色谱-火焰光度检测器(GC-FPD)对挥发性成分和含硫物质进行鉴定。结果表明,新鲜黑松露和干制松露中分别鉴定出30种和83种挥发性风味物质,8种和19种含硫化合物。1-辛烯-3-醇、对甲酚甲醚、3-甲基丁醛、二烯丙基二硫醚和二甲基硫醚在新鲜松露中的含量较高;对甲酚甲醚、己酸、右旋柠檬烯、二甲基砜、烯丙基甲基三硫醚在干制松露中含量较高。气相色谱-嗅闻(GC-O)结合香气活力值(OAV)发现,新鲜松露中二烯丙基二硫醚、二甲基硫醚、1-辛烯-3-酮、3-甲基丁醛对香气贡献较大;干制松露中双(2-甲基-3-呋喃基)二硫醚、丙位壬内酯、己酸、1-辛烯-3-酮对伞花烃贡献较大。
Volatile compounds of fresh-picked truffles and vacuum freeze-drying truffles in Yunnan were extracted by headspace solid-phase microextraction(HS-SPME). Volatile components and sulfur aroma compounds were identified by gas chromatography-mass spectrometry(GC-MS) and gas chromatographyflame photometric detector(GC-FPD). The results showed that 30 and 83 volatile flavor compounds, 8 and 19 sulfur aroma compounds were detected in fresh-picked truffles and vacuum freeze-drying truffles, respectively. 1-Octen-3-ol, p-cresyl methyl ether, 3-methyl butyraldehyde, diallyl disulfide and dimethyl sulfide were higher in fresh truffles. p-Cresyl methyl ether, hexanoic acid, d-limonene, dimethyl sulfone, allyl methyl trisulfide were higher in dry truffles. The results of gas chromatography-olfactory(GC-O) combined with aroma activity value(OAV) indicated that diallyl disulfide, dimethyl sulfide, 1-octen-3-one and 3-methyl butyraldehyde had larger contribution to the aroma of fresh truffles. In dried truffles, bis(2-methyl-3-furyl)disulfide, γ-nonalactone, hexanoic acid, 1-octen-3-one had greater contribution to the aroma.
Volatile compounds of fresh-picked truffles and vacuum freeze-drying truffles in Yunnan were extracted by headspace solid-phase microextraction(HS-SPME). Volatile components and sulfur aroma compounds were identified by gas chromatography-mass spectrometry(GC-MS) and gas chromatographyflame photometric detector(GC-FPD). The results showed that 30 and 83 volatile flavor compounds, 8 and 19 sulfur aroma compounds were detected in fresh-picked truffles and vacuum freeze-drying truffles, respectively. 1-Octen-3-ol, p-cresyl methyl ether, 3-methyl butyraldehyde, diallyl disulfide and dimethyl sulfide were higher in fresh truffles. p-Cresyl methyl ether, hexanoic acid, d-limonene, dimethyl sulfone, allyl methyl trisulfide were higher in dry truffles. The results of gas chromatography-olfactory(GC-O) combined with aroma activity value(OAV) indicated that diallyl disulfide, dimethyl sulfide, 1-octen-3-one and 3-methyl butyraldehyde had larger contribution to the aroma of fresh truffles. In dried truffles, bis(2-methyl-3-furyl)disulfide, γ-nonalactone, hexanoic acid, 1-octen-3-one had greater contribution to the aroma.
引文
[1]SplivalloR,OttonelloS,MelloA,etal.Trufflevolatiles:From chemical ecology to aroma biosynthesis[J]. New Phytologist, 2011,189(3):688-699.
[2]Torregiani E, Lorier S, Sagratini G, et al. Comparative analysis of the volatile profile of 20 commercial samples of truffles, truffle sauces,andtruffle-flavoredoilsbyusingHS-SPME-GC-MS[J].Food Analytical Methods, 2017, 10(6):1-13.
[3]BellesiaF,PinettiA,BianchiA,etal.Volatilecompoundsofthe white truffle(tuber magnatum pico)from middle italy[J]. Flavour&Fragrance Journal, 2015, 11(4):239-243.
[4]CullereL,FerreiraV,ChevretB,etal.Characterisationofaroma active compounds in black truffles(tuber melanosporum)and summer truffles(tuberaestivum)bygaschromatographyolfactometry[J].Food Chemistry, 2010, 122(1):300-306.
[5]Mauriello G, Marino R, D'Auria M, et al. Determination of volatile organiccompoundsfromtrufflesviaSPME-GC-MS[J].Journalof Chromatographic Science, 2004, 42(6):299-305.
[6]PalomaD,ElenaI,GuillermoR,etal.Optimizationofsummer trufflearomaanalysisbyspme:Comparisonofextractionwith differentpolarityfibres.[J].FoodScienceandTechnology,2009,42(7):1253-1259.
[7]LauraC,VicenteF,MaríaEV,etal.Evaluationofgammaand electron-beam irradiation on the aromatic profile of black truffle(tuber melanosporum)and summer truffle(tuberaestivum)[J]. Innovative Food Science&Emerging Technologies, 2012, 13(1):151-157.
[8]Li Xiaolin(李小林), Chen Cheng(陈诚), Qing Yuan(清源), et al.Analysis of volatile aroma components in different species of truffle in huidong county by GC-MS[J]. Food Science(食品科学), 2015,36(18):132-136.
[9]Splivallo R, Ebeler S E. Sulfur volatiles of microbial origin are key contributors to human-sensed truffle aroma[J]. Applied Microbiology&Biotechnology, 2015, 99(6):2583-2592.
[10]Inglis T J, Hahne D R, Merritt A J, et al. Volatile-sulfur-compound profiledistinguishesBurkholderiapseudomalleifromBurkholderia thailandensis[J].JournalofClinicalMicrobiology,2015,53(3):1009-1011.
[11]Pacioni G, Cerretani L, Procida G, et al. Composition of commercial truffle flavored oils with GC-MS analysis and discrimination with an electronic nose[J]. Food Chemistry, 2014, 146(7):30-35.
[12]Liu T, Feng T, Chen W. Identification of volatile flavour components of Tuber melanosporum using simultaneous distillation-extraction[J].Czech Journal of Food Sciences, 2017, 35(6):483-487.
[13]NingZ,ChenH,SunB,etal.Comparativeanalysisofvolatile compositioninchinesetrufflesviaGC×GC/HR-TOF/MSand electronic nose[J]. International Journal of Molecular Sciences, 2016,17(4):412-416.
[14]Zhang Yueqi(张玥琪), Zhang Ning(张宁), Zhou Ying(周颖), et al.Analysisofvolatileflavorcompoundsinfreshyunnantruffle[J].Fine Chemicals(精细化工), 2015, 32(7):756-761.
[15]Fang Sanping(方三平), Pu Biao(蒲彪), Chen Anjun(陈安均), et al.Effects of maturity degree on the aroma compounds of tuber indicum[J]. Mycosystema(菌物学报), 2013, 32(6):1020-1027.
[16]Cao Fumin(曹福民), Zuo Xiangqun(左向群), Wu Zhongke(吴仲可). Principle and related problems of flame photometric detector[J].SpectroscopicInstrumentsandAnalysis(光谱仪器与分析),2002,50(2):46-48.
[17]Gaines K K, Chatham W H, Farwell S O. Comparison of the SCD andFPDforHRGCdeterminationofatmosphericsulfurgases[J].Journal of Separation Science, 2015, 13(7):489-493.
[18]ZhuR,ZhangHH,YangGP.Determinationofvolatilesulfur compoundsinseawaterandatmosphere[J].ChineseJournalof Analytical Chemistry, 2017, 45(10):1504-1510.
[19]ZhuJ,WangL,XiaoZ,etal.Characterizationofthekeyaroma compounds in mulberry fruits by application of gas chromatographyolfactometry(GC-O), odor activity value(OAV), gas chromatographymass spectrometry(GC-MS)and flame photometric detection(FPD)[J]. Food Chemistry, 2018, 245:775-782.
[20]Du X, Rouseff R. Aroma active volatiles in four southern highbush blueberry cultivars determined by gas chromatography olfactometry(GC-O)and gas chromatography-mass spectrometry(GC-MS)[J]. J Agric Food Chem, 2014, 62:4537-4543.
[21]Caliari V, Burin V M, Rosier J P, et al. Aromatic profile of brazilian sparklingwinesproducedwithclassicalandinnovativegrape varieties[J]. Food Research International, 2014, 62(8):965-973.
[22]CulleréL,FerreiraV,VenturiniME,etal.Potentialaromatic compounds as markers to differentiate between tuber melanosporum andtuberindicumtruffles[J].FoodChemistry,2013,141(1):105-110.
[23]BarrosL,BaptistaP,CorreiaDM,etal.Effectsofconservation treatment and cooking on the chemical composition and antioxidant activityofPortuguesewildediblemushrooms[J].Journalof Agricultural and Food Chemistry, 2007, 55(12):4781-4788.
[24]RuiHanming(芮汉明),HeFengxia(贺丰霞),GuoKai(郭凯).Analysisofvolatilecomponentsinlentinusedodesduringdrying process[J]. Food Science(食品科学), 2009, 30(8):255-259.
[25]An Jingjing(安晶晶), Wang Chengtao(王成涛), Liu Guorong(刘国荣), et al. Analysis of volatile aroma components of fresh and dry lentinus edodes with gas chromatography-mass spectrometry(GC-MS)[J].ScienceandTechnologyofFoodIndustry(食品工业科技),2012,33(14):68-71.
[26]SplivalloR,BossiS,MaffeiM,etal.Discriminationoftruffle fruitingbodyversusmycelialaromasbystirbarsorptive extraction[J]. Phytochemistry, 2007, 68:2584-2598.
[27]GiovanniP,LorenzoC,GiuseppeP,etal.Compositionof commercialtruffleflavoredoilswithGC-MSanalysisand discriminationwithanelectronicnose[J].FoodChemistry,2014,146(7):30-35.
[28]SunBaoguo(孙宝国).Flavoring[M].Beijing:ChemicalIndustry Press(化学工业出版社), 2010:66-78.
[29]Piloni M, Tat L, Tonizzo A, et al. Aroma characterisation of white trufflebyGC-MSandGC-O[J].ItalianJournalofFoodScience,2005, 17(4):463-468.
[2]Torregiani E, Lorier S, Sagratini G, et al. Comparative analysis of the volatile profile of 20 commercial samples of truffles, truffle sauces,andtruffle-flavoredoilsbyusingHS-SPME-GC-MS[J].Food Analytical Methods, 2017, 10(6):1-13.
[3]BellesiaF,PinettiA,BianchiA,etal.Volatilecompoundsofthe white truffle(tuber magnatum pico)from middle italy[J]. Flavour&Fragrance Journal, 2015, 11(4):239-243.
[4]CullereL,FerreiraV,ChevretB,etal.Characterisationofaroma active compounds in black truffles(tuber melanosporum)and summer truffles(tuberaestivum)bygaschromatographyolfactometry[J].Food Chemistry, 2010, 122(1):300-306.
[5]Mauriello G, Marino R, D'Auria M, et al. Determination of volatile organiccompoundsfromtrufflesviaSPME-GC-MS[J].Journalof Chromatographic Science, 2004, 42(6):299-305.
[6]PalomaD,ElenaI,GuillermoR,etal.Optimizationofsummer trufflearomaanalysisbyspme:Comparisonofextractionwith differentpolarityfibres.[J].FoodScienceandTechnology,2009,42(7):1253-1259.
[7]LauraC,VicenteF,MaríaEV,etal.Evaluationofgammaand electron-beam irradiation on the aromatic profile of black truffle(tuber melanosporum)and summer truffle(tuberaestivum)[J]. Innovative Food Science&Emerging Technologies, 2012, 13(1):151-157.
[8]Li Xiaolin(李小林), Chen Cheng(陈诚), Qing Yuan(清源), et al.Analysis of volatile aroma components in different species of truffle in huidong county by GC-MS[J]. Food Science(食品科学), 2015,36(18):132-136.
[9]Splivallo R, Ebeler S E. Sulfur volatiles of microbial origin are key contributors to human-sensed truffle aroma[J]. Applied Microbiology&Biotechnology, 2015, 99(6):2583-2592.
[10]Inglis T J, Hahne D R, Merritt A J, et al. Volatile-sulfur-compound profiledistinguishesBurkholderiapseudomalleifromBurkholderia thailandensis[J].JournalofClinicalMicrobiology,2015,53(3):1009-1011.
[11]Pacioni G, Cerretani L, Procida G, et al. Composition of commercial truffle flavored oils with GC-MS analysis and discrimination with an electronic nose[J]. Food Chemistry, 2014, 146(7):30-35.
[12]Liu T, Feng T, Chen W. Identification of volatile flavour components of Tuber melanosporum using simultaneous distillation-extraction[J].Czech Journal of Food Sciences, 2017, 35(6):483-487.
[13]NingZ,ChenH,SunB,etal.Comparativeanalysisofvolatile compositioninchinesetrufflesviaGC×GC/HR-TOF/MSand electronic nose[J]. International Journal of Molecular Sciences, 2016,17(4):412-416.
[14]Zhang Yueqi(张玥琪), Zhang Ning(张宁), Zhou Ying(周颖), et al.Analysisofvolatileflavorcompoundsinfreshyunnantruffle[J].Fine Chemicals(精细化工), 2015, 32(7):756-761.
[15]Fang Sanping(方三平), Pu Biao(蒲彪), Chen Anjun(陈安均), et al.Effects of maturity degree on the aroma compounds of tuber indicum[J]. Mycosystema(菌物学报), 2013, 32(6):1020-1027.
[16]Cao Fumin(曹福民), Zuo Xiangqun(左向群), Wu Zhongke(吴仲可). Principle and related problems of flame photometric detector[J].SpectroscopicInstrumentsandAnalysis(光谱仪器与分析),2002,50(2):46-48.
[17]Gaines K K, Chatham W H, Farwell S O. Comparison of the SCD andFPDforHRGCdeterminationofatmosphericsulfurgases[J].Journal of Separation Science, 2015, 13(7):489-493.
[18]ZhuR,ZhangHH,YangGP.Determinationofvolatilesulfur compoundsinseawaterandatmosphere[J].ChineseJournalof Analytical Chemistry, 2017, 45(10):1504-1510.
[19]ZhuJ,WangL,XiaoZ,etal.Characterizationofthekeyaroma compounds in mulberry fruits by application of gas chromatographyolfactometry(GC-O), odor activity value(OAV), gas chromatographymass spectrometry(GC-MS)and flame photometric detection(FPD)[J]. Food Chemistry, 2018, 245:775-782.
[20]Du X, Rouseff R. Aroma active volatiles in four southern highbush blueberry cultivars determined by gas chromatography olfactometry(GC-O)and gas chromatography-mass spectrometry(GC-MS)[J]. J Agric Food Chem, 2014, 62:4537-4543.
[21]Caliari V, Burin V M, Rosier J P, et al. Aromatic profile of brazilian sparklingwinesproducedwithclassicalandinnovativegrape varieties[J]. Food Research International, 2014, 62(8):965-973.
[22]CulleréL,FerreiraV,VenturiniME,etal.Potentialaromatic compounds as markers to differentiate between tuber melanosporum andtuberindicumtruffles[J].FoodChemistry,2013,141(1):105-110.
[23]BarrosL,BaptistaP,CorreiaDM,etal.Effectsofconservation treatment and cooking on the chemical composition and antioxidant activityofPortuguesewildediblemushrooms[J].Journalof Agricultural and Food Chemistry, 2007, 55(12):4781-4788.
[24]RuiHanming(芮汉明),HeFengxia(贺丰霞),GuoKai(郭凯).Analysisofvolatilecomponentsinlentinusedodesduringdrying process[J]. Food Science(食品科学), 2009, 30(8):255-259.
[25]An Jingjing(安晶晶), Wang Chengtao(王成涛), Liu Guorong(刘国荣), et al. Analysis of volatile aroma components of fresh and dry lentinus edodes with gas chromatography-mass spectrometry(GC-MS)[J].ScienceandTechnologyofFoodIndustry(食品工业科技),2012,33(14):68-71.
[26]SplivalloR,BossiS,MaffeiM,etal.Discriminationoftruffle fruitingbodyversusmycelialaromasbystirbarsorptive extraction[J]. Phytochemistry, 2007, 68:2584-2598.
[27]GiovanniP,LorenzoC,GiuseppeP,etal.Compositionof commercialtruffleflavoredoilswithGC-MSanalysisand discriminationwithanelectronicnose[J].FoodChemistry,2014,146(7):30-35.
[28]SunBaoguo(孙宝国).Flavoring[M].Beijing:ChemicalIndustry Press(化学工业出版社), 2010:66-78.
[29]Piloni M, Tat L, Tonizzo A, et al. Aroma characterisation of white trufflebyGC-MSandGC-O[J].ItalianJournalofFoodScience,2005, 17(4):463-468.