综述与专题评论

水果及其加工产品中糖苷键合态香气物质的研究进展

  • 马亚琴 ,
  • 张晨 ,
  • 邓涂静 ,
  • 周佳
展开
  • (西南大学柑桔研究所,国家柑桔工程技术研究中心,重庆,400712)
马亚琴(副研究员)和张晨(硕士研究生)为共同第一作者(马亚琴副研究员为通信作者,E-mail: maya211@163.com)

收稿日期: 2021-04-18

  修回日期: 2021-06-25

  网络出版日期: 2022-04-25

基金资助

现代农业产业技术体系建设专项资金资助

Research progress of glycoside bonded aroma compounds in fruits and their processed products

  • MA Yaqin ,
  • ZHANG Chen ,
  • DENG Tujing ,
  • ZHOU Jia
Expand
  • (Citrus Research Institute, Southwest University, National Citrus Engineering Research Center, Chongqing 400712, China)

Received date: 2021-04-18

  Revised date: 2021-06-25

  Online published: 2022-04-25

摘要

香气作为消费者衡量水果及其加工产品品质的关键指标,其优劣可以显著影响消费者对水果及其加工产品的接受程度。香气主要以游离态和键合态2种形式存在于果实中,其中糖苷键合态香气物质因其以糖苷形式存在而不易被人直接感知,糖苷键合态香气物质的研究对于提升、平衡、恢复水果及其加工产品的风味至关重要。该文综述了水果及其加工产品中糖苷键合态香气物质的结构、提取和分析方法、香气释放方式及一些常见香气化合物的保留指数与气味,以期为今后水果增香产业化应用提供理论参考。

本文引用格式

马亚琴 , 张晨 , 邓涂静 , 周佳 . 水果及其加工产品中糖苷键合态香气物质的研究进展[J]. 食品与发酵工业, 2022 , 48(6) : 290 -298 . DOI: 10.13995/j.cnki.11-1802/ts.027781

Abstract

Aroma, as a key index for consumers to measure the quality of fruits and their processed products, can significantly affect consumers' acceptance of fruits and their processed products. The aroma mainly exists in the form of free state and bonded state, and glycoside bonded aroma substances are not easy to be perceived directly. The study of glycoside bonded aroma substances is very important for improving, balancing and restoring the flavor of fruits and their processed products. This article reviewed the structure, extraction and analysis methods, aroma release methods, and the odor and retention index of some common aroma compounds in fruits and their processed products, in order to provide a theoretical reference for the industrial application of fruit aroma in the future.

参考文献

[1] AGRAWAL R, VERMA A K, SATLEWAL A.Application of nanoparticle-immobilized thermostable β-glucosidase for improving the sugarcane juice properties[J].Innovative Food Science & Emerging Technologies, 2016, 33:472-482.
[2] FRANCIS M J O, ALLCOCK C.Geraniol β-d-glucoside;occurrence and synthesis in rose flowers[J].Phytochemistry, 1969, 8(8):1 339-1 347.
[3] CORDONNIER R, BAYONOVE C L.Mise en evidence dans la raisin, variete Muscat d'Alexandrie, demonoterpenes lies revelables par une ou plusieur enzymes du fruit[J].Comptes rendus de l'Academie des Science, 1974, 278:3 387-3 390.
[4] GUNATA Y Z, BAYONOVE C L, BAUMES R L, et al.The aroma of grapes I.Extraction and determination of free and glycosidically bound fractions of some grape aroma components[J].Journal of Chromatography A, 1985, 331:83-90.
[5] CABRITA M J, FREITAS A M C, LAUREANO O, et al.Glycosidic aroma compounds of some Portuguese grape cultivars[J].Journal of the Science of Food and Agriculture, 2006, 86(6):922-931.
[6] UGLIANO M, MOIO L.Free and hydrolytically released volatile compounds of Vitis vinifera L.cv.Fiano grapes as odour-active constituents of Fiano wine[J].Analytica Chimica Acta, 2008, 621(1):79-85.
[7] MARTENS M, DALEN G A, RUSSWURM H.Proceedings of Weurman Flavour Research Symposium[M].5th ed.Wiley:Flavour science and technology, 1987.
[8] 宛晓春, 汤坚,袁身淑,等.柠檬汁中游离态和键合态萜类化合物的研究[J].食品与发酵工业, 1991,17(4):31-37.
WAN X C, TANG J,YUAN S S,et al.Study on free and glucosidically bound of fresh terpenoids in lemon juice[J].Food and Fermentation Industries, 1991,17(4):31-37.
[9] 范刚. 柑橘及其加工制产品中游离态和键合态挥发性物质的研究[D].武汉:华中农业大学, 2010.
FAN G.Study on free and bound volatile compounds in oranges and its processing products[D].Wuhan:Huazhong Agricultural University, 2010.
[10] REN J N, TAI Y N, DONG M, et al.Characterisation of free and bound volatile compounds from six different varieties of Citrus fruits[J].Food Chemistry, 2015, 185(10):25-32.
[11] BICALHO B, PEREIRA A S, AQUINO NETO F R, et al.Application of high-temperature gas chromatography-mass spectrometry to the investigation of glycosidically bound components related to cashew apple (Anacardium occidentale L.Var.Nanum) volatiles[J].Journal of Agricultural and Food Chemistry, 2000, 48(4):1 167-1 174.
[12] VRHOVSEK U, LOTTI C, MASUERO D, et al.Quantitative metabolic profiling of grape, apple and raspberry volatile compounds (VOCs) using a GC/MS/MS method[J].Journal of Chromatography B,2014, 966(9):132-139.
[13] MOSES T, POLLIER J, THEVELEIN J M, et al.Bioengineering of plant (tri)terpenoids:From metabolic engineering of plants to synthetic biology in vivo and in vitro[J].The New Phytologist, 2013, 200(1):27-43.
[14] ZHOU Q , LI G J, OU-YANG Z, et al.Volatile organic compounds profiles to determine authenticity of sweet orange juice using head space gas chromatography coupled with multivariate analysis[J].Foods, 2020, 9(4):505.
[15] YUE X F, REN R H, MA X, et al.Dynamic changes in monoterpene accumulation and biosynthesis during grape ripening in three Vitis vinifera L.cultivars[J].Food Research International, 2020, 137(4):109736.
[16] PARK S K, MORRISON J C, ADAMS D O, et al.Distribution of free and glycosidically bound monoterpenes in the skin and mesocarp of Muscat of Alexandria grapes during development[J].Journal of Agricultural and Food Chemistry, 1991, 39(3):514-518.
[17] WEN Y Q, HE F, ZHU B Q, et al.Free and glycosidically bound aroma compounds in cherry (Prunus avium L.)[J].Food Chemistry, 2014, 152:29-36.
[18] 刘华南, 江虹锐, 陆雄伟, 等.顶空固相微萃取-气质联用分析不同芒果品种香气成分差异[J].食品工业科技, 2021, 42(1):211-218.
LIU H N, JIANG H R, LU X W, et al. Analysis and comparison of aroma components in different mango varieties by headspace solid phase microextraction-gas chromatograph-mass spectrometer[J]. Science and Technology of Food Industry, 2021, 42(11): 211-217.
[19] MAO D S, LIU H, LI Z, et al, et al.Impact of sensory interactions among volatile compounds of juice of Red Delicious apples[J].Horticulture, Environment and Biotechnology, 2020, 61(1):197-206.
[20] WU C D, LIU J M, YAN L C, et al.Assessment of odor activity value coefficient and odor contribution based on binary interaction effects in waste disposal plant[J].Atmospheric Environment, 2015, 103(2):231-237.
[21] SCHIEVANO E, D'AMBROSIO M, MAZZARETTO I, et al.Identification of wine aroma precursors in Moscato Giallo grape juice:A nuclear magnetic resonance and liquid chromatography-mass spectrometry tandem study[J].Talanta (Oxford), 2013, 116(10):841-851.
[22] 任婧楠, 董曼, 杨子玉, 等.树莓汁中键合态香气物质提取方法及糖基组成的研究[J].现代食品科技, 2015, 31(8):316-322.
REN J N, DONG M, YANG Z Y, et al.Extraction of bound aroma compounds in raspberry juice and analysis of the sugar moieties[J].Modern Food Science and Technology, 2015, 31(8):316-322.
[23] 奕志英, 冯涛, 李晓贝, 等.石榴汁糖苷键合态香气前体物质的初步研究[J].现代食品科技, 2017, 33(1):221-227.
YI Z Y, FENG T, LI X B, et al.Preliminary study on the glycosidically bound aroma compounds from pomegranate juice[J].Modern Food Science and Technology, 2017, 33(1):221-227.
[24] 彭邦远, 丁小娟, 赵泽伟, 等.水解释放刺梨汁键合态香气化合物及糖基组成解析[J].食品与机械, 2019, 35(7):13-19.
PENG B Y, DING X J, ZHAO Z W, et al.The analysis of the hydrolysis releases of bound aroma compounds and glycosyl composition in Rose roxbuighii juice [J].Food & Machinery, 2019, 35(7):13-19.
[25] CAI K,XIANG Z M,PAN W J,et al.Identification and quantitation of glycosidically bound aroma compounds in three tobacco types by gas chromatography-mass spectrometry[J].Journal of Chromatog raphy Chromatogr A, 2013, 1311:149-156.
[26] JESU'S IBARZ M, FERREIRA V, HERNÁNDEZ-ORTE P, et al.Optimization and evaluation of a procedure for the gas chromatographic-mass spectrometric analysis of the aromas generated by fast acid hydrolysis of flavor precursors extracted from grapes [J].Journal of Chromatography A, 2006, 1116(1-2):217-229.
[27] 王颖, 张文君, 李慧冬, 等.金川雪梨和秦酥挥发性芳香物质的SPME-GC-MS分析[J].食品研究与开发, 2020, 41(1):160-166.
WANG Y, ZHANG W J, LI H D, et al.Analysis of SPME-GC-MS on volatile aromatic compounds of jinchuanxue pear and qinsu[J].Food Research and Development, 2020, 41(1):160-166.
[28] MADRERA R R, VALLES B S.Determination of volatile compounds in apple pomace by stir bar sorptive extraction and gas chromatography-mass spectrometry (SBSE-GC-MS).[J].Journal of Food Science, 2011, 76(9):C1 326-C1 334.
[29] LIU Y, HE C C, SONG H L.Comparison of SPME versus safe processes for the analysis of flavor compounds in watermelon juice[J].Food Analytical Methods, 2018, 11(6):1 677-1 689.
[30] LEE B, LIN P C, CHA H S, et al.Characterization of volatile compounds in Cowart muscadine grape(Vitis rotundifolia) during ripening stages using GC-MS combined with principal component analysis[J].Food Science and Biotechnology, 2016, 25(5):1 319-1 326.
[31] YU A N, YANG Y N, YANG Y, et al.Free and bound volatile compounds in the Rubus coreanus fruits of different ripening stages[J].Journal of Food Biochemistry, 2019, 43(10):e12964.
[32] DU D D, XU M, WANG J, et al.Tracing internal quality and aroma of a red-fleshed kiwifruit during ripening by means of GC-MS and E-nose[J].RSC Advances, 2019, 9(37):21 164-21 174.
[33] 王可兴, 章肇敏, 任婧楠, 等.巴氏灭菌对橙汁中键合态香气物质的影响研究[J].食品工业科技, 2014, 35(13):49-52;56.
WANG K X, ZHANG Z M, REN J N, et al.Study on the effect of pasteurization on the bound aroma compounds in orange juice[J].Science and Technology of Food Industry, 2014, 35(13):49-52;56.
[34] ANANTHAKUMAR A, VARIYAR P S, SHARMA A.Estimation of aroma glycosides of nutmeg and their changes during radiation processing[J].Journal of Chromatography A, 2006, 1108(2):252-257.
[35] 周志, 范刚, 王可兴, 等.微波辅助酸解释放刺梨汁键合态香气物质的效果[J].食品科学, 2012, 33(8):99-103.
ZHOU Z, FAN G, WANG K X, et al.Releasing effect of microwave-assisted acid hydrolysis on bound volatile aroma compounds in Rosa roxburghii tratt(Cili pear) Juice[J].Food Science, 2012, 33(8):99-103.
[36] SUN Y J, PENG W, ZENG L, et al.Using power ultrasound to release glycosidically bound volatiles from orange juice:A new method[J].Food Chemistry, 2021, 344(5):128580.
[37] WINTERHALTER P, SEFTON M A, WILLIAMS P J.Volatile C13-norisoprenoid compounds in riesling wine are generated from multiple precursors[J].American Journal of Enology & Viticulture, 1990, 41(4):277-283.
[38] 任婧楠, 荣茂, 彭勋, 等.树莓汁中键合态香气物质的酸解[J].食品科学, 2013, 34(13):101-104.
REN J N, RONG M, PENG X, et al.Acidic hydrolysis of bound aroma compounds in raspberry juice[J].Food Science, 2013, 34(13):101-104.
[39] 陈亦欣, 陈虹吉, 叶兴乾, 等.酶解和酸解处理对杨梅汁键合态香气释放的影响[J].中国食品学报, 2021, 21(2):299-307.
CHEN Y X, CHEN H J, YE X Q, et al.Effect of enzymolysis and acidolysis on aroma release of myrica rubra juice[J].Journal of Chinese Institute of Food Science and Technology, 2021, 21(2):299-307.
[40] HAMPEL D, ROBINSON A L, JOHNSON A J, et al.Direct hydrolysis and analysis of glycosidically bound aroma compounds in grapes and wines:Comparison of hydrolysis conditions and sample preparation methods[J].Australian Journal of Grape and Wine Research, 2014, 20(3):361-377.
[41] ZHU F M, DU B, LI J.Aroma enhancement and enzymolysis regulation of grape wine using β‐glycosidase[J].Food Science & Nutrition, 2014, 2(2):139-145.
[42] BODAKOWSKA-BOCZNIEWICZ J, GARNCAREK Z.Immobilization of naringinase from Penicillium decumbens on chitosan microspheres for debittering grapefruit juice[J].Molecules (Basel, Switzerland), 2019, 24(23):4234.
[43] ÜNAL M Ü, ŞENER A.Biochemical properties of β-glucosidase from Turkish Hachalilogˇlu apricot (Prunus armenica L.) as affected by harvest year[J].Food Science & Technology, 2017, 79(6):190-196.
[44] GUO Y, YAN Q J, YANG Y, et al.Expression and characterization of a novel β-glucosidase, with transglycosylation and exo-β-1,3-glucanase activities, from Rhizomucor miehei[J].Food Chemistry, 2015, 175:431-438.
[45] 郭金玲, 陈程鹏, 周一郎, 等.黑曲霉β-葡萄糖苷酶的分离纯化及酶学性质研究[J].中国酿造, 2021, 40(2):83-87.
GUO J L, CHEN C P, ZHOU Y L, et al.Isolation, purification and enzymatic properties of β-glucosidase from Aspergillus niger[J].China Brewing, 2021, 40(2):83-87.
[46] KUO H P, WANG R, HUANG C Y, Journal of Food and Drug Aralysis.Characterization of an extracellular β-glucosidase from Dekkera bruxellensis for resveratrol production[J].Journal of Food and Drug Aralysis, 2018, 26(1):163-171.
[47] MAHAPATRA S, VICKRAM A S, SRIDHARAN T B, et al.Screening, production, optimization and characterization of β-glucosidase using microbes from shellfish waste[J].3 Biotech, 2016, 6(2):213.
[48] MALLEK-FAKHFAKH H, BELGHITH H.Physicochemical properties of thermotolerant extracellular β-glucosidase from Talaromyces thermophilus and enzymatic synthesis of cello-oligosaccharides[J].Carbohydrate Research, 2016, 419:41-50.
[49] BARBAGALLO R N, PALMERI R, FABIANO S, et al.Characteristic of β-glucosidase from Sicilian blood oranges in relation to anthocyanin degradation[J].Enzyme and Microbial Technology,2007, 41(5):570-575.
[50] KARA H E, SINAN S, TURAN Y.Purification of beta-glucosidase from olive (Olea europaea L.) fruit tissue with specifically designed hydrophobic interaction chromatography and characterization of the purified enzyme[J].Journal of Chromatography B, 2011, 879(19):1 507-1 512.
[51] BHALLA T C, ASIF M, SMITA K.Purification and characterization of cyanogenic β-glucosidase from wild apricot (Prunus armeniaca L.)[J].Process biochemistry (1991), 2017, 58:320-325.
[52] SELLAMI I, MALL V, SCHIEBERLE P, et al.Changes in the key odorants and aroma profiles of hamlin and valencia orange juices not from concentrate(NFC)during chilled storage[J].Journal of Agricultural and Food Chemistry, 2018, 66(28):7 428-7 440.
[53] PEREZ-CACHO P R, ROUSEFF R L.Fresh squeezed orange juice odor:A review[J].Critical Reviews in Food Science and Nutrition, 2008, 48(7):681-695.
[54] 张凌培, 覃其静, 唐耀辉.气相色谱仪在食品安全检测中的研究进展[J].中国食品, 2021(8):124-125.
ZHANG L P, QIN Q J, TANG Y H.Research progress of gas chromatograph in food safety detection[J].China Food, 2021(8):124-125.
[55] SHUI M Z, FENG T, TONG Y Z, et al.Characterization of key aroma compounds and construction of flavor base module of chinese sweet oranges[J].Molecules (Basel, Switzerland), 2019, 24(13):2384.
[56] VENDEL I, HERTOG M, NICOLAÏ B.Fast analysis of strawberry aroma using SIFT-MS:A new technique in postharvest research[J].Postharvest Biology and Technology, 2019, 152(6):127-138.
[57] NIU Y W, WANG P P, XIAO Z D, et al.Evaluation of the perceptual interaction among ester aroma compounds in cherry wines by GC-MS, GC-O, odor threshold and sensory analysis:An insight at the molecular level[J].Food Chemistry, 2019, 275(3):143-153.
[58] YANG Y, JIN G J, WANG X J, et al.Chemical profiles and aroma contribution of terpene compounds in Meili (Vitis vinifera L.) grape and wine[J].Food Chemistry, 2019,284(6):155-161.
文章导航

/