传统发酵食品中吡嗪类物质的研究进展Research Progress on Pyrazines in Traditional Fermented Foods
李明宇,陈旭露,肖婷,柳志杰,徐宁
摘要(Abstract):
中国传统发酵食品以其独特的风味和丰富的营养成分深受人们喜爱,并在中华饮食文化中占有重要地位。吡嗪类物质作为特征香气化合物,提供青草香、烘烤香、甜香等,其酿造工艺参数不同和发酵过程中微生物相互作用都会影响吡嗪类物质的生成。文章重点综述了在传统发酵食品中吡嗪类物质对风味的贡献、烷基吡嗪的合成途径以及相关功能菌株对生成吡嗪类物质的影响,为进一步探索微生物多样性与风味形成之间的关系、提升传统发酵食品的风味功能品质提供了研究思路。
关键词(KeyWords): 传统发酵食品;吡嗪;风味物质;合成机制
基金项目(Foundation): 湖北省重点研发计划项目(2023BBB010)
作者(Author): 李明宇,陈旭露,肖婷,柳志杰,徐宁
参考文献(References):
- [1]陈坚,汪超,朱琪,等.中国传统发酵食品研究现状及前沿应用技术展望[J].食品科学技术学报,2021,39(2):1-7.
- [2]韩斌.中国传统发酵食品的现状及进展分析[J].科技资讯,2012(14):220.
- [3]CHOUDHARY D,GARG S,KAUR M,et al.Advances in the synthesis and bio-applications of pyrazine derivatives:a review[J].Polycyclic Aromatic Compounds,2023,43(5):4512-4578.
- [4]吕晓凤,孟武,刘玉涛,等.直接进样-气相色谱质谱法快速测定芝麻香白酒及酒醅中吡嗪类风味组分的研究[J].酿酒科技,2023(12):17-22.
- [5]刘家欢,孙细珍,熊亚青,等.不同轮次酱香型白酒中吡嗪类化合物含量分析[J].食品与发酵科技,2023,59(3):103-110.
- [6]吴奇霄,赵兴蓉,余松柏,等.白酒中吡嗪类化合物分析及与酯的感知交互作用[J].现代食品科技,2024,4(11):345-357.
- [7]孙棣,赵贵斌,杨波.酱香型白酒中吡嗪类化合物的检测及特点[J].中国酿造,2015,34(12):162-166.
- [8]WU J H,ZHAO H B,DU M,et al.Dispersive liquid-liquid microextraction for rapid and inexpensive determination of tetramethylpyrazine in vinegar[J].Food Chemistry,2019,286:141-145.
- [9]YANG H,WANG J,CAO W.Improved liquid-liquid extraction followed by HPLC-UV for accurate and eco-friendly determination of tetramethylpyrazine in vinegar products[J].Journal of Chromatography B:Analytical Technologies in the Biomedical and Life Sciences,2023,1229(5):123869.
- [10]孙啸涛,王宗元,刘淼,等.涡旋辅助液液微萃取结合GC-MS法检测67种白酒中四甲基吡嗪、4-甲基愈创木酚和4-乙基愈创木酚[J].食品科学,2017,38(18):73-79.
- [11]国家卫生和计划生育委员会.食品安全国家标准食品添加剂 2,5-二甲基吡嗪:GB 29970—2013[S].北京:中国标准出版社,2013.
- [12]国家卫生和计划生育委员会.食品安全国家标准食品添加剂 2,3,5-三甲基吡嗪:GB 1886.292—2016[S].北京:中国标准出版社,2016.
- [13]国家卫生和计划生育委员会.食品安全国家标准食品添加剂 2,3,5,6-四甲基吡嗪:GB 1886.295—2016[S].北京:中国标准出版社,2016.
- [14]杨沙,罗玉航,张季,等.高效液相色谱法同时测定不同年份酱香型白酒中12种吡嗪化合物含量[J].食品安全质量检测学报,2024,15(12):220-229.
- [15]孙棣,冯永渝,赵贵斌,等.液相色谱-质谱联用法快速测定酱香型白酒中的吡嗪类化合物[J].食品科技,2015,40(7):343-346.
- [16]龙四红,廖妍俨,孙棣,等.高效液相色谱法快速测定白酒中8种吡嗪类化合物[J].中国酿造,2021,40(1):176-182.
- [17]JEON S H,SHIN J H,KIM Y P,et al.Determination of volatile alkylpyrazines in microbial samples using gas chromatography-mass spectrometry coupled with head space-solid phase microextraction[J].Journal of Analytical Science and Technology,2016,7(1):16.
- [18]孙细珍,熊亚青,倪兴婷,等.吡嗪类化合物对酱香型白酒香气特征的影响分析[J].食品与发酵工业,2025(1):305-311.
- [19]FAN W L,XU Y,ZHANG Y H.Characterization of pyrazines in some Chinese liquors and their approximate concentrations[J].Journal of Agricultural and Food Chemistry,2007,55(24):9956-9962.
- [20]徐岩,吴群,范文来,等.中国白酒中四甲基吡嗪的微生物产生途径的发现与证实[J].酿酒科技,2011(7):37-40.
- [21]胡智慧,陈方,郭雪峰,等.白酒中健康因子2,3,5,6-四甲基吡嗪形成机理的研究进展[J].中国酿造,2024,43(1):27-33.
- [22]冯云子.高盐稀态酱油关键香气物质的变化规律及形成机理的研究[D].广州:华南理工大学,2015.
- [23]LIU Z P,XIAO T,WANG J,et al.Analysis of the contribution of koji-making with Z.rouxii on volatile compounds of soy sauce[J].LWT-Food Science and Technology,2023,183(5):114903.
- [24]LEE S M,KIM S,KIM Y.Determination of key volatile compounds related to long-term fermentation of soy sauce[J].Journal of Food Science,2019,84(10):2758-2776.
- [25]SCALONE G L L,LAMICHHANE P,CUCU T,et al.Impact of different enzymatic hydrolysates of whey protein on the formation of pyrazines in Maillard model systems[J].Food Chemistry,2019,278:533-544.
- [26]武倩宇,耿予欢.提高麸皮占比对高盐稀态酱油品质及香气成分的改善作用[J].现代食品科技,2024,40(1):262-271.
- [27]戴璐瑶,许睿琦,苏志林,等.11种国产高盐稀态酱油的氨基酸组分和挥发性物质的特征性分析[J].中国酿造,2023,42(11):73-81.
- [28]史伊格,蒲丹丹,勇倩倩,等.10种特级酱油香气差异分析[J].食品工业科技,2024,45(4):250-260.
- [29]熊思瑞,王云峰,张智勇,等.木桶发酵酱油挥发性风味物质研究及体外降压活性分析[J].食品工业,2024,45(1):245-253.
- [30]邓岳,杨阳,梁丽静,等.传统工艺酿造酱油微生物多样性与风味研究[J].中国调味品,2021,46(3):104-108.
- [31]丁莉莉,王昊,潘志辉,等.液液萃取-气相色谱-质谱法快速分析酱油中的呈香组分[J].天津科技大学学报,2020,35(2):22-29.
- [32]白佳伟,陈亮,周尚庭,等.特级高盐稀态酿造酱油中关键香气物质的分析[J].中国酿造,2019,38(11):179-185.
- [33]范霞,陈荣顺.5种市售酿造酱油风味物质及氨基酸含量分析[J].中国调味品,2019,44(10):144-148.
- [34]田晶晶.发酵食醋中多种烷基吡嗪类化合物和风味成分的变化规律研究[D].福州:福建农林大学,2018.
- [35]纪凤娣,鲁绯,陶汇源,等.基于液相色谱的镇江香醋及其相关产品中四甲基吡嗪的分析方法[J].食品科学,2019,40(22):293-298.
- [36]韩凯,杜将,纪薇.山西老陈醋熏醅过程中吡嗪类生成规律分析[J].中国酿造,2023,42(8):84-89.
- [37]王洪江,赵品贞,姬庆,等.影响蚝油气味品质的关键风味化合物的研究[J].食品与发酵工业,2025(7):309-315.
- [38]李英.虾酱的风味成分分析与感官品质评价[D].福州:福建农林大学,2016.
- [39]文鹤,查双龙,胡祥飞,等.曲霉型豆豉快速发酵工艺生产过程中的挥发性成分对比分析[J].食品与发酵工业,2021,47(16):239-246.
- [40]SHAKOOR A,ZHANG C P,XIE J C,et al.Maillard reaction chemistry in formation of critical intermediates and flavour compounds and their antioxidant properties[J].Food Chemistry,2022,393(8):133416.
- [41]WANG F R,SHEN H L,LIU T,et al.Formation of pyrazines in Maillard model systems:effects of structures of lysine-containing dipeptides/tripeptides[J].Foods,2021,10(2):273.
- [42]MA Y J,WANG X Y,ZHU B W,et al.Model studies on the formation of 2-vinylpyrazine and 2-vinyl-6-methylpyrazine in Maillard-type reactions[J].Food Chemistry,2022,374(8):131652.
- [43]YU H,ZHANG R Y,YANG F W,et al.Control strategies of pyrazines generation from Maillard reaction[J].Trends in Food Science & Technology,2021,112:795-807.
- [44]LIU J B,LIU M Y,HE C C,et al.Effect of thermal treatment on the flavor generation from Maillard reaction of xylose and chicken peptide[J].LWT-Food Science and Technology,2015,64(1):316-325.
- [45]CAI L Y,LI D M,DONG Z J,et al.Change regularity of the characteristics of Maillard reaction products derived from xylose and Chinese shrimp waste hydrolysates[J].LWT-Food Science and Technology,2016,65(5):908-916.
- [46]YU A N,TAN Z W,WANG F S.Mechanistic studies on the formation of pyrazines by Maillard reaction between L-ascorbic acid and L-glutamic acid[J].LWT-Food Science and Technology,2013,50(1):64-71.
- [47]GUAN Y G,ZHANG B S,YU S J,et al.Effects of ultrasound on a glycin-glucose model system—a means of promoting maillard reaction[J].Food and Bioprocess Technology,2011,4(8):1391-1398.
- [48]ONG O X H,SEOW Y X,ONG P,et al.High-intensity ultrasound production of Maillard reaction flavor compounds in a cysteine-xylose model system[J].Ultrasonics Sonochemistry,2015,26(2):399-407.
- [49]KIM Y R,AHN H W,LEE K G.Analysis of glyoxal,methylglyoxal and diacetyl in soy sauce[J].Food Science and Biotechnology,2021,30(11):1403-1408.
- [50]KIM S J,KWON J G,KIM Y R,et al.Correlation analysis between the concentration of α-dicarbonyls and flavor compounds in soy sauce[J].Food Bioscience,2020,36:100615.
- [51]CUI R Y,ZHENG J,WU C D,et al.Effect of different halophilic microbial fermentation patterns on the volatile compound profiles and sensory properties of soy sauce moromi[J].European Food Research and Technology,2014,239(2):321-331.
- [52]ZHU Q,CHEN L Q,PU X X,et al.The differences in the composition of Maillard components between three kinds of sauce-flavor Daqu[J].Fermentation,2023,9(4):860.
- [53]ZHANG Y D,SHEN Y,CHENG W,et al.Understanding the shifts of microbial community and metabolite profile from wheat to mature Daqu[J].Frontiers in Microbiology,2021,12:714726.
- [54]RUAN W,LIU J L,LI P L,et al.Flavor production driven by microbial community dynamics and their interactions during two-stage fermentation of Ziziphus jujuba vinegar[J].Food Bioscience,2024,57(4):103537.
- [55]LIU W H,CHAI L J,WANG H M,et al.Community-level bioaugmentation results in enzymatic activity- and aroma-enhanced Daqu through altering microbial community structure and metabolic function[J].Food Bioscience,2024,57:103630.
- [56]ZHANG L Q,HUANG J,ZHOU R Q,et al.Evaluating the feasibility of fermentation starter inoculated with Bacillus amyloliquefaciens for improving acetoin and tetramethylpyrazine in Baoning bran vinegar[J].International Journal of Food Microbiology,2017,255:42-50.
- [57]DONG W W,YU X,WANG L Y,et al.Unveiling the microbiota of sauce-flavor Daqu and its relationships with flavors and color during maturation[J].Frontiers in Microbiology,2024,15:1345772.
- [58]黄武,唐绍培,班世栋,等.高温放线菌FBKL4.010对酱香大曲酶活、理化特性和挥发性成分贡献的研究[J].食品与发酵科技,2022,58(2):15-21.
- [59]AFOAKWA E O,PATERSON A,FOWLER M,et al.Flavor formation and character in cocoa and chocolate:a critical review[J].Critical Reviews in Food Science and Nutrition,2008,48(9):840-857.
- [60]吴建峰.白酒中四甲基吡嗪全程代谢机理研究[D].无锡:江南大学,2013.
- [61]FADEL H,LOTFY S N,ASKER M,et al.Nutty-like flavor production by Corynbacterium glutamicum 1220T from enzymatic soybean hydrolysate.Effect of encapsulation and storage on the nutty flavoring quality[J].Journal of Advanced Research,2018,10:31-38.
- [62]陈莹琪,陈杰,周耀进,等.浓香型大曲微生物菌群演替与吡嗪类物质合成的关系[J].食品科学,2023,44(2):222-230.
- [63]张丽杰,张怀志,徐岩.枯草芽孢杆菌Nr.5和底物添加促进酱油中吡嗪类物质合成[J].食品与发酵工业,2020,46(21):1-8.
- [64]张伟,杨俊文,余冰艳,等.耐盐植物乳杆菌的选育及其对高盐稀态发酵酱油品质的影响[J].食品与发酵工业,2023,49(1):86-94.
- [65]张玲.嗜盐四联球菌、鲁氏接合酵母及易变假丝酵母的添加对日式酱油品质的影响[D].无锡:江南大学,2019.
- [66]刘佳乐,周朝晖,李铁桥,等.酱油发酵过程强化嗜盐四联球菌对酱油品质的影响[J].食品与发酵工业,2020,46(17):96-106.
- [67]冯云子,王靖雯,赵谋名.一种提升酱油中吡嗪类化合物含量的耐盐酵母菌及其应用:中国,202210108961.9[P].2022-05-13.
- [68]李雨佳,罗丽蓉,尚常花.微生物发酵生产四甲基吡嗪方法综述[J].广西师范大学学报(自然科学版),2024,42(4):32-40.
- [69]万雨薇,林琛,闫子恒,等.酱醪贝莱斯芽胞杆菌四甲基吡嗪高产菌的选育及其发酵优化[J].中国食品学报,2023,23(8):175-185.
- [70]张怀志.重要风味化合物2-乙基-3,5/3,6-二甲基吡嗪的微生物合成途径解析[D].无锡:江南大学,2020.
- [71]YU A,TAN Z,SHI B.Influence of the pH on the formation of pyrazine compounds by the Maillard reaction of L-ascorbic acid with acidic,basic and neutral amino acids[J].Asia-Pacific Journal of Chemical Engineering,2012,7(3):455-462.
- [72]韩凯,杜将,纪薇.山西老陈醋熏醅过程中吡嗪类生成规律分析[J].中国酿造,2023,42(8):84-89.
- [73]张薷月.超声波对酱油的催陈作用及其吡嗪类化合物加速合成机理研究[D].无锡:江南大学,2022.
- [74]冯云子,周婷,吴伟宇,等.酱油风味与功能性成分研究进展[J].食品科学技术学报,2021,39(4):14-28.
- [75]KUMAR S,DINESHA P,UDAYAKUMAR D,et al.Design,synthesis,characterization,and biological evaluation of novel pyrazine-1,3,4-oxadiazole/[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine hybrids as potent antimycobacterial agents[J].Journal of Molecular Structure,2024,1304:137657.
- [76]陈婷婷,王帆,姬艳华.川芎嗪联合血栓通治疗缺血性脑卒中的效果分析[J].中国实用医药,2024,19(3):82-84.
- [77]樊玲玲,李毅,罗碧兰,等.吡嗪类化合物的合成及其抗血小板凝集活性测试[J].化学通报,2019,82(2):128-132.
- [78]刘占中,王春颖,王亮,等.吡嗪酰胺不同给药频次的效果及药效学评价[J].河北医药,2020,42(19):2981-2983.
- [79]付德才,周鸿娟,狄蕊,等.3,4-二氢吡咯[1,2-a]吡嗪-1-酮衍生物的合成及抗炎镇痛作用[J].中国医药化学杂志,2006(1):23-26.
- [80]MORTZFELD F B,HASHEM C,VRANKOVá K,et al.Pyrazines:synthesis and industrial application of these valuable flavor and fragrance compounds[J].Biotechnology Journal,2020,15(11):2000064.
- [81]OBOT I B,ONYEACHU I B,UMOREN S A.Pyrazines as potential corrosion inhibitors for industrial metals and alloys:a review[J].Journal of Bio- and Tribo-Corrosion,2018,4(2):323740781.
- [82]WURDEMANN M A,NITU C,DE WILDEMAN S,et al.The forgotten pyrazines:exploring the dakin-west reaction[J].Chemistry,2020,26(36):8090-8100.