Research Progress of the Detection, Source, Aroma and Functional Activity of Pyrazine Compounds in High Temperature Daqu Baijiu

ZHU Yanmei; CHEN Hengye; DENG Gaoqiong; FU Haiyan

doi:10.13386/j.issn1002-0306.2022040256

Volume 44 Issue 5

Feb. 2023

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Science and Technology of Food Industry > 2023 > 44(5): 420-428. > DOI: 10.13386/j.issn1002-0306.2022040256

ZHU Yanmei, CHEN Hengye, DENG Gaoqiong, et al. Research Progress of the Detection, Source, Aroma and Functional Activity of Pyrazine Compounds in High Temperature Daqu Baijiu[J]. Science and Technology of Food Industry, 2023, 44(5): 420−428. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2022040256.

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Research Progress of the Detection, Source, Aroma and Functional Activity of Pyrazine Compounds in High Temperature Daqu Baijiu

School of Pharmacy, South-Central Minzu University, Wuhan 430074, China

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Received Date: April 21, 2022
Available Online: December 25, 2022

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Abstract

Abstract

Microcompounds, the key factors for the difference of flavor and quality in Baijiu, are one of the hot topics in the research field of Baijiu. Pyrazine compounds are a kind of microcompounds which contribute to the formation of the flavor in Baijiu, and are also important functional components in Bajiu. In this review, the types and contents of pyrazine compounds known in high temperature Daqu Baijiu and their common detection methods are reviewed in detail. And the source (microbial synthesis and Maillard reaction), aroma and functional activities of pyrazines are also discussed. Pyrazines, which have both flavor and functional activities in high temperature Daqu Baijiu and are closely related to the microbial fermentation and brewing process of Baijiu, will be widely used in the production, quality control and adulteration identification for Baijiu. This review can provide theoretical reference for the study of pyrazines in Baijiu.
- Baijiu,
- pyrazine,
- high temperature Daqu,
- detection,
- functional component

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References

[1]	YI Z L, JIN Y L, XIAO Y, et al. Unraveling the contribution of high temperature stage to Jiang-flavor Daqu, a Baijiu starter for production of Chinese Jiang-flavor Baijiu, with special reference to metatranscriptomics[J]. Food Microbiology, 2019, 10: 472.
[2]	WANG M Y, YANG J G, ZHAO Q S, et al. Research progress on flavor compounds and microorganisms of sauce flavor Baijiu[J]. Food Science,2019,84(1):6−18.
[3]	吴建峰. 中国白酒中健康功能性成份四甲基吡嗪的研究综述[J]. 酿酒,2006(6):13−16. [WU J F. Review on the study of tetramethylpyrazine, a healthy functional component in Chinese Baijiu[J]. Wine,2006(6):13−16. doi: 10.3969/j.issn.1002-8110.2006.06.009
[4]	郭学武, 范恩帝, 马冰涛, 等. 中国白酒中微量成分研究进展[J]. 食品科学,2020,41(11):267−276. [GUO X W, FAN E D, MA B T, et al. Research progress of trace components in Chinese Baijiu[J]. Food Science,2020,41(11):267−276. doi: 10.7506/spkx1002-6630-20190704-065
[5]	AKHLAGHI S, MOSTOUFI A, KALANTAR H, FEREIDOONNEZHAD M. Synthesis and biological evaluations of novel pyrazinoic acid derivatives as anticancer agents[J]. Medicinal Chemistry Research,2022,31(4):580−593.
[6]	金其璋. 食品香料的新成员-杂环化合物[J]. 化学通报,1984(1):31−37. [JIN Q Z. Heterocyclic compounds are new members of food flavoring[J]. Chemistry Bulletin,1984(1):31−37.
[7]	王奕芳, 周容, 张明春, 等. 白酒中重要的功能化合物吡嗪的研究进展[J]. 酿酒,2018,45(6):20−24. [WANG Y F, ZHOU R, ZHANG M C, et al. Research progress of pyrazine, an important functional compound in Baijiu[J]. Wine,2018,45(6):20−24. doi: 10.3969/j.issn.1002-8110.2018.06.009
[8]	余晓, 尹建军, 胡国栋. 白酒中含氮化合物的分析研究[J]. 酿酒,1992(1):71−76. [YU X, YIN J J, HU G D. Analysis of nitrogen compounds in Baijiu[J]. Wine,1992(1):71−76.
[9]	庄名扬. 再论美拉德反应产物与中国白酒的香和味[J]. 酿酒科技,2005(5):34−38. [ZHUANG M Y. On the aroma and taste of Maillard reaction products and Chinese Baijiu[J]. Baijiu-Making Science & Technology,2005(5):34−38. doi: 10.3969/j.issn.1001-9286.2005.05.005
[10]	杨亮, 占杨杨, 魏刚, 等. 基于气质联用法的两种香型白酒挥发性成分差异分析[J]. 中国酿造,2018,37(10):76−81. [YANG L, ZHAN Y Y, WEI G, et al. Difference analysis of volatile components in two flavor Baijiu based on GC-MS[J]. China Brewing,2018,37(10):76−81. doi: 10.11882/j.issn.0254-5071.2018.10.015
[11]	李正涛, 孙跃, 孙海燕, 等. GC-MS/MS-SRM技术在检测白酒中5种吡嗪类化合物的应用研究[J]. 酿酒科技,2020(5):17−21, 26. [LI Z T, SUN Y, SUN H Y, et al. Application of GC-MS/MS-SRM in determination of five pyrazine compounds in Baijiu[J]. Baijiu-making Technology,2020(5):17−21, 26. doi: 10.13746/j.njkj.2019329
[12]	王颖, 邱勇, 王隆, 等. 不同产区酱香型高温大曲黑、白、黄曲的理化、挥发性成分差异性分析[J]. 中国调味品,2022,47(6):155−159. [WANG Y, QIU Y, WANG L, et al. Analysis on the differences of physicochemical indexes and volatile components of black, white and yellow koji at high temperature with Maotai flavor in different production areas[J]. China Condiment,2022,47(6):155−159. doi: 10.3969/j.issn.1000-9973.2022.06.029
[13]	史改玲, 郭莹, 李景辉, 等. LLE-GC-MS-SIM检测白酒中9种微量功能成分[J]. 食品科学,2021,42(20):114−119. [SHI G L, GUO Y, LI J H, et al. Nine trace functional components in Baijiu were detected by LLE-GC-MS-SIM[J]. Food Science,2021,42(20):114−119. doi: 10.7506/spkx1002-6630-20200805-071
[14]	唐平, 山其木格, 王丽, 等. 白酒风味化学研究方法及酱香型白酒风味化学研究进展[J]. 食品科学,2020,41(17):315−324. [TANG P, SHAN Q M G, WANG L, et al. Research methods of flavor chemistry of Baijiu and progress in flavor chemistry of sauce flavor Baijiu[J]. Food Science,2020,41(17):315−324. doi: 10.7506/spkx1002-6630-20190822-228
[15]	林文轩, 敖灵, 董蔚, 等. 白酒风味物质前处理方法的研究进展[J]. 食品与发酵工业,2021,47(15):307−314. [LIN W X, AO L, DONG W, et al. Research progress on pretreatment methods of Baijiu flavor substances[J]. Food and Fermentation Industries,2021,47(15):307−314. doi: 10.13995/j.cnki.11-1802/ts.025867
[16]	夏磊. 浅谈白酒检测中存在的问题及对策[J]. 食品安全导刊,2021(24):63−64. [XIA L. Discussion on the problems and countermeasures in Baijiu testing[J]. Food Safety Guide,2021(24):63−64. doi: 10.16043/j.cnki.cfs.2021.24.039
[17]	吴成林, 胡家艺, 张惟广. 白酒风味物质研究进展及关键技术分析[J]. 食品研究与开发,2022,43(3):207−215. [WU C L, HU J Y, ZHANG W G. Research progress and key technologies of Baijiu flavor substances[J]. Food Research and Development,2022,43(3):207−215. doi: 10.12161/j.issn.1005-6521.2022.03.031
[18]	YAN Y, CHEN S, HE Y X, et al. Quantitation of pyrazines in Baijiu and during production process by a rapid and sensitive direct injection UPLC-MS/MS approach[J]. LWT-Food Science and Technology,2020,128:109371. doi: 10.1016/j.lwt.2020.109371
[19]	范三红, 李颖星, 白宝清. 涡旋辅助分散液液微萃取-气相色谱法测定清香型白酒中5种高级醇[J]. 中国酿造,2020,39(4):194−200. [FAN S H, LI Y X, BAI B Q. Determination of five higher alcohols in clear flavor Baijiu by vortex-assisted dispersive liquid-liquid microextraction and gas chromatography[J]. China Brewing,2020,39(4):194−200. doi: 10.11882/j.issn.0254-5071.2020.04.038
[20]	郭云霞, 李娜, 程伟, 等. 液液萃取与顶空固相微萃取结合气相色谱-质谱法分析金种子馥合香白酒香气成分的比较[J]. 食品安全质量检测学报,2021,12(23):9056−9061. [GUO Y X, LI N, CHENG W, et al. Comparison of aroma components in Jinzhongzi Fuhexiang Baijiu by liquid-liquid extraction and headspace solid phase microextraction combined with gas chromatography-mass spectrometry[J]. Journal of Food Safety and Quality Inspection,2021,12(23):9056−9061. doi: 10.3969/j.issn.2095-0381.2021.23.spaqzljcjs202123012
[21]	WANG M Y, ZHANG Q, YANG J G, et al. Volatile compounds of Chinese strong flavor Baijiu distilled from grains fermented in 100 to 300 year-old cellars[J]. Journal of the Institute of Brewing,2020,126(1):116−130. doi: 10.1002/jib.588
[22]	孙文佳, 汪廷彩, 雷毅, 等. 基于静态顶空-气质联用法分析酱香型白酒空杯香气成分[J]. 中国酿造,2021,40(11):93−97. [SUN W J, WANG Y C, LEI Y, et al. Lingering aroma composition in empty glass of sauce-flavor Baijiu by SHS-GC/MS[J]. China Brewing,2021,40(11):93−97. doi: 10.11882/j.issn.0254-5071.2021.11.017
[23]	WANG Z, WANG S, LIAO P F, et al. HS-SPME combined with GC-MS/O to analyze the flavor of strong aroma Baijiu Daqu[J]. Foods,2022,11(1):116. doi: 10.3390/foods11010116
[24]	ZHU J C, NIU Y W, XIAO Z B. Characterization of important sulfur and nitrogen compounds in Lang Bajiu by application of gas chromatography-olfactometry, flame photometric detection, nitrogen phosphorus detector and odor activity value[J]. Food Research International,2020,131:109001. doi: 10.1016/j.foodres.2020.109001
[25]	YANG L, FAN W L, XU Y. GC×GC-TOF/MS and UPLC-Q-TOF/MS based untargeted metabolomics coupled with physicochemical properties to reveal the characteristics of different type daqus for making soy sauce aroma and flavor type Baijiu[J]. LWT,2021,146:111−416.
[26]	王双. 利用高效液相-三重四极杆质谱分析中国传统酿造白酒中的芳香酯类物质[J]. 酿酒,2019,46(6):84−85. [WANG S. Analysis of aromatic esters in traditional Chinese Baijiu by high performance liquid chromatography-triple quadrupole mass spectrometry[J]. Wine,2019,46(6):84−85.
[27]	MA H C, CHEN Y T, HE Z Z, WEI Y H. Facile fluorescent glucose detection based on the Maillard reaction[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2022, 640: 128-339.
[28]	吴建峰. 白酒中四甲基吡嗪全程代谢机理研究[D]. 镇江: 江南大学, 2013. WU J F. Study on metabolism mechanism of tetramethylpyrazine in Baijiu[D]. Zhenjiang: Jiangnan University, 2013.
[29]	RIZZ G P. Mechanistic study of alkylpyrazine formation in model systems[J]. Agric Food Chemistry,1972,20(5):1081−1085. doi: 10.1021/jf60183a022
[30]	AMRANIHEMAIMI M, CERNY C, FAY L B, Mechanisms of formation of alkylpyrazines in the Maillard reation[J]. Journal of Agricultural and Food Chemistry, 1995, 43(11): 2818-2822.
[31]	DENG S B, CUI H P, HAYAT K, et al. Comparison of pyrazines formation in methionine/glucose and corresponding amadori rearrangement product model[J]. Food Chemistry,2022,382:132500. doi: 10.1016/j.foodchem.2022.132500
[32]	陈亨业. 山西老陈醋对晚期糖基化终末产物形成的抑制及产苯乳酸醋酸菌的发现[D]. 武汉: 华中农业大学, 2018. CHEN H Y. Inhibition of late glycation end product formation by Shanxi aged vinegar and discovery of phenyllactate acetic acid producing bacteria[D]. Wuhan: Huazhong Agricultural University, 2018.
[33]	DICKSCHAT J S, WICKEL S, BOLTEN C J, et al. Pyrazine biosynthesis in corynebacterium glutamicum[J]. Eur J Org Chem,2010,14:2687−2695.
[34]	张颖, 李霄霄, 李景辉, 等. 高产四甲基吡嗪芽孢杆菌的筛选及其对酱香型白酒堆积过程的影响[J]. 食品工业科技,2022,43(2):142−149. [ZHANG Y, LI X X, LI J H, et al. Screening of Bacillus tetramethylpyrazine with high yield and its effect on the accumulation process of sauce flavor Baijiu[J]. Science and Technology of Food Industry,2022,43(2):142−149. doi: 10.13386/j.issn1002-0306.2021050066
[35]	梁慧珍, 卢延想, 刘正, 等. 高温大曲中高产吡嗪类物质芽孢杆菌的筛选与应用[J]. 中国酿造,2022,41(1):116−122. [LIANG H Z, LU Y X, LIU Z, et al. Screening and application of high yield pyrazine Bacillus in high temperature Daqu[J]. China Brewing,2022,41(1):116−122. doi: 10.11882/j.issn.0254-5071.2022.01.020
[36]	FREY, CARL; ROUSEFF, RUSSELL, et al. Chocarom pyrazine: A remarkable pyrazine for flavors and fragrances[J]. ACS Symposium Series, 2005, 908: 189–202.
[37]	范文来, 徐岩. 白酒79个风味化合物嗅觉阈值测定[J]. 酿酒,2011,38(4):80−84. [FAN W L, XU Y. Determination of olfactory threshold of 79 flavor compounds in Baijiu[J]. Wine,2011,38(4):80−84. doi: 10.3969/j.issn.1002-8110.2011.04.034
[38]	HE Y X, LIU Z P, QIAN M, et, al. Unraveling the chemosensory characteristics of strong-aroma type Baijiu from different regions using comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry and descriptive sensory analysis[J]. Food Chemistry,2022,331:127335.
[39]	熊小月, 李利利, 马宇, 等. 酱香白酒酿造轮次醇甜典型体基酒风味解析[J]. 食品与发酵工业,2022,48(13):261−267. [XIONG X Y, LI L L, MA Y, et al. Flavor analysis of typical body base Baijiu in sauce-fragrant Baijiu brewing[J]. Food and Fermentation Industries,2022,48(13):261−267. doi: 10.13995/j.cnki.11-1802/ts.031167
[40]	孙宝国, 李贺贺, 胡萧梅, 等. 健康白酒的发展趋势[J]. 中国食品,2021,2021(S1):11−14. [SUN B G, LI H H, HU X M, et al. Development trend of healthy Baijiu[J]. Chinese Food,2021,2021(S1):11−14.
[41]	孙宝国, 黄明泉, 王娟. 白酒风味化学与健康功效研究进展[J]. 中国食品学报,2021,21(5):1−13. [SUN B G, HUANG M Q, WANG J. Research progress on flavor chemistry and health efficacy of Baijiu[J]. Chinese Journal of Food Science,2021,21(5):1−13. doi: 10.16429/j.1009-7848.2021.05.001
[42]	罗强, 刘杰, 刘志刚. 酱香型白酒中吡嗪类物质体外抗炎作用研究[J]. 中国酿造,2019,38(7):156−160. [LUO Q, LIU J, LIU Z G. Anti-inflammatory effect of pyrazines in sauce flavor Baijiu in vitro[J]. China Brewing,2019,38(7):156−160. doi: 10.11882/j.issn.0254-5071.2019.07.031
[43]	罗强, 刘杰, 刘志刚. 酱香型白酒中生物活性物质抗幽门螺杆菌代谢物诱导的人胃上皮细胞炎症作用研究[J]. 食品与发酵科技,2020,56(4):11−17. [LUO Q, LIU J, LIU Z G. Effect of bioactive substances in sauce flavor Baijiu on human gastric epithelial cell inflammation induced by Helicobacter pylori metabolites[J]. Food and Fermentation Technology,2020,56(4):11−17.
[44]	ROBERT W, HUIGENS II I, BEAU R, et al. Pyrazine and phenazine heterocycles: Platforms for total synthesis and drug discovery[J]. Molecules,2022,27(3):1112. doi: 10.3390/molecules27031112
[45]	BAZZANO L A, GU D F, REYNOLDS K, et al. Alcohol consumption and risk of coronary heart disease among Chinese men[J]. International Journal of Cardiology,2009,135(1):78−85. doi: 10.1016/j.ijcard.2008.03.038
[46]	WANG X X, JIA M, MAO Y F, et al. Very-light alcohol consumption suppresses breast tumor progression in a mouse model[J]. Food and Function,2022,13(6):3391−3404. doi: 10.1039/D1FO02089G
[47]	ZHANG Y Q, WU J B, YIN W, et al. Design, synthesis, and biological evaluation of ligustrazine/resveratrol hybrids as potential anti-ischemic stroke agents[J]. Chinese Journal of Natural Medicines,2020,18(8):633−640. doi: 10.1016/S1875-5364(20)30076-5
[48]	HAN X K, CHEN X, CHEN S L, et al. Tetramethylpyrazine attenuates endotoxin-induced retinal inflammation by inhibiting microglial activation via the TLR4/NF-κB signalling pathway[J]. Biomedicine & Pharmacotherapy,2020,128:110−273.
[49]	CHEN L J, PANG X, HAO C S, et al. Prevention of neointimal formation after angioplasty using tetramethylpyrazine-coated balloon catheters in a rabbit iliac artery model[J]. Cardioavscular Diagnosis and Therapy,2019,9(5):472−480. doi: 10.21037/cdt.2019.09.04
[50]	JIA J, ZHANG X, HU Y X, et al. Protective effect of tetraethylpyrazine against focal cerebral ischemia/reperfusion injury inrats: Therapeutic time window and its mechanism[J]. Thrombosis Research,2019,123(5):727−730.
[51]	TENG F M, SHEN M H, WANG L, et al. Ultrasound/microbubble-mediated tetramethylpyrazine for neuroprotection against cerebral ischemia/reperfusion-injured rat brain[J]. Applied Acoustics,2021,183:108330. doi: 10.1016/j.apacoust.2021.108330
[52]	ZHAI L, JIA Y L, JI Y Q, et al. Protective effects of tetramethylpyrazine analogue Z-11 on cerebral ischemia reperfusion injury[J]. European Journal of Pharmacology,2019,844:156−164. doi: 10.1016/j.ejphar.2018.11.031
[53]	ZHU T, FANG B Y, MENG X B, et al. Folium ginkgo extract and tetramethylpyrazine sodium chloride injection (Xingxiong injection) protects against focal cerebral ischaemia/reperfusion injury via activating the Akt/Nrf2 pathway and inhibiting NLRP3 inflammasome activation[J]. Pharmaceutical Biology,2022,60(1):195−205. doi: 10.1080/13880209.2021.2014895
[54]	ZHANG C B, SHEN M H, TENG F M, et al. Ultrasound-enhanced protective effect of tetramethylpyrazine via the ROS/HIF-1A signaling pathway in an in vitro cerebral ischemia/reperfusion injury model[J]. Ultrasound in Medicine & Biology,2018,44:1786−1798.
[55]	HAIDY E M, ESTHER T M. Tetramethylpyrazine guards against cisplatin-induced nephrotoxicity in rats through inhibiting HMGB1/TLR4/NF-κB and activating Nrf2 and PPAR-γ signaling pathways[J]. European Journal of Pharmacology,2019,857:172−422.
[56]	MENG Z Y, CHEN H Z, MENG S X. The roles of tetramethylpyrazine during neurodegenerative disease[J]. Neurotoxicity Research,2021,39(5):1665−1677. doi: 10.1007/s12640-021-00398-y
[57]	ZHOU Y, WU R M, WANG X Q, et al. Activation of UQCRC2-dependent mitophagy by tetramethylpyrazine inhibits MLKL-mediated hepatocyte necroptosis in alcoholic liver disease[J]. Free Radical Biology and Medicine,2022,179:301−316. doi: 10.1016/j.freeradbiomed.2021.11.008
[58]	LI Y J, LIU R P, DING M N. Tetramethylpyrazine prevents liver fibrotic injury in mice by targeting hepatocyte-derived and mitochondrial DNA-enriched extracellular vesicles[J]. Acta Pharmacologica Sinica,2022,43:2026−2041. doi: 10.1038/s41401-021-00843-w
[59]	LI J, GONG X Z. Tetramethylpyrazine: An active ingredient of chinese herbal medicine with therapeutic potential in acute kidney injury and renal fibrosis[J]. Frontiers in Pharmacology,2022,13:820071. doi: 10.3389/fphar.2022.820071
[60]	YANG S J, WU S D, DAI W L, et al. Tetramethylpyrazine: A review of its antitumor potential and mechanisms[J]. Frontiers in Pharmacology,2022,12:764331.
[61]	REN J, CAI J P, WANG C F. Tetramethylpyrazine inhibits the proliferation, invasiveness and migration of cervical cancer C33A cells by retarding the Hedgehog signaling pathway[J]. Oncology Letters,2022,23(2):66. doi: 10.3892/ol.2022.13185
[62]	HU S, WANG S, HE J, et al. Tetramethylpyrazine alleviates endoplasmic reticulum stress-activated apoptosis and related inflammation in chondrocytes[J]. Molecular Medicine Reporets,2021,25(1):12. doi: 10.3892/mmr.2021.12528