Formation of DDMP, HMF and Furfural in Caramelization and Maillard Reaction

WANG Dan; KUANG Danni; LIU Ruoyang; ZHANG Zhijun; HOU Tianyu; LI He

doi:10.13386/j.issn1002-0306.2021090221

Volume 43 Issue 12

Jun. 2022

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2022 > 43(12): 100-107. > DOI: 10.13386/j.issn1002-0306.2021090221

WANG Dan, KUANG Danni, LIU Ruoyang, et al. Formation of DDMP, HMF and Furfural in Caramelization and Maillard Reaction[J]. Science and Technology of Food Industry, 2022, 43(12): 100−107. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021090221.

Citation:

PDF (2702 KB)

Formation of DDMP, HMF and Furfural in Caramelization and Maillard Reaction

School of Chemical Engineering and Technology, North University of China, Taiyuan 030051, China

More Information

Received Date: September 17, 2021
Available Online: April 14, 2022

Graphical Abstract

Abstract

Abstract

Maillard reaction (MR) is widely found in food heat processing, can not only give food color and flavor, but also produce harmful or odorous substances. 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one (DDMP), 5-hydroxymethylfurfural (HMF) and furfural are important products of MR. In this paper, three kinds of caramelization and three kinds of Maillard reaction models were established to study the formation of DDMP, HMF and furfural. Results indicated that HMF and furfural were easily generated in fructose and xylose caramelization models, respectively. In Maillard reaction model, the participation of lysine inhibited the production of HMF and furfural, and promoted the production of DDMP. Combined with the characterization of the intermediate product and the final product, the structural difference of monosaccharides was the main factor affecting the production of the three compounds. Lysine competitively inhibited the caramelization pathway of monosaccharide degradation, thereby inhibiting the production of HMF and furfural. The present paper would provide guidance on the production, control and oriented synthesis of DDMP, HMF and furfural in food thermal processing industry.
- 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one,
- 5-hydroxymethylfurfural,
- furfural,
- caramelization,
- Maillard reaction

FullText(HTML)

References (37)

References

[1]	张玉玉, 宋弋, 李全宏. 食品中糠醛和5-羟甲基糠醛的产生机理、含量检测及安全性评价研究进展[J]. 食品科学,2012(5):275−280. [ZHANG Yuyu, SONG Yi, LI Quanhong. A review on formation mechanism, determination and safety assessment of furfural and 5-hydroxymethylfurfural (HMF) in foods[J]. Food Science,2012(5):275−280. ZHANG Yuyu, SONG Yi, LI Quanhong. A review on formation mechanism, determination and safety assessment of furfural and 5-hydroxymethylfurfural (HMF) in foods[J]. Food Science, 2012(5): 275-280.
[2]	李河. 美拉德反应中主要苦味物质的形成途径与调控机制研究[D]. 广州: 华南理工大学, 2019. LI He. Study on the formation pathway and regulation mechanism of main bitter compounds in Maillard reaction [D]. Guangzhou: South China University of Technology, 2019.
[3]	张燕, 郭天鑫, 于姣, 等. 离子交换固相萃取高效液相色谱联用法检测食品中的5-羟甲基糠醛[J]. 食品科学,2010,31(18):212−215. [ZHANG Yan, GUO Tianxin, YU Jiao, et al. Development of ion-exchange solid phase extraction and high performance liquid chromatography for the determination of 5-hydroxymethyl-furfural in food[J]. Food Science,2010,31(18):212−215. ZHANG Yan, GUO Tianxin, YU Jiao, et al. Development of ion-exchange solid phase extraction and high performance liquid chromatography for the determination of 5-hydroxymethyl-furfural in food[J]. Food Science, 2010, 31(18): 212-215.
[4]	TOMASINI D, SAMPAIO M R F, CALDAS S S, et al. Simultaneous determination of pesticides and 5-hydroxymethylfurfural in honey by the modified QuEChERS method and liquid chromatography coupled to tandem mass spectrometry[J]. Talanta,2012,99:380−386. doi: 10.1016/j.talanta.2012.05.068
[5]	YILTIRAK S, KOCADAĞLI T, ÇELIK E E, et al. Effects of sprouting and fermentation on free asparagine and reducing sugars in wheat, einkorn, oat, rye, barley, and buckwheat and on acrylamide and 5-hydroxymethylfurfural formation during heating[J]. Journal of Agricultural and Food Chemistry,2021,69(32):9419−9433. doi: 10.1021/acs.jafc.1c03316
[6]	GÜRSUL A I, VURAL G. Investigations on the formation of α-dicarbonyl compounds and 5-hydroxymethylfurfural in fruit products during storage: New insights into the role of Maillard reaction[J]. Food Chemistry,2021:363.
[7]	GONG M, ZHOU Z, YU Y, et al. Investigation of the 5-hydroxymethylfurfural and furfural content of Chinese traditional fermented vinegars from different regions and its correlation with the saccharide and amino acid content[J]. LWT,2020,124:109175. doi: 10.1016/j.lwt.2020.109175
[8]	JIANG D S, PETERSON D G. Identification of bitter compounds in whole wheat bread[J]. Food Chemistry,2013,141(2):1345−1353. doi: 10.1016/j.foodchem.2013.03.021
[9]	WANG, Zihan, ZHANG, Jingxian, GAO Ming, et al. Stable isotope labelling-flow injection analysis-mass spectrometry for rapid and high throughput quantitative analysis of 5-hydroxymethylfurfural in drinks[J]. Food Control,2021:130.
[10]	邓丽卿. 酱油焦糖色素及油溶性焦糖色素的制备与性质研究[D]. 广州: 华南理工大学, 2014. DENG Liqing. Study of caramel pigment for soy sauce and oil stability caramel pigment processing and property[D]. Guangzhou: South China University of Technology, 2014.
[11]	GAO H, WEN X, XIAN C J. Hydroxymethyl furfural in Chinese herbal medicines: Its formation, presence, metabolism, bioactivities and implications[J]. African Journal of Traditional Complementary and Alternative Medicines,2015,12(2):43−54. doi: 10.4314/ajtcam.v12i2.9
[12]	徐斌, 张强, 刘亮镜. 丹参酒炙过程中炮制时间、颜色与化学成分含量的相关性[J]. 中国药房,2021,32(14):1715−1720. [XU Bin, ZHANG Qiang, LIU Liangjing. Correlation between processing time, color and chemical composition content in the wine-fried process of Salvia miltiorrhi[J]. China Pharmacy,2021,32(14):1715−1720. doi: 10.6039/j.issn.1001-0408.2021.14.09 XU Bin, ZHANG Qiang, LIU Liangjing. Correlation between processing time, color and chemical composition content in the wine-fried process of Salvia miltiorrhi[J]. China Pharmacy, 2021, 32(14): 1715-1720. doi: 10.6039/j.issn.1001-0408.2021.14.09
[13]	SHARMA V K, CHOI J, SHARMA N, et al. In vitro anti-tyrosinase activity of 5-(hydroxymethyl)-2-furfural isolated from Dictyophora indusiata[J]. Phytotherapy Research: PTR,2004,18(10):841−844. doi: 10.1002/ptr.1428
[14]	YU X, ZHAO M, LIU F, et al. Identification of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one as a strong antioxidant in glucose-histidine Maillard reaction products[J]. Food Research International,2013,51(1):397−403. doi: 10.1016/j.foodres.2012.12.044
[15]	CECHOVSKA L, CEJPEK K, KONECNY M, et al. On the role of 2,3-dihydro-3,5-dihydroxy-6-methyl-(4H)-pyran-4-one in antioxidant capacity of prunes[J]. European Food Research and Technology,2011,233(3):367−376. doi: 10.1007/s00217-011-1527-4
[16]	BAN J O, HWANG I G, KIM T M, et al. Anti-proliferate and pro-apoptotic effects of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyranone through inactivation of NF-kappa B in human colon cancer cells[J]. Archives of Pharmacal Research,2007,30(11):1455−1463. doi: 10.1007/BF02977371
[17]	张泽宇, 曹雁平, 朱雨辰. 缓解食品中丙烯酰胺和5-羟甲基糠醛形成的研究进展[J]. 食品工业科技,2020,41(12):324−333. [ZHANG Zeyu, CAO Yanping, ZHU Yuchen. Mitigation strategies on acrylamide and 5-hydroxymethylfurfural in foods[J]. Science and Technology of Food Industry,2020,41(12):324−333. ZHANG Zeyu, CAO Yanping, ZHU Yuchen. Mitigation Strategies on Acrylamide and 5-Hydroxymethylfurfural in Foods[J]. Science and Technology of Food Industry, 2020, 41(12): 324-333.
[18]	BAKHIYA N, MONIEN B, FRANK H, et al. Renal organic anion transporters OAT1 and OAT3 mediate the cellular accumulation of 5-sulfooxymethylfurfural, a reactive nephrotoxic metabolite of the Maillard product 5-hydroxymethylfurfural[J]. Biochemical Pharmacology,2009,78:414−419. doi: 10.1016/j.bcp.2009.04.017
[19]	章银良, 周文权. 美拉德反应产物5-羟甲基糠醛含量与抗氧化活性关系研究[J]. 中国调味品,2013(1):36−40. [ZHANG Yinliang, ZHOU Wenquan. Investigation of the correlation between 5-HMF content and antioxidant activities of MRPs[J]. China Condiment,2013(1):36−40. doi: 10.3969/j.issn.1000-9973.2013.01.011 ZHANG Yinliang, ZHOU Wenquan. Investigation of the correlation between 5-HMF content and antioxidant activities of MRPs[J]. China Condiment, 2013(1): 36-40. doi: 10.3969/j.issn.1000-9973.2013.01.011
[20]	曾稳稳, 刘玉环, 阮榕生, 等. 美拉德反应所引起的食品安全问题的研究进展[J]. 食品工业科技,2011,32(7):447−450. [ZENG Wenwen, LIU Yuhuan, YUAN Rongsheng et al. Research progress in food safety issue caused by Maillard reaction[J]. Science and Technology of Food Industry,2011,32(7):447−450. ZENG Wenwen, LIU Yuhuan, YUAN Rongsheng et al. Research proqress in food safety issue caused by Maillard reaction[J]. Science and Technology of Food Industry, 2011, 32(7): 447-450.
[21]	HIRAMOTO K, NASUHARA A, MICHIKOSHI K, et al. DNA strand-breaking activity and mutagenicity of 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP), a Maillard reaction product of glucose and glycine[J]. Mutation Research-Genetic Toxicology and Environmental Mutagenesis,1997,395(1):47−56. doi: 10.1016/S1383-5718(97)00141-1
[22]	BEPPU Y, KOMURA H, IZUMO T, et al. Identificaton of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one isolated from Lactobacillus pentosus strain S-PT84 culture supernatants as a compound that stimulates autonomic nerve activities in rats[J]. Journal of Agricultural and Food Chemistry,2012,60(44):11044−11049. doi: 10.1021/jf302355e
[23]	LI H, ZHANG W, TANG X, et al. Identification of bitter-taste compounds in class-III caramel colours[J]. Flavour and Fragrance Journal,2021,36(3):404−411. doi: 10.1002/ffj.3652
[24]	欧隽滢, 江楷煜, 高瑜悦, 等. 3种添加物抑制模拟体系中羟甲基糠醛(HMF)的形成[J]. 现代食品科技, 2021, 37(7): 286-293. OU Juanying, JIANG Kaiyu, GAO Yuyue, et al. Reduction of hydroxymethylfurfural (HMF) via three additives in model reaction system[J]. Modern Food Science and Technology, 2021, 37(7): 286-293.
[25]	JANZOWSKI C, GLAAB V, SAMIMI E, et al. 5-Hydroxymethylfurfural: Assessment of mutagenicity, DNA-damaging potential and reactivity towards cellular glutathione[J]. Food Chem Toxicol,2000,38(9):801−809. doi: 10.1016/S0278-6915(00)00070-3
[26]	卢键媚, 林晓蓉, 陈忠正, 等. 反应条件对糖-酸反应体系中3-脱氧葡萄糖醛酮及5-羟甲基糠醛形成的影响[J]. 食品工业科技,2021:1−14. [LU Jianmei, LIN Xiaorong, CHEN Zhongzheng, et al. Effect of reaction conditions on the formation of 3-deoxyglucosone and 5-hydroxymethylfurfural in sugar-acid reaction system[J]. Science and Technology of Food Industry,2021:1−14. LU Jianmei, LIN Xiaorong, CHEN Zhongzheng, et al. Effect of reaction conditions on the formation of 3-deoxyglucosone and 5-hydroxymethylfurfural in sugar-acid reaction system[J]. Science and Technology of Food Industry, 2021: 1-14.
[27]	LI H, TANG X, WU C, et al. Formation of 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4(H)-pyran-4-one (DDMP) in glucose-amino acids Maillard reaction by dry-heating in comparison to wet-heating[J]. LWT-Food Science and Technology,2019,105:156−163. doi: 10.1016/j.lwt.2019.02.015
[28]	LI H, WU C, TANG X, et al. Determination of four bitter compounds in caramel colors and beverages using modified QuEChERS coupled with liquid chromatography-diode array detector-mass spectrometry[J]. Food Analytical Methods,2019,12(7):1674−1683. doi: 10.1007/s12161-019-01500-z
[29]	LI H, WU C, YU S. Impact of microwave-assisted heating on the pH value, color, and flavor compounds in glucose-ammonium model system[J]. Food and Bioprocess Technology,2018,11(6):1248−1258. doi: 10.1007/s11947-018-2093-6
[30]	HUYGHUES-DESPOINTES A, YAYLAYAN V A, KEYHANI A. Pyrolysis/GC/MS analysis of 1-[(2'-carboxy)pyrrolidinyl]-1-deoxy-D-fructose (proline amadori compound)[J]. Journal of Agricultural and Food Chemistry,1994(42):2519−2524.
[31]	LUND M N, RAY C A. Control of Maillard reactions in foods: Strategies and chemical mechanisms[J]. Journal of Agricultural and Food Chemistry,2017,65(23):4537−4552. doi: 10.1021/acs.jafc.7b00882
[32]	LI H, WU C, TANG X, et al. Insights into the regulation effects of certain phenolic acids on 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one formation in a microaqueous glucose–proline system[J]. Journal of Agricultural and Food Chemistry,2019,67(32):9050−9059. doi: 10.1021/acs.jafc.9b01182
[33]	HONG X, MENG J, LU R. Improvement of ACE inhibitory activity of casein hydrolysate by Maillard reaction with xylose[J]. Journal of the Science of Food and Agriculture,2015,95(1):66−71. doi: 10.1002/jsfa.6682
[34]	O'CHAROEN S, HAYAKAWA S, OGAWA M. Food properties of egg white protein modified by rare ketohexoses through Maillard reaction[J]. International Journal of Food Science and Technology,2015,50(1):194−202. doi: 10.1111/ijfs.12607
[35]	HELLWIG M, NOBIS A, WITTE S, et al. Occurrence of (Z)-3,4-dideoxyglucoson-3-ene in different types of beer and malt beer as a result of 3-deoxyhexosone interconversion[J]. Journal of Agricultural and Food Chemistry,2016,64(13):2746−2753. doi: 10.1021/acs.jafc.6b00468
[36]	KANZLER C, SCHESTKOWA H, HAASE P T, et al. Formation of reactive intermediates, color, and antioxidant activity in the Maillard reaction of maltose in comparison to D-glucose[J]. Journal of Agricultural and Food Chemistry,2017,65(40):8957−8965. doi: 10.1021/acs.jafc.7b04105
[37]	ZHU H, POOJARY M M, ANDERSEN M L, et al. The effect of molecular structure of polyphenols on the kinetics of the trapping reactions with methylglyoxal[J]. Food Chemistry, 2020, 319(126500).

Supplements (0)

Cited By

Cited by

Periodical cited type(2)

1.	阮斯佳，赵欣欣，王燕，柳李旺，屠康，彭菁. 基于响应面和人工神经网络-遗传算法优化鲜切萝卜光动力杀菌工艺. 南京农业大学学报. 2023(06): 1196-1205 .
2.	贺弘扬. 融合径向基神经网络和遗传算法的翻板钢水闸门优化. 粘接. 2022(12): 133-136 .