综述与专题评论

4-羟基-2,5-二甲基-3(2H)-呋喃酮的生物与非生物的合成途径研究进展

  • 俞兆斌 ,
  • 朱丽霞
展开
  • 1(塔里木大学 食品科学与工程学院,新疆 阿拉尔,843300);
    2(南疆特色农产品深加工兵团重点实验室,新疆 阿拉尔,843300)
第一作者:硕士研究生(朱丽霞教授为通信作者,E-mail:120050068@taru.edu.cn)

收稿日期: 2023-03-22

  修回日期: 2023-04-25

  网络出版日期: 2024-03-15

基金资助

国家自然基金项目(32272457)

Review on biologically and abiotically synthesis of 4-hydroxy-2,5-dimethyl-3(2H)-furanone

  • YU Zhaobin ,
  • ZHU Lixia
Expand
  • 1(School of Food Science and Engineering, Tarim University, Aral 843300, China)
    2(South Xinjiang Special Agricultural Products Deep Processing Corps Key Laboratory, Aral 843300, China)

Received date: 2023-03-22

  Revised date: 2023-04-25

  Online published: 2024-03-15

摘要

4-羟基-2,5-二甲基-3(2H)-呋喃酮(4-hydroxy-2,5-dimethyl-3(2H)-furanone,HDMF)是一种具有焦糖香的天然活性产物,在食品工业中具有极高的应用价值。该文对HDMF化学合成、美拉德反应、酶法催化、植物合成代谢以及微生物合成途径进行了全面阐述。化学合成为工业合成主要方法,但是存在原料价格昂贵、溶剂残留等问题;美拉德反应是热加工食品中形成HDMF的重要方式;植物合成代谢途径是农产品中形成HDMF的重要途径,形成路径较为清晰,但工业应用受到限制;微生物合成HDMF具有绿色可持续发展特性,但相关研究滞后,微生物代谢途径目前不清晰或存在争议,缺乏对关键底物、代谢途径及关键酶系等的基础认知,是今后利用微生物途径合成HDMF急需要解决的重要科学问题。

本文引用格式

俞兆斌 , 朱丽霞 . 4-羟基-2,5-二甲基-3(2H)-呋喃酮的生物与非生物的合成途径研究进展[J]. 食品与发酵工业, 2024 , 50(4) : 329 -336 . DOI: 10.13995/j.cnki.11-1802/ts.035573

Abstract

4-Hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) is a naturally active product with a strong caramel flavor, which is important for the food industry. In this paper, chemical synthesis, produce via the Maillard reaction, enzymatic catalysis, and plant and microbial synthesis of HDMF were reviewed. Chemical synthesis of furaneol is the main method of industrial synthesis, but there are problems such as costly materials and high residues. Maillard reaction and plant synthesis are important ways of HDMF in heated food and agricultural products. The formation path in the Maillard reaction and plant are relatively clear respectively, but they have not yet been used to control and utilize in industry production; Microbial synthesis of HDMF has the advantage of green and sustainable development, however research on it has fallen behind. The research on microbial metabolic pathways is unclear or controversial at present, with the lack of basic knowledge of key substrates, metabolic pathways, key enzymes, etc. It is an important scientific problem that needs to be urgently solved in the future to control and utilization of microbiology synthesis to product furaneol.

参考文献

[1] VANDAMME E J. Bioflavours and fragrances via fungi and their enzymes[J]. Fungal Diversity, 2003, 13:153-166.
[2] EFFENBERGER I, HOFFMANN T, JONCZYK R, et al. Novel biotechnological glucosylation of high-impact aroma chemicals, 3(2H)-and 2(5H)-furanones[J]. Scientific Reports, 2019, 9(1):10943.
[3] ROSCHER R, KOCH H, HERDERICH M, et al. Identification of 2, 5-dimethyl-4-hydroxy-3[2H]-furanone beta-D-glucuronide as the major metabolite of a strawberry flavour constituent in humans[J]. Food and Chemical Toxicology: an International Journal Published for the British Industrial Biological Research Association, 1997, 35(8):777-782.
[4] FERREIRA V, ORTÍN N, ESCUDERO A, et al. Chemical characterization of the aroma of Grenache rosé wines: Aroma extract dilution analysis, quantitative determination, and sensory reconstitution studies[J]. Journal of Agricultural and Food Chemistry, 2002, 50(14):4048-4054.
[5] LARSEN M, POLL L. Odour thresholds of some important aroma compounds in strawberries[J]. Zeitschrift Für Lebensmittel-Untersuchung Und Forschung, 1992, 195(2):120-123.
[6] 易玲敏. 呋喃酮的制备及其绿色工艺设计[D]. 杭州: 浙江大学, 2002.
YI L M. Preparation of 2, 5-dimethyl-4-hydroxy-3 (2H)-furanone and its green design[D].Hangzhou: Zhejiang University, 2002.
[7] COLIN S J. The naturally occurring furanones: Formation and function from pheromone to food[J]. Biological Reviews of the Cambridge Philosophical Society, 1999, 74(3):259-276.
[8] XIAO Q, HUANG Q R, HO C T. Occurrence, formation, stability, and interaction of 4-hydroxy-2, 5-dimethyl-3(2H)-furanone[J]. ACS Food Science & Technology, 2021, 1(3):292-303.
[9] SASAKI T, YAMAKOSHI J, SAITO M, et al. Antioxidative activities of 4-hydroxy-3(2H)-furanones and their anti-cataract effect on spontaneous cataract rat (ICR/f)[J]. Bioscience, Biotechnology, and Biochemistry, 1998, 62(10):1865-1869.
[10] SUNG W S, JUNG H J, LEE I S, et al. Antimicrobial effect of furaneol against human pathogenic bacteria and fungi[J]. Journal of Microbiology and Biotechnology, 2006, 16:349-354.
[11] KATAOKA S, LIU W, ALBRIGHT K, et al. Inhibition of benzo[a]pyrene-induced mouse forestomach neoplasia and reduction of H2O2 concentration in human polymorphonuclear leucocytes by flavour components of Japanese-style fermented soy sauce[J]. Food and Chemical Toxicology, 1997, 35(5):449-457.
[12] YOKOYAMA I, OHATA M, KOMIYA Y, et al. Inhalation of odors containing DMHF generated by the Maillard reaction affects physiological parameters in rats[J]. Scientific Reports, 2020, 10(1):13931.
[13] OHATA M, ZHOU L X, YADA Y, et al. 2, 3-Dimethylpyrazine (3DP) and 2, 5-dimethyl-4-hydroxy-3(2 H)-furanone (DMHF) generated by the Maillard reaction in foods affect autonomic nervous activity and central nervous activity in human[J]. Bioscience, Biotechnology, and Biochemistry, 2020, 84(9):1894-1902.
[14] RE L, MAURER B, OHLOFF G. Ein einfacher Zugang zu 4-hydroxy-2, 5-dimethyl-3(2H)-furanon (furaneol), einem aromabestandteil von Ananas und erdbeere[J]. Helvetica Chimica Acta, 1973, 56(6):1882-1894.
[15] BUECHI G, DEMOLE E, THOMAS A F. Syntheses of 2, 5-dimethyl-4-hydroxy-2, 3-dihydrofuran-3-one (furaneol), a flavor principle of pineapple and strawberry[J]. The Journal of Organic Chemistry, 1973, 38(1):123-125.
[16] ZABETAKIS I, GRAMSHAW J W, ROBINSON D S. 2, 5-Dimethyl-4-hydroxy-2H-furan-3-one and its derivatives: Analysis, synthesis and biosynthesis—A review[J]. Food Chemistry, 1999, 65(2):139-151.
[17] WANG Y, HO C T. Formation of 2, 5-dimethyl-4-hydroxy-3(2H)-furanone through methylglyoxal: A Maillard reaction intermediate[J]. Journal of Agricultural and Food Chemistry, 2008, 56(16):7405-7409.
[18] SCHIEBERLE P. ACS Symposium Series[M]. Washington: American Chemical Society, 1992:164-174.
[19] HAUCK T, LANDMANN C, RAAB T, et al. Chemical formation of 4-hydroxy-2, 5-dimethyl-3[2H]-furanone from D-fructose 1, 6-diphosphate[J]. Carbohydrate Research, 2002, 337(13):1185-1191.
[20] DUBAL S A, TIKARI P, MOMIN S A, et al. Biotechnological routes in flavour industries[J]. Advanced Biotech, 2008(14): 20-31.
[21] WONG C H, MAZENOD F P, WHITESIDES G M. Chemical and enzymatic syntheses of 6-deoxyhexoses. conversion to 2, 5-dimethyl-4-hydroxy-2, 3-dihydrofuran-3-one (furaneol) and analogs[J]. The Journal of Organic Chemistry, 1983, 48(20):3493-3497.
[22] RAAB T, LÓPEZ-RÁEZ J A, KLEIN D, et al. FaQR, required for the biosynthesis of the strawberry flavor compound 4-hydroxy-2, 5-dimethyl-3(2H)-furanone, encodes an enone oxidoreductase[J]. The Plant Cell, 2006, 18(4):1023-1037.
[23] KLEIN D, FINK B, AROLD B, et al. Functional characterization of enone oxidoreductases from strawberry and tomato fruit[J]. Journal of Agricultural and Food Chemistry, 2007, 55(16):6705-6711.
[24] 隋静. 草莓果实发育过程和采后处理对其芳香物质和醇酰基转移酶活性影响研究[D]. 泰安: 山东农业大学, 2007.
SUI J. Effects of fruit development period and post-harvest treatment on aromatic substances and AAT activity in strawberry[D].Taian: Shandong Agricultural University, 2007.
[25] KOBAYASHI, SASAKI, TANZAWA, et al. Impact of harvest timing on 4-hydroxy-2, 5-dimethyl-3(2H)-furanone concentration in ‘Muscat Bailey a’ grape berries[J]. Vitis: Journal of Grapevine Research, 2013, 52(1):9-11.
[26] UBEDA C, SAN-JUAN F, CONCEJERO B, et al. Glycosidically bound aroma compounds and impact odorants of four strawberry varieties[J]. Journal of Agricultural and Food Chemistry, 2012, 60(24):6095-6102.
[27] ROSCHER R, HILKERT A, GESSNER M, et al. L-Rhamnose: Progenitor of 2, 5-dimethyl-4-hydroxy-3[2H]-furanone formation by Pichia capsulata?[J]. Zeitschrift Für Lebensmitteluntersuchung Und -Forschung A, 1997, 204(3):198-201.
[28] HAYASHIDA Y, SLAUGHTER J C. Biosynthesis of flavour-active furanones by Saccharomyces cerevisiae during fermentation depends on the malt type used in medium preparation[J]. Biotechnology Letters, 1997, 19(5):429-431.
[29] HAYASHIDA Y, NISHIMURA K, SLAUGHTER C J. Formation mechanisms of flavour-active furanones, 4-hydroxy-2, 5-dimethyl-3 (2 H)-furanone (HDMF) and 4-hydorxy-2 (or 5)-ethyl-5 (or 2)-methyl-3 (2 H)-furanone (HEMF), in mugi-miso, fermented soy-beans paste with barley-koji[J]. JOURNAL OF THE BREWING SOCIETY OF JAPAN, 1998, 93(9):730-738.
[30] HECQUET L, SANCELME M, BOLTE J, et al. Biosynthesis of 4-hydroxy-2, 5-dimethyl-3(2h)-furanone by Zygosaccharomyces rouxii[J]. Journal of Agricultural and Food Chemistry, 1996, 44(5):1357-1360.
[31] HAYASHIDA Y, HATANO M, TAMURA Y, et al. 4-Hydroxy-2, 5-dimethyl-3(2H)-furanone (HDMF) production in simple media by lactic acid bacterium, Lactococcus lactis subsp. cremoris IFO 3427[J]. Journal of Bioscience and Bioengineering, 2001, 91(1):97-99.
[32] ZHU L X, ZHANG M M, LIU Z, et al. Levels of furaneol in msalais wines: A comprehensive overview of multiple stages and pathways of its formation during msalais winemaking[J]. Molecules, 2019, 24(17):3104.
[33] PREININGER M, GROSCH W. Determination of 4-hydroxy-2, 5-dimethyl-3 (2H)-furanone (HDMF) in cultures of bacteria[J]. Zeitschrift Für Lebensmittel-Untersuchung Und Forschung, 1995, 201(1):97-98.
[34] NSOGNING DONGMO S, SACHER B, KOLLMANNSBERGER H, et al. Key volatile aroma compounds of lactic acid fermented malt based beverages-impact of lactic acid bacteria strains[J]. Food Chemistry, 2017, 229:565-573.
[35] 刘真. 降解5-羟甲基糠醛、高产焦糖香酵母菌筛选及其混菌发酵慕萨莱思的研究[D]. 阿拉尔: 塔里木大学, 2021.
LIU Z. Screening yeast strains with degradation of 5-hydroxymethylfurfural and high production of caramel compounds and fermentation musalais by the co-inoculation of the screened strains[D].Ala’er: Tarim University, 2021.
[36] 乔通通. 慕萨莱思产关键香优良菌株的筛选与工艺优化[D]. 阿拉尔: 塔里木大学, 2022.
QIAO T T. Screening and process optimization of key fragrant and excellent strains in msalais[D].Ala’er: Tarim University, 2022.
[37] 王鹏霄. 4-羟基-2, 5-二甲基-3(2H)-呋喃酮高产菌株的选育及发酵条件优化[D]. 北京: 北京工商大学, 2010.
WANG P X. Screening of strains with high yield of HDMF and optimization of the fermentation conditions[D].Beijing: Beijing Technology and Business University, 2010.
[38] 张海林. 高产2,5-二甲基-4-羟基-3(2H)-呋喃酮酵母菌株的选育及培养环境的研究[D]. 无锡: 江南大学, 2009.
ZHANG H L. Breeding and culture environment of yeast strains with high production of 2, 5-dimethyl-4-hydroxyl-3(2H)-furanone[D].Wuxi: Jiangnan University, 2009.
[39] KOWALEWSKA J, ZELAZOWSKA H, BABUCHOWSKI A, et al. Isolation of aroma-bearing material from Lactobacillus helveticus culture and Cheese1[J]. Journal of Dairy Science, 1985, 68(9):2165-2171.
[40] PREININGER M, GROSCH W. Determination of 4-hydroxy-2, 5-dimethyl-3 (2H)-furanone (HDMF) in cultures of bacteria[J]. Zeitschrift Für Lebensmittel-Untersuchung Und Forschung, 1995, 201(1):97-98.
[41] HAYASHIDA Y, NISHIMURA K, SLAUGHTER J C. The importance of the furanones HDMF and HEMF in the flavour profile of Japanese barley miso and their production during fermentation[J]. Journal of the Science of Food and Agriculture, 1998, 78(1):88-94.
[42] KURIYAMA K, YOSHIHAMA Y. Lactic acid baterium for highly producing HDMF and its use: Japanese, 280256A [P]. 2006-10-19.
[43] 李昕. 外源D-果糖促进鲁氏酵母合成呋喃酮碳代谢的分子机制研究[D]. 大庆: 黑龙江八一农垦大学, 2020.
LI X. Carbon metabolism molecular mechanisms of D-fructose promotion on the furanone production in Zygosaccharomyces rouxii[D].Daqing: Heilongjiang Bayi Agricultural University, 2020.
[44] HAUCK T, BRÜHLMANN F, SCHWAB W. Formation of 4-hydroxy-2, 5-dimethyl-3[2H]-furanone by Zygosaccharomyces rouxii: Identification of an intermediate[J]. Applied and Environmental Microbiology, 2003, 69(7):3911-3918.
[45] ZHANG Y Y, YIN X R, XIAO Y W, et al. An ethylene response factor-myb transcription complex regulates furaneol biosynthesis by activating quinone oxidoreductase expression in strawberry[J]. Plant Physiology, 2018, 178(1):189-201.
文章导航

/