酒花与啤酒中单萜化合物的研究进展
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摘要
单萜化合物是酒花和啤酒中香气化合物的重要组成部分,具有典型的酒花香气特征,在自然界中以游离态和糖苷结合态两种形式存在。本文重点阐述了酒花中单萜化合物的生物合成途径、控制其合成的关键酶和基因以及酒花中单萜醇化合物相互转化关键酶的研究进展。此外,本文还综述了酒花与啤酒中单萜化合物的变化及其影响因素,糖苷结合态单萜化合物的结构、含量及其分析方法,并对单萜化合物在啤酒中的研究前景进行展望。
Monoterpene compounds are important components in hops and beer, responsible for the typical hop aroma attributes in beer. In nature, these compounds exist in both free and glycosidically bound forms. This review focuses on recent progress in understanding the monoterpene biosynthesis pathways, the key enzymes and genes involved in monoterpene synthesis in hops and the important enzymes responsible for the conversion of monoterpene alcohols during beer fermentation. Meanwhile, the change of monoterpenoids in hops and beer and the factors affecting it, as well as the structures and contents of glycoside-bound monoterpenoids and analytical methods for the analysis of these compounds are also reviewed in this paper. Finally, future research directions are discussed.
Monoterpene compounds are important components in hops and beer, responsible for the typical hop aroma attributes in beer. In nature, these compounds exist in both free and glycosidically bound forms. This review focuses on recent progress in understanding the monoterpene biosynthesis pathways, the key enzymes and genes involved in monoterpene synthesis in hops and the important enzymes responsible for the conversion of monoterpene alcohols during beer fermentation. Meanwhile, the change of monoterpenoids in hops and beer and the factors affecting it, as well as the structures and contents of glycoside-bound monoterpenoids and analytical methods for the analysis of these compounds are also reviewed in this paper. Finally, future research directions are discussed.
引文
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[18]XI J,ROSSI L,LIN X,et al.Overexpression of a synthetic insectplant geranyl pyrophosphate synthase gene in Camelina sativa alters plant growth and terpene biosynthesis[J].Planta,2016,244(1):215-230.DOI:10.1007/s00425-016-2504-8.
[19]KOCáBEK T,MISHRA A K,MATOU?EK J,et al.The R2R3transcription factor Hl MYB8 and its role in flavonoid biosynthesis in hop(Humulus lupulus L.)[J].Plant Science,2018,269:32-46.DOI:10.1016/j.plantsci.2018.01.004.
[20]DUDAREVA N,MARTIN D,KISH C M,et al.(E)-β-Ocimene and myrcene synthase genes of floral scent biosynthesis in snapdragon:function and expression of three terpene synthase genes of a new terpene synthase subfamily[J].Plant Cell,2003,15(5):1227-1241.DOI:10.1105/tpc.011015.
[21]KANG J,MCROBERTS J,SHI F,et al.The flavonoid biosynthetic enzyme chalcone isomerase modulates terpenoid production in glandular trichomes of tomato[J].Plant Physiology,2014,164(3):1161-1174.DOI:10.1104/pp.113.233395.
[22]ZVI M M,SHKLARMAN E,MASCI T,et al.PAP1 transcription factor enhances production of phenylpropanoid and terpenoid scent compounds in rose flowers[J].New Phytologist,2012,195(2):335-345.DOI:10.1111/j.1469-8137.2012.04161.x.
[23]GERHAUSER C,ALT A,HEISS E,et al.Cancer chemopreventive activity of xanthohumol,a natural product derived from hop[J].Molecular Cancer Therapeutics,2002,1(11):959-969.
[24]ZANOLI P,ZAVATTI M.Pharmacognostic and pharmacological profile of Humulus lupulus L.[J].Journal of Ethnopharmacology,2008,116(3):383-396.DOI:10.1016/j.jep.2008.01.011.
[25]COSTA R,RODRIGUES I,GUARD?O L,et al.Xanthohumol and8-prenylnaringenin ameliorate diabetic-related metabolic dysfunctions in mice[J].The Journal of Nutritional Biochemistry,2017,45:39-47.DOI:10.1016/j.jnutbio.2017.03.006.
[26]MATOU?EK J,KOCáBEK T,PATZAK J,et al.The“putative”role of transcription factors from Hl WRKY family in the regulation of the final steps of prenylflavonid and bitter acids biosynthesis in hop(Humulus lupulus L.)[J].Plant Molecular Biology,2016,92(3):263-277.DOI:10.1007/s11103-016-0510-7.
[27]BAN Zhaonan,QIN Hao,MITCHELL A J,et al.Noncatalytic chalcone isomerase-fold proteins in Humulus lupulus are auxiliary components in prenylated flavonoid biosynthesis[J].Proceedings of the National Academy of Sciences,2018,115(22):E5223-E5232.DOI:10.1073/pnas.1802223115.
[28]SHARPE F R,LAWS D R J.The essential oil of hops:a review[J].Journal of the Institute of Brewing,1981,87:96-107.DOI:10.1002/j.2050-0416.1981.tb03996.x.
[29]ALMAGUER C,SCH?NBERGER C,GASTL M,et al.Humulus lupulus:a story that begs to be told.a review[J].Journal of the Institute of Brewing,2014,120(4):289-314.DOI:10.1002/jib.160.
[30]VAN DE VELDE N,VERZELE M.High performance liquid chromatography of hop and beer extracts with photodiode array detection[J].Journal of the Institute of Brewing,1986,92(6):584-587.DOI:10.1002/j.2050-0416.1986.tb04457.x.
[31]THOMPSON M L,MARRIOTT R,DOWLE A,et al.Biotransformation of β-myrcene to geraniol by a strain of Rhodococcus erythropolis isolated by selective enrichment from hop plants[J].Applied Microbiology and Biotechnology,2010,85(3):721-730.DOI:10.1007/s00253-009-2182-6.
[32]STEVENS R.The chemistry of hop constituents[J].Chemical Reviews,1967,67(1):19-71.
[33]刘先章,王振洪,蒋同夫.合成香叶醇和橙花醇的研究[J].林产化学与工业,1989(4):11-19.
[34]黄宇平,刘建军,陈伟强,等.钒化合物催化芳樟醇酯化异构制取香叶醇、橙花醇[J].林产化工通讯,2005(2):28-30.
[35]尹显洪.柠檬醛还原制备橙花醇香叶醇的新方法[J].化学通报,1997(8):57-58.
[36]DENBY C M,LI R A,VU V T,et al.Industrial brewing yeast engineered for the production of primary flavor determinants in hopped beer[J].Nature Communications,2018,9(1):965-971.DOI:10.1038/s41467-018-03293-x.
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