| 374 | 5 | 465 |
| 下载次数 | 被引频次 | 阅读次数 |
α,β-4,8,13-西柏三烯-1,3-二醇作为重要的烟草香味前体物质,对烟草的香味调控具有重要作用,为了提升烟草品质,各国学者对西柏三烯二醇提纯、定量定性分析和降解机理进行深入的研究。作者详细介绍了西柏三烯二醇的提纯技术研究进展,包括蒸馏法和萃取法;并对西柏三烯二醇定量定性分析常用的高效液相色谱-质谱和气相色谱-质谱方法进行了简述;最后分析了西柏三烯二醇降解机理的研究,根据降解过程差异对比了3种途径的降解机理。在现有研究的基础上,最终提出了在提纯、分析及机理研究等方面的几个优化方法和方向,对更好调控烟草香味具有重要的指导意义。
Abstract：α, β-4,8,13-cembratriene-1,3-diols, as an important tobacco flavor precursor, plays a crucial role in tobacco flavor regulation. The purification, quantitative and qualitative analysis and degradation of the flavor precursor were well studied for improving the quality of tobacco. The purification technology of cembratriene-diols was reviewed in detail, including distillation and extraction process. The quantitative and qualitative analysis by the high performance liquid chromatography-mass spectrometry(HPLC-MS) and the gas chromatography-mass spectrometry(GC-MS) were briefly introduced. Finally, the degradation mechanism of three pathway of cembratriene-diols was described and compared. Several development directions in purification, analysis and mechanism study were proposed.
[1]刘翠翠.烟草西柏三烯二醇检测方法及其积累动态、分布研究[D].青岛:中国农业科学院,2016.LIU C C.Establishment and application of a detection method for investigating the accumulation,distribution of cembratrien-diols in tobacco[D].Qingdao:Chinese Academy of Agricultural Sciences,2016.
[2]王冬.烟草西柏三烯二醇积累的遗传及生态响应研究[D].郑州:河南农业大学,2014.WANG D.Research of genetic basis and ecological response of cembratrien-diol synthesis in tobacco[D].Zhengzhou:Henan Agricultural University,2014.
[3]付秋娟,刘艳华,杜咏梅,等.我国烟草资源西柏三烯二醇含量分析[J].中国烟草学报,2019,25(5):10-14.FU Q J,LIU Y H,DU Y M,et al.Analysis of cembratriendiol content in tobaccos growing in China[J].Acta Tabacaria Sinica,2019,25(5):10-14.
[4]JACKSON D M,SEVERSON R F,JOHNSON A W,et al.Ovipositional response of tobacco budworm moths(lepidoptera:noctuidae) to cuticular chemical isolates from green tobacco leaves[J].Environmental Entomology,1984,13(4):1023-1030.
[5]YAN N,DU Y M,LIU X M,et al.A review on bioactivities of tobacco cembranoid diterpenes[J/OL].Biomolecules,2019,9(1)[2021-03-30].http://doi.org/10.3390/biom 9010030.
[6]EBRAHIM H Y,MOHYELDIN M M,HAILAT M M,et al.(1S,2E,4S,7E,11E)-2,7,11-cembratriene-4,6-diol semisynthetic analogs as novel c-met inhibitors for the control of c-met-dependent breast malignancies[J].Bioorganic&Medicinal Chemistry,2016,24(22):5748-5761.
[7]SAITO Y,TSUJINO Y,KANEKO H,et al.Inhibitory effects of cembratriene-4,6-diol derivatives on the induction of Epstein Barr virus early antigen by 12-o-tetradecanoylphorbol-13-acetate[J].Agricultural and Biological Chemistry,1987,51(3):941-943.
[8]YUAN X L,MAO X X,DU Y M,et al.Anti-tumor activity of cembranoid-type diterpenes isolated from nicotiana tabacum L[J/OL].Biomolecules,2019,9(2)[2021-03-30].http://doi.org/10.3390/biom 9020045.
[9]张献忠.废次烟末中烟草香味物质提取、应用及生物活性[D].杭州:浙江大学,2013.ZHANG X Z.Extraction of tobacco flavor compounds from discarded tobacco leaves and their application in cigarettes and in vitro bioactivities[D].Hangzhou:Zhejiang University,2013.
[10]钱晓波.烤烟中西柏三烯醇、糖苷类物质的检测及其与烟叶油润性的关系[D].合肥:中国科学技术大学,2014.QIAN X B.Study on quantification of cembranoids and glycosides in tobacco and their impacts on oil wetability property of tobacco leaves[D].Hefei:University of Science and Technology of China,2014.
[11]付秋娟,杜咏梅,刘新民,等.超高效液相色谱法测定烟草西柏三烯二醇[J].中国烟草科学,2017,38(3):67-73.FU Q J,DU Y M,LIU X M,et al.Determination of cembratriene-diols in tobacco by ultra performance liquid chromatography[J].Chinese Tobacco Science,2017,38(3):67-73.
[12]高旭,陈鹏,洪林军,等.分子蒸馏技术在烟用香料提取分离中的应用[J].化学工程师,2009,23(10):54-56.GAO X,CHEN P,HONG L J,et al.Application of molecular distillation on separation of flavor material for tobacco[J].Chemical Engineer,2009,23(10):54-56.
[13]危彬.烟草萃取物的分离分类及其香味成分研究[D].合肥:中国科学技术大学,2016.WEI B.Separation of flavor components in tobacco extracts[D].Hefei:University of Science and Technology of China,2016.
[14]李桂花.同时蒸馏萃取法及其在烟草分析中的应用研究[D].杭州:浙江大学,2007.LI G H.Simultaneous distillation extraction and its applications in analysis of tobacco[D].Hangzhou:Zhejiang University,2007.
[15]LIKENS S T,NIKERSON G B.Detection of certain hop oil constituents in brewing products[J].Journal of the American Society of Brewing Chemists,1964,5(1):5-13.
[16]李炎强,洗可法.同时蒸馏萃取法与水蒸气蒸馏法分离分析烟草挥发性、半挥发性中性成分的比较[J].烟草科技,2000,2:18-21.LI Y Q,XI K F.Comparison of SDE and WSD in analyzing the volatile,semi-volatile neutral components in tobacco[J].Tobacco Science&Technology,2000,2:18-21.
[17]刘清梁.烟叶中重要化合物测定方法的研究[D].南京:南京理工大学,2009.LIU Q L.Research on determination methods of important compounds in tobacco leaves[D].Nanjing:Nanjing University of Science and Technology,2009.
[18]李小福,殷全玉.同时蒸馏萃取和减压蒸馏萃取方法提取烟叶香气成分的比较[J].中国科技论文在线,2008,9:672-676.LI X F,YIN Q Y.The comparison of tobacco aroma components extracted by the two ways of simultaneous distillation abstraction[J].Sciencepaper Online,2008,9:672-676.
[19]宋红平,梅涌,李玲,等.分子蒸馏技术分离薄片浓缩液中的致香成分[J].云南民族大学学报(自然科学版),2013,22(1):22-26.SONG H P,MEI Y,LI L,et al.Application of molecular distillation on separation of concentrated solution for reconstituted tobacco produced by paper-making process[J].Journal of Yunnan University of Nationalities(Natural Sciences Edition),2013,22(1):22-26.
[20]何康.烟草西柏三烯二醇超临界CO2提取工艺及其生物活性研究[D].青岛:中国农业科学院,2017.HE K.Study on the supercritical fluid extraction and biological activity of cembratrien-diols in tobacco[D].Qingdao:Chinese Academy of Agricultural Sciences,2017.
[21]熊国玺,朱巍,喻世涛.超临界CO2萃取与分子蒸馏联用技术在烟草香味成分提取中的应用[J].湖北农业科学,2010,49(7):1690-1693.XIONG G X,ZHU W,YU S T.Application of extracting the aroma constituents in tobacco with supercritical CO2 fluid extraction and molecular distillation technology[J].Hubei Agricultural Sciences,2010,49(7):1690-1693.
[22]国家烟草专卖局.烟草及烟草制品西柏烷二萜醇的测定气相色谱-质谱联用法:YC/T 470-2013[S].北京:中国标准出版社,2013.State Tobacco Monopoly Administration.Tobacco and tobacco products-determination of cembrenediol-GC/MS method:YC/T470-2013[S].Beijing:Standards Press of China,2013.
[23]张忠锋,杜咏梅,颜培真,等.烟草花序中提取西柏烷二萜的方法:CN,105001052A[P].2015-10-28.ZHANG Z F,DU Y M,YAN P Z,et al.Method for extracting cembrane diterpene from tobacco inflorescence:CN,105001052A[P].2015-10-28.
[24]储国海,陆明华,舒明,等.烟草致香成分超声溶剂萃取-气相色谱-质谱法研究[J].香料香精化妆品,2006(1):17-21.CHU G H,LU M H,SHU M,et al.Analysis of flavor components in tobacco by ultrasonic solvent extraction-gas chromatography-mass spectrometry[J].Flavour Fragrance Cosmetics,2006(1):17-21.
[25]QIAN X B,YE J P,CHEN X M,et al.Analysis of cembranoids in flue-cured tobacco by accelerated solvent extraction and gas chromatography-mass spectrometry-selected ion monitoring[J].Journal of the Chinese Chemical Society,2014,61:1133-1140.
[26]何峰.西柏三烯-4,6-二醇的分离纯化及热裂解和烟草中HPLC分析方法研究[D].郑州:郑州轻工业学院,2015.HE F.Isolation&purification and pyrolysis analysis of cembratriene-4,6-diols and their determination in tobacco with HPLC[D].Zhengzhou:Zhengzhou University of Light Industry,2015.
[27]贾春晓,何峰,马宇平,等.西柏烯类化合物研究进展[J].轻工学报,2016,31(1):46-54.JIA C X,HE F,MA Y P,et al.Research advance in cembranoid compounds[J].Journal of Light Industry,2016,31(1):46-54.
[28]ROBERTS D L,ROWLAND R L.Macrocyclic diterpenes.α-andβ-4,8,13-duvatriene-1,3-diols from tobacco[J].The Journal of Organic Chemistry,1962,27(11):3989-3995.
[29]SPRINGER J P,CLARDY J,COX R H,et al.The structure of a new type of plant growth inhibitor extracted from immature tobacco leaves[J].Tetrahedron Letters,1975,16(32):2737-2740.
[30]AASEN A J,JUNKER N,ENZELL C R,et al.Tobacco chemistry 36.Absolute configuration of tobacco thunberganoids[J].Tetrahedron Letters,1975,16(30):2607-2610.
[31]SEVERSON R F,ARRENDALE R F,CHORTYK O T,et al.Quantitation of the major cuticular components from green leaf of different tobacco types[J].Journal of Agricultural&Food Chemistry,1984,32(3):566-570.
[32]LOUGHRIN J H,HAMILTON-KEMP T R,ANDERSEN R A,et al.Headspace compounds from flowers of nicotiana tabacum and related species[J].Journal of Agricultural and Food Chemistry,1990,38(2):455-460.
[33]WEI G,WU N Y,SUN W L.Development and validation of a gas chromatography/mass spectrometry method for the determination ofα-and?-2,7,11-cembratriene-4,6-diols in tobacco[J].World Journal of Engineering,2016,13(4):341-347.
[34]杨军慧,董杏梅.《烤烟》国家标准在执行中存在的问题与对策[J].安徽农业科学,2013,41(17):7704-7705,7721.YANG J H,DONG X M.The problems and countermeasures in the implementation of the national standard of"Flue-cured Tobacco"[J].Journal of Anhui Agricultural Sciences,2013,41(17):7704-7705,7721.
[35]TRANCHIDA P Q.Comprehensive two-dimensional gas chromatography:A perspective on processes of modulation[J].Journal of Chromatography,2018,1536:2-5.
[36]MAZUR D M,ZENKEVICH I G,ARTAEV V B,et al.Regression algorithm for calculating second-dimension retention indices in comprehensive two-dimensional gas chromatography[J].Journal of Chromatography A,2018,1569:178-185.
[37]CHEN M,DONG H Z,SHEN S H,et al.Quantitative analysis of cembranoids in tobacco leaf by using heart-cutting two-dimensional liquid chromatography[J].Separation Science Plus,2019,2:112-119.
[38]黄志,毕艳玖,沙云菲,等.在线液相色谱-气相色谱/质谱联用快速分析烟叶中的西柏三烯二醇[J].上海大学学报(自然科学版),2020,26(2):227-233.HUANG Z,BI Y J,SHA Y F,et al.Analysis of cembratriene-diols in tobacco by LC-GC/MS[J].Journal of Shanghai University(Natural Science Edition),2020,26(2):227-233.
[39]WAHLBERG I,ENZELL C R.Tobacco cembranoids[J].Btrage zur Tabakforschung International/Contributions to Tobacco Research,1984,12(3):93-104.
[40]ARNDT R,BERG J E,WAHLBERG I,et al.Tobacco chemistry.71.Structure determination and biomimetic studies of five new tobacco cembranoids[J].Acta Chemica Scandinavica,1990,44:814-825.
[41]ROWLAND R L,RODGMAN A,SCHUMACHER J N,et al.Macrocyclic diterpene hydroxy ethers from tobacco and cigarette smoke[J].Journal of Organic Chemistry,1964,29(1):16-21.
[42]WAHLBERG I,VOGT C,WALLIN I,et al.Tobacco chemistry.57.Two new labdanic compounds from tobacco[J].Acta Chemica Scandinavica,1982,B36:573-576.
[43]WAHLBERG I,BEHR D,MARIE A E,et al.Tobacco Chemistry.56.The stereochemistries of the tobacco diterpenoids:the(1S,2E,4S,6E,8S,11E)-and (1S,2E,4R,6E,8S,11E)-2,6,11-cembratriene-4,8-diols.acid-induced transformations of cembratrienediols[J].Acta Chemica Scandinavica,1982,B36:443-449.
[44]BEHR D,WAHLBERG I,AASEN A J,et al.Tobacco chemistry.44.(1S,2E,4R,6E,8R,11S,12R)-and (1S,2E,4S,6E,8R,11S,12R)-8,11-epoxy-2,6-thunbergadiene-4,12-diol.Two new diterpenoids of greek tobacco[J].Acta Chemica Scandinavica,1978,32(3):221-227.
[45]王瑞新.烟草化学[M].北京:中国农业出版社,2003.WANG R X.Chemistry of tobacco[M].Beijing:China Agricultural Press,2003.
[46]RALDUGIN V A,REZVUKHIN A I,KOROTKIKH L Y,et al.Oxidative transformations of cembrane diterpenoids.II.Cembra-2,7,11-triene-4,5-diols[J].Chemistry of Natural Compounds,1977,13(1):46-49.
[47]RALDUGIN V A,KOROTKIKH L Y,REZVUKHIN A I,et al.Oxidative transformations of cembrane diterpenoids III.Epoxycembrenes[J].Chemistry of Natural Compounds,1977,13(4):439-443.
[48]ARNARP J,CHU W L A,ENZELL C R,et al.ChemInForm abstract:tobacco chemistry.Part 76.Biotransformations of tobacco isoprenoids using plant cell cultures of tripterygium wilfordii[J].Acta Chemica Srnndinavica,1993,47:683-688.
[49]RALDUGIN V A,FEDOROV V K,PENTEGOVA V A.Oxidative transformations of cembrane diterpenoids I.Oxidation of cembrene with chromium trioxide[J].Chemistry of Natural Compounds,1976,12(3):278-282.
[50]ARNARP J,CHU W L A,ENZELL C R,et al.Cheminform abstract:tobacco chemistry.Part 77.Biotransformations of a major tobacco cembratrienediol using plant cell cultures of nicotiana sylvestris[J].Acta Chemica Srnndinavica,1993,47:689-694.
[51]DEMOLE E,BERTHET D.A chemical study of burley tobacco flavour(nicotiana tabacum l.).I.Volatile to medium-volatile constituents(b.p.≤84°/0.001 torr[J].Helvetica Chimica Acta,1972,55(6):1866-1882.
[52]KNOX S T,PARKINSON S,STONE R,et al.Benchtop flow-NMR for rapid online monitoring of raft and free radical polymerisation in batch and continuous reactors[J].Polymer Chemistry,2019,10:4774-4778.
[53]FRIEBEL A,HARBOU E V,MüNNEMANN K,et al.Online process monitoring of a batch distillation by medium field NMRspectroscopy[J].Chemical Engineering Science,2020,219(6):115561.
[54]LIN J,CHEN Y,ZHOU Y L,et al.More active IR subnanometer clusters than single-atoms for catalytic oxidation of CO at low temperature[J].AIChE Journal,2017,63(9):4003-4012.
[55]SPEZZATI G,BENAVIDEZ A D,DELARIVA A T,et al.CO oxidation by Pd supported on CeO2(100) and CeO2(111) facets[J].Applied Catalysis B:Environmental,2019,243:36-46.
基本信息:
中图分类号:TS411
引用信息:
[1]杨元鑫,阮建成,边腾飞,等.西柏三烯二醇分析、纯化及降解机理研究进展[J],2022,36(01):1-8.
基金信息:
国家自然科学基金(21878265)