烟草赖百当二萜代谢调控机制研究进展
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摘要
赖百当二萜是香料烟和部分雪茄烟品种叶面分泌物中的重要组成成分,其降解产物具有强烈的龙涎香香气,对改善卷烟的香气和吸味具有重要作用。本文综述了烟草赖百当二萜的合成与代谢途径及其调控机制研究进展,并对通过现代分子生物学手段培育含有赖百当二萜的特色烤烟品种及香料物质生产等领域的应用潜力进行了展望。
Labdane diterpenes are important components of leaf secretion in oriental tobacco and some cigar tobacco varieties. Labdane diterpenes and their degradation products play important roles in improving aroma and ?avor of cigarettes. Advances in the research of synthesis & metabolic pathways and regulatory mechanism of labdane diterpenes were reviewed, and prospects in terms of application potential of characteristic ?ue-cured tobacco varieties containing lypantene diterpenes in the ?eld of ?avor substances production were discussed.
Labdane diterpenes are important components of leaf secretion in oriental tobacco and some cigar tobacco varieties. Labdane diterpenes and their degradation products play important roles in improving aroma and ?avor of cigarettes. Advances in the research of synthesis & metabolic pathways and regulatory mechanism of labdane diterpenes were reviewed, and prospects in terms of application potential of characteristic ?ue-cured tobacco varieties containing lypantene diterpenes in the ?eld of ?avor substances production were discussed.
引文
[1]崔红,宋志红.类萜代谢工程研究进展及在烟草品种改良中的应用前景[J].中国烟草学报,2003,9(2):35-38,42.CUI Hong,SONG Zhihong.Recent advances in terpenoid metabolic engineering research and its prospective application in variety improvement in tobacco[J].Acta Tabacaria Sinica,2003,9(2):35-38,42.
[2]曹晓玉,杨佳玫,杨虹琦,等.烟草萜烯类化合物种类及其分析方法研究进展[J].作物研究,2013,27(3):296-301.CAO Xiaoyu,YANG Jiamei,YANG Hongqi,et al.Research progress in the species and analytical methods of terpene compounds in tobacco[J].Crop Research,2013,27(3):296-301.
[3]左天觉,朱尊权,等译.烟草的生产、生理和生物化学[M].上海:上海远东出版社,1993:422-425.ZUO Tianjue,ZHU Zunquan,et al translation.Production,physiology and biochemistry[M].Shanghai:Shanghai Far East Press,1993:422-425.
[4]D.LaytenDavis,MarkT.Nielsen.烟草:生产,化学和技术:Production,Chemistry and Technology[M].化学工业出版社,2003.
[5]Wagner G J.Elucidation of the functions of genes central to diterpene metabolism in tobacco trichomes using posttranscriptional gene silencing[J].Planta,2003,216(4):686-691.
[6]Yan N,Du Y,Liu X,et al.Chemical structures,biosynthesis,bioactivities,biocatalysis and semisynthesis of tobacco cembranoids:An overview[J].Industrial Crops&Products,2016,83:66-80.
[7]符云鹏.香料烟品质形成对生态的响应及水氮调控研究[D].河南农业大学,2012.FU Yunpeng.Response of quality formation of aromatic tobacco to ecology environment and water-nitrogen regulation[D].Henan Agricultural University,2012.
[8]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):1023-1030.
[9]Severson R,Johnson A,Jackson D.Cuticular constituents of tobacco:factors affecting their production and their role in insect and disease resistance and smoke quality[J].Recent Adv.Tobacco Sci,1985(a),11:105-174.
[10]王冬,张小全,杨铁钊,等.类西柏烷二萜代谢机理及调控研究进展[J].中国烟草学报,2014,20(3):113-118.WANG Dong,ZHANG Xiaoquan,YANG Tiezhao,et al.Research progress on metabolic mechanism of cembranoid diterpenes and its regulation[J].Acta Tabacaria Sinica,2014,20(3):113-118.
[11]聂梦云.烟草萜类代谢途径相关基因的克隆及功能分析[D].西南大学,2016.NIE Mengyun.Cloning and functional analysis of the genes related to terpenoid metabolic pathway from Nicotiana tabacum[D].Southwestern University,2016.
[12]Sallaud C,Giacalone C,T?pfer R,et al.Characterization of two genes for the biosynthesis of the labdane diterpene in tobacco(Nicotiana tabacum)glandular trichomes[J].The Plant Journal,2012,72(1):1-17.
[13]王耀,陶飞燕,周志刚,等.龙涎香香原料卷烟应用及降龙涎醚的合成研究进展[J].合成化学,2018,26(1):55-65.WANG Yao,TAO Feiyan,ZHOU Zhigang,et al.The application ambergris flavor in tobacco industry and development of synthesis of(-)-ambrox[J].Chinese Journal of synthetic Chemistry,2018,26(1):55-65.
[14]彭国岗,白晓莉.烟草二萜类化合物的降解及其在烟草香精中的应用[J].食品工业,2009,(3):52-54.PENG Guogang,BAI Xiaoli.The degradation of diterpenoids and its application in tobacco flavor[J].Chinese Journal of Food Industry,2009(3):52-54.
[15]Vontimitta V,Danehower D A,Steede T,et al.Analysis of a Nicotiana tabacum L.genomic region controlling two leaf surface chemistry traits[J].Journal of Agricultural&Food Chemistry,2010,58(1):294-300.
[16]Guo,Z H,Wagner G J.Biosynthesis of labdenediol and sclareol in cell-free extracts from trichomes of Nicotiana glutinosa.Planta,1995,197(4):627-632.
[17]Guo Z,Severson R F,Wagner G J.Biosynthesis of the diterpene cis-abienol in cell-free extracts of tobacco trichomes.Arch Biochem Biophys.1994,308(1):103-108.
[18]王国平.烟草冷杉醇合成基因功能分析及功能标记开发[D].中国农业科学院,2016.WANG Guoping.Functional analysis and marker development of cis-abienol synthesis gene in tobacco[D].Chinese Academy of Agricultural Sciences,2016.
[19]李艳华,张洪映,魏跃伟,等.典型烤烟品种腺毛形态及分泌特性比较分析[J].中国烟草学报,2017,23(2):84-91.LI Yanhua,ZHANG Hongying,WEI Yuewei,et al.Comparison analysis of trichome morphology and secretion of typical flue-cured tobacco varieties[J].Acta Tabacaria Sinica,2017,23(2):84-91.
[20]常爱霞,屈亚芳,王国平.烤烟品种大白筋599特征香气性状的物质及分子基础研究[J].中国烟草科学,2018,39(3):1-9.CHANG Aixia,QU Yafang,WANG Guoping,et al.Study on key components and molecular basis responsible for the specific aroma traits of flue-cured tobacco Da bai jin599[J].Chinese Tobacco Science,2018,39(3):1-9.
[21]Tomita H,Sato M,Kawashima N.Inheritance of labdanoid producing ability in Nicotiana tabacum[J].Agric Biol Chem,1980,44(10):2517-2518.
[22]Vontimitta V,Danehower DA,Steede T,Moon HS,Lewis RS.Analysis of a Nicotiana tabacum L.genomic region controlling two leaf surface chemistry traits[J].Journal of Agricultural&Food Chemistry,2010,58(1):294-300.
[23]Falara V,Pichersky E,Kanellis A K.A Copal-8-ol Diphosphate Synthase from the Angiosperm Cistus creticus subsp creticus is a Putative Key Enzyme for the formation of pharmacologically active,Oxygen-Containing Labdane-Type Diterpenes[J].Plant Physiology,2010,154(1):301-310.
[24]Vontimitta V,Lewis R.Mapping of quantitative trait loci affecting resistance to Phytophthora nicotianae in tobacco(Nicotiana tabacum L.)line Beinhart-1000[J].Molecular Breeding,2012,29(1):89-98.
[25]Keeling C I,Dullat H K,Yuen M,et al.Identification and functional characterization of monofunctional entcopalyl diphosphate and ent-kaurene synthases in white spruce reveal different patterns for diterpene synthase evolution for primary and secondary metabolism in gymnosperms[J].Plant Physiology,2010,152(3):1197-1208.
[26]Keeling C I,Madilao L L,Zerbe P,et al.The primary diterpene synthase products of Picea abies levopimaradiene/abietadiene synthase(PaLAS)are epimers of a thermally unstable diterpenol[J].Journal of Biology Chemistry,2011,286,21145-21153.
[27]Zerbe P,Chiang A,Yuen M,et al.Bifunctional cis-abienol synthase from Abies balsamea discovered by transcriptome sequencing and its implicationsfor diterpenoid fragrance production[J].Journal of Biological Chemistry,2012,287(15):12121-12131.
[28]Peters R J.Two rings in them all:The labdane-related diterpenoids[J].Natural Product Reports,2010,27(11):1521-1530.
[29]Cui H,Zhang S T,Yang H J,et al.Gene expression profile analysis of tobacco leaf trichomes[J].BMC Plant Biology,2011,11(1):76.
[30]Wang E M,Gan S S,Wagner G J.Isolation and characterization of the CYP71D16 trichome-specific promoter from Nicotiana tabacum L[J].Joural of Experimental Botany,2002,53(376):1891-1897.
[31]Severson R F,Eckel R W,Jackson D M,et al.Aphicidal activity and cuticular components from Nicotiana tabacum[J].American Chemical Society,1994,551:172-179.
[32]Johnson A W,Severson R F.Leaf surface chemistry of tobacco budworm resistant tobacco[J].Journal of Agricultural Entomology,1984,1(1):23-32.
[33]Jackson D M,Danehower D A.Integrated case study:Nicotiana leaf-surface components and their effects on insect pests and diseases[J].BIOS Science,1996,231-254.
[34]Kennedy B S,Nielsen M T,Severson R F,et al.Leaf surface chemicals from Nicotiana affecting germination of PeronosporaTabacina(Adam)Sporangia[J].Journal of Chemical Ecology,1992,18(9):1467-1479.
[35]Seo S,Gomi K,Kaku H,et al.Identification of natural diterpenes that inhibit bacterial wilt disease in tobacco,tomato and arabidopsis[J].Plant Cell Physiol.2012,53(8):1432-1444.
[36]Seo S,Seto H,Koshino H,et al.A Diterpene as an Endogenous Signal for the Activation of Defense Responses to Infection with Tobacco mosaic virus and wounding in Tobacco[J].Plant Cell,2003,15(4):863-873.
[37]William T S,Justin M M,David P E,et al.The Tobacco trichome exudate Z-abienol and Its Relationship with Plant Resistance to Phytophthora nicotianae[J].Plant Disease,2017,101(7):1214-1221.
[38]周冀衡,朱小平,王彦亭,等.烟草生理与生物化学[M].合肥:中国科学技术大学出版社,1996:478-480.ZHOU Jiheng,ZHU Xiaoping,WANG Yanting,et al.Tobacco physiology and biochemistry[M].Hefei:University of Science and Technology of China Press,1996:478-480.
[39]卢建媚,车宗伶,马广皓.赖百当净油和浸膏挥发性成分的GC-MS分析研究[J].香料香精化妆品,2015(1):33-38.LU Jianmei,CHE Zongling,MA Guanghao.Analysis of Volatile Components in Labdanum Absolutes and Concretes by GC-MS[J].Flavor Fragance Cosmetics,2015(1):33-38.
[40]胡永华,徐迎波,王程辉,等.龙涎香类化合物中基团的空间可接近性与其香气的关系[J].烟草科技,2010,278(9):25-29.HU Yonghua,XU Yingbo,WANG Chenghui,et al.Relationship between steric accessibilities of functional groups in ambergrisoid compounds and their Aroma[J].Tobacco Science&Technology,2010,278(9):25-29.
[41]Christenson P A.Alkyl sclareol diol carbonates in tobacco:US,US5671756[P].1997.
[42]杨华武,黎艳玲,周宇,等.用于制备降龙涎醚或向卷烟烟气释放降龙涎醚的草酸酯及应用:CN 11583711A[P].2005.YANG Huawu,LI Yanling,ZHOU Yu,et al.Oxalic ester of liningup(-)-ambroxide or releasing(-)-ambroxide to cigarette smoke:CN 11583711A[P].2005.
[43]Moulines J,Lamidey A M,Breuil V D.A practical synthesis of Ambrox from sclareol using no mentallic oxidant[J].Synthetic Communication,2001,31(5):749-758.
[44]王文军,陈莎,戴乾圜.龙涎香的组成及降龙涎醚的合成研究进展[J].有机化学,2001,21(3):167-172.WANG Wenjun,CHEN Sha,DAI Qianhuan.The composition of ambergris and development of the synthesis of(-)-ambrox[J].Chinese Journal of Organic Chemistry,2001,21(3):167-172.
[2]曹晓玉,杨佳玫,杨虹琦,等.烟草萜烯类化合物种类及其分析方法研究进展[J].作物研究,2013,27(3):296-301.CAO Xiaoyu,YANG Jiamei,YANG Hongqi,et al.Research progress in the species and analytical methods of terpene compounds in tobacco[J].Crop Research,2013,27(3):296-301.
[3]左天觉,朱尊权,等译.烟草的生产、生理和生物化学[M].上海:上海远东出版社,1993:422-425.ZUO Tianjue,ZHU Zunquan,et al translation.Production,physiology and biochemistry[M].Shanghai:Shanghai Far East Press,1993:422-425.
[4]D.LaytenDavis,MarkT.Nielsen.烟草:生产,化学和技术:Production,Chemistry and Technology[M].化学工业出版社,2003.
[5]Wagner G J.Elucidation of the functions of genes central to diterpene metabolism in tobacco trichomes using posttranscriptional gene silencing[J].Planta,2003,216(4):686-691.
[6]Yan N,Du Y,Liu X,et al.Chemical structures,biosynthesis,bioactivities,biocatalysis and semisynthesis of tobacco cembranoids:An overview[J].Industrial Crops&Products,2016,83:66-80.
[7]符云鹏.香料烟品质形成对生态的响应及水氮调控研究[D].河南农业大学,2012.FU Yunpeng.Response of quality formation of aromatic tobacco to ecology environment and water-nitrogen regulation[D].Henan Agricultural University,2012.
[8]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):1023-1030.
[9]Severson R,Johnson A,Jackson D.Cuticular constituents of tobacco:factors affecting their production and their role in insect and disease resistance and smoke quality[J].Recent Adv.Tobacco Sci,1985(a),11:105-174.
[10]王冬,张小全,杨铁钊,等.类西柏烷二萜代谢机理及调控研究进展[J].中国烟草学报,2014,20(3):113-118.WANG Dong,ZHANG Xiaoquan,YANG Tiezhao,et al.Research progress on metabolic mechanism of cembranoid diterpenes and its regulation[J].Acta Tabacaria Sinica,2014,20(3):113-118.
[11]聂梦云.烟草萜类代谢途径相关基因的克隆及功能分析[D].西南大学,2016.NIE Mengyun.Cloning and functional analysis of the genes related to terpenoid metabolic pathway from Nicotiana tabacum[D].Southwestern University,2016.
[12]Sallaud C,Giacalone C,T?pfer R,et al.Characterization of two genes for the biosynthesis of the labdane diterpene in tobacco(Nicotiana tabacum)glandular trichomes[J].The Plant Journal,2012,72(1):1-17.
[13]王耀,陶飞燕,周志刚,等.龙涎香香原料卷烟应用及降龙涎醚的合成研究进展[J].合成化学,2018,26(1):55-65.WANG Yao,TAO Feiyan,ZHOU Zhigang,et al.The application ambergris flavor in tobacco industry and development of synthesis of(-)-ambrox[J].Chinese Journal of synthetic Chemistry,2018,26(1):55-65.
[14]彭国岗,白晓莉.烟草二萜类化合物的降解及其在烟草香精中的应用[J].食品工业,2009,(3):52-54.PENG Guogang,BAI Xiaoli.The degradation of diterpenoids and its application in tobacco flavor[J].Chinese Journal of Food Industry,2009(3):52-54.
[15]Vontimitta V,Danehower D A,Steede T,et al.Analysis of a Nicotiana tabacum L.genomic region controlling two leaf surface chemistry traits[J].Journal of Agricultural&Food Chemistry,2010,58(1):294-300.
[16]Guo,Z H,Wagner G J.Biosynthesis of labdenediol and sclareol in cell-free extracts from trichomes of Nicotiana glutinosa.Planta,1995,197(4):627-632.
[17]Guo Z,Severson R F,Wagner G J.Biosynthesis of the diterpene cis-abienol in cell-free extracts of tobacco trichomes.Arch Biochem Biophys.1994,308(1):103-108.
[18]王国平.烟草冷杉醇合成基因功能分析及功能标记开发[D].中国农业科学院,2016.WANG Guoping.Functional analysis and marker development of cis-abienol synthesis gene in tobacco[D].Chinese Academy of Agricultural Sciences,2016.
[19]李艳华,张洪映,魏跃伟,等.典型烤烟品种腺毛形态及分泌特性比较分析[J].中国烟草学报,2017,23(2):84-91.LI Yanhua,ZHANG Hongying,WEI Yuewei,et al.Comparison analysis of trichome morphology and secretion of typical flue-cured tobacco varieties[J].Acta Tabacaria Sinica,2017,23(2):84-91.
[20]常爱霞,屈亚芳,王国平.烤烟品种大白筋599特征香气性状的物质及分子基础研究[J].中国烟草科学,2018,39(3):1-9.CHANG Aixia,QU Yafang,WANG Guoping,et al.Study on key components and molecular basis responsible for the specific aroma traits of flue-cured tobacco Da bai jin599[J].Chinese Tobacco Science,2018,39(3):1-9.
[21]Tomita H,Sato M,Kawashima N.Inheritance of labdanoid producing ability in Nicotiana tabacum[J].Agric Biol Chem,1980,44(10):2517-2518.
[22]Vontimitta V,Danehower DA,Steede T,Moon HS,Lewis RS.Analysis of a Nicotiana tabacum L.genomic region controlling two leaf surface chemistry traits[J].Journal of Agricultural&Food Chemistry,2010,58(1):294-300.
[23]Falara V,Pichersky E,Kanellis A K.A Copal-8-ol Diphosphate Synthase from the Angiosperm Cistus creticus subsp creticus is a Putative Key Enzyme for the formation of pharmacologically active,Oxygen-Containing Labdane-Type Diterpenes[J].Plant Physiology,2010,154(1):301-310.
[24]Vontimitta V,Lewis R.Mapping of quantitative trait loci affecting resistance to Phytophthora nicotianae in tobacco(Nicotiana tabacum L.)line Beinhart-1000[J].Molecular Breeding,2012,29(1):89-98.
[25]Keeling C I,Dullat H K,Yuen M,et al.Identification and functional characterization of monofunctional entcopalyl diphosphate and ent-kaurene synthases in white spruce reveal different patterns for diterpene synthase evolution for primary and secondary metabolism in gymnosperms[J].Plant Physiology,2010,152(3):1197-1208.
[26]Keeling C I,Madilao L L,Zerbe P,et al.The primary diterpene synthase products of Picea abies levopimaradiene/abietadiene synthase(PaLAS)are epimers of a thermally unstable diterpenol[J].Journal of Biology Chemistry,2011,286,21145-21153.
[27]Zerbe P,Chiang A,Yuen M,et al.Bifunctional cis-abienol synthase from Abies balsamea discovered by transcriptome sequencing and its implicationsfor diterpenoid fragrance production[J].Journal of Biological Chemistry,2012,287(15):12121-12131.
[28]Peters R J.Two rings in them all:The labdane-related diterpenoids[J].Natural Product Reports,2010,27(11):1521-1530.
[29]Cui H,Zhang S T,Yang H J,et al.Gene expression profile analysis of tobacco leaf trichomes[J].BMC Plant Biology,2011,11(1):76.
[30]Wang E M,Gan S S,Wagner G J.Isolation and characterization of the CYP71D16 trichome-specific promoter from Nicotiana tabacum L[J].Joural of Experimental Botany,2002,53(376):1891-1897.
[31]Severson R F,Eckel R W,Jackson D M,et al.Aphicidal activity and cuticular components from Nicotiana tabacum[J].American Chemical Society,1994,551:172-179.
[32]Johnson A W,Severson R F.Leaf surface chemistry of tobacco budworm resistant tobacco[J].Journal of Agricultural Entomology,1984,1(1):23-32.
[33]Jackson D M,Danehower D A.Integrated case study:Nicotiana leaf-surface components and their effects on insect pests and diseases[J].BIOS Science,1996,231-254.
[34]Kennedy B S,Nielsen M T,Severson R F,et al.Leaf surface chemicals from Nicotiana affecting germination of PeronosporaTabacina(Adam)Sporangia[J].Journal of Chemical Ecology,1992,18(9):1467-1479.
[35]Seo S,Gomi K,Kaku H,et al.Identification of natural diterpenes that inhibit bacterial wilt disease in tobacco,tomato and arabidopsis[J].Plant Cell Physiol.2012,53(8):1432-1444.
[36]Seo S,Seto H,Koshino H,et al.A Diterpene as an Endogenous Signal for the Activation of Defense Responses to Infection with Tobacco mosaic virus and wounding in Tobacco[J].Plant Cell,2003,15(4):863-873.
[37]William T S,Justin M M,David P E,et al.The Tobacco trichome exudate Z-abienol and Its Relationship with Plant Resistance to Phytophthora nicotianae[J].Plant Disease,2017,101(7):1214-1221.
[38]周冀衡,朱小平,王彦亭,等.烟草生理与生物化学[M].合肥:中国科学技术大学出版社,1996:478-480.ZHOU Jiheng,ZHU Xiaoping,WANG Yanting,et al.Tobacco physiology and biochemistry[M].Hefei:University of Science and Technology of China Press,1996:478-480.
[39]卢建媚,车宗伶,马广皓.赖百当净油和浸膏挥发性成分的GC-MS分析研究[J].香料香精化妆品,2015(1):33-38.LU Jianmei,CHE Zongling,MA Guanghao.Analysis of Volatile Components in Labdanum Absolutes and Concretes by GC-MS[J].Flavor Fragance Cosmetics,2015(1):33-38.
[40]胡永华,徐迎波,王程辉,等.龙涎香类化合物中基团的空间可接近性与其香气的关系[J].烟草科技,2010,278(9):25-29.HU Yonghua,XU Yingbo,WANG Chenghui,et al.Relationship between steric accessibilities of functional groups in ambergrisoid compounds and their Aroma[J].Tobacco Science&Technology,2010,278(9):25-29.
[41]Christenson P A.Alkyl sclareol diol carbonates in tobacco:US,US5671756[P].1997.
[42]杨华武,黎艳玲,周宇,等.用于制备降龙涎醚或向卷烟烟气释放降龙涎醚的草酸酯及应用:CN 11583711A[P].2005.YANG Huawu,LI Yanling,ZHOU Yu,et al.Oxalic ester of liningup(-)-ambroxide or releasing(-)-ambroxide to cigarette smoke:CN 11583711A[P].2005.
[43]Moulines J,Lamidey A M,Breuil V D.A practical synthesis of Ambrox from sclareol using no mentallic oxidant[J].Synthetic Communication,2001,31(5):749-758.
[44]王文军,陈莎,戴乾圜.龙涎香的组成及降龙涎醚的合成研究进展[J].有机化学,2001,21(3):167-172.WANG Wenjun,CHEN Sha,DAI Qianhuan.The composition of ambergris and development of the synthesis of(-)-ambrox[J].Chinese Journal of Organic Chemistry,2001,21(3):167-172.