植物性食品原料中单萜类化合物形成机理及生物活性综述
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摘要
单萜类化合物具有独特的香味和生物活性,其广泛应用于食品、化妆品、医药等众多领域,但是目前天然存在的含量较少,因此,单萜类化合物的形成机理成为急需解决的问题。该文对植物性食品原料中单萜类化合物的分类、香气特征、形成机理及其生物活性进行了综述。对其应用前景进行了展望,以期为单萜类化合物的应用和生产提供理论基础。
Monoterpenes compounds have unique flavor and physiological activity, which have been widely applied in many fields such as food,cosmetics, pharmaceuticals, and so on, but the monoterpenes compounds content of natural presence was less. Therefore, the formation mechanism of monoterpenes compounds become an urgent problem. The classification, aroma characteristics, formation mechanism and physiological activity of monoterpenes compounds in edible plants were summarized, and its application prospect was prospected, in order to provide theoretical basis for application and production of monoterpenes compounds.
Monoterpenes compounds have unique flavor and physiological activity, which have been widely applied in many fields such as food,cosmetics, pharmaceuticals, and so on, but the monoterpenes compounds content of natural presence was less. Therefore, the formation mechanism of monoterpenes compounds become an urgent problem. The classification, aroma characteristics, formation mechanism and physiological activity of monoterpenes compounds in edible plants were summarized, and its application prospect was prospected, in order to provide theoretical basis for application and production of monoterpenes compounds.
引文
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[23]TELCI I,DEMIRTAS I,BAYRAM E,et al.Environmental variation on aroma components of pulegone/piperitone rich spearmint(Mentha spicata L.)[J].Ind Crop Prod,2010,32(3):588-592.
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[27]VOIRIN S G,BAUMES R L,BITTEUR S M,et al.Novel monoterpene disaccharide glycosides of Vitis vinifera grapes[J].J Agr Food Chem,1990,38(6):1373-1378.
[28]姜洁.单萜烯在酸性条件下的重排机理的探究[D].广州:华南理工大学,2013.
[29]LARSEN T O,FRISVAD J C.A simple method for collection of volatile metabolites from fungi based on diffusive sampling from petri dishes[J].J Microbioll Method,1994,19(4):297-305.
[30]CARRAU F M,MEDINA K,BOIDO E,et al.De novo synthesis of monoterpenes by Saccharomyces cerevisiae wine yeasts[J].FEMS Microbiol Lett,2005,243(1):107-115.
[31]张艳,卢文玉.酿酒酵母细胞表达异源萜类化合物的研究进展[J].化工进展,2014(5):1265-1270.
[32]吴勇.萜烯类化合物与茶叶香气[J].化学工程与装备,2009(11):123-113.
[33]KALEMBA D,KUNICKA A.Antibacterial and antifungal properties of essential oils[J].Curr Med Chem,2003,10(10):813-29.
[34]王雪梅,谌徽,李雪姣,等.天然活性单萜—柠檬烯的抑菌性能研究[J].吉林农业大学学报,2010,32(1):24-28.
[35]KALP G I,NE E K,MINE K,et al.Antimicrobial screening of Mentha piperita essential oils[J].J Agr Food Chem,2002,50(14):3943-3946.
[36]张婷.芳樟醇通过激活GADD45α/JNK信号通路选择性诱导淋巴细胞白血病细胞凋亡的研究[D].杭州:浙江大学,2007.
[37]DEGENHARDT J,K魻LLNER T G,GERSHENZON J.Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants[J].Phytochemistry,2009,70(15-16):1621-1637.
[38]CROTEAU R,KARP F.Biosynthesis of monoterpenes:Hydrolysis of bornyl pyrophosphate,an essential step in camphor biosynthesis,and hydrolysis of geranyl pyrophosphate,the acyclic precursor of camphor,by enzymes from sage[J].Brit Med J,1990,301(6753):651-653.
[2]兰颐,王景雁,刘艳,等.萜烯类经皮促透剂对皮肤活性表皮层的影响及其机制研究[J].中国中药杂志,2015,40(4):643-648.
[3]郑向平,张葆春,赵玉平,等.白兰地挥发性芳香族化合物的初步探究[J].中国酿造,2014,33(9):1-5.
[4]师彦平.单萜和倍半萜化学[M].北京:化学工业出版社,2008:44-54.
[5]DAMBOLENA J S,LOPEZ A G,CANEPA M C,et al.Inhibitory effect of cyclic terpenes(limonene,menthol,menthone and thymol)on Fusarium verticillioides MRC 826 growth and fumonisin B1 biosynthesis[J].Toxicon,2008,51(1):37-44.
[6]阎正,冯天铸.气相色谱法测定冠心膏中樟脑、薄荷脑、异龙脑、龙脑的含量[J].色谱,1998,16(5):411-413.
[7]范文来,徐岩.酒类风味化学[M].北京:中国轻工业出版社,2014:279-312.
[8]STEINGASS C B,CARLE R,SCHMARR H G.Ripening-dependent metabolic changes in the volatiles of pineapple(Ananas comosus(L.)Merr.)fruit:I.Characterization of pineapple aroma compounds by comprehensive two-dimensional gas chromatography-mass spectrometry[J].Anal Bioanal Chem,2015,407(9):1391-2608.
[9]范文来,徐岩.白酒中重要的功能化合物萜烯综述[J].酿酒,2013,40(6):11-16.
[10]RUIZ-GARCIA L,HELLIN P,FLORES P,et al.Prediction of Muscat aroma in table grape by analysis of rose oxide[J].Food Chem,2014,154(2):151-157.
[11]CROTEAU R,MIYAZAKI JH,WHEELER CJ.Monoterpene biosynthesis:mechanistic evaluation of the geranyl pyrophosphate:(-)-endofenchol cyclase from fenne l(Foeniculum vulgare)[J].Archs Biochem Biophys,1989,269(2):507-516.
[12]BA S,ER K H C,DEMIRCI F.Chemistry of essential oils[M].Berlin:Springer Berlin Heidelberg,2007:121-150.
[13]MOREIRA M R C,ALMEIDA A A C D,SOUSA D P D,et al.Anxiolytic-like effects and mechanism of(-)-myrtenol:A monoterpene alcohol[J].Neurosci Lett,2014,579(13):119-124.
[14]IL'INA I V,VOLCHO K P,MIKHALCHENKO O S,et al.Reactions of verbenol epoxide with aromatic aldehydes containing hydroxy or methoxy groups in the presence of montmorillonite clay[J].Helv Chim Acta,2011,94(3):502-513.
[15]YOUSEFZADEH N.Quantitative and qualitative study of bioactive compounds of essential oils of the medicinal plant Artemisia sieberi grown in lorestan(iran)by use of GC-MS technique[J].Org Chem Curr Res,2012,1(4):15-21.
[16]BOTELLA P,CORMA A,NIETO J M L,et al.Selective hydration of dihydromyrcene to dihydromyrcenol over H-beta zeolite[J].Appl Catal A General,2000,203(2):131-138.
[17]KINDEL G,KRAMMER G,SURBURG H,et al.Mixture with wintergreen odor and flavor.EP,US 8226931 B2[P].2012-07-24.
[18]DEGENHARDT J,KOLLNER T G,GERSHENZON J.Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants[J].Phytochemistry,2009,70(15-16):1621-1637.
[19]KAMISHINBARA T.Liquid composition and method for evaluating sorption behavior of flavor compounds using the liquid composition.US 20060068066[P].2006-03-30.
[20]RAVASIO N,ZACCHERIA F,GUIDOTTI M,et al.Mono-and bifunctional heterogeneous catalytic transformation of terpenes and terpenoids[J].Top Catal,2004,27(1-4):157-168.
[21]YOUNG D,JONES M,KITCHING W.Carvone-and piperitone-derived allylic stannanes and aspects of their electrophilic substitution[J].Aust J Chem,1986,39(4):563-573.
[22]孙小玲,林林.由α-蒎烯催化氧化制备马鞭草烯酮的研究[J].化学世界,2009(7):414-417.
[23]TELCI I,DEMIRTAS I,BAYRAM E,et al.Environmental variation on aroma components of pulegone/piperitone rich spearmint(Mentha spicata L.)[J].Ind Crop Prod,2010,32(3):588-592.
[24]LI L,YIN L L,ZHANG L,et al.Composition containing iridoids and uses thereof.EP 1381087[P].2013-04-17.
[25]GUNATA Z,BITTEUR S,BRILLOUET J,et al.Sequential enzymic hydrolysis of potentially aromatic glycosides from grape[J].Carbohyd Res,1988,184(88):139-149.
[26]GUNATA Z,BRILLOUET J M,VOIRIN S,et al.Purification and some properties of anα-arabinofuranosidase from Aspergillus niger.action on grape monoterpenyl arabino-furanosylglucosides[J].J Agr Food Chem,1990,38(3):772-776.
[27]VOIRIN S G,BAUMES R L,BITTEUR S M,et al.Novel monoterpene disaccharide glycosides of Vitis vinifera grapes[J].J Agr Food Chem,1990,38(6):1373-1378.
[28]姜洁.单萜烯在酸性条件下的重排机理的探究[D].广州:华南理工大学,2013.
[29]LARSEN T O,FRISVAD J C.A simple method for collection of volatile metabolites from fungi based on diffusive sampling from petri dishes[J].J Microbioll Method,1994,19(4):297-305.
[30]CARRAU F M,MEDINA K,BOIDO E,et al.De novo synthesis of monoterpenes by Saccharomyces cerevisiae wine yeasts[J].FEMS Microbiol Lett,2005,243(1):107-115.
[31]张艳,卢文玉.酿酒酵母细胞表达异源萜类化合物的研究进展[J].化工进展,2014(5):1265-1270.
[32]吴勇.萜烯类化合物与茶叶香气[J].化学工程与装备,2009(11):123-113.
[33]KALEMBA D,KUNICKA A.Antibacterial and antifungal properties of essential oils[J].Curr Med Chem,2003,10(10):813-29.
[34]王雪梅,谌徽,李雪姣,等.天然活性单萜—柠檬烯的抑菌性能研究[J].吉林农业大学学报,2010,32(1):24-28.
[35]KALP G I,NE E K,MINE K,et al.Antimicrobial screening of Mentha piperita essential oils[J].J Agr Food Chem,2002,50(14):3943-3946.
[36]张婷.芳樟醇通过激活GADD45α/JNK信号通路选择性诱导淋巴细胞白血病细胞凋亡的研究[D].杭州:浙江大学,2007.
[37]DEGENHARDT J,K魻LLNER T G,GERSHENZON J.Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants[J].Phytochemistry,2009,70(15-16):1621-1637.
[38]CROTEAU R,KARP F.Biosynthesis of monoterpenes:Hydrolysis of bornyl pyrophosphate,an essential step in camphor biosynthesis,and hydrolysis of geranyl pyrophosphate,the acyclic precursor of camphor,by enzymes from sage[J].Brit Med J,1990,301(6753):651-653.