食品中萜类化合物来源及功能研究进展
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摘要
食品中萜类化合物来源广泛,部分萜类化合物具有芳香气味,赋予食品独特感官品质,同时,萜类化合物在抗氧化、抑菌、增强人体免疫力和防癌抗癌方面具备明显功效,因此受到国内外学者的广泛关注。该文对萜类化合物在食品中的不同来源、含量进行总结,综述食品中萜类化合物的功能研究现状,以期为萜类化合物在食品工业和人体的高效利用提供依据和参考。
Terpenoids are widely present in foods. Some terpenoids have special aroma,and therefore can give foods unique sensory qualities. Besides,terpenoids are antioxidative,antibacterial,and they can enhance human immunity and prevent cancers. Therefore,they have become a subject of great interests for many researchers. In this paper,recent studies on terpenoids for their sources and contents in foods were summarized. Additionally,current researches on their functions were reviewed,which provides guidance and references for efficient uses of terpenoids in foods industries and human bodies.
Terpenoids are widely present in foods. Some terpenoids have special aroma,and therefore can give foods unique sensory qualities. Besides,terpenoids are antioxidative,antibacterial,and they can enhance human immunity and prevent cancers. Therefore,they have become a subject of great interests for many researchers. In this paper,recent studies on terpenoids for their sources and contents in foods were summarized. Additionally,current researches on their functions were reviewed,which provides guidance and references for efficient uses of terpenoids in foods industries and human bodies.
引文
[1]涂崔,潘秋红,朱保庆,等.葡萄与葡萄酒单萜化合物的研究进展[J].园艺学报,2011,38(7):1 397-1 406.
[2]THOLL D. Terpene synthases and the regulation,diversity and biological roles of terpene metabolism[J]. Current Opinion in Plant Biology,2006,9(3):297-304.
[3]MATARESE F,CUZZOLA A,SCALABRELLI G,et al.Expression of terpene synthase genes associated with the formation of volatiles in different organs of Vitis vinifera[J]. Phytochemistry,2014,105(3):12-24.
[4]师彦平.单萜和倍半萜化学[M].北京:化学工业出版社,2008:4-63.
[5]KIRALAN M,RAMADAN M F. Volatile oxidation compounds and stability of safflower,sesame and canola coldpressed oils as affected by thermal and microwave treatments[J]. Journal of Oleo Science,2016,65(10):825-833.
[6]RAWSON A,TIWARI B K,TUOHY M G,et al. Effect of ultrasound and blanching pretreatments onpolyacetylene and carotenoid content of hot air and freeze dried carrot discs[J]. Ultrasonics Sonochemistry,2011,18(5):1 172-1 179.
[7]吴勇.萜烯类化合物与茶叶香气[J].化学工程与装备,2009(11):123-125.
[8]WEDLER H B,PEMBERTON R P,TANTILLODJ,et al.Carbocations and the complex flavor and bouquet of wine:Mechanistic aspects of terpene biosynthesis in wine grapes[J]. Molecules,2015,20(6):10 781-10 792.
[9]国家卫生和计划生育委员会.食品安全国家标准食品添加剂使用标准:GB 2760—2014[S].北京:中国标准出版社,2015:119-184.
[10]陈尚钘,赵玲华,徐小军.天然芳樟醇资源及其开发利用[J].林业工程学报,2013,27(2):13-17.
[11]洪晴悦,张玉.超声波辅助提取牡丹籽毛油的工艺优化及脂肪酸组成分析[J].食品与发酵工业,2018,44(3):159-164.
[12]何雅静,苏志豪,宁晓强,等.超声波辅助提取菜籽油工艺优化及脂肪酸组成分析[J].食品工业,2018,39(7):75-79.
[13]ORTEGA-RAMIREZ L A,RODRIGUEZ-GARCIA I,LEYYA J M,et al. Potential of medicinal plants as antimicrobial and antioxidant agents in food industry:A hypothesis[J]. Journal of Food Science,2014,79(2):129-137.
[14]YUAN Gaofeng,CHEN Xiaoe,LI Duo. Chitosan films and coatings containing essential oils:The antioxidant and antimicrobial activity, and application in food systems[J]. Food Research International,2016,89(Pt 1):117.
[15]张冲,李嘉诚,周雪晴,等.超临界CO2萃取迷迭香精油及其化学成分分析[J].精细化工,2008,25(1):62-64.
[16]BI Xiaoxu,HAN Li,QU Tiange,et al. Anti-inflammatory effects,SAR,and action mechanism of monoterpenoids from radix paeoniae alba on LPS-stimulated RAW 264. 7cells[J]. Molecules,2017,22(5):715.
[17]MAFUD A C,SILVA M P,MONTEIRO D C,et al.Structural parameters,molecular properties,and biological evaluation of someterpenes targeting Schistosoma mansoni parasite[J]. Chemico-Biological Interactions,2016,244:129-139.
[18]KLADNIEW B R. Suppression by geraniol of the growth of A549 human lung adenocarcinoma cells and inhibition of the mevalonate pathway in culture and in vivo:Potential use in cancer chemotherapy[J]. Nutrition&Cancer,2014,66(5):888-895.
[19]张建红,刘琬菁,罗红梅.药用植物萜类化合物活性研究进展[J].世界科学技术-中医药现代化,2018,20(3):419-430.
[20]马志扬,李湖中,刘德文,等.食品营养强化剂化合物使用频次的调查[J].中国食品卫生杂志,2017(6).723-728.
[21]中华人民共和国卫生部. GB14880—2012食品安全国家标准食品营养强化剂使用标准[S].北京:中国标准出版社,2012. 3-24.
[22]蔡晓.灵芝及保健食品中三萜类化合物的含量测定探讨[J].中国卫生检验杂志,2013,23(2):307-308.
[23]冯杰,冯娜,唐庆九,等.补料方式对灵芝菌丝体液态深层发酵合成灵芝三萜的影响[J].食品科学,2017,38(12):57-62.
[24]陈芳,张晓旭,杨晓,等.威代尔葡萄成熟及后熟过程中游离态萜烯类香气的变化[J].中国食品学报,2010,10(6):187-192.
[25]田婷婷,马英华,解伟伟,等. LC-MS/MS同时测定蓝萼香菜中4种二萜类成分及其聚类分析[J].中国中药杂志,2016,41(2):250-256.
[26]孙宝国,李贺贺,胡萧梅,等.健康白酒的发展趋势[J].中国食品学报,2016,16(8):1-6.
[27]全巧玲,江伟,王德良,等.单萜醇类在啤酒发酵过程中的变化及对酒花香气的贡献[J].食品与发酵工业,2013,39(5):170-175.
[28]祝海珍. HPLC法测定动物肝脏中维生素A含量的不确定度评定[J].食品研究与开发,2018(7). 160-165.
[29]宋诗清,童彦尊,冯涛,等.金佛手香气物质的多维分析及其特征香气物质的确定[J].食品科学,2017,38(24):94-100.
[30]何湘漪,何洪巨,范志红,等.烹调方法对3种叶菜中类黄酮和类胡萝卜素的影响[J].中国食品学报,2016,16(7):276-282.
[31]ALASALVAR C,TOPAL B,SERPEN A,et al. Flavor characteristics of seven grades of black tea produced in Turkey[J]. Journal of Agricultural&Food Chemistry,2012,60(25):6 323.
[32]ZHU Jiancai,CHEN Feng,WANG Lingying, et al.Comparison of aroma-active volatiles in oolong tea infusions using GC-Olfactometry,GC-FPD,and GC-MS[J].Journal of Agricultural&Food Chemistry, 2015, 63(34):7 499-7 510.
[33]李娜娜,束廷廷,梁艳英,等.不同采收期对爱格丽葡萄酒及蒸馏酒香气成分的影响[J].食品科学,2018,39(2):215-221.
[34]刘纯友,马美湖,靳国锋,等.角鲨烯及其生物活性研究进展[J].中国食品学报,2015,15(5):147-156.
[35]PATEIRO M,FRANCO D,CARRIL J A,et al. Changes on physico-chemical properties,lipid oxidation and volatile compounds during the manufacture of celta dry-cured loin[J]. Journal of Food Science&Technology,2015,52(8):1-11.
[36]GONZáLEZ-BURGOS E,GóMEZ-SERRANILLOS M P.Terpene compounds in nature:A review of their potential antioxidant activity[J]. Current Medicinal Chemistry,2012,19(31):5 319-5 341.
[37]GHARIB E L,SILVA J A T D. Composition,total phenolic content and antioxidant activity of the essential oil of four lamiaceae herbs[J]. Medicinal and Aromatic Plant Science and Biotechnology,2013,7(1):19-27.
[38]AMORATI R,FOTI M C,VALGIMIGLI L. Antioxidant activity of essential oils:A critical review[J]. Journal of Agricultural&Food Chemistry,2013,61(46):10 835-10 847.
[39]RIACHI L G,MARIA C A B D. Peppermint antioxidants revisited[J]. Food Chemistry,2015,176(176):72-81.
[40]OMORUYI B E,AFOLAYAN A J,BRADLEY G. Chemical composition profiling and antifungal activity of the essential oil and plant extracts of mesembryanthemum edule(L.)bolus leaves[J]. Afr J Tradit Complement Altern Med,2014,11(4):19-30.
[41]YANG Tsungshi,CHAO LK,LIU Taiti. Antimicrobial activity of the essential oil of Glossogyne tenuifolia against selected pathogens[J]. Journal of the Science of Food&Agriculture,2015,94(14):2 965-2 971.
[42]PICCINELLI A C,SANTOS J A,KONKIEWITZ E C,et al. Antihyperalgesic and antidepressive actions of(R)-(+)-limonene,±-phellandrene,and essential oil from Schinus terebinthifolius fruits in a neuropathic pain model[J]. Nutritional Neuroscience,2015,18(5):217-224.
[43]LI Yun,XU Yuling,LAI Yanni,et al. Intranasal co-administration of 1,8-cineole with influenza vaccine provide cross-protection against influenza virus infection[J]. Phytomedicine,2017,34:127-135.
[44]GUO Jiao,BEI Weijian,HU Yinming,et al. A new TCM formula FTZ lowers serum cholesterol by regulating HMGCo A reductase and CYP7A1 in hyperlipidemic rats[J].Journal of Ethnopharmacology,2011,135(2):299-307.
[45]ORELLANA-PAUCAR A M, SERRUVSA S, AFRIKANOVA T,et al. Anticonvulsant activity of bisabolene sesquiterpenoids of Curcuma longa in zebrafish and mouse seizure models[J]. Epilepsy&Behavior,2012,24(1):14-22.
[46]李国华,李晔,梅锡玲,等.灵芝三萜类化合物研究进展[J].中草药,2015,46(12):1 858-1 862.
[47]唐瑶,曹婉鑫,陈洋.三萜皂苷应用研究进展[J].农业工程技术(农产品加工业),2014(10):42-44.
[48]ELSHARIF S,BUETTNER A. Structure-odor relationship study ongeraniol,nerol and their synthesized oxygenated derivatives[J]. Journal of Agricultural&Food Chemistry,2018,66(10):2 324-2 333.
[49]LI Jingzhe,LIU Changzhen,SATO T. Novel antitumor invasive actions of P-Cymene by decreasing MMP-9/TIMP-1 expression ratio in human fibrosarcoma HT-1080cells[J]. Biological&Pharmaceutical Bulletin,2016,39(8):1 247-1 253.
[50]SILVA B G D,FILETI A M F,FOGLIO M A,et al. Supercritical carbon dioxide extraction of compounds from Schinus terebinthifolius,raddi fruits:Effects of operating conditions on global yield,volatile compounds,and antiproliferative activity against human tumor cell lines[J].Journal of Supercritical Fluids,2017,130:10-16.
[2]THOLL D. Terpene synthases and the regulation,diversity and biological roles of terpene metabolism[J]. Current Opinion in Plant Biology,2006,9(3):297-304.
[3]MATARESE F,CUZZOLA A,SCALABRELLI G,et al.Expression of terpene synthase genes associated with the formation of volatiles in different organs of Vitis vinifera[J]. Phytochemistry,2014,105(3):12-24.
[4]师彦平.单萜和倍半萜化学[M].北京:化学工业出版社,2008:4-63.
[5]KIRALAN M,RAMADAN M F. Volatile oxidation compounds and stability of safflower,sesame and canola coldpressed oils as affected by thermal and microwave treatments[J]. Journal of Oleo Science,2016,65(10):825-833.
[6]RAWSON A,TIWARI B K,TUOHY M G,et al. Effect of ultrasound and blanching pretreatments onpolyacetylene and carotenoid content of hot air and freeze dried carrot discs[J]. Ultrasonics Sonochemistry,2011,18(5):1 172-1 179.
[7]吴勇.萜烯类化合物与茶叶香气[J].化学工程与装备,2009(11):123-125.
[8]WEDLER H B,PEMBERTON R P,TANTILLODJ,et al.Carbocations and the complex flavor and bouquet of wine:Mechanistic aspects of terpene biosynthesis in wine grapes[J]. Molecules,2015,20(6):10 781-10 792.
[9]国家卫生和计划生育委员会.食品安全国家标准食品添加剂使用标准:GB 2760—2014[S].北京:中国标准出版社,2015:119-184.
[10]陈尚钘,赵玲华,徐小军.天然芳樟醇资源及其开发利用[J].林业工程学报,2013,27(2):13-17.
[11]洪晴悦,张玉.超声波辅助提取牡丹籽毛油的工艺优化及脂肪酸组成分析[J].食品与发酵工业,2018,44(3):159-164.
[12]何雅静,苏志豪,宁晓强,等.超声波辅助提取菜籽油工艺优化及脂肪酸组成分析[J].食品工业,2018,39(7):75-79.
[13]ORTEGA-RAMIREZ L A,RODRIGUEZ-GARCIA I,LEYYA J M,et al. Potential of medicinal plants as antimicrobial and antioxidant agents in food industry:A hypothesis[J]. Journal of Food Science,2014,79(2):129-137.
[14]YUAN Gaofeng,CHEN Xiaoe,LI Duo. Chitosan films and coatings containing essential oils:The antioxidant and antimicrobial activity, and application in food systems[J]. Food Research International,2016,89(Pt 1):117.
[15]张冲,李嘉诚,周雪晴,等.超临界CO2萃取迷迭香精油及其化学成分分析[J].精细化工,2008,25(1):62-64.
[16]BI Xiaoxu,HAN Li,QU Tiange,et al. Anti-inflammatory effects,SAR,and action mechanism of monoterpenoids from radix paeoniae alba on LPS-stimulated RAW 264. 7cells[J]. Molecules,2017,22(5):715.
[17]MAFUD A C,SILVA M P,MONTEIRO D C,et al.Structural parameters,molecular properties,and biological evaluation of someterpenes targeting Schistosoma mansoni parasite[J]. Chemico-Biological Interactions,2016,244:129-139.
[18]KLADNIEW B R. Suppression by geraniol of the growth of A549 human lung adenocarcinoma cells and inhibition of the mevalonate pathway in culture and in vivo:Potential use in cancer chemotherapy[J]. Nutrition&Cancer,2014,66(5):888-895.
[19]张建红,刘琬菁,罗红梅.药用植物萜类化合物活性研究进展[J].世界科学技术-中医药现代化,2018,20(3):419-430.
[20]马志扬,李湖中,刘德文,等.食品营养强化剂化合物使用频次的调查[J].中国食品卫生杂志,2017(6).723-728.
[21]中华人民共和国卫生部. GB14880—2012食品安全国家标准食品营养强化剂使用标准[S].北京:中国标准出版社,2012. 3-24.
[22]蔡晓.灵芝及保健食品中三萜类化合物的含量测定探讨[J].中国卫生检验杂志,2013,23(2):307-308.
[23]冯杰,冯娜,唐庆九,等.补料方式对灵芝菌丝体液态深层发酵合成灵芝三萜的影响[J].食品科学,2017,38(12):57-62.
[24]陈芳,张晓旭,杨晓,等.威代尔葡萄成熟及后熟过程中游离态萜烯类香气的变化[J].中国食品学报,2010,10(6):187-192.
[25]田婷婷,马英华,解伟伟,等. LC-MS/MS同时测定蓝萼香菜中4种二萜类成分及其聚类分析[J].中国中药杂志,2016,41(2):250-256.
[26]孙宝国,李贺贺,胡萧梅,等.健康白酒的发展趋势[J].中国食品学报,2016,16(8):1-6.
[27]全巧玲,江伟,王德良,等.单萜醇类在啤酒发酵过程中的变化及对酒花香气的贡献[J].食品与发酵工业,2013,39(5):170-175.
[28]祝海珍. HPLC法测定动物肝脏中维生素A含量的不确定度评定[J].食品研究与开发,2018(7). 160-165.
[29]宋诗清,童彦尊,冯涛,等.金佛手香气物质的多维分析及其特征香气物质的确定[J].食品科学,2017,38(24):94-100.
[30]何湘漪,何洪巨,范志红,等.烹调方法对3种叶菜中类黄酮和类胡萝卜素的影响[J].中国食品学报,2016,16(7):276-282.
[31]ALASALVAR C,TOPAL B,SERPEN A,et al. Flavor characteristics of seven grades of black tea produced in Turkey[J]. Journal of Agricultural&Food Chemistry,2012,60(25):6 323.
[32]ZHU Jiancai,CHEN Feng,WANG Lingying, et al.Comparison of aroma-active volatiles in oolong tea infusions using GC-Olfactometry,GC-FPD,and GC-MS[J].Journal of Agricultural&Food Chemistry, 2015, 63(34):7 499-7 510.
[33]李娜娜,束廷廷,梁艳英,等.不同采收期对爱格丽葡萄酒及蒸馏酒香气成分的影响[J].食品科学,2018,39(2):215-221.
[34]刘纯友,马美湖,靳国锋,等.角鲨烯及其生物活性研究进展[J].中国食品学报,2015,15(5):147-156.
[35]PATEIRO M,FRANCO D,CARRIL J A,et al. Changes on physico-chemical properties,lipid oxidation and volatile compounds during the manufacture of celta dry-cured loin[J]. Journal of Food Science&Technology,2015,52(8):1-11.
[36]GONZáLEZ-BURGOS E,GóMEZ-SERRANILLOS M P.Terpene compounds in nature:A review of their potential antioxidant activity[J]. Current Medicinal Chemistry,2012,19(31):5 319-5 341.
[37]GHARIB E L,SILVA J A T D. Composition,total phenolic content and antioxidant activity of the essential oil of four lamiaceae herbs[J]. Medicinal and Aromatic Plant Science and Biotechnology,2013,7(1):19-27.
[38]AMORATI R,FOTI M C,VALGIMIGLI L. Antioxidant activity of essential oils:A critical review[J]. Journal of Agricultural&Food Chemistry,2013,61(46):10 835-10 847.
[39]RIACHI L G,MARIA C A B D. Peppermint antioxidants revisited[J]. Food Chemistry,2015,176(176):72-81.
[40]OMORUYI B E,AFOLAYAN A J,BRADLEY G. Chemical composition profiling and antifungal activity of the essential oil and plant extracts of mesembryanthemum edule(L.)bolus leaves[J]. Afr J Tradit Complement Altern Med,2014,11(4):19-30.
[41]YANG Tsungshi,CHAO LK,LIU Taiti. Antimicrobial activity of the essential oil of Glossogyne tenuifolia against selected pathogens[J]. Journal of the Science of Food&Agriculture,2015,94(14):2 965-2 971.
[42]PICCINELLI A C,SANTOS J A,KONKIEWITZ E C,et al. Antihyperalgesic and antidepressive actions of(R)-(+)-limonene,±-phellandrene,and essential oil from Schinus terebinthifolius fruits in a neuropathic pain model[J]. Nutritional Neuroscience,2015,18(5):217-224.
[43]LI Yun,XU Yuling,LAI Yanni,et al. Intranasal co-administration of 1,8-cineole with influenza vaccine provide cross-protection against influenza virus infection[J]. Phytomedicine,2017,34:127-135.
[44]GUO Jiao,BEI Weijian,HU Yinming,et al. A new TCM formula FTZ lowers serum cholesterol by regulating HMGCo A reductase and CYP7A1 in hyperlipidemic rats[J].Journal of Ethnopharmacology,2011,135(2):299-307.
[45]ORELLANA-PAUCAR A M, SERRUVSA S, AFRIKANOVA T,et al. Anticonvulsant activity of bisabolene sesquiterpenoids of Curcuma longa in zebrafish and mouse seizure models[J]. Epilepsy&Behavior,2012,24(1):14-22.
[46]李国华,李晔,梅锡玲,等.灵芝三萜类化合物研究进展[J].中草药,2015,46(12):1 858-1 862.
[47]唐瑶,曹婉鑫,陈洋.三萜皂苷应用研究进展[J].农业工程技术(农产品加工业),2014(10):42-44.
[48]ELSHARIF S,BUETTNER A. Structure-odor relationship study ongeraniol,nerol and their synthesized oxygenated derivatives[J]. Journal of Agricultural&Food Chemistry,2018,66(10):2 324-2 333.
[49]LI Jingzhe,LIU Changzhen,SATO T. Novel antitumor invasive actions of P-Cymene by decreasing MMP-9/TIMP-1 expression ratio in human fibrosarcoma HT-1080cells[J]. Biological&Pharmaceutical Bulletin,2016,39(8):1 247-1 253.
[50]SILVA B G D,FILETI A M F,FOGLIO M A,et al. Supercritical carbon dioxide extraction of compounds from Schinus terebinthifolius,raddi fruits:Effects of operating conditions on global yield,volatile compounds,and antiproliferative activity against human tumor cell lines[J].Journal of Supercritical Fluids,2017,130:10-16.