不同品种小茴香果实挥发性成分、多酚、黄酮含量及抗氧化性比较分析
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摘要
香辛料小茴香有多个品种,而对不同品种间挥发性成分和抗氧化品质差异研究未见报道。采用顶空固相微萃取-气相色谱质谱联用法结合主成分分析,对5个小茴香品种果实的挥发性成分、多酚、黄酮含量及抗氧化性能进行检测和分析。结果表明,共有75种挥发性成分被检测出,主要以萜烯类化合物为主;多酚、黄酮含量及抗氧化能力以大高杆小茴香最高;结合相关性分析和主成分分析方法,发现氧化单萜烯类与功能成分、抗氧化性能之间存在正相关关系。将5种小茴香划分为3类,即低杆小茴香、小高杆小茴香和高杆小茴香聚为第一类,有较高含量的萜烯类化合物;大高杆小茴香聚为第二类,有较强的抗氧化活性;土茴香聚为第三类,具有较高含量的总倍半萜烯类化合物和萜烯类衍生物。为商业利用挥发性成分判定和描述抗氧化指标和多酚、黄酮含量提供可能性,并为科学评价和利用不同品种小茴香果实品质特性提供技术支持。
Differences in volatile compounds and antioxidant capacities among various cultivars of Foeniculum vulgare Mill have not been reported yet. The contents of volatile compounds,polyphenols and flavonoids,and antioxidant capacities of five cultivars of fennel were analyzed by headspace solid-phase microextraction-gas chromatography mass spectrometry and principal component analysis. The results showed that 75 volatile compounds were detected,which were mainly terpenoids. The contents of polyphenols and flavonoids,and antioxidant capacity showed the highest in the highly stem. According to correlation analysis and principal component analysis,oxidized monoterpenes had positive correlations with functional components and antioxidant capacities. Five cultivars were divided into three categories: short stem,fairly long stem,and long stem were clustered into the first category,which showed higher contents of terpenoids. Highly stem fennel was clustered into the second category,which had higher antioxidant capacity.Local fennel was clustered into the third category,which had higher contents of total sesquiterpenes and derivatives of terpenoids. This study offers possibility to commercially determine the antioxidant capacity,polyphenols and flavonoid contents of fennel seeds through volatile compounds,and provide technical supports to scientifically evaluate and utilize quality characteristics of different fennel cultivars.
Differences in volatile compounds and antioxidant capacities among various cultivars of Foeniculum vulgare Mill have not been reported yet. The contents of volatile compounds,polyphenols and flavonoids,and antioxidant capacities of five cultivars of fennel were analyzed by headspace solid-phase microextraction-gas chromatography mass spectrometry and principal component analysis. The results showed that 75 volatile compounds were detected,which were mainly terpenoids. The contents of polyphenols and flavonoids,and antioxidant capacity showed the highest in the highly stem. According to correlation analysis and principal component analysis,oxidized monoterpenes had positive correlations with functional components and antioxidant capacities. Five cultivars were divided into three categories: short stem,fairly long stem,and long stem were clustered into the first category,which showed higher contents of terpenoids. Highly stem fennel was clustered into the second category,which had higher antioxidant capacity.Local fennel was clustered into the third category,which had higher contents of total sesquiterpenes and derivatives of terpenoids. This study offers possibility to commercially determine the antioxidant capacity,polyphenols and flavonoid contents of fennel seeds through volatile compounds,and provide technical supports to scientifically evaluate and utilize quality characteristics of different fennel cultivars.
引文
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[3]蒋军辉,徐小娜,杨慧仙,等. GC-MS结合直观推导式演进特征投影法(HELP)分析大茴香和小茴香挥发性化学成分[J].南华大学学报(自然科学版),2011,25(4):91-96.
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[5]王晓敏,李军,高艳明,等.茴香的研究进展[J].河北农业科学,2013(5):37-40.
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[8]张禄捷,刘韬,李荣,等.天然调味香料小茴香挥发油的研究进展[J].中国调味品,2015(3):117-120.
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[10]NAJDOSKA M, BOGDANOV J, ZDRAVKOVSKI Z.TLC and GC-MS analyses of essential oil isolated from Macedonian Foeniculi fructus[J]. Macedonian Pharmaceutical Bulletin,2010,56(1-2):29-36.
[11]李蜀眉,王丽荣,陈永青,等.小茴香中黄酮类化合物提取及抗氧化性研究[J].中国调味品,2016,41(12):29-32.
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[13]罗静,钟永科,李明明,等.小茴香储存过程中挥发性成分的变化[J].中国调味品,2016,41(3):49-52.
[14]EBRAHIMABADI A H,DJAFARIBIDGOLI Z,MAZOOCHI A,et al. Essential oils composition,antioxidant and antimicrobial activity of the leaves and flowers of Chaerophyllum macropodum Boiss[J]. Food Control,2010,21(8):1 173-1 178.
[15]CHEN L Y,CHENG C W,LIANG J Y. Effect of esterification condensation on the Folin-Ciocalteu method for the quantitative measurement of total phenols[J]. Food Chemistry,2015,170(12):10-15.
[16]CHEN G L,CHEN S G,XIAO Y,et al. Antioxidant capacities and total phenolic contents of 30 flowers[J]. Industrial Crops&Products,2018,111:430-445.
[17]WU G,JOHNSON S K,BORNMAN J F,et al. Changes in whole grain polyphenols and antioxidant activity of six sorghum genotypes under different irrigation treatments[J]. Food Chemistry,2017,214:199-207.
[18]BENZIE I F F,STRAIN J J. The ferric reducing ability of plasma(FRAP)as a measure of “antioxidant power”:The FRAP assay[J]. Analytical Biochemistry,1996,239(1):70-76.
[19]YUN S,LIANG J,PENG X,et al. Total phenolics,flavonoids,antioxidant capacity in rice grain and their relations to grain color,size and weight[J]. Journal of Cereal Science,2009,49(1):106-111.
[20]ZHAO H,FAN W,DONG J,et al. Evaluation of antioxidant activities and total phenolic contents of typical malting barley varieties[J]. Food Chemistry,2008,107(1):296-304.
[21]CHEN Q,GAN Z,ZHAO J,et al. In vitro,comparison of antioxidant capacity of cumin(Cuminum cyminum L.)oils and their main components[J]. LWT-Food Science and Technology,2014,55(2):632-637.
[22]VELIOGLU Y S,MAZZA G,GAO L,et al. Antioxidant activity and total phenolics in selected fruits,vegetables,and grain products[J]. Journal of Agricultural&Food Chemistry,1998,46(10):4 113-4 117.
[23]李峰,程侠,叶荣飞,等.在线热裂解/气相色谱-质谱联用技术研究八角茴香油的热裂解行为[J].分析测试学报,2015,34(4):448-452.
[24]李源栋,段焰青,王红霞,等. GC/MS法结合保留指数分析鼠尾草油中香味成分[J].粮食与油脂,2016,29(3):65-68.
[25]朱金霞,郭生虎,李苗,等.海原小茴香优良品种筛选及挥发油化学成分比较研究[J].种子,2009,28(9):47-49.
[26]AKGüL A,BAYRAK A. Comparative volatile oil composition of various parts from Turkish bitter fennel(Foeniculum vulgare var vulgare)[J]. Food Chemistry,1988,30(4):319-323.
[27]DIAO W R,HU Q P,ZHANG H,et al. Chemical composition,antibacterial activity and mechanism of action of essential oil from seeds of fennel(Foeniculum vulgare Mill.)[J]. Food Control,2014,35(1):109-116.
[28]郑甜田,陶永生,张敏,等. 10种产地小茴香果实挥发油成分分析[J].昆明医科大学学报,2017(11):19-24.
[29]王强,殷超,彭秧.比较研究新疆小茴香不同溶剂提取物的抗氧化活性[J].中国酿造,2012,31(6):95-97.
[30]MOTAMED S M,NAGHIBI F. Antioxidant activity of some edible plants of the Turkmen Sahra region in northern Iran[J]. Food Chemistry,2010,119(4):1 637-1 642.
[31]HINNEBURG I,HJD D,HILTUNEN R. Antioxidant activities of extracts from selected culinary herbs and spices[J]. Food Chemistry,2006,97(1):122-129.
[32]张翠利,付丽娜,杨小云,等.活性氧自由基与细胞衰老关系的研究进展[J].广州化工,2015(19):5-7.
[33]OKTAY M,GULCIN I,KUFREVIOGLU O I. Determination of in vitro antioxidant activity of fennel(Foeniculum vulgare)seed extracts[J]. LWT-Food Science and Technology,2003,36(2):263-271.
[34]MIRALIAKBARI H,SHAHIDI F. Antioxidant activity of minor components of tree nut oils[J]. Food Chemistry,2008,111(2):421-427.
[35]RUFINO M D S M,ALVES R E,BRITO E S D,et al.Bioactive compounds and antioxidant capacities of 18 nontraditional tropical fruits from Brazil[J]. Food Chemistry,2010,121(4):996-1 002.
[36]SALAMA Z A,BAZ F K E,GAAFAR A A,et al. Antioxidant activities of phenolics,flavonoids and vitamin C in two cultivars of fennel(Foeniculum vulgare Mill.)in responses to organic and bio-organic fertilizers[J]. Journal of the Saudi Society of Agricultural Sciences,2015,14(1):91-99.
[37]GACHKAR L,YADEGARI D,REZAEI M B,et al.Chemical and biological characteristics of Cuminum cyminum and Rosmarinus officinalis essential oils[J]. Food Chemistry,2007,102(3):898-904.
[38]FRANKEL E N,MEYER A S. The problems of using one-dimensional methods to evaluate multifunctional food and biological antioxidants[J]. Journal of the Science of Food&Agriculture,2000,80(13):1 925-1 941.
[39]MIRALIAKBARI H,SHAHIDI F. Antioxidant activity of minor components of tree nut oils[J]. Food Chemistry,2008,111(2):421-427.
[40]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.
[2]付起凤,张艳丽,许树军,等.小茴香化学成分及药理作用的研究进展[J].中医药信息,2008,25(5):24-26.
[3]蒋军辉,徐小娜,杨慧仙,等. GC-MS结合直观推导式演进特征投影法(HELP)分析大茴香和小茴香挥发性化学成分[J].南华大学学报(自然科学版),2011,25(4):91-96.
[4]何金明,肖艳辉,王羽梅,等.钾浓度对茴香植株生长发育、精油含量和组分的影响[J].生态环境学报,2013(3):417-422.
[5]王晓敏,李军,高艳明,等.茴香的研究进展[J].河北农业科学,2013(5):37-40.
[6]朱金霞,郭生虎,郑国保.紫外分光光度法测定小茴香不同器官中总黄酮[J].北方园艺,2010(19):33-34.
[7]高莉.小茴香化学成分的初步研究[D].乌鲁木齐:新疆大学,2005:20-28.
[8]张禄捷,刘韬,李荣,等.天然调味香料小茴香挥发油的研究进展[J].中国调味品,2015(3):117-120.
[9]PARTHASARATHY V A. Chemistry of Spices[M]. CABI,2008:227-241.
[10]NAJDOSKA M, BOGDANOV J, ZDRAVKOVSKI Z.TLC and GC-MS analyses of essential oil isolated from Macedonian Foeniculi fructus[J]. Macedonian Pharmaceutical Bulletin,2010,56(1-2):29-36.
[11]李蜀眉,王丽荣,陈永青,等.小茴香中黄酮类化合物提取及抗氧化性研究[J].中国调味品,2016,41(12):29-32.
[12]杨洋,韦小英,阮征.国内外天然食品抗氧化剂的研究进展[J].食品科学,2002,23(10):137-138.
[13]罗静,钟永科,李明明,等.小茴香储存过程中挥发性成分的变化[J].中国调味品,2016,41(3):49-52.
[14]EBRAHIMABADI A H,DJAFARIBIDGOLI Z,MAZOOCHI A,et al. Essential oils composition,antioxidant and antimicrobial activity of the leaves and flowers of Chaerophyllum macropodum Boiss[J]. Food Control,2010,21(8):1 173-1 178.
[15]CHEN L Y,CHENG C W,LIANG J Y. Effect of esterification condensation on the Folin-Ciocalteu method for the quantitative measurement of total phenols[J]. Food Chemistry,2015,170(12):10-15.
[16]CHEN G L,CHEN S G,XIAO Y,et al. Antioxidant capacities and total phenolic contents of 30 flowers[J]. Industrial Crops&Products,2018,111:430-445.
[17]WU G,JOHNSON S K,BORNMAN J F,et al. Changes in whole grain polyphenols and antioxidant activity of six sorghum genotypes under different irrigation treatments[J]. Food Chemistry,2017,214:199-207.
[18]BENZIE I F F,STRAIN J J. The ferric reducing ability of plasma(FRAP)as a measure of “antioxidant power”:The FRAP assay[J]. Analytical Biochemistry,1996,239(1):70-76.
[19]YUN S,LIANG J,PENG X,et al. Total phenolics,flavonoids,antioxidant capacity in rice grain and their relations to grain color,size and weight[J]. Journal of Cereal Science,2009,49(1):106-111.
[20]ZHAO H,FAN W,DONG J,et al. Evaluation of antioxidant activities and total phenolic contents of typical malting barley varieties[J]. Food Chemistry,2008,107(1):296-304.
[21]CHEN Q,GAN Z,ZHAO J,et al. In vitro,comparison of antioxidant capacity of cumin(Cuminum cyminum L.)oils and their main components[J]. LWT-Food Science and Technology,2014,55(2):632-637.
[22]VELIOGLU Y S,MAZZA G,GAO L,et al. Antioxidant activity and total phenolics in selected fruits,vegetables,and grain products[J]. Journal of Agricultural&Food Chemistry,1998,46(10):4 113-4 117.
[23]李峰,程侠,叶荣飞,等.在线热裂解/气相色谱-质谱联用技术研究八角茴香油的热裂解行为[J].分析测试学报,2015,34(4):448-452.
[24]李源栋,段焰青,王红霞,等. GC/MS法结合保留指数分析鼠尾草油中香味成分[J].粮食与油脂,2016,29(3):65-68.
[25]朱金霞,郭生虎,李苗,等.海原小茴香优良品种筛选及挥发油化学成分比较研究[J].种子,2009,28(9):47-49.
[26]AKGüL A,BAYRAK A. Comparative volatile oil composition of various parts from Turkish bitter fennel(Foeniculum vulgare var vulgare)[J]. Food Chemistry,1988,30(4):319-323.
[27]DIAO W R,HU Q P,ZHANG H,et al. Chemical composition,antibacterial activity and mechanism of action of essential oil from seeds of fennel(Foeniculum vulgare Mill.)[J]. Food Control,2014,35(1):109-116.
[28]郑甜田,陶永生,张敏,等. 10种产地小茴香果实挥发油成分分析[J].昆明医科大学学报,2017(11):19-24.
[29]王强,殷超,彭秧.比较研究新疆小茴香不同溶剂提取物的抗氧化活性[J].中国酿造,2012,31(6):95-97.
[30]MOTAMED S M,NAGHIBI F. Antioxidant activity of some edible plants of the Turkmen Sahra region in northern Iran[J]. Food Chemistry,2010,119(4):1 637-1 642.
[31]HINNEBURG I,HJD D,HILTUNEN R. Antioxidant activities of extracts from selected culinary herbs and spices[J]. Food Chemistry,2006,97(1):122-129.
[32]张翠利,付丽娜,杨小云,等.活性氧自由基与细胞衰老关系的研究进展[J].广州化工,2015(19):5-7.
[33]OKTAY M,GULCIN I,KUFREVIOGLU O I. Determination of in vitro antioxidant activity of fennel(Foeniculum vulgare)seed extracts[J]. LWT-Food Science and Technology,2003,36(2):263-271.
[34]MIRALIAKBARI H,SHAHIDI F. Antioxidant activity of minor components of tree nut oils[J]. Food Chemistry,2008,111(2):421-427.
[35]RUFINO M D S M,ALVES R E,BRITO E S D,et al.Bioactive compounds and antioxidant capacities of 18 nontraditional tropical fruits from Brazil[J]. Food Chemistry,2010,121(4):996-1 002.
[36]SALAMA Z A,BAZ F K E,GAAFAR A A,et al. Antioxidant activities of phenolics,flavonoids and vitamin C in two cultivars of fennel(Foeniculum vulgare Mill.)in responses to organic and bio-organic fertilizers[J]. Journal of the Saudi Society of Agricultural Sciences,2015,14(1):91-99.
[37]GACHKAR L,YADEGARI D,REZAEI M B,et al.Chemical and biological characteristics of Cuminum cyminum and Rosmarinus officinalis essential oils[J]. Food Chemistry,2007,102(3):898-904.
[38]FRANKEL E N,MEYER A S. The problems of using one-dimensional methods to evaluate multifunctional food and biological antioxidants[J]. Journal of the Science of Food&Agriculture,2000,80(13):1 925-1 941.
[39]MIRALIAKBARI H,SHAHIDI F. Antioxidant activity of minor components of tree nut oils[J]. Food Chemistry,2008,111(2):421-427.
[40]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.