不同甲酯化方法对开口箭地上部位脂肪酸分析的影响
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摘要
利用索氏提取器提取开口箭地上部位脂溶性成分,采用BF_3-CH_3OH和HCl-CH_3OH分别进行甲酯化处理,运用气相色谱-质谱联用技术(GC-MS)对其成分进行分离和鉴定,比较2种不同甲酯化方法对开口箭地上部位脂肪酸成分分析的影响。结果表明,通过BF_3-CH_3OH甲酯化和HCl-CH_3OH甲酯化预处理后,经GC-MS测定和NIST2011谱库检索,分别从开口箭地上部位得到化学成分31种和25种,包括脂肪酸成分21种,共有成分13种,其中正十二烷酸、癸二酸、正十四烷酸、正十六烷酸、(Z,Z)-9,12-十八碳二烯酸、(Z,Z,Z)-9,12,15-十八碳三烯酸和正十九烷酸的含量差异明显。正十三烷酸、肉豆蔻油酸、三甲基硅烷基肉豆蔻酸、(Z,Z)-7,10-十六碳二烯酸,(Z)-9-十六碳烯酸,3,5-二叔丁基-4-羟基苯丙酸,L-抗坏血酸-2,6-二十六烷酸,(Z,Z,Z)-9,12,15-十八碳三烯酸和16-甲基十七碳酸均为首次从开口箭中分离鉴定得到。BF_3-CH_3OH甲酯化方法处理更适于开口箭地上部位脂肪酸的分析测定,有利于进一步开发利用其含有的不饱和脂肪酸。
Effects of two different methyl esterification methods on the results of fatty acid analysis of the aerial parts of Campylandra chinensis were examined.The fatty acid components from the aerial parts of C.chinensis were extracted by Soxhlet extractor,identified and determined based on gas chromatographymass spectrometry(GC-MS)after methyl esterification by using BF_3-CH_3OH and HCl-CH_3OH.Totally 31(BF_3-CH_3OH method)and 25(HCl-CH_3OH method)chemical constituents were measured and retrieved by GC-MS coupled with NIST2011 spectral library,including 21 kinds of fatty acid and 13 other components,the obvious content differences were dodecanoic acid,nonanedioic acid,tetradecanoic acid,hexadecanoic acid,(Z,Z)-9,12-octadecadienoic acid,(Z,Z,Z)-9,12,15-octadecatrienoic acid,and nonadecanoic acid.The tridecanoic acid,myristoleic acid,Trimethylsilyl myristic acid,(Z,Z)-7,10-hexadecanoic acid,(Z)-9-hexadecanoic acid,3,5-bis(1,1-dimethylethyl)-4-hydroxy-Benzenepropanoic acid,L-ascorbic acid 2,6-di-hexadecanoate,(Z,Z,Z)-9,12,15-octadecatrienoic acid,and 16-methyl-heptadecanoic acid were isolated and identified fromC.chinensis for the first time.It was showed that the methyl esterification method with BF_3-CH_3OH was more suitable for the fatty acid analysis in the aerial parts of C.chinensis,which was conducive to the further development and utilization of its containing unsaturated fatty acid.
Effects of two different methyl esterification methods on the results of fatty acid analysis of the aerial parts of Campylandra chinensis were examined.The fatty acid components from the aerial parts of C.chinensis were extracted by Soxhlet extractor,identified and determined based on gas chromatographymass spectrometry(GC-MS)after methyl esterification by using BF_3-CH_3OH and HCl-CH_3OH.Totally 31(BF_3-CH_3OH method)and 25(HCl-CH_3OH method)chemical constituents were measured and retrieved by GC-MS coupled with NIST2011 spectral library,including 21 kinds of fatty acid and 13 other components,the obvious content differences were dodecanoic acid,nonanedioic acid,tetradecanoic acid,hexadecanoic acid,(Z,Z)-9,12-octadecadienoic acid,(Z,Z,Z)-9,12,15-octadecatrienoic acid,and nonadecanoic acid.The tridecanoic acid,myristoleic acid,Trimethylsilyl myristic acid,(Z,Z)-7,10-hexadecanoic acid,(Z)-9-hexadecanoic acid,3,5-bis(1,1-dimethylethyl)-4-hydroxy-Benzenepropanoic acid,L-ascorbic acid 2,6-di-hexadecanoate,(Z,Z,Z)-9,12,15-octadecatrienoic acid,and 16-methyl-heptadecanoic acid were isolated and identified fromC.chinensis for the first time.It was showed that the methyl esterification method with BF_3-CH_3OH was more suitable for the fatty acid analysis in the aerial parts of C.chinensis,which was conducive to the further development and utilization of its containing unsaturated fatty acid.
引文
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[11]范亚苇,邓泽元,余永红,等.不同脂肪酸甲酯化方法对共轭亚油酸分析的影响[J].中国油脂,2007,32(1):52-55.FAN Y W,DENG Z Y,YU Y H,et al.Effect of fatty acid methyl esterification methods on analysis of conjugated linoleic acids[J].China Oils and Fats,2007,32(1):52-55.(in Chinese)
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[14]张静,周小婷,胡立盼,等.SPME-GC-MS测定不同品种牡丹花挥发性物质成分分析[J].西北林学院学报,2013,28(4):136-143.ZHANG J,ZHOU X T,HU L P,et al.SPME-GC-MS measurement of volatile on different peony varieties[J].Journal of Northwest Forestry University,2013,28(4):136-143.(in Chinese)
[15]刘帅,王爱武,李美艳,等.脂肪酸甲酯化方法的研究进展[J].中国药房,2014,25(37):3535-3537.
[16]伍新龄,王凤玲,关文强.植物油脂肪酸甲酯化方法比较与含量测定[J].食品研究与开发,2015,36(7):84-87.WU X L,WANG F L,GUAN W Q.Methods of methyl esterification and gas chromatography analysis of fatty acids in edible vegetable oil[J].Food Research and Development,2015,36(7):84-87.(in Chinese)
[17]佘珠花.气相色谱法中油脂脂肪酸衍生化方法及其选择[J].粮食加工,2004(6):64-66.SHE Z H.Oil fatty acid derivatization method and choose in gas chromatography[J].Grain Processing,2004(6):64-66.(in Chinese)
[18]张春娥,张惠,刘楚怡,等.亚油酸的研究进展[J].粮油加工,2010(5):18-21.
[19]董娟娥,马柏林,张康健,等.杜仲籽油中α-亚麻酸的含量及其生理功能[J].西北林学院学报,2002,17(2):73-75.DONG J E,MA B L,ZHANG K J,et al.Contents and active function ofα-linolenic in Eucommia ulmoides seed oil[J].Journal of Northwest Forestry University,2002,17(2):73-75.(in Chinese)
[2]中国科学院西北植物研究所编著.秦岭植物志:第3卷第1册[M].北京:科学出版社,1981:335.
[3]肖艳华.开口箭化学成分及其抗禽流感H5N1活性研究[D].北京:中国人民解放军军事医学科学院,2015.
[4]LIU C H,GUO Z Y,XUE Y H,et al.Five new furostanol saponins from the rhizomes of Tupistra chinensis[J].Fitoterapia,2012,83:323-328.
[5]宁德生,蒋丽华,刘金磊,等.开口箭根茎中甾体化合物的研究[J].天然产物研究与开发,2014(6):879-882,901.NING D S,JIANG L H,LIU J L,et al.Studies on steroids from the rhizomes of Tupistra chinensis[J].Nat.Prod.Res.Dev.,2014(6):879-882,901.(in Chinese)
[6]王慧娜,赵桦.开口箭脂肪酸成分气相色谱-质谱分析[J].中国实验方剂学杂志,2011,17(8):85-88.WANG H N,ZHAO H.Analysis fatty acid compositions of Tupistra chinensis by GC-MS[J].Chinese Journal of Experimental Traditional Medical Formulae,2011,17(8):85-88.(in Chinese)
[7]梁海东,乔有明,裴海昆,等.不同前处理分析植物脂肪酸的气相色谱-质谱法研究[J].分析科学学报,2015,31(4):525-528.LIANG H D,QIAO Y M,PEI H K,et al.Comparison of different pre-processing methods to identify fatty acids in plants by gas chromatography-mass spectrometry[J].Journal of Analytical Science,2015,31(4):525-528.(in Chinese)
[8]赵德义,张博勇,徐爱遐,等.脂肪酸在植物界中分布的研究[J].西北林学院学报,2005,20(3):147-149.ZHAO D Y,ZHANG B Y,XU A X,et al.On distribution of fatty acid in plants area[J].Journal of Northwest Forestry University,2005,20(3):147-149.(in Chinese)
[9]杨春艳,邹坤,潘家荣.开口箭挥发油成分的分析[J].三峡大学学报:自然科学版,2006,28(4):360-362.YANG C Y,ZOU K,PAN J R.Study on volatile constituents fromTupistra chinensis Bak[J].Journal of China Three Gorges University:Natural Sciences,2006,28(4):360-362.(in Chinese)
[10]孟橘,夏天文,陈勇,等.GB/T 17376-2008动植物油脂脂肪酸甲酯制备[S].北京:中国标准出版社,2008:1-22.
[11]范亚苇,邓泽元,余永红,等.不同脂肪酸甲酯化方法对共轭亚油酸分析的影响[J].中国油脂,2007,32(1):52-55.FAN Y W,DENG Z Y,YU Y H,et al.Effect of fatty acid methyl esterification methods on analysis of conjugated linoleic acids[J].China Oils and Fats,2007,32(1):52-55.(in Chinese)
[12]魏丽芳.反式脂肪酸检测方法的建立及应用[D].重庆:西南大学,2008.
[13]张白曦,宋宇航,杨芹,等.甲酯化方法对甘油三酯和游离型脂肪酸混合物脂肪酸分析的影响[J].中国粮油学报,2016,31(9):95-99.ZHANG B X,SONG Y H,YANG Q,et al.Comparison of methyl esterification methods in fatty acids determination of the mixture composed of triglycerides and free fatty acids[J].Journal of the Chinese Cereals and Oils Association,2016,31(9):95-99.(in Chinese)
[14]张静,周小婷,胡立盼,等.SPME-GC-MS测定不同品种牡丹花挥发性物质成分分析[J].西北林学院学报,2013,28(4):136-143.ZHANG J,ZHOU X T,HU L P,et al.SPME-GC-MS measurement of volatile on different peony varieties[J].Journal of Northwest Forestry University,2013,28(4):136-143.(in Chinese)
[15]刘帅,王爱武,李美艳,等.脂肪酸甲酯化方法的研究进展[J].中国药房,2014,25(37):3535-3537.
[16]伍新龄,王凤玲,关文强.植物油脂肪酸甲酯化方法比较与含量测定[J].食品研究与开发,2015,36(7):84-87.WU X L,WANG F L,GUAN W Q.Methods of methyl esterification and gas chromatography analysis of fatty acids in edible vegetable oil[J].Food Research and Development,2015,36(7):84-87.(in Chinese)
[17]佘珠花.气相色谱法中油脂脂肪酸衍生化方法及其选择[J].粮食加工,2004(6):64-66.SHE Z H.Oil fatty acid derivatization method and choose in gas chromatography[J].Grain Processing,2004(6):64-66.(in Chinese)
[18]张春娥,张惠,刘楚怡,等.亚油酸的研究进展[J].粮油加工,2010(5):18-21.
[19]董娟娥,马柏林,张康健,等.杜仲籽油中α-亚麻酸的含量及其生理功能[J].西北林学院学报,2002,17(2):73-75.DONG J E,MA B L,ZHANG K J,et al.Contents and active function ofα-linolenic in Eucommia ulmoides seed oil[J].Journal of Northwest Forestry University,2002,17(2):73-75.(in Chinese)