Analysis and Identification of Chemical Constituents of Fenugreek by UPLC-IT-MSn and UPLC-Q-TOF-MS

doi:10.1007/s40242-017-7136-4

Abstract

Abstract:

Fenugreek, a traditional Chinese medical plant, has been widely used as food ingredients because of its outstanding medicinal qualities. The hypoglycemic activity of fenugreek is one of its important pharmacological properties. Both of saponin and flavonoid components have the hypoglycemic activity and their contents in fenugreek are 4%-8% and 1%-2%, respectively. This paper focused on these two types of components to carry out purification research and chemical analysis. The heating reflux extraction method and macroporous resin purification method were designed to prepare the saponins and the flavonoids components from defatted fenugreek seeds. Petroleum ether ultrasonic skim and 70% ethanol refluxing were used for the extraction of saponins and flavonoid from fenugreek. The column of DM130 macroporous resin and D101 macroporous resin were respectively used to prepare fenugreek saponin and flavonoid components, and the total contents of them were 78.56% and 62.28%, respectively. The saponin and flavonoids were subsequently analyzed by an ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry(UPLC-Q-TOF-MS) along with an ultra-performance liquid chromatography and ion-trap tandem mass spectrometry(UPLC-IT-Mⁿ). As a result, 57 saponins and 19 flavonoid compounds were characterized. The obtained results will provide a theory basis for further research on fenugreek, as well as research and development of hypoglycemic new drugs.

Key words: Fenugreek, Flavonoid, Saponin, Ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry(UPLC-Q-TOF-MS), Ultra-performance liquid chromatography ion-trap tandem mass spectrometry(UPLC-IT-MSⁿ)

WANG Jiaqi, JIANG Wenyue, LIU Zhongying, WANG Junhua, FU Tianyue, WANG Yongsheng. Analysis and Identification of Chemical Constituents of Fenugreek by UPLC-IT-MSⁿ and UPLC-Q-TOF-MS[J]. Chemical Research in Chinese Universities, 2017, 33(5): 721-730.

References

[1] Haghani K., Bakhtiyari S., Doost M. J., Can. J. Diabetes, 2016, 40, 135
[2] Sharma M. S., Choudhary P. R., J. Diet. Suppl., 2016, 14, 1
[3] Acharya S. N., Acharya K., Paul S., Basu S. K., Can. J. Plant Sci., 2017, 91, 99
[4] Rahmati-Yamchi M., Ghareghomi S., Haddadchi G., Milani M., Aghazadeh M., Daroushnejad H., Mol. Biol. Rep., 2014, 41, 6247
[5] Sharma N., Suresh S., Debnath A., Jha S., Front Biosci., 2017, 9, 246
[6] Prema A., Thenmozhi A. J., Manivasagam T., Essa M. M., Akbar M. D., Akbar M., PLoS One, 2016, 11, e0165955
[7] Pang X., Kang L., Yu H., Zhao Y., Xiong C., Zhang J., Shan J., Ma B., J. Sep. Sci., 2012, 35, 1538
[8] Kang L. P., Zhao Y., Pang X., Yu H. S., Xiong C. Q., Zhang J., Gao Y., Yu K., Liu C., Ma B. P., J. Pharm. Biomed. Anal., 2013, 74, 257
[9] Yoshikawa M., Murakami T., Komatsu H., Murakami N., Yamahara J., Matsuda H., Chem. Pharm. Bull., 1997, 45, 81
[10] Yoshikawa M., Murakami T., Komatsu H., Yamahara J., Matsuda H., Heterocycles, 1998, 47, 397
[11] Murakami T., Kishi A., Matsuda H., Yoshikawa M., Chem. Pharm. Bull., 2000, 48, 994
[12] Xu X. M., Wang J., Yang H., Huang W. P., Yuan C. J., Chin. Tradit. Herbal. Drugs, 2005, 6, 1
[13] Benayad Z., Gómez-Cordovés C., Es-Safi N. E., Int. J. Mol. Sci., 2014, 15, 20668
[14] Benayad Z., Gómez-Cordovés C., Es-Safi N. E., J. Food. Compos. Anal., 2014, 35, 21
[15] Król-Kogus B., G?ód D., Krauze-Baranowska M., Mat?awska I., J. Chromatogr. A, 2014, 1367, 48
[16] Rayyan S., Fossen T., Andersen M., J. Agric. Food Chem., 2010, 58, 7211
[17] Hamden K., Jaouadi B., Salami T., Carreau S., Bejar S., Elfeki A., Biotechnol. Bioproc. E, 2010, 15, 745
[18] Gad M. Z., El-Sawalhi M. M., Ismail M. F., El-Tanbouly N. D., Mol. Cell Biochem., 2006, 281, 173
[19] Al-Habori M., Raman A., Lawrence M. J., Skett P., Int. J. Exp. Diabetes. Res., 2001, 2, 91
[20] Shan J. J., Ren J. W., Wu C. M., Zhao Y. M., J. Chin. Phar. Sci., 2008, 43, 1457
[21] Wang H. Q., Guo S., Qian D. W., Qian Y. F., Duan J. A., J. Pharm. Biomed. Anal., 2012, 67/68, 16
[22] Tan G., Zhu Z., Jing J., Lv L., Lou Z., Zhang G. Y., Chai. Biomed. Chromatogr., 2011, 25, 913
[23] Dartora N., de Souza L. M., Santana A. P., Iacomini M., Valduga A. T., Gorin, P. A. J., Sassaki G. L., Food Chem., 2011, 129, 1453
[24] Guillarme D., Schappler J., Rudaz S., Veuthey J. L., Trends. Anal. Chem., 2010, 29, 15
[25] Theodoridis G. A., Gika H. G., Want E. J., Wilson I. D., Anal. Chim. Acta, 2012, 711, 7

Analysis and Identification of Chemical Constituents of Fenugreek by UPLC-IT-MSⁿ and UPLC-Q-TOF-MS

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Kingsadingthongkham VONGDETH, RAN Liqiong, YAN Lili, WANG Qiuan. Synthesis and Activity Evaluation of Novel Prenylated Flavonoids as Antiproliferative Agents [J]. Chemical Research in Chinese Universities, 2018, 34(4): 564-570.
[2]	YAO Hua, WANG Tong, WU Qian, LIU Ying, LI Peng, LI Xuwen, JIN Yongri. Studies on New Steroidal Saponins from Allii macrostemonis Bulbus and Their Antitumor Activities [J]. Chemical Research in Chinese Universities, 2018, 34(1): 61-66.
[3]	CUI Xueqin, MA Zhongxiao, BAI Lu, WU Yong, GUO Sen, LIU Qingchao, ZHANG Li, HO Chi-Tang, BAI Naisheng. Phytochemical Analysis of Ziziphus jujuba Leaves in Six Cultivars at the Whole Life Stage by High Performance Liquid Chromatography [J]. Chemical Research in Chinese Universities, 2017, 33(5): 702-708.
[4]	HE Yangfang, LIU Wenlong, SU Rui, XIU Yang, PEI Jin. Detection of Saponins and Oligosaccharides in Herbs Using Direct Analysis in Real-time Mass Spectrometry [J]. Chemical Research in Chinese Universities, 2017, 33(2): 172-178.
[5]	YANG Jie, YU Xue, CAI Xiaoxiang, CHEN Yanxin, ZANG Huiming, LI Xuwen, JIN Yongri. Semisynthesis and Cytotoxicity Evaluation of a Series of Ocotillol Type Saponins and Aglycones from 20(S)-Ginsenoside Rg₂, Rh₁, Protopanaxatriol and Their 20(R)-Epimers [J]. Chemical Research in Chinese Universities, 2016, 32(1): 35-40.
[6]	WANG Hui, WANG Jiayuan, WU Xiaopeng, SHEN Haiyan, LUO Ying, DAI Haofu, MEI Wenli. HPLC-ESI-MS Analysis of Flavonoids Obtained from Tissue Culture of Dracaena cambodiana [J]. Chemical Research in Chinese Universities, 2015, 31(1): 38-43.
[7]	REN Li, LIU Yang, YU Guihua, GAO Yuan, LIU Xin, WANG Bo, DENG Xiaonan, CHENG Maosheng. Synthesis and Tumor Cytotoxicity of Novel N-Substituted Glucosamine-bearing Oleanolic Acid Derivatives [J]. Chemical Research in Chinese Universities, 2014, 30(4): 639-643.
[8]	YAO Hua, JIN Yong-ri, SHAN Jing, WANG Xiao-zhong, ZHANG Mu-chun, LI Xu-wen. Two New Natural Methoxyflavonoids from Leaves of Murraya paniculata(L.) Jack [J]. Chemical Research in Chinese Universities, 2013, 29(5): 884-887.
[9]	WANG Qing-hu, AO Wu-li-ji, DAI Na-yin-tai. Structural Elucidation and HPLC Analysis of Six Flavone Glycosides from Artemisia frigida Willd. [J]. Chemical Research in Chinese Universities, 2013, 29(3): 439-444.
[10]	HUANG Chu-sheng, SHI Jian-cheng, LIU Hong-xing, CHEN Qian, DUAN Hong-xia. Facile Syntheses of 3-Isopentenyl Flavone and 3-Geranyl Flavone [J]. Chemical Research in Chinese Universities, 2012, 28(6): 994-998.
[11]	CAI Shuang-lian, LIU Shuang, LIU Li, WANG Qiu-an . Synthesis of Bioactive Natural Polymethoxyflavones and Their Vinyl Ether Derivatives [J]. Chemical Research in Chinese Universities, 2012, 28(4): 631-636.
[12]	ZHANG Yu-feng, ZHAO Qin-qin, SHAO Qin and FAN Xiao-hui*. Simultaneous Determination of Two Types of Active Components with Different Physicochemical Properties in Kushen by HPLC-UV [J]. Chemical Research in Chinese Universities, 2011, 27(3): 375-379.
[13]	SONG Ping, YANG Xin-zhou and YU Jun. New Chemical Compound from Caragana jubata* (pall.) Poir. [J]. Chemical Research in Chinese Universities, 2010, 26(4): 563-566.
[14]	XU Ya-juan, XU Tun-hai, XIE Sheng-xu, SI Yun-shan and XU Dong-ming. Two New Furostanol Saponins from Tribulus Terrestris* L. [J]. Chemical Research in Chinese Universities, 2010, 26(1): 46-49.
[15]	LIU Gui-ying, ZHOU Hong-yu, LU Juan, ZHU Na, GUI Ming-yu, JIN Yong-ri, ....... Determination of Saponins in Leaf of Panax Ginseng C. A. Mey. by High Performance Liquid Chromatography [J]. Chemical Research in Chinese Universities, 2009, 25(3): 297-301.