Rapid characterization of 96 chemical constituents in Citri Reticulatae Folium (leaves of ‘Fuju’) using HPLC-DAD-ESI-MSn

doi:10.5246/jcps.2016.02.010

Abstract

Abstract:

In order to systematically investigate the chemical constituents of Citri Reticulatae Folium (leaves of ‘Fuju’), an analytical method that included high-performance liquid chromatography, diode array detection, electrospray ionization, and ion-trap time-of-flight mass spectrometry (HPLC-DAD-ESI-MSⁿ) was used to separate and identify the individual chemical components of Citri Reticulatae Folium. As a result, 96 compounds were tentatively identified in this study: including 31 phenolic acids, 4 flavonoid aglycones, 6 flavonoid mono-O-glycosides, 10 flavonoid-O-diglycosides, 5 flavonoid mono-C-glycosides, 5 flavonoid di-C-glycosides, 6 flavonoid O,C-glycosides, 5 (3-hydroxy-3-methylglutaryl) glycosyl flavonoids, 1 flavan-3-ol,and 2 alkaloids. In addition, 21 polymethoxy flavonoids (PMFs) were identified in this paper. Among these compounds, 52 compounds, which were previouslyfound in other Citrus plants, have been identified for the first time in Citri Reticulatae Folium. 15 compounds have not been previously found in theCitrusgenus were identified. Moreover, 9 potentially new compounds have also been detected in this paper. This is the first report of the full characterization of chemical components of Citri Reticulatae Folium (leaves of ‘Fuju’) by HPLC-DAD-ESI-MSⁿ.

Key words: Citri Reticulatae Folium (leaves of ‘Fuju’), HPLC-DAD-ESI-MSn, Flavonoid, O,C-Glycosides, PMFs

CLC Number:

R284

Supporting:

Guihua Cao, Qingrong Fu, Cangman Zhang, Hong Wang, Shizhong Chen. Rapid characterization of 96 chemical constituents in Citri Reticulatae Folium (leaves of ‘Fuju’) using HPLC-DAD-ESI-MSn[J]. Journal of Chinese Pharmaceutical Sciences, 2016, 25(2): 91-110.

References

[1] Roowi, S.; Crozier, A. J. Agric. Food Chem. , 59, 12217-12225.2011

[2] Tripoli, E.; Guardia, M.L.; Giammanco, S.; Majo, D.D.; Giammanco, M. Food Chem. , 104, 466-479.2007

[3] Khan, M.K.; Huma, Z.E.; Dangles, O. J. Food Compos. Anal. , 33, 85-104.2014

[4] Duan, L.; Guo, L.; Liu, K.; Liu, E.H.; Li, P. J. Chromatogr. A. , 1339, 118-127.2014

[5] He, X.G.; Lian, L.Z.; Lin, L.Z.; Bernart, M.W. J. Chromatogr. A. 1997, 791, 127-134.

[6] Bocco, A.; Cuvelier, M.E.; Richard, H.; Berset, C. J. Agric. Food Chem. 1998, 46, 2123-2129.

[7] Jeong, S.M.; Kim, S.Y. J. Agric. Food Chem. 2004, 52, 3389-3393.

[8] Manthey, J.A.; Grohmann, K. J. Agric. Food Chem. 2001, 49, 3268-3273.

[9] Stuetz, W.; Prapamontol, T. J. Agric. Food Chem. 2010, 58, 6069-6074.

[10] Barreca, D.; Bisignano, C; Ginestra, G. Food Chem. 2013, 141, 1481-1488.

[11] Zhang, J.Y.; Zhang, Q.; Zhang, H.X. J. Agric. Food Chem. 2012, 60, 9023-9034.

[12] Xiao, H.; Yang, C.S.; Li, S.; Jin, H.; Ho, C.T.; Patel, T. Mol. Nutr. Food Res. 2009, 53, 398-406.

[13] Nakagawa, H.; Takaishi, Y.; Tanaka, N. J. Nat. Prod. 2006, 69, 1177-1179.

[14] Zheng, G.D.; Zhou, P.; Yang, H.; Li, Y.S.; Li, P.; Liu, E.H. Food Chem. 2013, 136, 604-611.

[15] Ding, L.; Luo, X.B.; Tang, F.; Yuan, J.B.; Liu, Q.; Yao, S.Z. J. Chromatogr. B. 2007, 857, 202-209.

[16] Wang, S.F.; Chen, P.H.; Jiang, W.; Wu, L.H.; Chen, L.L. J. Chromatogr. A. 2014, 1348, 105-124.

[17] Kawaii, S.; Tomono, Y.; Katase, E. J. Agric. Food Chem. 2000, 48, 3865-3871.

[18] Manthey, J.A.; Grohmann, K.; Berhow, M.A.; Tisserat, B. Plant Physiol. Biochem. 2000, 38, 333-343.

[19] Chen, J.; Montanari, A.M. J. Agric. Food Chem. 1998, 46, 1235-1238.

[20] Lin, L.Z.; Harnly, J.M. J. Agric. Food Chem. 2007, 55, 1084-1096.

[21] Bengoechea, L.; Hernandez, T.; Quesada, C. Chromatographia. 1995, 41, 94-98.

[22] Lorenz, P.; Conrad, J.; Bertrams, J. Phytochem. Anal. 2012, 23, 60-71.

[23] Duenas, M.; Fernandez, D.; Hernandez, T.; Estrella, I.; Munoz, R. J. Sci. Food Agric. 2005, 85, 297-304.

[24] Risch, B.; Herrmann, K.; Wray, V.; Grotjahn, L. Phytochemistry. 1987, 26, 509-510.

[25] Zhao, H.Y.; Fan, M.X.; Wu, X.; Wang, H.J.; Yang, J.; Si, N.; Bian, B.L. J. Chromatogr. Sci. 2013, 51, 273-285.

[26] Jaiswal, R.; Kuhnert, N. J. Agric. Food Chem. 2014, 62, 1261-1271.

[27] Abrosca, B.D.; Fiorentino, A.; Ricci, A.; Scognamiglio, M. Phytochem. Lett. 2010, 3, 38-44.

[28] Pacifico, S.; Gallicchio, M.; Lorenz, P. Chem. Res. Toxicol. 2014, 27, 611-626.

[29] Zhao, X.; Long, Z.M.; Dai, J.N.; Bi, K.S.; Chen, X.H. Rapid Commun. Mass Spectrom. 2012, 26, 2443-2453.

[30] Seo, O.N.; Kim, G.S.; Kim, Y.H. J. Funct. Foods. 2013, 5, 1741-1750.

[31] Clifford, M.N.; Johnston, K.L.; Knight, S.; Kuhnert, N. J. Agric. Food Chem. 2003, 51, 2900-2911.

[32] Vilaplana, A.G.; Valentao, P.; Moreno, D.A. J. Agric. Food Chem. 2012, 60, 6571-6580.

[33] Kuhnert, N.; Jaiswal, R.; Matei, M.F.; Sovdat, T.; Deshpande, S. Rapid Commun. Mass Spectrom. 2010, 24, 1575-1582.

[34] Parveen, I.; Threadgill, M.D.; Hauck, B.; Donnison, I.; Winters, A. Phytochemistry. 2011, 72, 2376-2384.

[35] Arroyo, S.F.; Catalan, E.B.; Micol, V.; Carretero, A.S.; Gutierrez, A.F. Phytochem. Anal. 2010, 21, 307-313.

[36] Hvattum, E.; Ekeberg, D. J. Mass Spectrom. 2003, 38, 43-49.

[37] Cuyckens, F.; Rozenberg, R.; Hoffmann, E.; Claeys, M. J. Mass Spectrom. 2001, 36, 1203-1210.

[38] March, R.; Lewars, E.G.; Stadey, C.J.; Miao, X.S.; Zhao, X.M.; Metcalfe, C.D. Int. J. Mass Spectrom. 2006, 248, 61-85.

[39] Cuyckens, F.; Claeys, M. Phytochem. Anal. 2001, 12, 159-165.

[40] Voirin, B. Phytochemistry. 1984, 23, 2237-2251.

[41] Voirin, B. Phytochemistry. 1983, 22, 2107-2145.

[42] Mandalari, G.; Bennett, R.N.; Bisiganno, G. J. Agric. Food Chem. 2006, 54, 197-203.

[43] Garcia, B.A.; Berrueta, L.A.; Lobato, S.G.; Urkaregi, A.; Gallo, B.; Vicente, F. J. Agric. Food Chem. 2012, 60, 3635-3644.

[44] Dugo, P.; Presti, M.L.; Ohman, M. J. Sep. Sci. 2005, 28, 1149-1156.

[45] Kim, G.O.; Han, J.H.; Ko, G.H. Repub. Korean Kongkae Taeho Kongbo KR 2009081287 A 20090728, 2009.

[46] Wang, Z.D.; Shang, Q.K.; Wang, W.L.; Feng, X.J. J. Food Process Eng. 2011, 34, 844-859.

[47] Kuroyanagi, M.; Ishii, H.; Kawahara, N. J. Nat. Med. 2008, 62, 107-111.

[48] Garcia, B.A.; Lobato, S.G.; Berrueta, L.A.; Gallo, B.; Vicente, F. Talanta. 2012, 99, 213-224.

[49] Ferreres, F.; Izquierdo, A.G.; Andrade, P.B.; Valentao, P.; Barberan, F.A.T. J. Chromatogr. A. 2007, 1161, 214-223.

[50] Ferreres, F.; Izquierdo, A.G.; Vinholes, J. Rapid Commun. Mass Spectrom. 2011, 25, 700-712.

[51] Jhoo, J.W.; Ang, C.Y.W.; Heinze, T.M. J. Food Sci. 2007, 72, 120-125.

[52] Anagnostopoulou, M.A.; Kefalas, P. Biomed. Chromatogr. 2012. 26, 1252-1268.

[53] Piccinelli, A.L.; Mesa, M.G. J. Agric. Food Chem. 2008, 56, 1574-1581.

[54] Reidah, I.M.A.; Contreras, M.D.M.; Roman, D.A. Electrophoresis. 2014, 35, 1571-1581.

[55] Anagnostopoulou, M.A.; Kefalas, P.; Kokkalou, E. Biomed. Chromatogr. 2005, 19, 138-148.

[56] Wu, L.Z.; Zhang, X.P.; Xu, X.D.; Zheng, Q.X.; Yang, J.S.; Ding, W.L. J. Pharm. Biomed. Anal. 2013, 75, 55-63.

[57] Mastubara, Y.; Sawabe, A.; Mizuno, T. Kinki Daigaku Igaku Zasshi. 1987, 12, 89-101.

[58] Matsubara, Y.; Kumamoto, H. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu. 1985, 27, 702-709.

[59] Hou, B.; Li, Z.L.; Li, X. Acta Pharm. Sin. 2005, 40, 533-535.

[60] Liu, G.Q.; Dong, J.; Wang, H. Chem. J. Chinese U. 2009, 30, 1566-1570.

[61] Ferracin, R.J. Phytochemistry. 1998, 47, 393-396.

[62] Ribeiro, A.B.; Abdelnur, P.V. J. Agric. Food Chem. 2008, 56, 7815-7822.

[63] Chen, H.F.; Zhang, W.G.; Yuan, J.B. J. Pharm. Biomed. Anal. 2012, 59, 90-95.

[64] Nielsen, S.; Breinholt, V.; Cornett, C.; Dragsted, L.O. Food Chem. Toxicol. 2000, 38, 739-746.

[65] Sugiyama, S.; Umehara, K.; Kuroyanagi, M.; Ueno, A.; Taki, T. Chem. Pharm. Bull. 1993, 41, 714-719.

[66] Haggag, E.G.; Mahmoud, I.I.; Abou, M.E.A.; Mabry, T.J. Asian J. Chem. 1999, 11, 707-714.

[67] Hyon, J.S.; Kang, S.M.; Han, S.W. Hanˊguk Sikpˊum Yongyang Kwahak Hoechi. 2009, 38, 1310-1316.

[68] Wollenweber, E.; Roitman, J.N. Biochem. Syst. Ecol. 1996, 24, 479-480.

[69] Lichius, J.J.; Thoison, O.; Montagnac, A. J. Nat. Prod. 1994, 57, 1012-1016.

[70] Horie, T.; Tsukayama, M.; Nakayama, M. Bull. Chem. Soc. Jpn. 1982, 55, 2928-2932.

[71] Lin, Z.T.; Wang, H.; Xu, Y.; Dong, J. Food Chemistry. 2012, 134, 1181-1191.