Identification and characterization of chlorogenic acids, chlorogenic acid glycosides and flavonoids from Lonicera henryi L. (Caprifoliaceae) leaves by LC-MSn

Phytochemistry

Volumn 108, Issue , 2014, Pages 252-263

  Jaiswal, Rakesh ^a   Müller, Heiko ^a   Müller, Anja ^a   Karar, Mohamed Gamaleldin Elsadig ^a   Kuhnert, Nikolai ^a  

^a JACOBS UNIVERSITY BREMEN   (Germany)

Author keywords

Chlorogenic acid glycosides; Chlorogenic acids; Flavonoid glycosides; LC DAD ESI MSn; Lonicera henryi L.; Polyphenols

Indexed keywords

CAPRIFOLIACEAE; LONICERA;

CHLOROGENIC ACID; FLAVONOID; GLYCOSIDE; QUINIC ACID;

ANALYSIS; BEVERAGE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; LIQUID CHROMATOGRAPHY; LONICERA; PLANT LEAF;

BEVERAGES; CHLOROGENIC ACID; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, LIQUID; FLAVONOIDS; GLYCOSIDES; LONICERA; MOLECULAR STRUCTURE; PLANT LEAVES; QUINIC ACID; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84911471373     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2014.08.023     Document Type: Article

References (51)

1. n identification and characterization of the phenolic compounds from the fruits of Flacourtia indica (Burm. F.) Merr. and Flacourtia inermis roxb Food Res. Int. 62 2014 388 396
2. Y. Chen, Y. Shan, Y.Y. Zhao, Q.Z. Wang, M. Wang, X. Feng, and J.Y. Liang Two new triterpenoid saponins from Lonicera macranthoides Chin. Chem. Lett. 23 2012 325 328
3. Y. Chen, Y. Zhao, M. Wang, H. Sun, Y. Dong, and X. Feng The first chlorogenic acid ester saponin from Lonicera macranthoides Chem. Nat. Compd. 47 2012 940 943
4. n J. Agric. Food Chem. 53 2005 3821 3832
5. n identification of chlorogenic acids J. Agric. Food Chem. 51 2003 2900 2911
6. M.N. Clifford Chlorogenic acids and other cinnamates - nature, occurrence, dietary burden, absorption and metabolism J. Sci. Food Agric. 80 2000 1033 1043
7. M.N. Clifford Chlorogenic acids and other cinnamates - nature, occurrence and dietary burden J. Sci. Food Agric. 79 1999 362 372
8. M.N. Clifford, W. Wu, J. Kirkpatrick, R. Jaiswal, and N. Kuhnert Profiling and characterization by liquid chromatography/multi-stage mass spectrometry of the chlorogenic acids in Gardeniae Fructus Rapid Commun. Mass Spectrom. 24 2010 3109 3120
9. n analysis of the cis isomers of chlorogenic acids Food Chem. 106 2008 379 385
10. n J. Agric. Food Chem. 55 2007 929 936
11. J.A. Duke, and E.S. Ayensu Medicinal Plants of China 1985 Reference Publications Algonac, Michigen
12. S. Facciola Cornucopia: A Source Book of Edible Plants 1990 Kampong Publications Vista, California
13. R. Jaiswal, M.G.E. Karar, E.A. Karar, and N. Kuhnert Identification and characterisation of the phenolics of Ilex glabra L. Gray (Aquifoliaceae) leaves by liquid chromatography tandem mass spectrometry Phytochemistry 106 2014 141 155
14. R. Jaiswal, and N. Kuhnert Identification and characterization of the phenolic glycosides of Lagenaria siceraria stand. (Bottle gourd) fruit by liquid chromatography-tandem mass spectrometry J. Agric. Food Chem. 62 2014 1261 1271
15. R. Jaiswal, L. Jayasinghe, and N. Kuhnert Identification and characterization of proanthocyanidins of 16 members of the Rhododendron genus (Ericaceae) by tandem LC-MS J. Mass Spectrom. 47 2012 502 515
16. n Phytochem. Anal. 22 2011 432 441
17. R. Jaiswal, J. Kiprotich, and N. Kuhnert Determination of the hydroxycinnamate profile of 12 members of the Asteraceae family Phytochemistry 72 2011 781 790
18. R. Jaiswal, and N. Kuhnert Identification and characterization of two new derivatives of chlorogenic acids in Arnica (Arnica montana L.) flowers by high-performance liquid chromatography/tandem mass spectrometry J. Agric. Food Chem. 59 2011 4033 4039
19. R. Jaiswal, and N. Kuhnert Identification and characterization of five new classes of chlorogenic acids in burdock (Arctium lappa L.) roots by liquid chromatography/tandem mass spectrometry Food Funct. 2 2011 63 71
20. R. Jaiswal, and N. Kuhnert How to identify and discriminate between the methyl quinates of chlorogenic acids by liquid chromatography-tandem mass spectrometry J. Mass Spectrom. 46 2011 269 281
21. R. Jaiswal, and N. Kuhnert Hierarchical scheme for liquid chromatography/multi-stage spectrometric identification of 3,4,5-triacyl chlorogenic acids in green Robusta coffee beans Rapid Commun. Mass Spectrom. 24 2010 2283 2294
22. n: identification of seven new classes of compounds J. Agric. Food Chem. 58 2010 8722 8737
23. Jaiswal, R., Karar, M.G.E., Gadir, H.A., Kuhnert, N., 2014. Identification and characterization of phenolics from Ixora coccinea L. (Rubiaceae) leaves by liquid chromatography tandem mass spectrometry. Phytochem. Anal., in press. DOI: 10.1002/pca.2530.
24. R. Jaiswal, M.F. Matei, S. Deshpande, and N. Kuhnert Identification and characterization of hydroxycinnamates of six Galium species from the Rubiaceae family K. Hostettmann, H. Stuppner, A. Marston, S. Chen, Handbook of Chemical and Biological Plant Analytical Methods 2014 John Wiley Publishers UK 505 524
25. n of the chlorogenic acids and hydroxycinnamoylshikimate esters in mate (Ilex paraguariensis) J. Agric. Food Chem. 58 2010 5471 5484
26. T. Jurikova, O. Rop, J. Mlcek, J. Sochor, S. Balla, L. Szekeres, A. Hegedusova, J. Hubalek, V. Adam, and R. Kizek Phenolic profile of edible honeysuckle berries (genus Lonicera) and their biological effects Molecules 17 2012 61 79
27. n J. Agric. Food Chem. 59 2011 10143 10150
28. Y. Kashiwada, F.A. Ahmed, S. Kurimoto, S. Kim, H. Shibata, T. Fujioka, and Y. Takaishi New α-glucosides of caffeoyl quinic acid from the leaves of Moringa oleifera Lam J. Nat. Med. 66 2012 217 221
29. A.M. Leaveau, M. Durand, and R.R. Paris The toxicity of fruits of various Lonicera Caprifoliaceae Plantes Medicinales et Phytotherapie 11 1977 94 105
30. X.Q. Li, X.H. Sun, S. Cai, X.X. Ying, and F.M. Li Investigation on the chemical constituents and variation of the flower buds of Lonicera species by UPLC-ESI-MS/MS and principle component analysis Acta Pharm. Sinic. 44 2009 895 904
31. Y. Li, J. Chen, Y. Li, and P. Li Identification and quantification of free radical scavengers in the flower buds of Lonicera species by online HPLC-DPPH assay coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry Biomed. Chromatogr. 26 2012 449 457
32. Y. Luo, L. Chen, X. Liang, H. Huang, B. Li, and L. Huang Simultaneous extraction and isolation of chlorogenic acid and flavonoids from leaves and rattan of Lonicera japonica Jishou Daxue Xuebao (Ziran Kexue Ban) 32 2011 91 94
33. C. Ma, K. Dastmalchi, B.D. Whitaker, and E.J. Kennelly Two new antioxidant malonated caffeoylquinic acid isomers in fruits of wild eggplant relatives J. Agric. Food Chem. 59 2011 9645 9651
34. C. Ma, B.D. Whitaker, and E.J. Kennelly New 5-O-caffeoylquinic acid derivatives in fruit of the wild eggplant relative Solanum viarum J. Agric. Food Chem. 58 2010 11036 11045
35. R.E. March, E.G. Lewars, C.J. Stadey, X.S. Miao, X.M. Zhao, and C.D. Metcalfe A comparison of flavonoid glycosides by electrospray tandem mass spectrometry Int. J. Mass Spectrom. 248 2006 61 85
36. M.F. Matei, R. Jaiswal, and N. Kuhnert Investigating the chemical changes of chlorogenic acids during coffee brewing: conjugate addition of water to the olefinic moiety of chlorogenic acids and their quinides J. Agric. Food Chem. 60 2012 12105 12115
37. B. McDougall, P.J. King, B.W. Wu, Z. Hostomsky, M.G. Reinecke, and W.E. Robinson Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase Antimicrob. Agents Chemother. 42 1998 140 146
38. C.E. McNamara, N.B. Perry, J.M. Follett, G.A. Parmenter, and J.A. Douglas A new glucosyl feruloyl quinic acid as a potential marker for roots and rhizomes of goldenseal, Hydrastis canadensis J. Nat. Prod. 67 2004 1818 1822
39. F. Nikhat, D. Satynarayanaa, and A.B. Joshia Phytochemical and pharmacological investigation of roots of Syzygium cuminii (L.) skeel Asian J. Research Chem. 1 2008 22 26
40. n Phytochemistry 72 2011 2376 2384
41. A. Rajavelu, Z. Tulyasheva, R. Jaiswal, A. Jeltsch, and N. Kuhnert The inhibition of the mammalian DNA methyltransferase 3a (Dnmt3a) by dietary black tea and coffee polyphenols BMC Biochem. 12 2011 1 8
42. W.E. Robinson, M. Cordeiro, S. AbdelMalek, Q. Jia, S.A. Chow, M.G. Reinecke, and W.M. Mitchell Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase Mol. Pharmacol. 50 1996 846 855
43. J. Shearer, A. Farah, T. de Paulis, D.P. Bracy, R.R. Pencek, T.E. Graham, and D.H. Wasserman Quinides of roasted coffee enhance insulin action in conscious rats J. Nutr. 133 2003 3529 3532
44. J. Slanina, H. Paulova, O. Humpa, H. Bochorakova, and E. Taborska 1,5-Dicaffeoylquinic acid, an antioxidant component of Cynara cardunculus leaves Scr. Med. (Brno) 72 1999 9 18
45. H.F. Stich, M.P. Rosin, and L. Bryson Inhibition of mutagenicity of a model nitrosation reaction by naturally-occurring phenolics, coffee and tea Mutat. Res. 95 1982 119 128
46. M. Sun, X. Feng, M. Yin, Y. Chen, X. Zhao, and Y. Dong A biflavonoid from stems and leaves of Lonicera macranthoides Chem. Nat. Compd. 48 2012 231 233
47. C. Tanaka Tanaka's Cyclopedia of Edible Plants of the World 1976 Keigaku Publishing Co. Tokyo
48. P.T. Thuong, N.D. Su, T.M. Ngoc, T.M. Hung, N.H. Dang, N.D. Thuan, K. Bae, and W.K. Oh Antioxidant activity and principles of Vietnam bitter tea Ilex kudingcha Food Chem. 113 2009 139 145
49. A. Trute, J. Gross, E. Mutschler, and A. Nahrstedt In vitro antispasmodic compounds of the dry extract obtained from Hedera helix Planta Med. 63 1997 125 129
50. n Yao Xue Xue Bao. 43 2008 185 190
51. n Talanta 104 2013 1 9