title: Identification and characterization of two new derivatives of chlorogenic acids in Arnica (Arnica montana L.) flowers by high-performance liquid chromatography/tandem mass spectrometry.
abstract: Arnica montana is a medicinally important plant due to its broad health effects, and it is used in Ayurvedic, Homeopathic, Unani, and folk medicines. We have used LC-MS(n) (n = 2-5) to detect and characterize in Arnica flowers 11 quantitatively minor fumaric and methoxyoxalic acid-containing chlorogenic acids, nine of them not previously reported in nature. These comprise 1,5-dicaffeoyl-3-methoxyoxaloylquinic acid, 1,3-dicaffeoyl-4-methoxyoxaloylquinic acid, 3,5-dicaffeoyl-4-methoxyoxaloylquinic acid, and 1-methoxyoxaloyl-4,5-dicaffeoylquinic acid (M(r) 602); 3-caffeoyl-4-feruloyl-5-methoxyoxaloylquinic acid and 3-feruloyl-4-methoxyoxaloyl-5-caffeoylquinic acid (M(r) 616); 1,5-dicaffeoyl-4-fumaroyl and 1,5-dicaffeoyl-3-fumaroylquinic acid (M(r) 614); 3,5-dicaffeoyl-1,4-dimethoxyoxaloylquinic acid (M(r) 688); and 1-methoxyoxaloyl-3,4,5-tricaffeoylquinic acid and 1,3,4-tricaffeoyl-5-methoxyoxaloylquinic acid (M(r) 764). All of the structures have been assigned on the basis of LC-MS(n) patterns of fragmentation, relative hydrophobicity, and analogy of fragmentation patterns if compared to caffeoylquinic acids. This is the first time when fumaric acid-containing chlorogenic acids are reported in nature.
authors.affiliation: School of Engineering and Science, Chemistry, Jacobs University Bremen, Bremen, Germany.
authors.forename: Rakesh
authors.initials: R
authors.lastname: Jaiswal
authors.forename: Nikolai
authors.initials: N
authors.lastname: Kuhnert
mesh_terms: D018650:Arnica / Q000737:chemistry*; D002726:Chlorogenic Acid / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D035264:Flowers / Q000737:chemistry*; D010936:Plant Extracts / Q000032:analysis; D053719:Tandem Mass Spectrometry / Q000379:methods*
chemical_list: D010936:Plant Extracts; D002726:Chlorogenic Acid