Mass spectrometry of 1,3- and 1,5-dicaffeoylquinic acids

Journal of Mass Spectrometry

Volumn 39, Issue 4, 2004, Pages 384-395

  Schram, Karl ^a   Miketova, Petra ^a   Slanina, Jiri ^b   Humpa, Otakar ^b   Taborska, Eva ^b  

^a UNIVERSITY OF ARIZONA   (United States)

^b MASARYK UNIVERSITY   (Czech Republic)

Author keywords

Dicaffeoylquinic acids; Electrospray ionization; Natural products; Tandem mass spectrometry

Indexed keywords

DERIVATIVES; IONIZATION; IONS; ISOMERS; ORGANIC ACIDS; SAMPLING; SPECTRUM ANALYSIS;

ELECTROSPRAY IONIZATION; ION ABUNDANCES; SPECIFIC IONS; TANDEM MASS SPECTROMETRY;

MASS SPECTROMETRY;

ACETIC ACID DERIVATIVE; CYNARINE; PROTON;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; FRAGMENTATION REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTERMETHOD COMPARISON; ISOMERISM; NEGATIVE ION ELECTROSPRAY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITIVE ION ELECTROSPRAY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TANDEM MASS SPECTROMETRY;

CINNAMATES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR CONFORMATION; QUINIC ACID; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 1942516860     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/jms.600     Document Type: Article

References (13)

1. Chuda Y, Ono M, Ohnishi-Kameyama M, Nagata T, Tsushida T. Structural identification of two antioxidant quinic acid derivatives from garland (Chrysanthemum coronarium L). J. Agric. Food Chem. 1996; 44: 2037.
2. Baset P, Natsushige K, Kodata S, Namba T. Four di-O-caffeoyl quinic acid derivatives from propolis. Potent hepatoprotective activity in experimental liver injury models. Biol. Pharm. Bull. 1996; 19: 1479.
3. Scholz E, Heinrich M, Hunkler D. Caffeoylquinic acids and some biological activities of Pluchea symphytifolia. Planta Med. 1994; 60: 360.
4. Kimura Y, Okuda T, Hatano T, Agata I. Studies on the activities of tannins and related compounds from medicinal plants and drugs. 6. Inhibitory effects of caffeoylquinic acids on histamine-release from rat peritoneal mast cells. Chem Pharm. Bull. 1985; 33: 690.
5. Slanina J, Paulova H, Humpa O, Bochorakova H, Taborska E. 1,5-Dicaffeoylquinic acid, and antioxidant component of Cynara cardunculus leaves. Scr. Med. (Brno) 1999; 72: 9.
6. Robinson WE, Reinecke M, Gbdel-Malek S, Jia Q, Chow S. Inhibitors of HIV-1 replication that inhibit HIV integrase. Proc. Natl. Acad. Sci. USA 1996; 93: 6326.
7. King P, Ma G, Miao W, Jia Q, McDougall B, Reinecke M, Cornell C, Kuan J, Kim T, Robinson WE. Structure-activity relationships: Analogues of the Dicaffeoylquinic and dicaffenyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication. J. Med. Chem. 1999; 42: 497.
8. Slanina J, Taborska E, Bochorakova H, Slaninova I, Humpa O, Robinson WE, Schram K. New and facile method of preparation of the anti-HIV-1 agent, 1,3-dicaffeoylquinic acid. Tetrahedron Lett. 2001; 42: 3383.
9. Miketova P, Schram K, Whitney J, Kearns E, Timmermann B. Mass spectrometry of 3,5- and 4,5-dicaffeolyquinic acids and selected derivatives. J. Mass Spectrom. 1999; 34: 1240.
10. Timmermann B, Hoffmann J, Jolad S, Schram K, Klenck R, Bates R. Constituents of Chrysothamnus paniculatus 3-3,4,5-tricaffeoylquinic acid (a new shikimate prearomatic) and 3,4-dicaffeoylquinic 3,5-dicaffeoylquinic and 4,5-dicaffeolyquinic acids. J. Nat. Prod. 1983; 46: 365.
11. Panzizzi L, Scarpati ML. Nature 1954; 174: 1062.
12. Corse J, Lundin RE, Sondheimer E, Waiss AC. Conformational analysis of D-(-)-quinic acid and some of its derivatives by nuclear magnetic resonance. Phytochemistry 1966; 5: 767.
13. Pauli GF, Poetsch F, Nahrstedt A. Structure assignment of natural quinic acid derivatives using proton nuclear magnetic resonance techniques. Phytochem. Anal. 1998; 9: 177.