Identification and quantification of coumarins in Peucedanum ostruthium (L.) Koch by HPLC-DAD and HPLC-DAD-MS

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 9, 2011, Pages 4371-4377

  Vogl, Sylvia ^a   Zehl, Martin ^a   Picker, Paolo ^a   Urban, Ernst ^a   Wawrosch, Christoph ^a   Reznicek, Gottfried ^a   Saukel, Johannes ^a   Kopp, Brigitte ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Coumarins; HPLC DAD MS; Imperatorin; Isoimperatorin; Osthole; Ostruthin; Ostruthol; Oxypeucedanin; Oxypeucedanin hydrate; Peucedanum ostruthium; Quantification; Validation

Indexed keywords

COUMARINS; HPLC-DAD-MS; IMPERATORIN; ISOIMPERATORIN; OSTHOLE; OSTRUTHIN; OSTRUTHOL; OXYPEUCEDANIN; OXYPEUCEDANIN HYDRATE; PEUCEDANUM OSTRUTHIUM; QUANTIFICATION; VALIDATION;

ACETIC ACID; ACETONITRILE; CHROMATOGRAPHY; HYDRATES; HYDRATION; MASS SPECTROMETRY;

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

COUMARIN DERIVATIVE; PLANT EXTRACT;

APIALES; ARTICLE; CHEMISTRY; EVALUATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INSTRUMENTATION; MASS SPECTROMETRY; METHODOLOGY;

APIACEAE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COUMARINS; MASS SPECTROMETRY; PLANT EXTRACTS;

PEUCEDANUM OSTRUTHIUM;

EID: 79955676115     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf104772x     Document Type: Article

References (34)

1. Gerlach, S.; Saukel, J.; Kubelka,W. Pflanzen in der österreichischen Volksmedizin. Die,VOLKSMED-Datenbank". Sci. Pharm. 2006, 74, S36.
2. Hadacek, F.; Muller, C.; Werner, A.; Greger, H.; Proksch, P. Analysis, isolation and insecticidal activity of linear furanocoumarins and other coumarin derivatives from Peucedanum (Apiaceae: Apioideae). J. Chem. Ecol. 1994, 20, 2035-2054. (Pubitemid 2148204)
3. Curini, M.; Cravotto, G.; Epifano, F.; Giannone, G. Chemistry and biological activity of natural and synthetic prenyloxycoumarins. Curr. Med. Chem. 2006, 13, 199-222.
4. Ganzera, M.; Sturm, S.; Stuppner, H. HPLC-MS and MECC analysis of coumarins. Chromatographia 1997, 46, 197-203. (Pubitemid 27351385)
5. Thuong, P. T.; Hung, T. M.; Ngoc, T. M.; Ha, D. T.; Min, B. S.; Kwack, S. J.; Kang, T. S.; Choi, J. S.; Bae, K. Antioxidant activities of coumarins from Korean medicinal plants and their structure-activity relationships. Phytother. Res. 2010, 24, 101-106.
6. Schinkovitz, A.; Gibbons, S.; Stavri, M.; Cocksedge, M. J.; Bucar, F. Ostruthin: An antimycobacterial coumarin from the roots of Peucedanum ostruthium. Planta Med. 2003, 69, 369-371. (Pubitemid 36578006)
7. Garcia-Argaez, A. N.; Ramirez Apan, T. O.; Parra Delgado, H.; Velazquez, G.; Martinez-Vazquez, M. Anti-inflammatory activity of coumarins from Decatropis bicolor on TPA ear mice model. Planta Med. 2000, 66, 279-281. (Pubitemid 30235594)
8. Genovese, S.; Curini, M.; Epifano, F. Prenyloxyphenylpropanoids as a novel class of anti-inflammatory agents. Antiinflamm. Antiallergy Agents Med. Chem. 2010, 9, 158-165.
9. Riveiro,M. E.; De Kimpe, N.;Moglioni, A.; Vazquez, R.; Monczor, F.; Shayo, C.; Davio, C. Coumarins: old compounds with novel promising therapeutic perspectives. Curr. Med. Chem. 2010, 17, 1325-1338.
10. Urbain, A.; Marston, A.; Hostettmann, K. Coumarins from Peucedanum ostruthium as inhibitors of acetylcholinesterase. Pharm. Biol. 2005, 43, 647-650. (Pubitemid 43062358)
11. Abraham, K.; Wohrlin, F.; Lindtner, O.; Heinemeyer, G.; Lampen, A. Toxicology and risk assessment of coumarin: Focus on human data. Mol. Nutr. Food Res. 2010, 54, 228-239.
12. da Silva, V. B.; Kawano, D. F.; Carvalho, I.; da Conceicao, E. C.; de Freitas, O.; da Silva, C. H. T. P. Psoralen and bergapten: in silico metabolism and toxicophoric analysis of drugs used to treat vitiligo. J. Pharm. Pharm. Sci. 2009, 12, 378-387.
13. McKenna, K. E. Iatrogenic skin cancer: induction by psoralen/ ultraviolet A and immunosuppression of organ transplant recipients. Photodermatol. Photoimmunol. Photomed. 2004, 20, 289-296. (Pubitemid 39562147)
14. Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contacts with Food (AFC) on a request from the Commission related to coumarin (question number EFSA-Q-2003-118). EFSA J. 2004, 104, 1-36 (available at http://www.efsa.europa.eu/en/efsajournal/pub/104.htm).
15. Woehrlin, F.; Fry, H.; Abraham, K.; Preiss-Weigert, A. Quantification of flavoring constituents in cinnamon: high variation of coumarin in cassia bark from the German retail market and in authentic samples from Indonesia. J. Agric. Food Chem. 2010, 58, 10568-10575.
16. Segal, R.; Pilote, L. Warfarin interaction with Matricaria chamomilla. Can. Med. Assoc. J. 2006, 174, 1281-1282.
17. Dugo, P.; Piperno, A.; Romeo, R.; Cambria, M.; Russo, M.; Carnovale, C.; Mondello, L. Determination of oxygen heterocyclic components in citrus products by HPLC with UV detection. J. Agric. Food Chem. 2009, 57, 6543-6551.
18. Park, A. Y.; Park, S. Y.; Lee, J.; Jung, M.; Kim, J.; Kang, S. S.; Youm, J. R.; Han, S. B. Simultaneous determination of five coumarins in Angelicae dahuricae Radix by HPLC/UV and LC-ESI-MS/MS. Biomed. Chromatogr. 2009, 23, 1034-1043.
19. Zheng, X.; Zhang, X.; Sheng, X.; Yuan, Z.; Yang, W.; Wang, Q.; Zhang, L. Simultaneous characterization and quantitation of 11 coumarins in Radix Angelicae Dahuricae by high performance liquid chromatography with electrospray tandem mass spectrometry. J. Pharm. Biomed. Anal. 2010, 51, 599-605.
20. Belsito, E. L.; Carbone, C.; Di Gioia,M. L.; Leggio, A.; Liguori, A.; Perri, F.; Siciliano, C.; Viscomi, M. C. Comparison of the volatile constituents in cold-pressed bergamot oil and a volatile oil isolated by vacuum distillation. J. Agric. Food Chem. 2007, 55, 7847-7851. (Pubitemid 47522196)
21. Peroutka, R.; Schulzová, V.; Botek, P.; Haj-slová, J. Analysis of furanocoumarins in vegetables (Apiaceae) and citrus fruits (Rutaceae). J. Sci. Food Agric. 2007, 87, 2152-2163. (Pubitemid 47232257)
22. International Conference on Harmonization (ICH). ICH Harmonized Tripartite Guideline: Validation of Analytical Procedures: Text and Methodology Q2(R1). 1994, (available at http://www.ich.org/products/guidelines/quality/ article/quality-guidelines.html).
23. Liu, R.; Sun, Q.; Shi, Y.; Kong, L. Isolation and purification of coumarin compounds from the root of Peucedanum decursivum (Miq.) Maxim by high-speed counter-current chromatography. J. Chromatogr., A 2005, 1076, 127-132. (Pubitemid 40725185)
24. Khaled, S. A.; Szendrei, K.; Novak, I.; Reisch, J. Coumarin glycosides from Peucedanum ostruthium. Phytochemistry 1975, 14, 1461-1462.
25. Perel'son, M. E.; Sheinker, Y. N.; Syrova, G. P. NMR spectra of natural coumarin derivatives II. Furocoumarins. Chem. Nat. Compd. 1971, 7, 557-562.
26. Bartnik, M.; Glowniak, K.; Jakubowicz-Gil, J.; Pawlikowska-Pawlega, B.; Gawron, A. Effect of peucedanin and bergapten (5-MOP), furanocoumarins isolated from Peucedanum tauricum Bieb. (Apiaceae) fruits, on apoptosis induction and heat-shock protein expression in HeLa cells. Herba Pol. 2006, 52, 71-78.
27. Epifano, F.; Genovese, S.; Menghini, L.; Curini, M. Chemistry and pharmacology of oxyprenylated secondary plant metabolites. Phytochemistry 2007, 68, 939-953. (Pubitemid 46413340)
28. Ikeda, R.; Wada, M.; Nishigaki, T.; Nakashima, K. Quantification of coumarin derivatives in Noni (Morinda citrifolia) and their contribution of quenching effect on reactive oxygen species. Food Chem. 2009, 113, 1169-1172.
29. Lee, S. O.; Choi, S. Z.; Lee, J. H.; Chung, S. H.; Park, S. H.; Kang, H. C.; Yang, E. Y.; Cho, H. J.; Lee, K. R. Antidiabetic coumarin and cyclitol compounds from Peucedanum japonicum. Arch. Pharm. Res. 2004, 27, 1207-1210.
30. Liao, P. C.; Chien, S. C.; Ho, C. L.; Wang, E. I.; Lee, S. C.; Kuo, Y. H.; Jeyashoke, N.; Chen, J.; Dong, W. C.; Chao, L. K.; Hua, K. F. Osthole regulates inflammatory mediator expression through modulating NF-κB, mitogen-activated protein kinases, protein kinase C, and reactive oxygen species. J. Agric. Food Chem. 2010, 58, 10445-10451.
31. Eeva, M.; Rauha, J.-P.; Vuorela, P.; Vuorela, H. Computerassisted, high-performance liquid chromatography with mass spectrometric detection for the analysis of coumarins in Peucedanum palustre and Angelica archangelica. Phytochem. Anal. 2004, 15, 167-174. (Pubitemid 38714090)
32. Zhang, H.; Gong, C.; Lv, L.; Xu, Y.; Zhao, L.; Zhu, Z.; Chai, Y.; Zhang, G. Rapid separation and identification of furocoumarins in Angelica dahurica by high-performance liquid chromatography with diode-array detection, time-of-flight mass spectrometry and quadrupole ion trap mass spectrometry. Rapid Commun. Mass Spectrom. 2009, 23, 2167-2175.
33. Chen, Y.; Fan, G.; Zhang, Q.; Wu, H.; Wu, Y. Fingerprint analysis of the fruits of Cnidium monnieri extract by high-performance liquid chromatography-diode array detection-electrospray ionization tandem mass spectrometry. J. Pharm. Biomed. Anal. 2007, 43, 926-936. (Pubitemid 46185801)
34. Gökay, O.; Kühner, D.; Los, M.; Götz, F.; Bertsche, U.; Albert, K. An efficient approach for the isolation, identification and evaluation of antimicrobial plant components on an analytical scale, demonstrated by the example of Radix imperatoriae. Anal. Bioanal. Chem. 2010, 398, 2039-2047.