Extensive characterisation of bioactive phenolic constituents from globe artichoke (Cynara scolymus L.) by HPLC-DAD-ESI-QTOF-MS

Food Chemistry

Volumn 141, Issue 3, 2013, Pages 2269-2277

  Abu Reidah, Ibrahim M ^a,b   Arraez Roman, David ^a,b   Segura Carretero, Antonio ^a,b   Fernandez Gutierrez, Alberto ^a,b  

^a UNIVERSITY OF GRANADA   (Spain)

^b Research and Development Functional Food Center (CIDAF)   (Spain)

Author keywords

Artichoke (Cynara scolymus L.); Asteraceae; Flavonoids; HPLC DAD ESI QTOF MS; Mediterranean diet; Phenolic compounds

Indexed keywords

FLAVONOIDS; ISOMERS;

ARTICHOKE (CYNARA SCOLYMUS L.); ASTERACEAE; ESI-QTOF-MS; MEDITERRANEAN DIET; PHENOLIC COMPOUNDS;

PHENOLS;

3 HYDROXYBENZOIC ACID; ANTIOXIDANT; APIGENIN; ARTICHOKE EXTRACT; COUMARIC ACID; FLAVONE DERIVATIVE; FLAVONOL DERIVATIVE; LIGNAN DERIVATIVE; LUTEOLIN 7 GLUCOSIDE; METHANOL; PHENOL DERIVATIVE; PINORESINOL; PLANT EXTRACT; POLYPHENOL; UNCLASSIFIED DRUG;

ARTICHOKE; ARTICLE; ELECTROSPRAY MASS SPECTROMETRY; FOOD COMPOSITION; FUNCTIONAL FOOD; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; NONHUMAN; QUALITATIVE ANALYSIS; TANDEM MASS SPECTROMETRY; ULTRAVIOLET SPECTROSCOPY;

ASTERACEAE; CYNARA SCOLYMUS;

EID: 84879205210     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2013.04.066     Document Type: Article

References (46)

1. Abu-Reidah, I. M., Arraez-Roman, D., Lozano-Sanchez, J., Segura-Carretero, A., & Fernandez-Gutierrez, A. (2012). Phytochemical characterization of green beans (Phaseolus vulgaris L.) by using high performance liquid chromatography coupled with time-of-flight mass spectrometry. Phytochemical Analysis, 24, 105.
2. Abu-Reidah, I. M., Arraez-Roman, D., Quirantes-Pine, R., Fernandez-Arroyo, S., Segura-Carretero, A., & Fernandez-Gutierrez, A. (2012). HPLC-ESI-Q-TOF-MS for a comprehensive characterization of bioactive phenolic compounds in cucumber whole fruit extract. Food Research International, 46, 108-117.
3. Agarwal, R., & Mukhtar, H. 1996). Cancer chemoprevention by polyphenols in green tea and artichoke. Advances in Experimental Medicine and Biology, 401, 35-50. (Pubitemid 26326190)
4. Asen, S., & Horowitz, R. M. (1974). Apigenin 40-O-b-D-glucoside 7-O-b-D-glucuronide: The copigment in the blue pigment of Centaurea cyanus. Phytochemistry, 13, 1219-1223.
5. Azzini, E., Bugianesi, R., Romano, F., Di Venere, D., Miccadei, S., Durazzo, A., et al. (2007). Absorption and metabolism of bioactive molecules after oral consumption of cooked edible heads of Cynara scolymus L. (cultivar Violetto di Provenza) in human subjects: A pilot study. British Journal of Nutrition, 97, 963-969. (Pubitemid 46561897)
6. Brat, P., George, S., Bellamy, A., Chaffaut, L. D., Scalbert, A., Mennen, L., et al. (2006). Daily polyphenol intake in france from fruit and vegetables. The Journal of Nutrition, 136, 2368-2373. (Pubitemid 44329997)
7. Brown, J. E., & Rice-Evans, C. A. (1998). Luteolin-rich artichoke extract protects low density lipoprotein from oxidation in vitro. Free Radical Research, 29, 247-255. (Pubitemid 28499598)
8. Choi, S., Yang, M., Lee, K. Kim, K., & Lee, K. (2007). Lignan and terpene constituents from the aerial parts of Saussurea pulchella. Archives of Pharmacal Research, 30, 1067-1074.
9. Clifford, M. N., Zheng, W., & Kuhnert, N. (2006). Profiling the chlorogenic acids of aster by HPLC-MSn. Phytochemical Analysis, 17, 384-393. (Pubitemid 44697745)
10. Coinu, R., Carta, S., Urgeghe, P. P., Mulinacci, N., Pinelli, P., Franconi, F., & Romani, A. (2007). Dose-effect study on the antioxidant properties of leaves and outer bracts of extracts obtained from Violetto di Toscana artichoke. Food Chemistry, 101, 524-531. (Pubitemid 44333184)
11. De la Rosa, L. A., Alvarez-Parrilla, E., & Gonzalez-Aguilar, G. A. (2010). Fruit and vegetable phytochemicals chemistry, nutritional value, and stability (1st ed.). USA: Wiley-Blackwell Publishing.
12. FAO statistical database. (2010). http://faostat.fao.org/site/339/ default.aspx Accessed 11.05.12.
13. Ferracane, R., Pellegrini, N., Visconti, A., Graziani, G., Chiavaro, E., Miglio, C., & Fogliano, V. (2008). Effects of different cooking methods on antioxidant profile, antioxidant capacity, and physical characteristics of artichoke. Journal of Agricultural and Food Chemistry, 56, 8601-8608.
14. Gebhardt, R. (1997). Antioxidative and protective properties of extracts from leaves of the Artichoke (Cynara scolymus L.) against hydroperoxide-induced oxidative stress in cultured rat hepatocytes. Toxicology and Applied Pharmacology, 144, 279-286. (Pubitemid 27268349)
15. Hausler, M., Ganzera, M., Abel, G., Popp, M., & Stuppner, H. (2002). Determination of caffeoylquinic acids and flavonoids in Cynara scolymus L. by high performance liquid chromatography. Chromatographia, 56, 407-411. (Pubitemid 35221988)
16. IUPAC Commission on the Nomenclature of Organic Chemistry (CNOC) & IUPAC-IUB Commission on Biochemical Nomenclature (CBN) (1976). Nomenclature of cyclitols.
17. Recommendations, 1973. Biochemical Journal, 153, 23-31.
18. Jaiswal, R., Kiprotich, J., & Kuhnert, N. (2011). Determination of the hydroxycinnamate profile of 12 members of the Asteraceae family. Phytochemistry, 72, 781-790.
19. Jun, N. J., Jang, K. C., Kim, S. C., Moon, D. Y., Seong, K. C., Kang, K. H., et al. (2007). Radical scavenging activity and content of cynarin (1,3-dicaffeoylquinic acid) in Artichoke (Cynara scolymus L.). Journal of Applied Biological Chemistry, 50, 244-248.
20. Kajdz?anoska, M., Gjamovski, V., & Stefova, M. (2010). HPLC-DAD-ESI-MSn, identification of phenolic compounds in cultivated strawberries from Macedonia. Macedonian Journal of Chemistry and Chemical Engineering, 29, 181-194.
21. Lattanzio, V., Kroon, P. A., Linsalata, V., & Cardinali, A. (2009). Globe artichoke: A functional food and source of nutraceutical ingredients. Journal of Functional Foods, 1, 131-144.
22. Lattanzio, V., & van Sumere, C. F. (1987). Changes in phenolic compounds during the development and cold storage of artichoke (Cynara scolymus L.) heads. Food Chemistry, 24, 37-50. (Pubitemid 17046825)
23. Liao, S.-G., Zhang, L.-J., Li, C.-B., Lan, Y.-Y., Wang, A.-M., Huang, Y., et al. (2010). Rapid screening and identification of caffeic acid and its esters in Erigeron breviscapus by ultra-performance liquid chromatography/tandem mass spectrometry. Rapid Communications in Mass Spectrometry, 24, 2533-2541.
24. Lombardo, S., Pandino, G., Mauromicale, G., Knodler, M., Carle, R., & Schieber, A. (2010). Influence of genotype, harvest time and plant part on polyphenolic composition of globe artichoke [Cynara cardunculus L. var. scolymus (L.) Fiori]. Food Chemistry, 119, 1175-1181.
25. McDougall, B., King, P. J., Wu, B. W., Hostomsky, Z., Manfred, G., & Robinson, W. E. Jr., (1998). Dicaffeoylquinic acid and dicaffeoyltartaric acid are selective inhibitors of human immunodeficiency virus type 1 integrase. Antimicrobal Agents Chemotherapy, 42, 140-146. (Pubitemid 28053340)
26. Miadokova, E., Nadova, S., Vlckova, V., Duhova, V., Kopaskova, M., Cipak, L., et al. (2008). Antigenotoxic effect of extract from Cynara cardunculus L. Phytotherapy Research, 22, 77-81. (Pubitemid 351155916)
27. Moglia, A., Lanteri, S., Comino, C., Acquadro, A., de Vos, R., & Beekwilder, J. (2008). Stress-induced biosynthesis of dicaffeoylquinic acids in globe artichoke. Journal of Agricultural and Food Chemistry, 56, 8641-8649.
28. Mulinacci N., Prucher, D., Peruzzi, M., Romani, A., Pinelli, P., Giaccherini, C., & Vincieri, F. F. (2004). Commercial and laboratory extracts from artichoke leaves: Estimation of caffeoyl esters and flavonoidic compounds content. Journal of Pharmaceutical and Biomedical Analysis, 34, 349-357. (Pubitemid 38167765)
29. Pan, L., Sinden, M. R., Kennedy, A. H., Chai, H., Watson, L. E., Graham, T. L., et al. (2009). Bioactive constituents of Helianthus tuberosus (Jerusalem artichoke). Phytochemistry Letters, 2, 15-18.
30. Pandino, G., Courts, F. L., Lombardo, S., Mauromicale, G., & Williamson, G. (2009). Caffeoylquinic acids and flavonoids in the immature inflorescence of globe artichoke, wild cardoon, and cultivated cardoon. Journal of Agricultural and Food Chemistry, 58, 1026-1031.
31. Pinelli, P., Agostini, F., Comino, C., Lanteri, S., Portis, E., & Romani, A. (2007). Simultaneous quantification of caffeoyl esters and flavonoids in wild and cultivated cardoon leaves. Food Chemistry, 105, 1695-1701. (Pubitemid 47096853)
32. Repc?ak, M., & Krausova, T. (2009). Phenolic glucosides in the course of ligulate flower development in diploid and tetraploid Matricaria chamomilla. Food Chemistry, 116, 19-22.
33. Sanchez-Rabaneda, F., Jauregui, O., Lamuela-Raventos, R. M., Bastida, J., Viladomat, F., & Codina, C. (2003). Identification of phenolic compounds in artichoke waste by high-performance liquid chromatography-tandem mass spectrometry. Journal of Chromatography A, 1008, 57-72. (Pubitemid 36897653)
34. Santos, M. D., Lopes, N. P., & Iamamoto, Y. (2008). HPLC-ESI-MS/MS analysis of oxidized di-caffeoylquinic acids generated by metalloporphyrin- catalyzed reactions. Quimica Nova, 31, 767-770.
35. Schilling, S., Sigolotto, C.-I., Carle, R., & Schieber, A. (2008). Characterization of covalent addition products of chlorogenic acid quinone with amino acid derivatives in model systems and apple juice by high-performance liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Communications in Mass Spectrometry, 22, 441-448. (Pubitemid 351300576)
36. Schutz K.,Kammerer D.,Carle R.,Schieber A.(2004). Identification and quantification of caffeoylquinic acids and flavonoids from artichoke (Cynara scolymus L.) heads, juice, and pomace by HPLC-DAD-ESI/MSn Journal of Agricultural and Food Chemistry 52.4090-4096.
37. Schutz, K., Kammerer, D., Carle, R., & Schieber, A. (2004). Identification and quantification of caffeoylquinic acids and flavonoids from artichoke (Cynara scolymus L.) heads, juice, and pomace by HPLC-DAD-ESI/MSn. Journal of Agricultural and Food Chemistry, 52, 4090-4096.Schutz, K., Muks, E., Carle, R., & Schieber, A. (2006). Quantitative determination of phenolic compounds in artichoke-based dietary supplements and pharmaceuticals by high-performance liquid chromatography. Journal of Agricultural and Food Chemistry, 54, 8812-8817. (Pubitemid 44797530)
38. Segasothy, M., & Phillips, P. A. (1999). Vegetarian diet: Panacea for modern lifestyle diseases? QJM: An International Journal of Medicine, 92, 531-544. (Pubitemid 29430052)
39. Shimoda, H., Ninomiya, K., Nishida, N., Yoshino, T., Morikawa, T., Matsuda, H., et al. (2003). Anti-Hyperlipidemic sesquiterpenes and new sesquiterpene glycosides from the leaves of artichoke (Cynara scolymus L.): Structure requirement and mode of action. Bioorganic & Medicinal Chemistry Letters, 13, 223-228. (Pubitemid 35441340)
40. Shoeb, M., MacManus, S. M., Jaspars, M., Trevidu, J., Nahar, L., Kong-Thoo-Lin, P., & Sarker, S. D. (2006). Montamine, a unique dimeric indole alkaloid, from the seeds of Centaurea montana (Asteraceae), and it?s in vitro cytotoxic activity against the CaCo2 colon cancer cells. Tetrahedron, 62, 11172-11177. (Pubitemid 44573332)
41. Takeda K. Osakabe, A., Saito, S., Furuyama, D., Tomita, A., Kojima, Y., et al. (2005). Components of protocyanin, a blue pigment from the blue flowers of Centaurea cyanus. Phytochemistry, 66, 1607-1613.
42. Wang, M., Simon, J. E., Aviles, I. F., He, K., Zheng, Q.-Y., & Tadmor, Y. (2003). Analysis of antioxidative phenolic compounds in artichoke (Cynara scolymus L.). Journal of Agricultural and Food Chemistry, 51, 601-608.
43. Willfor, S. M., Smeds, A. I., & Holmbom, B. R. (2006). Chromatographic analysis of lignans. Journal of Chromatography A, 1112, 64-77.
44. Zhang, Y., Zhao, Q., Ma, J., Wu, B., & Zeng, X. (2010). Chemical characterization of phenolic compounds in erigeron injection by rapid-resolution LC coupled with multi-stage and quadrupole-TOF-MS. Chromatographia, 72, 651-658.
45. Zhu, X. F., Zhang, H. X., & Lo, R. (2005). Antifungal activity of Cynara scolymus L. extracts. Fitoterapia, 76, 108-111. (Pubitemid 40139012)
46. Wagener, H., & Kirmayer, W. (1957). Occurrence of apigeninglycosides in composites. Naturwissen-schaften, 44, 307.