Stress-induced biosynthesis of dicaffeoylquinic acids in globe artichoke

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 18, 2008, Pages 8641-8649

  Moglia, Andrea ^a   Lanter, Sergio ^a   Comino, Cinzia ^a   Acquadro, Alberto ^a   De Vos, Ric ^b   Beekwilder, Jules ^b  

^a UNIVERSITY OF TURIN   (Italy)

^b WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

Abiotic stresses; Dicaffeoylquinic acids; Globe artichoke; Phenolic compounds; UV C radiation

Indexed keywords

ACETIC ACID DERIVATIVE; ANTIOXIDANT; CAFFEOYLQUINIC ACID; CYCLOPENTANE DERIVATIVE; DRUG DERIVATIVE; JASMONIC ACID METHYL ESTER; OXYLIPIN; PHENOL DERIVATIVE; QUINIC ACID; SALICYLIC ACID;

ARTICHOKE; ARTICLE; CHEMISTRY; DRUG EFFECT; METABOLISM; PLANT LEAF; RADIATION EXPOSURE; ULTRAVIOLET RADIATION;

ACETIC ACIDS; ANTIOXIDANTS; CYCLOPENTANES; CYNARA SCOLYMUS; OXYLIPINS; PHENOLS; PLANT LEAVES; QUINIC ACID; SALICYLIC ACID; ULTRAVIOLET RAYS;

CYNARA CARDUNCULUS; CYNARA SCOLYMUS; SCOLYMUS;

EID: 53649097559     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf801653w     Document Type: Article

References (45)

1. Lanteri, S.; di Leo, I.; Ledda, L.; Mameli, M. G.; Portis, E. RAPD variation within and among populations of globe artichoke cultivar 'Spinoso sardo'. Plant Breed. 2001, 120, 243-246.
2. Portis, E.; Mauromicale, G.; Barchi, L.; Mauro, R.; Lanteri, S. Population structure and genetic variation in autochthonous globe artichoke germplasm from Sicily Island. Plant Sci. 2005, 168, 1591-1598.
3. Kraft, K. Artichoke leaf extract recent findings reflecting effects on lipid metabolism, liver and gastrointestinal tracts. Phytomedicine 1997, 4, 369-378.
4. Pittlem, M. H.; Ernst, E. Artichoke leaf extract for serum cholesterol reduction. Perfusion 1998, 11, 338-340.
5. Thompson Coon, J. S.; Hernst, E. Herbs for serum cholesterol reduction: a systematic view. J. Fam. Pract. 2003, 52, 468-478.
6. 4 toxicity in isolated rat hepatocytes. J. Nat. Prod. 1987, 50, 612-617.
7. Brown, J. E.; Rice-Evans, C. A. Luteolin-rich artichoke extract protects low density lipoprotein from oxidation in vitro. Free Radical Res. 1998, 29, 247-255.
8. Gebhardt, R. Antioxidative and protective properties of extracts from leaves of artichoke (Cynara scolymus L.) against hydroperoxide induced oxidative stress in cultured rat hepatocytes. Toxicol. Appl. Pharmacol. 1997, 144, 279-286.
9. Martino, V.; Caffini, N.; Phillipson, J. D.; Lappa, A.; Tchernitchin, A.; Ferraro, G.; Debenedelli, S.; Schilcher, H.; Acevedo, C. Identification and characterization of antimicrobial components in leaf extracts of globe artichoke (Cynara scolymus L.). Acta Hortic. 1999, 501, 111-114.
10. Perez-Garcia, F.; Adzet, T.; Canigueral, S. Activity of artichoke leaf extract on reactive oxygen species in human leukocytes. Free Radical Res. 2000, 33, 661-665.
11. Llorach, R.; Espin, J. C.; Tomas-Barberan, F. A.; Ferreres, F. Artichoke (Cynara scolymus L.) byproducts as a potential source of health-promoting antioxidant phenolics. J. Agric. Food Chem. 2002, 50, 3458-3464.
12. Kukic, J.; Popovic, V.; Petrovic, S.; Mucaji, P.; Ciric, A.; Stojkovic, D.; Sokovic, M. Antioxidant and antimicrobial activity of Cynara cardunculus extracts. Food Chem. 2008, 107, 861-868.
13. Lattanzio, V.; Cicco, N.; Linsalata, V. Antioxidant activities of artichoke phenolics. Acta Hortic. 2005, 681, 421-428.
14. Zhu, X. F.; Zhang, H. X.; Lo, R. Phenolic compounds from the leaf extract of artichoke (Cynara scolymus L.) and their antimicrobial activities. J. Agric. Food Chem 2004, 52, 7272-7278.
15. n analysis of the cis isomers of chlorogenic acids. Food Chem. 2008, 106, 379-385.
16. n identification of chlorogenic acids. J. Agric. Food Chem. 2003, 57, 2900-2911.
17. Wang, M. F.; Simon, J. E.; Aviles, I. F.; He, K.; Zheng, Q. Y.; Tadmor, Y. Analysis of antioxidative phenolic compounds in artichoke (Cynara scolymus L.). J. Agric. Food Chem. 2003, 57, 601-608.
18. Clifford, M. N. Chlorogenic acids and other cinnamates-nature, occurrence and dietary burden. J. Sri. Food Agric. 1999, 79, 369-372.
19. n. J. Agric. Food Chem. 2005, 53, 3821-3832.
20. Panizzi, L.; Scarpati, M. Constitution of cynarine, the active principle of the artichoke. Nature 1954, 174, 1062.
21. Gu, R. L.; Dou, G. F.; Wang, J.; Dong, J. X.; Meng, Z. Y. Simultaneous determination of 1,5-dicaffeoylquinic acid and its active metabolites in human plasma by liquid chromatographytandem mass spectrometry for pharmacokinetic studies. J. Chromatogr., B 2007, 852, 85-91.
22. McDougall, B.; King, P. J.; Wu, B. W.; Hostomsky, Z.; Reinecke, M. G.; Robinson, W. E. Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase. Antimicrob. Agents Chemother. 1998, 42, 140-146.
23. Slanina, J.; Taborska, E.; Bochorakova, H.; Slaninova, I.; Humpa, O.; Robinson, W. E.; Schram, K. H. New and facile method of preparation of the anti-HIV-1 agent, 1,3-dicaffeoylquinic acid. Tetrahedron Lett. 2001, 42, 3383-3385.
24. Dixon, R. A.; Paiva, N. L. Stress-induced phenylpropanoid metabolism. Plant Cell 1995, 7, 1085-1097.
25. Treutter, D. Significance of flavonoids in plant resistance and enhancement of their biosynthesis. Plant Biol. 2005, 7, 581-591.
26. Cantos, E.; Espin, J. C.; Tomas-Barberan, F. A. Effect of wounding on phenolic enzymes in six minimally processed lettuce cultivars upon storage. J. Agric. Food Chem. 2001, 49, 322-330.
27. Izaguirre, M. M.; Mazza, C. A.; Svatos, A.; Baldwin, I. T.; Ballare, C. L. Solar ultraviolet-B radiation and insect herbivory trigger partially overlapping phenolic responses in Nicotiana altenuata and Nicotiana longiflora. Ann. Bot. (London) 2007, 99, 103-109.
28. Niggeweg, R.; Michael, A. J.; Martin, C. Engineering plants with increased levels of the antioxidant chlorogenic acid. Nat. Biotechnol 2004, 22, 746-754.
29. Moco, S.; Bino, R. J.; Vorst, O.; Verhoeven, H. A.; de Groot, J.; van Beek, T. A.; Vervoort, J.; de Vos, C. H. R. A liquid chromatography-mass spectrometry-based metabolome database for tomato. Plant Physiol. 2006, 141, 1205-1218.
30. Beekwilder, J.; Jonker, H.; Meesters, P.; Hall, R. D.; van der Meer, I. M.; de Vos, C. H. R. Antioxidants in raspberry: On-line analysis links antioxidant activity to a diversity of individual metabolites. J. Agric. Food Chem. 2005, 53, 3313-3320.
31. IUPAC. Nomenclature of cyclitols Biochem. J. 1976, 153, 23-31.
32. Tegelberg, R.; Julkunen-Tiitto, R. J.; Aphalo, P. J. Red: far-red light ratio and UV-B radiation: their effects on leaf phenolics and growth of silver birch seedlings. Plant Cell Environ. 2004, 27, 1005-1013.
33. Hagen, S. F.; Solhaug, K. A.; Bengtsson, G. B.; Borge, G. I. A.; Bilger, W. Chlorophyll fluorescence as a tool for non-destructive estimation of anthocyanins and total flavonoids in apples. Postharvest Biol. Technol. 2006, 41, 156-163.
34. Pinelli, P.; Agostini, F.; Comino, C.; Lanteri, S.; Portis, E.; Romani, A. Simultaneous quantification of caffeoyl esters and flavonoids in wild and cultivated cardoon leaves. Food Chem. 2007, 105, 1695-1701.
35. Dayagrosjean, L.; Dumaz, N.; Sarasin, A. The specificity of P53 mutation spectra in sunlight-induced human cancers. J. Photochem. Photobiol. B-Biol. 1995, 28, 115-124.
36. Conconi, A.; Smerdon, M. J.; Howe, G. A.; Ryan, C. A. The octadecanoid signalling pathway in plants mediates a response to ultraviolet radiation. Nature 1996, 383, 826-829.
37. Zacchini, M.; de Agazio, M. Spread of oxidative damage and antioxidative response through cell layers of tobacco callus after UV-C treatment. Plant Physiol. Biochem. 2004, 42, 445-450.
38. Zang, L. Y.; Cosma, G.; Gardner, H.; Castranova, V.; Vallyathan, V. Effect of chlorogenic acid on hydroxyl radical. Mol. Cell. Biochem. 2003, 247, 205-210.
39. Mondolot, L.; La Fisca, P.; Buatois, B.; Talansier, E.; De Kochko, A.; Campa, C. Evolution in caffeoylquinic acid content and histolocalization during Coffea canephora leaf development. Ann. Bot. (London) 2006, 98, 33-40.
40. Gao, C.; Xing, D.; Li, L.; Zhang, L. Implication of reactive oxygen species and mitochondrial disfunction in the early stages of plant programmed cell death induced by ultraviolet-C overexposure. Planta (Berlin) 2008, 227, 755-767.
41. Mackerness, S. A. H.; Surplus, S. L.; Blake, P.; John, C. F.; Buchanan-Wollaston, V.; Jordan, B. R.; Thomas, B. Ultraviolet-B-induced stress and changes in gene expression in Arabidopsis thaliana: role of signalling pathways controlled by jasmonic acid, ethylene and reactive oxygen species. Plant. Cell. Environ. 1999, 22, 1413-1423.
42. Basnizki, J.; Zohary, D. Breeding of seed planted artichoke. Plant Breed. Rev. 1994, 12, 253-269.
43. Mauromicale, G.; Ierna, A.; Lanteri, S.; Licandro, P.; Longo, A. M. G.; Santoiemma, G.; Morello, N. Miglioramento del panorama varietale della cinaricoltura siciliana. Inf. Agrar. 2004, 52, 1-4.
44. Keurentjes, J. J. B.; Fu, J. Y.; de Vos, C. H. R.; Lommen, A.; Hall, R. D.; Bino, R. J.; van der Plas, L. H. W.; Jansen, R. C.; Vreugdenhil, D.; Koornneef, M. The genetics of plant metabolism. Nat. Genet. 2006, 38, 842-849.
45. Reddivari, L.; Hale, A. L.; Miller, J. C. J. Genotype, location, and year influence antioxidant activity, carotenoid content, phenolic content, and composition in specialty potatoes. J. Agric. Food Chem 2007, 55, 8073-8079.