(+)-methyl jasmonate-induced bioformation of myricetin, quercetin and kaempferol in red raspberries

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 22, 2010, Pages 11639-11644

  De La Peña Moreno, Fernando ^a   Blanch, Gracia Patricia ^a   Ruiz Del Castillo, Maria Luisa ^a  

^a INSTITUTE OF FOOD SCIENCE   (Spain)

Author keywords

enantiomers; enzyme assay; flavonols; Methyl jasmonate; red raspberry

Indexed keywords

ENZYMATIC ASSAY; ENZYME ASSAY; FLAVONOL SYNTHASE; FLAVONOLS; HYDROXYLASES; KAEMPFEROL; L-PHENYLALANINE; METHYL JASMONATE; MYRICETIN; PHENYLALANINE AMMONIA-LYASE; POST-HARVEST TREATMENTS; RED RASPBERRY;

AMINO ACIDS; ASSAYS; CHIRALITY; ENANTIOMERS; ENZYMES; ETHANOL; FATTY ACIDS; PHENOLS;

PLANTS (BOTANY);

ACETIC ACID DERIVATIVE; CYCLOPENTANE DERIVATIVE; FLAVONOID; JASMONIC ACID METHYL ESTER; KAEMPFEROL; KAEMPFEROL DERIVATIVE; MYRICETIN; OXYLIPIN; PLANT EXTRACT; QUERCETIN;

ARTICLE; BIOTRANSFORMATION; CHEMISTRY; DRUG EFFECT; EVALUATION; FOOD HANDLING; FRUIT; METABOLISM; METHODOLOGY; ROSACEAE;

ACETIC ACIDS; BIOTRANSFORMATION; CYCLOPENTANES; FLAVONOIDS; FOOD HANDLING; FRUIT; KAEMPFEROLS; OXYLIPINS; PLANT EXTRACTS; QUERCETIN; ROSACEAE;

RUBUS IDAEUS;

EID: 78649244818     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf102875b     Document Type: Article

References (31)

1. Russo, G. L. Ins and outs of dietary phytochemicals in cancer chemoprevention Biochem. Pharmacol. 2007, 74, 533-544
2. Sporn, M. B.; Liby, K. T. Cancer chemoprevention: scientific promise, clinical uncertainty Nat. Clin. Pract. Oncol. 2005, 2, 518-525
3. Vinson, J. A.; Hao, Y.; Xuehui, S.; Zubik, L. Phenol antioxidant quantity and quality of foods: vegetables J. Agric. Food Chem. 1998, 46, 3630-3634
4. Chen, D.; Daniel, K. G.; Chen, M. S.; Kuhn, D. J.; Landis-Piwowar, K. R.; Dou, Q. P. Dietary flavonoids are proteasome inhibitors and apoptosis inducers in human leukemia cells Biochem. Pharmacol. 2005, 69, 1421-1432
5. Orsolic, N.; Knezevic, A. H.; Sver, L.; Terzic, S.; Basic, I. Immunomodulatory and antimetastatic action of propolis and related polyphenolic compounds J. Ethnopharmacol. 2004, 94, 307-315
6. Elattar, T. M. A.; Virji, A. S. The inhibitory effects of curcumin, genistein, quercetin and cisplatin on the growth of oral cancer cells in vitro Anticancer Res. 2000, 20, 1733-1738
7. Pérez-Vizcaino, F.; Bishop-Bailley, D.; Lodi, F.; Duarte, J.; Cogolludo, A.; Moreno, L.; Bosca, L.; Mitchell, J. A.; Warner, T. D. The flavonoid quercetin induces apoptosis and inhibits JNK activation in intimal vascular smooth muscle cells Biochem. Biophys. Res. Commun. 2006, 346, 919-925
8. Hertog, M. G. L.; Feskens, E. J. M.; Kromhout, D. Antioxidant flavonols and coronary heart disease risk Lancet 1997, 349, 699
9. Keli, S. O.; Hertog, M. G. L.; Feskens, E. J. M.; Kromhout, D. Dietary flavonoids, antioxidant vitamins, and incidence of stroke. The Zutphen study Arch. Int. Med. 1996, 156, 637-642
10. Knekt, P.; Järvinen, R.; Seppänen, R.; Heliövaara, M.; Teppo, L.; Pukkala, E.; Aromaa, A. Dietary flavonoids and the risk of lung cancer and other malignant neoplasms Am. J. Epidemiol. 1997, 146, 223-230
11. Garcia-Closas, R.; Gonzalez, C. A.; Agudo, A.; Riboli, E. Intake of specific carotenoids and flavonoids and the risk of gastric cancer in Spain Cancer Causes Control 1999, 10, 71-75
12. Häkkinen, S. H.; Kärenlampi, S. O.; Heinonen, I. M.; Mykkänen, H. M.; Törrönen, A. R. Content of the flavonols quercetin, myricetin, and kaempferol in 25 edible berries J. Agric. Food Chem. 1999, 47, 2274-2279
13. Halbwirth, H.; Puhl, I.; Haas, U.; Jezik, K.; Treutter, D.; Stich, K. Two-phase flavonoid formation in developing strawberry (Fragaria X ananassa) fruit J. Agric. Food Chem. 2006, 54, 1479-1485
14. Lukacin, R.; Gröning, I.; Schiltz, E.; Britsch, L.; Matern, U. Purification of recombinant flavanone 3β-hydroxylase from Petunia hybrida and assignment of the primary site of proteolytic degradation Arch. Biochem. Biophys. 2000, 375, 364-370
15. Lukacin, R.; Britsch, L. Identification of strictly conserved histidine and arginine residues as part of the active site in Petunia hybrida flavanone 3β-hydroxylase Eur. J. Biochem. 1997, 249, 748-757
16. Lukacin, R.; Wellmann, F.; Britsch, L.; Martens, S.; Matern, U. Flavonol synthase from Citrus unshiu is a bifunctional dioxygenase Phytochemistry 2003, 62, 287-292
17. Crozier, A.; Burns, J.; Aziz, A. A.; Stewart, A. J.; Rabiasz, H. S.; Jenkins, G. I.; Edwards, C. A.; Lean, M. E. J. Antioxidant flavonols from fruits, vegetables and beverages: measurements and bioavailability Biol. Res. 2000, 33, 79-88
18. Fernando Ayala-Zavala, J.; Wang, S. Y.; Wang, Ch.Y.; González- Aguilar, G. A. Methyl jasmonate in conjunction with ethanol treatment increases antioxidant capacity, volatile compounds and postharvest life of strawberry fruit Eur. Food Res. Technol. 2005, 221, 731-738
19. Wang, K.; Jin, P.; Cao, S.; Shang, H.; Yang, Z.; Zheng, Y. Methyl jasmonate reduces decay and enhances antioxidant capacity in Chinese bayberries J. Agric. Food Chem. 2009, 57, 5809-5815
20. de la Peña Moreno, F.; Blanch, G. P.; Flores, G.; Ruiz del Castillo, M. L. Impact of post-harvest methyl jasmonate treatment on the volatile composition and flavonol content of strawberries J. Sci. Food Agric. 2010, 90, 989-994
21. Kim, H.-J.; Chen, F.; Wang, X.; Choi, J.-H. Effect of methyl jasmonate on phenolics, isothiocyanate, and metabolic enzymes in radish sprout (Raphanus sativus L.) J. Agric. Food Chem. 2006, 54, 7263-7269
22. Heredia, J. B.; Cisneros-Zevallos, L. The effect of exogenous ethylene and methyl jasmonate on pal activity, phenolic profiles and antioxidant capacity of carrots (Daucus carota) under different wounding intensities Postharvest Biol. Technol. 2009, 51, 242-249
23. Cao, S.; Zheng, Y.; Wang, K.; Jin, P.; Rui, H. Methyl jasmonate reduces chilling injury and enhances antioxidant enzyme activity in postharvest loquat fruit Food Chem. 2009, 115, 1458-1463
24. Koda, Y.; Kikuta, Y.; Kitahara, T.; Nishi, T.; Mori, K. Comparisons of various biological activities of stereoisomers of methyl jasmonate Phytochemistry 1992, 31, 1111-1114
25. Acree, T. E.; Nishida, R.; Fukami, H. Odor thresholds of the stereoisomers of methyl jasmonate J. Agric. Food Chem. 1985, 33, 425-427
26. Blanch, G. P.; Flores, G.; Caja, M. M.; Ruiz del Castillo, M. L. Enantioselective isolation of methyl jasmonate using permethyl-β- cyclodextrin HPLC J. Sep. Sci. 2009, 32, 180-184
27. Bialczyk, J.; Lechowski, Z.; Libik, A. Regulation of tannin synthesis in leaves of tomato seedlings by phytohormones and plant growth inhibitors Z. Pflanzenkr. Pflanzensch. 1998, 105, 496-503
28. Rudell, D. R.; Mattheis, J. P.; Fan, X.; Fellman, J. K. Methyl jasmonate enhances anthocyanin accumulation and modifies production of phenolics and pigments in 'Fuji' apple J. Am. Soc. Hortic. Sci. 2002, 127, 435-441
29. Mikkonen, T. P.; Määttä, K. R.; Hukkanen, A. T.; Kokko, H. I.; Törrönen, A. R.; Kärenlampi, S. O.; Karjalainen, R. O. Flavonol content varies among black currant cultivars J. Agric. Food Chem. 2001, 49, 3274-3277
30. Anttonen, M. J.; Karjalainen, R. O. Environmental and genetic variation of phenolic compounds in red raspberry J. Food Compos. Anal. 2005, 18, 759-769
31. Missang, C. E.; Guyot, S.; Renard, C. A. G. C. Flavonols and anthocyanins of bush butter, Dacryodes edulis (G. Don) H.J. Lam, fruit. Changes in their composition during ripening J. Agric. Food Chem. 2003, 51, 7475-7480