Physicochemical and thermodynamic characterization of the encapsulation of methyl jasmonate by natural and modified cyclodextrins using reversed-phase high-pressure liquid chromatography

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 47, 2013, Pages 11347-11354

  López Nicolás, José Manuel ^a   Escorial Camps, Marta ^a   Pérez Sánchez, Horacio ^b   García Carmona, Francisco ^a  

^a UNIVERSITY OF MURCIA   (Spain)

^b CATHOLIC UNIVERSITY OF MURCIA   (Spain)

Author keywords

cell culture; Cyclodextrin; elicitor; encapsulation; jasmonate; reversed phase liquid chromatography

Indexed keywords

ELICITOR; JASMONATES; MODIFIED CYCLODEXTRINS; MOLECULAR MODELING STUDIES; PHYSICOCHEMICAL CONDITIONS; REVERSED-PHASE LIQUID CHROMATOGRAPHY; THERMODYNAMIC CHARACTERIZATION; THERMODYNAMIC PARAMETER;

CELL CULTURE; CHROMATOGRAPHY; ENCAPSULATION; HIGH PRESSURE LIQUID CHROMATOGRAPHY; MOLECULES;

CYCLODEXTRINS;

ACETIC ACID DERIVATIVE; CYCLODEXTRIN; CYCLOPENTANE DERIVATIVE; JASMONIC ACID METHYL ESTER; OXYLIPIN;

ARTICLE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; REVERSED PHASE LIQUID CHROMATOGRAPHY; THERMODYNAMICS;

ACETATES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, REVERSE-PHASE; CYCLODEXTRINS; CYCLOPENTANES; OXYLIPINS; THERMODYNAMICS;

EID: 84889780649     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf402920p     Document Type: Article

References (33)

1. Lattanzio, V.; Kroon, P. A.; Linsalata, V.; Cardinali, A. Globe artichoke: A functional food and source of nutraceutical ingredients J. Funct. Foods 2009, 1, 131-144
2. Repka, V.; Fischerová, I.; Šilhárová, K. Methyl jasmonate is a potent elicitor of multiple defense responses in grapevine leaves and cell-suspension cultures Biol. Plant. 2004, 48, 273-283
3. Morales, M.; Bru, R.; García-Carmona, F.; Barceló, A. R.; Pedreño, M. A. Effect of dimethyl-β-cyclodextrins on resveratrol metabolism in Gamay grapevine cell cultures before and after inoculation with shape Xylophilus ampelinus Plant Cell, Tissue Organ Cult. 1998, 53, 179-187
4. Kessler, A.; Baldwin, I. T. Plant responses to insect herbivory: The emerging molecular analysis Annu. Rev. Plant Biol. 2002, 53, 299-328
5. Weiler, E. W.; Albrecht, T.; Groth, B.; Xia, Z.-Q.; Luxem, M.; Liß, H.; Andert, L.; Spengler, P. Evidence for the involvement of jasmonates and their octadecanoid precursors in the tendril coiling response of Bryonia dioica Phytochem. 1993, 32, 591-600
6. Moreno, F.; de la, P.; Blanch, G. P.; Ruiz del Castillo, M. L. (+)-Methyl jasmonate-induced bioformation of myricetin, quercetin and kaempferol in red raspberries J. Agric. Food Chem. 2010, 58, 11639-11644
7. Pérez, A. G.; Sanz, C.; Richardson, D. G.; Olías, J. M. Methyl jasmonate vapor promotes β-carotene synthesis and chlorophyll degradation in Golden Delicious apple peel J. Plant Growth Regul. 1993, 12, 163-167
8. Wolucka, B. A.; Goossens, A.; Inzé, D. Methyl jasmonate stimulates the de novo biosynthesis of vitamin C in plant cell suspensions J. Exp. Bot. 2005, 56, 2527-2538
9. Tassoni, A.; Durante, L.; Ferri, M. Combined elicitation of methyl-jasmonate and red light on stilbene and anthocyanin biosynthesis J. Plant Physiol. 2012, 169, 775-781
10. Lalel, H. J. D.; Singh, Z.; Tan, S. C. The role of methyl jasmonate in mango ripening and biosynthesis of aroma volatile compounds J. Hortic. Sci. Biotechnol. 2003, 78, 470-484
11. Tegge, G.; Szejtli, J. Cyclodextrins and their inclusion complexes Starch/Staerke 1982, 34, 395-395
12. López-Nicolás, J. M.; Bru, R.; Sánchez-Ferrer, A.; García-Carmona, F. Use of "soluble lipids" for biochemical processes: Linoleic acid-cyclodextrin inclusion complexes in aqueous solutions Biochem. J. 1995, 308, 151-154
13. Del Valle, E. M. M. Cyclodextrins and their uses: A review Proc. Biochem. 2004, 39, 1033-1046
14. Bru, R.; Sellés, S.; Casado-Vela, J.; Belchí-Navarro, S.; Pedreño, M. A. Modified cyclodextrins are chemically defined glucan inducers of defense responses in grapevine cell cultures J. Agric. Food Chem. 2006, 54, 65-71
15. Zamboni, A.; Vrhovsek, U.; Kassemeyer, H.-H.; Mattivi, F.; Velasco, R. Elicitor-induced resveratrol production in cell cultures of different grape genotypes (Vitis spp.) Vitis 2006, 45, 63-68
16. Zamboni, A.; Gatto, P.; Cestaro, A.; Pilati, S.; Viola, R.; Mattivi, F.; Moser, C.; Velasco, R. Grapevine cell early activation of specific responses to DIMEB, a resveratrol elicitor BMC Genomics 2009, 10, 363
17. Lijavetzky, D.; Almagro, L.; Belchi-Navarro, S.; Martínez-Zapater, J. M.; Bru, R.; Pedreño, M. A. Synergistic effect of methyljasmonate and cyclodextrin on stilbene biosynthesis pathway gene expression and resveratrol production in Monastrell grapevine cell cultures BMC Res. Notes 2008, 1, 132
18. Durante, M.; Caretto, S.; Quarta, A.; De Paolis, A.; Nisi, R.; Mita, G. β-Cyclodextrins enhance artemisinin production in Artemisia annua suspension cell cultures Appl. Microbiol. Biotechnol. 2011, 90, 1905-1913
19. Belchi-Navarro, S.; Pedreño, M. A.; Corchete, P. Methyl jasmonate increases silymarin production in Silybum marianum (L.) Gaernt cell cultures treated with β-cyclodextrins Biotechnol. Lett. 2011, 33, 179-184
20. Clarot, I.; Clédat, D.; Battu, S.; Cardot, P. J. Chromatographic study of terpene derivatives on porous graphitic carbon stationary phase with β-cyclodextrin as mobile phase modifier J. Chromatogr., A 2000, 903, 67-76
21. Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility J. Comput. Chem. 2009, 30, 2785-2791
22. Ali, S. M.; Khan, S.; Crowyn, G. Structure determination of fexofenadine-α-cyclodextrin complex by quantitative 2D ROESY analysis and molecular mechanics studies Magn. Reson. Chem. 2012, 50, 299-304
23. Trott, O.; Olson, A. J. AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading J. Comput. Chem. 2010, 31, 455-461
24. Gazpio, C.; Sánchez, M.; García-Zubiri, I. X.; Vélaz, I.; Martínez-Ohárriz, C.; Martín, C.; Zornoza, A. HPLC and solubility study of the interaction between pindolol and cyclodextrins J. Pharm. Biomed. Anal. 2005, 37, 487-492
25. López-Nicolás, J. M.; Núñez-Delicado, E.; Pérez-López, A. J.; Barrachina, A. C.; Cuadra-Crespo, P. Determination of stoichiometric coefficients and apparent formation constants for β-cyclodextrin complexes of trans -resveratrol using reversed-phase liquid chromatography J. Chromatogr., A 2006, 1135, 158-165
26. Matsui, Y.; Mochida, K. Binding forces contributing to the association of cyclodextrin with alcohol in an aqueous solution Bull. Chem. Soc. Jpn. 1979, 52, 2808-2814
27. Debowski, J.; Jurczak, J.; Sybilska, D.; Zukowski, J. Separation of some aromatic amino acids by reversed-phase high-performance liquid chromatography using α- or β-cyclodextrin as mobile phase component J. Chromatogr., A 1985, 329, 206-210
28. Muñoz de la Pena, A.; Ndou, T. T.; Anigbogu, V. C.; Warner, I. M. Solution studies of β-cyclodextrin-pyrene complexes under reversed-phase liquid chromatographic conditions: Effect of alcohols as mobile-phase comodifiers Anal. Chem. 1991, 63, 1018-1023
29. Hinze, W. L. Applications of cyclodextrins in chromatographic separations and purification methods Sep. Purif. Rev. 1981, 10, 159-237
30. López-Nicolás, J. M.; García-Carmona, F. Rapid, simple and sensitive determination of the apparent formation constants of trans -resveratrol complexes with natural cyclodextrins in aqueous medium using HPLC Food Chem. 2008, 109, 868-875
31. López-Nicolás, J. M.; Rodríguez-Bonilla, P.; García-Carmona, F. Complexation of pinosylvin, an analogue of resveratrol with high antifungal and antimicrobial activity, by different types of cyclodextrins J. Agric. Food Chem. 2009, 57, 10175-10180
32. López-Nicolás, J. M.; Rodríguez-Bonilla, P.; Méndez-Cazorla, L.; García-Carmona, F. Physicochemical study of the complexation of pterostilbene by natural and modified cyclodextrins J. Agric. Food Chem. 2009, 57, 5294-5300
33. Rodríguez-Bonilla, P.; López-Nicolás, J. M.; García-Carmona, F. Use of reversed phase high pressure liquid cromatography for the physicochemical and thermodynamic characterization of oxyresveratrol/β-cyclodextrin complexes J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2010, 878, 1569-1575