Metabolite profiling of polyphenols in peels of Citrus limetta Risso by combination of preparative high-speed countercurrent chromatography and LC-ESI-MS/MS

Food Chemistry

Volumn 158, Issue , 2014, Pages 139-152

  Rodríguez Rivera, M Paulina ^a   Lugo Cervantes, Eugenia ^a   Winterhalter, Peter ^b   Jerz, Gerold ^b  

^a CENTRO DE INVESTIGACIÓN Y ASISTENCIA EN TECNOLOGÍA Y DISEÑO DEL ESTADO DE JALISCO   (Mexico)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Citrus limetta Risso; HMG substituted polyphenols; LC ESI MS MS; Preparative HSCCC; Rutaceae; Two dimensional metabolite profiling

Indexed keywords

BIOMOLECULES; DRUG PRODUCTS; FLAVONOIDS; LIQUID CHROMATOGRAPHY; PRINCIPAL COMPONENT ANALYSIS; SUGARS; TWO DIMENSIONAL;

CITRUS LIMETTA RISSO; LC-ESI-MS/MS; METABOLITE PROFILING; POLYPHENOLS; PREPARATIVE HSCCC; RUTACEAE;

METABOLITES;

ABSCISIC ACID; CINNAMIC ACID; CINNAMIC ACID DERIVATIVE; ESTER; FLAVANONE O GLYCOSIDE; FLAVONE; FLAVONOL O GLYCOSIDE; GLYCOSIDE; LIMONOID; LIMONOID GLUCOSIDE; METHANOL; POLYPHENOL; SUGAR ACID; UNCLASSIFIED DRUG; FLAVONOL DERIVATIVE;

ARTICLE; CITRUS; CITRUS LIMETTA; COUNTER CURRENT CHROMATOGRAPHY; ELECTROSPRAY; ELECTROSPRAY MASS SPECTROMETRY; FRACTIONATION; HIGH SPEED COUNTERCURRENT CHROMATOGRAPHY; LIMIT OF DETECTION; LIQUID CHROMATOGRAPHY; METABOLITE; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TANDEM MASS SPECTROMETRY; THIN LAYER CHROMATOGRAPHY; CHEMISTRY; MASS SPECTROMETRY; PROCEDURES;

CHROMATOGRAPHY, LIQUID; CITRUS; COUNTERCURRENT DISTRIBUTION; FLAVONOLS; GLYCOSIDES; MASS SPECTROMETRY; POLYPHENOLS;

EID: 84896532907     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2014.02.077     Document Type: Article

References (51)

1. D.C. Abeysinghe, X. Li, C.D. Sun, W.S. Zhang, C.H. Zhou, and K.S. Chen Bioactive compounds and antioxidant capacities in different edible tissues of citrus fruit of four species Food Chemistry 104 2007 1338 1344 (Pubitemid 46783251)
2. A. Andrade-Cetto, and M. Heinrich Mexican plants with hypoglycemic effect used in the treatment of diabetes Journal of Ethnopharmacology 99 2005 325 348 (Pubitemid 40861709)
3. E. Balestrieri, F. Pizzimenti, A. Ferlazzo, S.V. Giofrè, D.A. Piperno, and R. Romeo et al. Antiviral activity of seed extract from Citrus bergamia towards human retroviruses Bioorganic & Medicinal Chemistry 19 2011 2084 2089
4. D. Barreca, E. Bellocco, C. Caristi, U. Leuzzi, and G. Gattuso Distribution of C- and O-glycosyl flavonoids, (3-hydroxy-3-methylglutaryl) glycosyl flavanones and furocoumarins in Citrus aurantium L. juice Food Chemistry 124 2011 576 582
5. D. Barreca, E. Bellocco, C. Caristi, U. Leuzzi, and G. Gattuso Flavonoid profile and radical-scavenging activity of Mediterranean sweet lemon (Citrus limetta Risso) juice Food Chemistry 129 2011 417 422
6. L. Battinelli, F. Mengoni, M. Lichtner, G. Mazzanti, A. Saija, and C.M. Mastroianni et al. Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells Planta Medica 69 2003 910 913 (Pubitemid 38005446)
7. M. Careri, L. Elviri, and A. Mangia Validation of a liquid chromatography ionspray mass spectrometry method for the analysis of flavanones, flavones and flavonols Rapid Communications in Mass Spectrometry 13 1999 2399 2405
8. F. Cuyckens, R. Rozenberg, E. de Hoffmann, and M. Claeys Structure characterization of flavonoid O-diglycosides by positive and negative nano-electrospray ionization ion trap mass spectrometry Journal of Mass Spectrometry 36 2001 1203 1210 (Pubitemid 33107709)
9. B. D'Abrosca, A. Fiorentino, A. Ricci, M. Scognamiglio, S. Pacifico, and S. Piccolella et al. Structural characterization and radical scavenging activity of monomeric and dimeric cinnamoyl glucose esters from Petrorhagia velutina leaves Phytochemistry Letters 3 2010 38 44
10. D. de Beer, G. Jerz, E. Joubert, V. Wray, and P. Winterhalter Isolation of isomangiferin from honeybush (Cyclopia subternata) using high-speed counter-current chromatography and high-performance liquid chromatography Journal of Chromatography A 1216 2009 4282 4289
11. L. Di Donna, G. De Luca, F. Mazzotti, A. Napoli, R. Salerno, and D. Taverna et al. Statin-like principles of bergamot fruit (Citrus bergamia): Isolation of 3-hydroxymethylglutaryl flavonoid glycosides Journal of Natural Products 72 2009 1352 1354
12. G. Gattuso, C. Caristi, C. Gargiulli, E. Bellocco, G. Toscano, and U. Leuzzi Flavonoid glycosides in bergamot juice (Citrus bergamia Risso) Journal of Agricultural and Food Chemistry 54 11 2006 3929 3935 (Pubitemid 44030573)
13. B. Gentili, and R.M. Horowitz Flavonoids of citrus-VII: Limocitrol and isolimocitrol Tetrahedron 20 1964 2313 2318
14. D. Gutzeit, V. Wray, P. Winterhalter, and G. Jerz Preparative isolation and purification of flavonoids and protocatechuic acid from sea buckthorn juice concentrate (Hippophaë rhamnoides L. ssp. rhamnoides) by high-speed counter-current chromatography Chromatographia 65 2007 1 7 (Pubitemid 46129039)
15. n and NMR and their quantification by HPLC-DAD Journal of Agricultural and Food Chemistry 55 2007 8251 8260
16. Y. Ito Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography Journal of Chromatography A 1065 2005 145 168 (Pubitemid 40228728)
17. G.K. Jayaprakasha, D.V. Dandekar, S.E. Tichy, and B.S. Patil Simultaneous separationa and identification of limonoids from Citrus using liquid chromatography-collision-induced dissociation mass spectrometry Journal of Separation Science 34 2011 2 10
18. H. Kata-Noguchi, Y. Tanaka, T. Murakami, S. Yamamura, and S. Fujihara Isolation and identification of an alleopathic substance from peel of Citrus junos Phytochemistry 61 2002 849 853 (Pubitemid 35439920)
19. S. Kazuno, M. Yanagida, N. Shindo, and K. Murayama Mass spectrometric identification and quantification of glycosyl flavonoids, including dihydrochalcones with neutral loss scan mode Analytical Biochemistry 347 2005 182 192 (Pubitemid 41681804)
20. H. Kumamoto, Y. Matsubara, Y. Itzuka, K. Okamoto, and K. Yokoi Structure and hypotensive effect of flavonoid glycosides in lemon peelings (Part II) Nippon Nôgeikagaku Kaishi 59 1985 677 682
21. S. KunduSen, P.K. Haldar, M. Gupta, U.K. Mazumder, P. Saha, and A. Bala et al. Evaluation of antihyperglycemic activity of Citrus limetta fruit peel in streptozotocin-induced diabetic rats ISRN Endocrinology 2011 2011 10.5402/2011/869273
22. M. Leopoldini, N. Malaj, M. Toscano, G. Sindona, and N. Russo On the inhibitor effects of bergamot juice flavonoids binding to the 3-hydroxy-3-methylglutaryl-CoA reductase (HMGR) Enzyme Journal of Agricultural and Food Chemistry 58 2010 10768 10773
23. P. Lorenz, J. Conrad, J. Bertrams, M. Berger, S. Duckstein, and U. Meyer et al. Investigations into the phenolic constituents of dog's mercury (Mercurialis perennis L.) by LC-MS/MS and GC-MS analyses Phytochemical Analysis 23 2012 60 71
24. G.D. Manners Citrus limonoids: Analysis, bioactivity, and biomedical prospects Journal of Agricultural and Food Chemistry 55 2007 8285 8294 (Pubitemid 350013067)
25. Y. Matsubara, H. Kumamoto, Y. Iizuka, T. Murakami, K. Okamoto, and H. Miyake et al. Structure and hypotensive effect of flavonoid glycosides in Citrus unshui peelings Agricultural and Biological Chemistry 49 1985 909 914 (Pubitemid 15107370)
26. Y. Matsubara, T. Yusa, A. Sawabe, Y. Iizuka, and K. Okamoto Structure and physiological activity of phenyl propanoid glycosides in lemon (Citrus limon BURM. f.) peel Agricultural and Biological Chemistry 55 1991 647 650
27. E.G. Miller, S.E. Taylor, C.W. Berry, J.A. Zimmermann, and S. Hasegawa Citrus limonoids: Increasing importance as anticancer agents ACS Symposium Series 758 2000 132 144
28. Y. Miyake, M. Mochizuki, M. Okada, M. Hiramitsu, Y. Morimitsu, and T. Osawa Isolation of antioxidative phenolic glucosides from lemon juice and their suppressive effect on the expression of blood adhesion molecules Bioscience, Biotechnology, and Biochemistry 71 2007 1911 1919 (Pubitemid 350113152)
29. H. Nakagawa, Y. Takaishi, N. Tanaka, K. Tsuchiya, H. Shibata, and T. Higuti Chemical constituents from the peels of Citrus sudachi Journal of Natural Products 69 2006 1177 1179 (Pubitemid 44409791)
30. n Food Chemistry 130 2012 730 738
31. Y. Nogata, K. Sakamoto, H. Shiratsuchi, T. Ishii, M. Yano, and H. Ohta Flavonoid composition of fruit tissues of Citrus species Bioscience Biotechnology and Biochemistry 70 2006 178 192 (Pubitemid 43150976)
32. B.S. Patil, N.D. Turner, E.G. Miller, and J.S. Brodbelt Potential health benefits of citrus ACS Symposium Series 936 2006 (i-v)
33. J. Peng, G. Yang, G. Fan, and Y. Wu Preparative isolation and separation of a novel and two known flavonoids from Patrinia villosa Juss. by high-speed counter-current chromatography Journal of Chromatography A 1092 2005 235 240 (Pubitemid 41393933)
34. O.R. Pereira, A.M.S. Silva, M.R.M. Domingues, and S.M. Cardoso Indentification of phenolic constituents of Citisus multiflorus Food Chemistry 131 2012 652 659
35. Y.Y. Perez, E. Jimenez-Ferrer, D. Alonso, C.A. Botello-Amaro, and A. Zamilpa Citrus limetta leaves extract antagonizes the hypertensive effect of angiotensin II Journal of Ethnopharmacology 128 2010 611 614
36. A.L. Piccinelli, M. García Mesa, D.M. Armenteros, M.A. Alfonso, A.C. Arevalo, and L. Campone et al. HPLC-PDA-MS and NMR characterization of C-glycosyl flavones in a hydroalcoholic extract of Citrus aurantifolia leaves with antiplatelet activity Journal of Agricultural and Food Chemistry 56 2008 1574 1581 (Pubitemid 351506865)
37. S.M. Poulose, E.D. Harris, and B.S. Patil Citrus limonoids induce apoptosis in human neuroblastoma cells and have radical scavenging activity Journal of Nutrition 135 2005 870 877 (Pubitemid 40464118)
38. M.D.R. Ramos, G. Jerz, S. Villanueva, F. López-Dellamary, R. Waibel, and P. Winterhalter Two glucosylated abscisic acid derivates from avocado seeds (Persea americana Mill. Lauraceae cv. Hass) Phytochemistry 65 7 2004 955 962 (Pubitemid 38471778)
39. B. Risch, and K. Herrmann Hydroxzimtsäure-Verbindungen in Citrus-Früchten Zeitschrift für Lebensmittel-Untersuchung und -Forschung 187 1988 530 534 [in German]
40. B. Risch, K. Herrmann, and V. Wray (E)-O-p-coumaroyl-, (E)-O-feruloyl-derivatives of glucaric acid in citrus Phytochemistry 27 1988 3327 3329
41. B. Risch, K. Herrmann, V. Wray, and L. Grothjahn 2′-(E)-O-p- coumaroylgalactaric acid and 2′-(E)-O-feruloylgalactaric acid in citrus Phytochemistry 26 1987 509 510
42. S. Roowi, and A. Crozier Flavonoids in tropical citrus species Journal of Agricultural and Food Chemistry 59 2011 12217 12226
43. A. Sawabe, H. Kumamoto, and Y. Matsubara Bioactive glycosides in Citrus fruti peels Bulletin of the Institute of Comprehensive Agricultural Sciences, Kinki University 6 1998 57 67
44. T.K. Schoch, G.D. Manners, and S. Hasegawa Analysis of limonoid glucosides from Citrus by electrospray ionization liquid chromatography-mass spectrometry Journal of Agricultural and Food Chemistry 49 2001 1102 1108 (Pubitemid 32884917)
45. E. Stahl, and U. Kaltenbach Dünnschicht-chromatographie: VI. mitteilung. Spurenanalyse von zuckergemischen auf kieselgur G-schichten Journal of Chromatography A 5 1961 351 355 [in German]
46. Q. Tian, and X. Ding Screening for limonoid glucosides in Citrus tangerina (Tanaka) Tseng by high-performance liquid chromatography-electrospray ionization mass spectrometry Journal of Chromatography A 874 2000 13 19 (Pubitemid 30139538)
47. E. Tripoli, M. La Guardia, S. Giammanco, D. Di Majo, and M. Giammanco Citrus flavonoids: Molecular structure, biological activity and nutritional properties: A review Food Chemistry 104 2007 466 479 (Pubitemid 46661050)
48. A.A. Villamar Lima I.N. Indigenista, Atlas de las plantas de la medicina tradicional mexicana 1994 Instituto Nacional Indigenista Mexiko, Col. Tlacopac 902
49. H. Wang, and F. Feng Identification of components in Zhi-Zi-Da-Huang decoction by HPLC coupled with electrospray ionization tandem mass spectrometry, photodiode array and fluorescence detectors Journal of Pharmaceutical and Biomedical Analysis 49 2009 1157 1165
50. P. Waridel, J.-L. Wolfender, K. Ndjoko, K.R. Hobby, H.J. Major, and K. Hostettmann Evaluation of quadrupole time-of-flight tandem mass spectrometry and ion-trap multiple-stage mass spectrometry for the differentiation of C-glycosidic flavonoid isomers Journal of Chromatography A 926 2001 29 41 (Pubitemid 32739004)
51. D.Y. Zhou, Q. Xu, X.Y. Xue, F.F. Zhang, and X.M. Liang Identification of O-diglycosyl flavanones in Fructus aurantii by liquid chromatography with electrospray ionization and collision-induced dissociation mass spectrometry Journal of Pharmaceutical and Biomedical Analysis 42 2006 441 448 (Pubitemid 44375110)