Determination of oxygen heterocyclic components in citrus products by HPLC with UV detection

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 15, 2009, Pages 6543-6551

  Dugo, Paola ^a   Piperno, Anna ^a   Romeo, Roberto ^a   Cambria, Maria ^a   Russo, Marina ^a   Carnovale, Caterina ^a   Mondello, Luigi ^a  

^a UNIVERSITY OF MESSINA   (Italy)

Author keywords

Citrus products; Coumarins; Furocoumarins; HPLC DAD; Polymethoxylated flavones

Indexed keywords

HETEROCYCLIC COMPOUND; OXYGEN; VEGETABLE OIL;

ARTICLE; CHEMISTRY; CITRUS FRUIT; EVALUATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INSTRUMENTATION; METHODOLOGY; ULTRAVIOLET SPECTROPHOTOMETRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CITRUS; HETEROCYCLIC COMPOUNDS; OXYGEN; PLANT OILS; SPECTROPHOTOMETRY, ULTRAVIOLET;

CITRUS;

EID: 68249104437     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf901209r     Document Type: Article

References (44)

1. Murray, R. D. H. In Progress in the Chemistry of Organic Natural Products; Herz, W., Falk, H., Kirby, G. W., Moore, R. E., Eds.; SpringerVerlag: Wien, Austria, 2002; Vol. 83. pp 1-529.
2. Murray, R. D. H.; Mendey, J.; Brown, S. A. The Natural Coumarins; Wiley: New York, 1982.
3. Kayser, O.; Kolodziej. H. Z. Z. Antibacterial activity of simple coumarins: structural requirements for biological activity. Z. Naturforsch. 1999, 54C, 169-174.
4. Wu, T. S.; Tsang, Z. J.; Wu, P. L.; Lin, F. W.; Li, C. Y.; Teng, C. M.; Lee. K. H. New constituents and antiplatelet aggregation and antiHIV principles of Artemisia capillaris. Bioorg. Med. Chem. 2001, 9. 77-83.
5. Riveiro, M. E.; Shayo, C.; Monczor, F.; Fernández, N.; Baldi, A.; De Kimpe, N.; Rossi. J.; Debenedetti. S.; Davio, C. Induction of cell differentiation in human leukemia U-937 cells by 5-oxygenated-6,7- methylenedioxycoumarins from Pterocaulon polystachyum. Cancer Lett. 2004, 210, 179-188.
6. Luchini, A. C.; Rodrigues-Orsi, P.; Cestari, S. H.; Seito. L. N.; Witaicenis, A.; Pellizzon. C. H.; Di Stasi, L. C. Intestinal antiinflammatory activity of coumarin and 4-hydroxycoumarin in the trinitrobenzenesulphonic acid model of rat colitis, Biol. Pharm. Bull. 2008, 31, 1343-1350.
7. Kennedy, R. O.; Thames. R. D. Coumarins: Biology, Application and Mode of Action; Wiley: Chichester, U.K., 1997.
8. Zahradink, M. The Production and Applications of Fluorescent Brightening Agents; Wiley: New York, 1982.
9. Maeda, M. Laser Dyes; Accademic: New York. 1984
10. Kostova, I. Synthetic and natural coumarins as cytotoxic agents. Curr. Med. Chem.-Anti-Cancer Agents 2005, 5, 29-46.
11. Prince, M.; Campbell, C. T.; Robertson, T. A.; Wells, A. J.; Kleiner, H. E. Naturally occurring coumarins inhibit 7,12-dimethylbenz[a]anthracene DNA adduct formation in mouse mammary gland. Carcinogenesis 2006, 27, 1204-1213.
12. Soine, T. O. Naturally occurring coumarins and related physiological activities. J. Pharm. Sci. 2006, 53, 231-264.
13. Wulff, H.; Rauer. H.; Düring, T.; Hanselmann, C.; Ruff, K.; Wrisch, A.; Grissmer, S.; Hänsel, W. Alkoxypsoralens, novel nonpeptide blockers of Shaker-type K channels: synthesis and photoreactivity. J. Med. Chem. 1998. 41, 4542-4549.
14. Peroutka, R.; Schulzová, V.; Botek. P.; Hajšlová, J. Analysis of furanocoumarins in vegetables (Apiaceae) and citrus fruits (Ruaceae). J. Sci. Food Agric. 2007, 87, 2152-2163.
15. Dugo, P.; McHale, D. The oxygen heterocyclic compounds of citrus essential oils. In Citrus, the Genus Citrus; Dugo. G., Di Giacomo, A., Eds.; Taylor and Francis: London, U.K., 2000; pp 355-390.
16. Frérot, E.; Decorzant, E. Quantification of total furanocoumarins in citrus oils by HPLC coupled with UV, fluorescence and mass detection. J. Agric. Food Chem. 2004, 52, 6879-6886.
17. Kleiner, H. E.; Xia, X.; Sonoda, J.; Zhang, J.; Pontius, E.; Abey, J.; Evans, R. M.; Moore, D. D.; Di Giovanni, J. Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice. Taxicol. Appl. Pharmacol. 2008, 232, 337-350.
18. Row, E. C.; Brown, S. A.; Stachulski, A. V.; Lennard, M. S. Synthesis of 8-geranyloxypsoralen anlogues and their evaluation as inhibitors of CYP3A4. Bioorg. Med. Chem. 2006, 14, 3865-3871.
19. Dugo, P.; Mondello, L.; Cogliandro. E.; Stagno D'Alcontres. I.; Cotroneo, A. On the genuineness of citrus essential oils. Part XLVI. Polymethoxylated Flavones of the non-volatile residue of sweet orange and mandarin essential oils. Flavour Fragrance J. 1994, 9, 105-111.
20. Dugo, P.; Mondello, L.; Cogliandro, E.; Verzera, A.; Dugo. G. On the genuineness of citrus essential oils. 51. Oxygen heterocyclic compounds of bitter orange oil. J. Agric. Food Chem. 1996, 44, 544-549.
21. Dugo, P.; Mondello, L.; Lamonica, G.; Dugo. G. Characterization of cold-pressed key and Persian lime oils by gas chromatography, gas chromatography/mass spectroscopy, high-performance liquid chromatography and physicochemical indices. J. Agric. Food Chem. 1997, 45, 3608-3616.
22. Kawai, S.; Tomono, Y.; Katese, E.; Ogawa, K.; Yano, M. Isolation of furocoumarins from bergamot fruits as HL-60. Differentiationinducing compounds. J. Agric. Food Chem. 1999, 47, 4073-4078.
23. Row, E. C.; Brown, S. A.; Stachulski, A. V.; Lennard. M. S. Design, synthesis and evaluation of furanocoumarin monomers as inhibitors of CYP3A4. Org. Biomol. Chem. 2006, 4, 1604-1610.
24. Stanley, W. L.; Vannier, S. H. Chemical composition of lemon oil 1. Isolation of a series of substituted coumarin. J. Am. Chem. Soc. 1957, 79, 3488-3491.
25. Kim, Y. K.; Kim, Y. S.; Ryu, S. Y. Antiproliferative effect of furanocoumarins from the root of Angelica dahurica on cultured human tumor cell lines. Phytother. Res. 2007, 21, 288-290.
26. Ito, C.; Fujiwara, K.; Kajita, M.; Ju-Ichi, M.; Takemura, Y.; Suzuki, Y.; Tanaka, K.; Omura, M.; Furukawa, H. New coumarins from citrus plants. Chem. Pharm. Bull. 1991, 39, 2509-2513.
27. 3- catalyzed reactions of 5-alkylidene Meldrum's acids with phenols: one-pot assembly of 3.4-dihydrocoumarins, 4-chromanones, coumarins and chromones. J. Org. Chem. 2006, 71, 409-412.
28. Ziegler, H.; Spiteller, G. Coumarins and psoralens from Sicilian lemon oil (Citrus L. Burm. F.). Flavour Fragrance J. 1992, 7, 129-139.
29. The Fitness for Purpose of Analytical methods: A laboratory Guide to method Validation and related Topics; EURACHEM Guide, 1998.
30. Kaminski, M.; Kartanowicz, R.; Kaminski, M. M.; Kròlicka, A.; Sidwa-Gorycka, M.; Lojkoska, E.; Gorzen, W. HPLC-DAD in identification and quantification of selected coumarins in crude extracts from plant cultures of Amni majus and Ruta gruveolens. J. Sep. Sci. 2003, 28. 18-34.
31. Way, W. K.; Campbell, W. The Application Notebook; Supelco, Feb 2007; pp 55.
32. Way, W.K. The Reporter Europe; Supelco. Oct 2007; Vol. 28. pp 3-4.
33. Donato, P.; Dugo, P.; Cacciola, F.; Dugo, G.; Mondello, L. High peak capacity separation of peptides through the serial connection of LC shell-packed coloumns. J. Sep. Sci. 2009, 32, 1129-1136.
34. Hokanson, G. C. A life cycle approach to the validation of analytical methods during pharmaceutical product development, Part I. The initial validation process. Pharm. Technol. 1994, 18, 118-130.
35. François, I.; de Villiers, A.; Tiempont, B.; David, F.; Sandra, P. Comprehensive two-dimensional liquid chromatography applying two parallel columns in the second dimension. J. Chromatoer., A 2008, 1178, 33-42.
36. Weber, B.; Hartmann. B.; Stöckigt, D.; Schreiber, K.; Roloff. M.; Bertram, H.; Schmidt, C. Liquid chromatography/mass spectrometry and liquid chromatography;nuclear magnetic resonance as a complementary analytical techniques for unambiguous identification of polymethoxylated flavones in residue from molecular distillation of oreange peel oils (Citrus sinensis). J. Agric. Food Chem. 2006, 54, 274-278.
37. Feger, W.; Brandauer, H.; Gabris, P.; Ziegler, H. Nonvolatiles of commercial lime and grapefruit oils separated by high-speed countercurrent chromatography. J. Agric. Food Chem. 2006, 54, 2242-2252.
38. Finsten, J. Earl Grey tea intoxication, Lancet 2002, 359, 1484.
39. Gardana. C.; Nalin, F.; Simonetti, P. Evaluation of flavonoids and furanocoumarins from Citrus bergamia (Bergamot) juice and identification of new compounds. Molecules 2008, 13, 2220-2228.
40. Gattuso, G.; Barreca, D.; Caristi, C.; Gargiulli, C.; Lezzi, U. Distribution of flavonoids and furanocoumarins in juices from cultivars of Citrus bergamia Risso. J. Agric. Food Chem. 2007, 55, 9921-9927.
41. Versani, A.; Natali, N.; Russo, M. T.; Antonelli, A. Analysis of some Italian lemon liquor (limoncello). J. Agric. Food Chem. 2003, 51, 4978-4983.
42. Crupi, M. L.; Costa, R.; Dugo. P.; Dugo. G.; Mondello. L. A comprehensive study on the chemical composition and aromatic characteristic of lemon liquor, Food Chem. 2007, 105, 771-783.
43. Dugo, P.; Mondello, L.; Cogliandro, E.; Cavazza, A.; Dugo. G. On the genuineness of citrus essential oils. Part LIII. Determination of the composition of oxygen heterocyclic fraction of lemon essential oils (Citrus limon L. Burm. F.) by normal phase high performance liquid chromatography. Flavour Fragrance J. 1998, 13, 329-334.
44. Dugo, P.; Favoino, O.; Luppino. R.; Dugo, G.; Mondello, L. Comprehensive two-dimensional normal phase (adsorption-reversed phase liquid chromatography, Anal. Chem. 2004, 76, 2525-2530.