Rapid quantitation of furanocoumarins and flavonoids in grapefruit juice using ultra-performance liquid chromatography

Phytochemical Analysis

Volumn 24, Issue 6, 2013, Pages 654-660

  Vandermolen, Karen M ^a   Cech, Nadja B ^a   Paine, Mary F ^b   Oberlies, Nicholas H ^a  

^a UNIVERSITY OF NORTH CAROLINA AT GREENSBORO   (United States)

^b UNC Hamner Institute for Drug Safety Sciences   (United States)

Author keywords

flavonoid; furanocoumarin; grapefruit; quantitation; UPLC

Indexed keywords

DRUG INTERACTIONS; FLAVONOIDS; FRUIT JUICES; GLYCOPROTEINS; LIQUID CHROMATOGRAPHY;

ANALYTES; CYTOCHROMES P450; FLAVONOID; FURANOCOUMARINS; GRAPEFRUIT; GRAPEFRUIT JUICE; JUICE PRODUCTS; P-GLYCOPROTEIN; QUANTITATION; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

CITRUS FRUITS;

6',7' DIHYDROXYBERGAMOTTIN; ACETONITRILE; AURANTIIN; BERGAMOTTIN; FLAVONOID; FUROCOUMARIN; HESPERIDIN; NARINGENIN; NARIRUTIN; UNCLASSIFIED DRUG; WATER;

ACCURACY; ANALYTIC METHOD; ARTICLE; CALIBRATION; FOOD ANALYSIS; GRAPEFRUIT; GRAPEFRUIT JUICE; NONHUMAN; QUANTITATIVE ANALYSIS; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

CITRUS X PARADISI;

FLAVONOID; FURANOCOUMARIN; GRAPEFRUIT; QUANTITATION; UPLC;

BEVERAGES; CHROMATOGRAPHY, LIQUID; CITRUS PARADISI; FLAVONOIDS; LEAST-SQUARES ANALYSIS; PSORALENS; REPRODUCIBILITY OF RESULTS;

EID: 84886726614     PISSN: 09580344     EISSN: 10991565     Source Type: Journal    
DOI: 10.1002/pca.2449     Document Type: Article

References (41)

1. Avula B, Upparapalli SK, Khan IA,. 2007. Simultaneous analysis of adrenergic amines and flavonoids in Citrus peel jams and fruit juices by liquid chromatography: part 2. J AOAC Int 90: 633-640.
2. Bailey DG, Malcolm J, Arnold O, Spence JD,. 1998. Grapefruit juice-drug interactions. Br J Clin Pharmacol 46: 101-110.
3. Bailey DG, Dresser GK, Leake BF, Kim RB,. 2007. Naringin is a major and selective clinical inhibitor of organic anion-transporting polypeptide 1A2 (OATP1A2) in grapefruit juice. Clin Pharmacol Ther 81: 495-502.
4. Baranowska I, Magiera S,. 2011. Development and validation of a UHPLC method for the determination of flavonoids in red wine. J AOAC Int 94: 786-794.
5. Cao J, Zhou S, Qiu F, Kong W, Wan L, Yang M,. 2012. A simple and fast method for the simultaneous quantification of six flavonoids in Fructus aurantii by UPLC-PDA and confirmation by UPLC/ESI-Q-TOF-MS. Anal Methods 4: 4121-4128.
6. Dahan A, Amidon GL,. 2009. Grapefruit juice and its constituents augment colchicine intestinal absorption: potential hazardous interaction and the role of p-glycoprotein. Pharm Res 26: 883-892.
7. De Castro WV, Mertens-Talcott S, Rubner A, Butterweck V, Derendorf H,. 2006. Variation of flavonoids and furanocoumarins in grapefruit juices: A potential source of variability in grapefruit juice-drug interaction studies. J Agr Food Chem 54: 249-255.
8. De Castro WV, Mertens-Talcott S, Derendorf H, Butterweck V,. 2007. Grapefruit juice-drug interactions: grapefruit juice and its components inhibit P-glycoprotein (ABCB1) mediated transport of talinolol in Caco-2 cells. J Pharm Sci 96: 2808-2817.
9. De Paepe D, Servaes K, Noten B, Diels L, De LM, Van DB, Voorspoels S,. 2013. An improved mass spectrometric method for identification and quantification of phenolic compounds in apple fruits. Food Chem 136: 368-375.
10. Dresser GK, Bailey DG,. 2003. The effects of fruit juices on drug disposition: A new model for drug interactions. Eur J Clin Invest 33: 10-16.
11. Dresser GK, Kim RB, Bailey DG,. 2005. Effect of grapefruit juice volume on the reduction of fexofenadine bioavailability: Possible role of organic anion transporting polypeptides. Clin Pharmacol Ther 77: 170-177.
12. Edwards DJ, Fitzsimmons ME, Schuetz EG, Yasuda K, Ducharme MP, Warbasse LH, Woster PM, Schuetz JD, Watkins P,. 1999. 6',7'-Dihydroxybergamottin in grapefruit juice and Seville orange juice: effects on cyclosporine disposition, enterocyte CYP3A4, and P-glycoprotein. Clin Pharmacol Ther 65: 237-244.
13. Fujita T, Kawase A, Niwa T, Tomohiro N, Masuda M, Matsuda H, Iwaki M,. 2008. Comparative evaluation of 12 immature citrus fruit extracts for the inhibition of cytochrome P450 isoform activities. Biol Pharm Bull 31: 925-930.
14. Fukuda K, Guo L, Ohashi N, Yoshikawa M, Yamazoe Y,. 2000. Amounts and variation in grapefruit juice of the main components causing grapefruit-drug interaction. J Chromatogr B 741: 195-203.
15. Gerber F, Krummen M, Potgeter H, Roth A, Siffrin C, Spoendlin C,. 2004. Practical aspects of fast reversed-phase high-performance liquid chromatography using 3 μm particle packed columns and monolithic columns in pharmaceutical development and production working under current good manufacturing practice. J Chromatogr A 1036: 127-133.
16. Hanley MJ, Cancalon P, Widmer WW, Greenblatt DJ,. 2011. The effect of grapefruit juice on drug disposition. Expert Opin Drug Metab Toxicol 7: 267-286.
17. Harris DC,. 2007. Quantitative Chemical Analysis, 7th edn. W. H. Freeman and Co.: New York.
18. Huang W, Xiong Z-H, Huang X, Chen X, Liu W-P, Wang Y, Ren P,. 2012. Simultaneous UPLC analysis of three major flavonoids in granule decoctions of Fructus Aurantii-type formulae. Pharmazie 67: 586-589.
19. Kumar A, Saini G, Nair A, Sharma R,. 2012. UPLC: A preeminent technique in pharmaceutical analysis. Acta Pol Pharm 69: 371-380.
20. Lin YK, Sheu MT, Huang CH, Ho HO,. 2009. Development of a reversed-phase high-performance liquid chromatographic method for analyzing furanocoumarin components in citrus fruit juices and Chinese herbal medicines. J Chromatogr Sci 47: 211-215.
21. Lown KS, Mayo RR, Leichtman AB, Hsiao H-L, Turgeon DK, Schmiedlin-Ren P, Brown MB, Guo W, Rossi SJ, Benet LZ, Watkins PB,. 1997. Role of intestinal P-glycoprotein (mdr 1) in interpatient variation in the oral bioavailability of cyclosporine. Clin Pharmacol Ther 62: 248-260.
22. MacNair JE, Lewis KC, Jorgenson JW,. 1997. Ultrahigh-pressure reversed-phase liquid chromatography in packed capillary columns. Anal Chem 69: 983-989.
23. MacNair JE, Patel KD, Jorgenson JW,. 1999. Ultrahigh-pressure reversed-phase capillary liquid chromatography: isocratic and gradient elution using columns packed with 1.0-μm particles. Anal Chem 71: 700-708.
24. Manthey JA, Buslig BS,. 2005. Distribution of furanocoumarins in grapefruit juice fractions. J Agr Food Chem 53: 5158-5163.
25. Medina-Remon A, Tulipani S, Rotches-Ribalta M, Mata-Bilbao MDL, Andres-Lacueva C, Lamuela-Raventos RM,. 2011. A fast method coupling ultrahigh performance liquid chromatography with diode array detection for flavonoid quantification in citrus fruit extracts. J Agr Food Chem 59: 6353-6359.
26. Ohnishi A, Matsuo H, Yamada S, Takanaga H, Morimoto S, Shoyama Y, Ohtani H, Sawada Y,. 2000. Effect of furanocoumarin derivatives in grapefruit juice on the uptake of vinblastine by Caco-2 cells and on the activity of cytochrome P450 3A4. Br J Pharmacol 130: 1369-1377.
27. Paine MF, Oberlies NH,. 2007. Clinical relevance of the small intestine as an organ of drug elimination: drug-fruit juice interactions. Expert Opin Drug Metab Toxicol 3: 67-80.
28. Paine MF, Widmer WW, Hart HL, Pusek SN, Beavers KL, Criss AB, Brown SS, Thomas BF, Watkins PB,. 2006. A furanocoumarin-free grapefruit juice establishes furanocoumarins as the mediators of the grapefruit juice-felodipine interaction. Am J Clin Nutr 83: 1097-1105.
29. Paine MF, Widmer WW, Pusek SN, Beavers KL, Criss AB, Snyder J, Watkins PB,. 2008. Further characterization of a furanocoumarin-free grapefruit juice on drug disposition: studies with cyclosporine. Am J Clin Nutr 87: 863-871.
30. Ross SA, Ziska DS, Zhao K, Elsohly MA,. 2000. Variance of common flavonoids by brand of grapefruit juice. Fitoterapia 71: 154-161.
31. Seden K, Dickinson L, Khoo S, Back D,. 2010. Grapefruit-drug interactions. Drugs 70: 2373-2407.
32. Swartz ME,. 2005. UPLC. An introduction and review. J Liq Chromatogr R T 28: 1253-1263.
33. Vanamala J, Reddivari L, Yoo KS, Pike LM, Patil BS,. 2005. Variation in the content of bioactive flavonoids in different brands of orange and grapefruit juices. J Food Compos Anal 19: 157-166.
34. Wacher VJ, Wu CY, Benet LZ,. 1995. Overlapping substrate specificities and tissue distribution of cytochrome P450 3A and P-glycoprotein: implications for drug delivery and activity in cancer chemotherapy. Mol Carcinog 13: 129-134.
35. Wanwimolruk S, Marquez PV,. 2006. Variations in content of active ingredients causing drug interactions in grapefruit juice products sold in California. Drug Metab Drug Interact 21: 233-243.
36. Widmer W, Huan C,. 2005. Variation in furanocoumarin content and new furanocoumarin dimers in commercial grapefruit (Citrus paradisi Macf.) juices. J Food Sci 70: C307-C312.
37. Wilson EG, Broussalis A, Benencia H, Ferraro GE,. 2000. Quantification of the phytoestrogen naringenin in grapefruit and orange juices marketed in Argentina. Acta Farm Bonaerense 19: 277-279.
38. Wolf KK, Li Y, Connolly EA, Won CS, Scarlett YV, Paine MF,. 2011. Grapefruit juice increases systemic exposure of loperamide without consequent central nervous system opiate-like effects in healthy volunteers. Clin Pharmacol Ther 89: S61-S62.
39. Won CS, Scarlett YV, Widmer WW, Paine MF,. 2010. A modified grapefruit juice eliminates furanocoumarins and polymethoxyflavones as candidate mediators of the fexofenadine-grapefruit juice interaction in healthy volunteers. AAPS J 12: S2 (available at www.aapsj.org).
40. Won CS, Oberlies NH, Paine MF,. 2012. Mechanisms underlying food-drug interactions: Inhibition of intestinal metabolism and transport. Pharmacol Ther 136: 186-201.
41. Wu N, Lippert JA, Lee ML,. 2001. Practical aspects of ultrahigh pressure capillary liquid chromatography. J Chromatogr A 911: 1-12.