Hyphenated Flash Chromatographic Separation and Isolation of Coumarins and Polymethoxyflavones from Byproduct of Citrus Juice Processing Industry

REFERENCES

• USDA ( 2011 ) Citrus: world markets and trade . In: United States Department of Agriculture, Foreign Agricultural Service ; Government Printing Office : Washington , DC .
   Google Scholar
• Marín , F.R. ; Soler-Rivas , C. ; Benavente-García , O. ; Castillo , J. ; Pérez-Alvarez , J.A. ( 2007 ) By-products from different citrus processes as a source of customized functional fibres . Food Chem. , 100 ( 2 ): 736 – 741 .
   Web of Science ®Google Scholar
• Garzón , C.G. ; Hours , R.A. ( 1992 ) Citrus waste: An alternative substrate for pectinase production in solid-state culture . Bioresour. Technol. , 39 ( 1 ): 93 – 95 .
   Web of Science ®Google Scholar
• Bermejo , A. ; Llosá , M.J. ; Cano , A. ( 2011 ) Analysis of Bioactive Compounds in Seven Citrus Cultivars . F. Sci. Technol. Int. , 17 ( 1 ): 55 – 62 .
   PubMed Web of Science ®Google Scholar
• Vikram , A. ; Jayaprakasha , G.K. ; Patil , B.S. ( 2007 ) Simultaneous determination of citrus limonoid aglycones and glucosides by high performance liquid chromatography . Analytica Chimica Acta , 590 ( 2 ): 180 – 186 .
   PubMed Web of Science ®Google Scholar
• Patil , B.S. ; Jayaprakasha , G.K. ; Chidambara Murthy , K.N. ; Vikram , A. ( 2009 ) Bioactive compounds: historical perspectives, opportunities, and challenges . J. Agric. Food Chem. , 57 ( 18 ): 8142 – 8160 .
   PubMed Web of Science ®Google Scholar
• Uckoo , R.M. ; Jayaprakasha , G.K. ; Patil , B.S. ( 2011 ) Rapid separation method of polymethoxyflavones from citrus using flash chromatography . Sep. Purif. Technol. , 81 ( 2 ): 151 – 158 .
   Web of Science ®Google Scholar
• Uckoo , R.M. ; Jayaprakasha , G.K. ; Nelson , S.D. ; Patil , B.S. ( 2011 ) Rapid simultaneous determination of amines and organic acids in citrus using high-performance liquid chromatography . Talanta , 83 ( 3 ): 948 – 954 .
   PubMed Web of Science ®Google Scholar
• Uckoo , R.M. ; Jayaprakasha , G.K. ; Balasubramaniam , V.M. ; Patil , B.S. ( 2012 ) Grapefruit (Citrus paradisi Macfad) phytochemicals composition is modulated by household processing techniques . Journal of Food Science , 77 ( 9 ): C921 – C926 .
   PubMed Web of Science ®Google Scholar
• Kim , J. ; Jayaprakasha , G.K. ; Uckoo , R.M. ; Patil , B.S. ( 2012 ) Evaluation of chemopreventive and cytotoxic effect of lemon seed extracts on human breast cancer (MCF-7) cells . Food and Chemical Toxicology , 50 ( 2 ): 423 – 430 .
   PubMed Web of Science ®Google Scholar
• Uckoo , R.M. ; Jayaprakasha , G.K. ; Bhimanagouda , S.P. ( 2012 ) Chromatographic Techniques for the Separation of Polymethoxyflavones from Citrus . In: Emerging Trends in Dietary Components for Preventing and Combating Disease ; American Chemical Society , Vol. 1093 , 3 – 15 .
   Google Scholar
• Girennavar , B. ; Cepeda , M.L. ; Soni , K.A. ; Vikram , A. ; Jesudhasan , P. ; Jayaprakasha , G.K. ; Pillai , S.D. ; Patil , B.S. ( 2008 ) Grapefruit juice and its furocoumarins inhibits autoinducer signaling and biofilm formation in bacteria . Int. J. Food Microbiol. , 125 ( 2 ): 204 – 208 .
   PubMed Web of Science ®Google Scholar
• Abulrob , A.-N. ; Suller , M.T.E. ; Gumbleton , M. ; Simons , C. ; Russell , A.D. ( 2004 ) Identification and biological evaluation of grapefruit oil components as potential novel efflux pump modulators in methicillin-resistant Staphylococcus aureus bacterial strains . Phytochemistry , 65 ( 22 ): 3021 – 3027 .
   PubMed Web of Science ®Google Scholar
• He , K. ; Iyer , K.R. ; Hayes , R.N. ; Sinz , M.W. ; Woolf , T.F. ; Hollenberg , P.F. ( 1998 ) Inactivation of Cytochrome P450 3A4 by bergamottin, a component of grapefruit juice . Chem. Res. Toxicol. , 11 ( 4 ): 252 – 259 .
   PubMed Web of Science ®Google Scholar
• Baumgart , A. ; Schmidt , M. ; Schmitz , H.-J. ; Schrenk , D. ( 2005 ) Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes . Biochem. Pharmacol. , 69 ( 4 ): 657 – 667 .
   PubMed Web of Science ®Google Scholar
• Frérot , E. ; Decorzant , E. ( 2004 ) Quantification of total furocoumarins in citrus oils by HPLC Coupled with UV, fluorescence, and mass detection . J. Agric. Food Chem. , 52 ( 23 ): 6879 – 6886 .
   PubMed Web of Science ®Google Scholar
• Chouchi , D. ; Barth , D. (1994) Rapid identification of some coumarin derivatives in deterpenated citrus peel oil by gas chromatography. J. Chromatogr. A , 672 (1–2): 177–183.
   PubMed Web of Science ®Google Scholar
• Chen , D. ; Wang , J. ; Jiang , Y. ; Zhou , T. ; Fan , G. ; Wu , Y. ( 2009 ) Separation and determination of coumarins in Fructus cnidii extracts by pressurized capillary electrochromatography using a packed column with a monolithic outlet frit . J. Pharma. Biomed. Anal. , 50 ( 5 ): 695 – 702 .
   PubMed Web of Science ®Google Scholar
• Manthey , J.A. ; Buslig , B.S. ( 2005 ) Distribution of Furanocoumarins in Grapefruit Juice Fractions . J. Agri. Food Chem. , 53 ( 13 ): 5158 – 5163 .
   PubMed Web of Science ®Google Scholar
• Wangensteen , H. ; Molden , E. ; Christensen , H. ; Malterud , K.E. ( 2003 ) Identification of epoxybergamottin as a CYP3A4 inhibitor in grapefruit peel . Eur. J. Cli. Pharm. , 58 ( 10 ): 663 – 668 .
   PubMed Web of Science ®Google Scholar
• Kawaii , S. ; Tomono , Y. ; Katase , E. ; Ogawa , K. ; Yano , M. ( 1999 ) Isolation of furocoumarins from bergamot fruits as HL-60 differentiation-inducing compounds . J. Agric. Food Chem. , 47 ( 10 ): 4073 – 4078 .
   PubMed Web of Science ®Google Scholar
• Girennavar , B. ; Jayaprakasha , G.K. ; Jadegoud , Y. ; Nagana Gowda , G.A. ; Patil , B.S. ( 2007 ) Radical scavenging and cytochrome P450 3A4 inhibitory activity of bergaptol and geranylcoumarin from grapefruit . Bio. Med. Chem. , 15 ( 11 ): 3684 – 3691 .
   PubMed Web of Science ®Google Scholar
• Feger , W. ; Brandauer , H. ; Gabris , P. ; Ziegler , H. ( 2006 ) Nonvolatiles of commercial lime and grapefruit oils separated by high-speed countercurrent chromatography . J. Agric. Food Chem. , 54 ( 6 ): 2242 – 2252 .
   PubMed Web of Science ®Google Scholar
• Mandadi , K. ; Ramirez , M. ; Jayaprakasha , G.K. ; Faraji , B. ; Lihono , M. ; Deyhim , F. ; Patil , B.S. ( 2009 ) Citrus bioactive compounds improve bone quality and plasma antioxidant activity in orchidectomized rats . Phytomedicine , 16 ( 6–7 ): 513 – 520 .
   PubMed Web of Science ®Google Scholar
• Raman , G. ; Jayaprakasha , G.K. ; Cho , M. ; Brodbelt , J. ; Patil , B.S. ( 2005 ) Rapid adsorptive separation of citrus polymethoxylated flavones in non-aqueous conditions . Sep. Purif. Technol. , 45 ( 2 ): 147 – 152 .
   Web of Science ®Google Scholar
• Yu , J. ; Dandekar , D.V. ; Toledo , R.T. ; Singh , R.K. ; Patil , B.S. ( 2007 ) Supercritical fluid extraction of limonoids and naringin from grapefruit (Citrus paradisi Macf.) seeds . Food Chem. , 105 ( 3 ): 1026 – 1031 .
   Web of Science ®Google Scholar
• Raman , G. ; Cho , M. ; Brodbelt , J.S. ; Patil , B.S. ( 2005 ) Isolation and purification of closely related Citrus limonoid glucosides by flash chromatography . Phytochem. Anal. , 16 ( 3 ): 155 – 160 .
   PubMed Web of Science ®Google Scholar
• Jayaprakasha , G.K. ; Dandekar , D.V. ; Tichy , S.E. ; Patil , B.S. ( 2011 ) Simultaneous separation and identification of limonoids from citrus using liquid chromatography-collision-induced dissociation mass spectra . J. Sep. Sci. , 34 ( 1 ): 2 – 10 .
   PubMed Web of Science ®Google Scholar
• Jayaprakasha , G.K. ; Mandadi , K.K. ; Poulose , S.M. ; Jadegoud , Y. ; Nagana Gowda , G.A. ; Patil , B.S. ( 2008 ) Novel triterpenoid from Citrus aurantium L. possesses chemopreventive properties against human colon cancer cells . Bioorganic & Medicinal Chemistry , 16 ( 11 ): 5939 – 5951 .
   PubMed Web of Science ®Google Scholar
• Dass , C. ( 2006 ) Hyphenated Separation Techniques . In: Fundamentals of Contemporary Mass Spectrometry ; John Wiley & Sons, Inc. , 151 – 194 .
   Google Scholar
• Peroutka , R. ; Schulzová , V. ; Botek , P. ; Hajšlová , J. ( 2007 ) Analysis of furanocoumarins in vegetables (Apiaceae) and citrus fruits (Rutaceae) . J. Sci. Food Agric. , 87 ( 11 ): 2152 – 2163 .
   Web of Science ®Google Scholar
• Koichi , M. ; Keisuke , O. ( 1989 ) On the flavonoid constituents from the peels of Citrus hassaku Hort. ex Tanaka . Chem. Pharm. Bull. , 37 ( 4 ): 1092 – 1094 .
   Google Scholar
• Wang , D. ; Wang , J. ; Huang , X. ; Tu , Y. ; Ni , K. ( 2007 ) Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques . J. Pharma. Biomed. Anal. , 44 ( 1 ): 63 – 69 .
   PubMed Web of Science ®Google Scholar
• Girennavar , B. ; Poulose , S.M. ; Jayaprakasha , G.K. ; Bhat , N.G. ; Patil , B.S. ( 2006 ) Furocoumarins from grapefruit juice and their effect on human CYP 3A4 and CYP 1B1 isoenzymes . Bioorg. Med. Chem. , 14 ( 8 ): 2606 – 2612 .
   PubMed Web of Science ®Google Scholar
• Uckoo , R.M. ; Jayaprakasha , G.K. ; Patil , B.S. ( 2012 ) Chromatographic Techniques for the Separation of Polymethoxyflavones from Citrus; Patil, B.S., Jayaprakasha, G.K., Murthy, K.N.C., Seeram, N. Eds.; Emerging Trends in Dietary Components for Preventing and Combating DiseaseACS Symposium Series (In Press).
   Google Scholar
• Girennavar , B. ; Jayaprakasha , G.K. ; Patil , B.S. ( 2007 ) Potent inhibition of Human Cytochrome P450 3A4, 2D6, and 2C9 isoenzymes by grapefruit juice and its furocoumarins . J. Food Sci. , 72 ( 8 ): C417 – C421 .
   PubMed Web of Science ®Google Scholar