Application of LC and LC-MS to the Analysis of Melatonin and Serotonin in Edible Plants

References

• Adão , R. C. and Glória , M. B. 2005 . Bioactive amines and carbohydrate changes during ripening of “Prata” banana (Musa acuminata × M. balbisiana). . Food Chemistry. , 90 ( 4 ) : 705 – 711 .
   Web of Science ®Google Scholar
• Afreen , F. , Zobayed , S. M.A. and Kozai , T. 2006 . Melatonin in Glycyrrhiza uralensis: response of plant roots to spectral quality of light and UV-B radiation. . J. Pineal Res. , 41 ( 2 ) : 108 – 115 .
   PubMed Web of Science ®Google Scholar
• Badria , F. A. 2002 . Melatonin, serotonin, and tryptamine in some Egyptian food and medicinal plants. . J. Medicinal Food. , 5 ( 3 ) : 153 – 157 .
   PubMedGoogle Scholar
• Bartsch , C. , Bartsch , H. and Karasek , M. A. 2002 . Melatonin in clinical oncology. . Neuroendocrinol. Lett. , 23 ( Suppl. l ) : 30 – 38 .
   PubMedGoogle Scholar
• Blask , D. E. , Sauer , L. A. and Dauchy , R. T. 2002 . Melatonin as a chronobiotic/anticancer agent: cellular, biochemical, and molecular mechanisms of action and their implications for circadian-based cancer therapy. . Curr. Top. Med. Chem. , 2 ( 2 ) : 113 – 132 .
   PubMedGoogle Scholar
• Briejer , M. R. , Mathis , C. A. and Schuurkes , J. A.J. 1997 . 5-HT receptor types in the rat ileum longitudinal muscle: focus on 5-HT2 receptors mediating contraction. . Neurogastroenterol Motil. , 9 ( 4 ) : 231 – 237 .
   PubMed Web of Science ®Google Scholar
• Brzezinski , A. 1997 . Melatonin in humans. . New Engl. J. Med. , 336 ( 3 ) : 186 – 195 .
   PubMed Web of Science ®Google Scholar
• Bubenik , G. A. 2002 . Review: Gastrointestinal melatonin: localization, function, and clinical relevance. . Digestive Diseases Sciences. , 47 ( 10 ) : 2336 – 2348 .
   PubMed Web of Science ®Google Scholar
• Burkhardt , S. , Tan , D. X. , Manchester , L. C. , Hardeland , R. and Reiter , R. J. 2001 . Detection and quantification of the antioxidant melatonin in montmorency and balaton tart cherries (Prunus cerasus). . J. Agric. Food Chem. , 49 ( 10 ) : 4898 – 4902 .
   PubMed Web of Science ®Google Scholar
• Chen , G. F. , Huo , Y. S. , Tan , D. X. , Liang , Z. , Zhang , W. B. and Zhang , Y. K. 2003 . Melatonin in Chinese medicinal herbs. . Life Sciences. , 73 ( 1 ) : 19 – 26 .
   PubMed Web of Science ®Google Scholar
• Dubbels , R. , Reiter , R. J. , Klenke , E. , Goebel , A. , Schnakenberg , E. , Ehlers , C. , Schiwara , H. W. and Schloot , W. 1995 . Melatonin in edible plants identified by radioimmunoassay and by high performance liquid chromatography-mass spectrometry. . J. Pineal Res. , 18 ( 1 ) : 28 – 31 .
   PubMed Web of Science ®Google Scholar
• Engstrom , K. , Lundgren , L. and Samuelsson , G. 1992 . Bioassay-guided isolation of serotonin from fruits of Solanum tuberosum L. . Acta Pharmaceutica Nordica. , 4 ( 2 ) : 91 – 92 .
   PubMedGoogle Scholar
• Frazer , A. and Hensler , J. G. 1999 . “ Understanding the neuroanatomical organization of serotonergic cells in brain provides insight into the functions of this neurotransmitter ” . In Basic Neurochemistry, 6th Ed. , 264 – 268 . Baltimore, MD : Lippincott Williams and Wilkins .
   Google Scholar
• Fuhrberg , B. , Balzer , I. , Hardeland , R. , Werner , A. and Lüning , K. 1996 . The vertebrate pineal hormone melatonin is produced by the brown alga Pterygophora californica and mimics dark effects on growth rate in the light. . Planta. , 200 ( 1 ) : 125 – 131 .
   Web of Science ®Google Scholar
• Garcia-Parrilla , M. C. , Cantos , E. and Troncoso , A. M. 2009 . Analysis of melatonin in foods. . J. Food Composition and Analysis. , 22 ( 3 ) : 177 – 183 .
   Web of Science ®Google Scholar
• González-Gómez , D. G. , Lozano , M. , Fernández-León , M.F. , Ayuso , M. C. , Bernalte , M. J. and Rodríguez , A.B. 2009 . Detection and quantification of melatonin and serotonin in eight sweet cherry cultivars (Prunus avium L.). . Eur Food Res Technol. , 229 ( 2 ) : 223 – 229 .
   Web of Science ®Google Scholar
• Hardeland , R. and Poeggeler , B. 2003 . Non-vertebrate melatonin. . J. Pineal Res. , 34 ( 4 ) : 233 – 241 .
   PubMed Web of Science ®Google Scholar
• Harumi , T. and Matsushima , S. 2000 . Separation and assay methods for melatonin and its precursors. . J. Chromatogr. B. , 747 ( 1–2 ) : 95 – 110 .
   PubMedGoogle Scholar
• Hattori , A. , Migitaka , H. , Iigo , M. , Itoh , M. , Yamamoto , K. , Ohtani-Kaneko , R. , Hara , M. , Suzuki , T. and Reiter , R. J. 1995 . Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates. . Biochemistry and Molecular Biology International. , 35 ( 3 ) : 627 – 634 .
   PubMedGoogle Scholar
• Hernández-Ruiz , J. and Arnao , M. B. 2008a . Distribution of melatonin in different zones of lupin and barley plants at different ages in the presence and absence of light. . J. Agric. Food Chem. , 56 ( 22 ) : 10567 – 10573 .
   PubMed Web of Science ®Google Scholar
• Hernández-Ruiz , J. and Arnao , M. B. 2008b . Melatonin stimulates the expansion of etiolated lupin cotyledons. . Plant Growth Regul. , 55 ( 1 ) : 29 – 34 .
   Web of Science ®Google Scholar
• Hernández-Ruiz , J. , Cano , A. and Arnao , M. B. 2004 . Melatonin: a growth-stimulating compound present in lupin tissues. . Planta. , 220 ( 1 ) : 140 – 144 .
   PubMed Web of Science ®Google Scholar
• Hernández-Ruiz , J. , Cano , A. and Arnao , M. B. 2005 . Melatonin acts as a growth-stimulating compound in some monocot species. . J. Pineal Res. , 39 ( 2 ) : 137 – 142 .
   PubMed Web of Science ®Google Scholar
• Hosseinian , F. S. , Li , W. D. and Beta , T. 2008 . Measurement of anthocyanins and other phytochemicals in purple wheat. . Food Chemistry. , 109 ( 4 ) : 916 – 924 .
   PubMed Web of Science ®Google Scholar
• Huang , T. H. and Kissinger , P. T. 1996 . Liquid chromatographic determination of serotonin in homogenized dog intestine and rat brain tissue using a 2 mm i.d. PEEK column. . Current Separations. , 14 ( 3–4 ) : 114 – 119 .
   Google Scholar
• Iriti , M. , Rossoni , M. and Faoro , F. 2006 . Melatonin content in grape: myth or panacea? . J. Sci Food Agric. , 86 ( 10 ) : 1432 – 1438 .
   Web of Science ®Google Scholar
• Kang , S. and Back , K. 2006 . Enriched production of N-hydroxycinnamic acid amides and biogenic amines in pepper (Capsicum annuum) flowers. . Scientia Horticulturae. , 108 ( 3 ) : 337 – 341 .
   Web of Science ®Google Scholar
• Kang , S. , Kang , K. , Lee , K. and Back , K. 2007 . Characterization of tryptamine 5-hydroxylase and serotonin synthesis in rice plants. . Plant Cell Rep. , 26 ( 11 ) : 2009 – 2015 .
   PubMed Web of Science ®Google Scholar
• Kebarle , P. and Verkerk , U. H. 2009 . Electrospray: From ions in solution to ions in the gas phase, what we know now. . Mass Spectrometry Reviews. , 28 ( 6 ) : 898 – 917 .
   PubMed Web of Science ®Google Scholar
• Kirakosyan , A. , Seymour , E. M. , Urcuyo Llanes , D.E. , Kaufman , P. B. and Bolling , S. F. 2009 . Chemical profile and antioxidant capacities of tart cherry products. . Food Chemistry. , 115 ( 1 ) : 20 – 25 .
   Web of Science ®Google Scholar
• Kolář , J. , Macháčková , I. , Eder , J. , Prinsen , E. , Dongen , W. V. , Onckelen , H. V. and Illnerová , H. 1997 . Melatonin: occurrence and daily rhythm in Chenopodium rubrum . Phytochemistry. , 44 ( 8 ) : 1407 – 1413 .
   Web of Science ®Google Scholar
• Kolář , J. and Macháčkov , I. 2005 . Melatonin in higher plants: Occurrence and possible functions. . J. Pineal Res. , 39 ( 4 ) : 333 – 341 .
   PubMed Web of Science ®Google Scholar
• Lavizzari , T. , Veciana-Nogués , M.T. , Bover-Cid , S. , Mariné-Font , A. and Vidal-Carou , M.C. 2006 . Improved method for the determination of biogenic amines and polyamines in vegetable products by ion-pair high-performance liquid chromatography. . J. Chromatogr. A. , 1129 ( 1 ) : 67 – 72 .
   PubMed Web of Science ®Google Scholar
• Ly , D. , Kang , K. , Choi , J. Y. , Ishihara , A. , Back , K. and Lee , S. G. 2008 . HPLC analysis of serotonin, tryptamine, tyramine, and the hydroxycinnamic acid amides of serotonin and tyramine in food vegetables. . J. Med. Food. , 11 ( 2 ) : 385 – 389 .
   PubMed Web of Science ®Google Scholar
• Maldonado , M. D. , Murillo-Cabezas , F. , Terrón , M. P. , Tan , D. X. , Manchester , L. C. and Reiter , R. J. 2007 . The potential of melatonin in reducing morbidity-mortality after craniocerebral trauma. . J. Pineal Res. , 42 ( 1 ) : 1 – 11 .
   PubMed Web of Science ®Google Scholar
• Manchester , L. C. , Tan , D. X. , Reiter , R. J. , Park , W. , Monis , K. and Qi , W. B. 2000 . High levels of melatonin in the seeds of edible plants possible function in germ tissue protection. . Life Sciences. , 67 ( 25 ) : 3023 – 3029 .
   PubMed Web of Science ®Google Scholar
• Murch , S. J. , KrishnaRaj , S. and Saxena , P. K. 2000 . Tryptophan is a precursor for melatonin and serotonin biosynthesis in in vitro regenerated St. John's wort (Hypericum perforatum L. cv. Anthos) plants. . Plant Cell Rep. , 19 ( 7 ) : 698 – 704 .
   PubMed Web of Science ®Google Scholar
• Niessen , W. M.A. 1998 . Advances in instrumentation in liquid chromatography–mass spectrometry and related liquid-introduction techniques. . J. Chromatogr. A. , 794 ( 1–2 ) : 407 – 435 .
   PubMed Web of Science ®Google Scholar
• Núez-Vergara , L.J. , Squella , J. A. , Sturm , J. C. , Baez , H. and Camargo , C. 2001 . Simultaneous determination of melatonin and pyridoxine in tablets by gas chromatography-mass spectrometry. . J. Pharma. and Biomedic. Analy. , 26 ( 5–6 ) : 929 – 938 .
   PubMed Web of Science ®Google Scholar
• Okazaki , M. and Ezura , H. 2009 . Profiling of melatonin in the model tomato (Solanum lycopersicum L.) cultivar Micro-Tom. . J. Pineal Res. , 46 ( 3 ) : 338 – 343 .
   PubMed Web of Science ®Google Scholar
• Pape , C. and Lüning , K. 2006 . Quantification of melatonin in phototrophic organisms. . J. Pineal Res. , 41 ( 2 ) : 157 – 165 .
   PubMed Web of Science ®Google Scholar
• Paredes , S. D. , Korkmaz , A. , Manchester , L. C. , Tan , D. X. and Reiter , R. J. 2009 . Phytomelatonin: a review. . J. Experimental Botany. , 60 ( 1 ) : 57 – 69 .
   PubMed Web of Science ®Google Scholar
• Pöggeler , B. , Balzer , I. , Hardeland , R. and Lerchl , A. 1991 . Pineal hormone melatonin oscillates also in the dinoflagellate Gonyaulax polyedra . Naturwissenschaften. , 78 ( 6 ) : 268 – 269 .
   Google Scholar
• Posmyk , M. M. and Janas , K. M. 2009 . Melatonin in plants. . Acta Physiol Plant. , 31 ( 1 ) : 1 – 11 .
   Web of Science ®Google Scholar
• Puerta , C. D.L. , Carrascosa-Salmoral , M.P. , García-Luna , P.P. , Lardone , P. J. , Herrera , J. L. , Fernández-Montesinos , R. , Guerrero , J. M. and Pozo , D. 2007 . Melatonin is a phytochemical in olive oil. . Food Chemistry. , 104 ( 2 ) : 609 – 612 .
   Web of Science ®Google Scholar
• Reiter , R. J. 1993 . The melatonin rhythm: Both a clock and a calendar. . Experientia. , 49 ( 8 ) : 654 – 664 .
   PubMedGoogle Scholar
• Reiter , R. J. and Tan , D. X. 2002 . Melatonin an antioxidant in edible plants. . Ann. N.Y. Acad. Sci. , 957 : 341 – 344 .
   PubMed Web of Science ®Google Scholar
• Reiter , R. J. , Manchester , L. C. and Tan , D. X. 2005 . Melatonin in walnuts: influence on levels of melatonin and total antioxidant capacity of blood. . Nutrition. , 21 ( 9 ) : 920 – 924 .
   PubMed Web of Science ®Google Scholar
• Reiter , R. J. , Tan , D. X. , Burkhardt , S. and Manchester , L. C. 2001 . Melatonin in plants. . Nutrition Reviews. , 59 ( 9 ) : 286 – 290 .
   PubMed Web of Science ®Google Scholar
• Reiter , R. J. , Tan , D. X. , Manchester , L. C. , Simopoulos , A. P. , Maldonado , M. D. , Flores , L. J. and Terron , M. P. 2007 . Melatonin in edible plants (phytomelatonin): identification, concentrations, bioavailability and proposed functions. . World Review of Nutrition and Dietetics. , 97 : 211 – 230 .
   PubMedGoogle Scholar
• Salvador , M. T. , Murillo , M. D. , Rodríguez-Yoldi , M.C. , Alcade , A. I. , Mesonero , J. E. and Rodríguez-Yoldi , M.J. 2000 . Effects of serotonin on the physiology of the rabbit small intestine. . Can. J. Physiol. Pharmacol. , 78 : 359 – 366 .
   PubMed Web of Science ®Google Scholar
• Sheard , M. H. and Aghajanian , G. K. 1967 . Neural release of brain serotonin and body temperature [28]. . Nature. , 216 ( 5114 ) : 495 – 496 .
   PubMed Web of Science ®Google Scholar
• Tamura , T. , Sano , I. , Satoh , M. , Mizumoto , A. and Itoh , Z. 1996 . Pharmacological characterization of 5-hydroxytryptamine-induced motor activity (in vitro) in the guinea-pig gastric antrum and corpus. . Eur. J. Pharmacol. , 308 ( 3 ) : 315 – 324 .
   PubMed Web of Science ®Google Scholar
• Tan , D. X. , Manchester , L. C. , Hardeland , R. , Lopez-Burillo , S. , Mayo , J. C. , Sainz , R. M. and Reiter , R. J. 2003 . Melatonin: a hormone, a tissue factor, an autocoid, a paracoid, and an antioxidant vitamin. . J. Pineal Res. , 34 ( 1 ) : 75 – 78 .
   PubMed Web of Science ®Google Scholar
• Tan , D. X. , Manchester , L. C. , Mascio , P. D. , Martinez , G. R. , Prado , F. M. and Reiter , R. J. 2007a . Novel rhythms of N1-acetyl-N2-formyl-5-methoxykynuramine and its precursor melatonin in water hyacinth: Importance for phytoremediation. . FASEB J. , 21 ( 8 ) : 1724 – 1729 .
   PubMed Web of Science ®Google Scholar
• Tan , D. X. , Manchester , L. C. , Terron , M. P. , Flores , L. J. and Reiter , R. J. 2007b . One molecule, many derivatives: A never-ending interaction of melatonin with reactive oxygen and reactive nitrogen species? . J. Pineal Res. , 42 ( 1 ) : 28 – 42 .
   PubMed Web of Science ®Google Scholar
• Taylor , D. L. 1995 . Close-up on serotonin. Learn how this key neurotransmitter influences moods and behavior. . Nursing. , 25 ( 4 ) : 64
   PubMedGoogle Scholar
• Terrón , M. P. , Marchena , J. M. , Shadi , F. , Harvey , S. , Lea , R. W. and Rodríguez , A.B. 2001 . Melatonin: An antioxidant at physiological concentrations. . J. Pineal Res. , 31 ( 1 ) : 95 – 96 .
   PubMed Web of Science ®Google Scholar
• Van Tassel , D.L. and O'Neill , S.D. 2001 . Putative regulatory molecules in plants: Evaluating melatonin. . J Pineal Res. , 31 ( 1 ) : 1 – 7 .
   PubMed Web of Science ®Google Scholar
• Van Tassel , D.L. , Roberts , N. , Lewy , A. and O'Neill , S.D. 2001 . Melatonin in plant organs. . J. Pineal Res. , 31 ( 1 ) : 8 – 15 .
   PubMed Web of Science ®Google Scholar
• Vijayayalaxmi , C. , Thomas , R. , Reiter , R. J. and Herman , T. S. 2002 . Melatonin: from basic research to cancer treatment clinics. . J. Clin. Oncol. , 20 ( 10 ) : 2575 – 2601 .
   PubMed Web of Science ®Google Scholar
• Willoughby , R. , Sheehan , E. and Mitrovich , S. 1998 . A Global View of LC/MS. How to Solve your Most Challenging Analytical Problems , 380 – 390 . Pittsburgh, PA : Global View Publishing .
   Google Scholar