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Volumn 35, Issue 4, 2003, Pages 269-275

Melatonin: Structural characterization of its non-enzymatic mono-oxygenate metabolite

Author keywords

1D and 2D nuclear magnetic resonance; Mass spectra; Melatonin; Metabolites; Structure

Indexed keywords

ACETAMIDE DERIVATIVE; FERROUS GLUCONATE; HEMOGLOBIN; HYPOCHLOROUS ACID; MELATONIN; N [2 (5 METHOXY 2 OXO 2,3 DIHYDRO 1H INDOL 3 YL)ETHYL]ACETAMIDE; UNCLASSIFIED DRUG;

EID: 0242269982     PISSN: 07423098     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1600-079X.2003.00086.x     Document Type: Article
Times cited : (25)

References (40)
  • 1
    • 33947460818 scopus 로고
    • Isolation of melatonin the pineal gland factor that lightens the pinealocytes
    • LERNER AB, CASE JD, TAKAHASHI Y et al. Isolation of melatonin the pineal gland factor that lightens the pinealocytes. J Am Chem Soc 1958; 80:2587.
    • (1958) J Am Chem Soc , vol.80 , pp. 2587
    • Lerner, A.B.1    Case, J.D.2    Takahashi, Y.3
  • 2
    • 0000611823 scopus 로고
    • Melatonin: That ubiquitously acting pineal hormone
    • REITER RJ. Melatonin: that ubiquitously acting pineal hormone. News Physiol Sci 1991; 6:223-227.
    • (1991) News Physiol Sci , vol.6 , pp. 223-227
    • Reiter, R.J.1
  • 3
    • 0029422385 scopus 로고
    • Melatonin immunoreactivity in the photosynthetic prokaryote, Rhodospirillum rubrum implication for an ancient antioxidant system
    • MANCHESTER LC, POEGGELER B, ALVARES FL et al. Melatonin immunoreactivity in the photosynthetic prokaryote, Rhodospirillum rubrum implication for an ancient antioxidant system. Cell Mol Biol Res 1995; 41:391-395.
    • (1995) Cell Mol Biol Res , vol.41 , pp. 391-395
    • Manchester, L.C.1    Poeggeler, B.2    Alvares, F.L.3
  • 4
    • 0025891852 scopus 로고
    • Pineal hormone melatonin oscillates also in the dinoflagellate, Gonyaulax polydrea
    • POEGGELER B, BALZER I, HARDELAND R et al. Pineal hormone melatonin oscillates also in the dinoflagellate, Gonyaulax polydrea. Naturwissenschaten 1991; 78:268-269.
    • (1991) Naturwissenschaten , vol.78 , pp. 268-269
    • Poeggeler, B.1    Balzer, I.2    Hardeland, R.3
  • 5
    • 0029552280 scopus 로고
    • Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates
    • HATTORI A, MIGITAKA H, MASAYAKE I et al. Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates. Biochem Mol Biol Int 1995; 35:627-634.
    • (1995) Biochem Mol Biol Int , vol.35 , pp. 627-634
    • Hattori, A.1    Migitaka, H.2    Masayake, I.3
  • 6
    • 0030723483 scopus 로고    scopus 로고
    • Melatonin as a therapeutic agent in the treatment of sleep disturbance in depression
    • DE VRIES MW, PEETERS FP. Melatonin as a therapeutic agent in the treatment of sleep disturbance in depression. J Nerv Ment Dis 1997; 185:201-202.
    • (1997) J Nerv Ment Dis , vol.185 , pp. 201-202
    • De Vries, M.W.1    Peeters, F.P.2
  • 7
    • 0030278981 scopus 로고    scopus 로고
    • Use of melatonin in the treatment of paediatric sleep disorders
    • JAN JE, O'DONNELL ME. Use of melatonin in the treatment of paediatric sleep disorders. J Pineal Res 1996; 21:193-199.
    • (1996) J Pineal Res , vol.21 , pp. 193-199
    • Jan, J.E.1    O'Donnell, M.E.2
  • 8
    • 0028990931 scopus 로고
    • Improvement of sleep quality in elderly people by controlled release melatonin
    • GARFINKEL D, LAUDON M, NOF D et al. Improvement of sleep quality in elderly people by controlled release melatonin. Lancet 1995; 346:541-544.
    • (1995) Lancet , vol.346 , pp. 541-544
    • Garfinkel, D.1    Laudon, M.2    Nof, D.3
  • 9
    • 0024342306 scopus 로고
    • Central melatonin receptors: Implication for a mode of action
    • MORGAN PJ, WILLIAMS LM. Central melatonin receptors: implication for a mode of action. Experientia 1989; 45:955.
    • (1989) Experientia , vol.45 , pp. 955
    • Morgan, P.J.1    Williams, L.M.2
  • 10
    • 0242344471 scopus 로고    scopus 로고
    • Office of Orphan Products Development, Food and Drug Administration, Rockville, MD, last rev August
    • LIST OF ORPHAN DRUG DESIGNATION AND APPROVAL. Office of Orphan Products Development, Food and Drug Administration, Rockville, MD, last rev August 2002.
    • (2002) List of Orphan Drug Designation and Approval
  • 11
    • 0031942551 scopus 로고    scopus 로고
    • Melatonin and its physiological and therapeutic properties
    • NOWAK JZ, ZAWILSKA JB. Melatonin and its physiological and therapeutic properties. Pharm World Sci 1998; 20:18-27.
    • (1998) Pharm World Sci , vol.20 , pp. 18-27
    • Nowak, J.Z.1    Zawilska, J.B.2
  • 12
    • 0030279370 scopus 로고    scopus 로고
    • Melatonin supplements for aging
    • SANDYK R. Melatonin supplements for aging. Int J Neurosci 1996; 87:219-224.
    • (1996) Int J Neurosci , vol.87 , pp. 219-224
    • Sandyk, R.1
  • 13
    • 0242281226 scopus 로고    scopus 로고
    • Oxidative mediated neurodegeneration in Alzheimer's disease: Melatonin and related antioxidants as neuroprotective agents
    • PAPPOLLA MA, REITER RJ, BRYANT-THOMAS TK et al. Oxidative mediated neurodegeneration in Alzheimer's disease: melatonin and related antioxidants as neuroprotective agents. Curr Med Chem 2003; 3:233-243.
    • (2003) Curr Med Chem , vol.3 , pp. 233-243
    • Pappolla, M.A.1    Reiter, R.J.2    Bryant-Thomas, T.K.3
  • 14
    • 0030025155 scopus 로고    scopus 로고
    • Increased survival time in brain glioblastomas by a radioneuroendocrine strategy with radiotherapy plus melatonin compared to radiotherapy alone
    • LISSONI P, MEREGALLI S, NASETTO L et al. Increased survival time in brain glioblastomas by a radioneuroendocrine strategy with radiotherapy plus melatonin compared to radiotherapy alone. Oncology 1996; 53:43-46.
    • (1996) Oncology , vol.53 , pp. 43-46
    • Lissoni, P.1    Meregalli, S.2    Nasetto, L.3
  • 15
    • 0029126045 scopus 로고
    • A biological study on the efficacy of low-dose subcutaneous interleukin-2 plus melatonin in the treatment of cancer-related thrombocytopenia
    • LISSONI P, BARNI S, BRIVIO F et al. A biological study on the efficacy of low-dose subcutaneous interleukin-2 plus melatonin in the treatment of cancer-related thrombocytopenia. Oncology 1995; 52:360-362.
    • (1995) Oncology , vol.52 , pp. 360-362
    • Lissoni, P.1    Barni, S.2    Brivio, F.3
  • 16
    • 0028934479 scopus 로고
    • Randomized study of low-dose subcutaneous interleukin-2 plus melatonin versus supportive care alone in metastatic colorectal cancer patients progressing under 5-fluorouracil and folates
    • BARNI S, LISSONI P, CAZZANIGA M et al. Randomized study of low-dose subcutaneous interleukin-2 plus melatonin versus supportive care alone in metastatic colorectal cancer patients progressing under 5-fluorouracil and folates. Oncology 1995; 52:243-245.
    • (1995) Oncology , vol.52 , pp. 243-245
    • Barni, S.1    Lissoni, P.2    Cazzaniga, M.3
  • 17
    • 0028219170 scopus 로고
    • Low-dose interleukin-2 subcutaneous immunotherapy in association with the pineal hormone melatonin as a first-line therapy in locally advanced or metastatic hepatocellular carcinoma
    • ALDEGHI R, LISSONI P, BARNI SL et al. Low-dose interleukin-2 subcutaneous immunotherapy in association with the pineal hormone melatonin as a first-line therapy in locally advanced or metastatic hepatocellular carcinoma. Eur J Cancer 1994; 30:167-170.
    • (1994) Eur J Cancer , vol.30 , pp. 167-170
    • Aldeghi, R.1    Lissoni, P.2    Barni, S.L.3
  • 18
    • 0030752296 scopus 로고    scopus 로고
    • Melatonin in relation to cellular antioxidative defence mechanisms
    • REITER RJ, CARNEIRO RCG, OH CS. Melatonin in relation to cellular antioxidative defence mechanisms. Horm Metab Res 1997; 29:343-392.
    • (1997) Horm Metab Res , vol.29 , pp. 343-392
    • Reiter, R.J.1    Carneiro, R.C.G.2    Cs, O.H.3
  • 19
    • 0002979059 scopus 로고
    • A potent endogenous hydroxyl radical scavenger
    • TAN DX, CHEN LD, POEGGLER B et al. A potent endogenous hydroxyl radical scavenger. Endocr J 1993; 1:57-60.
    • (1993) Endocr J , vol.1 , pp. 57-60
    • Tan, D.X.1    Chen, L.D.2    Poeggler, B.3
  • 20
    • 0028983511 scopus 로고
    • Melatonin protects human blood lymphocytes from radiation-induced chromosome damage
    • VIJAYALAXMI BZ, REITER RJ, SEWERYNEK E et al. Melatonin protects human blood lymphocytes from radiation-induced chromosome damage. Mutat Res 1995; 346:23-31.
    • (1995) Mutat Res , vol.346 , pp. 23-31
    • Vijayalaxmi, B.Z.1    Reiter, R.J.2    Sewerynek, E.3
  • 21
    • 0030755902 scopus 로고    scopus 로고
    • Reaction of melatonin with lipoperxyl radicals in phospholipid bilayers
    • LIVREA MA, TESORIERE L, D'ARPA D et al. Reaction of melatonin with lipoperxyl radicals in phospholipid bilayers. Free Rad Biol Med 1997; 23:706-711.
    • (1997) Free Rad Biol Med , vol.23 , pp. 706-711
    • Livrea, M.A.1    Tesoriere, L.2    D'Arpa, D.3
  • 22
    • 1542312038 scopus 로고    scopus 로고
    • Evaluation of the antioxidant activity of melatonin in vitro
    • MARSHALL KA, REITER RJ, POEGGELER B et al. Evaluation of the antioxidant activity of melatonin in vitro. Free Rad Biol Med 1996; 21:307-315.
    • (1996) Free Rad Biol Med , vol.21 , pp. 307-315
    • Marshall, K.A.1    Reiter, R.J.2    Poeggeler, B.3
  • 24
    • 0032706865 scopus 로고    scopus 로고
    • 2: Evidence for a free radical mechanism
    • 2: evidence for a free radical mechanism. J Am Chem Soc 1999; 121:9738-9739.
    • (1999) J Am Chem Soc , vol.121 , pp. 9738-9739
    • Uppu, R.1    Prior, W.A.2
  • 25
    • 0014218466 scopus 로고
    • Acute pharmacology of melatonin
    • BARCHAS J, DA COSTA F, SPECTOR S. Acute pharmacology of melatonin. Nature 1967; 214:919-920.
    • (1967) Nature , vol.214 , pp. 919-920
    • Barchas, J.1    Da Costa, F.2    Spector, S.3
  • 26
    • 12244304145 scopus 로고    scopus 로고
    • The chemistry of melatonin's interaction with reactive species
    • ALLEGRA M, REITER RJ, TAN DX et al. The chemistry of melatonin's interaction with reactive species. J Pineal Res 2003; 34:1-10.
    • (2003) J Pineal Res , vol.34 , pp. 1-10
    • Allegra, M.1    Reiter, R.J.2    Tan, D.X.3
  • 27
    • 0025758136 scopus 로고
    • Pineal melatonin: Cell biology of its synthesis and of its physiological interaction
    • REITER RJ. Pineal melatonin: cell biology of its synthesis and of its physiological interaction. Endocrine Rev 1991; 12:151-180.
    • (1991) Endocrine Rev , vol.12 , pp. 151-180
    • Reiter, R.J.1
  • 28
    • 0023193395 scopus 로고
    • A Cyclic isomer of 2-hydroxymelatonin: A novel metabolite of melatonin
    • VAKKURI O, TERVO J, LUTTINEN R et al. A Cyclic isomer of 2-hydroxymelatonin: a novel metabolite of melatonin. Endocrinology 1987; 120:2453-2459.
    • (1987) Endocrinology , vol.120 , pp. 2453-2459
    • Vakkuri, O.1    Tervo, J.2    Luttinen, R.3
  • 29
    • 0032583461 scopus 로고    scopus 로고
    • A novel melatonin metabolite, cyclic 3-hydroxymelatonin: A biomarker of in vivo hydroxyl radical generation
    • TAN DX, MANCHESTER LC, REITER RJ et al. A novel melatonin metabolite, cyclic 3-hydroxymelatonin: a biomarker of in vivo hydroxyl radical generation. Biochim Biophys Res Commun 1998; 253:614-620.
    • (1998) Biochim Biophys Res Commun , vol.253 , pp. 614-620
    • Tan, D.X.1    Manchester, L.C.2    Reiter, R.J.3
  • 30
    • 0033551120 scopus 로고    scopus 로고
    • Identification of the factors affecting the rate of deactivation of hypochlorous acid by melatonin
    • DELLEGAR SM, MURPHY SA, BOURNE AE et al. Identification of the factors affecting the rate of deactivation of hypochlorous acid by melatonin. Biochem Biophys Res Commun 1999; 257:431-439.
    • (1999) Biochem Biophys Res Commun , vol.257 , pp. 431-439
    • Dellegar, S.M.1    Murphy, S.A.2    Bourne, A.E.3
  • 31
    • 0035695301 scopus 로고    scopus 로고
    • Oxidation of melatonin by oxoferryl hemoglobin: A mechanistic study
    • TESORIERE L, AVELLONE G, CERAULO L et al. Oxidation of melatonin by oxoferryl hemoglobin: a mechanistic study. Free Radical Research 2001; 35:633-642.
    • (2001) Free Radical Research , vol.35 , pp. 633-642
    • Tesoriere, L.1    Avellone, G.2    Ceraulo, L.3
  • 32
    • 0032979082 scopus 로고    scopus 로고
    • Interactions of melatonin with membrane models: Portioning of melatonin in AOT and Lecithin Reversed Micelles
    • CERAULO L, FERRUGIA M, TESORIERE L et al. Interactions of melatonin with membrane models: portioning of melatonin in AOT and Lecithin Reversed Micelles. J Pineal Res 1999; 26:108-112.
    • (1999) J Pineal Res , vol.26 , pp. 108-112
    • Ceraulo, L.1    Ferrugia, M.2    Tesoriere, L.3
  • 33
    • 0037123166 scopus 로고    scopus 로고
    • Structural and physicochemical characterization of the inclusion complexes of cyclomaltooligosaccharides (cyclodextrins) with melatonin
    • BONGIORNO D, CERAULO L, MELE A et al. Structural and physicochemical characterization of the inclusion complexes of cyclomaltooligosaccharides (cyclodextrins) with melatonin. Carbohydr Res 2002; 337:743-754.
    • (2002) Carbohydr Res , vol.337 , pp. 743-754
    • Bongiorno, D.1    Ceraulo, L.2    Mele, A.3
  • 34
    • 0035193189 scopus 로고    scopus 로고
    • Guest-to-host-proton transfer in melatonin-beta-cyclodextrin inclusion complex by ionspray, fast atom bombardament and tandem mass spectrometry
    • BONGIORNO D, CERAULO L, MELE A et al. Guest-to-host-proton transfer in melatonin-beta-cyclodextrin inclusion complex by ionspray, fast atom bombardament and tandem mass spectrometry. J Mass Spectrom 2001; 36:1189-1194.
    • (2001) J Mass Spectrom , vol.36 , pp. 1189-1194
    • Bongiorno, D.1    Ceraulo, L.2    Mele, A.3
  • 36
    • 0031790130 scopus 로고    scopus 로고
    • Metastable ion studies in the characterization of melatonin isomers
    • DIAMANTINI G, TARZIA G, SPADONI G et al. Metastable ion studies in the characterization of melatonin isomers. Rapid Commun Mass Spectrom 1998; 12:1538-1542.
    • (1998) Rapid Commun Mass Spectrom , vol.12 , pp. 1538-1542
    • Diamantini, G.1    Tarzia, G.2    Spadoni, G.3
  • 37
    • 0242375931 scopus 로고
    • Properties and reactions of indoles isoindoles, and their hydrogenated derivatives
    • Weissberger A, Taylor EC, eds, John Wiley & Sons, New York
    • th Volume: Indoles Part I. Weissberger A, Taylor EC, eds, John Wiley & Sons, New York, 1972; pp. 3-5.
    • (1972) th Volume: Indoles Part I , pp. 3-5
    • Remers, W.A.1
  • 38
    • 0037369749 scopus 로고    scopus 로고
    • Melatonin effects on bone: Experimental facts and clinical perspectives
    • CARDINALI DP, LADIEZESKY MG, BOGGIO V et al. Melatonin effects on bone: experimental facts and clinical perspectives. J Pineal Res 2003; 34:81-87.
    • (2003) J Pineal Res , vol.34 , pp. 81-87
    • Cardinali, D.P.1    Ladiezesky, M.G.2    Boggio, V.3
  • 39
    • 0037378182 scopus 로고    scopus 로고
    • The utility of melatonin in reducing cerebral damage resulting from ischemia and reperfusion
    • CHEUNG TF. The utility of melatonin in reducing cerebral damage resulting from ischemia and reperfusion. J Pineal Res 2003; 34:153-160.
    • (2003) J Pineal Res , vol.34 , pp. 153-160
    • Cheung, T.F.1
  • 40
    • 0036829769 scopus 로고    scopus 로고
    • Myocardial ischemia-reperfusion in rats: Reduction of infarct size by either supplemental physiological or pharmacological doses of melatonin
    • SAHNA E, ACET A, OZER MK et al. Myocardial ischemia-reperfusion in rats: reduction of infarct size by either supplemental physiological or pharmacological doses of melatonin. J Pineal Res 2002; 33:234-238.
    • (2002) J Pineal Res , vol.33 , pp. 234-238
    • Sahna, E.1    Acet, A.2    Ozer, M.K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.