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

被引:20
作者
Agozzino, P
Avellone, G
Bongiorno, D
Ceraulo, L
Filizzola, F
Natoli, MC
Livrea, MA
Tesoriere, L
机构
[1] Dipartimento Chim & Tecnol Farmaceut, Palermo, Italy
[2] Dipartimento Chim Organ E Paterno, Palermo, Italy
[3] Dipartimento Farmacochim Tossicol & Biol, Palermo, Italy
关键词
1D and 2D nuclear magnetic resonance; mass spectra; melatonin; metabolites; structure;
D O I
10.1034/j.1600-079X.2003.00086.x
中图分类号
R5 [内科学];
学科分类号
1002 ; 100201 ;
摘要
Oxidation of melatonin by Fenton reagents as well as with hypochlorous acid or oxoferryl hemoglobin has been investigated. Analysis of products by low resolution/mass spectra ( MS), high resolution/MS, H-1-nuclear magnetic resonance (NMR), C-13-NMR, correlated spectroscopy ( COSY) and heterocorrelated spectroscopy (HETCOR) 2D NMR reveals the formation of a single mono-oxygenated product under all conditions and unequivocally assigns the N-[2-(5-methoxy-2-oxo-2,3-dihydro-1H-indol-3- yl)-ethyl]-acetamide structure, which had not been previously considered.
引用
收藏
页码:269 / 275
页数:7
相关论文
共 41 条
[1]   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 [J].
ALDEGHI, R ;
LISSONI, P ;
BARNI, S ;
ARDIZZOIA, A ;
TANCINI, G ;
PIPERNO, A ;
POZZI, M ;
RICCI, G ;
CONTI, A ;
MAESTRONI, GJM .
EUROPEAN JOURNAL OF CANCER, 1994, 30A (02) :167-170
[2]   The chemistry of melatonin's interaction with reactive species [J].
Allegra, M ;
Reiter, RJ ;
Tan, DX ;
Gentile, C ;
Tesoriere, L ;
Livrea, MA .
JOURNAL OF PINEAL RESEARCH, 2003, 34 (01) :1-10
[3]   ACUTE PHARMACOLOGY OF MELATONIN [J].
BARCHAS, J ;
DACOSTA, F ;
SPECTOR, S .
NATURE, 1967, 214 (5091) :919-&
[4]  
BARNI S, 1995, ONCOLOGY, V52, P243
[5]   Structural and physicochemical characterization of the inclusion complexes of cyclomaltooligosaccharides (cyclodextrins) with melatonin [J].
Bongiorno, D ;
Ceraulo, L ;
Mele, A ;
Panzeri, W ;
Selva, A ;
Liveri, VT .
CARBOHYDRATE RESEARCH, 2002, 337 (08) :743-754
[6]   Guest-to-host proton transfer in melatonin-β-cyclodextrin inclusion complex by ionspray, fast atom bombardment and tandem mass spectrometry [J].
Bongiorno, D ;
Ceraulo, L ;
Mele, A ;
Panzeri, W ;
Selva, A ;
Liveri, VT .
JOURNAL OF MASS SPECTROMETRY, 2001, 36 (11) :1189-1194
[7]   Melatonin effects on bone: experimental facts and clinical perspectives [J].
Cardinali, DP ;
Ladizesky, MG ;
Boggio, V ;
Cutrera, RA ;
Mautalen, C .
JOURNAL OF PINEAL RESEARCH, 2003, 34 (02) :81-87
[8]   Interactions of melatonin with membrane models: Portioning of melatonin in AOT and lecithin reversed micelles [J].
Ceraulo, L ;
Ferrugia, M ;
Tesoriere, L ;
Segreto, S ;
Livrea, MA ;
Liveri, T .
JOURNAL OF PINEAL RESEARCH, 1999, 26 (02) :108-112
[9]   The utility of melatonin in reducing cerebral damage resulting from ischemia and reperfusion [J].
Cheung, RTF .
JOURNAL OF PINEAL RESEARCH, 2003, 34 (03) :153-160
[10]   Identification of the factors affecting the rate of deactivation of hypochlorous acid by melatonin [J].
Dellegar, SM ;
Murphy, SA ;
Bourne, AE ;
DiCesare, JC ;
Purser, GH .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1999, 257 (02) :431-439