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The primary product from AFMK (1) is N-(1-formyl-5-methoxy-3- oxo-2,3-dihydro-1H-indol-2-ylidenemethyl)-acetamide (2), which is obtained after purification as E- and Z-isomers (2a, 2b); a secondary product has been identified as N-(1-formyl-2-hydroxy-5-methoxy-3-oxo-2,3-dihydro-1H-indol- 2-ylmethyl)-acetamide (3). When H2O2 is added to the ABTS•+ reaction mixture in quantities not already leading to substantial reduction of thisradical, compound 3 is isolated as the major product, whereas 2a and 2b are virtually absent. The substances formed differ from all previously knownoxidation products which derive from melatonin and are, among these, the first 3-indolinones. 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  1. University of Yangon
  2. Department of Chemistry

Interactions of melatonin and its metabolites with the ABTS cation radical: extension of the radical scavenger cascade and formation of a novel class of oxidation products, C2-substituted 3-indolinones

http://hdl.handle.net/20.500.12678/0000002188
http://hdl.handle.net/20.500.12678/0000002188
ad3cad4e-4fbe-447a-9919-e46a177ec50a
f0c351bb-19d2-4b26-979b-c20a839533ef
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Publication type
Journal article
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Publication
Title
Title Interactions of melatonin and its metabolites with the ABTS cation radical: extension of the radical scavenger cascade and formation of a novel class of oxidation products, C2-substituted 3-indolinones
Language en
Publication date 2006
Authors
Rosen, Joachim
Ni Ni Than
Koch, Dorothea
Poeggeler, Burkhard
Laatsch, Hartmut
Hardelan, Ru¨diger
Description
Melatonin had previously been shown to reduce up to four 2, 2'- azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid) cation radicals (ABTS•+) via a scavenger cascade ending with N1-acetyl-N2-formyl-5- methoxykynuramine (AFMK). However, when melatonin is added to the reaction system in much lower quantities than ABTS•+, the number of radicals scavenged per melatonin molecule is considerably higher and can attain a value of ten. Under conditions allowing for such a stoichiometry, novel products have been detected which derive from AFMK (1). These were separated by repeated chromatography and the major compounds were characterized by spectroscopic methods, such as mass spectrometry (HPLCMS, EI-MS and ESI-HRMS), 1H nuclear magnetic resonance (NMR) and
13C NMR, heteronuclear multiple bond connectivity (HMBC) correlations. The identified substances are formed by re-cyclization and represent 3- indolinones carrying the side chain at C2; the N-formyl group can be maintained, but deformylated analogs seem to be also generated, according to MS. The primary product from AFMK (1) is N-(1-formyl-5-methoxy-3- oxo-2,3-dihydro-1H-indol-2-ylidenemethyl)-acetamide (2), which is obtained after purification as E- and Z-isomers (2a, 2b); a secondary product has been identified as N-(1-formyl-2-hydroxy-5-methoxy-3-oxo-2,3-dihydro-1H-indol- 2-ylmethyl)-acetamide (3). When H2O2 is added to the ABTS•+ reaction mixture in quantities not already leading to substantial reduction of thisradical, compound 3 is isolated as the major product, whereas 2a and 2b are virtually absent. The substances formed differ from all previously knownoxidation products which derive from melatonin and are, among these, the first 3-indolinones. Moreover, the aliphatic side chain at C2 is reminiscent of other substances which have been synthesized in the search for melatonin receptor ligands.
Keywords
ABTS
Identifier https://uyr.uy.edu.mm/handle/123456789/981
Journal articles
Journal of Pineal Research
41
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