The structure of roxburghines A-E, new indole alkaloids from an Uncaria Sp.
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Biomedical subjects
Publications and source records attributed to M Hesse.
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Several polyamine derivatives were synthesized in order to produce novel antagonists of muscular nicotinic acetylcholine receptors. Their affinities were compared with those of philanthotoxin PhTX-343.
The low molecular mass fraction of the venom of the spider Latrodectus menavodi, a black widow spider domiciled in Madagascar, was analyzed with HPLC combined with electrospray mass spectrometry as lyophilized powder and as freshly milked liquid venom. The main components were found to be the purine derivatives adenosine (1), guanosine (2), inosine (3), and 2,4,6-trihydroxypurine (4). Compounds 1-3 are known as components of spider or snake venoms, but they have never been found previously in the venom of the species Latrodectus, whereas compound 4 has not previously been found in any spider venoms. The lyophilized and unlyophilized venoms were found to have identical composition.
A new hydroxycinnamoyl polyamine derivative, N,N',N"-triferuloylspermidine (= (E)-N-(4-aminobutyl) -3,3',3"-tris(4-hydroxy-3-methoxyphenyl)-N,N',N"- (butane-1,4-diyl)tris [prop-2-enamide]) (1) was detected in the H2O/MeOH extract of pollen from Hippeastrum x hortorum. The compound was identified by on-line-coupled high-performance liquid chromatography and atmospheric-pressure chemical-ionization mass spectrometry (HPLC-UV(DAD)/APCI-MS and MS/MS). The structure was proven by comparing the HPLC/MS data after UV-induced (E) <==> (Z) photoisomerization and catalytic hydrogenation of the natural compound and the synthetic reference compound. This is the first report of a triferuloylspermidine in nature.
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