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J Nat Prod ; 77(3): 576-82, 2014 Mar 28.
Article de Anglais | MEDLINE | ID: mdl-24476550

RÉSUMÉ

Five new sesquiterpenes, neurolobatin A (1), neurolobatin B (2), 5ß-hydroxy-8ß-isovaleroyloxy-9α-hydroxycalyculatolide (3), 3-epi-desacetylisovaleroylheliangine (4), and 3ß-acetoxy-8ß-isovaleroyloxyreynosin (5), were isolated from the aerial parts of Neurolaena lobata. The structures were established by means of a combined spectroscopic data analysis, including ESIMS, APCI-MS, and 1D- and 2D-NMR techniques. Neurolobatin A (1) and B (2) are unusual isomeric seco-germacranolide sesquiterpenes with a bicyclic acetal moiety, compounds 3 and 4 are unsaturated epoxy-germacranolide esters, and compound 5 is the first eudesmanolide isolated from the genus Neurolaena. The isolated compounds (1-5) were shown to have noteworthy antiproliferative activities against human tumor cell lines (A2780, A431, HeLa, and MCF7). The anti-inflammatory effects of 1-5, evaluated in vitro using LPS- and TNF-α-induced IL-8 expression inhibitory assays, revealed that all these compounds strongly down-regulated the LPS-induced production of IL-8 protein, with neurolobatin B (2) and 3-epi-desacetylisovaleroylheliangine (4) being the most effective.


Sujet(s)
Antinéoplasiques d'origine végétale/isolement et purification , Antinéoplasiques d'origine végétale/pharmacologie , Asteraceae/composition chimique , Sesquiterpènes de type germacrane/isolement et purification , Sesquiterpènes de type germacrane/pharmacologie , Antinéoplasiques d'origine végétale/composition chimique , Tests de criblage d'agents antitumoraux , Femelle , Guatemala , Cellules HeLa , Humains , Interleukine-8/métabolisme , Lipopolysaccharides/pharmacologie , Structure moléculaire , Résonance magnétique nucléaire biomoléculaire , Sesquiterpènes de type germacrane/composition chimique , Facteur de nécrose tumorale alpha/pharmacologie , Veines ombilicales/cytologie , Veines ombilicales/effets des médicaments et des substances chimiques
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