Sesquiterpenes from Neurolaena lobata and their antiproliferative and anti-inflammatory activities.

ABSTRACT: Five new sesquiterpenes, neurolobatin A (1), neurolobatin B (2), 5?-hydroxy-8?-isovaleroyloxy-9?-hydroxycalyculatolide (3), 3-epi-desacetylisovaleroylheliangine (4), and 3?-acetoxy-8?-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-?-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.

SUBMITTER: Lajter I 

PROVIDER: S-EPMC3971758 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature