Anti-inflammatory secondary metabolites from the leaves of Rosa laevigata

Bioassay-guided fractionation of a n-BuOH-soluble extract of the leaves of Rosa laevigata led to the isolation of three new 19-oxo-18,19-seco-ur-sane-type triterpenoids, laevigins A−C (1−3), a new oleanane-type triterpenoid saponin, laevigin D (4), a new geranylmethylbenzoate, 5-[(2″E,6″S)-6″,7″-dihydroxy-3″,7″-dimethyl-2″-octen-1″-yl]-2-(β-d-glucopyranosyloxy)-methyl benzoate (5), together with 9 known compounds (6−14). Their structures were elucidated by spectroscopic and chemical methods. Compounds 4, 9, 11, and 12 significantly suppressed the LPS-stimulated NF-κB transcriptional activity and the release of TNFα, IL-1β, IL-6, and IL-10 in mouse RAW 264.7 macrophages. The compound 12 exhibited moderate inhibition on NF-κB transcriptional activity with an IC50 value of 23.21 μM. The IC50 values of compound 12 were measured as 14.32, 8.53, 8.04, and 10.38 μM for the inhibitory activity on TNFα-release, IL-1β-release, IL-6-release, and IL-10-release, respectively.