Oleanane-type triterpenoids from Sabia limoniacea and their anti-inflammatory activities.

Eighteen new oleanane-type triterpenoids were isolated from the stems of Sabia limoniacea, including sabialimon A (1), a triterpenoid with an unprecedented 6/6/6/7/7 pentacyclic skeleton and seventeen undescribed triterpenoids, sabialimons B-R (2 - 18), along with six previously described analogs (19 - 24). Their structures were fully elucidated via extensive spectroscopic analysis including 1D and 2D NMR, high-resolution electrospray ionization mass spectrometry (HRESIMS), experimental electronic circular dichroism measurements and X-ray crystallographic studies. Compound 1 is the first triterpenoid that possesses a rare ring system (6/6/6/7/7) with an oxygen-bearing bridge between C-17 and C-18 and a hemiketal form at C-17, which is generated a larger ring by the degradation of C-28 and D/E-ring expansion. Biological evaluation revealed that sabialimon I (9), sabialimon K (11), sabialimon P (16) and 11,13(18)-oleanadien-28-hydroxymethyl 3-one (20) exhibited significantly inhibitory activities against nitric oxide (NO) release with IC50 values of 29.65, 23.41, 18.12 and 26.64 µM, respectively, as compared with the positive control (dexamethasone, IC50 value: 40.35 µM). Furthermore, sabialimon P markedly decreased the secretion of TNF-α, iNOS, IL-6 and NF-κB and inhibited the expression of COX-2 and NF-κB/p65 in LPS-induced RAW264.7 cells in a dose-dependent manner.

Megastigmane glycoside and phenol glycosides from the bark of Mallotus barbatus.

A new megastigmane glycoside, barbatcoside A (1), and two new phenol glycosides, barbatcosides B (2) and C (3), together with eight known compounds (4-11) were isolated from the bark of Mallotus barbatus Müll. Arg. Their structures were elucidated using extensive 1D and 2D NMR as well as HRESIMS spectroscopic data. The stereochemistry of compounds 1 and 2 were established based on the experimental CD curves. The anti-inflammatory activities of compounds 1-11 from M. barbatus were evaluated using LPS-stimulated RAW 264.7 cell models. Compounds 2 and 3 substantially inhibited the release of NO with IC50 values of 34.78 µM and 20.73 µM, respectively.