Structurally Diverse Sesquiterpenoid Glycoside Esters from Pittosporum qinlingense with Anti-neuroinflammatory Activity

Thirteen new sesquiterpenoid glycoside esters, including 11 aromadendrane-type compounds, pitqinlingosides A-K (1-11), one cadinane-type compound, pitqinlingoside L (12), and one eudesmane-type compound, pitqinlingoside M (13), together with seven known analogues (14-20) were isolated from the twigs, fruits, and leaves of Pittosporum qinlingense. Structures were elucidated by analysis of spectroscopic data, gas chromatography mass spectrometry (GC-MS), and chemical methods. The absolute configuration was confirmed by single-crystal X-ray crystallography analysis or electronic circular dichroism spectra. Unusual glycoside esters are characterized by the presence of polyacylated β-d-fucopyranosyl, β-d-glucopyranosyl, and β-d-xylopyranosyl units. Pitqinlingosides A (1), B (2), D (4), and F (6), pittosporanoside A₁ acetate (14), and pittosporanoside A₁ (16) showed significant nitric oxide production inhibition in lipopolysaccharide (LPS)-induced BV-2 microglial cells with IC₅₀ values ranging from 0.95 to 24.12 μM. Structure-activity relationships of the isolated compounds are discussed.