ABSTRACT
Chemical examination of the methanolic extract from the stem bark of Daphne aurantiaca led to the isolation of two innovanoside dimers (1 and 2) with an unusual four-membered cyclobutane ring, together with the isoinnovanoside 3. Their chemical structures and configurations were elucidated by extensive spectral analysis and synthesis.
Subject(s)
Cyclobutanes/chemical synthesis , Daphne/chemistry , Glucosides/chemical synthesis , Plant Extracts/chemical synthesis , Pyrones/chemical synthesis , Crystallography, X-Ray , Cyclobutanes/chemistry , Cyclobutanes/isolation & purification , Dimerization , Glucosides/chemistry , Glucosides/isolation & purification , Models, Molecular , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Pyrones/chemistry , Pyrones/isolation & purificationABSTRACT
The inhibitory activity of 4,4'-dihydroxy-α-truxillic acid and its derivatives (5-1a-5-35a) on nitric oxide (NO) release was evaluated in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Compounds 5-3a, 5-4a, 5-5a, 5-10a, 5-24a, 5-26a and 5-30a exhibited significant inhibitory effects on NO production, with IC50 values of 19.8, 21.1, 16.4, 17.5, 20.8, 22.6 and 17.6 µM, respectively. Their cytotoxicities were also estimated using a CCK-8 assay. Among them, compound 5-10a showed no cytotoxic effect on cells up to a concentration of 50 µM. The structure-activity relationships of the compounds are also discussed.
