Chinese olive is a well-known fruit in China. In this study, we explored anti-inflammatory phytochemicals of Chinese olive fruit, which led to the isolation of nine pairs of new enantiomers of benzofuran neolignans (1a/1b-9a/9b). Among them, the planar structures of compounds 1-3 were undescribed previously, and the absolute configurations of all compounds were reported first. Their stereostructures were elucidated on the basis of the interpretation of NMR, HRESIMS, and electronic circular dichroism (ECD) data, as well as ECD calculation. All compounds exhibited pronounced inhibitory effects on lipopolysaccharide-induced nitric oxide (NO) production in RAW 264.7 macrophages with IC50 values ranging from 6.0 to 30.2 μM. Furthermore, compounds 6a and 6b exert anti-inflammatory effects by blocking the nuclear translocation of NF-κB, thereby reducing the expression of pro-inflammatory mediators COX-2, iNOS, IL-1β, and IL-6. This study could provide some guidance and evidence to the further development and utilization of the Chinese olive.
Keywords: Canarium album (Lour.) Rauesch; Chinese olive; anti-inflammatory; benzofuran neolignans; enantiomers.