Anti-inflammatory flavonoid derivatives from the heartwood of Dalbergia odorifera T. Chen

Two pairs of flavonoid enantiomers (1a/1b and 2a/2b) together with three known analogues (3–5) were isolated from the heartwood of Dalbergia odorifera T. Chen. Their structures were elucidated by extensive spectroscopic analysis (1 D and 2 D NMR, UV, IR, and HRMS) and experimental and calculated ECD data. Compound 2 features an unusual 2-methyl-3(2H)-furanone moiety forming the C-ring of flavonoid, and its putative biosynthetic pathway is also proposed. Compounds 3‒5 exhibited significant inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells with IC50 values of 14.7 ± 0.3 μM, 40.2 ± 1.1 μM, and 3.2 ± 0.1 μM, respectively.