Bisabolane-type sesquiterpenes from Vernonia amygdalina: Absolute configuration and anti-inflammatory activity

The phytochemical assessment of Vernonia amygdalina resulted in the isolation and identification of seven undescribed bisabolane-type sesquiterpenes designated amygdanoids A-G and one known analogue. This is the first report of this type of sesquiterpene from V. amygdalina. Their structures, including the absolute configurations, were elucidated by comprehensive analysis with HRESIMS, 1D and 2D NMR, quantum chemical calculations of NMR and electronic circular dichroism (ECD), modified Mosher's method, and the in situ dimolybdenum CD method. The anti-inflammatory activity of the isolates was evaluated. All the isolated compounds clearly inhibited the production of NO and the expression of the iNOS protein. Secretion of the COX-2 protein was constrained by amygdanoids A-F. Further investigation suggested that amygdanoids E exhibited anti-inflammatory activity by suppressing the expression of iNOS and COX-2 as well as the PI3K/AKT/NF-κB signaling pathway.