Chlorine-containing guaianolide sesquiterpenoids from Achillea millefolium L. with inhibitory effects against LPS-induced NO release in BV-2 microglial cells

Chlorine-containing guaianolide sesquiterpenoids are rare natural compounds that are mainly derived from plants of the Asteraceae family. Our previous investigations on the whole plant of Achillea millefolium L. resulted in the discovery of two chlorine-containing guaianolide sesquiterpenoids. In the present study, a LC‒MS tracking strategy based on the characteristic isotropic peak of atomic chlorine was employed to isolate nine undescribed chlorine-containing guaianolide sesquiterpenoids, Millefolactons B1–B9, from A. millefolium L.. The structures of these compounds were elucidated by spectroscopic data analysis, and the corresponding absolute configurations were determined by single-crystal X-ray crystallography and ECD data analysis. Millefolactons B2–B7 displayed inhibitory activities against LPS-induced NO release in BV-2 microglial cells.