Atrachinenins D–S, Novel Meroterpenoids with Geranyl Hydroquinone Moiety from Atractylodes Chinensis by the LC/MS-Based Molecular Decoy and Targeted Isolation

Abstract

To mine fascinating molecules from the rhizomes of Atractylodes chinensis, the known molecular formula of atrachinenin A was used as a bait to search LC-HRMS data in different subfractions. Sixteen new meroterpenoids, atrachinenins D–S (1–16) including three unprecedented carbon skeletons (1–5) and eleven new oxygen-bridged hybrids (6–16) were obtained by the targeted isolation. Their structures and absolute configurations were elucidated by the spectroscopic data and electronic circular dichroism (ECD) calculations. All of the isolated compounds were evaluated for their inhibitory activity of NO production and compounds 1, 4, and 8 showed moderate anti-inflammatory activity. The proposed biosynthetic pathways of 1–5 were also discussed.

Keywords: Atractylodes chinensis, Atrachinenins D-S, Meroterpenoids, Geranyl hydroquinone, Molecular decoy, NO inhibition