Cnidimonins A–C, Three Types of Hybrid Dimer from <i>Cnidium monnieri</i>: Structural Elucidation and Semisynthesis

Abstract

Three pairs of racemic dimers, (±)-cnidimonins A-C (1-3), were isolated from the fruits of Cnidium monnieri. They represent novel hybrid-dimerization patterns of coumarin skeleton with structurally diverse units (flavonol, benzofuran, and chromone) via an unprecedented terminal chiral carbon of prenyl. The absolute configurations of the enantiomers were determined by electronic circular dichroism (ECD). To investigate their bioactivities in depth, (±)-cnidimonins A-C (1-3) were synthesized. The racemic mixture (±)-1 exhibited stronger antiviral activity against HSV-1 (IC₅₀: 1.23 μM) than its corresponding optically pure enantiomers.