Organic Letters
Organic Letters
5 years ago

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

Cnidimonins A–C, Three Types of Hybrid Dimer from Cnidium monnieri: Structural Elucidation and Semisynthesis
Li Li, Shuanggang Ma, Fangyi Su, Yuhuan Li, Yunbao Liu, Shishan Yu, Yong Li, Jing Qu, Rubing Wang, Zheng Zhao
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02290

DOI: 10.1021/acs.orglett.7b02290

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