Hybeanones A and B, Two Highly Modified Polycyclic Polyprenylated Acylphloroglucinols from Hypericum beanii. Issue 1 (16th November 2021)

• Record Type: Journal Article
• Authors: Yang, Beiye; Qi, Changxing; Yao, Zeyu; Lin, Shuang; Li, Fengli; Sun, Weiguang; Hu, Zhengxi; Zhang, Yonghui
• Is Part Of: Chinese journal of chemistry. Volume 40:Issue 1(2022)
• Page Start: 53
• Page End: 58
• Publication Date: 2021-11-16
• Subjects: Hypericum beanii -- Natural products -- Structure elucidation -- Inhibitors -- Molecular docking; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.202100468
• Languages: English
• ISSNs: 1001-604X

Abstract

Comprehensive Summary: Hybeanones A and B (1 and 2 ), two highly oxygenated and rearranged polycyclic polyprenylated acylphloroglucinols (PPAPs), were isolated from the aerial parts of Hypericum beanii . Their structures comprising absolute configurations were elucidated by spectroscopic analysis, single‐crystal X‐ray diffraction, and quantum chemical calculations. Compounds 1 and 2 are defined by a newly assembled cyclopentanone unit fused to a tricyclic γ ‐lactone unit via a ketone carbonyl. The breakage of C‐1/C‐2 linkage via retro‐Claisen reaction, attack from C‐1 to C‐19, and Baeyer‐Villiger oxidation at C‐1/C‐23 bond were presumed to be the key steps in the assembly of 1 and 2 . The isolates 1 and 2 showed potential acetylcholinesterase (AchE) inhibitory activities, with IC50 values of 21.34 ± 1.48 and 18.79 ± 2.36 μmol/L, respectively. Abstract :