Issue 1, 2021

Two new seco-polycyclic polyprenylated acylphloroglucinol from Hypericum sampsonii

Abstract

Hypsampsone A (1) and hyperhexanone F (2), two novel seco-polycyclic polyprenylated acylphloroglucinols, were isolated from Hypericum sampsonii. Hypsampsone A (1) features the first spirocyclic system fused with 5/6/5/5 tetracyclic skeleton. Hyperhexanone F (2) represents the second novel 1,2-seco-bicyclo[3.3.1]-PPAP skeleton. Their structures were established by extensive spectroscopic analysis, computer-assisted structure elucidation software, and calculated electronic circular dichroism spectra. A plausible biogenetic pathway of 1 was also proposed. Compounds 1 and 2 showed moderate multidrug resistance reversal activity to adriamycin (ADR) resistant cancer cell lines, HepG2/ADR and MCF-7/ADR, with the fold-reversals ranging from 16 to 38 at noncytotoxic concentration of 10 μM.

Graphical abstract: Two new seco-polycyclic polyprenylated acylphloroglucinol from Hypericum sampsonii

Supplementary files

Article information

Article type
Paper
Submitted
11 Oct 2020
Accepted
10 Nov 2020
First published
12 Nov 2020

Org. Biomol. Chem., 2021,19, 216-219

Two new seco-polycyclic polyprenylated acylphloroglucinol from Hypericum sampsonii

Z. Zhang, Y. Zeng, Y. Li, Z. Hu, L. Huang, W. Gu, X. Hao and C. Yuan, Org. Biomol. Chem., 2021, 19, 216 DOI: 10.1039/D0OB02072A

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