Polycyclic Polyprenylated Acylphloroglucinol Derivatives from Hypericum acmosepalum.

Jiao Wang,Jin Li,Tengfei Ji,Mengjiao Shi,Jiajia Wang

doi:10.3390/molecules24010050

Abstract

Hypericum acmosepalum belongs to the Hypericum genus of the Guttiferae family. The characteristic components in Hypericum are mainly a series of polycyclic polyprenylated acylphloroglucinols (PPAPs), flavonoids, and xanthones. Among them, the PPAPs have received much attention due to their novel structures and diverse pharmacological activities and have become hot spots in organic chemistry and medicinal chemistry. However, there are few reports about the chemical constituents of Hypericum acmosepalum at present, especially the PPAPs. This research is dedicated to the study of the air-dried aerial parts of Hypericum acmosepalum, which were extracted with 95% EtOH under reflux, then suspended and successively partitioned with petroleum ether and ethyl acetate. Five PPAP derivatives were obtained using various chromatographic techniques, and their structures were determined by NMR spectroscopic data, including two new phloroglucinol derivatives, hyperacmosin A (1) and hyperacmosin B (2). Those compounds were evaluated for their neuroprotective effect using two models.

Highlights

Plants of the genus Hypericum of the family Guttiferae, which includes 484 species, mostly herbs or shrubs, are widely distributed in various regions of the world
As a part of an ongoing research program aimed at the isolation, structural characterization, and pharmacological evaluation of bioactive polyprenylated acylphloroglucinols (PPAPs) from the Hypericum genus [6,19,20], a preliminary study was carried out on the petroleum ether-soluble part of the 95% EtOH extract from the air-dried aerial parts of H. acmosepalum, and obtained five PPAP
The petroleum ether soluble part was subjected to silica gel column chromatography to give two new compounds (1–2) and three known compounds: silica gel column chromatography to give two new compounds and three known compounds: Oxepahyperforin (3) [21], sampsonione O (4) [22], sampsonione L (5) [23,24]

Summary

Introduction

Plants of the genus Hypericum of the family Guttiferae, which includes 484 species, mostly herbs or shrubs, are widely distributed in various regions of the world. Hypericum plants have diverse pharmacological applications as folk medicines due to the diverse chemical constituents [4,5,6]. Commonly known as Xiangzhen tree in Yunnan Province, belongs to the Hypericum genus [16]. It mostly grows in Yunnan, Guizhou, and Sichuan Province, and is used in folk medicine to treat inflammation and hepatitis [17]. As a part of an ongoing research program aimed at the isolation, structural characterization, and pharmacological evaluation of bioactive PPAPs from the Hypericum genus [6,19,20], a preliminary study was carried out on the petroleum ether-soluble part of the 95% EtOH extract from the air-dried aerial parts of H. acmosepalum, and obtained five PPAP

Methods

Results

Conclusion