HPLC-ESI-MSn Identification and NMR Characterization of Glucosyloxybenzyl 2R-Benzylmalate Deriva-Tives from Arundina Graminifolia and Their Anti-Liver Fibrotic Effects In Vitro.

Qingqing Liu,Feiyi Sun,Rongji Dai,Yulin Deng,Fang Lv

doi:10.3390/molecules24030525

Qingqing Liu, Feiyi Sun + Show 3 more

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https://doi.org/10.3390/molecules24030525

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Abstract

Four new glucosyloxybenzyl 2R-benzylmalate derivatives, named Arundinoside H (2), I (5), J (6), K (8) as well as four known compounds Arundinoside D (1), G (3), F (4), E (7) were isolated and characterized by a combination of chemical and spectroscopic methods, including HR-ESI-MS, 1D and 2D NMR experiments. Besides, 24 unreported compounds were inferred from ESI-MSn data. The anti-liver fibrotic activities of the isolates were determined as proliferation inhibition of lipopolysaccharide (LPS)-induced activation of rat hepatic stellate cells (HSC-T6). The result suggested Arundinosides D, H, F, I and K showed moderate inhibitory effects in vitro.

Highlights

They were noticed for their novel type of structure and significant activities, while the research of glucosyloxybenzyl 2R-benzylmalates was limited by their higher polarity and less content
nuclear magnetic resonance (NMR) analysis, it was possible to identify 8 compounds isolated from A. graminifolia, and to predict the structures of 24 previously unreported glucosyloxybenzyl 2R-benzylmalates in the extract
The ESI-MSn experiments provide a useful guide for gaining the large structural information of novel compounds, which are important to drug design, the analytical method cannot confirm the accurate substitution position of Ac groups of these glucosyloxybenzyl 2R-benzylmalates

Summary

Introduction

Don) Hochr., a species widely distributed in subtropical Asia and known as bai-yang-jie in Chinese, has a long history of use as one of the major drugs in a formula “BaoGan. Capusle” with the efficacy of heat clearing and detoxifying, dispersing blood and relieving pain, reducing inflammation and promoting urination and so on [1]. In the course of our studies on pharmacology, it was proved that the formula “BaoGan Capusle”. As a continuing study on bioactive constituents of A. graminifolia, a series of phytochemical and biological experiments of the n-butanol (n-BuOH) extract was performed to yield the isolation of four new and four known glucosyloxybenzyl 2R-benzylmalates. We described the isolation and structural elucidation of these derivatives, as well as their anti-liver fibrotic activities in vitro

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