Zizaane-Type Sesquiterpenoids and Their Rearranged Derivatives from Agarwood of an Aquilaria Plant

Jing-Zhe Yuan,Hao Wang,Hui-Qin Chen,Wen-Hua Dong,Li Yang,Attila Mándi,Tibor Kurtán,Wei Li,Hao-Fu Dai,Cai-Hong Cai,Wen-Li Mei,Yi-Ling Yang

doi:10.3390/molecules27010198

Abstract

Nine new sesquiterpenoids (1–9) were isolated from ethyl ether extract of agarwood originated from Aquilaria sp., including three novel sesquiterpenoids (1–3) derived from zizaane, together with six zizaane-type sesquiterpenoids (4–9). All structures were unambiguously elucidated based on 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of sesquiterpenoids was determined by comparison of the experimental and computed ECD spectra. In vitro anti-inflammatory assessment showed that compound 9 exhibited inhibition of NO production in LPS-stimulated RAW264.7 cells with an IC50 value of 62.22 ± 1.27 μM.

Highlights

Agarwood is produced inside Aquilaria and Gyrinops trees as a self-treatment mechanism to suppress various forms of injury, such as chopping, holing, nailing, microbial infection, etc. [1]
The sesquiterpenes from agarwood exhibit various types, including agarofurans, agarospiranes, guaianes, eudesmanes, eremophilanes, cadinanes, prezizaanes, zizaanes, acoranes, etc., which contribute to the smell and pharmacological properties of agarwood [1]
11-methyl ester groups were identified from agarwood originated from Aquilaria sp. [3,4,5]

Summary

Introduction

Agarwood is produced inside Aquilaria and Gyrinops trees as a self-treatment mechanism to suppress various forms of injury, such as chopping, holing, nailing, microbial infection, etc. [1]. Agarwood is produced inside Aquilaria and Gyrinops trees as a self-treatment mechanism to suppress various forms of injury, such as chopping, holing, nailing, microbial infection, etc. Chemical studies revealed that sesquiterpenes and 2-(2-phenethyl)chromones are two main types of components [2]. The sesquiterpenes from agarwood exhibit various types, including agarofurans, agarospiranes, guaianes, eudesmanes, eremophilanes, cadinanes, prezizaanes, zizaanes, acoranes, etc., which contribute to the smell and pharmacological properties of agarwood [1]. Plenty of tricyclic prezizaanes, three zizaanes and several sesquiterpenes bearing. 11-methyl ester groups were identified from agarwood originated from Aquilaria sp. Some of them exhibit potent α-glucosidase and acetylcholinesterase inhibition activities. In continuation of identifying bioactive constituents from the agarwood originating from 11-methyl ester groups were identified from agarwood originated from Aquilaria sp. [3,4,5].

Methods

Results

Conclusion