Study on 2-arylbenzo[b]furans from Itea omeiensis and their fragmentation patterns with Q-Orbitrap mass spectrometry

IF 1.9 3区化学 Q3 CHEMISTRY, APPLIED

Natural Product Research Pub Date : 2024-09-16 DOI:10.1080/14786419.2023.2216344

引用次数: 0

Abstract

One new 2-arylbenzo[b]furan named iteafuranal F (1) as well as two known analogues (2–3) were isolated from the 95% EtOH extract of aerial parts of Itea omeiensis. Their chemical structures were constructed based on extensive analyses of UV, IR, 1D/2D NMR and HRMS spectra. Antioxidant assays revealed significant superoxide anion radical scavenging capacity of 1 with IC₅₀ value of 0.66 mg/mL, which was comparable to the efficiency of positive control of luteolin. In addition, the preliminary MS fragmentation patterns in negative ion mode were established to distinguish 2-arylbenzo[b]furans with C-10 in different oxidation states: the characteristic loss of CO molecule [M-H-28]^- was observed for 3-formyl-2-arylbenzo[b]furans, and the loss of CH₂O fragment [M-H-30]^- for 3-hydroxymethyl-2-arylbenzo[b]furans, and the loss of CO₂ fragment [M-H-44]^- for 2-arylbenzo[b]furan-3-carboxylic acids.

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用 Q-Orbitrap 质谱法研究峨嵋杉中的 2-芳基苯并[b]呋喃及其碎片模式。

从梅花鹿气生部分 95% 的 EtOH 提取物中分离出一种新的 2-芳基苯并[b]呋喃，命名为 iteafuranal F（1），以及两种已知的类似物（2-3）。通过对紫外光谱、红外光谱、1D/2D NMR 光谱和 HRMS 光谱的大量分析，构建了它们的化学结构。抗氧化试验显示，1 具有显著的超氧阴离子自由基清除能力，其 IC50 值为 0.66 mg/mL，与阳性对照物木犀草素的清除能力相当。此外，初步建立了负离子模式下的质谱碎片模式，以区分处于不同氧化态的 C-10 的 2-芳基苯并[b]呋喃：在 3-甲酰基-2-芳基苯并[b]呋喃中观察到特征性的 CO 分子丢失[M-H-28]-，在 3-羟甲基-2-芳基苯并[b]呋喃中观察到 CH2O 片段丢失[M-H-30]-，在 2-芳基苯并[b]呋喃-3-羧酸中观察到 CO2 片段丢失[M-H-44]-。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Natural Product Research 化学-医药化学

CiteScore

5.10

自引率

9.10%

发文量

605

审稿时长

2.1 months

期刊介绍： The aim of Natural Product Research is to publish important contributions in the field of natural product chemistry. The journal covers all aspects of research in the chemistry and biochemistry of naturally occurring compounds. The communications include coverage of work on natural substances of land and sea and of plants, microbes and animals. Discussions of structure elucidation, synthesis and experimental biosynthesis of natural products as well as developments of methods in these areas are welcomed in the journal. Finally, research papers in fields on the chemistry-biology boundary, eg. fermentation chemistry, plant tissue culture investigations etc., are accepted into the journal. Natural Product Research issues will be subtitled either ""Part A - Synthesis and Structure"" or ""Part B - Bioactive Natural Products"". for details on this , see the forthcoming articles section. All manuscript submissions are subject to initial appraisal by the Editor, and, if found suitable for further consideration, to peer review by independent, anonymous expert referees. All peer review is single blind and submission is online via ScholarOne Manuscripts.