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

• Published in: Natural product research Vol. ahead-of-print; no. ahead-of-print; pp. 1 - 12
• Main Authors: Feng, Yun-Qian, Zhang, Pan, Jian, Jin-Zhen, Wang, Zhi-Wei, Tian, Xiao-Long, Luo, Guo-Yong, Yang, Wu-De
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 16.09.2024; Taylor & Francis Ltd
• Subjects: 2-arylbenzo[b]furans; antioxidant capacity; Antioxidants - chemistry; Benzofurans - chemistry; Carbon dioxide; Carboxylic acids; Fragmentation; fragmentation patterns; Furans; Itea; Itea omeiensis; Magnetic Resonance Spectroscopy - methods; Mass spectrometry; Mass Spectrometry - methods; Mass spectroscopy; Molecular Structure; Negative ions; NMR; Nuclear magnetic resonance; Oxidation; Pesticides; Plant Components, Aerial - chemistry; Plant Extracts - chemistry; Scavenging; Superoxide anions; Two dimensional analysis; Itea omeiensis; Itea; antioxidant capacity; 2-arylbenzo[b]furans; fragmentation patterns
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2023.2216344

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 IC 50 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 CH 2 O fragment [M-H-30] - for 3-hydroxymethyl-2-arylbenzo[b]furans, and the loss of CO 2 fragment [M-H-44] - for 2-arylbenzo[b]furan-3-carboxylic acids.