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

Yun-Qian Feng; Pan Zhang; Jin-Zhen Jian; Zhi-Wei Wang; Xiao-Long Tian; Guo-Yong Luo; Wu-De Yang

doi:10.1080/14786419.2023.2216344

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

Nat Prod Res. 2023 May 28:1-12. doi: 10.1080/14786419.2023.2216344. Online ahead of print.

Authors

Yun-Qian Feng¹, Pan Zhang¹, Jin-Zhen Jian¹, Zhi-Wei Wang¹, Xiao-Long Tian¹, Guo-Yong Luo¹, Wu-De Yang¹

Affiliation

¹ School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang, People's Republic of China.

PMID: 37245178
DOI: 10.1080/14786419.2023.2216344

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.

Keywords: 2-arylbenzo[b]furans; Itea; Itea omeiensis; antioxidant capacity; fragmentation patterns.