np7b00919_si_002.cif (33.67 kB)
Anti-inflammatory Dimeric 2‑(2-Phenylethyl)chromones from the Resinous Wood of Aquilaria sinensis
dataset
posted on 2017-12-11, 20:39 authored by Hui-Xia Huo, Zhi-Xiang Zhu, Yue-Lin Song, She-Po Shi, Jing Sun, Hui Sun, Yun-Fang Zhao, Jiao Zheng, Daneel Ferreira, Jordan K. Zjawiony, Peng-Fei Tu, Jun LiSixteen new 2-(2-phenylethyl)chromone
dimers, including four pairs
of enantiomers (1a/1b, 3a/3b, 6a/6b, and 8a/8b), along with eight optically pure analogues (2, 4, 5, 7, and 9–12) were isolated from the resinous wood of Aquilaria sinensis. Their structures were determined by
extensive spectroscopic analysis (1D and 2D NMR, UV, IR, and HRMS)
and experimental and computed ECD data. Compounds 1–10 feature an unusual 3,4-dihydro-2H-pyran
ring linkage connecting two 2-(2-phenylethyl)chromone monomeric units,
while compounds 11 and 12 possess an unprecedented
6,7-dihydro-5H-1,4-dioxepine moiety in their structures.
A putative biosynthetic pathway of the representative structures via
a diepoxy derivative of a chromone with a nonoxygenated A-ring is
also proposed. Compounds 1a/1b, 2, 3a/3b, 5, 7, 8a/8b, and 10–12 exhibited significant
inhibition of nitric oxide production in lipopolysaccharide-stimulated
RAW264.7 cells with IC50 values in the range 7.0–12.0
μM.