Anti-inflammatory Dimeric 2-(2-Phenylethyl)chromones from the Resinous Wood of Aquilaria sinensis

作者：Huo, Hui-Xia; Zhu, Zhi-Xiang; Song, Yue-Lin; Shi, She-Po; Sun, Jing; Sun, Hui; Zhao, Yun-Fang; Zheng, Jiao; Ferreira, Daneel; Zjawiony, Jordan K.; Tu, Peng-Fei; Li, Jun^*

来源：Journal of Natural Products, 2018, 81(3): 543-553.

DOI：10.1021/acs.jnatprod.7b00919

• SIGNALING PATHWAYS
• CHINESE AGARWOOD
• AGALWOOD JINKO
• BI-PHENYLETHYLCHROMONES
• INHIBITING STAT1/3
• SUPPRESSES INNATE
• ADAPTIVE IMMUNITY
• DERIVATIVES
• 2-(2-PHENETHYL)-CHROMONE

Sixteen new 2-(2-phenylethyl)chromone dimers, including four pairs of enantiomers (la/lb, 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 mu M.

• 出版日期2018-3
• 单位北京中医药大学