New Octadecanoid Enantiomers from the Whole Plants of Plantago depressa.
In this study, 19 octadecanoid derivatives-four pairs of enantiomers (1⁻8), two racemic/scalemic mixtures (9⁻10), and nine biosynthetically related analogues-were obtained from the ethanolic extract of a Chinese medicinal plant, Plantago depressa Willd. Their structures were elucidated on the basis of detailed spectroscopic analyses, with the absolute configurations of the new compounds assigned by time-dependent density functional theory (TD-DFT)-based electronic circular dichroism (ECD) calculations. Six of them (1, 3⁻6, and 9) were reported for the first time, while 2, 7, and 8 have been previously described as derivatives and are currently obtained as natural products. Our bioassays have established that selective compounds show in vitro anti-inflammatory activity by inhibiting lipopolysaccharide-induced nitric oxide (NO) production in mouse macrophage RAW 264.7 cells.
['Song|Xiu-Qing|XQ|', 'Zhu|Kongkai|K|', 'Yu|Jin-Hai|JH|', 'Zhang|Qianqian|Q|', 'Zhang|Yuying|Y|', 'He|Fei|F|', 'Cheng|Zhi-Qiang|ZQ|', 'Jiang|Cheng-Shi|CS|0000-0002-2760-7596', 'Bao|Jie|J|', 'Zhang|Hua|H|']
D000818:Animals D000893:Anti-Inflammatory Agents D008070:Lipopolysaccharides D008264:Macrophages D051379:Mice D009569:Nitric Oxide D010943:Plantago D000067996:RAW 264.7 Cells D013228:Stearates
octadecanoid Plantago depressa anti-inflammation fatty acid natural enantiomer