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Open AccessArticle

New Octadecanoid Enantiomers from the Whole Plants of Plantago depressa

1
School of Chemistry and Chemical Engineering, University of Jinan, 336 West Road of Nan Xinzhuang, Jinan 250022, China
2
School of Biological Science and Technology, University of Jinan, 336 West Road of Nan Xinzhuang, Jinan 250022, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Pavel B. Drasar
Molecules 2018, 23(7), 1723; https://doi.org/10.3390/molecules23071723
Received: 25 June 2018 / Revised: 10 July 2018 / Accepted: 11 July 2018 / Published: 14 July 2018
(This article belongs to the Special Issue Synthesis, Study and Utilization of Natural Products)
In this study, 19 octadecanoid derivatives—four pairs of enantiomers (18), two racemic/scalemic mixtures (910), 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, 36, 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. View Full-Text
Keywords: Plantago depressa; octadecanoid; fatty acid; natural enantiomer; anti-inflammation Plantago depressa; octadecanoid; fatty acid; natural enantiomer; anti-inflammation
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MDPI and ACS Style

Song, X.-Q.; Zhu, K.; Yu, J.-H.; Zhang, Q.; Zhang, Y.; He, F.; Cheng, Z.-Q.; Jiang, C.-S.; Bao, J.; Zhang, H. New Octadecanoid Enantiomers from the Whole Plants of Plantago depressa. Molecules 2018, 23, 1723.

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