Abstract
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.
Highlights
The genus Plantago L. consists of more than 190 species that are widely distributed in temperate and tropical areas all over the world
The structures of these compounds were fully characterized by comprehensive spectroscopic analyses, with the absolute stereochemistry of the new compounds established via calculated electronic circular dichroism (ECD) data
The (+)-enantiomer (1) was identified to be identified to be a new compound, while the (−)‐enantiomer (2) was a new natural product that had a new compound, while the (−)-enantiomer (2) was a new natural product that had been reported been reported as the methyl ester of porrigenic acid (10) during structure characterization [12]
Summary
The genus Plantago L. (family Plantaginaceae) consists of more than 190 species that are widely distributed in temperate and tropical areas all over the world. We carried out an intensive chemical study on the EtOAc partition generated from the ethanolic extract of the whole plants of P. depressa, which resulted in the isolation of a series of fatty acid derivatives—four pairs of enantiomers (1–8), two racemic/scalemic mixtures (9–10) (Figure 1), and nine related analogues (11–19). The structures of these compounds were fully characterized by comprehensive spectroscopic analyses, with the absolute stereochemistry of the new compounds established via calculated ECD data.
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