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The asymmetric unit of the title compound, C10H11NO4, which was synthesized via nitration reaction of eugenol (4-allyl-2-methoxyphenol) with a mixture of nitric acid and sulfuric acid, consists of three independent molecules of similar geometry. Each molecule displays an intramolecular hydrogen bond involving the hydroxide and the nitro group forming an S(6) motif. The crystal cohesion is ensured by intermolecular C—H...O hydrogen bonds in addition to π–π stacking interactions between the aromatic rings [centroid–centroid distances = 3.6583 (17)–4.0624 (16) Å]. The Hirshfeld surface analysis and the two-dimensional fingerprint plots show that H...H (39.6%), O...H/H...O (37.7%), C...H/H...C (12.5%) and C...C (4%) are the most important contributors towards the crystal packing.

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Background and objective. Chemical spermicides currently marketed and widely used are known to have many side effects. Thereby, and in order to look for more tolerated natural spermicidal agents, the aim of this work was to evaluate the spermicidal potential of saponin extracts from the roots of Saponaria officinalis / Caryophyllaceae, Glycyrrhizia glabra / Fabaceae, and Herniaria glabra / Caryophyllaceae by studying their in vitro effects on sperm mobility and vitality. Methods. Methanolic saponin extracts from the plants roots were performed. Sperm suspensions were prepared by centrifugation on a PureSperm® density gradient (70 and 45%) and incubated with various concentrations of saponin extracts (50, 250, 500 and 750 mg/mL) at 37°C. The spermicidal activity was evaluated by studying the mobility and vitality of spermatozoa at different time intervals ranging from 10 to 240 minutes. Results. A dose and time dependent effect on sperm mobility and vitality was observed for our extracts. Extracts from Saponaria officinalis roots induced an irreversible immobilization and a total non-viability of sperm within 10 minutes at a concentration of 750 mg/mL. A similar effect was observed within 30 minutes at 750 mg/mL for Herniaria glabra extract and within 90 minutes at 500 mg/ml for Glycyrrhizia glabra extract. Conclusion. The results of our study showed that the saponin extracts of our plants roots possess potent in vitro dose and time dependant spermicidal effect. These natural products could therefore represent a safer and better tolerated alternative to chemical spermicides.

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