Novel flavonol-3-O-methylethers from Zanthoxylum pistaciifolium Griseb. (Rutaceae)

• Published in: Natural product research 2022-10, Vol.36 (19), p.4869-4878
• Main Authors: Heredia Díaz, Yamilé, Tuenter, Emmy, Garcia-Díaz, Jesús, Ochoa Pacheco, Ania, Cos, Paul, Pieters, Luc, Escalona Arranz, Julio César
• Format: Article
• Language: English
• Subjects: antifungal; Antiinfectives and antibacterials; Antiprotozoal activity; antitrypanosomal; Cytotoxicity; Endemic plants; Flavonoids; Flavonols; Glucosides; Herbal medicine; Hexanes; Kaempferol; n-Hexane; Toxicity; Zanthoxylum pistaciifolium
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2021.1906240

Zanthoxylum pistaciifolium Griseb. is a tree endemic to Cuba, occasionally used in herbal medicine. Previously, the antitrypanosomal activity of a n-hexane-2-butanone extract of Z. pistaciifolium leaves and of its constituent skimmianine were published. In the current study a more thorough examination of the respective extract is performed, which led to the isolation and identification of three flavonoids, more specifically, the flavonol-3-O-methylethers kaempferol-3-O-methylether (1) and novel compounds kaempferol-3-O-methylether-5-O-β-D-glucoside (2) and kaempferol-8-hydroxy-3,7-O-dimethylether-5-O-β-D-glucoside (3). All compounds were screened for their antimicrobial and antiprotozoal activity and cytotoxicity towards MRC-5 SV2 cells. Compound 1 showed a moderate to weak activity against Trypanosoma cruzi (IC 50 30.8 μM), T. brucei (IC 50 15.4 μM) and Plasmodium falciparum (IC 50 53.8 μM), but also showed cytotoxicity (CC 50 19.0 μM). Compounds 2 and 3 did not display activity in any of the assays (IC 50 and CC 50 > 64 μM).