1. Chalcone dimers from Astronium graveolens (Anacardiaceae) and their biological activities.
- Author
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da Silva, Eliezer P., David, Jorge M., David, Juceni P., Alves, Clayton Q., and Moreira, Bruno O.
- Abstract
This work describes the chemical composition of the stems of Astronium graveolens Jacq. (Anacardiaceae). The CH 2 Cl 2 and EtOAc soluble fractions of this extract were subjected to chromatographic procedures that allowed obtaining the unreported dimers (7" R *, 8" S *) 2′, 4,4′, 5-tetrahydroxychalcone-(2 → 7", 8 → 8")-2′", 4", 4′"- trihydroxy-7", 8"-dihydrochalcone and (7 S *,8 R *,7" S *,8" S *)-2′,4,4′,5,7-pentahydroxy-7,8-dihydrochalcone-(2→7",8→8")-2′",4",4"'-7 ", 8 "- dihydrochalcone, the previously isolated chalcone dimer named matosine (7 S *,8 S *,7'' S *,8" R *)-2′,4,4′, 5,7-pentahydroxy-7,8-dihydrochalcone-(2→7", 8→8")-2′", 4", 4′"-trihydroxy-7", 8"- dihydrochalcone). Besides these specific chalcone dimers, sitosterol, sitosterol-3- O -β-D-glucoside, methyl gallate, gallic acid, and quercitrin were also isolated. These compounds were identified by mono and bidimensional NMR data analysis and HRMS. Methanolysis of triacylglycerides yielded a mixture of fatty acid methyl esters, which were identified by GC-MS. The profile indicated this fraction is composed of saturated (54.13 %) and unsaturated (46.21 %) fatty acids, and palmitic acid and oleic acid are the major components. The brine shrimp test of the extract showed that the soluble fraction CH 2 Cl 2 of the stems exhibited high toxicity; meanwhile, the EtOAc soluble fraction presented moderate toxicity. The Elmann test indicated that the EtOAc was considered an expressive AChE inhibitor, and the chalcone dimers 1 , 2, and 3 present excellent anticholinesterase activities inhibiting 83.88 %, 70.72 %, and 62.60 % AChE at concentrations of 500 µM, respectively. [Display omitted] • New chalcone dimers were isolated from Astronium graveolens stem. • Astronium graveolens extracts and isolated chalcone dimers inhibit anticholinesterase enzyme. • Chalcone dimers were isolated for the first time in Astronium genus. [ABSTRACT FROM AUTHOR]
- Published
- 2024
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