| Autor: |
Dolab JG; Faculty of Chemistry Biochemistry and Pharmacy, National University of San Luis, Chacabuco 917, 5700 San Luis, Argentina. juandolab@gmail.com., Lima B; Institute of Biotechnology-Institute of Basic Sciences, National University of San Juan, Av. Libertador General San Martin 1109, 5400 San Juan, Argentina. blima@unsj.edu.ar., Spaczynska E; Institute of Chemistry, University of Silesia, 75 Pulku Piechoty 1, 41500 Chorzow, Poland. ewelina.spaczynska@gmail.com., Kos J; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, 83232 Bratislava, Slovakia. jirikos85@gmail.com., Cano NH; Institute of Biotechnology-Institute of Basic Sciences, National University of San Juan, Av. Libertador General San Martin 1109, 5400 San Juan, Argentina. natividadhc17@hotmail.com., Feresin G; Institute of Biotechnology-Institute of Basic Sciences, National University of San Juan, Av. Libertador General San Martin 1109, 5400 San Juan, Argentina. gferesin@unsj.edu.ar., Tapia A; Institute of Biotechnology-Institute of Basic Sciences, National University of San Juan, Av. Libertador General San Martin 1109, 5400 San Juan, Argentina. atapia@unsj.edu.ar., Garibotto F; Faculty of Chemistry Biochemistry and Pharmacy, National University of San Luis, Chacabuco 917, 5700 San Luis, Argentina. fgaribotto@gmail.com.; Multidisciplinary Institute of Biological Research IMIBIO-CONICET, Chacabuco 917, 5700 San Luis, Argentina. fgaribotto@gmail.com., Petenatti E; Faculty of Chemistry Biochemistry and Pharmacy, National University of San Luis, Chacabuco 917, 5700 San Luis, Argentina. elipete@unsl.edu.ar., Olivella M; Faculty of Chemistry Biochemistry and Pharmacy, National University of San Luis, Chacabuco 917, 5700 San Luis, Argentina. olivellamonica@gmail.com., Musiol R; Institute of Chemistry, University of Silesia, 75 Pulku Piechoty 1, 41500 Chorzow, Poland. robert.musiol@us.edu.pl., Jampilek J; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, 83232 Bratislava, Slovakia. josef.jampilek@gmail.com., Enriz RD; Faculty of Chemistry Biochemistry and Pharmacy, National University of San Luis, Chacabuco 917, 5700 San Luis, Argentina. denriz@unsl.edu.ar.; Multidisciplinary Institute of Biological Research IMIBIO-CONICET, Chacabuco 917, 5700 San Luis, Argentina. denriz@unsl.edu.ar. |
| Abstrakt: |
Annona emarginata (Schltdl.) H. Rainer, commonly known as "arachichú", "araticú", "aratigú", and "yerba mora", is a plant that grows in Argentina. Infusions and decoctions are used in folk medicine as a gargle against throat pain and for calming toothache; another way to use the plant for these purposes is chewing its leaves. Extracts from bark, flowers, leaves, and fruits from A. emarginata were subjected to antibacterial assays against a panel of Gram (+) and Gram (-) pathogenic bacteria according to Clinical and Laboratory Standards Institute protocols. Extracts from the stem bark and leaves showed moderate activity against the bacteria tested with values between 250⁻1000 µg/mL. Regarding flower extracts, less polar extracts (hexane, dichloromethane) showed very strong antibacterial activity against methicillin-sensitive Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus ATCC 43300 with values between 16⁻125 µg/mL. Additionally, hexane extract showed activity against Klebsiella pneumoniae (MIC = 250 µg/mL). The global methanolic extract of the fruits (MeOHGEF) was also active against the three strains mentioned above, with MICs values 250⁻500 µg/mL. Bioassay-guided fractionation of MeOHGEF led to the isolation of a new main compound-( R )-2-(4-methylcyclohex-3-en-1-yl)propan-2-yl ( E )-3-(4-hydroxyphenyl)acrylate ( 1 ). The structure and relative configurations have been determined by means of 1D and 2D NMR techniques, including COSY, HMQC, HMBC, and NOESY correlations. Compound 1 showed strong antimicrobial activity against all Gram (+) species tested (MICs = 3.12⁻6.25 µg/mL). In addition, the synthesis and antibacterial activity of some compounds structurally related to compound 1 (including four new compounds) are reported. A SAR study for these compounds was performed based on the results obtained by using molecular calculations. |
