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Molecules 2018, 23(5), 1187; https://doi.org/10.3390/molecules23051187

The Antimicrobial Activity of Annona emarginata (Schltdl.) H. Rainer and Most Active Isolated Compounds against Clinically Important Bacteria

1
Faculty of Chemistry Biochemistry and Pharmacy, National University of San Luis, Chacabuco 917, 5700 San Luis, Argentina
2
Institute of Biotechnology-Institute of Basic Sciences, National University of San Juan, Av. Libertador General San Martin 1109, 5400 San Juan, Argentina
3
Institute of Chemistry, University of Silesia, 75 Pulku Piechoty 1, 41500 Chorzow, Poland
4
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, 83232 Bratislava, Slovakia
5
Multidisciplinary Institute of Biological Research IMIBIO-CONICET, Chacabuco 917, 5700 San Luis, Argentina
*
Authors to whom correspondence should be addressed.
Received: 24 April 2018 / Revised: 9 May 2018 / Accepted: 10 May 2018 / Published: 16 May 2018
(This article belongs to the Section Natural Products Chemistry)
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Abstract

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. View Full-Text
Keywords: Annona emarginata; (R)-2-(4-methylcyclohex-3-en-1-yl)propan-2-yl (E)-3-(4-hydroxyphenyl)-acrylate; antibacterial activity; Staphylococcus aureus; structure-activity relationships Annona emarginata; (R)-2-(4-methylcyclohex-3-en-1-yl)propan-2-yl (E)-3-(4-hydroxyphenyl)-acrylate; antibacterial activity; Staphylococcus aureus; structure-activity relationships
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Dolab, J.G.; Lima, B.; Spaczynska, E.; Kos, J.; Cano, N.H.; Feresin, G.; Tapia, A.; Garibotto, F.; Petenatti, E.; Olivella, M.; Musiol, R.; Jampilek, J.; Enriz, R.D. The Antimicrobial Activity of Annona emarginata (Schltdl.) H. Rainer and Most Active Isolated Compounds against Clinically Important Bacteria. Molecules 2018, 23, 1187.

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