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The Antimicrobial Activity of Annona emarginata (Schltdl.) H. Rainer and Most Active Isolated Compounds against Clinically Important Bacteria.
- Source :
-
Molecules (Basel, Switzerland) [Molecules] 2018 May 16; Vol. 23 (5). Date of Electronic Publication: 2018 May 16. - Publication Year :
- 2018
-
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.
- Subjects :
- Argentina
Flowers chemistry
Gram-Negative Bacteria drug effects
Gram-Positive Bacteria drug effects
Klebsiella pneumoniae drug effects
Medicine, Traditional
Methicillin-Resistant Staphylococcus aureus drug effects
Microbial Sensitivity Tests
Plant Bark chemistry
Plant Leaves chemistry
Annona chemistry
Anti-Infective Agents chemistry
Anti-Infective Agents pharmacology
Plant Extracts chemistry
Plant Extracts pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1420-3049
- Volume :
- 23
- Issue :
- 5
- Database :
- MEDLINE
- Journal :
- Molecules (Basel, Switzerland)
- Publication Type :
- Academic Journal
- Accession number :
- 29772647
- Full Text :
- https://doi.org/10.3390/molecules23051187