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Abstract
The ricinoleate triglyceride was extracted from castor-oil seeds grown in Algeria and isolated by catalytically methanolyse to methyl ricinoleate. Six diazole and triazole derivatives of ricinoleic acid were synthesized and characterized: 1,3,4-oxadiazole-5-thione (4); 1,3,4-thiadiazole-5-thione (5); 4-N-amino-1,2,4-triazole-5-thiol (7); 1,2,4-triazole-5-thione (9); 5-amino-1,3,4-oxadiazole (10) and 5-amino-1,3,4-thiadiazole (11). The antibacterial and antifungal screening data of synthesized compounds showed appreciable inhibition and among them, 5, 7 and 8 showed more inhibition on Gram positive Enterococcus faecalis than reference ampiciline; while compounds 1, 7, 8, 10 and 11 showed competitive antifungal effects compared to reference amphotericin B. In addition, all synthesized compounds (1-11) showed competitive antioxidant properties, particularly compounds 7 at 125, 250, 500 and 1000 μg/mL and compounds 4, 5 and 9 at a concentration of 1000 μg/mL. The intermediate compounds 1, 2 and 8 showed anti-α-amylase activity at various concentrations in the range of IC50 = (120.25 ± 1.17 - 130.42 ± 2.48). Oxadiazole 4 showed the best α-amylase inhibition by 78.5% at a concentration of 1000 μg/mL.
Highlights
GeneralAll reactions were monitored by TLC, silica gel F254, made by Merck, Germany
All the synthesized compounds were tested for their in vitro antimicrobial activity against the Gram positive bacteria Staphylococcus aureus (ATCC25923), Enterococcus faecalis (ATCC-29212), Bacillus cereus (ATCC 21332), the Gram-negative bacteria Pseudomonas aeruginosa (ATCC-27853), Escherichia coli (ATCC-25922), Klebsiella planticola (ATCC33531), Salmonella, Proteus vulgarus (ATCC 29905), in the nutrient agar media and fungi Candida albicans (ATCC 10231), Aspergillus niger (ATCC 16404), Trichosporon Sp, Fusarium, Penicillium Sp and Altenaria in Sabouraud dextrose medium using the serial plate dilution method
From a methodological point of view, the free radical test, 2,2-diphenyl-1- picrylhydrazyl radical (DPPH) is recommended for compounds containing the SH, NH and OH (Barbuceanu et al, 2014) groups and was carried out at ambient temperature. This made it possible to eliminate any risk of thermal degradation of labile molecules (Li et al, 2018). This test consisted of the reduction of an alcoholic solution of the radical species DPPH● in the presence of a hydrogen donor antioxidant (AH), which resulted in the formation of a non-radical form of DPPH-H
Summary
All reactions were monitored by TLC, silica gel F254, made by Merck, Germany. Melting points (oC) were measured in open glass capillaries using a Branstead 9001 Electrothermal melting point apparatus and were not corrected. The UV visible electron spectroscopy was recorded on an Optisen View 4.2 spectrometer. The IR spectra were recorded using KBr disks in a GENESISIIFTIR spectrophotometer, in ν units of cm−1. The 1H and 13C-NMR spectra (1D) were recorded on a Bruker AC 400 MHz spectrometer (University of Lyon 1, France) in DMSO-d6 and referenced to TMS. Mass spectra were obtained using a GC-MS CLARIS 500 (Laboratoire Régional de Police Scientifique d’Oran, Algeria). The microorganisms in this study were supplied and identified by the laboratory of microbiology by the university hospital of Oran. The Mueller Hinton medium was supplied by (Difco)
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