Diazole and triazole derivatives of castor oil extract: synthesis, hypoglycemic effect, antioxidant potential and antimicrobial activity
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)...
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| Format: | Article |
| Language: | English |
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Consejo Superior de Investigaciones Científicas
2020-12-01
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| Series: | Grasas y Aceites |
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| Online Access: | http://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/1849 |
| _version_ | 1818649272591056896 |
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| author | F. Taieb Brahimi F. Belkhadem B. Trari A. A. Othman |
| author_facet | F. Taieb Brahimi F. Belkhadem B. Trari A. A. Othman |
| author_sort | F. Taieb Brahimi |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-17T01:31:41Z |
| format | Article |
| id | doaj.art-bb54d700fb344ea5983ab8a83e62e4f3 |
| institution | Directory Open Access Journal |
| issn | 0017-3495 1988-4214 |
| language | English |
| last_indexed | 2024-12-17T01:31:41Z |
| publishDate | 2020-12-01 |
| publisher | Consejo Superior de Investigaciones Científicas |
| record_format | Article |
| series | Grasas y Aceites |
| spelling | doaj.art-bb54d700fb344ea5983ab8a83e62e4f32022-12-21T22:08:33ZengConsejo Superior de Investigaciones CientíficasGrasas y Aceites0017-34951988-42142020-12-01714e378e37810.3989/gya.03421911815Diazole and triazole derivatives of castor oil extract: synthesis, hypoglycemic effect, antioxidant potential and antimicrobial activityF. Taieb Brahimi0https://orcid.org/0000-0002-9460-8193F. Belkhadem1https://orcid.org/0000-0002-7113-7798B. Trari2https://orcid.org/0000-0001-7997-3638A. A. Othman3https://orcid.org/0000-0001-8116-4506Département de classe préparatoire, Ecole Supérieure en Génie Electrique et Energétique d’Oran - Laboratoire de Synthèse Organique Bioactive, Département de Chimie Organique Industrielle, Faculté de Chimie, Université des Sciences et de la Technologie d’OranLaboratoire de Synthèse Organique Bioactive, Département de Chimie Organique Industrielle, Faculté de Chimie, Université des Sciences et de la Technologie d’OranLaboratoire scientifique et technique régional de police ORANLaboratoire de Synthèse Organique Bioactive, Département de Chimie Organique Industrielle, Faculté de Chimie, Université des Sciences et de la Technologie d’OranThe 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.http://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/1849anti diabeticantimicrobialantioxidantcastor oilextractionheterocycle |
| spellingShingle | F. Taieb Brahimi F. Belkhadem B. Trari A. A. Othman Diazole and triazole derivatives of castor oil extract: synthesis, hypoglycemic effect, antioxidant potential and antimicrobial activity Grasas y Aceites anti diabetic antimicrobial antioxidant castor oil extraction heterocycle |
| title | Diazole and triazole derivatives of castor oil extract: synthesis, hypoglycemic effect, antioxidant potential and antimicrobial activity |
| title_full | Diazole and triazole derivatives of castor oil extract: synthesis, hypoglycemic effect, antioxidant potential and antimicrobial activity |
| title_fullStr | Diazole and triazole derivatives of castor oil extract: synthesis, hypoglycemic effect, antioxidant potential and antimicrobial activity |
| title_full_unstemmed | Diazole and triazole derivatives of castor oil extract: synthesis, hypoglycemic effect, antioxidant potential and antimicrobial activity |
| title_short | Diazole and triazole derivatives of castor oil extract: synthesis, hypoglycemic effect, antioxidant potential and antimicrobial activity |
| title_sort | diazole and triazole derivatives of castor oil extract synthesis hypoglycemic effect antioxidant potential and antimicrobial activity |
| topic | anti diabetic antimicrobial antioxidant castor oil extraction heterocycle |
| url | http://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/1849 |
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