Bioactive epoxides and hydroperoxides derived from naturally monoterpene geranyl acetate
Geranyl acetate (1) was oxidized thermally and photochemically using (mcpba, H2O2) respectively to obtain (E)-5-(3, 3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate (2) and 3-(2-(3, 3-dimethyloxiran-2-yl) ethyl)-3-methyloxiran-2-yl) methyl acetate (3). On the other hand, photooxygenation of 1 with...
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| Format: | Article |
| Language: | English |
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Elsevier
2018-01-01
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| Series: | Saudi Pharmaceutical Journal |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1319016417302001 |
| _version_ | 1818213641510453248 |
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| author | Suzan A. Khayyat Manal Y. Sameeh |
| author_facet | Suzan A. Khayyat Manal Y. Sameeh |
| author_sort | Suzan A. Khayyat |
| collection | DOAJ |
| description | Geranyl acetate (1) was oxidized thermally and photochemically using (mcpba, H2O2) respectively to obtain (E)-5-(3, 3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate (2) and 3-(2-(3, 3-dimethyloxiran-2-yl) ethyl)-3-methyloxiran-2-yl) methyl acetate (3). On the other hand, photooxygenation of 1 with tetraphenyl porphin (TPP) as a photo sensitizer gave corresponding acitic acid 2,6-bis-hydroperoxy-7-methyl-3-methylene-oct-7-enyl-ester (4), acitic acid 7-hydroperoxy-3,7-dimethyl-octa-2,5-dienyl ester (5) and Acitic acid 3-hydroperoxy-7-methyl-3,7-dimethyl-octa-1,6-dienyl ester (6). Antifungal studies were carried out on geranyl acetate and its derivatives. Studies on the antifungal activity especially Microsporum gypsum, Trichophyton vercossum and Candida tropicalis showed that geranyl acetate, its epoxide and hydroperoxide derivatives have good antifungal action. Keywords: Medicinal plants, Geranyl acetate, Hydroperoxide, epoxide, Photooxygenation, antifungal activity |
| first_indexed | 2024-12-12T06:07:31Z |
| format | Article |
| id | doaj.art-dcf9918ba8a344acb9479f1cfb75a6bd |
| institution | Directory Open Access Journal |
| issn | 1319-0164 |
| language | English |
| last_indexed | 2024-12-12T06:07:31Z |
| publishDate | 2018-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Saudi Pharmaceutical Journal |
| spelling | doaj.art-dcf9918ba8a344acb9479f1cfb75a6bd2022-12-22T00:35:16ZengElsevierSaudi Pharmaceutical Journal1319-01642018-01-012611419Bioactive epoxides and hydroperoxides derived from naturally monoterpene geranyl acetateSuzan A. Khayyat0Manal Y. Sameeh1Chemistry Department, Faculty of Science, King Abdulaziz University, P.O Box 55075-21534, Jeddah, Saudi Arabia; Corresponding author.Chemistry Department, Al-Leith College- Um Al-Qura University, Saudi ArabiaGeranyl acetate (1) was oxidized thermally and photochemically using (mcpba, H2O2) respectively to obtain (E)-5-(3, 3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate (2) and 3-(2-(3, 3-dimethyloxiran-2-yl) ethyl)-3-methyloxiran-2-yl) methyl acetate (3). On the other hand, photooxygenation of 1 with tetraphenyl porphin (TPP) as a photo sensitizer gave corresponding acitic acid 2,6-bis-hydroperoxy-7-methyl-3-methylene-oct-7-enyl-ester (4), acitic acid 7-hydroperoxy-3,7-dimethyl-octa-2,5-dienyl ester (5) and Acitic acid 3-hydroperoxy-7-methyl-3,7-dimethyl-octa-1,6-dienyl ester (6). Antifungal studies were carried out on geranyl acetate and its derivatives. Studies on the antifungal activity especially Microsporum gypsum, Trichophyton vercossum and Candida tropicalis showed that geranyl acetate, its epoxide and hydroperoxide derivatives have good antifungal action. Keywords: Medicinal plants, Geranyl acetate, Hydroperoxide, epoxide, Photooxygenation, antifungal activityhttp://www.sciencedirect.com/science/article/pii/S1319016417302001 |
| spellingShingle | Suzan A. Khayyat Manal Y. Sameeh Bioactive epoxides and hydroperoxides derived from naturally monoterpene geranyl acetate Saudi Pharmaceutical Journal |
| title | Bioactive epoxides and hydroperoxides derived from naturally monoterpene geranyl acetate |
| title_full | Bioactive epoxides and hydroperoxides derived from naturally monoterpene geranyl acetate |
| title_fullStr | Bioactive epoxides and hydroperoxides derived from naturally monoterpene geranyl acetate |
| title_full_unstemmed | Bioactive epoxides and hydroperoxides derived from naturally monoterpene geranyl acetate |
| title_short | Bioactive epoxides and hydroperoxides derived from naturally monoterpene geranyl acetate |
| title_sort | bioactive epoxides and hydroperoxides derived from naturally monoterpene geranyl acetate |
| url | http://www.sciencedirect.com/science/article/pii/S1319016417302001 |
| work_keys_str_mv | AT suzanakhayyat bioactiveepoxidesandhydroperoxidesderivedfromnaturallymonoterpenegeranylacetate AT manalysameeh bioactiveepoxidesandhydroperoxidesderivedfromnaturallymonoterpenegeranylacetate |