Tagetnoic acid,a new lipoxygenase inhibitor peroxy fatty acid from Tagetes minuta growing in Saudi Arabia |
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| Authors: | Sabrin R M Ibrahim Gamal A Mohamed Rwaida A Al Haidari Amal A El-Kholy Mohamed F Zayed Maan T Khayat |
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| Institution: | 1. Department of Pharmacognosy and Pharmaceutical Chemistry, College of Pharmacy, Taibah University, Al Madinah Al Munawwarah, Saudi Arabia;2. Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut, Egypt;3. Ibrahimsabrinshaur@gmail.com sribrahim@taibahu.edu.sa;5. Department of Natural Products and Alternative Medicine, Faculty of Pharmacy, King Abdulaziz University, Jeddah, Saudi Arabia;6. Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut, Egypt;7. Department of Clinical and Hospital Pharmacy, College of Pharmacy, Taibah University, Al Madinah Al Munawwarah, Saudi Arabia;8. Department of Clinical Pharmacy, Faculty of Pharmacy, Ain-Shams University, Cairo, Egypt;9. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt;10. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, King Abdulaziz University, Jeddah, Saudi Arabia |
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| Abstract: | AbstractA new peroxy fatty acid, tagetnoic acid (5) 4-((3S,6S)-6-((3E,8E)-octadeca-3,8-dien-1-yl)-3,6-dihydro-1,2-dioxin-3-yl)butanoic acid] and four known metabolites: ecliptal (5-formyl-α-terthiophene) (1), 5-(4-hydroxybut-1-ynyl)-2,2′-bithiophene (2), 22,23-dihydrospinasterone (3), and stigmasterol (4) were separated from the n-hexane fraction of the aerial parts of Tagetes minuta L. (Asteraceae). Their chemical structures were verified using IR, UV, 2D and 1D NMR, and HRMS. Compounds 3–5 displayed potent lipoxygenase inhibitory potential with IC50s 2.26, 1.83, and 1.17?μM, respectively compared to indomethacin (IC50 0.89?μM). Moreover, molecular docking study revealed that the potent activity of 5 is due to H-bonding and hydrophobic interaction. The results of this study suggested that Tagetes minuta dietary consumption would be useful for the individuals at risk of acute and chronic inflammatory disorders. |
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| Keywords: | Tagetes minuta Asteraceae tagetnoic acid peroxy fatty acid lipoxygenase inhibitor molecular docking |
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