New pyranosyl cembranoid diterpenes from Sarcophyton trocheliophorum |
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| Authors: | Mohamed Shaaban Marwa Y Issa Mohamed A Ghani Abdelaaty Hamed Ahmed B Abdelwahab |
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| Institution: | 1. Institute of Organic and Biomolecular Chemistry, University of G?ttingen, G?ttingen, Germany;2. Chemistry of Natural Compounds Department, Pharmaceutical Industries Research Division, National Research Centre, Dokki-Cairo, Egyptmshaaba@gmail.com,?ms.attia@nrc.sci.eg;4. Faculty of Pharmacy, Pharmacognosy Department, Cairo University, Cairo, Egypt;5. Red Sea Marine Parks, Hurghada, Egypt;6. Faculty of Science, Chemistry Department, Al-Azhar University, Nasr City-Cairo, Egypt;7. Chemistry of Natural Compounds Department, Pharmaceutical Industries Research Division, National Research Centre, Dokki-Cairo, Egypt;8. Lorraine University, SRSMC, Boulevard Arago, France |
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| Abstract: | During our continual searching programme for novel bioactive metabolites from Sarcophyton trocheliophorum, collected from Red Sea, we describe herein the isolation and structural elucidation of further two new pyrane-based cembranoid diterpenes: 9-hydroxy-7,8-dehydro-sarcotrocheliol (1) and 8,9-expoy-sarcotrocheliol acetate (2), along with the well-known sarcotrocheliol acetate (3), (+)-sarcophine (4), (+)-sarcophytoxide (5) and (-)-sarcophytoxide (6). The chemical structures of compounds 1 and 2 were determined on the basis of 1D and 2D NMR (1H, 13C, 1H–1H COSY, HMQC, HMBC and NOE), mass spectra (ESI and HR-ESIMS) and by comparison with related structures. The antimicrobial activities of the reported compounds 1–6 were investigated. According to the molecular docking study of compounds 1–6 using 3D structure of α,β tubulin in complex with taxol (PDB code 1JFF) and epothilone A (PDB code 1TVK), sarcophine (4) displayed the highest affinity towards both crystal structures, followed by 5 and 6, meanwhile pyrane-based cembranoid diterpenes (1–3) showed less affinity. |
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| Keywords: | Pyrane-based cembranoids Sarcophyton trocheliophorum antimicrobial activities molecular docking |
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