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Mohamed Shaaban Marwa Y. Issa Mohamed A. Ghani Abdelaaty Hamed Ahmed B. Abdelwahab 《Natural product research》2019,33(1):24-33
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. 相似文献
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An efficient total synthesis of (±)-isocembrene via an intramolecular Stille cross-coupling reaction is described. A novel strategy towards the 1,3-diene-based cembrane-type macrocyclic diterpenoids has been realized. 相似文献
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Dr. Oskar Hoff Dr. Nicolas Kratena Daniya Aynetdinova Dr. Kirsten E. Christensen Prof. Timothy J. Donohoe 《Chemistry (Weinheim an der Bergstrasse, Germany)》2022,28(63):e202202464
In this work an approach for the synthesis of furanocembranoid natural products containing the C-7,8-diol moiety is disclosed. This culminated in the first total synthesis of the natural product molestin E, together with ent-sinulacembranolide A and ent-sinumaximol A as well as a thorough exploration of their chemistry. Late-stage ring-closure of the C-7,8-diols to the corresponding epoxides was also demonstrated. Key features of this synthetic strategy include a stereoselective Baylis-Hillman reaction, ring-closing metathesis and Shiina macrolactonisation. Chiral-pool materials were deployed to ensure the desired absolute stereochemistry which was confirmed by late-stage single crystal X-ray diffraction. 相似文献
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Abdelaaty Hamed Marwa Y. Issa Mohamed A. Ghani Marcel Frese Beate Neumann Hans Georg Stammler 《Natural product research》2019,33(20):3029-3032
Herein, we report the isolation and stereo-structure of rare pyrane-based cembranoid diterpenes, 9-hydroxy-7,8-dehydro-sarcotrocheliol (1) and sarcotrocheliol (2), from Sarcophyton trocheliophorum collected from Red Sea. Absolute configurations of both compounds were revised based on single crystal X-ray analyses. 相似文献
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