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1.
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
2.
Zhifang Xi Wei Bie Wei Chen Dong Liu Leen van Ofwegen Peter Proksch Wenhan Lin 《Helvetica chimica acta》2013,96(12):2218-2227
Six new biscembranoids, namely, sarcophytolides G–L ( 1 – 6 , resp.), together with six known analogs, were isolated from a marine soft coral Sarcophyton elegans. The structures of the new compounds were established on the basis of 1D‐ and 2D‐NMR (COSY, HSQC, HMBC, and NOESY) spectroscopic analysis together with the aid of MS, CD, and IR data. The unusual isobiscembranoid sarcophytolide G ( 1 ) was found for the first time in the genus Sarcophyton. 相似文献
3.
Ahmed Abdel-Lateff Walied M. Alarif Seif-Eldin N. Ayyad Sultan S. Al-Lihaibi Salim A. Basaif 《Natural product research》2015,29(1):24-30
Chemical investigation of the soft coral Sarcophyton glaucum collected from the Red Sea led to isolation of 11 isoprenoidal metabolites (1–11). A new sesquiterpenoid, 6-oxo-germacra-4(15),8,11-triene (1), a new natural cembranoid, sarcophinediol, along with two known sesquiterpenoids (2 and 3) and seven known cembranoids (5–11) was obtained. The structures of the compounds were established based on their NMR, MS, IR and UV spectral data. All compounds were evaluated for their cytotoxicity employing three cancer cell lines (HepG2, MCF-7 and HCT116). Compounds 4 and 6 showed significant cytotoxicity towards HepG2 with IC50 values of 18.8 ± 0.07 and 19.9 ± 0.02 μM; respectively. Compounds 5–7 exhibited potent cytotoxicity against MCF-7 cells with IC50 values of 9.9 ± 0.03, 2.4 ± 0.04 and 3.2 ± 0.02 μM, respectively. Compounds 1, 4 and 5 showed significant activities towards HCT116 cells with IC50 values of 29.4 ± 0.03, 19.4 ± 0.02 and 25.8 ± 0.03 μM, respectively. 相似文献
4.
Two new cembranoid diterpenes, diepoxysarcophytonene ( 1 ) and sarconphytonol ( 2 ), were isolated from the Hainan soft coral Sarcophyton latum. Their structures including relative stereochemistry were established by 1D and 2D NMR spectroscopic techniques. Compound 1 showed weak inhibitory activity against COX‐2 in vitro at the concentration of 10?5 µmol·L?1 with the inhibitory rate of 55%. 相似文献
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6.
Liang Li Chang‐Yun Wang Chang‐Lun Shao Yue‐Wei Guo Guo‐Qiang Li Xue‐Ping Sun Lei Han Hui Huang Hua‐Shi Guan 《Helvetica chimica acta》2009,92(8):1495-1502
Chemical examination of the soft coral Sarcophyton infundibuliforme collected from the South China Sea resulted in the isolation of the three new O‐glycosylglycerol derivatives sarcoglycosides A–C ( 1 – 3 ), together with two known compounds, chimyl alcohol ( 4 ) and hexadecanol ( 5 ). Their structures were elucidated by combined spectral and chemical methods. All the compounds showed moderate toxicity to brine shrimps Artemia salina. 相似文献
7.
A new polyhydroxylated sterol, named sardisterol, was isolated from the soft coral Sarcophyton digitatum Moser. Its structure was determined as (22R, 24ξ)‐methylcholest‐5‐en‐3β, 22, 25, 28‐tetraol‐3‐acetate on the basis of spectroscopic methods. 相似文献
8.
Lin-Fu Liang Tibor Kurtán Attila Mándi Li-Gong Yao Jia Li Le-Fu Lan Yue-Wei Guo 《Tetrahedron》2018,74(15):1933-1941
A series of highly oxidative new cembranoids with diverse structural features such as a dienoate moiety (sarcophytonolides S – U, 1–3) or an α,β-unsaturated ε-lactone (sartrolides H – J, 4–6) were obtained from Hainan soft coral Sarcophyton trocheliophorum, along with known related analogues 7–13. It is an extremely challenging work to determine the absolute configurations of these metabolites. For compounds 1, 3 and 4, solution TDDFT calculation of ECD and specific rotation were applied in combination with conformational analysis and NMR data to determine their relative and absolute configurations, leading to the revision of relative configuration of 14. The absolute configurations of compounds 8–10 were determined by the solid-state TDDFT-ECD approach, and that of 8 was further confirmed by single-crystal X-ray diffraction experiment with Cu Kα radiation. In the bioassays, compound 8 exhibited not only moderate protein tyrosine phosphatase 1B (PTP1B) inhibitory activity (IC50?=?15.4?μM) but also moderate antibacterial activity against Staphylococcus aureus Newman strain (MIC50?=?250?μM). 相似文献
9.
Guey‐Horng Wang Jui‐Hsin Su Chien‐Ting Chen Chang‐Yih Duh Chang‐Feng Dai Jyh‐Horng Sheu 《中国化学会会志》2004,51(1):217-220
Two novel polyhydroxysteroids, (24S)‐24‐methylcholestane‐3β,5α,6β,25ξ;,26‐pentol 26‐n‐decanoate ( 1 ), (24S)‐24‐methylcholestane‐3β,5α,6β,25ξ;,26‐pentol 25,26‐diacetate ( 2 ), and three known sterols ( 3‐5 ), have been isolated from a Formosan soft coral Sarcophyton glaucum. The molecular structures of these compounds were determined by spectral methods. The cytotoxicity of these compounds toward various cancer cell lines has also been determined. 相似文献
10.
Ten new cembrane-type diterpenoids,namely xishaglaucumins A—J(1—10),along with ten known related ones(11—20),have been isolated from the soft coral Sarcophyton glaucum collected off the Xisha Island in the South China Sea.Their structures were elucidated by extensive spectroscopic analysis,quantum mechanical nuclear magnetic resonance(QM-NMR)methods,X-ray diffraction analysis,chemical methods and comparison with the reported data in the literature.The absolute configuration of new compounds 1,5 and known compounds 11,12,16 and 20 were determined either by chemical methods or by X-ray diffraction analysis using Cu Kα(λ=1.5417A).In in vitro bioassay,compound 4 exhibited inhibitory effects on lipopolysaccharide(LPS)-induced inflammatory responses in BV-2 microglial cells. 相似文献