Abdelkarem Fahd M, Assaf Hamdy K, Mostafa Yaser A, Mahdy Aldoushy, Hussein Modather F, Ross Samir A, Mohamed Nesma M
Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University Assiut 71524 Egypt.
Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Assiut University Assiut 71526 Egypt.
RSC Adv. 2024 Apr 30;14(20):14185-14193. doi: 10.1039/d4ra01966k. eCollection 2024 Apr 25.
Chemical investigations of the sea urchin has led to separation of twelve compounds including one new sulfonic acid derivative (7) tridec-1-en-7-yl hydrogen sulphate (1), first isolated from natural source, pyridine-3-yl methane sulfonate (2), and first isolated from marine organisms, boldine (12), in addition to nine known compounds (3-11), which were isolated for the first time from the genus Clypeaster. Their structures were elucidated based on spectroscopic analyses (1D and 2D NMR), HR-ESI-MS as well as comparison with the previously reported data. The antiviral activity of the crude extract and sulphated compounds were evaluated using MTT colorimetric assay against Coxsackie B4 virus. The crude extract and compound 1 showed very potent antiviral activity with a percentage of inhibition equal to 89.7 ± 0.53% and 86.1 ± 0.92%, respectively. Results of the molecular docking analysis of the isolated compounds within Coxsackie Virus B4 (COX-B4) X-ray crystal structure and quantum chemical calculation for three sulphated compounds are in a consistent adaptation with the antiviral results. The pharmacokinetic properties (ADME) of isolated compounds were determined.
对海胆的化学研究已分离出十二种化合物，包括一种新的磺酸衍生物（7）十三碳 - 1 - 烯 - 7 - 基硫酸氢酯（1），这是首次从天然来源分离得到；吡啶 - 3 - 基甲磺酸盐（2），首次从海洋生物中分离得到；以及去氢骆驼蓬碱（12），此外还有九种已知化合物（3 - 11），这些化合物首次从砂海星属中分离得到。基于光谱分析（一维和二维核磁共振）、高分辨电喷雾电离质谱以及与先前报道数据的比较对它们的结构进行了阐明。使用MTT比色法针对柯萨奇B4病毒评估了粗提物和硫酸化化合物的抗病毒活性。粗提物和化合物1显示出非常强的抗病毒活性，抑制率分别为89.7±0.53%和86.1±0.92%。对分离出的化合物在柯萨奇病毒B4（COX - B4）X射线晶体结构内进行分子对接分析以及对三种硫酸化化合物进行量子化学计算的结果与抗病毒结果一致。测定了分离出的化合物的药代动力学性质（ADME）。
