Chemical investigations of the sea urchin Clypeaster humilis has led to separation of twelve compounds including one new sulfonic acid derivative (7R) 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 in vitro antiviral results. The pharmacokinetic properties (ADME) of isolated compounds were determined.

中文翻译：

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海胆 Clypeaster humilis 硫酸化专门代谢物的抗病毒活性：体外和计算机研究

对海胆Clypeaster humilis进行的化学研究分离了 12 种化合物，其中包括一种新的磺酸衍生物 (7 R ) tridec-1-en-7-yl 硫酸氢盐 ( 1 )，首次从天然来源，pyridine-3- 中分离出来。甲磺酸基酯 ( 2 )，以及首次从海洋生物中分离得到的 Bolline ( 12 )，以及首次从 Clypaster 属中分离出的9 种已知化合物 ( 3-11 )。基于光谱分析（一维和二维核磁共振）、HR-ESI-MS 以及与之前报道的数据的比较，阐明了它们的结构。使用 MTT 比色法评估粗提物和硫酸化化合物对柯萨奇 B4 病毒的抗病毒活性。粗提物和化合物1显示出非常有效的抗病毒活性，抑制百分比分别为 89.7 ± 0.53% 和 86.1 ± 0.92%。柯萨奇病毒B4（COX-B4）中分离化合物的分子对接分析结果和三种硫酸化化合物的X射线晶体结构和量子化学计算结果与体外抗病毒结果一致。测定了分离化合物的药代动力学特性（ADME）。