Chemical investigation of pharmacologically active compounds from the Echinoidea sea urchin Stomopneustes variolaris resulted in the separation of an unreported cembrane type of diterpenoid, which was characterised as 4-hydroxy-1-(16-methoxyprop-16-en-15-yl)-8-methyl-21,22-dioxatricyclo[11.3.1.1^5,8]octadecane-3,19-dione by spectroscopic experiments. The compound exhibited greater inhibitory potential against inflammatory agent 5-lipoxygenase (IC₅₀ 2.01 mM) than that exhibited by synthetic ibuprofen (IC₅₀ 4.50 mM). The selectivity ratio of cyclooxygenase-1 to cyclooxygenase-2 for the studied compound was found to be greater (1.25) than that of ibuprofen (0.43), which could be accounted for the prospective anti-inflammatory property of the cembrane-type diterpenoid against inducible pro-inflammatory cyclooxygenase-2. Potent antioxidant activity of the studied compound was characterised by its greater scavenging effects on 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis-3-ethylbenzothiozoline-6-sulfonic acid radicals (IC₅₀ 1.41 and 1.61 mM, respectively) than the standard antioxidative agent α-tocopherol (IC₅₀ 1.51 and 1.70 mM, respectively). The greater electronic parameters (topological polar surface area of 82.06) together with two hydrogen bonded interactions at the active site of cyclooxygenase-2 and lesser binding energy (−8.91 kcal/mol) corroborated its prospective anti-inflammatory activity. Therefore, the presently studied cembrane-type diterpenoid could be utilised in medicinal formulations as an effective anti-inflammatory agent.

中文翻译：

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海胆棘心from的抗氧化和消炎性膜状二萜类化合物可降解变应原性变脂酶5-脂氧合酶

对海胆棘心S药的药理活性化合物进行化学研究后，分离出未报告的二萜类化合物，其特征为4-羟基-1-（16-甲氧基丙-16-en-15-yl）-8 -甲基-21,22-二氧杂三环[11.3.1.1 ^5,8 ]十八烷-3,19-二酮的光谱实验。与合成布洛芬（IC ₅₀）相比，该化合物对炎性药物5-脂氧合酶（IC ₅₀ 2.01 mM）的抑制作用更大。4.50 mM）。发现所研究化合物的环氧合酶-1与环氧合酶-2的选择性比（1.25）大于布洛芬的选择性（0.43），这可以解释为该脑膜型二萜类化合物对诱导型化合物的预期抗炎特性。促炎性环氧合酶-2。所研究化合物的强抗氧化活性的特征在于其对2,2-二苯基-1-吡啶并肼基和2,2'-叠氮基-双-3-乙基苯并噻唑啉-6-磺酸基团的清除作用更大（IC ₅₀ 1.41和1.61 mM分别比标准抗氧化剂α-生育酚（IC ₅₀分别为1.51和1.70 mM。较高的电子参数（拓扑极性表面积为82.06）以及在环氧合酶2的活性位点处有两个氢键相互作用以及较小的结合能（-8.91 kcal / mol）证实了其预期的抗炎活性。因此，目前研究的西em型二萜可以作为有效的消炎剂用于药物制剂。