Abstract

Chemical analysis of the organic extract from intertidal brown seaweed Sargassum ilicifolium (family Sargassaceae) characterised an undescribed xenicane-type diterpenoid sargilicixenicane, elucidated as 3-(17-hydroxy-14-methylhept-13-en-10-yl)-6-methylhexahydro-1H-cyclonona[c]furan-4,19-diyl diacetate (compound 1). The studied compound exhibited prospective free radical quenching potential (IC₅₀ 1.2-1.4 mM) in comparison with commercial antioxidant (α-tocopherol, IC₅₀ > 1.40 mM). Attenuation property of sargilicixenicane against pro-inflammatory enzyme, 5-lipoxygenase (IC₅₀ 4.70 mM) was comparable with that displayed by the non-steroidal anti-inflammatory agent ibuprofen (IC₅₀ 4.51 mM). Greater selectivity index displayed by the studied xenicane-type diterpenoid (1.42) than that exhibited by ibuprofen (0.44) recognised the selective attenuation potential of the former against the inducible cyclooxygenase-2 and 5-lipoxygenase enzymes. Higher electronic parameters (topological polar surface area, 82.06) and balanced hydrophobic-hydrophilic property (octanol-water partition coefficient 2.94) coupled with docking score (-11.17 kcal mol⁻¹) and lower binding energy (-9.61 kcal mol⁻¹) with the active site of 5-lipoxygenase supported the significant anti-inflammatory properties of the studied xenicane-type diterpenoid.

 抽象的

对潮间带棕色海藻马尾藻（马尾藻科）有机提取物的化学分析表征了一种未描述的 xenicane 型二萜 sargilicixenicane，被阐明为 3-(17-羟基-14-甲基庚-13-en-10-基)-6-甲基六氢-1 H-环壬[c]呋喃-4,19-二乙酸二酯（化合物1）。与商业抗氧化剂（ α-生育酚，IC ₅₀ > 1.40 mM）相比，所研究的化合物表现出潜在的自由基猝灭潜力（IC ₅₀ 1.2-1.4 mM）。 sargilicixenicane 对促炎酶 5-脂氧合酶 (IC ₅₀ 4.70 mM) 的衰减特性与非甾体抗炎剂布洛芬 (IC ₅₀ 4.51 mM) 所显示的衰减特性相当。所研究的 xenicane 型二萜类化合物 (1.42) 所显示的选择性指数比布洛芬 (0.44) 所显示的选择性指数更高，这表明前者对诱导型环氧合酶 2 和 5-脂氧合酶具有选择性减弱潜力。较高的电子参数（拓扑极性表面积，82.06）和平衡的疏水-亲水特性（辛醇-水分配系数2.94）加上对接分数（-11.17 kcal mol ^-1 ）和较低的结合能（-9.61 kcal mol ^-1 ） 5-脂氧合酶的活性位点支持了所研究的 xenicane 型二萜类化合物的显着抗炎特性。