Food Research International ( IF 7.0 ) Pub Date : 2017-12-28 , DOI: 10.1016/j.foodres.2017.12.066 Minju Joy , Kajal Chakraborty
Villorita cyprinoides is traditional seafood in the coastal regions of Arabian Sea. Bioactivity-guided purification of ethyl acetate:methanol extract of V. cyprinoides resulted in the identification of two O-spirocyclic ether derivatives (1–2) along with one O-heterocyclic irregular meroterpenoid (3). The structures and their relative stereochemistries were elucidated through comprehensive spectroscopic experiments. These specialized metabolites were found to exhibit potential antioxidative (IC50 < 0.70 mg/mL) and anti-inflammatory activities against pro-inflammatory inducible 5-lipoxygenase (anti-5-LOX IC50 ≤ 0.80 mg/mL) and cyclooxygenase-2 (anti-COX-2 IC50 < 0.75 mg/mL) enzymes. Molecular docking simulations were used to describe the interactions of the isolated compounds (ligands) with COX-2 and 5-LOX inflammation model. The permissible hydrophobic-hydrophilic balance and lesser steric bulk of spirocyclic ether derivative (compound 2), along with greater number of hydrogen bonding interactions in the active sites of COX-2 and 5-LOX manifested towards its greater bioactivities compared to other compounds isolated from V. cyprinoides.
中文翻译:
赛诺尔菌中特有的氧化杂环具有环氧合酶-2和5-脂氧合酶的抑制特性
Villorita cyprinoides是阿拉伯海沿岸地区的传统海鲜。乙酸乙酯生物活性引导纯化:甲醇提取物V. cyprinoides产生了两个O形螺环醚衍生物(的识别1 - 2)与一种氧杂环不规则meroterpenoid(沿3)。通过全面的光谱实验阐明了其结构及其相对立体化学。发现这些专门的代谢物显示出潜在的抗氧化(IC 50 <0.70毫克/毫升)和对促炎症诱导的5-脂氧合酶的抗炎活性(抗5-LOX IC 50 ≤0.80毫克/毫升)和环氧合酶-2(抗COX-2 IC50 <0.75 mg / mL)酶。分子对接模拟用于描述分离的化合物(配体)与COX-2和5-LOX炎症模型的相互作用。与从其他化合物中分离得到的化合物相比,COX-2和5-LOX的活性位点具有更大的生物活性,因此可以实现疏水-亲水平衡和较小的螺环醚衍生物(化合物2)的空间体积,以及在COX-2和5-LOX的活性位点具有更多的氢键相互作用。V.cyprinoides。