Antioxidative and anti-inflammatory pyranoids and isochromenyl analogues from Corbiculid bivalve clam, Villorita cyprinoides
Antioxidative and anti-inflammatory pyranoids and isochromenyl analogues from Corbiculid bivalve clam, Villorita cyprinoides
复制标题
DOI：
10.1016/j.foodchem.2018.01.059
复制
发表时间：
2018-06-15
期刊：
影响因子：
8.8
通讯作者：
Chakraborty, Kajal
中科院分区：
文献类型：
--
作者：
Joy, Minju;Chakraborty, Kajal
双壳类黑蛤是阿拉伯海西南海岸的传统海产品。本研究对黑蛤乙酸乙酯：甲醇提取物进行生物活性导向纯化。鉴定了两种不规则的部分萜类化合物{四氢-3-甲氧基-5-（（E）-8，12-二甲基辛-8-烯基）-吡喃-2-酮（1）和二氢-5-（8-（9，12-二氢-8-甲基-11-丙基-2H-吡喃-8-基）-乙基）-呋喃-2（3 H）-酮（2）}和两种六氢-异色烯基-部分萜类化合物（3-4）。通过详细的光谱学对其结构进行了表征，并对其抗氧化/抗炎潜力进行了评价。化合物2的2，2-二苯基-1-苦基肼（DPPH）自由基清除能力（IC 50 < 0.65 mg/mL）显著高于其他类似物（IC 50>= 0.70 mg/mL）。1-2的亚铁离子（Fe 2+）螯合能力（IC 50类似于0.84 mg/mL）高于α-生育酚（IC 50 0.89 mg/mL）。呋喃基部分萜类化合物2的5-脂氧合酶抑制活性（IC_（50）为0.76 mg/mL）大于其它化合物（IC_（50）> 0.90 mg/mL）。一个最佳的疏水-亲水平衡的呋喃-meroterpenoid和较小的空间体积表现出对它的更大的生物活性相比，其他化合物。这些抗炎和抗氧化的先导物可用作潜在的功能性食品成分。
Bivalve black clam, Villorita cyprinoides is traditional seafood in Southwestern coast of Arabian Sea. In this study, bioactivity-guided purification of ethyl acetate: methanol extract of black clam was carried out. Two irregular meroterpenoids {tetrahydro-3-methoxy-5-((E)-8,12-dimethyloct-8-enyl)-pyran-2-one (1) and dihydro-5-(8-(9,12-dihydro-8-methyl-11-propyl-2H-pyran-8-yl)-ethyl)-furan-2(3H)-one (2)} and two hexahydro-isochromenyl-meroterpenoids (3-4) were identified. The structures were characterized by detailed spectroscopy and their antioxidant/anti-inflammatory potentials were evaluated. Compound 2 registered significantly greater 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging ability (IC50 < 0.65 mg/mL) than other analogues (IC50 >= 0.70 mg/mL). Ferrous ion (Fe2+) chelating ability was higher for 1-2 (IC50 similar to 0.84 mg/mL) than alpha-tocopherol (IC50 0.89 mg/mL). The 5-lipoxygenase inhibitory potential of furano-meroterpenoid analogue, 2 (IC50 0.76 mg/mL) was greater than other compounds (IC50 > 0.90 mg/mL). An optimum hydrophobic-hydrophilic balance of furano-meroterpenoid and lesser steric bulk manifested towards its greater bioactivities compared to other compounds. These anti-inflammatory and antioxidant leads could be used as potential functional food components.