Antioxidant spiropharanone, an undescribed variant of trans-decalin spiro-γ-lactone, from pharaoh cuttlefish Sepia pharaonis: Twin inhibitors of inflammatory 5-lipoxygenase and serine protease dipeptidyl peptidase-4,Journal of Food Biochemistry

当前位置： X-MOL 学术 › J. Food Biochem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Antioxidant spiropharanone, an undescribed variant of trans-decalin spiro-γ-lactone, from pharaoh cuttlefish Sepia pharaonis: Twin inhibitors of inflammatory 5-lipoxygenase and serine protease dipeptidyl peptidase-4
Journal of Food Biochemistry ( IF 3.5 ) Pub Date : 2021-09-05 , DOI: 10.1111/jfbc.13919
Silpa Kunnappilly Paulose _{1,

2} , Kajal Chakraborty ₁

Affiliation

Marine pharaoh cuttlefish Sepia pharaonis (family Sepiidae) is regarded as an economically important class of cephalopod in the coastal Mediterranean and Asian regions. Bioassay-guided chromatographic purification of solvent extract of S. pharaonis led to the identification of a trans-decalin based spirolactone, spiropharanone, which was characterized as 1-hydroxy-7-(4′-methoxy-3-methylbut-2-enyl)-3,9,15-trimethyl-8-oxo-octahydro-5H-spiro[furan-8,9-naphtho]-8-yl-acetate by spectroscopic techniques. Spiropharanone exhibited significantly greater anti-inflammatory activity by attenuating pro-inflammatory 5-lipoxygenase (IC₅₀ 1.02 mM) than the non-steroidal drug ibuprofen (IC₅₀ 4.61 mM, p ≤ .05). Superior antioxidant properties of spiropharanone against free radicals (EC₅₀ ~1.20 mM) and other oxidants (hydroxyl [EC₅₀ 0.97 mM] and superoxide [EC₅₀ 1.47 mM] scavenging) also reinforced its promising anti-inflammatory activity. The studied spiropharanone also exhibited significant attenuation toward insulin secretion regulating enzyme dipeptidyl peptidase-4 (IC₅₀ 0.92 mM) recognizing its anti-hyperglycemic potential. Significantly higher electronic properties (topological polar surface area ~100) combined with balanced hydrophilic-lipophilic properties (partition coefficient of logarithmic octanol-water ~3) and lesser docking parameters of spiropharanone demonstrated that the compound could be utilized as an important bioactive lead against oxidative stress, inflammation, and hyperglycemic-related ailments.

中文翻译：

抗氧化螺菌酮，一种未描述的反式萘烷螺-γ-内酯变体，来自法老墨鱼 Sepia pharaonis：炎性 5-脂氧合酶和丝氨酸蛋白酶二肽基肽酶 4 的双重抑制剂

海洋法老乌贼Sepia pharaonis（Sepiidae 科）被认为是地中海沿岸和亚洲地区重要的头足类动物。S. pharaonis溶剂提取物的生物测定引导色谱纯化导致鉴定了一种基于反式十氢化萘的螺内酯螺内酯螺菌酮，其特征为 1-羟基-7-(4'-甲氧基-3-甲基丁-2-烯基) -3,9,15-trimethyl-8-oxo-octahydro- 5H -spiro [furan-8,9-naphtho]-8-yl-acetate 通过光谱技术。Spiropharanone 通过减弱促炎性 5-脂氧合酶 (IC ₅₀ 1.02 mM) 表现出比非甾体药物布洛芬 (IC ₅₀4.61 mM，p ≤ .05)。螺菌酮对自由基 (EC ₅₀ ~1.20 mM) 和其他氧化剂（羟基 [EC ₅₀ 0.97 mM] 和超氧化物 [EC ₅₀ 1.47 mM] 清除）的卓越抗氧化特性也增强了其有希望的抗炎活性。研究的螺菌酮也对胰岛素分泌调节酶二肽基肽酶-4 (IC ₅₀0.92 mM）识别其抗高血糖潜力。显着更高的电子特性（拓扑极性表面积~100）结合平衡的亲水亲油特性（对数辛醇-水的分配系数~3）和螺菌酮的较小对接参数表明该化合物可用作重要的生物活性铅对抗氧化压力、炎症和高血糖相关疾病。

更新日期：2021-10-06

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11