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海白菜(Ulvaceae 科)中的吡喃酮连接的苯并色烯 Ulvapyrone:新型抗炎剂可减弱花生四烯酸 5-脂氧合酶。

Ulvapyrone, a pyrone-linked benzochromene from sea lettuce Linnaeus (family Ulvaceae): newly described anti-inflammatory agent attenuates arachidonate 5-lipoxygenase.

机构信息

Central Marine Fisheries Research Institute, Ernakulam North, Cochin, Kerala, India.

出版信息

Nat Prod Res. 2022 Aug;36(16):4114-4124. doi: 10.1080/14786419.2021.1976173. Epub 2021 Sep 20.

Abstract

Green marine macroalgae, particularly , is an essential constituent of the cuisines in many Asian countries. The present work aims to separate a bioactive pyrone attached benzochromene analogue, named as ulvapyrone from the organic extract of , followed by its structural characterisation as 2-{(6a'-hydroxyethyl-4'-methyltetrahydro-2-pyran-2'-one)-6'-yl}-4-methyl-7-ethylacetate-8-hydroxy-7, 8-dihydrobenzo []chromene. Ulvapyrone exhibited prospective inhibition property against arachidonate 5-lipoxygenase (IC ∼1 mg mL) comparable to that demonstrated by ibuprofen (IC 0.9 mg mL), which connoted its anti-inflammatory activity. The studied benzochromene exhibited promising antioxidant potential (IC 0.5-0.6 mg mL), which further reinforced its attenuation property against 5-lipoxygenase. Bioactivities of ulvapyrone were linearly correlated with electronic parameter (topological polar surface area ∼102) along with less binding energy (-8.22 kcal mol) with the allosteric site of 5-lipoxygenase. predictions of physicochemical parameters along with absorption, distribution, metabolism and excretion could recognise the acceptable oral bioavailability of ulvapyrone.

摘要

绿色海洋大型藻类,特别是,是许多亚洲国家美食的重要组成部分。本工作旨在从分离出一种具有生物活性的吡喃酮连接的苯并色烯类似物,命名为从的有机提取物中分离出来,随后对其进行结构表征为 2-{(6a'-羟乙基-4'-甲基四氢-2-吡喃-2'-酮)-6'-基}-4-甲基-7-乙基-8-羟基-7,8-二氢苯并[]色烯。Ulvapyrone 对花生四烯酸 5-脂氧合酶(IC ∼1 mg mL)表现出有前景的抑制作用,与布洛芬(IC 0.9 mg mL)相当,表明其具有抗炎活性。研究的苯并色烯表现出有希望的抗氧化潜力(IC 0.5-0.6 mg mL),进一步增强了其对 5-脂氧合酶的衰减特性。Ulvapyrone 的生物活性与电子参数(拓扑极性表面积约 102)呈线性相关,与 5-脂氧合酶的变构位点的结合能(-8.22 kcal mol)也较低。物理化学参数的预测以及吸收、分布、代谢和排泄,可识别 ulvapyrone 的可接受口服生物利用度。

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