Abstract

Green marine macroalgae, particularly Ulva lactuca, 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 U. lactuca, followed by its structural characterisation as 2-{(6a′-hydroxyethyl-4′-methyltetrahydro-2H-pyran-2′-one)-6′-yl}-4-methyl-7-ethylacetate-8-hydroxy-7, 8-dihydrobenzo [de]chromene. Ulvapyrone exhibited prospective inhibition property against arachidonate 5-lipoxygenase (IC₅₀ ∼1 mg mL⁻¹) comparable to that demonstrated by ibuprofen (IC₅₀ 0.9 mg mL⁻¹), which connoted its anti-inflammatory activity. The studied benzochromene exhibited promising antioxidant potential (IC₅₀ 0.5–0.6 mg mL⁻¹), 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⁻¹) with the allosteric site of 5-lipoxygenase. In silico 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，尤其是石莼，是许多亚洲国家美食的重要组成部分。本工作旨在从莴苣的有机提取物中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 ulvapyrone ，然后将其结构表征为 2-{(6a'-hydroxyethyl-4'-methyltetrahydro-2 H -pyran- 2'-one)-6'-yl}-4-methyl-7-ethylacetate-8-hydroxy-7, 8-dihydrobenzo [ de ]chromene。Ulvapyrone 对花生四烯酸 5-脂氧合酶 (IC ₅₀ ∼1 mg mL ^-1 ) 表现出与布洛芬 (IC ₅₀ 0.9 mg mL ^-1)，这意味着它的抗炎活性。所研究的苯并色烯表现出良好的抗氧化潜力（IC ₅₀ 0.5–0.6 mg mL ^-1），这进一步增强了其对 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~102）以及与5-脂氧合酶的变构位点的结合能较低（–8.22 kcal mol ^{-1 ）呈线性相关。}物理化学参数以及吸收、分布、代谢和排泄的计算机预测可以识别 ulvapyrone 可接受的口服生物利用度。