Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Cochin, India.
Department of Chemistry, Mangalore University, Mangaluru, India.
J Food Biochem. 2022 Jul;46(7):e14095. doi: 10.1111/jfbc.14095. Epub 2022 Feb 6.
Cephalopod cuttlefish, Sepia pharaonis, has been considered as a commercially important resource, which is widely regarded as nutritious food in the southwest of Indian and Mediterranean coasts. Chemical analysis of the crude extract of S. pharaonis resulted in the isolation of an undescribed 2H-benzochromenone, pharachromenone, which was characterized as methyl-2″-(7-hydroxy-4-(5'-methylpent-5'-en-1'-yl-oxy-methyl)-2-oxo-2H-benzo[h]chromen-5-yl-methyl)-butanoate by mass and nuclear magnetic resonance spectral experiments. Pharachromenone revealed effective biopotency against 5-lipoxygenase (IC 1.85 mM) and cyclooxygenase-2 (IC 0.52 mM) than that displayed by nonsteroidal anti-inflammatory drug ibuprofen (IC 4.36 mM, p < .05). Promising antioxidant property for pharachromenone (IC 1.42-1.61 mM) compared with those exhibited by antioxidative agents butylated hydroxyl anisole (BHA) and α-tocopherol (IC 1.40-1.90 mM) could conceivably validate its dual inhibition potential against 5-lipoxygenase and cyclooxygenase-2. Greater electronic parameters, lesser steric bulkiness, along with acceptable lipophilic-hydrophobic balance significantly contributed toward its promising anti-inflammatory activities. Molecular docking studies showing significantly greater inhibition constant (Ki) 8.24 nM and binding energy (-11.03 kcal/mol) of pharachromenone than the standard ibuprofen (Ki 4.65 μM, binding energy -7.27 kcal/mol) at the binding site of 5-lipoxygenase recognized its noncompetitive binding, which could describe the promising anti-inflammatory potential. Pharachromenone could be developed as a functional food component against oxidative stress-related inflammatory disorders. PRACTICAL APPLICATIONS: The cuttlefish Sepia pharaonis (family Sepiidae) comprises a major share in the global fishery sector due to its culinary delicacy and nutritionally valued high-quality meat. Furthermore, cephalopod mollusks are gaining pharmaceutical acceptance as resources to derive bioactive compounds with therapeutic significance. Bioassay-guided chromatographic fractionation of crude extract of S. pharaonis could result in the isolation of a 2H-benzochromenone derivative, pharachromenone exhibiting potent antioxidant and anti-inflammatory properties. This study recognized the therapeutic potential of a marine cuttlefish-originated food constituent against inflammatory conditions, and could be anticipated as a high-value functional food lead to minimize oxidative stress-related inflammatory disorders.
头足类乌贼，墨鱼，已被认为是一种具有商业价值的资源，在西南印度和地中海沿岸被广泛认为是一种营养丰富的食物。对 S. pharaonis 的粗提取物进行化学分析，得到了一种未被描述的 2H-苯并色酮，pharachromenone，其通过质谱和核磁共振谱实验被表征为甲基-2″-（7-羟基-4-（5'-甲基戊-5'-烯-1'-基-氧基-甲基）-2-氧代-2H-苯并[h]色烯-5-基-甲基）-丁酰基）。 Pharachromenone 对 5-脂氧合酶（IC 1.85 mM）和环氧化酶-2（IC 0.52 mM）的有效生物活性比非甾体抗炎药布洛芬（IC 4.36 mM，p <.05）更强。与抗氧化剂丁基羟基茴香醚（BHA）和 α-生育酚（IC 1.40-1.90 mM）相比， Pharachromenone 具有良好的抗氧化性能，这可能证明了它对 5-脂氧合酶和环氧化酶-2 的双重抑制潜力。更大的电子参数、更小的空间位阻以及可接受的亲脂性-疏水性平衡显著有助于其具有良好的抗炎活性。分子对接研究表明，与标准布洛芬（Ki 4.65 μM，结合能-7.27 kcal/mol）相比， Pharachromenone 在 5-脂氧合酶的结合部位的抑制常数（Ki）为 8.24 nM，结合能为-11.03 kcal/mol，表现出更强的抑制作用，这表明它具有非竞争性结合，这可以说明它具有良好的抗炎潜力。 Pharachromenone 可以作为一种功能性食品成分，用于对抗与氧化应激相关的炎症性疾病。实际应用：墨鱼 Sepia pharaonis（乌贼科）由于其美味的烹饪和营养价值高的优质肉质，在全球渔业中占有重要份额。此外，头足类软体动物作为具有治疗意义的生物活性化合物的资源，正在获得药物学的认可。对 S. pharaonis 粗提取物进行生物活性导向的色谱分离，可能得到一种 2H-苯并色酮衍生物，pharachromenone，具有很强的抗氧化和抗炎作用。这项研究认识到了一种来源于海洋乌贼的食物成分对炎症状态的治疗潜力，并有望成为一种高价值的功能性食品先导，以最小化与氧化应激相关的炎症性疾病。
