Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North, P.B. No. 1603, Cochin 682018, Kerala, India.
Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North, P.B. No. 1603, Cochin 682018, Kerala, India.
Food Chem. 2017 Dec 15;237:169-180. doi: 10.1016/j.foodchem.2017.05.087. Epub 2017 May 18.
Chemical investigation of ethyl acetate-methanol extract of the venerid bivalve clam Paphia malabarica led to isolation of three unprecedented aryl polyketide derivatives, characterized as (E)-12-(17-ethyl-tetrahydro-16-hydroxy-15-(methyl pentanoate)-14-oxo-2H-pyran-13-yl)-9-methyl-but-11-enyl benzoate (1), isobutyl-13-(6-(benzoyloxy)-10-methylpentyl)-tetrahydro-13-methyl-2H-pyran-17-carboxylate (2) and (13-(methoxycarbonyl)-11-((E)-18-ethylhexa-16,19-dienyl)-12-propyl-cyclohex-10-enyl)-methyl-3-hydroxy benzoate (3). The structures of the polyketides were assigned by extensive spectroscopic experiments. Compound 1 displayed comparatively greater 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical quenching potential (50% inhibitory concentration, IC ∼0.59mg/mL) than commercially available α-tocopherol (IC 0.63mg/mL). Potential pro-inflammatory 5-lipoxygenase (5-LOX) inhibition potential (IC 0.76-0.92mg/mL) of the polyketides in consonant with significantly greater anti-inflammatory selectivity indices (anti-cyclooxygense-1/anti-cyclooxygense-2>1) than non-steroidal anti-inflammatory agent ibuprofen (0.44) described the safety profile of the title compounds. Putative biosynthetic route by means of polyketide synthatase biocatalyzed pathways unambiguously established the structural assignments of the previously undescribed polyketide analogues. The potential of hitherto undescribed polyketides from P. malabarica as natural antioxidative and anti-inflammatory functional food ingredients was demonstrated in the present study.
从帘蛤科帘蛤属软体动物波纹巴非蛤的乙酸乙酯-甲醇提取物中分离得到三个结构新颖的芳基聚酮类衍生物，分别鉴定为（E）-12-（17-乙基-四氢-16-羟基-15-（甲基戊酸酯）-14-氧代-2H-吡喃-13-基）-9-甲基-丁-11-烯基苯甲酸酯（1）、异丁基-13-（6-（苯甲酰氧基）-10-甲基戊基）-四氢-13-甲基-2H-吡喃-17-羧酸酯（2）和（13-（甲氧基羰基）-11-（E）-18-乙基十六、19-二烯基）-12-丙基-环己-10-烯基）-甲基-3-羟基苯甲酸酯（3）。通过广泛的光谱实验确定了聚酮的结构。化合物 1 表现出比市售的α-生育酚（IC 0.63mg/mL）更大的 2,2-二苯基-1-苦基肼（DPPH）自由基淬灭潜力（50%抑制浓度，IC∼0.59mg/mL）。聚酮对潜在的促炎 5-脂氧合酶（5-LOX）的抑制潜力（IC 0.76-0.92mg/mL）与非甾体抗炎药布洛芬（0.44）相当，抗炎选择性指数（抗环氧化酶-1/抗环氧化酶-2>1）更高，描述了这些化合物的安全性特征。通过聚酮合酶生物催化途径提出的假定生物合成途径明确建立了以前未描述的聚酮类似物的结构分配。本研究表明，波纹巴非蛤中尚未描述的聚酮具有作为天然抗氧化和抗炎功能性食品成分的潜力。
