Central Marine Fisheries Research Institute, Cochin, Kerala, India.
Department of Chemistry, Mangalore University, Mangalagangothri, Karnataka, India.
Nat Prod Res. 2020 Dec;34(24):3451-3461. doi: 10.1080/14786419.2019.1578761. Epub 2019 Mar 5.
The organic extract of , a brown seaweed harvested from the Gulf of Manner region of Indian peninsular was chromatographically fractionated to yield three substituted 2pyranoids, namely methyl-2-yl-[5', 6'- dihydro-5'-yl-{5-(4-hydroxybenzoyl)-oxy-(5-methylbutyl)}-3'-methyl-2-pyran]-2-methyl butanoate (), 11-[(3', 6'-dihydro-4'-methyl-2'-oxo-2-pyran-3'-yl)methyl]-10-methylhexyl benzoate (), and [6-ethyl-3,4-dimethyl-(tetrahydro-2', 2', 6'-trimethyl-2-pyran-3'-yl)-2,5-cycloheptadiene]-1-propanoate (). The compounds and bearing 2-pyranyl-4-hydroxybenzoyl and 2-pyranyl-10-methylhexylbenzoate moieties exhibited potential antioxidant activities (IC 0.54-0.69 mg mL) as commercial antioxidant (-tocopherol IC 0.63-0.73 mg mL). Likewise, potential bioactivity of the 2-pyran derivative, against 5-lipoxygenase (IC ∼ 1 mg mL) along with higher index of selectivity (COX-1 inhibitory/COX-2 inhibitory 1.88) indicated their selective anti-inflammatory properties against inducible inflammatory mediators than that displayed by commercially available non-steroidal anti-inflammatory drug (ibuprofen, 0.44). Structure activity relationship analysis of the studied compounds showed that the antioxidative and anti-inflammatory properties were directly proportional to their electronic properties. The previously undescribed pyranoids might constitute as potential antioxidative and anti-inflammatory pharmacophores for medicinal applications. [Formula: see text].
从印度半岛曼纳尔湾收获的褐藻中提取的有机提取物经色谱分离得到三种取代的 2-吡喃酮，分别为甲基-2-基-[5'，6'-二氢-5'-基-{5-（4-羟基苯甲酰基）-氧基-（5-甲基丁基）}-3'-甲基-2-吡喃]-2-甲基丁酸酯（）、11-[(3'，6'-二氢-4'-甲基-2'-氧代-2-吡喃-3'-基）甲基]-10-甲基己基苯甲酸酯（）和[6-乙基-3,4-二甲基-（四氢-2'，2'，6'-三甲基-2-吡喃-3'-基）-2,5-环庚二烯]-1-丙酸盐（）。化合物和具有 2-吡喃基-4-羟基苯甲酰基和 2-吡喃基-10-甲基己基苯甲酸酯部分，表现出潜在的抗氧化活性（IC 0.54-0.69 mg mL），类似于商业抗氧化剂（-生育酚 IC 0.63-0.73 mg mL）。同样，2-吡喃衍生物对 5-脂氧合酶的潜在生物活性（IC ∼ 1 mg mL）以及更高的选择性指数（COX-1 抑制/COX-2 抑制 1.88）表明，与市售非甾体抗炎药（布洛芬，0.44）相比，它们对诱导性炎症介质具有选择性抗炎作用。研究化合物的构效关系分析表明，抗氧化和抗炎性质与它们的电子性质直接相关。以前未描述的吡喃可能构成潜在的抗氧化和抗炎药物。
