Novel furanyl derivatives from the red seaweed Gracilaria opuntia with pharmacological activities using different in vitro models

AbstractTwo previously undescribed furanyl compounds, characterized as 5-(7-(5-ethyl-3,4-dimethoxycyclooctyl) benzofuran-6-yl)-7-methyl-3,4,7,8-tetrahydro-2H-oxocin-2-one (compound1) and 2-(3-ethyl-9-(2-methoxyethoxy)-1-oxo-2,3,4,9-tetrahydro-1H-xanthen-2-yl) ethyl-5-hydroxy-9-methoxy-7,8-dimethyl-8-(5-methylfuran-2-yl) nona-3,6-dienoate (compound2) were derived from the ethyl acetate –methanol (EtOAc:MeOH) crude extract of red seaweedGracilaria opuntia. The isolated compounds are the first furanyl natural products featuring methoxycyclooctyl benzofuran with tetrahydro-2H-oxocin framework and tetrahydro-1H-xanthenyl methoxy methylfuran skeletons. These compounds were assessed for anti-inflammatory activities against pro-inflammatory cyclooxygenase-2/5-lipoxygenase (COX-1, 2, and 5-LOX) and antioxidative effects in various in vitro models. The methylfuran derivative exhibited comparable inhibitory activities towards 5 LOX (IC50 0.209  × 10−2 M) with synthetic non-steroidal anti-inflammatory drugs (NSAID) ibuprofen (IC50 0.451  × 10−2 M,P < 0.05), which indicated its potential anti-inflammatory properties. The antioxidative properties of the furanyl derivatives as resolved by 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2ʹ-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid (ABTS) free radical scavenging activities were found to be sig nificantly greater (IC50 ~0.051 –0.055 × 10−2 M) than those exhibited by α-tocopherol (IC50 >  0.146 ...
Source: Medicinal Chemistry Research - Category: Chemistry Source Type: research