Anti-inflammatory polyoxygenated furanocembranoids, salmacembranes A –B from the sea urchin Salmacis bicolor attenuate pro-inflammatory cyclooxygenases and lipoxygenase

AbstractTwo undescribed polyoxygenated furanocembranoid derivatives, methyl 15-(9-hydroxy-8-methoxy-2,12-dimethyl-15-oxa-bicyclo[10.2.1]pentadeca-2,4,6,11-tetraen-3-yl)propanoate (salmacembrane A) and 1-(16-methyl-2,16-dihydrofuran)-8-methoxy-12-methyl-20-oxabicyclo[10.2.1]pentadeca-2,4,6,11-tetraen-9-ol (salmacembrane B), were isolated from the organic extract of sea urchinSalmacis bicolor (family Temnopleuridae) by extensive chromatographic purification. Their structures were elucidated using detailed spectroscopic evidence. Salmacembrane A displayed significantly greater attenuation property against pro-inflammatory cyclooxygenase-2 (IC50 1.71  mM) than that exhibited by salmacembrane B (IC50 1.99  mM). Salmacembrane A could potentially inhibit 5-lipoxygenase (IC50 1.87  mM) and its activity was significantly greater than that exhibited by anti-inflammatory agent ibuprofen (IC50 4.50  mM,p <  0.05). The greater selectivity index (anti-cyclooxygense-2/anti-cyclooxygense-1) of salmacembrane A (1.06) than ibuprofen (0.43) further supported higher selectivity toward pro-inflammatory isoenzyme cyclooxygenase-2. Salmacembrane A displayed higher antioxidant properties against 2,2′-azino-bi s(3-ethylbenzothiazoline-6-sulfonic acid) and 2,2-diphenyl-1-picrylhydrazyl (IC50 1.57 and 1.65  mM, respectively) than those exhibited by salmacembrane B (IC50 >  1.85 mM). In addition, these antioxidant activities were comparable to the standardα-tocopherol (IC50 ...
Source: Medicinal Chemistry Research - Category: Chemistry Source Type: research