Antioxidant and cyclooxygenase inhibitory phenolic compounds from Ocimum sanctum Linn.
Anti-oxidant bioassay-directed extraction of the fresh leaves and stems of Ocimum sanctum and purification of the extract yielded the following compounds; cirsilineol [1], cirsimaritin [2], isothymusin [3], isothymonin [4], apigenin [5], rosmarinic acid [6], and appreciable quantities of eugenol. The structures of compounds 1-6 were established using spectroscopic methods. Compounds 1 and 5 were isolated previously from O. sanctum whereas compounds 2 and 3 are here identified for the first time from O. sanctum. Eugenol, a major component of the volatile oil, and compounds 1, 3, 4, and 6 demonstrated good antioxidant activity at 10-microM concentrations. Anti-inflammatory activity or cyclooxygenase inhibitory activity of these compounds were observed. Eugenol demonstrated 97% cyclooxygenase-1 inhibitory activity when assayed at 1000-microM concentrations. Compounds 1, 2, and 4-6 displayed 37, 50, 37, 65, and 58% cyclooxygenase-1 inhibitory activity, respectively, when assayed at 1000-microM concentrations. Eugenol and compounds 1, 2, 5, and 6 demonstrated cyclooxygenase-2 inhibitory activity at slightly higher levels when assayed at 1000-microM concentrations. The activities of compounds 1-6 were comparable to ibuprofen, naproxen, and aspirin at 10-, 10-, and 1000-microM concentrations, respectively. These results support traditional uses of O. sanctum and identify the compounds responsible.
Kelm
M A
MA
Department of Horticulture and National Food Safety and Toxicology, Michigan State University, USA.
Nair
M G
MG
Strasburg
G M
GM
DeWitt
D L
DL
D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000302:isolation & purification; D000975:Antioxidants / Q000737:chemistry* / Q000302:isolation & purification; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry* / Q000302:isolation & purification; D006801:Humans; D007527:Isoenzymes / Q000037:antagonists & inhibitors / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008565:Membrane Proteins; D018649:Ocimum basilicum / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry* / Q000302:isolation & purification; D010936:Plant Extracts / Q000737:chemistry; D011451:Prostaglandin-Endoperoxide Synthases / Q000494:pharmacology
D000893:Anti-Inflammatory Agents; D000975:Antioxidants; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D007527:Isoenzymes; D008565:Membrane Proteins; D010636:Phenols; D010936:Plant Extracts; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; C496511:PTGS1 protein, human; C496540:PTGS2 protein, human; D011451:Prostaglandin-Endoperoxide Synthases