Cyclooxygenase inhibitory and antioxidant compounds from the mycelia of the edible mushroom Grifola frondosa.
The bioassay-guided isolation and purification of the hexane extract of the cultured mycelia of Grifola frondosa led to the characterization of a fatty acid fraction and three compounds, ergosterol (1), ergostra-4,6,8(14),22-tetraen-3-one (2), and 1-oleoyl-2-linoleoyl-3-palmitoylglycerol (3). The composition of fatty acid fraction was confirmed as palmitic, oleic, and linoleic acids by GC-MS and by comparison with the retention values of authentic samples. The structures of compounds 1-3 were established by spectroscopic methods. The fatty acid fraction and compounds 1-3 showed cyclooxygenase (COX) enzyme inhibitory and antioxidant activities. The inhibition of COX-1 enzyme by the fatty acid fraction and compounds 1-3 at 250 microg/mL were 98, 37, 55, and 67%, respectively. Similarly, COX-2 enzyme activity was reduced by fatty acid fraction and compounds 1-3 at 250 microg/mL by 99, 37, 70, and 4%, respectively. The inhibitions of liposome peroxidation by the fatty acid fraction and compounds 1 and 2 at 100 microg/mL were 79, 48, and 42%, respectively. This is the first report of compounds 2 and 3 from the cultured mycelia of G. frondosa. The COX inhibitory activities of compounds 1-3 are reported here for the first time.
Zhang
Yanjun
Y
Bioactive Natural Products Laboratory, Department of Horticulture and National Food Safety and Toxicology Center, Biosystems Engineering, Michigan State University, East Lansing, Michigan 48824, USA.
Mills
Gary L
GL
Nair
Muraleedharan G
MG
D000363:Agaricales / Q000737:chemistry*; D000975:Antioxidants / Q000032:analysis* / Q000494:pharmacology; D002849:Chromatography, Gas; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000032:analysis* / Q000494:pharmacology; D004875:Ergosterol / Q000032:analysis / Q000494:pharmacology; D008401:Gas Chromatography-Mass Spectrometry; D007527:Isoenzymes / Q000037:antagonists & inhibitors; D019787:Linoleic Acid / Q000032:analysis / Q000494:pharmacology; D015227:Lipid Peroxidation / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D025282:Mycelium / Q000737:chemistry*; D019301:Oleic Acid / Q000032:analysis / Q000494:pharmacology; D019308:Palmitic Acid / Q000032:analysis / Q000494:pharmacology; D011451:Prostaglandin-Endoperoxide Synthases
D000975:Antioxidants; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D007527:Isoenzymes; D019301:Oleic Acid; D019308:Palmitic Acid; D019787:Linoleic Acid; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D011451:Prostaglandin-Endoperoxide Synthases; D004875:Ergosterol