Constituents of Asparagus officinalis evaluated for inhibitory activity against cyclooxygenase-2.
As part of a project directed toward the discovery of new cancer chemopreventive agents from plants, two new natural products, asparagusic acid anti-S-oxide methyl ester (1) and asparagusic acid syn-S-oxide methyl ester (2), a new acetylenic compound, 2-hydroxyasparenyn [3',4'-trans-2-hydroxy-1-methoxy-4-[5-(4-methoxyphenoxy)-3-penten-1-ynyl]-benzene] (3), as well as eleven known compounds, asparenyn (4), asparenyol (5), (+/-)-1-monopalmitin (6), ferulic acid (7), 1,3-O-di-p-coumaroylglycerol (8), 1-O-feruloyl-3-O-p-coumaroylglycerol (9), blumenol C, (+/-)-epipinoresinol, linoleic acid, 1,3-O-diferuloylglycerol, and 1,2-O-diferuloylglycerol, were isolated from an ethyl acetate-soluble fraction of the methanol extract of the aerial parts of Asparagus officinalis (Asparagus), using a bioassay based on the inhibition of cyclooxygenase-2 to monitor chromatographic fractionation. The structures of compounds 1-3 were elucidated by 1D- and 2D-NMR experiments ((1)H NMR, (13)C NMR, DEPT, COSY, HMQC, HMBC and NOESY). All the isolates were evaluated for their inhibitory effects against both cyclooxygenase-1 and -2, with the most active compound being linoleic acid.
Jang
Dae Sik
DS
, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, USA.
Cuendet
Muriel
M
Fong
Harry H S
HH
Pezzuto
John M
JM
Kinghorn
A Douglas
AD
D027761:Asparagus Plant / Q000737:chemistry*; D003460:Crystallization; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007527:Isoenzymes / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol; D010936:Plant Extracts / Q000737:chemistry; D011451:Prostaglandin-Endoperoxide Synthases
D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D007527:Isoenzymes; D010936:Plant Extracts; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D011451:Prostaglandin-Endoperoxide Synthases; D000432:Methanol