Activity-guided fractionation of the seeds of Ziziphus jujuba using a cyclooxygenase-2 inhibitory assay.
Bioactivity-guided fractionation of petroleum ether- and EtOAc-soluble extracts of the seeds of Ziziphus jujuba using a cyclooxygenase-2 assay as a monitor indicated that the triglyceride, 1,3-di-O-[9(Z)-octadecenoyl]-2-O-[9(Z),12(Z)-octadecadienoyl]glycerol (3), and a fatty acid mixture of linoleic, oleic and stearic acids, were the major active components. A new pentacyclic lupane-type triterpene derivative, 3-O-[9(Z)-octadecenoyl]betulinic acid (1), and betulinic acid (2) were also isolated and identified. All isolates as well as pure linoleic, oleic and stearic acids were evaluated for their inhibitory effects against both cyclooxygenases-1 (COX-1) and -2 (COX-2).
Su
Bao-Ning
BN
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA.
Cuendet
Muriel
M
Farnsworth
Norman R
NR
Fong
Harry H S
HH
Pezzuto
John M
JM
Kinghorn
A Douglas
AD
D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000494:pharmacology*; D007527:Isoenzymes / Q000037:antagonists & inhibitors*; D019787:Linoleic Acid / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D019301:Oleic Acid / Q000494:pharmacology; D053978:Pentacyclic Triterpenes; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D011451:Prostaglandin-Endoperoxide Synthases; D012639:Seeds / Q000737:chemistry*; D013229:Stearic Acids / Q000494:pharmacology; D014280:Triglycerides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D031957:Ziziphus; D000094062:Betulinic Acid
C415322:1,3-di-(9-octadecenoyl)-2-(9,12-octadecadienoyl)glycerol; C472150:3-O-(9-octadecenoyl)betulinic acid; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D007527:Isoenzymes; D053978:Pentacyclic Triterpenes; D010936:Plant Extracts; D013229:Stearic Acids; D014280:Triglycerides; D014315:Triterpenes; D019301:Oleic Acid; C031183:stearic acid; D019787:Linoleic Acid; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D011451:Prostaglandin-Endoperoxide Synthases; D000094062:Betulinic Acid