Activity-Guided Fractionation of the Seeds of Ziziphus jujuba Using a Cyclooxygenase-2 Inhibitory Assay

Abstract

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).

References

• 1 Waffo-Teguo P, Lee D, Cuendet M, Merillon J M, Pezzuto J M, Kinghorn A D. Two new stilbene dimer glucosides from grape (Vitis vinifera) cell cultures.  Journal of Natural Products. 2001;  64 136-8
• 2 Cuendet M, Pezzuto J M. The role of cyclooxygenase and lipoxygenase in cancer chemoprevention.  Drug Metabolism and Drug Interactions. 2000;  17 109-57
• 3 Nick A, Wright A D, Rali T, Sticher O. Antibacterial triterpenoids from Dillenia papuana and their structure-activity relationships.  Phytochemistry. 1995;  40 1691-5
• 4 Peng C, Bodenhausen G, Qiu S, Fong H HS, Farnsworth N R, Yuan S, Zheng C. Computer-assisted structure elucidation: Application of CISOC-SES to the resonance assignment and structure generation of betulinic acid.  Magnetic Resonance in Chemistry. 1998;  36 267-78
• 5 Su B N, Takaishi Y. Morinins H-K, four novel phenylpropanol ester lipid metabolites from Morina chinensis .  Journal of Natural Products. 1999;  62 1325-7
• 6 Gunstone F D, Pollard M R, Scrimgeour C M, Vedanayagam H S. Fatty acids. Part 50. Carbon-13 nuclear magnetic resonance studies of olefinic fatty acids and esters.  Chemistry and Physics of Lipids. 1977;  18 115-29
• 7 Momin R A, Ramsewak R S, Nair M G. Bioactive compounds and 1,3-di[(cis)-9-octadecenoyl]-2-[(cis,cis)-9,12-octadecadienoyl]glycerol from Apium graveolens L. seeds.  Journal of Agricultural and Food Chemistry. 2000;  48 3785-8
• 8 Ko H R, Kim B Y, Lee H S, Kang D O, Ryu S H, Suh P G, Mheen T I, Ahn J S. Isolation and characterization of fatty acid derivatives from an Actinomycetes and examination of the effects on activities of phospholipase C and protein kinase C.  Journal of Microbiology (Seoul). 1998;  36 316-21
• 9 Ringbom T, Huss U, Stenholm Å, Flock S, Skattebøl L, Perera P, Bohlin L. COX-2 inhibitory effects of naturally occurring and modified fatty acids.  Journal of Natural Products. 2001;  64 745-9
• 10 Henry G E, Momin R A, Nair M G, Dewitt D L. Antioxidant and cyclooxygenase activities of fatty acids found in food.  Journal of Agricultural and Food Chemistry. 2002;  50 2231-4