A New Octadecenoic Acid Derivative from Caesalpinia gilliesii Flowers with Potent Hepatoprotective Activity

• Published in: Pharmacognosy Magazine Vol. 12; no. Suppl 3; pp. S332 - 336
• Main Authors: Osman, Samir M, El-Haddad, Alaadin E, El-Raey, Mohamed A, Abd El-Khalik, Soad M, Koheil, Mahmoud A, Wink, Michael
• Format: Journal Article
• Language: English
• Published: India Sage Publications Ltd 01.05.2016; Medknow Publications & Media Pvt Ltd
• Subjects: Antioxidants; Chromatography; Endoplasmic reticulum; Enzymes; Flavonoids; Free radicals; Liver; NMR; Nuclear magnetic resonance; Original; Oxidative stress; United States > US; Germany; Egypt; octadecenoic acid; isorhamnetin; fatty acid; aspartate aminotransferase and glutathione; hepatoprotective activity; plant phenolics; liver injury markers (alanine aminotransferase; Caesalpinia
• ISSN: 0973-1296; 0976-4062
• DOI: 10.4103/0973-1296.185752

Caesalpinia gilliesii Hook is an ornamental shrub with showy yellow flowers. It was used in folk medicine due to its contents of different classes of secondary metabolites. In our previous study, dichloromethane extract of C. gilliesii flowers showed a good antioxidant activity. Isolation and identification of bioactive hepatoprotective compounds from C. gilliesii flowers dichloromethane fraction. The hepatoprotective activity of dichloromethane fraction and isolated compounds were studied in CCl4-intoxicated rat liver slices by measuring liver injury markers (alanine aminotransferase, aspartate aminotransferase and glutathione [GSH]). All compounds were structurally elucidated on the basis of electron ionization-mass spectrometry, one- and two-dimensional nuclear magnetic resonance. A new 12,13,16-trihydroxy-14(Z)-octadecenoic acid was identified in addition to the known β-sitosterol-3-O-butyl, daucosterol, isorhamnetin, isorhamnetin-3-O-rhamnoside, luteolin-7,4'-dimethyl ether, genistein-5-methyl ether, luteolin-7-O-rhamnoside, isovanillic acid, and p-methoxybenzoic acid. Dichloromethane fraction and isorhamnetin were able to significantly protect the liver against intoxication. Moreover, the dichloromethane fraction and the isolated phytosterols induced GSH above the normal level. The hepatoprotective activity of C. gilliesii may be attributed to its high content of phytosterols and phenolic compounds. Bioactive Hepatoprotective phytosterols and phenolics from chloroform extract of Caesalpinia gilliesii Abbreviations used: ALT: Alanine Aminotransferase; AST: Aspartate aminotransferase; GSH: Glutathione; SC50: Scavenging Capacity 50 (SC 50); COSY: Correlation spectroscopy; NMR: Nuclear Magnetic Resonance; CC: Column chromatography; EI-MS: Electron-impact mass spectrometry; HSQC: Heteronuclear single-quantum correlation.