1-1-diphenyl-2-picrylhydrazyl and grandinin

Four polyphenolic acid derivatives and three ellagitannins were isolated from the leaves of Melaleuca quinquenervia (Clav.) S. T. Blake for the first time. Their structures were elucidated as gallic acid (1), ellagic acid (2), 3-O-methylellagic acid (3), 3,4,3'-tri-O-methylellagic acid (4), 2,3-O-hexahydroxydiphenoyl-(alpha/beta)-D-(4)C(1)-glucopyranose (5), castalin (6) and grandinin (7) on the basis of chemical, mass spectrometric (-ve ESI-MS) and spectroscopic (UV, (1)H-, (13)C NMR, (1)H,(1)H-, (1)H,(13)C-COSY, (1)H,(1)H-TOCSY and HMBC) analyses. Grandinin (the major compound) showed radical scavenging properties by its reaction with 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical [EC(50) = 4.3 +/- 0.3 micro g mL(-1)]. It was found to be relatively nontoxic in mice [LD(50) = 316 mg Kg(-1) b.wt.]. It exhibited a significant dose-dependent (35-70 mg Kg(-1)) hypoglycemic effect by significantly reducing blood glucose level in basal condition and after heavy glucose load in normal mice. Moreover, it reduced the elevated blood glucose level in STZ-induced diabetic mice. In addition, grandinin reduced the elevated blood urea nitrogen and serum lipid peroxides in STZ-induced diabetic mice.

Topics: Animals; Biphenyl Compounds; Blood Glucose; Diabetes Mellitus, Experimental; Dose-Response Relationship, Drug; Female; Flavonoids; Free Radical Scavengers; Glucose Tolerance Test; Glycosides; Heterocyclic Compounds, 4 or More Rings; Hypoglycemic Agents; Lethal Dose 50; Lipid Peroxidation; Male; Melaleuca; Mice; Phenols; Phytotherapy; Picrates; Plant Extracts; Plant Leaves; Polyphenols; Streptozocin; Thiobarbituric Acid Reactive Substances; Urea