A bioactive prodelphinidin from Mangifera indica leaf extract.
A new trimeric proanthocyanidin, epigallocatechin-3-O-gallat-(4beta-->8)-epigallocatechin-(4beta-->8)-catechin (1), was isolated together with three known flavan-3-ols, catechin (2), epicatechin (3), and epigallocatechin (4), and three dimeric proanthocyanidins, 5-7, from the air-dried leaves of Mangifera indica. Their chemical structures were determined on the basis of 1D- and 2D-NMR spectra (HSQC, HMBC) of their peracetylated derivatives, MALDI-TOF-mass spectra, and by acid-catalyzed degradation with phloroglucinol. The isolated compounds 1-7 were in vitro tested for their inhibitory activities against COX-1 and COX-2. Compound 1 was found to have a potent inhibitory effect on COX-2, while compounds 1 and 5-7 exhibited moderate inhibition against COX-1.
Tawaha
Khaled
K
Department of Pharmaceutical Sciences, Faculty of Pharmacy, University of Jordan, Amman 11942, Jordan.
Sadi
Rasha
R
Qa'dan
Fadi
F
Matalka
Khalid Z
KZ
Nahrstedt
Adolf
A
D000110:Acetylcholinesterase / Q000378:metabolism; D000818:Animals; D002392:Catechin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D051545:Cyclooxygenase 1 / Q000187:drug effects* / Q000378:metabolism; D052246:Cyclooxygenase 2 Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003576:Electron Transport Complex IV / Q000378:metabolism; D006003:Glycogen / Q000378:metabolism; D007770:L-Lactate Dehydrogenase / Q000378:metabolism; D007773:Lactates / Q000378:metabolism; D008195:Lymnaea / Q000187:drug effects / Q000235:genetics / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D031022:Mangifera / Q000737:chemistry*; D008958:Models, Molecular; D008974:Mollusca / Q000187:drug effects; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry*; D044945:Proanthocyanidins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011773:Pyruvates / Q000378:metabolism; D013385:Succinate Dehydrogenase / Q000378:metabolism
D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D007773:Lactates; D010936:Plant Extracts; D044945:Proanthocyanidins; D011773:Pyruvates; C013221:proanthocyanidin; D002392:Catechin; D006003:Glycogen; D007770:L-Lactate Dehydrogenase; D051545:Cyclooxygenase 1; D013385:Succinate Dehydrogenase; D003576:Electron Transport Complex IV; D000110:Acetylcholinesterase; C057580:gallocatechol