title: Isolation of two new bioactive proanthocyanidins from Cistus salvifolius herb extract.
abstract: Two new proanthocyanidins, epigallocatechin-3-O-p-hydroxybenzoate-(4beta-->8)-epigallocatechin (1) and epigallocatechin-3-O-p-hydroxybenzoate-(4beta-->8)-epigallocatechin-3-O-gallate (2) in addition to the known compound epigallocatechin-(4beta-->6)-epigallocatechin-3-O-gallate (3), were isolated from the air-dried herb of Cistus salvifolius. The 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-catalysed degradation with phloroglucinol. The isolated compounds 1-3 and the water extract of C. salvifolius herb were tested for their inhibitory activities against COX-1 and COX-2. Compound 2 showed the strongest inhibitory effect on COX-2 followed by compound 3, compound 1 and the water extract, while compounds 1-3 exhibited moderate in vitro inhibition against COX-1.
authors.affiliation: Faculty of Pharmacy, The University of Petra, Jordan. fqadan@gmail.com
authors.forename: F
authors.initials: F
authors.lastname: Qa'dan
authors.forename: A
authors.initials: A
authors.lastname: Nahrstedt
authors.forename: M
authors.initials: M
authors.lastname: Schmidt
mesh_terms: D002942:Circular Dichroism; D029758:Cistus / Q000737:chemistry*; D051545:Cyclooxygenase 1 / Q000378:metabolism; D052246:Cyclooxygenase 2 Inhibitors / Q000494:pharmacology; D016861:Cyclooxygenase Inhibitors / Q000494:pharmacology; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D044945:Proanthocyanidins / Q000302:isolation & purification* / Q000494:pharmacology*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D007202:Indicators and Reagents; D010936:Plant Extracts; D044945:Proanthocyanidins; C559363:epigallocatechin-3-O-p-hydroxybenzoate-(4beta-8)-epigallocatechin; C559364:epigallocatechin-3-O-p-hydroxybenzoate-(4beta-8)-epigallocatechin-3-O-gallate; D051545:Cyclooxygenase 1