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Nat Prod Res. 2016 Sep;30(17):1919-26. doi: 10.1080/14786419.2015.1089242. Epub 2015 Sep 28.

Two new proanthocyanidin trimers isolated from Cistus incanus L. demonstrate potent anti-inflammatory activity and selectivity to cyclooxygenase isoenzymes inhibition.

Author information

1
a Faculty of Pharmacy & Medical Sciences, Department of Pharmaceutical Medicinal Chemistry , University of Petra , Amman , Jordan.
2
b Faculty of Health Sciences, Department of Medical Laboratories , American University of Madaba , Madaba , Jordan.
3
c HerbResearch , Mattsies , Germany.

Abstract

Two new proanthocyanidin trimers have been isolated from Cistus incanus herb; gallocatechin-(4α→6)-gallocatechin-(4α→8)-gallocatechin (compound 1) and epigallocatechin-3-O-gallate-(4ß→8)-epigallocatechin-3-O-gallate-(4ß→8)-gallocatechin (compound 2). The structures were determined on the basis of 1D- and 2D-NMR (HSQC, HMBC) of their peracetylated derivatives, MALDI-TOF-MS and by acid-catalysed degradation with phloroglucinol. A more abundant proanthocyanidin oligomer was also isolated, purified and its chemical constitution studied by (13)C-NMR and phloroglucinol degradation. The mean molecular weight of the polymer was estimated to be about 7 to 8 flavan-3-ol-units with a ratio of procyanidin : prodelphinidin units at 1:5, some of which are derivatised by gallic acid. Water extract and higher oligomeric proanthocyanidin fractions of C. incanus significantly inhibited TPA-induced oedema when applied topically at doses of 0.5 and 1 mg/ear in mice. Furthermore, the extracts and the pure compounds inhibited COX-1 and COX-2 activities. In addition, compound 2 exhibited an IC50 of 4.5 μM against COX-2 indicating its high selectivity towards COX-2.

KEYWORDS:

COX inhibitor; Cistus incanus; anti-inflammatory; phenolic; proanthocyanidins

PMID:
26414773
DOI:
10.1080/14786419.2015.1089242
[Indexed for MEDLINE]

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