Cyclooxygenase-2 inhibitors in ginger (Zingiber officinale).
Ginger roots have been used to treat inflammation and have been reported to inhibit cyclooxygenase (COX). Ultrafiltration liquid chromatography mass spectrometry was used to screen a chloroform partition of a methanol extract of ginger roots for COX-2 ligands, and 10-gingerol, 12-gingerol, 8-shogaol, 10-shogaol, 6-gingerdione, 8-gingerdione, 10-gingerdione, 6-dehydro-10-gingerol, 6-paradol, and 8-paradol bound to the enzyme active site. Purified 10-gingerol, 8-shogaol and 10-shogaol inhibited COX-2 with IC(50) values of 32 μM, 17.5 μM and 7.5 μM, respectively. No inhibition of COX-1 was detected. Therefore, 10-gingerol, 8-shogaol and 10-shogaol inhibit COX-2 but not COX-1, which can explain, in part, the anti-inflammatory properties of ginger.
van Breemen
Richard B
RB
Department of Medicinal Chemistry and Pharmacognosy, University of Illinois College of Pharmacy, Chicago, IL 60612, USA. breemen@uic.edu
Tao
Yi
Y
Li
Wenkui
W
D002396:Catechols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002853:Chromatography, Liquid; D052246:Cyclooxygenase 2 Inhibitors / Q000737:chemistry / Q000302:isolation & purification*; D005233:Fatty Alcohols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D020939:Zingiber officinale / Q000737:chemistry*; D013058:Mass Spectrometry; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018517:Plant Roots
D002396:Catechols; D052246:Cyclooxygenase 2 Inhibitors; D005233:Fatty Alcohols; D010936:Plant Extracts; C007845:gingerol