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. 2011 Jan;82(1):38-43.
doi: 10.1016/j.fitote.2010.09.004. Epub 2010 Sep 15.

Cyclooxygenase-2 inhibitors in ginger (Zingiber officinale)

Richard B van Breemen  1 , Yi Tao, Wenkui Li
Affiliations

Cyclooxygenase-2 inhibitors in ginger (Zingiber officinale)

Richard B van Breemen et al. Fitoterapia. 2011 Jan.

Abstract

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.

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Figures

Figure 1
Figure 1
Chemical structures of 10-gingerol and gingerol-related compounds from ginger root. In each group of compounds, the carbon atom on the alkyl side chain next to the phenyl ring is defined as C1. Using gingerol as an example, if n=4, 6, 8, or 10, then the compound is called 6-, 8-, 10-, or 12-gingerol.
Figure 2
Figure 2
Pulsed ultrafiltration mass spectrometric screening of a chloroform partition of a methanolic extract of ginger root for ligands to COX-2. LC-MS-MS with selected reaction monitoring (SRM) was used for the selective detection of gingerol-related compounds including A) 10-gingerol; B) 8-shogaol; C) 8-paradol; and D) 10-gingerdione and 6-dehydro-10-gingerol. Specific binding to COX-2 resulted in peak enhancement compared with control incubations without COX-2.
Figure 3
Figure 3
Dose-response curves for inhibition of COX-1 and COX-2 by the gingerol-related compounds 8-shogaol and 10-shogaol.
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