Fresh organically grown ginger (Zingiber officinale): composition and effects on LPS-induced PGE2 production.
Gas chromatography in conjunction with mass spectrometry, a technique previously employed to analyze non-volatile pungent components of ginger extracts modified to trimethylsilyl derivatives, was applied successfully for the first time to analyze unmodified partially purified fractions from the dichloromethane extracts of organically grown samples of fresh Chinese white and Japanese yellow varieties of ginger, Zingiber officinale Roscoe (Zingiberaceae). This analysis resulted in the detection of 20 hitherto unknown natural products and 31 compounds previously reported as ginger constituents. These include paradols, dihydroparadols, gingerols, acetyl derivatives of gingerols, shogaols, 3-dihydroshogaols, gingerdiols, mono- and diacetyl derivatives of gingerdiols, 1-dehydrogingerdiones, diarylheptanoids, and methyl ether derivatives of some of these compounds. The thermal degradation of gingerols to gingerone, shogaols, and related compounds was demonstrated. The major constituent in the two varieties was [6]-gingerol, a chemical marker for Z. officinale. Mass spectral fragmentation patterns for all the compounds are described and interpreted. Anti-inflammatory activities of silica gel chromatography fractions were tested using an in vitro PGE2 assay. Most of the fractions containing gingerols and/or gingerol derivatives showed excellent inhibition of LPS-induced PGE2 production.
Arizona Center for Phytomedicine Research, College of Pharmacy, University of Arizona, Tucson, AZ 85721, USA.
Shivanand D
SD
Jolad
R Clark
RC
Lantz
Aniko M
AM
Solyom
Guan Jie
GJ
Chen
Robert B
RB
Bates
Barbara N
BN
Timmermann
D000383:Agriculture / Q000379:methods*; D000893:Anti-Inflammatory Agents / Q000737:chemistry; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D015232:Dinoprostone / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D020939:Zingiber officinale / Q000737:chemistry* / Q000254:growth & development; D008956:Models, Chemical; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification; D013816:Thermodynamics
D000893:Anti-Inflammatory Agents; D010936:Plant Extracts; D015232:Dinoprostone