Biosynthesis 10 -Gingerol

Kiuchi F, Iwakami S, Shibuya M, Hanaoka F, Sankawa U. (1992). Inhibition of prostaglandin and leukotriene biosynthesis by gingerols and diarylheptanoids. Chem Pharm Bull (Tol o). 40(2) 387-91. Kobayashi M, Shqji N, Ohizumi Y. (1987). Gingerol, a novel cardiotonic agent, activates the Ca2+-pumping ATPase in skeletal and cardiac sarcoplasmic reticulum. Biochim Biophys Acta. 903(1) 96-102. 

Hanaoka, and U. Sankawa. Inhibition of prostaglandin and leukotriene biosynthesis by gingerols and diaryl-heptanoids. Chem Pharm Bull 1992 40(2) 387-391. 

Ramirez Ahumada, M. del C., Timmermann, B.N. and Gang, D.R. (2006) Biosynthesis of curcuminoids and gingerols in turmeric (Curcuma longa) and ginger (Zingiber officinale) identification of curcuminoid synthase and hydroxycinnamoyl-CoA thioesterases. Phytochemistry 67(18), 201 7-2029. 

Initial investigations into the biosynthesis of the curcuminoids and gingerols were performed many years ago (Denniff and Whiting, 1976 Macleod and Whiting, 1979 Denniff et al., 1980). These initial radiotracer feeding studies suggested that these compounds were derived from intermediates in the phenylpropanoid pathways that were condensed with other molecules, derived in turn from the acetate and short-and medium-chain fatty acid pathways. 

Denniff, P. and Whiting, D.A. (1976) Biosynthesis of (6)-gingerol - the pungent principle of Zingiber officinale, journal of the Chemical Society for Chemical Communication 18, 711. 

Kiuchi, F., Iwakami, S., Shibuya, M., Hanaoka, F. and Sankawa, U. (1992) Inhibition of prostaglandin and leukot-riene biosynthesis by gingerols and diarylheptanoids. Chemical and Pharmaceutical Bulletin 40, 387-391. 

The biosynthesis of [6]-gingerol was investigated by administration of labelled precursors to whole Z. officinale plants [303, 305]. The hypothetical intermediates [6]-dehydrogingerdione (335), [6]-gingerdione (337) and [6]-dehydrogingerol (339), were synthesized and shown to be incorporated into [6]-gingerol [304]. A biosynthetic pathway for [6]-gingerol was then proposed as shown in "Fig. (4)". 

In addition to [6]-gingerol, four gingerdione derivatives, [6]- and [10]-dehydrogingerdione (335 and 336) and [6]- and [10]-gingerdione (337 and 338) were isolated from the root of Z. officinale [306]. These five compounds were potent inhibitors of prostaglandin (PG) biosynthesis and compounds 335-338 were more potent inhibitors than indomethacin which is known to be one of the strongest inhibitors [306]. Isolation of 335 and... 

Denniff, P., and D. A. Whiting Biosynthesis of [6]-Gingerol, Pungent Principle of Zingiber officinale. Chem. Commun. 711 (1976). 

---