Gingerols derivatives

Based on the recent impressive progress made on asymmetric hydrolysis, the design and bio-transformation of the optically active ethyl 2,2-difluoro-3-hydroxyoctanoate 78 and synthesis of optically active fluorinated [6]-gingerol derivatives are reported [82]. The following criteria were used in the search for a practical route to chiral ethyl 2,2-difluoro-3-hydroxyoctanoate with a high -value (1) the search of an additive to enhance the enantioselectivity of asymmetric hydrolysis by lipases, and (2) the modification of ethyl 2,2-difluoro-... 

Chen, C. C., R. T. Rosen, and C. T. Ho. Chromatographic analyses of isomeric shogaol compounds derived from isolated gingerol compounds of ginger (Zingiber officinale Roscoe). J Chroma-togr 1986 360 175-184. 

The (R)-enantiomer of (242) has also been prepared and used as a chiral auxiliary in an enantioselective aldol synthesis of (+)-(S )-gingerol (79CB3703). (R )-Glutamic acid (246) was thus converted into (i )-pyroglutamic acid by simply heating in water. Conversion of (247) to its methyl ester and LAH reduction delivered alcohol (248). Ethyl nitrite treatment of (248) gave nitrosoamine (249), which was methylated to furnish (250). Exposure of (250) to LAH completed the synthesis of the required chiral auxiliary RAMP [(R)- l-amino-2-(methoxymethyl)pyrrolidine]. The hydrazone (252), derived from RAMP and acetone, was... 

Figure 7. Relationship of gingerol and derived compounds in ginger extracts (45)...

Zarate, R. and Yeoman, M.M. (1996) Changes in the amounts of [6]-gingerol and derivatives during a culture cycle of ginger, Zingiber officinale. Plant Science Limerick 121(1), 11 5-1 22. 

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. 

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... 

Phytochemicals are defined as nonnutritive, naturally occurring, and biologically active plant-derived chemicals that have health supporting, protective, and disease preventive properties. Several thousand phytochemicals (such as phenolics, carotenoids, allylic compounds, sterols, chlorophylls, indoles, sapoiuns, gingerols, and terpenes, among others) have been reported in fruits, vegetables, nuts, medicinal plants, herbal remedies, flowers, and red wines, among others [1-7]. Currently, there... 

Unsteady state models for the extraction of natural products. Data on the extraction of caffeine from green coffee beans [90, 102], lignin derivatives from wood particles [77], 6-gingerol from ginger rhizome [103], aromatic hydrocarbons from soil and oil from peanuts have been modelled. The unsteady state models of Kandiah and Spiro [103] (ginger) Goto et al. [77] (wood) and Bartle et al. [104] (soil) are discussed below. 

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