September 2016 SPDS Book

Gingerols

O

OH

Gingerols are homologues of 1-(3- methoxy-4-hydroxyphenyl)-3-keto-5- h d h d i l d th b y roxy exane an nc u e e su group methylgingerols . Universally acknowledged as major constituents of ginger “pungent principles”. Gingerols are thermally labile and undergo chemical changes during processing and storage.

H 3 CO

1 2 3 4 5

CH 3

[6]-Gingerol

HO

O

OH

H 3 CO

CH 3

(5 S )-[8]-Gingerol

HO

O

OH

H 3 CO

CH 3

(5 R )-[8]-Gingerol

HO

O

OH

H 3 CO

CH 3

[10]-Gingerol

HO

Shogaols

O

Shogaols are dehydration products of the gingerols. Sometimes considered the degradation products of gingerols, shogaols, in fact were found to readily interconvert into gingerols at specific conditions. Shogaols are strong contributors to ginger “pungent principles”. Thermal treatment of ginger rhizome is commonly undertaken to enhance content of shogaols [6]-Shogaol . is considered a more “pungent” constituent relative to [6]-gingerol, and in numerous bioactivity studies was shown to outperform the latter. Content of shogaols increases significantly in ginger extracts.

H 3

CO

CH 3

[6]-Shogaol

HO

O

H 3

CO

CH 3

[8]-Shogaol

HO

O

H 3

CO

CH 3

[10]-Shogaol

HO