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Gingerols
Gingerols
are homologues of 1-(3-
methoxy-4-hydroxyphenyl)-3-keto-5-
h d h
d i l d th b
H
3
CO
CH
3
OH
O
1 2 3 4 5
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.
HO
[6]-Gingerol
OH
H
3
CO
HO
O
CH
3
(5
S
)-[8]-Gingerol
OH
H
3
CO
O
CH
3
HO
(5
R
)-[8]-Gingerol
OH
H
3
CO
HO
O
[10]-Gingerol
CH
3
Shogaols
Shogaols
are dehydration products of the
gingerols.
H
3
CO
CH
3
O
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
HO
[6]-Shogaol
H
3
CO
HO
O
CH
3
[8]-Shogaol
H
3
CO
O
CH
3
.
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.
HO
[10]-Shogaol