Structure-function activity of dehydrozingerone and its derivatives as antioxidant and antimicrobial compounds.

Dehydrozingerone, structural half analogue of
curcumin, is a phenolic compound isolated from ginger
(Zingiber officinale) rhizomes. Dehydrozingerone and
several of its derivatives such as glucopyranosides and its
tetra acetate derivative and 4-O-acetyl and methyl derivatives
of dehydrozingerone were synthesized in the present
study. Dehydrozingerone, synthesised with improved yield
was used for the synthesis of Dehydrozingerone 4-O-β-Dglucopyranoside
(first time report) by modified Koenigs-
Knorr-Zemplén method. Structures of all the compounds
have been established using spectroscopic methods. These
compounds were tested for radical scavenging activity by
DPPH and FRAP method as well as for antibacterial and
antifungal activities. The parent molecule exhibited better
scavenging activity as compared to its derivatives indicating
the significance of free phenolic hydroxyl group. Also,
Dehydrozingerone and its derivatives exhibited antibacterial
as well as antifungal activity due to the conjugation system
present, which includes α,β-unsaturated carbonyl (C = O)
group. This study gave an insight into structural requirements
for dehydrozingerone activity.