Activity of p-Hydroxyphenyl Acrylate Derivatives
J. Agric. Food Chem., Vol. 52, No. 25, 2004 7483
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had a negligible activity. A3 and A4 were prepared in the
reaction of acryloyl chloride with cyclohexanol and 1-hexanol
instead of phenol, respectively. A3 and A4 were not active at
all both against the fungi and against the bacteria.
Paulus reported that a vinyl group situated in the R- and
â-position to an electronegative group exhibited antimicrobial
virtue by interacting with electrophilic sites of microbial cells
(10). The antimicrobial virtue became more prominent when a
resonance promoting group was bound to the electronegative
group. The importance of the resonance promoting group for
the antimicrobial virtue can be confirmed by comparing the halo
zone test results of A5 and A6 with those of A1. A5 was as
competent for the antimicrobial activity as A1, while A6 had
much less activity, although the nucleophilicity of the acryl
group and the resonance increasing effect of the phenyl group
of the latter are expected to be similar to those of A1.
Although A7 has two acryl groups, A7 was less active than
A1. One of the acryl groups in A7 acts like the acetyl one in
A8. Alkyl substituents in the phenyl ring differently affected
the antimicrobial activity. Ethyl in A9 slightly lowered the
activity, while dodecyl made A10 completely inactive. In
general, both the intrinsic activity and the diffusion rate of the
antimicrobial agent affect the halo zone test results, which
depend therefore on the molecular weight and the hydrophilicity
as well as on the electrophilicity.
The lower antimicrobial activity of A11 as compared to that
of A1 is attributed to the lack of the resonance increasing effect
of the phenyl group. It is curious to observe that A11 exhibits
some antimicrobial activity against both the fungi and the
bacteria, despite the resonance deficiency. In addition, A12
showed almost the same activity as A11, completely different
from A3 and A4 in terms of the resonance increasing effect.
Therefore, the stereoelectronic effect of the phenyl group in acryl
derivatives might play a certain role in their antimicrobial
activities.
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Shake flask tests were carried out for H5, A1, and A9 that
formed lager halo zones in the halo zone tests. Viable cells of
S. aureus were reduced by 100, 100, and 99.8%, and those of
P. aeruginosa were reduced by 100, 100, and 95.0%, respec-
tively, in the presence of H5, A1, and A9. The results from the
shake flask tests were in accord with those from the halo zone
tests.
The present study confirms that the acryl group plays a crucial
role in the antimicrobial activity of H5 and that a compound
with a vinyl electron withdrawing group and a resonance
promoting group is an excellent antimicrobial agent, as reported
by Paulus (10). However, an exception to this rule was
discovered in that A6 was far less active than A1.
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Received for review January 19, 2004. Revised manuscript received
August 9, 2004. Accepted August 15, 2004. This work was supported
by Grant No. R01-2002-000-046-0 from the interdisciplinary research
program of the KOSEF.
JF0499018