1508 J. Agric. Food Chem., Vol. 58, No. 3, 2010
Cheng et al.
oleamide on gene expression in mammalian cells is still poorly
understood. Speculatively, the soporific effect (2, 5) and the
gene-modualting bioactivity of oleamide (4) other than the hypo-
lipidemic effect will become the main targets for further study.
In summary, the chemical synthesis of oleamide was shown to
be successful as confirmed by RP-HPLC (Figure 2), FTIR
(8) Sudhahar, V.; Shaw, S.; Imig, J. D. Mechanisms involved in
oleamide-induced vasorelaxation in rat mesenteric resistance
arteries. Eur. J. Pharmacol. 2009, 607 (1-3), 143–150.
(9) Solomonia, R.; Nozadze, M.; Mikautadze, E.; Kuchiashvili, N.;
Kiguradze, T.; Abkhazava, D.; Pkhakadze, V.; Mamulaishvili, I.;
Mikeladze, E.; Avaliani, N. Effect of oleamide on pentylenetetra-
zole-induced seizures in rats. Bull. Exp. Biol. Mol. 2008, 145 (2), 225–
227.
1
(Figure 3), HREIMS (Figure 4), H NMR (Figure 5), and 13C
NMR (Figure 6) in parallel to the elemental analysis (data not
shown). The product oleamide was identified to be an efficient
hypolipidemic but a poor antioxidative agent.
(10) Nojima, H.; Ohba, Y.; Kita, Y. Oleamide derivatives are proto-
typical anti-metastasis drugs that act by inhibiting Connexin 26.
Curr. Drug Saf. 2007, 2 (3), 204–211.
(11) Lo, Y. K.; Tang, K. Y.; Chang, W. N.; Lu, C. H.; Cheng, J. S.; Lee,
K. C.; Chou, K. J.; Liu, C. P.; Chen, W. C.; Su, W.; Law, Y. P.; Jan,
C. R. Effect of oleamide on Ca2þ signaling in human bladder cancer
cells. Biochem. Pharmacol. 2001, 62 (10), 1363–1369.
ABBREVIATIONS USED
MCS, mountain celery seeds; EOM, methanolic fractionate of the
mountain celery seed essential oil; ZOAM, 9(Z)-oleamide, 9(Z)-
octadecenamide, cis-9,10-octadecenoamide; FTIR, Fourier trans-
form infrared spectral analysis; 13C NMR, carbon-13 nuclear
(12) Chen, W. C.; Lin, M. C.; Chou, K. J.; Fang, H. C.; Liu, C. P.; Cheng,
J. S.; Lo, Y. K.; Lee, K. C.; Wang, J. L.; Su, W.; Law, Y. P.; Jan,
C. R. Novel effects of a sleep-inducing lipid, oleamide, on Ca2þ
signaling in renal tubular cells. Drug Dev. Res. 2001, 54, 40–44.
(13) Xu, M. Z.; Lee, W. S.; Kim, M. J.; Park, D. S.; Yu, H.; Tian, G. R.;
Jeong, T. S.; Park, H. Y. Acyl-CoA:cholesterol acyltransferase
inhibitory activities of fatty acid amide isolated from Mylabris
phalerate Pallas. Bioorg. Med. Chem. Lett. 2004, 14, 4277–4280.
(14) Shimada, K.; Fujikawa, K.; Yahara, K.; Nakamura, T. Antioxida-
tive properties of xanthane on the autoxidation of soybean oil in
cyclodextrin emulsion. J. Agric. Food Chem. 1992, 40, 945–948.
(15) Rinkus, S. J.; Taylor, R. T. Analysis of hydrogen peroxide in freshly
prepared coffees. Food Chem. Toxicol. 1990, 28, 323–331.
1
magnetic resonance spectrometer; H NMR, proton nuclear mag-
netic resonance spectrometer; HREIMS, high-resolution electron ion
mass spectrometer; MPLC, mass preparative liquid chromatogra-
phy; RP-HPLC, reverse phase high-performance chromatography.
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Received for review July 22, 2009. Revised manuscript received
December 19, 2009. Accepted December 27, 2009.