Isolation and characterization of some hydroxy fatty and phosphoric acid esters of 10-hydroxy-2-decenoic acid from the royal jelly of honeybees (Apis mellifera)
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The present work characterizes novel FA in the royal jelly of honeybees (Apis mellifera). TLC analysis showed that the chloroform/methanol extract obtained from royal jelly consists mainly of FA. The FABMS spectrum of this extract gave several ion peaks due to compounds with higher M.W. than those of the FA so far reported. The methanol extract was found to contain unknown phospholipids. By means of reversed-phase HPLC with various solvent systems, 13 compounds were obtained in pure state. Their structures including absolute configurations were determined by chemical, NMR, and MS spectral analysis. Six compounds were identified as novel mono- or diesters of 10-hydroxy-2E-decenoic acid in which the hydroxyl group was esterified by another FA unit, and one was hydroxy-2E-decenoic acid 10-phosphate. In addition, we demonstrated that 9-hydroxy-2E-decenoic acid exists as a mixture of optical isomers.
KeywordsDiester Royal Jelly Unknown Phospholipid Decenoate MTPA Ester
2-D heteronuclear multiple-bond correlation
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- 1.Tamura, T., Fuji, A., and Kubota, N. (1987) Anti-tumor Effects of Royal Jelly (RJ), Folia Pharmacol. Jpn. 89, 73–80 (in Japanese).Google Scholar
- 2.Sauerwald, N., Polster, J., Bengsch, E., Niessen, L., and Vogel, R.F. (1998) Combined Antibacterial and Antifungal Properties of Water-soluble Fraction of Royal Jelly, Adv. Food Sci. 20, 46–52.Google Scholar
- 3.Kamakura, M., Mitani, N., Fukuda, T., and Fukushima, M. (2001) Anti-fatigue Effect of Fresh Royal Jelly in Mice, J. Nutr. Sci. Vitaminol. (Tokyo) 47, 394–401.Google Scholar
- 5.Takenaka, T. (1982) Chemical Composition of Royal Jelly, Honeybee Sci. 3, 69–74.Google Scholar
- 10.Butenandt, A., and Rembold, H. (1957) Über den Weiselzellenfuttersaft der Honigbiene I. Isolierung, Konstitutionsermittlung und Vorkommen der 10-Hydroxy-Δ2-decensäure, Z. Physiol. Chem. 308, 284–289.Google Scholar
- 15.Dittmer, J.C., and Lester, R.L. (1964) Specific Spray for the Detection of Phospholipids on Thin-layer Chromatograms, J. Lipid Res. 5, 126–127.Google Scholar
- 17.Ono, M., Yamada, F., Noda, N., Kawasaki, T., and Miyahara, K. (1993) Determination by Mosher’s Method of the Absolute Configurations of Mono- and Dihydroxyfatty Acids Originated from Resin Glycosides, Chem. Pharm. Bull. (Tokyo) 41, 1023–1026.Google Scholar
- 18.Breitmaier, E., and Voelter, W. (1987) Carbon-13 NMR Spectroscopy, 3rd edn., pp. 250–254, VCH Verlagsgeselschaft, Weinheim.Google Scholar
- 19.Robinson, S.R. (1960) The Biological Activity and Synthesis of Royal Jelly Acid, Croat. Chem. Acta 32, 119–122.Google Scholar