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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 )
Author(s) -
Noda Naoki,
Umebayashi Kazue,
Nakatani Takafumi,
Miyahara Kazumoto,
Ishiyama Kaori
Publication year - 2005
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-005-1445-6
Subject(s) - royal jelly , chemistry , methanol , phosphoric acid , chromatography , fatty acid , organic chemistry , solvent , chloroform , food science
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‐2 E ‐decenoic acid in which the hydroxyl group was esterified by another FA unit, and one was hydroxy‐2 E ‐decenoic acid 10‐phosphate. In addition, we demonstrated that 9‐hydroxy‐2 E ‐decenoic acid exists as a mixture of optical isomers.