title: 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).
abstract: 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 di-esters 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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Setsunan University, Osaka, Japan. noda@pharm.setsunan.ac.jp
authors.forename: Naoki
authors.initials: N
authors.lastname: Noda
authors.forename: Kazue
authors.initials: K
authors.lastname: Umebayashi
authors.forename: Takafumi
authors.initials: T
authors.lastname: Nakatani
authors.forename: Kazumoto
authors.initials: K
authors.lastname: Miyahara
authors.forename: Kaori
authors.initials: K
authors.lastname: Ishiyama
mesh_terms: D000818:Animals; D001516:Bees; D004952:Esters; D005227:Fatty Acids / Q000737:chemistry*; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D010756:Phosphoric Acids / Q000737:chemistry / Q000302:isolation & purification*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D000099219:Royal Jelly
chemical_list: D004952:Esters; D005227:Fatty Acids; D005229:Fatty Acids, Monounsaturated; D010756:Phosphoric Acids; D000099219:Royal Jelly; C055543:10-hydroxy-2-decenoic acid