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Lipids

, Volume 40, Issue 8, pp 833–838 | Cite as

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)

  • Naoki Noda
  • Kazue Umebayashi
  • Takafumi Nakatani
  • Kazumoto Miyahara
  • Kaori Ishiyama
Articles

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 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.

Keywords

Diester Royal Jelly Unknown Phospholipid Decenoate MTPA Ester 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Abbreviations

HDA

hydroxy-2E-decenoic acid

HMBC

2-D heteronuclear multiple-bond correlation

MTPA

2-methoxy-2-trifluoromethylphenylacetate

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Copyright information

© AOCS Press 2005

Authors and Affiliations

  • Naoki Noda
    • 2
  • Kazue Umebayashi
    • 2
  • Takafumi Nakatani
    • 2
  • Kazumoto Miyahara
    • 2
  • Kaori Ishiyama
    • 1
  1. 1.Institute for Health ScienceYamada Apiculture Center, Inc.OkayamaJapan
  2. 2.Faculty of Pharmaceutical SciencesSetsunan UniversityOsakaJapan

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