Lipids

, Volume 46, Issue 3, pp 263–270

The Absolute Configurations of Hydroxy Fatty Acids from the Royal Jelly of Honeybees (Apis mellifera)

Authors

  • Tetsuya Kodai
    • Faculty of Pharmaceutical SciencesSetsunan University
  • Takafumi Nakatani
    • Faculty of Pharmaceutical SciencesSetsunan University
    • Faculty of Pharmaceutical SciencesSetsunan University
Original Article

DOI: 10.1007/s11745-010-3497-x

Cite this article as:
Kodai, T., Nakatani, T. & Noda, N. Lipids (2011) 46: 263. doi:10.1007/s11745-010-3497-x

Abstract

9-Hydroxy-2E-decenoic acid (9-HDA) is a precursor of the queen-produced substance, 9-oxo-2E-decenoic acid (9-ODA), which has various important functions and roles for caste maintenance in honeybee colonies (Apis mellifera). 9-HDA in royal jelly is considered to be a metabolite of 9-ODA produced by worker bees, and it is fed back to the queen who then transforms it into 9-ODA. Recently we found that 9-HDA is present in royal jelly as a mixture of optical isomers (R:S, 2:1). The finding leads us to suspect that chiral fatty acids in royal jelly are precursors of semiochemicals. Rather than looking for semiochemicals in the mandibular glands of the queen bee, this study involves the search for precursors of pheromones from large quantities of royal jelly. Seven chiral hydroxy fatty acids, 9,10-dihydroxy-2E-decenoic, 4,10-dihydroxy-2E-decenoic, 4,9-dihydroxy-2E-decenoic, 3-hydroxydecanoic, 3,9-dihydroxydecanoic, 3,11-dihydroxydodecanoic, and 3,10-dihydroxydecanoic acids were isolated. The absolute configurations of these acids were determined using the modified Mosher’s method, and it was revealed that, similar to 9-HDA, five acids are present in royal jelly as mixtures of optical isomers.

Keywords

Absolute configurationApis melliferaHoneybeesHydroxy fatty acidModified Mosher’s methodRoyal jelly

Abbreviations

COSY

Two-dimensional 1H-1H shift correlation

HMBC

Two-dimensional heteronuclear multiple-bond connectivity

MTPA

2-Methoxy-2-(trifluoromethyl)phenylacetic acid

TMS

Tetramethylsilane

Copyright information

© AOCS 2010