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

Content Provider	Springer Nature Link
Author	Kodai, Tetsuya Nakatani, Takafumi da, Naoki
Copyright Year	2010
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.
Starting Page	263
Ending Page	270
Page Count	8
File Format	PDF
ISSN	00244201
Journal	Lipids
Volume Number	46
Issue Number	3
e-ISSN	15589307
Language	English
Publisher	Springer-Verlag
Publisher Date	2010-11-17
Publisher Place	Berlin, Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Absolute configuration Apis mellifera Honeybees Hydroxy fatty acid Modified Mosher’s method Royal jelly Medical Biochemistry Neurochemistry Medicinal Chemistry Lipidology Nutrition Microbial Genetics and Genomics
Content Type	Text
Resource Type	Article
Subject	Cell Biology Organic Chemistry Biochemistry

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