Biological Origin and Configuration of 10-Hydroxy-Δ2-decenoic Acid

Barker, S. A.; Foster, A. B.; Lamb, David C.; Jackman, L. M.

doi:10.1038/184634a0

Cited by 38 publications

(8 citation statements)

References 8 publications

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“…The remainder of the royal jelly is composed of an ether‐soluble fraction of fatty acids. This fatty acid component is comprised primarily of a single compound—10HDA (Barker et al , 1959). 10HDA contributes 2–6% of the wet weight of royal jelly, depending on the source, making it the dominant small molecule in this secretion.…”

Section: Discussionmentioning

confidence: 99%

Histone deacetylase inhibitor activity in royal jelly might facilitate caste switching in bees

et al. 2011

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Worker and queen bees are genetically indistinguishable. However, queen bees are fertile, larger and have a longer lifespan than their female worker counterparts. Differential feeding of larvae with royal jelly controls this caste switching. There is emerging evidence that the queen-bee phenotype is driven by epigenetic mechanisms. In this study, we show that royal jelly-the secretion produced by the hypopharyngeal and mandibular glands of worker bees-has histone deacetylase inhibitor (HDACi) activity. A fatty acid, (E)-10-hydroxy-2-decenoic acid (10HDA), which accounts for up to 5% of royal jelly, harbours this HDACi activity. Furthermore, 10HDA can reactivate the expression of epigenetically silenced genes in mammalian cells. Thus, the epigenetic regulation of queen-bee development is probably driven, in part, by HDACi activity in royal jelly.

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Section: Discussionmentioning

confidence: 99%

Histone deacetylase inhibitor activity in royal jelly might facilitate caste switching in bees

et al. 2011

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“…QMP regulates critical traits in honey bee social organization based on reproductive division of labor and worker division of labor 5, 6 , including the induction of worker retinue response 7 , the attraction of drones 8 and the inhibition of worker ovary development 9 . In contrast, worker MGs mainly produce ω-hydroxylated decenoic acids 10 , including 10-hydroxy-2-decenoic acid (10-HDA) and its precursor 10-hydroxy-decanoic acid (10-HDAA), which account for 60–80% of the total fatty acid composition of royal jelly 11, 12 and influence larval growth 13 .…”

Section: Introductionmentioning

confidence: 99%

Comparative transcriptome analysis on the synthesis pathway of honey bee (Apis mellifera) mandibular gland secretions

Zheng

Corona³

et al. 2017

Sci Rep

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Secretions from mandibular glands (MGs) have important caste-specific functions that are associated with the social evolution of honey bees. To gain insights into the molecular architecture underlying these caste differences, we compared the gene expression patterns of MGs from queens, queenright workers (WQRs) and queenless workers (WQLs) using high-throughput RNA-sequencing technology. In total, we identified 46 candidate genes associated with caste-specific biosynthesis of fatty acid pheromones in the MG, including members of cytochrome P450 (CYP450) family and genes involved in fatty acid β-oxidation and ω-oxidation. For further identification of the CYP450s genes involved in the biosynthesis of MG secretions, we analyzed by means of qPCR, the expression levels of six of the CYP450 genes most abundantly expressed in the transcriptome analysis across different castes, ages, tasks and tissues. Our analysis revealed that CYP6AS8 and CYP6AS11, the most abundantly expressed CYP450 genes in worker and queen MGs, respectively, are selectively expressed in the MGs of workers and queens compared to other tissues. These results suggest that these genes might be responsible for the critical bifurcated hydroxylation process in the biosynthesis pathway. Our study contributes to the description of the molecular basis for the biosynthesis of fatty acid-derived pheromones in the MGs.

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“…This fatty acid was first isolated from queen bee jelly by Townsend & Lucas (1940); its structure has been elucidated by Barker, Foster, Hodgson & Lamb (1959) and by Barker, Foster, Jackman & Lamb (1959). It was inactive in doses of 10-100 ,ug of the sodium salt, but slightly potentiated irin contractions.…”

Section: Distribution In Various Parts Of the Brainmentioning

confidence: 99%

Investigation of an active lipid in aqueous extracts of rabbit brain, and of some further hydroxy‐acids

Ambache¹,

Reynolds²,

Whiting³

1963

The Journal of Physiology

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Biological Origin and Configuration of 10-Hydroxy-Δ2-decenoic Acid

Cited by 38 publications

References 8 publications

Histone deacetylase inhibitor activity in royal jelly might facilitate caste switching in bees

Histone deacetylase inhibitor activity in royal jelly might facilitate caste switching in bees

Comparative transcriptome analysis on the synthesis pathway of honey bee (Apis mellifera) mandibular gland secretions

Investigation of an active lipid in aqueous extracts of rabbit brain, and of some further hydroxy‐acids

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