10-Hydroxy-2-decenoic acid

10-HDA is an unsaturated fatty acid found in royal jelly produced from the hypopharyngeal and mandibular gland secretions of honeybees. 10-HDA has longevity-promoting effects in C. elegans at a concentration of 25 μM. It down-regulates matrix metalloproteinases (MMPs) in rheumatoid arthritis synovial fibroblasts at a concentration of 1.25 nM and inhibits VEGF-induced angiogenesis in HUVECs at 500 μM. 10-HDA also facilitates differentiation of neurons from neural stem/progenitor cells and promotes collagen production by skin fibroblasts at concentrations of 100 μM and 1.5 mM, respectively.

10-Hydroxy-2-decenoic acid has antiseptic, anti-inflammatory, anti-obesity, anti-aging, preventing bone loss and anti-tumour pharmacological effects, with potential therapeutic effects for postmenopausal osteoporosis, as well as benefiting the human gastrointestinal tract^[1-3].

ChEBI: (E)-10-hydroxydec-2-enoic acid is an omega-hydroxy amino acid that is 2-decenoic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group and in which the C=C double bond has E configuration. It is a component of royal jelly. It has a role as an animal metabolite and a geroprotector. It is an alpha,beta-unsaturated monocarboxylic acid, a straight-chain fatty acid, a hydroxy monounsaturated fatty acid and an omega-hydroxy-medium-chain fatty acid.

[1] Li, Y., Wang, J., Wang, F., Wang, L., Wang, L., Xu, Z., Yuan, H., Yang, X., Li, P., Su, J., & Wang, R. (2021). Production of 10‐Hydroxy‐2‐decenoic Acid from Decanoic Acid via Whole‐Cell Catalysis in Engineered Escherichia coli. ChemSusChem, 15(9). https://doi.org/10.1002/cssc.202102152
[2] He, D., Chen, Y., Shen, J., Yu, H., Keasling, J. D., & Luo, X. (2025). Biosynthesis of 10-Hydroxy-2-Decenoic Acid in Escherichia coli. Metabolic Engineering, 88, 240–249. https://doi.org/10.1016/j.ymben.2025.01.006
[3] Fang, K., Xu, Z., Yang, L., Cui, Q., Du, B., Liu, H., Wang, R., Li, P., Su, J., & Wang, J. (2024). Biosynthesis of 10-Hydroxy-2-decenoic Acid through a One-Step Whole-Cell Catalysis. Journal of Agricultural and Food Chemistry, 72(2), 1190–1202. https://doi.org/10.1021/acs.jafc.3c08142
[4] Yuan, C.-Y., Yang, S.-Z., Gao, C.-M., Bai, T.-M., Han, T.-T., Jiang, S.-S., Liu, S.-L., Gao, K.-K., Mao, X.-Y., Jiang, H., & Li, Y. (2024). Biologically synthesized 10-Hydroxy-2-Decenoic acid activates cornified envelope formation via PPARα signaling, and regulates oxidative respiratory chain to improve mitochondrial function. Journal of Functional Foods, 122, Article 106505. https://doi.org/10.1016/j.jff.2024.106505

10-Hydroxy-2-decenoic acid is an orally available royal jelly component that potently inhibits osteoclastogenesis. It binds to free fatty acid receptor 4 (FFAR4) on osteoclasts which inhibits RANKL (receptor activator of nuclear factor-κB (NF-κB) ligand), thereby attenuating the induction of nuclear factor of activated T cells (NFAT) c1. 10-Hydroxy-2-decenoic acid inhibits bone resorption in ovariectomized mice.
The production of pro-inflammatory cytokines, Interleukin (IL)-8, IL-1β and tumor necrosis factor-alpha (TNF-α) in WiDr cells was modulated by 10-HDA. IL-8 were dramatically declined by 10-HDA at 3 mM, while IL-1β and TNF-α were significantly decreased. 10-HDA increased IL-1ra in a dose manner. NF-κB pathway is primarily in response to prototypical pro-inflammatory cytokines, and NF-κB was reduced after 10-HDA treatment. 10-HDA acted as potent bactericide against animal- or human-specific pathogens, including Staphylococcus aureus, Streptococcus alactolyticus, Staphylococcus intermedius B, Staphylococcus xylosus, Salmonella cholearasuis, Vibro parahaemolyticus and Escherichia coli (hemolytic)^[1].

10-Hydroxy-2-decenoic acid (10-HDA) is synthesized via whole-cell catalysis in engineered Escherichia coli or Saccharomyces cerevisiae, using decanoic acid or trans-2-decenoic acid as substrates through pathways involving P450 terminal hydroxylases and thioesterases such as UaFatB1[1][2][3][4].

[1] YUAN-CHANG YANG. 10-hydroxy-2-decenoic acid of royal jelly exhibits bactericide and anti-inflammatory activity in human colon cancer cells.[J]. BMC Complementary and Alternative Medicine, 2018: 202. DOI:10.1186/s12906-018-2267-9.
[2] YOKO HONDA. 10-Hydroxy-2-decenoic Acid, the Major Lipid Component of Royal Jelly, Extends the Lifespan of Caenorhabditis elegans through Dietary Restriction and Target of Rapamycin Signaling.[J]. Journal of Aging Research, 2015, 2015: 425261. DOI:10.1155/2015/425261.
[3] YOSUKE TSUCHIYA. The key royal jelly component 10-hydroxy-2-decenoic acid protects against bone loss by inhibiting NF-κB signaling downstream of FFAR4.[J]. The Journal of Biological Chemistry, 2020, 295 34: 12224-12232. DOI:10.1074/jbc.RA120.013821.