10-hydroxy decanoic acid, trans-10-hydroxy-2-decanoic acid, and sebacic acid: Source, metabolism, and potential health functionalities and nutraceutical applications.
10‐hydroxydecanoic acid
health functionalities
royal jelly
sebacic acid
trans‐10‐hydroxy‐2‐decanoic acid
Journal
Journal of food science
ISSN: 1750-3841
Titre abrégé: J Food Sci
Pays: United States
ID NLM: 0014052
Informations de publication
Date de publication:
12 Jun 2024
12 Jun 2024
Historique:
revised:
20
04
2024
received:
19
02
2024
accepted:
13
05
2024
medline:
12
6
2024
pubmed:
12
6
2024
entrez:
12
6
2024
Statut:
aheadofprint
Résumé
The popularity of royal jelly (RJ) as a functional food has attracted attention from various industries, especially nutraceuticals, due to the increasing demand from health enthusiasts. Sebacic acid, 10-hydroxy decanoic acid, and trans-10-hydroxy-2-decanoic acid are the primary medium-chain fatty acids (MCFAs) within RJ responsible for their health benefits. This review aims to consolidate information on these MCFAs' metabolic relationship and health functionalities in nutraceutical applications. We also investigated the natural characteristics mediated by these MCFAs and their metabolism in organisms. Finally, the production of these MCFAs using conventional (from castor oil) and alternative (from RJ) pathways was also discussed. This review can be a reference for using them as functional ingredients in nutraceutical industries.
Identifiants
pubmed: 38865248
doi: 10.1111/1750-3841.17143
doi:
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Informations de copyright
© 2024 Institute of Food Technologists.
Références
Ali, A. M., & Hendawy, A. O. (2019). Royal jelly acid, 10‐hydroxy‐trans‐2‐decenoic acid, for psychiatric and neurological disorders: How helpful could it be. Edelweiss Journal of Food Science and Technology, 1(1), 1–4. https://doi.org/10.33805/2765‐8821.101
Ali, A. M., & Kunugi, H. (2021). The effects of royal jelly acid, 10‐hydroxy‐trans‐2‐decenoic acid, on neuroinflammation and oxidative stress in astrocytes stimulated with lipopolysaccharide and hydrogen peroxide. Immuno, 1(3), 212–222. https://doi.org/10.3390/immuno1030013
Alkhaibari, A. M., & Alanazi, A. D. (2022). Insecticidal, antimalarial, and antileishmanial effects of royal jelly and its three main fatty acids, trans‐10‐hydroxy‐2‐decenoic acid, 10‐hydroxydecanoic acid, and sebacic acid. Evidence‐Based Complementary and Alternative Medicine, 2022, 7425322. https://doi.org/10.1155/2022/7425322
Althobaiti, N. (2022). Therapeutic potential of royal jelly to control Toxoplasma gondii infection in mice. Tropical Biomedicine, 39(2), 295–301. https://doi.org/10.47665/tb.39.2.020
Alvarez, S., Contreras‐Kallens, P., Aguayo, S., Ramirez, O., Vallejos, C., Ruiz, J., Carrasco‐Gallardo, E., Troncoso‐Vera, S., Morales, B., & Schuh, C. M. A. P. (2022). Extracellular vesicles derived from Apis mellifera royal jelly promote wound healing by modulating inflammation and cellular responses. BioRxiv, 2022(7), 21.501009. https://doi.org/10.1101/2022.07.21.501009
Arruebo, M., & Sebastian, V. (2020). Batch and microfluidic reactors in the synthesis of enteric drug carriers. In Nanotechnology for Oral Drug Delivery, 317–357. https://doi.org/10.1016/B978‐0‐12‐818038‐9.00008‐9
Balkanska, R., Marghitas, L. A., & Pavel, C. I. (2017). Antioxidant activity and total polyphenol content of royal jelly from Bulgaria. International Journal of Current Microbiology and Applied Sciences, 6(10), 578–585. https://doi.org/10.20546/ijcmas.2017.610.071
Bharathi, S. S., Zhang, Y., Gong, Z., Muzumdar, R., & Goetzman, E. S. (2020). Role of mitochondrial acyl‐CoA dehydrogenases in the metabolism of dicarboxylic fatty acids. Biochemical and Biophysical Research Communications, 527(1), 162–166. https://doi.org/10.1016/j.bbrc.2020.04.105
Bianco, O. (2022). Measuring the effect of royal jelly on the seasonal responses and metabolic profile of Culex pipiens [Doctoral Dissertation]. The Ohio State University. https://kb.osu.edu/handle/1811/101321
Bülow, M. H., Wingen, C., Senyilmaz, D., Gosejacob, D., Sociale, M., Bauer, R., Schulze, H., Sandhoff, K., Teleman, A. A., Hoch, M., & Sellin, J. (2018). Unbalanced lipolysis results in lipotoxicity and mitochondrial damage in peroxisome‐deficient Pex19 mutants. Molecular Biology of the Cell, 29(4), 396–407. https://doi.org/10.1091/mbc.E17‐08‐0535
Chen, Y. F., Wang, K., Zhang, Y. Z., Zheng, Y. F., & Hu, F. L. (2016). In vitro anti‐inflammatory effects of three fatty acids from royal jelly. Mediators of Inflammation, 2016, 3583684. https://doi.org/10.1155/2016/3583684
Chen, Y. L., Xie, J., Chen, J. Q., Zhu, Y., Chen, R., & Qu, H. L. (2019). Effect of aerobic exercise combined with black fruit wolfberry pigment supplementation on hepatic fatty acid oxidation in mice with non‐alcoholic fatty liver disease. Chinese Journal of Sports Medicine, 3, 201–210. https://doi.org/10.3969/j.issn.1000‐6710.2019.03.006
Cheng, Z., Zheng, L., & Almeida, F. A. (2018). Epigenetic reprogramming in metabolic disorders: Nutritional factors and beyond. The Journal of Nutritional Biochemistry, 54, 1–10. https://doi.org/10.1016/j.jnutbio.2017.10.004
Cornara, L., Biagi, M., Xiao, J., & Burlando, B. (2017). Therapeutic properties of bioactive compounds from different honeybee products. Frontiers in Pharmacology, 8, 412. https://doi.org/10.3389/fphar.2017.00412
El‐Guendouz, S., Machado, A. M., Aazza, S., Lyoussi, B., Miguel, M. G., Mateus, M. C., & Figueiredo, A. C. (2020). Chemical characterization and biological properties of royal jelly samples from the Mediterranean area. Natural Product Communications, 15(2), 1934578×20908080. https://doi.org/10.1177/1934578X20908080
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
Feng, Q., Han, T., Xu, B. Y., He, B., Li, Z. H., & Zhang, X. L. (2017). A new method for the synthesis of E‐10‐hydroxy‐2‐decenoic acid. Synthetic Chemistry, 25(3), 245–249. https://doi.org/10.15952/j.cnki.cjsc.1005‐1511.2017.03.16202
Filipič, B., Gradišnik, L., Rihar, K., Pereyra, A., Đermić, D., & Mazija, H. (2019). Royal jelly and human interferon‐alpha (HuIFN‐αN3) affect proliferation, glutathione level, and lipid peroxidation in human colorectal adenocarcinoma cells in vitro. In Lipid peroxidation research (pp. 65–100). IntechOpen. https://doi.org/10.5772/intechopen.85777
Geng, J. W., Yu, A. H., Mi, X. T., & Zhou, G. T. (2010). Study on the extraction process of 10‐HDA from royal jelly. Brewing in China, 29(9), 86–89. https://doi.org/10.3969/j.issn.0254‐5071.2010.09.027
Gregson, B. H., Metodieva, G., Metodiev, M. V., & McKew, B. A. (2019). Differential protein expression during growth on linear versus branched alkanes in the obligate marine hydrocarbon‐degrading bacterium Alcanivorax borkumensis SK2T. Environmental Microbiology, 21(7), 2347–2359. https://doi.org/10.1111/1462‐2920.14620
Hagman, S., Mäkinen, A., Ylä‐Outinen, L., Huhtala, H., Elovaara, I., & Narkilahti, S. (2019). Effects of inflammatory cytokines IFN‐γ, TNF‐α and IL‐6 on the viability and functionality of human pluripotent stem cell‐derived neural cells. Journal of Neuroimmunology, 331, 36–45. https://doi.org/10.1016/j.jneuroim.2018.07.010
Hall, J. R., Rouillard, K. R., Suchyta, D. J., Brown, M. D., Ahonen, M. J. R., & Schoenfisch, M. H. (2019). Mode of nitric oxide delivery affects antibacterial action. ACS Biomaterials Science and Engineering, 6(1), 433–441. https://doi.org/10.1021/acsbiomaterials.9b01384
Hanai, R., Matsushita, H., Minami, A., Abe, Y., Tachibana, R., Watanabe, K., Takeuchi, H., & Wakatsuki, A. (2023). Effects of 10‐hydroxy‐2‐decenoic acid and 10‐hydroxydecanoic acid in royal jelly on bone metabolism in ovariectomized rats: A pilot study. Journal of Clinical Medicine, 12(16), 5309. https://doi.org/10.3390/jcm12165309
Hang, X., Quan, Z., & Jinfu, W. (2013). Treatment of sebacic acid industrial wastewater by extraction process using castor oil acid as extractant. Chinese Journal of Chemical Engineering, 21(9), 967–973. https://doi.org/10.1016/S1004‐9541(13)60546‐7
Hata, T., Furusawa‐Horie, T., Arai, Y., Takahashi, T., Seishima, M., & Ichihara, K. (2020). Studies of royal jelly and associated cross‐reactive allergens in atopic dermatitis patients. PLoS ONE, 15(6), e0233707. https://doi.org/10.1371/journal.pone.0233707
Hattori, N., Nomoto, H., Fukumitsu, H., Mishima, S., & Furukawa, S. (2007). Royal jelly and its unique fatty acid, 10‐hydroxy‐trans‐2‐decenoic acid, promote neurogenesis by neural stem/progenitor cells in vitro. Biomedical Research, 28(5), 261–266. https://doi.org/10.2220/biomedres.28.261
Huang, C. H., Lee, W. J., Huang, Y. L., Tsai, T. F., Chen, L. K., & Lin, C. H. (2023). Sebacic acid as a potential age‐related biomarker of liver aging: Evidence linking mice and human. The Journals of Gerontology: Series A, 78(10), 1799–1808. https://doi.org/10.1093/gerona/glad121
Group, C. W. (2016). Novel continuous reactor for production of sebacic acid from castor oil. Chemical Weekly, 61(43), 198–199.
Iaconelli, A., Gastaldelli, A., Chiellini, C., Gniuli, D., Favuzzi, A., Binnert, C., Mace, K., & Mingrone, G. (2010). Effect of oral sebacic acid on postprandial glycemia, insulinemia, and glucose rate of appearance in type 2 diabetes. Diabetes Care, 33(11), 2327–2332. https://doi.org/10.2337/dc10‐0663
Ibrahim, S. E. M., & Kosba, A. A. (2018). Royal jelly supplementation reduces skeletal muscle lipotoxicity and insulin resistance in aged obese rats. Pathophysiology, 25(4), 307–315. https://doi.org/10.1016/j.pathophys.2018.05.001
Inoue, Y., Ienaga, M., Kamiya, T., Adachi, T., Ohta, M., & Hara, H. (2022). Royal jelly fatty acids downregulate ANGPTL8 expression through the decrease in HNF4α protein in human hepatoma HepG2 cells. Bioscience, Biotechnology, and Biochemistry, 86(6), 747–754. https://doi.org/10.1093/bbb/zbac043
Isidorow, W., Witkowski, S., Iwaniuk, P., Zambrzycka, M., & Swiecicka, I. (2018). Royal jelly aliphatic acids contribute to antimicrobial activity of honey. Journal of Apicultural Science, 62(1), 111–123. https://doi.org/10.2478/jas‐2018‐0012
Ito, S., Hakamada, T., Ogino, T., & Osanai, T. (2021). Reconstitution of oxaloacetate metabolism in the tricarboxylic acid cycle in Synechocystis sp. PCC 6803: Discovery of important factors that directly affect the conversion of oxaloacetate. The Plant Journal, 105(6), 1449–1458. https://doi.org/10.1111/tpj.15120
Jeon, W. Y., Jang, M. J., Park, G. Y., Lee, H. J., Seo, S. H., Lee, H. S., Han, C., Kwon, H., Lee, H. C., Lee, J. H., Hwang, Y. T., Lee, M. O., Lee, J. G., Lee, H. W., & Ahn, J. O. (2019). Microbial production of sebacic acid from a renewable source: production, purification, and polymerization. Green Chemistry, 21(23), 6491–6501. https://doi.org/10.1039/C9GC02274K
Kobayashi, G., Okamura, T., Majima, S., Senmaru, T., Okada, H., Ushigome, E., Nakanishi, N., Nishimoto, Y., Yamada, T., Okamoto, H., Okumura, N., Sasano, R., Hamaguchi, M., & Fukui, M. (2023). Effects of royal jelly on gut dysbiosis and NAFLD in db/db mice. Nutrients, 15(11), 2580. https://doi.org/10.3390/nu15112580
Kokotou, M. G., Mantzourani, C., Babaiti, R., & Kokotos, G. (2020). Study of the royal jelly free fatty acids by liquid chromatography‐high resolution mass spectrometry (LC‐HRMS). Metabolites, 10(1), 40. https://doi.org/10.3390/metabo10010040
Kunugi, H., & Mohammed Ali, A. (2019). Royal jelly and its components promote healthy aging and longevity: From animal models to humans. International Journal of Molecular Sciences, 20(19), 4662. https://doi.org/10.3390/ijms20194662
Li, Q., Gu, K., & Cheng, X. H. (2007). Synthesis of royal jelly acid. The World of Chemistry, 48(5), 4. https://doi.org/10.3969/j.issn.0367‐6358.2007.05.011
Li, Y., & Huang, L. (2011). Microwave‐catalyzed rapid synthesis of 10‐acetoxydecanoic acid. Anhui Agricultural Science, 39(34), 21352.
Li, Y., Wang, J., Wang, F., Wang, L., Wang, L., Xu, Z., Yuan, H., Yang, X., Li, P., Su, J., & Su, J. (2022). Production of 10‐hydroxy‐2‐decenoic acid from decanoic acid via whole‐cell catalysis in engineered Escherichia coli. ChemSusChem, 15(9), e202102152. https://doi.org/10.1002/cssc.202102152
Liu, L., Zhao, J., Zhang, R., Wang, X., Wang, Y., Chen, Y., & Feng, R. (2021). Serum untargeted metabolomics delineates the metabolic status in different subtypes of non‐alcoholic fatty liver disease. Journal of Pharmaceutical and Biomedical Analysis, 200, 114058. https://doi.org/10.1016/j.jpba.2021.114058
Liu, S. J., Chen, L., Zhang, R., Wu, B., Chen, H. L., Zhang, X. Y., Fei, X. Q., & Yang, G. J. (2015). Determination of fatty acids in royal jelly by high performance liquid chromatography‐mass spectrometry. Journal of Yangzhou University: Natural Science Edition, 18(2), 5. https://doi.org/10.19411/j.1007‐824x.2015.02.011
Liu, X., Yu, J., Zhao, J., Guo, J., Zhang, M., & Liu, L. (2020). Glucose challenge metabolomics implicates the change of organic acid profiles in hyperlipidemic subjects. Biomedical Chromatography, 34(6), e4815. https://doi.org/10.1002/bmc.4815
Makino, J., Ogasawara, R., Kamiya, T., Hara, H., Mitsugi, Y., Yamaguchi, E., Itoh, A., & Adachi, T. (2016). Royal jelly constituents increase the expression of extracellular superoxide dismutase through histone acetylation in monocytic THP‐1 cells. Journal of Natural Products, 79(4), 1137–1143. https://doi.org/10.1021/acs.jnatprod.6b00037
Malaisse, W. J., Greco, A. V., & Mingrone, G. (2000a). Oxidation of [1, 12–14C] dodecanedioic acid by rat pancreatic islets. International Journal of Molecular Medicine, 6(4), 453–457. https://doi.org/10.3892/ijmm.6.4.453
Malaisse, W. J., Greco, A. V., & Mingrone, G. (2000b). Effects of aliphatic dioic acids and glycerol‐1, 2, 3‐tris (dodecanedioate) on d‐glucose‐stimulated insulin release in rat pancreatic islets. British Journal of Nutrition, 84(5), 733–736. https://doi.org/10.1017/S0007114500002099
Minegaki, N., Koshizuka, T., Nishina, S., Kondo, H., Takahashi, K., Sugiyama, T., & Inoue, N. (2020). The carboxyl‐terminal penta‐peptide repeats of major royal jelly protein 3 enhance cell proliferation. Biological and Pharmaceutical Bulletin, 43(12), 1911–1916. https://doi.org/10.1248/bpb.b20‐00607
Mingrone, G., & Metz, C. (2009). Medium‐chain dicarboxylic acids, their derivatives and metabolic disorders. C.N. Patent No. 105456242A. Beijing, China. State Intellectual Property Office of the People's Republic of China.
Mishima, S., Suzuki, K. M., Isohama, Y., Kuratsu, N., Araki, Y., Inoue, M., & Miyata, T. (2005). Royal jelly has estrogenic effects in vitro and in vivo. Journal of Ethnopharmacology, 101(1–3), 215–220. https://doi.org/10.1016/j.jep.2005.04.012
Mohamed, A. A. R., Galal, A. A., & Elewa, Y. H. (2015). Comparative protective effects of royal jelly and cod liver oil against neurotoxic impact of tartrazine on male rat pups brain. Acta Histochemica, 117(7), 649–658. https://doi.org/10.1016/j.acthis.2015.07.002
Moţ, D. (2015). In vitro study of honey antimicrobial activity. Scientific Papers: Animal Science and Biotechnologies, 48, 262–267.
Moutsatsou, P., Papoutsi, Z., Kassi, E., Heldring, N., Zhao, C., Tsiapara, A., Melliou, E., Chrousos, G. P., Chinou, I., & Karshikoff, A. (2010). Fatty acids derived from royal jelly are modulators of estrogen receptor functions. PLoS ONE, 5(12), e15594. https://doi.org/10.1371/journal.pone.0015594
Nabas, Z., Haddadin, M. S., Haddadin, J., & Nazer, I. K. (2014). Chemical composition of royal jelly and effects of synbiotic with two different locally isolated probiotic strains on antioxidant activities. Polish Journal of Food and Nutrition Sciences, 64(3), 171–180. https://doi.org/10.2478/pjfns‐2013‐0015
Niu, J. H., Yuan, J., Zhang, H. F., Jia, J. Y., Han, X., Wu, M. Y., Zhang, M., & Zhao, W. (2020). Protective effect of royal jelly acid on alcoholic liver injury in mice. Food Industry Technology, 41(3), 6. https://doi.org/10.13386/j.issn1002‐0306.2020.03.048
Ranea‐Robles, P., Violante, S., Argmann, C., Dodatko, T., Bhattacharya, D., Chen, H., Yu, C., Friedman, S. L., Puchowicz, M., & Houten, S. M. (2021). Murine deficiency of peroxisomal L‐bifunctional protein (EHHADH) causes medium‐chain 3‐hydroxydicarboxylic aciduria and perturbs hepatic cholesterol homeostasis. Cellular and Molecular Life Sciences, 78(14), 5631–5646. https://doi.org/10.1007/s00018‐021‐03869‐9
Sang, P. P., Li, J., Tan, X. D., Peng, W., Zhou, H. H., Tian, Y. P., & Zhang, M. L. (2023). Associations between Borg's rating of perceived exertion and changes in urinary organic acid metabolites after outdoor weight‐bearing hiking. World Journal of Psychiatry, 13(5), 234. https://doi.org/10.5498/wjp.v13.i5.234
Shahla, J., Dariush, H., Bijan, S. M., Majid, E., Zahra, A., & Bahman, Y. (2021). Comparative immunomodulatory effects of jelly royal and 10‐H2DA on experimental autoimmune encephalomyelitis. Gene Reports, 24, 101217. https://doi.org/10.1016/j.genrep.2021.101217
Shirakawa, T., Miyawaki, A., Matsubara, T., Okumura, N., & Kokabu, S. (2020). Daily oral administration of protease‐treated royal jelly protects against denervation‐induced skeletal muscle atrophy. Nutrients, 12(10), 3089. https://doi.org/10.3390/nu12103089
Spannhoff, A., Kim, Y. K., Raynal, N. J. M., Gharibyan, V., Su, M. B., Zhou, Y. Y., Li, J., Castellano, S., Sbardella, G., & Issa, J. P. J. (2011). Histone deacetylase inhibitor activity in royal jelly might facilitate caste switching in bees. EMBO Reports, 12(3), 238–243. https://doi.org/10.1101/415364
Sun, S. H. (2019). Cloning of key enzyme molecules for biosynthesis of 10‐HDA and construction of engineering bacteria [Master's Thesis]. Qilu University of Technology.
Suzuki, K. M., Isohama, Y., Maruyama, H., Yamada, Y., Narita, Y., Ohta, S., Araki, Y., Miyata, T., & Mishima, S. (2008). Estrogenic activities of fatty acids and a sterol isolated from royal jelly. Evidence‐Based Complementary and Alternative Medicine, 5, 295–302. https://doi.org/10.1093/ecam/nem036
Takahashi, K., Sugiyama, T., Tokoro, S., Neri, P., & Mori, H. (2012). Inhibition of interferon‐γ‐induced nitric oxide production by 10‐hydroxy‐trans‐2‐decenoic acid through inhibition of interferon regulatory factor‐8 induction. Cellular Immunology, 273(1), 73–78. https://doi.org/10.1016/j.cellimm.2011.11.004
Tataranni, P. A., Mingrone, G., Gaetano, A. D., Raguso, C., & Greco, A. V. (1992). Tracer study of metabolism and tissue distribution of sebacic acid in rats. Annals of Nutrition and Metabolism, 35(5–6), 296–303. https://doi.org/10.1159/000177733
Terada, Y., Narukawa, M., & Watanabe, T. (2011). Specific hydroxy fatty acids in royal jelly activate TRPA1. Journal of Agricultural and Food Chemistry, 59(6), 2627–2635. https://doi.org/10.1021/jf1041646
Tian, W., Li, M., Guo, H., Peng, W., Xue, X., Hu, Y., Liu, Y., Zhao, Y., Fang, X., Wang, K., Li, X., Tong, Y., Conlon, M. A., Wu, W., Ren, F., & Chen, Z. (2018). Architecture of the native major royal jelly protein 1 oligomer. Nature Communications, 9(1), 3373. https://doi.org/10.1038/s41467‐018‐05619‐1
Townsend, G. F., Brown, W. H., Felauer, E. E., & Hazlett, B. (1961). Studies on the in vitro antitumor activity of fatty acids: IV. The esters of acids closely related to 10‐hydroxy‐2‐decenoic acid from royal jelly against transplantable mouse leukemia. Canadian Journal of Biochemistry and Physiology, 39(11), 1765–1770. https://doi.org/10.1139/o61‐195
Tsuchiya, Y., Hayashi, M., Nagamatsu, K., Ono, T., Kamakura, M., Iwata, T., & Nagamatsu, K. (2020). The key royal jelly component 10‐hydroxy‐2‐decenoic acid protects against bone loss by inhibiting NF‐κB signaling downstream of FFAR4. Journal of Biological Chemistry, 295(34), 12224–12232. https://doi.org/10.1074/jbc.RA120.013821
Uthaibutra, V., Kaewkod, T., Prapawilai, P., Pandith, H., & Tragoolpua, Y. (2023). Inhibition of skin pathogenic bacteria, antioxidant and anti‐inflammatory activity of royal jelly from Northern Thailand. Molecules (Basel, Switzerland), 28(3), 996. https://doi.org/10.3390/molecules28030996
Vieira, J., de Paula Freitas, F. C., Cristino, A. S., Pinheiro, D. G., Aguiar, L. R., Framartino Bezerra Laure, M. A., Rosatto Moda, L. M., Paulino Simões, Z. L., & Barchuk, A. R. (2021). Molecular underpinnings of the early brain developmental response to differential feeding in the honey bee. Apis mellifera. Biochimica et Biophysica Acta (BBA)‐Gene Regulatory Mechanisms, 1864(9), 194732. https://doi.org/10.1016/j.bbagrm.2021.194732
Weiser, M. J., Grimshaw, V., Wynalda, K. M., Mohajeri, M. H., & Butt, C. M. (2017). Long‐term administration of queen bee acid (QBA) to rodents reduces anxiety‐like behavior, promotes neuronal health and improves body composition. Nutrients, 10(1), 13. https://doi.org/10.3390/nu10010013
Xu, X., Sun, L. P., & Dong, J. (2009). Study of the fatty acid composition of lipids in royal jelly. Food Science, 30(14), 213–214. https://doi.org/10.3321/j.issn:1002‐6630.2009.14.044
Yamaga, M., Tani, H., Yamaki, A., Tatefuji, T., & Hashimoto, K. (2019). Metabolism and pharmacokinetics of medium chain fatty acids after oral administration of royal jelly to healthy subjects. RSC Advances, 9(27), 15392–15401. https://doi.org/10.1039/C9RA02991E
Yang, X. Y., Yang, D. S., Wang, J. M., Li, C. Y., Lei, K. F., Chen, X. F., Shen, N. H., Jin, L. Q., & Wang, J. G. (2010). 10‐Hydroxy‐2‐decenoic acid from royal jelly: A potential medicine for RA. Journal of Ethnopharmacology, 128(2), 314–321. https://doi.org/10.1016/j.jep.2010.01.055
You, M., Miao, Z., Sienkiewicz, O., Jiang, X., Zhao, X., & Hu, F. (2020). 10‐hydroxydecanoic acid inhibits LPS‐induced inflammation by targeting p53 in microglial cells. International Immunopharmacology, 84, 106501. https://doi.org/10.1016/j.intimp.2020.106501
You, M., Wang, K., Pan, Y., Tao, L., Ma, Q., Zhang, G., & Hu, F. (2022). Combined royal jelly 10‐hydroxydecanoic acid and aspirin has a synergistic effect against memory deficit and neuroinflammation. Food and Function, 13(4), 2336–2353. https://doi.org/10.1039/D1FO02397G
Yu, S., Cui, J., Zhong, C., Meng, J., & Xue, T. (2019). Green process without thinning agents for preparing sebacic acid via solid‐phase cleavage. ACS Omega, 4(4), 6697–6702. https://doi.org/10.1021/acsomega.9b00577
Zhang, G. M., & Gao, H. (2008). Study on the green synthesis process of 10‐hydroxydecanoic acid. Guangdong Chemical, 35(9), 4. https://doi.org/10.3969/j.issn.1007‐1865.2008.09.018
Zhang, X., Lu, X., Zhou, Y., Guo, X., & Chang, Y. (2021). Major royal jelly proteins prevents NAFLD by improving mitochondrial function and lipid accumulation through activating the AMPK/SIRT3 pathway in vitro. Journal of Food Science, 86(3), 1105–1113. https://doi.org/10.1111/1750‐3841.15625