What is Myristoleic Acid?
Myristoleic acid is a tetradecenoic, long chain fatty acid found in natural compounds such as Serenoa repens (Saw palmetto) extract, nutmeg, butter, and milk1. Long-chain fatty acids support heart health and healthy blood pressure, cholesterol levels, and joints. Myristoleic acid can be synthesized from myristic acid–found in palm seed oil, coconut oil, and butter–by the enzyme stearoyl-CoA desaturase (SCD)-1 in various organisms, including humans. Additionally, myristoleic acid is a substrate for the cytochrome P450 enzyme CYP102D1, which mediates cell metabolism. Because it is an amphipathic acid, it may be able to integrate into cell membranes, creating structural defects and causing cell death at high concentrations2. Myristoleic acid levels in humans can also be modulated by the gut microbiome, and several studies have shown that microbes can produce or consume myristoleic acid.
Acide myristoléique et cancer
S. repens extracts have been historically used to treat prostatic hyperplasia and nonbacterial prostatitis, and myristoleic acid is the main cytotoxic component of this extract. In an in vitro model of prostate cancer, myristoleic acid causes cell death via both apoptosis and necrosis of LNCaP cells, a human prostatic carcinoma cell line3. These data suggest that myristoleic acid may be an attractive antitumor agent for prostate cancer. However, further studies are needed to examine the effects of myristoleic acid on primary tumors.
Acide myristoléique et troubles endocriniens
Long-term consumption of the ginseng root has been shown to have anti-obesity effects. Notably, ginseng promotes the growth of Enterococcus faecalis, a gut bacterial species that produces high levels of myristoleic acid and other long chain fatty acids. Among several fatty acids, myristoleic was shown to be the most effective at upregulating brown adipocyte oxygen consumption and beige fat formation in vitro and reducing mouse weight gain in vivo4. Downregulation of the enzyme Acyl- CoA thioesterase, which contributes to myristoleic acid biosynthesis by E. faecalis, reverses the protective effects of myristoleic acid against weight gain in mice, suggesting that it may be a promising therapeutic for the prevention of obesity.
Myristoleic acid may also play an important protective role against nonalcoholic fatty liver disease (NAFLD). High-fat/high-sucrose diet-fed mice supplemented with nobiletin, a naturally occurring polymethoxyflavone, had reduced signs of NAFLD along with increased Allobaculum and Lactobacillus in the gut and increased systemic levels of myristoleic acid5. When fed myristoleic acid, these mice displayed reduced body weight, total triglycerides, total cholesterol, and free cholesterol, and reversed hepatocyte ballooning or degeneration. These results suggest that myristoleic acid oral supplementation may be a viable treatment for NAFLD and other chronic liver diseases, such as nonalcoholic steatohepatitis.
L'acide myristoléique et la santé des os
L'administration d'acide myristoléique à des souris prévient de manière significative la perte osseuse, la formation et la différenciation des ostéoclastes. En outre, les ostéoclastes traités à l'acide myristoléique présentent une formation anormale d'anneaux d'actine et une forme anormale. Dans les ostéoclastes, l'acide myristoléique supprime l'activité kinase de Src en inhibant la myristolyation et bloque indirectement la phosphorylation de Pyk2. Cette relation peut être due à la capacité de l'acide myristoléique à inhiber la N-myristoyl-transférase, une enzyme essentielle qui contribue au réarrangement du cytosquelette des ostéoclastes. Ces résultats suggèrent que l'acide myristoléique pourrait être un nouveau candidat thérapeutique pour l'ostéoporose et d'autres troubles osseux6.
Acide myristoléique et troubles de la peau et des cheveux
Cutibacterium acnes colonizes the human skin and contributes to the pathogenesis of acne vulgaris. Although often resistant to antibiotics, biofilm formation by this bacterium has been effectively inhibited by myristoleic acid, which inhibits cell growth and bacterial excretion of extracellular polymeric substances and reduces cell hydrophobicity. Treatment of C. acnes bacteria with myristoleic acid upregulates several lipase genes, which are hypothesized to play a role in the conversion of myristoleic acid to a less toxic metabolite. Therefore, myristoleic acid may be useful for treating or preventing acne and C. acnes-associated diseases. However, further studies are needed to confirm its ability to inhibit C. acnes infection and acne development in vivo7.
Myristoleic acid is also important for the biosynthesis of the bacterial pyoverdine siderophore. Siderophores are virulence factors that drive iron sequestration by several bacteria species, including Pseudomonas aeruginosa, which can also play a role in acne development. Because the myristoleic acid residue is removed from the pyoverdine siderophore in P. aeruginosa prior to excretion, the toxic effects of myristoleic acid may be evident in extracellular bacterial space8.
Le traitement de modèles d'organes de flanc de hamster, composés de mélanocytes dermiques, de glandes sébacées et de follicules pileux, avec de l'acide myristoléique et d'autres acides gras apparentés inhibe la croissance sur le site d'application topique9. Cela suggère que l'acide myristoléique pourrait être utile en tant que traitement topique des troubles cutanés, tels que l'acné et l'alopécie androgénique.
La chute des cheveux est due à une perturbation du cycle de croissance des cheveux dans les cellules de la papille dermique, qui se trouvent à la base du follicule pileux. L'acide myristoléique peut protéger contre la chute des cheveux dans des troubles tels que l'alopécie grâce à sa capacité à activer la voie Wnt, qui favorise la prolifération des cellules de la papille dermique et la formation d'autophagosomes10.
Acide myristoléique et recherche
As of March 2024, there are 157 citations for myristoleic acid in research publications (excluding books and documents) on Pubmed. As researchers continue to unravel the pharmacological and physiological mechanisms of myristoleic acid, more research, both in vitro and in vivo, is required to assess its potential use for the treatment of various cancers as well as endocrine, skin, and bone disorders.
Références
- National Library of Medicine, National Center for Biotechnology Information. PubChem Compound Summary, Myristoleic acid (CID 5281119). https://pubchem.ncbi.nlm.nih.gov/compound/Myristoleic-acid
- Desbois AP et Smith VJ. Acides gras libres antibactériens : activités, mécanismes d'action et potentiel biotechnologique. Appl Microbiol Biotechnol. 2010;85(6):1629-1642. doi:10.1007/S00253-009-2355-3/FIGURES/3
- Iguchi K, Okumura N, Usui S, et al. L'acide myristoléique, un composant cytotoxique de l'extrait de Serenoa repens, induit l'apoptose et la nécrose dans les cellules prostatiques humaines LNCaP. Prostate. 2001;47(1):59-65. doi:10.1002/PROS.1047
- Quan LH, Zhang C, Dong M, et al. L'acide myristoléique produit par les entérocoques réduit l'obésité par l'activation du tissu adipeux brun. Gut. 2020;69(7):1239-1247. doi:10.1136/GUTJNL-2019-319114
- Li SZ, Zhang NN, Yang X, et al. Nobiletin Ameliorates Nonalcoholic Fatty Liver Disease by Regulating Gut Microbiota and Myristoleic Acid Metabolism (La nobiletine améliore la maladie du foie gras non alcoolique en régulant le microbiote intestinal et le métabolisme de l'acide myristoléique). J Agric Food Chem. 2023;71(19):7312-7323. doi:10.1021/ACS.JAFC.2C08637
- Kwon JO, Jin WJ, Kim B, Kim HH, Lee ZH. L'acide myristoléique inhibe la formation des ostéoclastes et la résorption osseuse en supprimant l'activation de Src et Pyk2 par le RANKL. Eur J Pharmacol. 2015;768:189-198. doi:10.1016/J.EJPHAR.2015.10.053
- Kim YG, Lee JH, Lee J. Antibiofilm activities of fatty acids including myristoleic acid against Cutibacterium acnes via reduced cell hydrophobicity. Phytomedicine. 2021;91. doi:10.1016/J.PHYMED.2021.153710
- Hannauer M, Schäfer M, Hoegy F, et al. La biosynthèse du sidérophore pyoverdine de Pseudomonas aeruginosa implique des précurseurs avec une chaîne d'acide myristique ou myristoléique. FEBS Lett. 2012;586(1):96-101. doi:10.1016/J.FEBSLET.2011.12.004
- Liao S, Lin J, Dang MT, et al. Growth suppression of hamster flank organs by topical application of catechins, alizarin, curcumin, and myristoleic acid. Arch Dermatol Res. 2001;293(4):200-205. doi:10.1007/S004030000203/METRICS
- Choi YK, Kang J il, Hyun JW, et al. Myristoleic Acid Promotes Anagen Signaling by Autophagy through Activating Wnt/β-Catenin and ERK Pathways in Dermal Papilla Cells (L'acide myristoléique favorise la signalisation de l'anagène par l'autophagie en activant les voies Wnt/β-Catenin et ERK dans les cellules de la papille dermique). Biomol Ther (Seoul). 2021;29(2):211-219. doi:10.4062/BIOMOLTHER.2020.169