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| Names | |
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| IUPAC name 3α-Hydroxy-5β-cholan-24-oic acid | |
| Systematic IUPAC name (4R)-4-phenanthren-1-yl]pentanoic acid | |
| Other names Lithocholate; Lithocolic acid; 3α-Hydroxy-5β-cholanic acid; 5β-Cholan-24-oic acid-3α-ol | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| Beilstein Reference | 3217757 |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.006.455 
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| EC Number |
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| IUPHAR/BPS | |
| KEGG | |
| PubChem CID | |
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| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
| Chemical formula | C24H40O3 |
| Molar mass | 376.581 g·mol |
| Melting point | 183 to 188 °C (361 to 370 °F; 456 to 461 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 N verify (what is ?)
Infobox references
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Lithocholic acid, also known as 3α-hydroxy-5β-cholan-24-oic acid or LCA, is a bile acid that acts as a detergent to solubilize fats for absorption. Bacterial action in the colon produces LCA from chenodeoxycholic acid by reduction of the hydroxyl functional group at carbon-7 in the "B" ring of the steroid framework.
It has been implicated in human and experimental animal carcinogenesis. Preliminary in vitro research suggests that LCA selectively kills neuroblastoma cells, while sparing normal neuronal cells and is cytotoxic to numerous other malignant cell types at physiologically relevant concentrations.
Dietary fiber can bind to lithocholic acid and aid in its excretion in stool; as such, fiber can protect against colon cancer.
LCA (and LCA acetate and LCA propionate) can activate the vitamin D receptor without raising calcium levels as much as vitamin D itself.
LCA binds with 20 μM affinity to the human membrane enzyme NAPE-PLD, enhancing dimer assembly and enabling catalysis. NAPE-PLD catalyzes the release of anandamide and other N-acylethanolamines (NAE) from the membrane precursor N-acylphosphatidylethanolamine (NAPE). NAPE-PLD facilitates crosstalk between bile acid signals and lipid amide signals.
LCA has been reported to have anti-aging effects in yeast, and more recently fruit flies, nematodes and mice.
References
- Lithocholic acid at Sigma-Aldrich
- Kozoni, V.; Tsioulias, G; Shiff, S; Rigas, B (2000). "The effect of lithocholic acid on proliferation and apoptosis during the early stages of colon carcinogenesis: Differential effect on apoptosis in the presence of a colon carcinogen". Carcinogenesis. 21 (5): 999–1005. doi:10.1093/carcin/21.5.999. PMID 10783324.
- Zeng H, Umar S, Rust B, Lazarova D, Bordonaro M. Secondary Bile Acids and Short Chain Fatty Acids in the Colon: A Focus on Colonic Microbiome, Cell Proliferation, Inflammation, and Cancer. Int J Mol Sci. 2019 Mar 11;20(5):1214. doi:10.3390/ijms20051214 PMID 30862015
- Goldberg, AA; Beach, A; Davies, GF; Harkness, TA; Leblanc, A; Titorenko, VI (2011). "Lithocholic bile acid selectively kills neuroblastoma cells, while sparing normal neuronal cells". Oncotarget. 2 (10): 761–82. doi:10.18632/oncotarget.338. PMC 3248158. PMID 21992775.
- Jenkins, DJ; Wolever, TM; Rao, AV; Hegele, RA; Mitchell, SJ; Ransom, TP; Boctor, DL; Spadafora, PJ; et al. (1993). "Effect on blood lipids of very high intakes of fiber in diets low in saturated fat and cholesterol". The New England Journal of Medicine. 329 (1): 21–6. doi:10.1056/NEJM199307013290104. PMID 8389421.
- Ishizawa, M.; Matsunawa, M.; Adachi, R.; Uno, S.; Ikeda, K.; Masuno, H.; Shimizu, M.; Iwasaki, K.-i.; et al. (2008). "Lithocholic acid derivatives act as selective vitamin D receptor modulators without inducing hypercalcemia". The Journal of Lipid Research. 49 (4): 763–772. doi:10.1194/jlr.M700293-JLR200. PMID 18180267.
- Magotti P, Bauer I, Igarashi M, Babagoli M, Marotta R, Piomelli D, Garau G (Dec 2014). "Structure of Human N-Acylphosphatidylethanolamine-Hydrolyzing Phospholipase D: Regulation of Fatty Acid Ethanolamide Biosynthesis by Bile Acids". Structure. 23 (3): 598–604. doi:10.1016/j.str.2014.12.018. PMC 4351732. PMID 25684574.
- Kostic M (2015). "Bile Acids as Enzyme Regulators". Chemistry & Biology. 22 (4): 427–428. doi:10.1016/j.chembiol.2015.04.007.
- Margheritis E, Castellani B, Magotti P, Peruzzi S, Romeo E, Natali F, Mostarda S, Gioiello A, Piomelli D, Garau G (Oct 2016). "Bile Acid Recognition by NAPE-PLD". ACS Chem Biol. 11 (10): 2908–2914. doi:10.1021/acschembio.6b00624. PMC 5074845. PMID 27571266.
- Goldberg, AA; Richard, VR; Kyryakov, P; Bourque, SD; Beach, A; Burstein, MT; Glebov, A; Koupaki, O; et al. (2010). "Chemical genetic screen identifies lithocholic acid as an anti-aging compound that extends yeast chronological life span in a TOR-independent manner, by modulating housekeeping longevity assurance processes". Aging. 2 (7): 393–414. doi:10.18632/aging.100168. PMC 2933888. PMID 20622262.
- Arlia-Ciommo, Anthony; Leonov, Anna; Mohammad, Karamat; Beach, Adam; Richard, Vincent R.; Bourque, Simon D.; Burstein, Michelle T.; Goldberg, Alexander A.; Kyryakov, Pavlo; Gomez-Perez, Alejandra; Koupaki, Olivia; Titorenko, Vladimir I. (2018). "Mechanisms through which lithocholic acid delays yeast chronological aging under caloric restriction conditions". Oncotarget. 9 (79): 34945–34971. doi:10.18632/oncotarget.26188. PMC 6201858. PMID 30405886.
- Beach, Adam; Richard, Vincent R.; Leonov, Anna; Burstein, Michelle T.; Bourque, Simon D.; Koupaki, Olivia; Juneau, Mylène; Feldman, Rachel; Iouk, Tatiana; Titorenko, Vladimir I. (2013). "Mitochondrial membrane lipidome defines yeast longevity". Aging. 5 (7): 551–574. doi:10.18632/aging.100578. PMC 3765583. PMID 23924582.
- Qu, Qi; Chen, Yan; Wang, Yu; Long, Shating; Wang, Weiche; Yang, Heng-Ye; Li, Mengqi; Tian, Xiao; Wei, Xiaoyan; Liu, Yan-Hui; Xu, Shengrong; Zhang, Cixiong; Zhu, Mingxia; Lam, Sin Man; Wu, Jianfeng (2024-12-18). "Lithocholic acid phenocopies anti-ageing effects of calorie restriction". Nature. doi:10.1038/s41586-024-08329-5. ISSN 0028-0836.