Chemistry:Lithocholic acid
From HandWiki
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| Names | |
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| IUPAC name
3α-Hydroxy-5β-cholan-24-oic acid
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| Systematic IUPAC name
(4R)-4-[(1R,3aS,3bR,5aR,7R,9aS,9bS,11aR)-7-Hydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid | |
| Other names
Lithocholate; Lithocolic acid; 3α-Hydroxy-5β-cholanic acid; 5β-Cholan-24-oic acid-3α-ol
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| Identifiers | |
3D model (JSmol)
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| 3217757 | |
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| ChEMBL | |
| ChemSpider | |
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| KEGG | |
PubChem CID
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| Properties | |
| C24H40O3 | |
| Molar mass | 376.581 g·mol−1 |
| 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 [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
It has been implicated in human and experimental animal carcinogenesis.[2][3] 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.[4]
Dietary fiber can bind to lithocholic acid and aid in its excretion in stool;[5] 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.[6]
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.[7][8][9]
LCA has been reported to have anti-aging effects in yeast,[10][11][12] and more recently fruit flies, nematodes, and mice.[13][14]
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 (Mar 2019). "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 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. 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.
- ↑ "Structure of Human N-Acylphosphatidylethanolamine-Hydrolyzing Phospholipase D: Regulation of Fatty Acid Ethanolamide Biosynthesis by Bile Acids". Structure 23 (3): 598–604. Dec 2014. doi:10.1016/j.str.2014.12.018. PMID 25684574.
- ↑ "Bile Acids as Enzyme Regulators". Chemistry & Biology 22 (4): 427–428. 2015. doi:10.1016/j.chembiol.2015.04.007.
- ↑ "Bile Acid Recognition by NAPE-PLD.". ACS Chem Biol 11 (10): 2908–2914. Oct 2016. doi:10.1021/acschembio.6b00624. 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. PMID 20622262.
- ↑ Arlia-Ciommo, Anthony; Leonov, Anna; Mohammad, Karamat; Beach, Adam; Richard, Vincent R.; Bourque, Simon D.; Burstein, Michelle T.; Goldberg, Alexander A. et al. (2018). "Mechanisms through which lithocholic acid delays yeast chronological aging under caloric restriction conditions". Oncotarget 9 (79): 34945–34971. doi:10.18632/oncotarget.26188. PMID 30405886.
- ↑ Beach, Adam; Richard, Vincent R.; Leonov, Anna; Burstein, Michelle T.; Bourque, Simon D.; Koupaki, Olivia; Juneau, Mylène; Feldman, Rachel et al. (2013). "Mitochondrial membrane lipidome defines yeast longevity". Aging 5 (7): 551–574. doi:10.18632/aging.100578. PMID 23924582.
- ↑ Ledford, Heidi (2024). "Why eating less slows ageing: this molecule is key". Nature News. doi:10.1038/d41586-024-04220-5. https://www.nature.com/articles/d41586-024-04220-5.
- ↑ Qu, Qi; Chen, Yan; Wang, Yu; Long, Shating; Wang, Weiche; Yang, Heng-Ye; Li, Mengqi; Tian, Xiao et al. (2024-12-18). "Lithocholic acid phenocopies anti-ageing effects of calorie restriction" (in en). Nature 643 (8070): 192–200. doi:10.1038/s41586-024-08329-5. ISSN 0028-0836. PMID 39695227.
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