Lithocholic acid
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| Names | |
|---|---|
| IUPAC name
(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid | |
| Other names
Lithocholate; Lithocolic acid; 3α-Hydroxy-5β-cholan-24-oic acid; 3α-Hydroxy-5β-cholanic acid; 5β-Cholan-24-oic acid-3α-ol | |
| Identifiers | |
434-13-9  | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:16325  |
| ChEMBL | ChEMBL1478 |
| ChemSpider | 9519 |
| ECHA InfoCard | 100.006.455 |
| EC Number | 207-099-1 |
| 611 | |
| PubChem | 9903 |
| RTECS number | FZ2275000 |
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| Properties | |
| C24H40O3 | |
| Molar mass | 376.57 g/mol |
| Melting point | 183 to 188 °C (361 to 370 °F; 456 to 461 K) |
| Hazards | |
| S-phrases | S22 S24/25 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
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.[2] 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.[3]
Dietary fiber can bind to lithocholic acid and aid in its excretion in stool;[4] 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.[5]
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.
- ↑ 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.
Further reading
- 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. PMC 2933888. PMID 20622262.