Lithocholic acid
Chemical compound / From Wikipedia, the free encyclopedia
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.[citation needed]
Names | |
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IUPAC name
3α-Hydroxy-5β-cholan-24-oic acid | |
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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3D model (JSmol) |
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3217757 | |
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ECHA InfoCard | 100.006.455 |
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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).
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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 high affinity (20 μM) 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 was also shown to have anti-aging effects in a yeast study.[10][11] A later study showed that the bile acid accumulates in the inner and outer mitochondrial membranes, altering the mitochondria's lipid composition by promoting or inhibiting various enzymes.[12]