3α-Hydroxy-7-oxo-5β-cholanic acid is a bile acid derivative, specifically an oxidized metabolite of chenodeoxycholic acid (CDCA), a primary bile acid synthesized in the liver from cholesterol.
🔬 Chemical Identity
Systematic name: 3α-Hydroxy-7-oxo-5β-cholanic acid
Also known as: 7-Keto-lithocholic acid or 7-oxolithocholic acid
Molecular formula: C₂₄H₃₈O₄
Structure: Features a steroid nucleus with:
A 3α-hydroxyl group (–OH),
A 7-keto group (=O at position 7),
A 5β configuration (A/B ring fusion typical of bile acids),
A carboxylic acid side chain at C-17.
It is formed during bile acid metabolism, particularly via oxidation by gut bacteria or hepatic enzymes.
🧪 Biological Role & Metabolism
It is an intermediate in the alternative (acidic) pathway of bile acid synthesis.
Produced when chenodeoxycholic acid (CDCA) undergoes 7α-dehydroxylation and oxidation, often by intestinal microbiota.
Can be further metabolized to lithocholic acid (LCA), a secondary bile acid that is more hydrophobic and potentially cytotoxic at high levels.
📌 Known Uses & Applications
1. Research Tool in Biochemistry & Pharmacology
Used to study:
Bile acid metabolism and transport,
Enzyme activity (e.g., 7α-hydroxysteroid dehydrogenases),
Nuclear receptor signaling (e.g., FXR, PXR, TGR5).
Helps understand how oxidative modifications affect bile acid toxicity, solubility, and signaling.
2. Biomarker in Clinical Diagnostics
Elevated levels may indicate:
Altered gut microbiome composition,
Cholestatic liver disease,
Impaired bile acid recycling.
Measured in serum or feces in metabolic studies.
3. Potential Role in Drug Development
Derivatives of oxo-bile acids are explored for:
Modulating farnesoid X receptor (FXR) activity,
Treating metabolic disorders (e.g., non-alcoholic fatty liver disease, NAFLD),
Developing bile acid sequestrants or analogs with improved safety profiles.
⚠️ Note: Unlike therapeutic bile acids such as ursodeoxycholic acid (UDCA) or obeticholic acid, 3α-hydroxy-7-oxo-5β-cholanic acid itself is not used clinically as a drug. It is primarily a metabolic intermediate or research compound.
⚠️ Toxicity Considerations
While less toxic than lithocholic acid, it can still contribute to hepatotoxicity if accumulated due to cholestasis or dysbiosis.
Its presence reflects active microbial and hepatic transformation of bile acids.
✅ Summary
3α-Hydroxy-7-oxo-5β-cholanic acid is:
A natural bile acid metabolite,
Formed during the breakdown of chenodeoxycholic acid,
Used mainly in scientific research to study bile acid pathways,
Evaluated as a biomarker for liver and gut health,
Not a therapeutic agent on its own, but informs the development of bile acid-based drugs.
It plays a key role in understanding the complex interplay between host metabolism, gut microbiota, and liver function.
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