LIPID MAPS

Deoxycholic acid (DCA) is a secondary bile acid that is formed via microbial transformation of cholic acid in the colon.¹ It can be conjugated to glycine or taurine to produce glycodeoxycholic acid (GDCA) or taurodeoxycholic acid (TDCA), respectively, in hepatocytes.^1,2,3 DCA (0.2% v/v) inhibits spore germination induced by taurocholic acid (TCA) in seven C. difficile strains, as well as inhibits growth and decreases the cytotoxicity of C. difficile culture supernatants to Vero cells when used at a concentration of 0.02% v/v.¹ It inhibits ionizing radiation-induced p53-dependent transcription in a reporter assay using HCT116 cells when used at a concentration of 200 µM.⁴ Fecal and intestinal tissue levels of DCA are increased in a rat model of high-fat diet-induced obesity compared with rats fed a normal diet.⁵ Increased serum DCA levels have been found in patients with colorectal cancer.⁶

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References

1. Schmid, A., Neumann, H., Karrasch, T., et al. Bile acid metabolome after an oral lipid tolerance test by liquid chromatography-tandem mass spectrometry (LC-MS/MS). PLoS One 11(2), e0148869 (2016).

2. Šarenac, T.M., and Mikov, M. Bile acid synthesis: From nature to the chemical modification and synthesis and their applications as drugs and nutrients. Front. Pharmacol. 9, 939 (2018).

3. Qiao, D., Gaitonde, S.V., Qi, W., et al. Deoxycholic acid suppresses p53 by stimulating proteasome-mediated p53 protein degradation. Carcinogenesis 22(6), 957-964 (2001).

4. Bayerdörffer, E., Mannes, G.A., Richter, W.O., et al. Increased serum deoxycholic acid levels in men with colorectal adenomas. Gastroenterology 104(1), 145-151 (1993).

5. Thanissery, R., Winston, J.A., and Theriot, C.M. Inhibition of spore germination, growth, and toxin activity of clinically relevant C. difficile strains by gut microbiota derived secondary bile acids. Anaerobe 45, 86-100 (2017).

6. Lin, H., An, Y., Tang, H., et al. Alterations of bile acids and gut microbiota in obesity induced by high fat diet in rat model. J. Agric. Food Chem. 67(13), 3624-3632 (2019).

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Naturally Occurring Bile Acids and Alcohols and Their Origins,
The Bile Acids Chemistry, Physiology, and Metabolism, 1971

DOI: 10.1007/978-1-4757-0647-5_2

InChiKey (Click to copy)

KXGVEGMKQFWNSR-LLQZFEROSA-N

InChi (Click to copy)

InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])C[C@H](O)[C@]4(C)[C@@]([H])([C@]([H])(C)CCC(O)=O)CC[C@@]4([H])[C@]3([H])CC[C@]2([H])C[C@H](O)C1

Wikipedia

KEGG ID

HMDB ID

CHEBI ID

LIPIDBANK ID

BBA0040