The German chemist Heinrich Otto Wieland revealed the structure of bile acids winning the 1927 Nobel Prize for Chemistry for his work.
Bile acids are a class of steroids and share the classic gonane A,B,C,D rings system (three cyclohexane rings A,B,C and the cyclopentane ring D) but with bridge head methyl’s at C10 and C13 and a short aliphatic side chain. The side chain determines the class of bile acids of which there are four main types, C24, C25, C26 and C27.
Bile Acid Numbering (Cholic Acid shown)
Bile acids are structurally quite different than conventional steroids as they have an cis-fused A,B ring where the proton at C-5 is beta (5b-stereochemistry). Some bile acids in lower vertebrates, are allo-bile acids, which are flat due to A/B trans-fusion (5a-stereochemistry).
Chemistry teams are exploring the bile acid scaffold as platforms for drug discovery, novel anionic biosurfactants and utilising the solubilising properties of bile acids / salts as excipients for drugs and vaccines.
Bile acid derivatives as ligands of the farnesoid X receptor. Synthesis, evaluation, and structure-activity relationship of a series of body and side chain modified analogues of chenodeoxycholic acid
Pellicciari R, Costantino G, Camaioni E, Sadeghpour B. M, Entrena A, Willson TM, Fiorucci S, Clerici C, Gioiello A. Journal of Medicinal Chemistry. 47: 4559-69. PMID 15317466 DOI: 10.1021/Jm049904B.
Novel Semisynthetic Derivatives of Bile Acids as Effective Tyrosyl-DNA Phosphodiesterase 1 Inhibitors
Salomatina OV, Popadyuk II, Zakharenko AL, Zakharova OD, Fadeev DS, Komarova NI, Reynisson J, Arabshahi HJ, Chand R, Volcho KP, Salakhutdinov NF, Lavrik OI. Molecules. 2018 Mar 17;23(3):679. doi: 10.3390/molecules23030679.
Bile Acid Conjugates with Anticancer Activity: Most Recent Research
Maria Luisa Navacchia, Elena Marchesi and Daniela Perrone. Molecules, 2020, 23;26(1)25 doi: 10.3390/molecules26010025.
Synthesis of Novel C/D Ring Modified Bile Acids
Roselis A Landaeta Aponte, Andreas Luxenburger, Scott A Cameron , Alex Weymouth-Wilson, Richard H Furneaux , Lawrence D Harris , Benjamin J Compton. Molecules 2022 Apr 6;27(7):2364. doi: 10.3390/molecules27072364.
Novel Derivatives of Deoxycholic Acid Bearing Linear Aliphatic Diamine and Aminoalcohol Moieties and their Cyclic Analogs at the C3 Position: Synthesis and Evaluation of Their In Vitro Antitumor Potential
Markov AV, Babich VO, Popadyuk II, Salomatina OV, Logashenko EB, Salakhutdinov NF, Zenkova MA. Molecules. 2019 Jul 21;24(14):2644. doi: 10.3390/molecules24142644.