Supporting Information
Supporting Information features Figure S1 relative to the C7 dehydroxylation mechanism of hydroxysteroids and Figure S2 relative to the postulated biochemical pathway for the C12 dehydroxylation.
| Supporting Information File 1: Supporting Figures S1 and S2. | ||
| Format: PDF | Size: 611.6 KB | Download |
Cite the Following Article
Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review
Fabio Tonin and Isabel W. C. E. Arends
Beilstein J. Org. Chem. 2018, 14, 470–483.
https://doi.org/10.3762/bjoc.14.33
How to Cite
Tonin, F.; Arends, I. W. C. E. Beilstein J. Org. Chem. 2018, 14, 470–483. doi:10.3762/bjoc.14.33
Download Citation
Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window
below.
Citation data in RIS format can be imported by all major citation management software, including EndNote,
ProCite, RefWorks, and Zotero.
Presentation Graphic
| Picture with graphical abstract, title and authors for social media postings and presentations. | ||
| Format: PNG | Size: 759.5 KB | Download |
Citations to This Article
Up to 20 of the most recent references are displayed here.
Scholarly Works
- Chong, A. E. Y.; Sasmita, A. O.; Koh, R. Y.; Ling, A. P. K. Neuroprotective effects of ursodeoxycholic acid in Parkinson's disease and Alzheimer's disease. Neuroprotection 2026. doi:10.1002/nep3.70039
- Lale, S. K.; Charde, V.; Kumar, V.; Acharya, R. Integrated molecular and multi-instrumental characterization of gorochana (Calculus bovis): Authentication of a medicinally important bovine gallstone. Systems Ethnopharmacology and Sustainable Bioresources 2026, 1, 100011. doi:10.1016/j.sesb.2026.100011
- Hu, Y.; Wan, J.; Gao, T.; Xiao, Y.; Cao, X. Catalyst-Free Electrochemical Synthesis of Ursodeoxycholic Acid: Solvent-Dependent Selectivity and Mechanistic Investigation. Elsevier BV 2026. doi:10.2139/ssrn.6250730
- Chen, R.; Sun, M.; Su, C.; Liu, Y.; Chen, Q.; Li, X.; Zhang, L. Conversion of chenodeoxycholic acid to ursodeoxycholic acid by high-performance segmented continuous-flow with whole-cell catalysis. Elsevier BV 2026. doi:10.2139/ssrn.6838141
- Yang, H.; Chen, Y.; Liu, W.; Shen, W.; Xia, Y.; Zhou, L.; Chen, X. Engineering 7β-HSDH_Osp for enhanced catalytic efficiency: Advancing sustainable biosynthesis of ursodeoxycholic acid. Bioresource technology 2025, 443, 133876. doi:10.1016/j.biortech.2025.133876
- Li, P.; Wang, J.; Hao, H.; Chen, X.; He, X.; Shao, Q. Advances in Pharmacological Activities, Biosynthesis, and Structural Modification of Ursodeoxycholic Acid (UDCA): A Review. Drug design, development and therapy 2025, 19, 10775–10810. doi:10.2147/dddt.s557300
- Pope, R.; Visconti, A.; Zhang, X.; Louca, P.; Baleanu, A.-F.; Lin, Y.; Asnicar, F.; Bermingham, K.; Wong, K. E.; Michelotti, G. A.; Wolf, J.; Segata, N.; Berry, S. E.; Spector, T. D.; Leeming, E. R.; Gibson, R.; Menni, C.; Falchi, M. Faecal metabolites as a readout of habitual diet capture dietary interactions with the gut microbiome. Nature communications 2025, 16, 10051. doi:10.1038/s41467-025-66046-7
- Zhou, Z.-R.; Deng, F.-Z.; Zhong, Y.-H.; Li, S.; Dong, C.-Z.; Zhang, L. Engineering a 7β-hydroxylase from fusarium longipes for enhancement of ursodeoxycholic acid production. International journal of biological macromolecules 2025, 333, 148795. doi:10.1016/j.ijbiomac.2025.148795
- Poshekhontseva, V.; Nikolaeva, V.; Shutov, A.; Kazantsev, A.; Sazonova, O.; Strizhov, N.; Donova, M. Steroid Hydroxylation by Mutant Cytochrome P450 BM3-LG23 Using Two Expression Chassis. International journal of molecular sciences 2025, 26, 10728. doi:10.3390/ijms262110728
- Zhu, A.; Zhang, X.; Yan, X. Olfactory detection of ursodeoxycholic acid (UDCA) in large yellow croaker (Larimichthys crocea): responses, pathways and receptor functions. The Journal of experimental biology 2025, 228. doi:10.1242/jeb.250571
- Yang, Z.; Liu, C.; Jin, Y.; Wang, J.; Ma, Y.; Zou, J.; Han, Y.; Guan, Y.; Zhao, W.; Wu, Q. Bioconversion for ursodeoxycholic acid using β-cyclodextrin included-chenodeoxycholic acid via immobilized cells of Xanthomonas maltophilia. Journal of biotechnology 2025, 409, 44–56. doi:10.1016/j.jbiotec.2025.10.004
- Moon, S.; Smanski, M. J. Biosynthesis of tauro-ursodeoxycholic acid (TUDCA) in Saccharomyces cerevisiae. Microbial cell factories 2025, 24, 212. doi:10.1186/s12934-025-02829-3
- Feng, J.; Xue, J.; Hu, X.; Ren, L.; Ren, L. Catalytic Mechanism and Engineering of Hydroxysteroid Dehydrogenases in the Biosynthesis of Ursodeoxycholic Acid. Journal of agricultural and food chemistry 2025, 73, 25177–25189. doi:10.1021/acs.jafc.5c09495
- Bhan, S.; Kumar, S.; Gautam, R.; Yadav, P. S.; Gautam, G. D.; Mahajan, S. Innovative catalytic approaches for optimizing biodiesel production: A review of homogeneous, heterogeneous, enzymatic, and nanostructured catalysts. Environmental Progress & Sustainable Energy 2025, 44. doi:10.1002/ep.70052
- Song, C.; Zheng, X.; Zhou, Z.; Yu, Y.; Zhang, L.; Li, S. Enhanced Regioselectivity and Catalytic Activity on C7Hydroxylation of Lithocholic Acid to Produce Ursodeoxycholic Acid by Monooxygenase CYP107D1 Based on Semi-Rational Design. Biotechnology journal 2025, 20, e70070. doi:10.1002/biot.70070
- Holert, J.; Wilhelm, R.; Henker, J.; Reinker, C. A.; Müller, F. M.; Philipp, B. Chicken Manure as a Sustainable Bile Acid Source for Biotechnological Applications. Microbial biotechnology 2025, 18, e70178. doi:10.1111/1751-7915.70178
- Richtsmeier, P.; Nedielkov, R.; Haring, M.; Yücel, O.; Elsner, L.; Lülf, R. H.; Wöhlbrand, L.; Rabus, R.; Moeller, H.; Philipp, B.; Mueller, F. M. 7β-Hydroxysteroid dehydratase Hsh3 eliminates the 7-hydroxy group of the bile salt ursodeoxycholate during degradation by Sphingobium sp. strain Chol11 and other Sphingomonadaceae. Applied and environmental microbiology 2025, 91, e0018525. doi:10.1128/aem.00185-25
- Benedetto Tiz, D.; Rosati, O.; Sancineto, L. Sulfur- and phosphorus-containing FDA approved drugs in the last five years (2020–2024): A journey among small molecules. Phosphorus, Sulfur, and Silicon and the Related Elements 2025, 1–39. doi:10.1080/10426507.2025.2496521
- Zheng, W.; Bakker, W.; Jin, M.; Wang, J.; Rietjens, I. M. C. M. Organophosphate pesticides modulate gut microbiota and influence bile acid metabolism in an in vitro fermentation model. Environment international 2025, 199, 109469. doi:10.1016/j.envint.2025.109469
- Jing, S.; Wang, Z.; Wang, Y.; Yang, Y.; Song, J.; Zhang, B. Studies on the Synthesis Process of Plant-Derived Ursodeoxycholic Acid Intermediates. Molecules (Basel, Switzerland) 2025, 30, 1454. doi:10.3390/molecules30071454
Patents
- HOLKAR ANIL GANPATRAO; MANJATHURU MAHALINGA; CHOWDARY YIRIGINENI RAMAKRISHNA; GURUGUBELLI SWARAJYA LAKSHMI; NAIK DINESH NARAYAN; POOJARY SANTHOSHA SHEENA. A HIGH YIELDING ENANTIOSELECTIVE ENZYMATIC PROCESS FOR PREPARING URSODEOXYCHOLIC ACID. EP 4678763 A1, Jan 14, 2026.
- BORNSCHEUER UWE; GROBE SASCHA; HANNEVIK EMIL; BAYER THOMAS; BADENHORST CHRISTOFFEL; BRUNDIEK HENRIKE; GROSSJOHANN BEATRICE. PROCESS FOR 7-BETA-HYDROXYLATION OF BILE ACID DERIVATIVES. EP 3933036 B1, Dec 17, 2025.
- STAUNIG NICOLE; DONSBACH KAI OLIVER. Method for the hydroxylation of steroids. US 12305212 B2, May 20, 2025.
- STAUNIG NICOLE; DUPONT MARIA; KOCH DENNIS. NAD(P)H OXIDASE. WO 2025012236 A1, Jan 16, 2025.
- STAUNIG NICOLE; DUPONT MARIA; KOCH DENNIS. NAD(P)H OXIDASE. EP 4488368 A1, Jan 8, 2025.
- CASTALDI MICHELE; CASTALDI GRAZIANO. MICROBIOLOGICAL PROCESS FOR THE PREPARATION OF URSOCHOLIC ACID. WO 2022023155 A1, Feb 3, 2022.
- BORNSCHEUER UWE; GROBE SASCHA; HANNEVIK EMIL; BAYER THOMAS; BADENHORST CHRISTOFFEL; BRUNDIEK HENRIKE; GROSSJOHANN BEATRICE. PROCESS FOR 7-BETA-HYDROXYLATION OF BILE ACID DERIVATIVES. EP 3933036 A1, Jan 5, 2022.
- STAUNIG NICOLE; DONSBACH KAI OLIVER. PROCESS FOR HYDROXYLATING STEROIDS. WO 2021176068 A1, Sept 10, 2021.
- STAUNIG NICOLE; DONSBACH KAI OLIVER. METHOD FOR HYDROXYLATION OF STEROIDS. EP 3875596 A1, Sept 8, 2021.
- KIM HEE TAEK; RYU MI HEE; JUNG YE JEAN; SONG BONG KEUN; KANG KYOUNG HEE. METHOD FOR PRODUCING URSODEOXYCHOLIC ACID USING DEEP EUTECTIC SOLVENT. WO 2021085997 A1, May 6, 2021.
- ENQUIST-NEWMAN MARIA; TOM ERIN; HO CLEO; SAVILE CHRISTOPHER; KUMAR ABHINAV; ESSER LAUREN; CHAN ANDREA; CLAY MICHAEL; PIGULA ADRIANNA; CHEN HSIANG-YUN. CELLS AND METHODS FOR THE PRODUCTION OF URSODEOXYCHOLIC ACID AND PRECURSORS THEREOF. WO 2020076819 A1, April 16, 2020.