4185-01-7Relevant articles and documents
Biotransformations of Bile Acids with Bacteria from Cayambe Slaughterhouse (Ecuador): Synthesis of Bendigoles
Costa, Stefania,Maldonado Rodriguez, Maria Elena,Rugiero, Irene,De Bastiani, Morena,Medici, Alessandro,Tamburini, Elena,Pedrini, Paola
, p. 969 - 975 (2016/09/09)
The biotransformations of cholic acid (1a), deoxycholic acid (1b), and hyodeoxycholic acid (1c) to bendigoles and other metabolites with bacteria isolated from the rural slaughterhouse of Cayambe (Pichincha Province, Ecuador) were reported. The more active strains were characterized, and belong to the genera Pseudomonas and Rhodococcus. Various biotransformation products were obtained depending on bacteria and substrates. Cholic acid (1a) afforded the 3-oxo and 3-oxo-4-ene derivatives 2a and 3a (45% and 45%, resp.) with P.?mendocina ECS10, 3,12-dioxo-4-ene derivative 4a (60%) with Rh.?erythropolis ECS25, and 9,10-secosteroid 6 (15%) with Rh.?erythropolis ECS12. Bendigole F (5a) was obtained in 20% with P.?fragi ECS22. Deoxycholic acid (1b) gave 3-oxo derivative 2b with P.?prosekii ECS1 and Rh.?erythropolis ECS25 (20% and 61%, resp.), while 3-oxo-4-ene derivative 3b was obtained with P.?prosekii ECS1 and P.?mendocina ECS10 (22% and 95%, resp.). Moreover, P.?fragi ECS9 afforded bendigole A (8b; 80%). Finally, P.?mendocina ECS10 biotransformed hyodeoxycholic acid (1c) to 3-oxo derivative 2c (50%) and Rh.?erythropolis ECS12 to 6α-hydroxy-3-oxo-23,24-dinor-5β-cholan-22-oic acid (9c, 66%). Bendigole G (5c; 13%) with P.?prosekii ECS1 and bendigole H?(8c) with P.?prosekii ECS1 and Rh.?erythropolis ECS12 (20% and 16%, resp.) were obtained.
Deoxycholic acid transformations catalyzed by selected filamentous fungi
Kollerov,Lobastova,Monti,Deshcherevskaya,Ferrandi,Fronza,Riva,Donova
, p. 20 - 29 (2016/03/04)
More than 100 filamentous fungi strains, mostly ascomycetes and zygomycetes from different phyla, were screened for the ability to convert deoxycholic acid (DCA) to valuable bile acid derivatives. Along with 11 molds which fully degraded DCA, several strains were revealed capable of producing cholic acid, ursocholic acid, 12-keto-lithocholic acid (12-keto-LCA), 3-keto-DCA, 15β-hydroxy-DCA and 15β-hydroxy-12-oxo-LCA as major products from DCA. The last metabolite was found to be a new compound. The ability to catalyze the introduction of a hydroxyl group at the 7(α/β)-positions of the DCA molecule was shown for 32 strains with the highest 7β-hydroxylase activity level for Fusarium merismoides VKM F-2310. Curvularia lunata VKM F-644 exhibited 12α-hydroxysteroid dehydrogenase activity and formed 12-keto-LCA from DCA. Acremonium rutilum VKM F-2853 and Neurospora crassa VKM F-875 produced 15β-hydroxy-DCA and 15β-hydroxy-12-oxo-LCA, respectively, as major products from DCA, as confirmed by MS and NMR analyses. For most of the positive strains, the described DCA-transforming activity was unreported to date. The presented results expand the knowledge on bile acid metabolism by filamentous fungi, and might be suitable for preparative-scale exploitation aimed at the production of marketed bile acids.
STUDIES DIRECTED TOWARD SYNTHESIS OF QUASSINOIDS VII .- CONVERSION OF CHENODEOXYCHOLIC ACID TO A δ-LACTONE QUASSINOID ANALOG AND GENERATION OF A-RING DIOSPHENOL ACETATE DERIVATIVES OF DEOXYCHOLIC ACID
Dias, Jerry Ray,Nassim, Bahman
, p. 405 - 418 (2007/10/02)
Chenodeoxycholic acid was converted to a new 5,14-epi-28,30-dinorquassinoid analog.Two isomeric A-ring diosphenol acetate derivatives of deoxycholic acid were synthesized.A 3-oxo-5β-steroid was transformed to a 4-acetoxy-3-oxo-Δ4-steroid by treatment with base and oxygen or to a 2-acetoxy-3-oxo-Δ2-steroid by reaction with cupric chloride in refluxing acetic acid followed by acetylation.Ketene extrusion is a characteristic mass spectral fragmentation of these diosphenol acetates.
