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Biotransformations of Bile Acids with Bacteria from Cayambe Slaughterhouse (Ecuador): Synthesis of Bendigoles
Author(s) -
Costa Stefania,
Maldonado Rodriguez Maria Elena,
Rugiero Irene,
De Bastiani Morena,
Medici Alessandro,
Tamburini Elena,
Pedrini Paola
Publication year - 2016
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201500300
Subject(s) - chemistry , deoxycholic acid , cholic acid , biotransformation , bacteria , derivative (finance) , stereochemistry , bile acid , organic chemistry , biochemistry , biology , enzyme , financial economics , economics , genetics
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 ECS 10, 3,12‐dioxo‐4‐ene derivative 4a (60%) with Rh . erythropolis ECS 25, and 9,10‐secosteroid 6 (15%) with Rh . erythropolis ECS 12. Bendigole F ( 5a ) was obtained in 20% with P . fragi ECS 22. Deoxycholic acid ( 1b ) gave 3‐oxo derivative 2b with P . prosekii ECS 1 and Rh . erythropolis ECS 25 (20% and 61%, resp.), while 3‐oxo‐4‐ene derivative 3b was obtained with P . prosekii ECS 1 and P . mendocina ECS 10 (22% and 95%, resp.). Moreover, P. fragi ECS 9 afforded bendigole A ( 8b ; 80%). Finally, P. mendocina ECS 10 biotransformed hyodeoxycholic acid ( 1c ) to 3‐oxo derivative 2c (50%) and Rh . erythropolis ECS 12 to 6 α ‐hydroxy‐3‐oxo‐23,24‐dinor‐5 β ‐cholan‐22‐oic acid ( 9c , 66%). Bendigole G ( 5c ; 13%) with P . prosekii ECS 1 and bendigole H ( 8c ) with P . prosekii ECS 1 and Rh . erythropolis ECS 12 (20% and 16%, resp.) were obtained.