Isolation and Characterization of 1-Hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexene-1-acetic Acid, a Metabolite in Bacterial Transformation of Abscisic Acid
Oleg S. Yuzikhin,
Alexander I. Shaposhnikov,
Tatyana A. Konnova,
Darya S. Syrova,
Hamza Hamo,
Taras S. Ermekkaliev,
Valerii P. Shevchenko,
Konstantin V. Shevchenko,
Natalia E. Gogoleva,
Anton A. Nizhnikov,
Vera I. Safronova,
Alexander A. Kamnev,
Andrey A. Belimov,
Yuri V. Gogolev
Affiliations
Oleg S. Yuzikhin
All-Russia Research Institute for Agricultural Microbiology, Podbelskogo sh. 3, Pushkin, 196608 Saint Petersburg, Russia
Alexander I. Shaposhnikov
All-Russia Research Institute for Agricultural Microbiology, Podbelskogo sh. 3, Pushkin, 196608 Saint Petersburg, Russia
Tatyana A. Konnova
Kazan Institute of Biochemistry and Biophysics, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 420111 Kazan, Russia
Darya S. Syrova
All-Russia Research Institute for Agricultural Microbiology, Podbelskogo sh. 3, Pushkin, 196608 Saint Petersburg, Russia
Hamza Hamo
Institute of Fundamental Medicine and Biology, Kazan (Volga Region) Federal University, Kremlevskaya Street 18, 420008 Kazan, Russia
Taras S. Ermekkaliev
Institute of Fundamental Medicine and Biology, Kazan (Volga Region) Federal University, Kremlevskaya Street 18, 420008 Kazan, Russia
Valerii P. Shevchenko
Institute of Molecular Genetics, Russian Academy of Sciences, Akademika Kurchatova Square 2, 123182 Moscow, Russia
Konstantin V. Shevchenko
Institute of Molecular Genetics, Russian Academy of Sciences, Akademika Kurchatova Square 2, 123182 Moscow, Russia
Natalia E. Gogoleva
Kazan Institute of Biochemistry and Biophysics, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 420111 Kazan, Russia
Anton A. Nizhnikov
All-Russia Research Institute for Agricultural Microbiology, Podbelskogo sh. 3, Pushkin, 196608 Saint Petersburg, Russia
Vera I. Safronova
All-Russia Research Institute for Agricultural Microbiology, Podbelskogo sh. 3, Pushkin, 196608 Saint Petersburg, Russia
Alexander A. Kamnev
Institute of Biochemistry and Physiology of Plants and Microorganisms, Subdivision of the Federal State Budgetary Research Institution Saratov Federal Scientific Center of the Russian Academy of Sciences, 410049 Saratov, Russia
Andrey A. Belimov
All-Russia Research Institute for Agricultural Microbiology, Podbelskogo sh. 3, Pushkin, 196608 Saint Petersburg, Russia
Yuri V. Gogolev
Kazan Institute of Biochemistry and Biophysics, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 420111 Kazan, Russia
We report the discovery of a new abscisic acid (ABA) metabolite, found in the course of a mass spectrometric study of ABA metabolism by the rhizosphere bacterium Rhodococcus sp. P1Y. Analogue of (+)-ABA, enriched in tritium in the cyclohexene moiety, was fed in bacterial cells, and extracts containing radioactive metabolites were purified and analyzed to determine their structure. We obtained mass spectral fragmentation patterns and nuclear magnetic resonance spectra of a new metabolite of ABA identified as 1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexene-1-acetic acid, which we named rhodococcal acid (RA) and characterized using several other techniques. This metabolite is the second bacterial ABA degradation product in addition to dehydrovomifoliol that we described earlier. Taken together, these data reveal an unknown ABA catabolic pathway that begins with side chain disassembly, as opposed to the conversion of the cyclohexene moiety in plants. The role of ABA-utilizing bacteria in interactions with other microorganisms and plants is also discussed.
