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

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 sp. P1Y. Analogue of (+)-ABA, enriched in tritium in the cyclohexene moiety, was fed in bacterial cells, and extracts containing radioacti...

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Published in:Biomolecules (Basel, Switzerland) Switzerland), 2022-10, Vol.12 (10), p.1508
Main Authors: Yuzikhin, Oleg S, Shaposhnikov, Alexander I, Konnova, Tatyana A, Syrova, Darya S, Hamo, Hamza, Ermekkaliev, Taras S, Shevchenko, Valerii P, Shevchenko, Konstantin V, Gogoleva, Natalia E, Nizhnikov, Anton A, Safronova, Vera I, Kamnev, Alexander A, Belimov, Andrey A, Gogolev, Yuri V
Format: Article
Language:English
Subjects:
1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexene-1-acetic acid
Abscisic acid
Abscisic Acid - metabolism
Acetic Acid
Bacteria
Biodegradation
Biosynthesis
Discovery and exploration
Fungi
Gene expression
Genetic transformation
Glucose
Gram-positive bacteria
Identification and classification
Mass spectrometry
Metabolites
Methods
microbial metabolite
Microorganisms
NMR
NMR spectrometry
Nuclear magnetic resonance
Pathogens
Physiological aspects
phytohormones
Plant Extracts
Plant growth
Rhizosphere
Transformation, Bacterial
Tritium
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Summary: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 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.
ISSN:2218-273X
2218-273X
DOI:10.3390/biom12101508