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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 |
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| creator | 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 |
| description | 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. |
| doi_str_mv | 10.3390/biom12101508 |
| format | article |
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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.</description><subject>1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexene-1-acetic acid</subject><subject>Abscisic acid</subject><subject>Abscisic Acid - metabolism</subject><subject>Acetic Acid</subject><subject>Bacteria</subject><subject>Biodegradation</subject><subject>Biosynthesis</subject><subject>Discovery and exploration</subject><subject>Fungi</subject><subject>Gene expression</subject><subject>Genetic transformation</subject><subject>Glucose</subject><subject>Gram-positive bacteria</subject><subject>Identification and classification</subject><subject>Mass spectrometry</subject><subject>Metabolites</subject><subject>Methods</subject><subject>microbial metabolite</subject><subject>Microorganisms</subject><subject>NMR</subject><subject>NMR spectrometry</subject><subject>Nuclear magnetic resonance</subject><subject>Pathogens</subject><subject>Physiological aspects</subject><subject>phytohormones</subject><subject>Plant Extracts</subject><subject>Plant growth</subject><subject>Rhizosphere</subject><subject>Transformation, Bacterial</subject><subject>Tritium</subject><issn>2218-273X</issn><issn>2218-273X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNptkl2LEzEUhgdR3GXdO69lwBsvmjVfM5ncCN2ibmHFmxW8Cycf06bMTNZkKq2_xJ9ramttxSSQcPKe5_AeTlG8JPiGMYnfah96QgkmFW6eFJeUkgZRwb4-PXlfFNcprXBeTT6UPS8uWE0lEaS5LH7OU-hg9GEoYbDlbAkRzOii_7EPhrYk6G5rY9hsEZ3UkxqN0fduXG47xFHYBESR2ZouLN3GDQ4RBMaN3pRT4-2khPKTG0GHzo-u9EN5u6dDVz5EGFIbYn8sNNXJ-HRIfVE8a6FL7vpwXxVfPrx_mN2h-88f57PpPTIVr0ZEJRaYWkuJlJZLQoSupWZMZ-eciwpjIoWreMN0BdpI0bC2ZUZKp1tbY82uivmeawOs1GP2BnGrAnj1OxDiQkHMfjqnKOFWM8Ox5cBt6zQ0ugFX1RgaJ0Fm1rs963Gte2eNG8YI3Rn0_GfwS7UI35WspBRiB3hzAMTwbe3SqHqfjOs6GFxYJ0UFlRWlQvAsff2PdBXWccit2qkazrKM_VUtIBvwQxtyXbODqqngGUVwsyt78x9V3tb13oTBtT7HzxIm-wQTQ0rRtUePBKvdYKrTwczyV6d9OYr_jCH7BXxz3QY</recordid><startdate>20221001</startdate><enddate>20221001</enddate><creator>Yuzikhin, Oleg S</creator><creator>Shaposhnikov, Alexander I</creator><creator>Konnova, Tatyana A</creator><creator>Syrova, Darya S</creator><creator>Hamo, Hamza</creator><creator>Ermekkaliev, Taras S</creator><creator>Shevchenko, Valerii P</creator><creator>Shevchenko, Konstantin V</creator><creator>Gogoleva, Natalia E</creator><creator>Nizhnikov, Anton A</creator><creator>Safronova, Vera I</creator><creator>Kamnev, Alexander A</creator><creator>Belimov, Andrey A</creator><creator>Gogolev, Yuri V</creator><general>MDPI AG</general><general>MDPI</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7T5</scope><scope>7TM</scope><scope>7TO</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M7P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0001-6677-8227</orcidid><orcidid>https://orcid.org/0000-0002-2391-2980</orcidid><orcidid>https://orcid.org/0000-0002-9936-8678</orcidid><orcidid>https://orcid.org/0000-0002-9173-7854</orcidid><orcidid>https://orcid.org/0000-0002-1818-9230</orcidid><orcidid>https://orcid.org/0000-0002-8338-3494</orcidid><orcidid>https://orcid.org/0000-0003-4510-1772</orcidid><orcidid>https://orcid.org/0000-0003-0771-5589</orcidid></search><sort><creationdate>20221001</creationdate><title>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</title><author>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</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c545t-290702dd2199d49117b69b33b273447500197e5483b5abc9783ff3c99ebfd60b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexene-1-acetic acid</topic><topic>Abscisic acid</topic><topic>Abscisic Acid - metabolism</topic><topic>Acetic Acid</topic><topic>Bacteria</topic><topic>Biodegradation</topic><topic>Biosynthesis</topic><topic>Discovery and exploration</topic><topic>Fungi</topic><topic>Gene expression</topic><topic>Genetic transformation</topic><topic>Glucose</topic><topic>Gram-positive bacteria</topic><topic>Identification and classification</topic><topic>Mass spectrometry</topic><topic>Metabolites</topic><topic>Methods</topic><topic>microbial metabolite</topic><topic>Microorganisms</topic><topic>NMR</topic><topic>NMR spectrometry</topic><topic>Nuclear magnetic resonance</topic><topic>Pathogens</topic><topic>Physiological aspects</topic><topic>phytohormones</topic><topic>Plant Extracts</topic><topic>Plant growth</topic><topic>Rhizosphere</topic><topic>Transformation, Bacterial</topic><topic>Tritium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yuzikhin, Oleg S</creatorcontrib><creatorcontrib>Shaposhnikov, Alexander I</creatorcontrib><creatorcontrib>Konnova, Tatyana A</creatorcontrib><creatorcontrib>Syrova, Darya S</creatorcontrib><creatorcontrib>Hamo, Hamza</creatorcontrib><creatorcontrib>Ermekkaliev, Taras S</creatorcontrib><creatorcontrib>Shevchenko, Valerii P</creatorcontrib><creatorcontrib>Shevchenko, Konstantin V</creatorcontrib><creatorcontrib>Gogoleva, Natalia E</creatorcontrib><creatorcontrib>Nizhnikov, Anton A</creatorcontrib><creatorcontrib>Safronova, Vera I</creatorcontrib><creatorcontrib>Kamnev, Alexander A</creatorcontrib><creatorcontrib>Belimov, Andrey A</creatorcontrib><creatorcontrib>Gogolev, Yuri V</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Immunology Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Oncogenes and Growth Factors Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Natural Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Biological Science Database</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - 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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.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>36291718</pmid><doi>10.3390/biom12101508</doi><orcidid>https://orcid.org/0000-0001-6677-8227</orcidid><orcidid>https://orcid.org/0000-0002-2391-2980</orcidid><orcidid>https://orcid.org/0000-0002-9936-8678</orcidid><orcidid>https://orcid.org/0000-0002-9173-7854</orcidid><orcidid>https://orcid.org/0000-0002-1818-9230</orcidid><orcidid>https://orcid.org/0000-0002-8338-3494</orcidid><orcidid>https://orcid.org/0000-0003-4510-1772</orcidid><orcidid>https://orcid.org/0000-0003-0771-5589</orcidid><oa>free_for_read</oa></addata></record> |
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| language | eng |
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| 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 |
| title | 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 |
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