Metabolism of insecticide diazinon by Cunninghamella elegans ATCC36112
The fungal metabolism of diazinon was investigated and the microbial model ( ATCC36112) could effectively degrade the organophosphorus pesticide (diazinon) mediated by cytochrome P450, which was mainly involved in oxidation and hydrolysis of phase I metabolism. Approximately 89% of diazinon was remo...
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description | The fungal metabolism of diazinon was investigated and the microbial model (
ATCC36112) could effectively degrade the organophosphorus pesticide (diazinon) mediated by cytochrome P450, which was mainly involved in oxidation and hydrolysis of phase I metabolism. Approximately 89% of diazinon was removed within 7 days and was not observed after 13 days with concomitant accumulation of eight metabolites. Structures of the metabolites were fully or tentatively identified with GC-MS and
H,
C NMR. The major metabolites of diazinon were diethyl (2-isopropyl-6-methylpyrimidin-4-yl) phosphate (diazoxon) and 2-isopropyl-6-methyl-4-pyrimidinol (pyrimidinol), and formation of minor metabolites was primarily the result of hydroxylation. To determine the responsible enzymes in diazinon metabolism, piperonyl butoxide and methimazole were treated, and the kinetic responses of diazinon and its metabolites by
were measured. Results indirectly demonstrated that cytochrome P450 and flavin monooxygenase were involved in the metabolism of diazinon, but methimazole inhibited the metabolism less effectively. Based on the metabolic profiling, a possible metabolic pathway involved in phase I metabolism of diazinon was proposed, which would contribute to providing insight into understanding the toxicological effects of diazinon and the potential application of fungi on organophosphorus pesticides. |
doi_str_mv | 10.1039/d0ra02253e |
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ATCC36112) could effectively degrade the organophosphorus pesticide (diazinon) mediated by cytochrome P450, which was mainly involved in oxidation and hydrolysis of phase I metabolism. Approximately 89% of diazinon was removed within 7 days and was not observed after 13 days with concomitant accumulation of eight metabolites. Structures of the metabolites were fully or tentatively identified with GC-MS and
H,
C NMR. The major metabolites of diazinon were diethyl (2-isopropyl-6-methylpyrimidin-4-yl) phosphate (diazoxon) and 2-isopropyl-6-methyl-4-pyrimidinol (pyrimidinol), and formation of minor metabolites was primarily the result of hydroxylation. To determine the responsible enzymes in diazinon metabolism, piperonyl butoxide and methimazole were treated, and the kinetic responses of diazinon and its metabolites by
were measured. Results indirectly demonstrated that cytochrome P450 and flavin monooxygenase were involved in the metabolism of diazinon, but methimazole inhibited the metabolism less effectively. Based on the metabolic profiling, a possible metabolic pathway involved in phase I metabolism of diazinon was proposed, which would contribute to providing insight into understanding the toxicological effects of diazinon and the potential application of fungi on organophosphorus pesticides.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d0ra02253e</identifier><identifier>PMID: 35515422</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Chemistry ; Cytochrome ; Cytochromes P450 ; Hydroxylation ; Insecticides ; Metabolism ; Metabolites ; Microorganisms ; NMR ; Nuclear magnetic resonance ; Oxidation ; Pesticides</subject><ispartof>RSC advances, 2020-05, Vol.10 (33), p.19659-19668</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2020</rights><rights>This journal is © The Royal Society of Chemistry 2020 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c377t-c8b7d2a2f388276b712ad6d00b9315e667084cf2c22a63cabcf52f728bb99ade3</citedby><cites>FETCH-LOGICAL-c377t-c8b7d2a2f388276b712ad6d00b9315e667084cf2c22a63cabcf52f728bb99ade3</cites><orcidid>0000-0003-2961-5298</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9054078/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9054078/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35515422$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhao, Mei-Ai</creatorcontrib><creatorcontrib>Gu, Hao</creatorcontrib><creatorcontrib>Zhang, Chuan-Jie</creatorcontrib><creatorcontrib>Jeong, In-Hong</creatorcontrib><creatorcontrib>Kim, Jeong-Han</creatorcontrib><creatorcontrib>Zhu, Yong-Zhe</creatorcontrib><title>Metabolism of insecticide diazinon by Cunninghamella elegans ATCC36112</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>The fungal metabolism of diazinon was investigated and the microbial model (
ATCC36112) could effectively degrade the organophosphorus pesticide (diazinon) mediated by cytochrome P450, which was mainly involved in oxidation and hydrolysis of phase I metabolism. Approximately 89% of diazinon was removed within 7 days and was not observed after 13 days with concomitant accumulation of eight metabolites. Structures of the metabolites were fully or tentatively identified with GC-MS and
H,
C NMR. The major metabolites of diazinon were diethyl (2-isopropyl-6-methylpyrimidin-4-yl) phosphate (diazoxon) and 2-isopropyl-6-methyl-4-pyrimidinol (pyrimidinol), and formation of minor metabolites was primarily the result of hydroxylation. To determine the responsible enzymes in diazinon metabolism, piperonyl butoxide and methimazole were treated, and the kinetic responses of diazinon and its metabolites by
were measured. Results indirectly demonstrated that cytochrome P450 and flavin monooxygenase were involved in the metabolism of diazinon, but methimazole inhibited the metabolism less effectively. Based on the metabolic profiling, a possible metabolic pathway involved in phase I metabolism of diazinon was proposed, which would contribute to providing insight into understanding the toxicological effects of diazinon and the potential application of fungi on organophosphorus pesticides.</description><subject>Chemistry</subject><subject>Cytochrome</subject><subject>Cytochromes P450</subject><subject>Hydroxylation</subject><subject>Insecticides</subject><subject>Metabolism</subject><subject>Metabolites</subject><subject>Microorganisms</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Oxidation</subject><subject>Pesticides</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpdkdFLwzAQxoMobsy9-AdIwRcRpsmlTdsXYdRNBUWQ-RySNN0y2mQ2rTD_ejs3x_Re7uB-fNx3H0LnBN8QTNPbHNcCA0RUH6E-4JCNALP0-GDuoaH3S9wViwgwcop6NIpIFAL00fRFN0K60vgqcEVgrNeqMcrkOsiN-DLW2UCug6y11tj5QlS6LEWgSz0X1gfjWZZRRgicoZNClF4Pd32A3qeTWfY4en59eMrGzyNF47gZqUTGOQgoaJJAzGRMQOQsx1imlESasRgnoSpAAQhGlZCqiKCIIZEyTUWu6QDdbXVXrax0rrRtalHyVW0qUa-5E4b_3Viz4HP3yVMchThOOoGrnUDtPlrtG14ZrzamrHat58AYwQmQ7qEDdPkPXbq2tp09DmH3V4pDSjvqekup2nlf62J_DMF8kxC_x2_jn4QmHXxxeP4e_c2DfgO-LIpn</recordid><startdate>20200526</startdate><enddate>20200526</enddate><creator>Zhao, Mei-Ai</creator><creator>Gu, Hao</creator><creator>Zhang, Chuan-Jie</creator><creator>Jeong, In-Hong</creator><creator>Kim, Jeong-Han</creator><creator>Zhu, Yong-Zhe</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-2961-5298</orcidid></search><sort><creationdate>20200526</creationdate><title>Metabolism of insecticide diazinon by Cunninghamella elegans ATCC36112</title><author>Zhao, Mei-Ai ; Gu, Hao ; Zhang, Chuan-Jie ; Jeong, In-Hong ; Kim, Jeong-Han ; Zhu, Yong-Zhe</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c377t-c8b7d2a2f388276b712ad6d00b9315e667084cf2c22a63cabcf52f728bb99ade3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Chemistry</topic><topic>Cytochrome</topic><topic>Cytochromes P450</topic><topic>Hydroxylation</topic><topic>Insecticides</topic><topic>Metabolism</topic><topic>Metabolites</topic><topic>Microorganisms</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Oxidation</topic><topic>Pesticides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhao, Mei-Ai</creatorcontrib><creatorcontrib>Gu, Hao</creatorcontrib><creatorcontrib>Zhang, Chuan-Jie</creatorcontrib><creatorcontrib>Jeong, In-Hong</creatorcontrib><creatorcontrib>Kim, Jeong-Han</creatorcontrib><creatorcontrib>Zhu, Yong-Zhe</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhao, Mei-Ai</au><au>Gu, Hao</au><au>Zhang, Chuan-Jie</au><au>Jeong, In-Hong</au><au>Kim, Jeong-Han</au><au>Zhu, Yong-Zhe</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metabolism of insecticide diazinon by Cunninghamella elegans ATCC36112</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2020-05-26</date><risdate>2020</risdate><volume>10</volume><issue>33</issue><spage>19659</spage><epage>19668</epage><pages>19659-19668</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>The fungal metabolism of diazinon was investigated and the microbial model (
ATCC36112) could effectively degrade the organophosphorus pesticide (diazinon) mediated by cytochrome P450, which was mainly involved in oxidation and hydrolysis of phase I metabolism. Approximately 89% of diazinon was removed within 7 days and was not observed after 13 days with concomitant accumulation of eight metabolites. Structures of the metabolites were fully or tentatively identified with GC-MS and
H,
C NMR. The major metabolites of diazinon were diethyl (2-isopropyl-6-methylpyrimidin-4-yl) phosphate (diazoxon) and 2-isopropyl-6-methyl-4-pyrimidinol (pyrimidinol), and formation of minor metabolites was primarily the result of hydroxylation. To determine the responsible enzymes in diazinon metabolism, piperonyl butoxide and methimazole were treated, and the kinetic responses of diazinon and its metabolites by
were measured. Results indirectly demonstrated that cytochrome P450 and flavin monooxygenase were involved in the metabolism of diazinon, but methimazole inhibited the metabolism less effectively. Based on the metabolic profiling, a possible metabolic pathway involved in phase I metabolism of diazinon was proposed, which would contribute to providing insight into understanding the toxicological effects of diazinon and the potential application of fungi on organophosphorus pesticides.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>35515422</pmid><doi>10.1039/d0ra02253e</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0003-2961-5298</orcidid><oa>free_for_read</oa></addata></record> |
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source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; PubMed Central Open Access |
subjects | Chemistry Cytochrome Cytochromes P450 Hydroxylation Insecticides Metabolism Metabolites Microorganisms NMR Nuclear magnetic resonance Oxidation Pesticides |
title | Metabolism of insecticide diazinon by Cunninghamella elegans ATCC36112 |
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