Biosynthesis of 6- and 7‑Mono-Demethylated Nobiletins by a Newly Isolated Strain of Yeast
Demethylated nobiletins (DMNs), which are generally recognized as the metabolites of orally administered nobiletin, are widely investigated. However, studies related to 8-demethylated-nobiletin, 7-demethylated-nobiletin (7DMN), and 6-demethylated-nobiletin (6DMN) are limited due to the lack of a syn...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2022-12, Vol.70 (49), p.15439-15448 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Su, Shiwei Zhao, Denggao Yuan, Bo Ma, Yanyan Zhu, Siyue Xu, Kuangyu Lee, Grace Ho, Chi-Tang Huang, Qingrong |
| description | Demethylated nobiletins (DMNs), which are generally recognized as the metabolites of orally administered nobiletin, are widely investigated. However, studies related to 8-demethylated-nobiletin, 7-demethylated-nobiletin (7DMN), and 6-demethylated-nobiletin (6DMN) are limited due to the lack of a synthesis method. In this study, a strain of microbe able to metabolize nobiletin was isolated from aged orange peel. Internal transcribed spacers (ITS) rRNA sequencing analysis showed it belonged to the yeast family, Filobasidium magnum specie. High-performance liquid chromatography (HPLC), HPLC-MS, and 13C NMR results proved that the metabolites were 7DMN and 6DMN. Growth curves of the isolated yeast were studied at different temperatures, media pH, NaCl, and glucose concentrations. Meanwhile, factors that influence the demethylation efficiencies were also investigated. This study lays the groundwork for the investigation of the biological functions of these two compounds and opens a new window for further research of the metabolic fate of nobiletin in the human body. |
| doi_str_mv | 10.1021/acs.jafc.2c03822 |
| format | Article |
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However, studies related to 8-demethylated-nobiletin, 7-demethylated-nobiletin (7DMN), and 6-demethylated-nobiletin (6DMN) are limited due to the lack of a synthesis method. In this study, a strain of microbe able to metabolize nobiletin was isolated from aged orange peel. Internal transcribed spacers (ITS) rRNA sequencing analysis showed it belonged to the yeast family, Filobasidium magnum specie. High-performance liquid chromatography (HPLC), HPLC-MS, and 13C NMR results proved that the metabolites were 7DMN and 6DMN. Growth curves of the isolated yeast were studied at different temperatures, media pH, NaCl, and glucose concentrations. Meanwhile, factors that influence the demethylation efficiencies were also investigated. This study lays the groundwork for the investigation of the biological functions of these two compounds and opens a new window for further research of the metabolic fate of nobiletin in the human body.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/acs.jafc.2c03822</identifier><identifier>PMID: 36454712</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Bioactive Constituents, Metabolites, and Functions</subject><ispartof>Journal of agricultural and food chemistry, 2022-12, Vol.70 (49), p.15439-15448</ispartof><rights>2022 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a1482-a60231a1c1c9bb3588382e915ac97f9fa8ce62fbcdd21c6cdf6b0585bb32d4763</citedby><cites>FETCH-LOGICAL-a1482-a60231a1c1c9bb3588382e915ac97f9fa8ce62fbcdd21c6cdf6b0585bb32d4763</cites><orcidid>0000-0001-8637-0229</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jafc.2c03822$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jafc.2c03822$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36454712$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Su, Shiwei</creatorcontrib><creatorcontrib>Zhao, Denggao</creatorcontrib><creatorcontrib>Yuan, Bo</creatorcontrib><creatorcontrib>Ma, Yanyan</creatorcontrib><creatorcontrib>Zhu, Siyue</creatorcontrib><creatorcontrib>Xu, Kuangyu</creatorcontrib><creatorcontrib>Lee, Grace</creatorcontrib><creatorcontrib>Ho, Chi-Tang</creatorcontrib><creatorcontrib>Huang, Qingrong</creatorcontrib><title>Biosynthesis of 6- and 7‑Mono-Demethylated Nobiletins by a Newly Isolated Strain of Yeast</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Demethylated nobiletins (DMNs), which are generally recognized as the metabolites of orally administered nobiletin, are widely investigated. However, studies related to 8-demethylated-nobiletin, 7-demethylated-nobiletin (7DMN), and 6-demethylated-nobiletin (6DMN) are limited due to the lack of a synthesis method. In this study, a strain of microbe able to metabolize nobiletin was isolated from aged orange peel. Internal transcribed spacers (ITS) rRNA sequencing analysis showed it belonged to the yeast family, Filobasidium magnum specie. High-performance liquid chromatography (HPLC), HPLC-MS, and 13C NMR results proved that the metabolites were 7DMN and 6DMN. Growth curves of the isolated yeast were studied at different temperatures, media pH, NaCl, and glucose concentrations. Meanwhile, factors that influence the demethylation efficiencies were also investigated. This study lays the groundwork for the investigation of the biological functions of these two compounds and opens a new window for further research of the metabolic fate of nobiletin in the human body.</description><subject>Bioactive Constituents, Metabolites, and Functions</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp1kL1OwzAUhS0EoqWwMyE_AC6-Tuw4I5S_SqUMwIAYIsex1VRpXMWpUDZegVfkSXBJYWO6wz3fkc6H0CnQMVAGF0r78VJZPWaaRpKxPTQEzijhAHIfDWnIEMkFDNCR90tKqeQJPUSDSMQ8ToAN0dtV6XxXtwvjS4-dxYJgVRc4-fr4fHC1I9dmZdpFV6nWFHju8rIybVl7nHdY4bl5rzo89a5_P7WNKutty6tRvj1GB1ZV3pzs7gi93N48T-7J7PFuOrmcEQWxZEQJyiJQoEGneR5xKcMUkwJXOk1sapXURjCb66JgoIUurMgplzxkWREnIhoh2vfqxnnfGJutm3Klmi4Dmm09ZcFTtvWU7TwF5KxH1pt8ZYo_4FdMCJz3gR_UbZo6LPi_7xuLWXTJ</recordid><startdate>20221214</startdate><enddate>20221214</enddate><creator>Su, Shiwei</creator><creator>Zhao, Denggao</creator><creator>Yuan, Bo</creator><creator>Ma, Yanyan</creator><creator>Zhu, Siyue</creator><creator>Xu, Kuangyu</creator><creator>Lee, Grace</creator><creator>Ho, Chi-Tang</creator><creator>Huang, Qingrong</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-8637-0229</orcidid></search><sort><creationdate>20221214</creationdate><title>Biosynthesis of 6- and 7‑Mono-Demethylated Nobiletins by a Newly Isolated Strain of Yeast</title><author>Su, Shiwei ; Zhao, Denggao ; Yuan, Bo ; Ma, Yanyan ; Zhu, Siyue ; Xu, Kuangyu ; Lee, Grace ; Ho, Chi-Tang ; Huang, Qingrong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a1482-a60231a1c1c9bb3588382e915ac97f9fa8ce62fbcdd21c6cdf6b0585bb32d4763</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Bioactive Constituents, Metabolites, and Functions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Su, Shiwei</creatorcontrib><creatorcontrib>Zhao, Denggao</creatorcontrib><creatorcontrib>Yuan, Bo</creatorcontrib><creatorcontrib>Ma, Yanyan</creatorcontrib><creatorcontrib>Zhu, Siyue</creatorcontrib><creatorcontrib>Xu, Kuangyu</creatorcontrib><creatorcontrib>Lee, Grace</creatorcontrib><creatorcontrib>Ho, Chi-Tang</creatorcontrib><creatorcontrib>Huang, Qingrong</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Su, Shiwei</au><au>Zhao, Denggao</au><au>Yuan, Bo</au><au>Ma, Yanyan</au><au>Zhu, Siyue</au><au>Xu, Kuangyu</au><au>Lee, Grace</au><au>Ho, Chi-Tang</au><au>Huang, Qingrong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Biosynthesis of 6- and 7‑Mono-Demethylated Nobiletins by a Newly Isolated Strain of Yeast</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2022-12-14</date><risdate>2022</risdate><volume>70</volume><issue>49</issue><spage>15439</spage><epage>15448</epage><pages>15439-15448</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><abstract>Demethylated nobiletins (DMNs), which are generally recognized as the metabolites of orally administered nobiletin, are widely investigated. However, studies related to 8-demethylated-nobiletin, 7-demethylated-nobiletin (7DMN), and 6-demethylated-nobiletin (6DMN) are limited due to the lack of a synthesis method. In this study, a strain of microbe able to metabolize nobiletin was isolated from aged orange peel. Internal transcribed spacers (ITS) rRNA sequencing analysis showed it belonged to the yeast family, Filobasidium magnum specie. High-performance liquid chromatography (HPLC), HPLC-MS, and 13C NMR results proved that the metabolites were 7DMN and 6DMN. Growth curves of the isolated yeast were studied at different temperatures, media pH, NaCl, and glucose concentrations. Meanwhile, factors that influence the demethylation efficiencies were also investigated. This study lays the groundwork for the investigation of the biological functions of these two compounds and opens a new window for further research of the metabolic fate of nobiletin in the human body.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>36454712</pmid><doi>10.1021/acs.jafc.2c03822</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-8637-0229</orcidid></addata></record> |
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| subjects | Bioactive Constituents, Metabolites, and Functions |
| title | Biosynthesis of 6- and 7‑Mono-Demethylated Nobiletins by a Newly Isolated Strain of Yeast |
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