Active Constituents with Tyrosinase Inhibitory Activities from Waste Tobacco Leaves
One novel compound, (R)‐3, 6‐diethoxy‐4‐hydroxycyclohex‐3‐en‐1‐one (1) and thirteen known compounds were isolated from the waste tobacco leaves. The structures of two compounds (1–2) were confirmed and attributed firstly by the extensive spectroscopic data, including 1D/2D NMR, IR, HR‐ESI‐MS, CD, an...
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| Veröffentlicht in: | Chemistry & biodiversity 2024-06, Vol.21 (6), p.e202400463-n/a |
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| creator | Zhang, Mei Sun, Jia‐Yu Qiu, Hong‐Mao Zhang, Peng Deng, Lu‐Lu Li, Jiang Hao, Xiao‐Jiang Su, Xian‐Kun Mu, Shu‐Zhen |
| description | One novel compound, (R)‐3, 6‐diethoxy‐4‐hydroxycyclohex‐3‐en‐1‐one (1) and thirteen known compounds were isolated from the waste tobacco leaves. The structures of two compounds (1–2) were confirmed and attributed firstly by the extensive spectroscopic data, including 1D/2D NMR, IR, HR‐ESI‐MS, CD, and ECD spectra. Notably, seven compounds (2, 3, 9, 10, 11, 12, and 13) exhibited better tyrosinase inhibitory activity than the positive control kojic acid. The binding modes of these compounds revealed that their structure formed strong hydrogen bonds and van der Waals forces with the active sites of tyrosinase. These results indicated that waste tobacco leaves are good resources for developing tyrosinase inhibitors. |
| doi_str_mv | 10.1002/cbdv.202400463 |
| format | Article |
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The structures of two compounds (1–2) were confirmed and attributed firstly by the extensive spectroscopic data, including 1D/2D NMR, IR, HR‐ESI‐MS, CD, and ECD spectra. Notably, seven compounds (2, 3, 9, 10, 11, 12, and 13) exhibited better tyrosinase inhibitory activity than the positive control kojic acid. The binding modes of these compounds revealed that their structure formed strong hydrogen bonds and van der Waals forces with the active sites of tyrosinase. 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These results indicated that waste tobacco leaves are good resources for developing tyrosinase inhibitors.</description><subject>active constituents</subject><subject>Bonding strength</subject><subject>Chemical bonds</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - isolation & purification</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Hydrogen bonding</subject><subject>Hydrogen bonds</subject><subject>Kojic acid</subject><subject>Molecular Docking Simulation</subject><subject>Molecular Structure</subject><subject>Monophenol Monooxygenase - antagonists & inhibitors</subject><subject>Monophenol Monooxygenase - metabolism</subject><subject>Nicotiana - chemistry</subject><subject>Nicotiana tabacum</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Plant Leaves - chemistry</subject><subject>Structure-Activity Relationship</subject><subject>Tobacco</subject><subject>tobacco agriculture by-production</subject><subject>Tyrosinase</subject><subject>tyrosinase inhibitory activity</subject><subject>Van der Waals forces</subject><subject>waste leaves</subject><issn>1612-1872</issn><issn>1612-1880</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0EtPGzEUBWALgQil3bJElth0k-DXeOxlSB8gRWLRtF2O_LgjHCXjMPYE5d_XEEglNqx8ZX0-uj4IXVAyoYSwa2f9dsIIE4QIyY_QGZWUjalS5Pgw12yEPqW0LL7cq1M04koSWVfsDP2auhy2gGexSznkAbqc8FPID3ix62MKnUmA77qHYEOO_Q6_8JADJNz2cY3_mpQBL6I1zkU8B7OF9BmdtGaV4MvreY5-__i-mN2O5_c_72bT-dhxpvi40o5Z4TU3vq2t5q3wFUhrpasJaCuZ9rV1wghDQABnTmpPreSVF55WTPNz9HWfu-nj4wApN-uQHKxWpoM4pIYTroSgislCr97RZRz6rmxXlNRUM6lUUZO9cuXrqYe22fRhbfpdQ0nzXHfzXHdzqLs8uHyNHewa_IG_9VuA3oOnsILdB3HN7Obbn__h_wDLaow6</recordid><startdate>202406</startdate><enddate>202406</enddate><creator>Zhang, Mei</creator><creator>Sun, Jia‐Yu</creator><creator>Qiu, Hong‐Mao</creator><creator>Zhang, Peng</creator><creator>Deng, Lu‐Lu</creator><creator>Li, Jiang</creator><creator>Hao, Xiao‐Jiang</creator><creator>Su, Xian‐Kun</creator><creator>Mu, Shu‐Zhen</creator><general>Wiley Subscription Services, Inc</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>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6165-3484</orcidid></search><sort><creationdate>202406</creationdate><title>Active Constituents with Tyrosinase Inhibitory Activities from Waste Tobacco Leaves</title><author>Zhang, Mei ; Sun, Jia‐Yu ; Qiu, Hong‐Mao ; Zhang, Peng ; Deng, Lu‐Lu ; Li, Jiang ; Hao, Xiao‐Jiang ; Su, Xian‐Kun ; Mu, Shu‐Zhen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3283-59c2b4d93adf7b93f4d5e6bb6c70e9b629d7bc4a4a0e4e32c69d1b635d4d15293</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>active constituents</topic><topic>Bonding strength</topic><topic>Chemical bonds</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - isolation & purification</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Hydrogen bonding</topic><topic>Hydrogen bonds</topic><topic>Kojic acid</topic><topic>Molecular Docking Simulation</topic><topic>Molecular Structure</topic><topic>Monophenol Monooxygenase - antagonists & inhibitors</topic><topic>Monophenol Monooxygenase - metabolism</topic><topic>Nicotiana - chemistry</topic><topic>Nicotiana tabacum</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Plant Leaves - chemistry</topic><topic>Structure-Activity Relationship</topic><topic>Tobacco</topic><topic>tobacco agriculture by-production</topic><topic>Tyrosinase</topic><topic>tyrosinase inhibitory activity</topic><topic>Van der Waals forces</topic><topic>waste leaves</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Mei</creatorcontrib><creatorcontrib>Sun, Jia‐Yu</creatorcontrib><creatorcontrib>Qiu, Hong‐Mao</creatorcontrib><creatorcontrib>Zhang, Peng</creatorcontrib><creatorcontrib>Deng, Lu‐Lu</creatorcontrib><creatorcontrib>Li, Jiang</creatorcontrib><creatorcontrib>Hao, Xiao‐Jiang</creatorcontrib><creatorcontrib>Su, Xian‐Kun</creatorcontrib><creatorcontrib>Mu, Shu‐Zhen</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry & biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Mei</au><au>Sun, Jia‐Yu</au><au>Qiu, Hong‐Mao</au><au>Zhang, Peng</au><au>Deng, Lu‐Lu</au><au>Li, Jiang</au><au>Hao, Xiao‐Jiang</au><au>Su, Xian‐Kun</au><au>Mu, Shu‐Zhen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Active Constituents with Tyrosinase Inhibitory Activities from Waste Tobacco Leaves</atitle><jtitle>Chemistry & biodiversity</jtitle><addtitle>Chem Biodivers</addtitle><date>2024-06</date><risdate>2024</risdate><volume>21</volume><issue>6</issue><spage>e202400463</spage><epage>n/a</epage><pages>e202400463-n/a</pages><issn>1612-1872</issn><issn>1612-1880</issn><eissn>1612-1880</eissn><abstract>One novel compound, (R)‐3, 6‐diethoxy‐4‐hydroxycyclohex‐3‐en‐1‐one (1) and thirteen known compounds were isolated from the waste tobacco leaves. The structures of two compounds (1–2) were confirmed and attributed firstly by the extensive spectroscopic data, including 1D/2D NMR, IR, HR‐ESI‐MS, CD, and ECD spectra. Notably, seven compounds (2, 3, 9, 10, 11, 12, and 13) exhibited better tyrosinase inhibitory activity than the positive control kojic acid. The binding modes of these compounds revealed that their structure formed strong hydrogen bonds and van der Waals forces with the active sites of tyrosinase. These results indicated that waste tobacco leaves are good resources for developing tyrosinase inhibitors.</abstract><cop>Switzerland</cop><pub>Wiley Subscription Services, Inc</pub><pmid>38606752</pmid><doi>10.1002/cbdv.202400463</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-6165-3484</orcidid></addata></record> |
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| subjects | active constituents Bonding strength Chemical bonds Enzyme Inhibitors - chemistry Enzyme Inhibitors - isolation & purification Enzyme Inhibitors - pharmacology Hydrogen bonding Hydrogen bonds Kojic acid Molecular Docking Simulation Molecular Structure Monophenol Monooxygenase - antagonists & inhibitors Monophenol Monooxygenase - metabolism Nicotiana - chemistry Nicotiana tabacum NMR Nuclear magnetic resonance Plant Leaves - chemistry Structure-Activity Relationship Tobacco tobacco agriculture by-production Tyrosinase tyrosinase inhibitory activity Van der Waals forces waste leaves |
| title | Active Constituents with Tyrosinase Inhibitory Activities from Waste Tobacco Leaves |
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