Identification of Highly Potent α‐Glucosidase Inhibitors from Artocarpus integer and Molecular Docking Studies
A new natural Diels‐Alder adduct (3) was isolated from the leaves and stem bark of Artocarpus integer, along with seventeen known compounds (1, 2, and 4–18). Structural elucidation was conducted using NMR and HR‐ESI‐MS data, and comparisons were made with previous studies. Deoxyartonin I (3) exhibit...
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| Veröffentlicht in: | Chemistry & biodiversity 2021-12, Vol.18 (12), p.e2100499-n/a |
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| creator | Duong, Thuc‐Huy Nguyen, Huy Troung Nguyen, Chuong Hoang Tran, Nguyen‐Minh‐An Danova, Ade Tran, Thi‐Minh‐Dinh Vu‐Huynh, Kim Long Musa, Vassana Jutakanoke, Rumpa Nguyen, Ngoc‐Hong Sichaem, Jirapast |
| description | A new natural Diels‐Alder adduct (3) was isolated from the leaves and stem bark of Artocarpus integer, along with seventeen known compounds (1, 2, and 4–18). Structural elucidation was conducted using NMR and HR‐ESI‐MS data, and comparisons were made with previous studies. Deoxyartonin I (3) exhibited the most potent α‐glucosidase inhibition (IC50 7.80±0.1 μM), outperforming the acarbose positive control. This was mixed‐mode inhibition, as indicated by the intersect in the second quadrant of each respective plot. An in silico molecular docking model and the pharmacokinetic features of 3 suggest that it is a potential inhibitor of enzyme α‐glucosidase, and is therefore a lead candidate as a drug against diabetes mellitus. |
| doi_str_mv | 10.1002/cbdv.202100499 |
| format | Article |
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Structural elucidation was conducted using NMR and HR‐ESI‐MS data, and comparisons were made with previous studies. Deoxyartonin I (3) exhibited the most potent α‐glucosidase inhibition (IC50 7.80±0.1 μM), outperforming the acarbose positive control. This was mixed‐mode inhibition, as indicated by the intersect in the second quadrant of each respective plot. An in silico molecular docking model and the pharmacokinetic features of 3 suggest that it is a potential inhibitor of enzyme α‐glucosidase, and is therefore a lead candidate as a drug against diabetes mellitus.</description><identifier>ISSN: 1612-1872</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.202100499</identifier><identifier>PMID: 34761862</identifier><language>eng</language><publisher>Switzerland: Wiley Subscription Services, Inc</publisher><subject>Acarbose ; alpha-Glucosidases - metabolism ; Artocarpus - chemistry ; Artocarpus integer ; Bark ; Diabetes mellitus ; Dose-Response Relationship, Drug ; Glucosidase ; Glycoside Hydrolase Inhibitors - chemistry ; Glycoside Hydrolase Inhibitors - isolation & purification ; Glycoside Hydrolase Inhibitors - pharmacology ; Humans ; Integers ; Molecular docking ; molecular docking model ; Molecular Docking Simulation ; Moraceae ; NMR ; Nuclear magnetic resonance ; Pharmacokinetics ; Plant Components, Aerial - chemistry ; Plant Extracts - chemistry ; Plant Extracts - isolation & purification ; Plant Extracts - pharmacology ; α-glucosidase inhibition</subject><ispartof>Chemistry & biodiversity, 2021-12, Vol.18 (12), p.e2100499-n/a</ispartof><rights>2021 Wiley‐VHCA AG, Zurich, Switzerland</rights><rights>2021 Wiley-VHCA AG, Zurich, Switzerland.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3739-63a118dee6bd9464daac125a2e7bb80fa759b0f6fc22496f4e56454070d9afe83</citedby><cites>FETCH-LOGICAL-c3739-63a118dee6bd9464daac125a2e7bb80fa759b0f6fc22496f4e56454070d9afe83</cites><orcidid>0000-0003-4279-3873</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbdv.202100499$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.202100499$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34761862$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Duong, Thuc‐Huy</creatorcontrib><creatorcontrib>Nguyen, Huy Troung</creatorcontrib><creatorcontrib>Nguyen, Chuong Hoang</creatorcontrib><creatorcontrib>Tran, Nguyen‐Minh‐An</creatorcontrib><creatorcontrib>Danova, Ade</creatorcontrib><creatorcontrib>Tran, Thi‐Minh‐Dinh</creatorcontrib><creatorcontrib>Vu‐Huynh, Kim Long</creatorcontrib><creatorcontrib>Musa, Vassana</creatorcontrib><creatorcontrib>Jutakanoke, Rumpa</creatorcontrib><creatorcontrib>Nguyen, Ngoc‐Hong</creatorcontrib><creatorcontrib>Sichaem, Jirapast</creatorcontrib><title>Identification of Highly Potent α‐Glucosidase Inhibitors from Artocarpus integer and Molecular Docking Studies</title><title>Chemistry & biodiversity</title><addtitle>Chem Biodivers</addtitle><description>A new natural Diels‐Alder adduct (3) was isolated from the leaves and stem bark of Artocarpus integer, along with seventeen known compounds (1, 2, and 4–18). Structural elucidation was conducted using NMR and HR‐ESI‐MS data, and comparisons were made with previous studies. Deoxyartonin I (3) exhibited the most potent α‐glucosidase inhibition (IC50 7.80±0.1 μM), outperforming the acarbose positive control. This was mixed‐mode inhibition, as indicated by the intersect in the second quadrant of each respective plot. An in silico molecular docking model and the pharmacokinetic features of 3 suggest that it is a potential inhibitor of enzyme α‐glucosidase, and is therefore a lead candidate as a drug against diabetes mellitus.</description><subject>Acarbose</subject><subject>alpha-Glucosidases - metabolism</subject><subject>Artocarpus - chemistry</subject><subject>Artocarpus integer</subject><subject>Bark</subject><subject>Diabetes mellitus</subject><subject>Dose-Response Relationship, Drug</subject><subject>Glucosidase</subject><subject>Glycoside Hydrolase Inhibitors - chemistry</subject><subject>Glycoside Hydrolase Inhibitors - isolation & purification</subject><subject>Glycoside Hydrolase Inhibitors - pharmacology</subject><subject>Humans</subject><subject>Integers</subject><subject>Molecular docking</subject><subject>molecular docking model</subject><subject>Molecular Docking Simulation</subject><subject>Moraceae</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Pharmacokinetics</subject><subject>Plant Components, Aerial - chemistry</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - isolation & purification</subject><subject>Plant Extracts - pharmacology</subject><subject>α-glucosidase inhibition</subject><issn>1612-1872</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUtOHDEQhq0IFF7ZZhlZYsNmBtvtdreXZAgwEohIJNlabrs8mPS0B7s7aHYcgatwEQ7BSTAamEjZZFWvr36V6kfoMyVjSgg7NI39M2aE5YJL-QFtU0HZiNY12VjnFdtCOyndZD73649oq-CVoLVg2-h2aqHrvfNG9z50ODh85mfX7RJ_D32e4KfH5_uH03YwIXmrE-Bpd-0b34eYsIthjo9iH4yOiyFh3_Uwg4h1Z_FFaMEMrY74OJjfvpvhq36wHtIe2nS6TfDpLe6inyfffkzORueXp9PJ0fnIFFUhR6LQlNYWQDRWcsGt1oayUjOomqYmTlelbIgTzjDGpXAcSsFLTipipXZQF7voYKW7iOF2gNSruU8G2lZ3EIakWCnzQsmKMqP7_6A3YYhdvk6x_CfGKKc8U-MVZWJIKYJTi-jnOi4VJerVDPVqhlqbkRe-vMkOzRzsGn__fgbkCrjzLSz_I6cmX49__RV_ATvqmMo</recordid><startdate>202112</startdate><enddate>202112</enddate><creator>Duong, Thuc‐Huy</creator><creator>Nguyen, Huy Troung</creator><creator>Nguyen, Chuong Hoang</creator><creator>Tran, Nguyen‐Minh‐An</creator><creator>Danova, Ade</creator><creator>Tran, Thi‐Minh‐Dinh</creator><creator>Vu‐Huynh, Kim Long</creator><creator>Musa, Vassana</creator><creator>Jutakanoke, Rumpa</creator><creator>Nguyen, Ngoc‐Hong</creator><creator>Sichaem, Jirapast</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/0000-0003-4279-3873</orcidid></search><sort><creationdate>202112</creationdate><title>Identification of Highly Potent α‐Glucosidase Inhibitors from Artocarpus integer and Molecular Docking Studies</title><author>Duong, Thuc‐Huy ; Nguyen, Huy Troung ; Nguyen, Chuong Hoang ; Tran, Nguyen‐Minh‐An ; Danova, Ade ; Tran, Thi‐Minh‐Dinh ; Vu‐Huynh, Kim Long ; Musa, Vassana ; Jutakanoke, Rumpa ; Nguyen, Ngoc‐Hong ; Sichaem, Jirapast</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3739-63a118dee6bd9464daac125a2e7bb80fa759b0f6fc22496f4e56454070d9afe83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Acarbose</topic><topic>alpha-Glucosidases - metabolism</topic><topic>Artocarpus - chemistry</topic><topic>Artocarpus integer</topic><topic>Bark</topic><topic>Diabetes mellitus</topic><topic>Dose-Response Relationship, Drug</topic><topic>Glucosidase</topic><topic>Glycoside Hydrolase Inhibitors - chemistry</topic><topic>Glycoside Hydrolase Inhibitors - isolation & purification</topic><topic>Glycoside Hydrolase Inhibitors - pharmacology</topic><topic>Humans</topic><topic>Integers</topic><topic>Molecular docking</topic><topic>molecular docking model</topic><topic>Molecular Docking Simulation</topic><topic>Moraceae</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Pharmacokinetics</topic><topic>Plant Components, Aerial - chemistry</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - isolation & purification</topic><topic>Plant Extracts - pharmacology</topic><topic>α-glucosidase inhibition</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Duong, Thuc‐Huy</creatorcontrib><creatorcontrib>Nguyen, Huy Troung</creatorcontrib><creatorcontrib>Nguyen, Chuong Hoang</creatorcontrib><creatorcontrib>Tran, Nguyen‐Minh‐An</creatorcontrib><creatorcontrib>Danova, Ade</creatorcontrib><creatorcontrib>Tran, Thi‐Minh‐Dinh</creatorcontrib><creatorcontrib>Vu‐Huynh, Kim Long</creatorcontrib><creatorcontrib>Musa, Vassana</creatorcontrib><creatorcontrib>Jutakanoke, Rumpa</creatorcontrib><creatorcontrib>Nguyen, Ngoc‐Hong</creatorcontrib><creatorcontrib>Sichaem, Jirapast</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>Duong, Thuc‐Huy</au><au>Nguyen, Huy Troung</au><au>Nguyen, Chuong Hoang</au><au>Tran, Nguyen‐Minh‐An</au><au>Danova, Ade</au><au>Tran, Thi‐Minh‐Dinh</au><au>Vu‐Huynh, Kim Long</au><au>Musa, Vassana</au><au>Jutakanoke, Rumpa</au><au>Nguyen, Ngoc‐Hong</au><au>Sichaem, Jirapast</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of Highly Potent α‐Glucosidase Inhibitors from Artocarpus integer and Molecular Docking Studies</atitle><jtitle>Chemistry & biodiversity</jtitle><addtitle>Chem Biodivers</addtitle><date>2021-12</date><risdate>2021</risdate><volume>18</volume><issue>12</issue><spage>e2100499</spage><epage>n/a</epage><pages>e2100499-n/a</pages><issn>1612-1872</issn><eissn>1612-1880</eissn><abstract>A new natural Diels‐Alder adduct (3) was isolated from the leaves and stem bark of Artocarpus integer, along with seventeen known compounds (1, 2, and 4–18). Structural elucidation was conducted using NMR and HR‐ESI‐MS data, and comparisons were made with previous studies. Deoxyartonin I (3) exhibited the most potent α‐glucosidase inhibition (IC50 7.80±0.1 μM), outperforming the acarbose positive control. This was mixed‐mode inhibition, as indicated by the intersect in the second quadrant of each respective plot. An in silico molecular docking model and the pharmacokinetic features of 3 suggest that it is a potential inhibitor of enzyme α‐glucosidase, and is therefore a lead candidate as a drug against diabetes mellitus.</abstract><cop>Switzerland</cop><pub>Wiley Subscription Services, Inc</pub><pmid>34761862</pmid><doi>10.1002/cbdv.202100499</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0003-4279-3873</orcidid></addata></record> |
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| subjects | Acarbose alpha-Glucosidases - metabolism Artocarpus - chemistry Artocarpus integer Bark Diabetes mellitus Dose-Response Relationship, Drug Glucosidase Glycoside Hydrolase Inhibitors - chemistry Glycoside Hydrolase Inhibitors - isolation & purification Glycoside Hydrolase Inhibitors - pharmacology Humans Integers Molecular docking molecular docking model Molecular Docking Simulation Moraceae NMR Nuclear magnetic resonance Pharmacokinetics Plant Components, Aerial - chemistry Plant Extracts - chemistry Plant Extracts - isolation & purification Plant Extracts - pharmacology α-glucosidase inhibition |
| title | Identification of Highly Potent α‐Glucosidase Inhibitors from Artocarpus integer and Molecular Docking Studies |
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