Stilbenes with Potent Protein Tyrosine Phosphatase-1B Inhibitory Activity from the Roots of Polygonum multiflorum
Seven new stilbene glycosides including three dimers (1–3) and four monomers (4–7) were isolated from the roots of Polygonum multiflorum along with nine previously identified stilbenes (8–16). In addition, two deglucosylated stilbenes, 2a and 3a, were also obtained as new dimeric stilbenes. The stru...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2020-02, Vol.83 (2), p.323-332 |
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| creator | Nguyen, Thi-Thuy An Ha, Manh Tuan Park, Se-Eun Choi, Jae Sue Min, Byung Sun Kim, Jeong Ah |
| description | Seven new stilbene glycosides including three dimers (1–3) and four monomers (4–7) were isolated from the roots of Polygonum multiflorum along with nine previously identified stilbenes (8–16). In addition, two deglucosylated stilbenes, 2a and 3a, were also obtained as new dimeric stilbenes. The structures of the purified phytochemicals were elucidated by interpreting their spectroscopic data (NMR, HRMS, and ECD). To the best of our knowledge, this represents the first isolation of a phenylpropanoid (C6–C3) substituted with a stilbene unit (7) from the Polygonaceae family. In an in vitro enzyme assay with human recombinant protein tyrosine phosphatase-1B (PTP1B), compounds 2–5 showed weak PTP1B inhibition with an IC50 value range of 27.4–37.6 μM, while three deglucosylated stilbenes 2a, 3a, and 8a exhibited IC50 values of 2.1, 1.9, and 12.1 μM, respectively. The inhibition modes and binding mechanism of selected inhibitors (2a and 3a) were investigated using kinetic methods and molecular docking simulations. |
| doi_str_mv | 10.1021/acs.jnatprod.9b00777 |
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In addition, two deglucosylated stilbenes, 2a and 3a, were also obtained as new dimeric stilbenes. The structures of the purified phytochemicals were elucidated by interpreting their spectroscopic data (NMR, HRMS, and ECD). To the best of our knowledge, this represents the first isolation of a phenylpropanoid (C6–C3) substituted with a stilbene unit (7) from the Polygonaceae family. In an in vitro enzyme assay with human recombinant protein tyrosine phosphatase-1B (PTP1B), compounds 2–5 showed weak PTP1B inhibition with an IC50 value range of 27.4–37.6 μM, while three deglucosylated stilbenes 2a, 3a, and 8a exhibited IC50 values of 2.1, 1.9, and 12.1 μM, respectively. The inhibition modes and binding mechanism of selected inhibitors (2a and 3a) were investigated using kinetic methods and molecular docking simulations.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/acs.jnatprod.9b00777</identifier><identifier>PMID: 31944695</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - isolation & purification ; Fallopia multiflora - chemistry ; Glycosides - chemistry ; Humans ; Molecular Docking Simulation ; Phytochemicals ; Plant Roots - chemistry ; Polygonaceae - chemistry ; Polygonum - chemistry ; Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors ; Protein Tyrosine Phosphatase, Non-Receptor Type 1 - chemistry ; Protein Tyrosine Phosphatase, Non-Receptor Type 1 - metabolism ; Stilbenes - chemistry ; Stilbenes - isolation & purification</subject><ispartof>Journal of natural products (Washington, D.C.), 2020-02, Vol.83 (2), p.323-332</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-c5e89d0ef2a06ca7aa6256902db1875f41d3584a3c705e9f243fd9bc2e23ba213</citedby><cites>FETCH-LOGICAL-a348t-c5e89d0ef2a06ca7aa6256902db1875f41d3584a3c705e9f243fd9bc2e23ba213</cites><orcidid>0000-0001-9034-8868 ; 0000-0001-7337-1812</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.jnatprod.9b00777$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jnatprod.9b00777$$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/31944695$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nguyen, Thi-Thuy An</creatorcontrib><creatorcontrib>Ha, Manh Tuan</creatorcontrib><creatorcontrib>Park, Se-Eun</creatorcontrib><creatorcontrib>Choi, Jae Sue</creatorcontrib><creatorcontrib>Min, Byung Sun</creatorcontrib><creatorcontrib>Kim, Jeong Ah</creatorcontrib><title>Stilbenes with Potent Protein Tyrosine Phosphatase-1B Inhibitory Activity from the Roots of Polygonum multiflorum</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Seven new stilbene glycosides including three dimers (1–3) and four monomers (4–7) were isolated from the roots of Polygonum multiflorum along with nine previously identified stilbenes (8–16). In addition, two deglucosylated stilbenes, 2a and 3a, were also obtained as new dimeric stilbenes. The structures of the purified phytochemicals were elucidated by interpreting their spectroscopic data (NMR, HRMS, and ECD). To the best of our knowledge, this represents the first isolation of a phenylpropanoid (C6–C3) substituted with a stilbene unit (7) from the Polygonaceae family. In an in vitro enzyme assay with human recombinant protein tyrosine phosphatase-1B (PTP1B), compounds 2–5 showed weak PTP1B inhibition with an IC50 value range of 27.4–37.6 μM, while three deglucosylated stilbenes 2a, 3a, and 8a exhibited IC50 values of 2.1, 1.9, and 12.1 μM, respectively. The inhibition modes and binding mechanism of selected inhibitors (2a and 3a) were investigated using kinetic methods and molecular docking simulations.</description><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - isolation & purification</subject><subject>Fallopia multiflora - chemistry</subject><subject>Glycosides - chemistry</subject><subject>Humans</subject><subject>Molecular Docking Simulation</subject><subject>Phytochemicals</subject><subject>Plant Roots - chemistry</subject><subject>Polygonaceae - chemistry</subject><subject>Polygonum - chemistry</subject><subject>Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors</subject><subject>Protein Tyrosine Phosphatase, Non-Receptor Type 1 - chemistry</subject><subject>Protein Tyrosine Phosphatase, Non-Receptor Type 1 - metabolism</subject><subject>Stilbenes - chemistry</subject><subject>Stilbenes - isolation & purification</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEtP3DAUha2qqAy0_6CqvOwm0-tXEi8pKg9pJEYwrCMnsRujxB5spyj_voYZuuzqbL5zru6H0FcCawKU_FBdXD85lfbB92vZAlRV9QGtiKBQlEDFR7QCUrKC1SU_RWcxPgEAAyk-oVNGJOelFCv0_JDs2GqnI36xacBbn7RLeBtyWod3S_DROo23g4_7QSUVdUF-4ls32NYmHxZ80SX7x6YFm-AnnAaN771PEXuTx8blt3fzhKd5TNaMPszTZ3Ri1Bj1l2Oeo8erX7vLm2Jzd317ebEpFON1Kjqha9mDNlRB2alKqZKKUgLtW1JXwnDSM1FzxboKhJaGcmZ62XZUU9YqStg5-n7YzYKeZx1TM9nY6XFUTvs5NpRxUlIgQmaUH9AufxuDNs0-2EmFpSHQvMpusuzmXXZzlJ1r344X5nbS_b_Su90MwAF4q_s5uPzw_zf_AmxDkTY</recordid><startdate>20200228</startdate><enddate>20200228</enddate><creator>Nguyen, Thi-Thuy An</creator><creator>Ha, Manh Tuan</creator><creator>Park, Se-Eun</creator><creator>Choi, Jae Sue</creator><creator>Min, Byung Sun</creator><creator>Kim, Jeong Ah</creator><general>American Chemical Society and American Society of Pharmacognosy</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>7X8</scope><orcidid>https://orcid.org/0000-0001-9034-8868</orcidid><orcidid>https://orcid.org/0000-0001-7337-1812</orcidid></search><sort><creationdate>20200228</creationdate><title>Stilbenes with Potent Protein Tyrosine Phosphatase-1B Inhibitory Activity from the Roots of Polygonum multiflorum</title><author>Nguyen, Thi-Thuy An ; Ha, Manh Tuan ; Park, Se-Eun ; Choi, Jae Sue ; Min, Byung Sun ; Kim, Jeong Ah</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-c5e89d0ef2a06ca7aa6256902db1875f41d3584a3c705e9f243fd9bc2e23ba213</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - isolation & purification</topic><topic>Fallopia multiflora - chemistry</topic><topic>Glycosides - chemistry</topic><topic>Humans</topic><topic>Molecular Docking Simulation</topic><topic>Phytochemicals</topic><topic>Plant Roots - chemistry</topic><topic>Polygonaceae - chemistry</topic><topic>Polygonum - chemistry</topic><topic>Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors</topic><topic>Protein Tyrosine Phosphatase, Non-Receptor Type 1 - chemistry</topic><topic>Protein Tyrosine Phosphatase, Non-Receptor Type 1 - metabolism</topic><topic>Stilbenes - chemistry</topic><topic>Stilbenes - isolation & purification</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nguyen, Thi-Thuy An</creatorcontrib><creatorcontrib>Ha, Manh Tuan</creatorcontrib><creatorcontrib>Park, Se-Eun</creatorcontrib><creatorcontrib>Choi, Jae Sue</creatorcontrib><creatorcontrib>Min, Byung Sun</creatorcontrib><creatorcontrib>Kim, Jeong Ah</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nguyen, Thi-Thuy An</au><au>Ha, Manh Tuan</au><au>Park, Se-Eun</au><au>Choi, Jae Sue</au><au>Min, Byung Sun</au><au>Kim, Jeong Ah</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stilbenes with Potent Protein Tyrosine Phosphatase-1B Inhibitory Activity from the Roots of Polygonum multiflorum</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2020-02-28</date><risdate>2020</risdate><volume>83</volume><issue>2</issue><spage>323</spage><epage>332</epage><pages>323-332</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Seven new stilbene glycosides including three dimers (1–3) and four monomers (4–7) were isolated from the roots of Polygonum multiflorum along with nine previously identified stilbenes (8–16). In addition, two deglucosylated stilbenes, 2a and 3a, were also obtained as new dimeric stilbenes. The structures of the purified phytochemicals were elucidated by interpreting their spectroscopic data (NMR, HRMS, and ECD). To the best of our knowledge, this represents the first isolation of a phenylpropanoid (C6–C3) substituted with a stilbene unit (7) from the Polygonaceae family. In an in vitro enzyme assay with human recombinant protein tyrosine phosphatase-1B (PTP1B), compounds 2–5 showed weak PTP1B inhibition with an IC50 value range of 27.4–37.6 μM, while three deglucosylated stilbenes 2a, 3a, and 8a exhibited IC50 values of 2.1, 1.9, and 12.1 μM, respectively. The inhibition modes and binding mechanism of selected inhibitors (2a and 3a) were investigated using kinetic methods and molecular docking simulations.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>31944695</pmid><doi>10.1021/acs.jnatprod.9b00777</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-9034-8868</orcidid><orcidid>https://orcid.org/0000-0001-7337-1812</orcidid></addata></record> |
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| subjects | Enzyme Inhibitors - chemistry Enzyme Inhibitors - isolation & purification Fallopia multiflora - chemistry Glycosides - chemistry Humans Molecular Docking Simulation Phytochemicals Plant Roots - chemistry Polygonaceae - chemistry Polygonum - chemistry Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors Protein Tyrosine Phosphatase, Non-Receptor Type 1 - chemistry Protein Tyrosine Phosphatase, Non-Receptor Type 1 - metabolism Stilbenes - chemistry Stilbenes - isolation & purification |
| title | Stilbenes with Potent Protein Tyrosine Phosphatase-1B Inhibitory Activity from the Roots of Polygonum multiflorum |
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