α‑Glucosidase Inhibitors from Malbranchea flavorosea
From an extract prepared from the grain-based culture of Malbranchea flavorosea two new polyketides, namely, 8-chloroxylarinol A (1) and flavoroseoside (2), along with the known compounds xylarinol A (3), xylarinol B (4), massarigenins B and C (5 and 6), and clavatol (7), were isolated. The structur...
Gespeichert in:
| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2017-01, Vol.80 (1), p.190-195 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 195 |
|---|---|
| container_issue | 1 |
| container_start_page | 190 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 80 |
| creator | Verastegui-Omaña, Brisa Rebollar-Ramos, Daniela Pérez-Vásquez, Araceli Martínez, Ana Laura Madariaga-Mazón, Abraham Flores-Bocanegra, Laura Mata, Rachel |
| description | From an extract prepared from the grain-based culture of Malbranchea flavorosea two new polyketides, namely, 8-chloroxylarinol A (1) and flavoroseoside (2), along with the known compounds xylarinol A (3), xylarinol B (4), massarigenins B and C (5 and 6), and clavatol (7), were isolated. The structures of 1 and 2 were elucidated using spectroscopic methods and corroborated by single-crystal X-ray diffraction analysis. In the case of compound 2 the absolute configuration at the stereogenic centers was established according to the method of Flack. In addition, the X-ray structure of compound 6 is reported for the first time. Compounds 3, 4, and 6 significantly inhibited yeast α-glucosidase. Compound 6 also inhibited the postprandial peak during an oral sucrose tolerance assay when tested in vivo, using normal and NA/STZ-induced hyperglycemic mice. |
| doi_str_mv | 10.1021/acs.jnatprod.6b00977 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1856589267</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1856589267</sourcerecordid><originalsourceid>FETCH-LOGICAL-a348t-f169520ef5bca739e620f6a02ca0ddd1f6fb714d20c74f0ae7cb93d765a119203</originalsourceid><addsrcrecordid>eNp9kE1OwzAUhC0EoqVwA4SyZJPy7MR2skQVlEpFbGAdvfhHTZWfYidI7LgCR-EiHIKTYGjLktXbzMyb-Qg5pzClwOgVKj9dt9hvXKenogTIpTwgY8oZxAIYPyRjoCKJk0ykI3Li_RoAEsj5MRmxDARw4GMiPz--3t7n9aA6X2n0Jlq0q6qs-s75yLquie6xLh22amUwsjW-dK7zBk_JkcXam7PdnZCn25vH2V28fJgvZtfLGJM062NLRR4KGctLhTLJjWBgBQJTCFpraoUtJU01AyVTC2ikKvNES8GR0pxBMiGX29ww83kwvi-ayitT19iabvAFzbjgWc6EDNJ0K1WhoXfGFhtXNeheCwrFD7IiICv2yIodsmC72H0YysboP9OeURDAVvBr7wbXhsH_Z34DOpd9Fw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1856589267</pqid></control><display><type>article</type><title>α‑Glucosidase Inhibitors from Malbranchea flavorosea</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Verastegui-Omaña, Brisa ; Rebollar-Ramos, Daniela ; Pérez-Vásquez, Araceli ; Martínez, Ana Laura ; Madariaga-Mazón, Abraham ; Flores-Bocanegra, Laura ; Mata, Rachel</creator><creatorcontrib>Verastegui-Omaña, Brisa ; Rebollar-Ramos, Daniela ; Pérez-Vásquez, Araceli ; Martínez, Ana Laura ; Madariaga-Mazón, Abraham ; Flores-Bocanegra, Laura ; Mata, Rachel</creatorcontrib><description>From an extract prepared from the grain-based culture of Malbranchea flavorosea two new polyketides, namely, 8-chloroxylarinol A (1) and flavoroseoside (2), along with the known compounds xylarinol A (3), xylarinol B (4), massarigenins B and C (5 and 6), and clavatol (7), were isolated. The structures of 1 and 2 were elucidated using spectroscopic methods and corroborated by single-crystal X-ray diffraction analysis. In the case of compound 2 the absolute configuration at the stereogenic centers was established according to the method of Flack. In addition, the X-ray structure of compound 6 is reported for the first time. Compounds 3, 4, and 6 significantly inhibited yeast α-glucosidase. Compound 6 also inhibited the postprandial peak during an oral sucrose tolerance assay when tested in vivo, using normal and NA/STZ-induced hyperglycemic mice.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/acs.jnatprod.6b00977</identifier><identifier>PMID: 28060505</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Animals ; Benzoxepins - chemistry ; Benzoxepins - isolation & purification ; Benzoxepins - pharmacology ; Glycoside Hydrolase Inhibitors - chemistry ; Glycoside Hydrolase Inhibitors - isolation & purification ; Glycoside Hydrolase Inhibitors - pharmacology ; Hypoglycemic Agents - chemistry ; Hypoglycemic Agents - metabolism ; Lactones - chemistry ; Lactones - isolation & purification ; Lactones - pharmacology ; Magnetic Resonance Spectroscopy ; Mice ; Molecular Structure ; Polyketides - chemistry ; Polyketides - isolation & purification ; Polyketides - pharmacology ; Spiro Compounds - chemistry ; Spiro Compounds - isolation & purification ; Spiro Compounds - pharmacology ; X-Ray Diffraction</subject><ispartof>Journal of natural products (Washington, D.C.), 2017-01, Vol.80 (1), p.190-195</ispartof><rights>Copyright © 2017 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-f169520ef5bca739e620f6a02ca0ddd1f6fb714d20c74f0ae7cb93d765a119203</citedby><cites>FETCH-LOGICAL-a348t-f169520ef5bca739e620f6a02ca0ddd1f6fb714d20c74f0ae7cb93d765a119203</cites><orcidid>0000-0002-2861-2768</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.6b00977$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jnatprod.6b00977$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28060505$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Verastegui-Omaña, Brisa</creatorcontrib><creatorcontrib>Rebollar-Ramos, Daniela</creatorcontrib><creatorcontrib>Pérez-Vásquez, Araceli</creatorcontrib><creatorcontrib>Martínez, Ana Laura</creatorcontrib><creatorcontrib>Madariaga-Mazón, Abraham</creatorcontrib><creatorcontrib>Flores-Bocanegra, Laura</creatorcontrib><creatorcontrib>Mata, Rachel</creatorcontrib><title>α‑Glucosidase Inhibitors from Malbranchea flavorosea</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>From an extract prepared from the grain-based culture of Malbranchea flavorosea two new polyketides, namely, 8-chloroxylarinol A (1) and flavoroseoside (2), along with the known compounds xylarinol A (3), xylarinol B (4), massarigenins B and C (5 and 6), and clavatol (7), were isolated. The structures of 1 and 2 were elucidated using spectroscopic methods and corroborated by single-crystal X-ray diffraction analysis. In the case of compound 2 the absolute configuration at the stereogenic centers was established according to the method of Flack. In addition, the X-ray structure of compound 6 is reported for the first time. Compounds 3, 4, and 6 significantly inhibited yeast α-glucosidase. Compound 6 also inhibited the postprandial peak during an oral sucrose tolerance assay when tested in vivo, using normal and NA/STZ-induced hyperglycemic mice.</description><subject>Animals</subject><subject>Benzoxepins - chemistry</subject><subject>Benzoxepins - isolation & purification</subject><subject>Benzoxepins - pharmacology</subject><subject>Glycoside Hydrolase Inhibitors - chemistry</subject><subject>Glycoside Hydrolase Inhibitors - isolation & purification</subject><subject>Glycoside Hydrolase Inhibitors - pharmacology</subject><subject>Hypoglycemic Agents - chemistry</subject><subject>Hypoglycemic Agents - metabolism</subject><subject>Lactones - chemistry</subject><subject>Lactones - isolation & purification</subject><subject>Lactones - pharmacology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Polyketides - chemistry</subject><subject>Polyketides - isolation & purification</subject><subject>Polyketides - pharmacology</subject><subject>Spiro Compounds - chemistry</subject><subject>Spiro Compounds - isolation & purification</subject><subject>Spiro Compounds - pharmacology</subject><subject>X-Ray Diffraction</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1OwzAUhC0EoqVwA4SyZJPy7MR2skQVlEpFbGAdvfhHTZWfYidI7LgCR-EiHIKTYGjLktXbzMyb-Qg5pzClwOgVKj9dt9hvXKenogTIpTwgY8oZxAIYPyRjoCKJk0ykI3Li_RoAEsj5MRmxDARw4GMiPz--3t7n9aA6X2n0Jlq0q6qs-s75yLquie6xLh22amUwsjW-dK7zBk_JkcXam7PdnZCn25vH2V28fJgvZtfLGJM062NLRR4KGctLhTLJjWBgBQJTCFpraoUtJU01AyVTC2ikKvNES8GR0pxBMiGX29ww83kwvi-ayitT19iabvAFzbjgWc6EDNJ0K1WhoXfGFhtXNeheCwrFD7IiICv2yIodsmC72H0YysboP9OeURDAVvBr7wbXhsH_Z34DOpd9Fw</recordid><startdate>20170127</startdate><enddate>20170127</enddate><creator>Verastegui-Omaña, Brisa</creator><creator>Rebollar-Ramos, Daniela</creator><creator>Pérez-Vásquez, Araceli</creator><creator>Martínez, Ana Laura</creator><creator>Madariaga-Mazón, Abraham</creator><creator>Flores-Bocanegra, Laura</creator><creator>Mata, Rachel</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/0000-0002-2861-2768</orcidid></search><sort><creationdate>20170127</creationdate><title>α‑Glucosidase Inhibitors from Malbranchea flavorosea</title><author>Verastegui-Omaña, Brisa ; Rebollar-Ramos, Daniela ; Pérez-Vásquez, Araceli ; Martínez, Ana Laura ; Madariaga-Mazón, Abraham ; Flores-Bocanegra, Laura ; Mata, Rachel</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-f169520ef5bca739e620f6a02ca0ddd1f6fb714d20c74f0ae7cb93d765a119203</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Animals</topic><topic>Benzoxepins - chemistry</topic><topic>Benzoxepins - isolation & purification</topic><topic>Benzoxepins - pharmacology</topic><topic>Glycoside Hydrolase Inhibitors - chemistry</topic><topic>Glycoside Hydrolase Inhibitors - isolation & purification</topic><topic>Glycoside Hydrolase Inhibitors - pharmacology</topic><topic>Hypoglycemic Agents - chemistry</topic><topic>Hypoglycemic Agents - metabolism</topic><topic>Lactones - chemistry</topic><topic>Lactones - isolation & purification</topic><topic>Lactones - pharmacology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Polyketides - chemistry</topic><topic>Polyketides - isolation & purification</topic><topic>Polyketides - pharmacology</topic><topic>Spiro Compounds - chemistry</topic><topic>Spiro Compounds - isolation & purification</topic><topic>Spiro Compounds - pharmacology</topic><topic>X-Ray Diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Verastegui-Omaña, Brisa</creatorcontrib><creatorcontrib>Rebollar-Ramos, Daniela</creatorcontrib><creatorcontrib>Pérez-Vásquez, Araceli</creatorcontrib><creatorcontrib>Martínez, Ana Laura</creatorcontrib><creatorcontrib>Madariaga-Mazón, Abraham</creatorcontrib><creatorcontrib>Flores-Bocanegra, Laura</creatorcontrib><creatorcontrib>Mata, Rachel</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>Verastegui-Omaña, Brisa</au><au>Rebollar-Ramos, Daniela</au><au>Pérez-Vásquez, Araceli</au><au>Martínez, Ana Laura</au><au>Madariaga-Mazón, Abraham</au><au>Flores-Bocanegra, Laura</au><au>Mata, Rachel</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>α‑Glucosidase Inhibitors from Malbranchea flavorosea</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2017-01-27</date><risdate>2017</risdate><volume>80</volume><issue>1</issue><spage>190</spage><epage>195</epage><pages>190-195</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>From an extract prepared from the grain-based culture of Malbranchea flavorosea two new polyketides, namely, 8-chloroxylarinol A (1) and flavoroseoside (2), along with the known compounds xylarinol A (3), xylarinol B (4), massarigenins B and C (5 and 6), and clavatol (7), were isolated. The structures of 1 and 2 were elucidated using spectroscopic methods and corroborated by single-crystal X-ray diffraction analysis. In the case of compound 2 the absolute configuration at the stereogenic centers was established according to the method of Flack. In addition, the X-ray structure of compound 6 is reported for the first time. Compounds 3, 4, and 6 significantly inhibited yeast α-glucosidase. Compound 6 also inhibited the postprandial peak during an oral sucrose tolerance assay when tested in vivo, using normal and NA/STZ-induced hyperglycemic mice.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>28060505</pmid><doi>10.1021/acs.jnatprod.6b00977</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-2861-2768</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2017-01, Vol.80 (1), p.190-195 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1856589267 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Animals Benzoxepins - chemistry Benzoxepins - isolation & purification Benzoxepins - pharmacology Glycoside Hydrolase Inhibitors - chemistry Glycoside Hydrolase Inhibitors - isolation & purification Glycoside Hydrolase Inhibitors - pharmacology Hypoglycemic Agents - chemistry Hypoglycemic Agents - metabolism Lactones - chemistry Lactones - isolation & purification Lactones - pharmacology Magnetic Resonance Spectroscopy Mice Molecular Structure Polyketides - chemistry Polyketides - isolation & purification Polyketides - pharmacology Spiro Compounds - chemistry Spiro Compounds - isolation & purification Spiro Compounds - pharmacology X-Ray Diffraction |
| title | α‑Glucosidase Inhibitors from Malbranchea flavorosea |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-26T05%3A12%3A34IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=%CE%B1%E2%80%91Glucosidase%20Inhibitors%20from%20Malbranchea%20flavorosea&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Verastegui-Oman%CC%83a,%20Brisa&rft.date=2017-01-27&rft.volume=80&rft.issue=1&rft.spage=190&rft.epage=195&rft.pages=190-195&rft.issn=0163-3864&rft.eissn=1520-6025&rft_id=info:doi/10.1021/acs.jnatprod.6b00977&rft_dat=%3Cproquest_cross%3E1856589267%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1856589267&rft_id=info:pmid/28060505&rfr_iscdi=true |