Facile synthesis of de-O-sulfated salacinols: Revision of the structure of neosalacinol, a potent α-glucosidase inhibitor
The structure of neosalacinol ( 8), a potent α-glucosidase inhibitor isolated recently from Ayurvedic medicine Salacia oblonga, was revised to salacinol de- O-sulfate ( 3c), by comparison of the spectroscopic properties of 8 with an authentic specimen synthesized by the coupling reaction of 9 and 10...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2009-04, Vol.19 (8), p.2195-2198 |
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| creator | Tanabe, Genzoh Xie, Weijia Ogawa, Ai Cao, Changnian Minematsu, Toshie Yoshikawa, Masayuki Muraoka, Osamu |
| description | The structure of neosalacinol (
8), a potent α-glucosidase inhibitor isolated recently from Ayurvedic medicine
Salacia oblonga, was revised to salacinol de-
O-sulfate (
3c), by comparison of the spectroscopic properties of
8 with an authentic specimen synthesized by the coupling reaction of
9 and
10.
Facile synthesis of de-O-sulfated salacinols (
3) was developed by employing the coupling reaction of an epoxide, 1,2-anhydro-3,4-di-
O-benzyl-
d-erythritol (
9) with 2,3,5-tri-
O-benzyl-1,4-dideoxy-1,4-epithio-
d-arabinitol (
10) as the key reaction. The reported structure of a potent α-glucosidase inhibitor named neosalacinol (
8), isolated recently from Ayurvedic medicine
Salacia oblonga, was proved incorrect, and revised to be de-O-sulfated salacinol formate (
3c) by comparison of the spectroscopic properties with those of the authentic specimen synthesized. Discrepancies and confusion in the literature concerning the NMR spectroscopic properties of salacinol (
1) have also been clarified. |
| doi_str_mv | 10.1016/j.bmcl.2009.02.103 |
| format | Article |
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8), a potent α-glucosidase inhibitor isolated recently from Ayurvedic medicine
Salacia oblonga, was revised to salacinol de-
O-sulfate (
3c), by comparison of the spectroscopic properties of
8 with an authentic specimen synthesized by the coupling reaction of
9 and
10.
Facile synthesis of de-O-sulfated salacinols (
3) was developed by employing the coupling reaction of an epoxide, 1,2-anhydro-3,4-di-
O-benzyl-
d-erythritol (
9) with 2,3,5-tri-
O-benzyl-1,4-dideoxy-1,4-epithio-
d-arabinitol (
10) as the key reaction. The reported structure of a potent α-glucosidase inhibitor named neosalacinol (
8), isolated recently from Ayurvedic medicine
Salacia oblonga, was proved incorrect, and revised to be de-O-sulfated salacinol formate (
3c) by comparison of the spectroscopic properties with those of the authentic specimen synthesized. Discrepancies and confusion in the literature concerning the NMR spectroscopic properties of salacinol (
1) have also been clarified.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2009.02.103</identifier><identifier>PMID: 19307117</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>alpha-Glucosidases - metabolism ; Analytical, structural and metabolic biochemistry ; Biological and medical sciences ; De-O-sulfated salacinol ; Enzymes and enzyme inhibitors ; Fundamental and applied biological sciences. Psychology ; Glycoside Hydrolase Inhibitors ; Hydrolases ; Medical sciences ; Medicine, Ayurvedic ; Miscellaneous ; Pharmacology. Drug treatments ; Plant Extracts - chemical synthesis ; Plant Extracts - isolation & purification ; Plant Extracts - pharmacology ; Plant Roots - chemistry ; Plant Stems - chemistry ; Salacia ; Salacinol ; Sugar Alcohols - chemical synthesis ; Sugar Alcohols - isolation & purification ; Sugar Alcohols - pharmacology ; Sulfates - chemical synthesis ; Sulfates - isolation & purification ; Sulfates - pharmacology ; Thiosugar ; α-Glucosidase inhibitor</subject><ispartof>Bioorganic & medicinal chemistry letters, 2009-04, Vol.19 (8), p.2195-2198</ispartof><rights>2009 Elsevier Ltd</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-64f4120d93077086f2a851a9d0cb857460843124c5afbde7d6cf57f267571bf13</citedby><cites>FETCH-LOGICAL-c415t-64f4120d93077086f2a851a9d0cb857460843124c5afbde7d6cf57f267571bf13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2009.02.103$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21391782$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19307117$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tanabe, Genzoh</creatorcontrib><creatorcontrib>Xie, Weijia</creatorcontrib><creatorcontrib>Ogawa, Ai</creatorcontrib><creatorcontrib>Cao, Changnian</creatorcontrib><creatorcontrib>Minematsu, Toshie</creatorcontrib><creatorcontrib>Yoshikawa, Masayuki</creatorcontrib><creatorcontrib>Muraoka, Osamu</creatorcontrib><title>Facile synthesis of de-O-sulfated salacinols: Revision of the structure of neosalacinol, a potent α-glucosidase inhibitor</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>The structure of neosalacinol (
8), a potent α-glucosidase inhibitor isolated recently from Ayurvedic medicine
Salacia oblonga, was revised to salacinol de-
O-sulfate (
3c), by comparison of the spectroscopic properties of
8 with an authentic specimen synthesized by the coupling reaction of
9 and
10.
Facile synthesis of de-O-sulfated salacinols (
3) was developed by employing the coupling reaction of an epoxide, 1,2-anhydro-3,4-di-
O-benzyl-
d-erythritol (
9) with 2,3,5-tri-
O-benzyl-1,4-dideoxy-1,4-epithio-
d-arabinitol (
10) as the key reaction. The reported structure of a potent α-glucosidase inhibitor named neosalacinol (
8), isolated recently from Ayurvedic medicine
Salacia oblonga, was proved incorrect, and revised to be de-O-sulfated salacinol formate (
3c) by comparison of the spectroscopic properties with those of the authentic specimen synthesized. Discrepancies and confusion in the literature concerning the NMR spectroscopic properties of salacinol (
1) have also been clarified.</description><subject>alpha-Glucosidases - metabolism</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>Biological and medical sciences</subject><subject>De-O-sulfated salacinol</subject><subject>Enzymes and enzyme inhibitors</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Glycoside Hydrolase Inhibitors</subject><subject>Hydrolases</subject><subject>Medical sciences</subject><subject>Medicine, Ayurvedic</subject><subject>Miscellaneous</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant Extracts - chemical synthesis</subject><subject>Plant Extracts - isolation & purification</subject><subject>Plant Extracts - pharmacology</subject><subject>Plant Roots - chemistry</subject><subject>Plant Stems - chemistry</subject><subject>Salacia</subject><subject>Salacinol</subject><subject>Sugar Alcohols - chemical synthesis</subject><subject>Sugar Alcohols - isolation & purification</subject><subject>Sugar Alcohols - pharmacology</subject><subject>Sulfates - chemical synthesis</subject><subject>Sulfates - isolation & purification</subject><subject>Sulfates - pharmacology</subject><subject>Thiosugar</subject><subject>α-Glucosidase inhibitor</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0cGKFDEQBuAgiruuvoAHyUVP9pik051u2YssrgoLC6LgLaSTipsh0xlT6YX1rXwRn8k0M6w3PRUUXxVF_YQ852zDGe_fbDfTzsaNYGzcMFF77QNyymUvm1ay7iE5ZWPPmmGU307IE8QtY1wyKR-TEz62THGuTsnPS2NDBIp3c7kBDEiTpw6a6waX6E0BR9HEauYU8S39DLcBQ5pXVT3FkhdblgxrY4Z0b19TQ_epwFzo71_N97jYhMEZBBrmmzCFkvJT8sibiPDsWM_I18v3Xy4-NlfXHz5dvLtqrORdaXrpJRfMrScrNvRemKHjZnTMTkOnZM8G2XIhbWf85EC53vpOedGrTvHJ8_aMvDrs3ef0YwEsehfQQoymHryg7usnhFT_h4J1rRi4rFAcoM0JMYPX-xx2Jt9pzvQajd7qNRq9RqOZqL22Dr04bl-mHbi_I8csKnh5BAatiT6b2Qa8d4K3I1eDqO784KA-7TZA1mgDzBZcyGCLdin8644_tqet4Q</recordid><startdate>20090415</startdate><enddate>20090415</enddate><creator>Tanabe, Genzoh</creator><creator>Xie, Weijia</creator><creator>Ogawa, Ai</creator><creator>Cao, Changnian</creator><creator>Minematsu, Toshie</creator><creator>Yoshikawa, Masayuki</creator><creator>Muraoka, Osamu</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><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>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20090415</creationdate><title>Facile synthesis of de-O-sulfated salacinols: Revision of the structure of neosalacinol, a potent α-glucosidase inhibitor</title><author>Tanabe, Genzoh ; Xie, Weijia ; Ogawa, Ai ; Cao, Changnian ; Minematsu, Toshie ; Yoshikawa, Masayuki ; Muraoka, Osamu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-64f4120d93077086f2a851a9d0cb857460843124c5afbde7d6cf57f267571bf13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>alpha-Glucosidases - metabolism</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>Biological and medical sciences</topic><topic>De-O-sulfated salacinol</topic><topic>Enzymes and enzyme inhibitors</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Glycoside Hydrolase Inhibitors</topic><topic>Hydrolases</topic><topic>Medical sciences</topic><topic>Medicine, Ayurvedic</topic><topic>Miscellaneous</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant Extracts - chemical synthesis</topic><topic>Plant Extracts - isolation & purification</topic><topic>Plant Extracts - pharmacology</topic><topic>Plant Roots - chemistry</topic><topic>Plant Stems - chemistry</topic><topic>Salacia</topic><topic>Salacinol</topic><topic>Sugar Alcohols - chemical synthesis</topic><topic>Sugar Alcohols - isolation & purification</topic><topic>Sugar Alcohols - pharmacology</topic><topic>Sulfates - chemical synthesis</topic><topic>Sulfates - isolation & purification</topic><topic>Sulfates - pharmacology</topic><topic>Thiosugar</topic><topic>α-Glucosidase inhibitor</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tanabe, Genzoh</creatorcontrib><creatorcontrib>Xie, Weijia</creatorcontrib><creatorcontrib>Ogawa, Ai</creatorcontrib><creatorcontrib>Cao, Changnian</creatorcontrib><creatorcontrib>Minematsu, Toshie</creatorcontrib><creatorcontrib>Yoshikawa, Masayuki</creatorcontrib><creatorcontrib>Muraoka, Osamu</creatorcontrib><collection>Pascal-Francis</collection><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>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tanabe, Genzoh</au><au>Xie, Weijia</au><au>Ogawa, Ai</au><au>Cao, Changnian</au><au>Minematsu, Toshie</au><au>Yoshikawa, Masayuki</au><au>Muraoka, Osamu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Facile synthesis of de-O-sulfated salacinols: Revision of the structure of neosalacinol, a potent α-glucosidase inhibitor</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2009-04-15</date><risdate>2009</risdate><volume>19</volume><issue>8</issue><spage>2195</spage><epage>2198</epage><pages>2195-2198</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>The structure of neosalacinol (
8), a potent α-glucosidase inhibitor isolated recently from Ayurvedic medicine
Salacia oblonga, was revised to salacinol de-
O-sulfate (
3c), by comparison of the spectroscopic properties of
8 with an authentic specimen synthesized by the coupling reaction of
9 and
10.
Facile synthesis of de-O-sulfated salacinols (
3) was developed by employing the coupling reaction of an epoxide, 1,2-anhydro-3,4-di-
O-benzyl-
d-erythritol (
9) with 2,3,5-tri-
O-benzyl-1,4-dideoxy-1,4-epithio-
d-arabinitol (
10) as the key reaction. The reported structure of a potent α-glucosidase inhibitor named neosalacinol (
8), isolated recently from Ayurvedic medicine
Salacia oblonga, was proved incorrect, and revised to be de-O-sulfated salacinol formate (
3c) by comparison of the spectroscopic properties with those of the authentic specimen synthesized. Discrepancies and confusion in the literature concerning the NMR spectroscopic properties of salacinol (
1) have also been clarified.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>19307117</pmid><doi>10.1016/j.bmcl.2009.02.103</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2009-04, Vol.19 (8), p.2195-2198 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67112471 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | alpha-Glucosidases - metabolism Analytical, structural and metabolic biochemistry Biological and medical sciences De-O-sulfated salacinol Enzymes and enzyme inhibitors Fundamental and applied biological sciences. Psychology Glycoside Hydrolase Inhibitors Hydrolases Medical sciences Medicine, Ayurvedic Miscellaneous Pharmacology. Drug treatments Plant Extracts - chemical synthesis Plant Extracts - isolation & purification Plant Extracts - pharmacology Plant Roots - chemistry Plant Stems - chemistry Salacia Salacinol Sugar Alcohols - chemical synthesis Sugar Alcohols - isolation & purification Sugar Alcohols - pharmacology Sulfates - chemical synthesis Sulfates - isolation & purification Sulfates - pharmacology Thiosugar α-Glucosidase inhibitor |
| title | Facile synthesis of de-O-sulfated salacinols: Revision of the structure of neosalacinol, a potent α-glucosidase inhibitor |
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