Rare Thioglycosides from the Roots of Wasabia japonica
Six new thioglycosides (1–6) were characterized from the roots of Wasabia japonica along with a known analogue (7). Of these compounds, 1–3 possess a disulfide bridge connecting the carbohydrate motif and the aglycone, which is extremely rare in Nature. In particular, compound 1 forms an unusual 1,4...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2018-09, Vol.81 (9), p.2129-2133 |
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| container_issue | 9 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Kim, Chung Sub Oh, Joonseok Subedi, Lalita Kim, Sun Yeou Choi, Sang Un Lee, Kang Ro |
| description | Six new thioglycosides (1–6) were characterized from the roots of Wasabia japonica along with a known analogue (7). Of these compounds, 1–3 possess a disulfide bridge connecting the carbohydrate motif and the aglycone, which is extremely rare in Nature. In particular, compound 1 forms an unusual 1,4,5-oxadithiocane ring system. The structures of the isolated compounds were determined through conventional NMR and HRMS data analysis procedure, and computational methods with advanced statistics were used for the configurational assignments of 1 and two pairs of inseparable epimers, 2/3 and 4/5. All compounds were evaluated for their anti-inflammatory, neuroprotective, and cytotoxic activities, with 1 showing weak anti-inflammatory activity (IC50 41.2 μM). |
| doi_str_mv | 10.1021/acs.jnatprod.8b00570 |
| format | Article |
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Nat. Prod</addtitle><description>Six new thioglycosides (1–6) were characterized from the roots of Wasabia japonica along with a known analogue (7). Of these compounds, 1–3 possess a disulfide bridge connecting the carbohydrate motif and the aglycone, which is extremely rare in Nature. In particular, compound 1 forms an unusual 1,4,5-oxadithiocane ring system. The structures of the isolated compounds were determined through conventional NMR and HRMS data analysis procedure, and computational methods with advanced statistics were used for the configurational assignments of 1 and two pairs of inseparable epimers, 2/3 and 4/5. All compounds were evaluated for their anti-inflammatory, neuroprotective, and cytotoxic activities, with 1 showing weak anti-inflammatory activity (IC50 41.2 μM).</description><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Plant Roots - chemistry</subject><subject>Thioglycosides - chemistry</subject><subject>Thioglycosides - isolation & purification</subject><subject>Thioglycosides - pharmacology</subject><subject>Wasabia - chemistry</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kF9LwzAUxYMobk6_gUgffem8SZo0fZThPxgIY-JjuGlT19E2M2kf_PZGt_now-Vy4ZxzOT9CrinMKTB6h2WYb3scdt5Vc2UARA4nZEoFg1QCE6dkClTylCuZTchFCFsA4FCIczLhwDhTik2JXKG3yXrTuI_2q3ShqWxIau-6ZNjYZOXcEBJXJ-8Y0DSYbHHn-qbES3JWYxvs1WHPyNvjw3rxnC5fn14W98sUeaaG1KAxIKhBzsHaCmQcWxQ5LXlFRS5zKS1AQa1RpWLxrhkraKXyDEGwCviM3O5zY8vP0YZBd00obdtib90YNKM0kwXjikVptpeW3oXgba13vunQf2kK-oeYjsT0kZg-EIu2m8OH0XS2-jMdEUUB7AW_djf6Phb-P_MbHuJ5kw</recordid><startdate>20180928</startdate><enddate>20180928</enddate><creator>Kim, Chung Sub</creator><creator>Oh, Joonseok</creator><creator>Subedi, Lalita</creator><creator>Kim, Sun Yeou</creator><creator>Choi, Sang Un</creator><creator>Lee, Kang Ro</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/0000-0001-9961-4093</orcidid><orcidid>https://orcid.org/0000-0002-3725-5192</orcidid></search><sort><creationdate>20180928</creationdate><title>Rare Thioglycosides from the Roots of Wasabia japonica</title><author>Kim, Chung Sub ; Oh, Joonseok ; Subedi, Lalita ; Kim, Sun Yeou ; Choi, Sang Un ; Lee, Kang Ro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-babb051ba330eed06ed0e9971c3d1576766e0091eb8c82767f2291d874a052d03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Plant Roots - chemistry</topic><topic>Thioglycosides - chemistry</topic><topic>Thioglycosides - isolation & purification</topic><topic>Thioglycosides - pharmacology</topic><topic>Wasabia - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Chung Sub</creatorcontrib><creatorcontrib>Oh, Joonseok</creatorcontrib><creatorcontrib>Subedi, Lalita</creatorcontrib><creatorcontrib>Kim, Sun Yeou</creatorcontrib><creatorcontrib>Choi, Sang Un</creatorcontrib><creatorcontrib>Lee, Kang Ro</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>Kim, Chung Sub</au><au>Oh, Joonseok</au><au>Subedi, Lalita</au><au>Kim, Sun Yeou</au><au>Choi, Sang Un</au><au>Lee, Kang Ro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rare Thioglycosides from the Roots of Wasabia japonica</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2018-09-28</date><risdate>2018</risdate><volume>81</volume><issue>9</issue><spage>2129</spage><epage>2133</epage><pages>2129-2133</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Six new thioglycosides (1–6) were characterized from the roots of Wasabia japonica along with a known analogue (7). Of these compounds, 1–3 possess a disulfide bridge connecting the carbohydrate motif and the aglycone, which is extremely rare in Nature. In particular, compound 1 forms an unusual 1,4,5-oxadithiocane ring system. The structures of the isolated compounds were determined through conventional NMR and HRMS data analysis procedure, and computational methods with advanced statistics were used for the configurational assignments of 1 and two pairs of inseparable epimers, 2/3 and 4/5. 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| identifier | ISSN: 0163-3864 |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Anti-Inflammatory Agents - pharmacology Magnetic Resonance Spectroscopy Plant Roots - chemistry Thioglycosides - chemistry Thioglycosides - isolation & purification Thioglycosides - pharmacology Wasabia - chemistry |
| title | Rare Thioglycosides from the Roots of Wasabia japonica |
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