Two new bicyclic sulfoxides from Welsh onion
Newly identified bicyclic sulfoxides, welsonins A₁ (1) and A₂ (2), were isolated from acetone extracts of the bulbs of the Welsh onion (Allium fistulosum). In this study, the structures of 1 and 2, which are tetrahydrothiophene-S-oxide derivatives, were characterized by spectroscopic analysis. These...
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| Veröffentlicht in: | Journal of natural medicines 2016-04, Vol.70 (2), p.260-265 |
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| container_title | Journal of natural medicines |
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| creator | Nohara, Toshihiro Fujiwara, Yukio Ikeda, Tsuyoshi Murakami, Kotaro Ono, Masateru El-Aasr, Mona Nakano, Daisuke Kinjo, Junei |
| description | Newly identified bicyclic sulfoxides, welsonins A₁ (1) and A₂ (2), were isolated from acetone extracts of the bulbs of the Welsh onion (Allium fistulosum). In this study, the structures of 1 and 2, which are tetrahydrothiophene-S-oxide derivatives, were characterized by spectroscopic analysis. These compounds appeared to be derived from the coupling of 1-propenyl sulfenic acid and uronic acid. Welsonin A₁ (1) showed the potential to suppress tumor-cell proliferation by inhibiting the polarization of alternatively activated M2 macrophages. |
| doi_str_mv | 10.1007/s11418-015-0947-z |
| format | Article |
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In this study, the structures of 1 and 2, which are tetrahydrothiophene-S-oxide derivatives, were characterized by spectroscopic analysis. These compounds appeared to be derived from the coupling of 1-propenyl sulfenic acid and uronic acid. Welsonin A₁ (1) showed the potential to suppress tumor-cell proliferation by inhibiting the polarization of alternatively activated M2 macrophages.</description><identifier>ISSN: 1340-3443</identifier><identifier>EISSN: 1861-0293</identifier><identifier>DOI: 10.1007/s11418-015-0947-z</identifier><identifier>PMID: 26676612</identifier><language>eng</language><publisher>Tokyo: Springer Japan</publisher><subject>acetone ; Allium fistulosum ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Biomedical and Life Sciences ; Biomedicine ; bulbs ; Cell Line ; Cell Proliferation - drug effects ; Complementary & Alternative Medicine ; Humans ; Japanese bunching onions ; macrophages ; Macrophages - drug effects ; Medicinal Chemistry ; neoplasm cells ; Neoplasms ; Onions - chemistry ; Pharmacology/Toxicology ; Pharmacy ; Plant Extracts - chemistry ; Plant Extracts - pharmacology ; Plant Roots - chemistry ; Plant Sciences ; spectroscopy ; Sulfoxides - chemistry ; Sulfoxides - isolation & purification ; Sulfoxides - pharmacology ; Thiophenes - analysis ; uronic acids</subject><ispartof>Journal of natural medicines, 2016-04, Vol.70 (2), p.260-265</ispartof><rights>The Japanese Society of Pharmacognosy and Springer Japan 2015</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c555t-f09e9695a0c345bce7e2c162cfdf2a7c6f266484c0222b379d3c90f2307192193</citedby><cites>FETCH-LOGICAL-c555t-f09e9695a0c345bce7e2c162cfdf2a7c6f266484c0222b379d3c90f2307192193</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11418-015-0947-z$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11418-015-0947-z$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27903,27904,41467,42536,51297</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26676612$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nohara, Toshihiro</creatorcontrib><creatorcontrib>Fujiwara, Yukio</creatorcontrib><creatorcontrib>Ikeda, Tsuyoshi</creatorcontrib><creatorcontrib>Murakami, Kotaro</creatorcontrib><creatorcontrib>Ono, Masateru</creatorcontrib><creatorcontrib>El-Aasr, Mona</creatorcontrib><creatorcontrib>Nakano, Daisuke</creatorcontrib><creatorcontrib>Kinjo, Junei</creatorcontrib><title>Two new bicyclic sulfoxides from Welsh onion</title><title>Journal of natural medicines</title><addtitle>J Nat Med</addtitle><addtitle>J Nat Med</addtitle><description>Newly identified bicyclic sulfoxides, welsonins A₁ (1) and A₂ (2), were isolated from acetone extracts of the bulbs of the Welsh onion (Allium fistulosum). In this study, the structures of 1 and 2, which are tetrahydrothiophene-S-oxide derivatives, were characterized by spectroscopic analysis. These compounds appeared to be derived from the coupling of 1-propenyl sulfenic acid and uronic acid. Welsonin A₁ (1) showed the potential to suppress tumor-cell proliferation by inhibiting the polarization of alternatively activated M2 macrophages.</description><subject>acetone</subject><subject>Allium fistulosum</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>bulbs</subject><subject>Cell Line</subject><subject>Cell Proliferation - drug effects</subject><subject>Complementary & Alternative Medicine</subject><subject>Humans</subject><subject>Japanese bunching onions</subject><subject>macrophages</subject><subject>Macrophages - drug effects</subject><subject>Medicinal Chemistry</subject><subject>neoplasm cells</subject><subject>Neoplasms</subject><subject>Onions - chemistry</subject><subject>Pharmacology/Toxicology</subject><subject>Pharmacy</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - pharmacology</subject><subject>Plant Roots - chemistry</subject><subject>Plant Sciences</subject><subject>spectroscopy</subject><subject>Sulfoxides - chemistry</subject><subject>Sulfoxides - isolation & purification</subject><subject>Sulfoxides - pharmacology</subject><subject>Thiophenes - analysis</subject><subject>uronic acids</subject><issn>1340-3443</issn><issn>1861-0293</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMtOwzAQRS0EoqXwAWwgSxYEZvxKvUQVL6kSC4pYWqljl1RJXGyiAl-PUYAlK4_kc-9oDiHHCBcIUFxGRI7THFDkoHiRf-6QMU4l5kAV200z45AzztmIHMS4BuCUMdwnIyplISXSMTlfbH3W2W22rM2HaWqTxb5x_r2ubMxc8G32bJv4kvmu9t0h2XNlE-3RzzshTzfXi9ldPn-4vZ9dzXMjhHjLHSirpBIlGMbF0tjCUoOSGlc5WhZGurSfT7kBSumSFapiRoGjDApUFBWbkLOhdxP8a2_jm27raGzTlJ31fdRYSKEoRS4SigNqgo8xWKc3oW7L8KER9LckPUjSSZL-lqQ_U-bkp75ftrb6S_xaSQAdgJi-upUNeu370KWT_209HUKu9LpchTrqp0cKKCHxijHBvgAtj3my</recordid><startdate>20160401</startdate><enddate>20160401</enddate><creator>Nohara, Toshihiro</creator><creator>Fujiwara, Yukio</creator><creator>Ikeda, Tsuyoshi</creator><creator>Murakami, Kotaro</creator><creator>Ono, Masateru</creator><creator>El-Aasr, Mona</creator><creator>Nakano, Daisuke</creator><creator>Kinjo, Junei</creator><general>Springer Japan</general><scope>FBQ</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>7X8</scope></search><sort><creationdate>20160401</creationdate><title>Two new bicyclic sulfoxides from Welsh onion</title><author>Nohara, Toshihiro ; Fujiwara, Yukio ; Ikeda, Tsuyoshi ; Murakami, Kotaro ; Ono, Masateru ; El-Aasr, Mona ; Nakano, Daisuke ; Kinjo, Junei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c555t-f09e9695a0c345bce7e2c162cfdf2a7c6f266484c0222b379d3c90f2307192193</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>acetone</topic><topic>Allium fistulosum</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>bulbs</topic><topic>Cell Line</topic><topic>Cell Proliferation - drug effects</topic><topic>Complementary & Alternative Medicine</topic><topic>Humans</topic><topic>Japanese bunching onions</topic><topic>macrophages</topic><topic>Macrophages - drug effects</topic><topic>Medicinal Chemistry</topic><topic>neoplasm cells</topic><topic>Neoplasms</topic><topic>Onions - chemistry</topic><topic>Pharmacology/Toxicology</topic><topic>Pharmacy</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - pharmacology</topic><topic>Plant Roots - chemistry</topic><topic>Plant Sciences</topic><topic>spectroscopy</topic><topic>Sulfoxides - chemistry</topic><topic>Sulfoxides - isolation & purification</topic><topic>Sulfoxides - pharmacology</topic><topic>Thiophenes - analysis</topic><topic>uronic acids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nohara, Toshihiro</creatorcontrib><creatorcontrib>Fujiwara, Yukio</creatorcontrib><creatorcontrib>Ikeda, Tsuyoshi</creatorcontrib><creatorcontrib>Murakami, Kotaro</creatorcontrib><creatorcontrib>Ono, Masateru</creatorcontrib><creatorcontrib>El-Aasr, Mona</creatorcontrib><creatorcontrib>Nakano, Daisuke</creatorcontrib><creatorcontrib>Kinjo, Junei</creatorcontrib><collection>AGRIS</collection><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 medicines</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nohara, Toshihiro</au><au>Fujiwara, Yukio</au><au>Ikeda, Tsuyoshi</au><au>Murakami, Kotaro</au><au>Ono, Masateru</au><au>El-Aasr, Mona</au><au>Nakano, Daisuke</au><au>Kinjo, Junei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Two new bicyclic sulfoxides from Welsh onion</atitle><jtitle>Journal of natural medicines</jtitle><stitle>J Nat Med</stitle><addtitle>J Nat Med</addtitle><date>2016-04-01</date><risdate>2016</risdate><volume>70</volume><issue>2</issue><spage>260</spage><epage>265</epage><pages>260-265</pages><issn>1340-3443</issn><eissn>1861-0293</eissn><abstract>Newly identified bicyclic sulfoxides, welsonins A₁ (1) and A₂ (2), were isolated from acetone extracts of the bulbs of the Welsh onion (Allium fistulosum). In this study, the structures of 1 and 2, which are tetrahydrothiophene-S-oxide derivatives, were characterized by spectroscopic analysis. These compounds appeared to be derived from the coupling of 1-propenyl sulfenic acid and uronic acid. Welsonin A₁ (1) showed the potential to suppress tumor-cell proliferation by inhibiting the polarization of alternatively activated M2 macrophages.</abstract><cop>Tokyo</cop><pub>Springer Japan</pub><pmid>26676612</pmid><doi>10.1007/s11418-015-0947-z</doi><tpages>6</tpages></addata></record> |
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| subjects | acetone Allium fistulosum Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Biomedical and Life Sciences Biomedicine bulbs Cell Line Cell Proliferation - drug effects Complementary & Alternative Medicine Humans Japanese bunching onions macrophages Macrophages - drug effects Medicinal Chemistry neoplasm cells Neoplasms Onions - chemistry Pharmacology/Toxicology Pharmacy Plant Extracts - chemistry Plant Extracts - pharmacology Plant Roots - chemistry Plant Sciences spectroscopy Sulfoxides - chemistry Sulfoxides - isolation & purification Sulfoxides - pharmacology Thiophenes - analysis uronic acids |
| title | Two new bicyclic sulfoxides from Welsh onion |
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