Four new ginkgolic acids from Ginkgo biloba
Four new compounds, 2-hydroxy-6-(12′-hydroxyheptadec-13′(E)-en-1-yl)benzoic acid (1), 2-hydroxy-6-(13′-hydroxyheptadec-11′(E)-en-1-yl)benzoic acid (2), 2-hydroxy-6-(10′-hydroxypentadec-11′(E)-en-1-yl)benzoic acid (3), and 2-hydroxy-6-(11′-hydroxypentadec-9′(E)-en-1-yl)benzoic acid (4) were isolated...
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| Veröffentlicht in: | Tetrahedron letters 2014-07, Vol.55 (28), p.3788-3791 |
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| creator | Deguchi, Jun Hasegawa, Yuki Takagi, Ayana Kutsukake, Shihoko Kono, Mizue Hirasawa, Yusuke Wong, Chin Piow Kaneda, Toshio Morita, Hiroshi |
| description | Four new compounds, 2-hydroxy-6-(12′-hydroxyheptadec-13′(E)-en-1-yl)benzoic acid (1), 2-hydroxy-6-(13′-hydroxyheptadec-11′(E)-en-1-yl)benzoic acid (2), 2-hydroxy-6-(10′-hydroxypentadec-11′(E)-en-1-yl)benzoic acid (3), and 2-hydroxy-6-(11′-hydroxypentadec-9′(E)-en-1-yl)benzoic acid (4) were isolated from the leaves of Ginkgo biloba and the structures of new ginkgolic acids were deduced on the basis of spectroscopic methods and chemical means. Compounds 1 and 2, and 3 and 4 examined as an inseparable mixture of hydroxyl and double bond positional isomers, were ultimately defined by total synthesis. Compounds 1–4 showed moderate lipid droplets accumulation inhibitory activity on mouse pre-adipocyte cell line, MC3T3-G2/PA6. |
| doi_str_mv | 10.1016/j.tetlet.2014.05.076 |
| format | Article |
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Compounds 1 and 2, and 3 and 4 examined as an inseparable mixture of hydroxyl and double bond positional isomers, were ultimately defined by total synthesis. 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Compounds 1 and 2, and 3 and 4 examined as an inseparable mixture of hydroxyl and double bond positional isomers, were ultimately defined by total synthesis. Compounds 1–4 showed moderate lipid droplets accumulation inhibitory activity on mouse pre-adipocyte cell line, MC3T3-G2/PA6.</description><subject>Biotechnology</subject><subject>Bonding</subject><subject>Droplets</subject><subject>Ginkgo biloba</subject><subject>Ginkgoaceae</subject><subject>Ginkgolic acid</subject><subject>Isomers</subject><subject>Lipids</subject><subject>Structure elucidation</subject><subject>Synthesis</subject><subject>Tetrahedrons</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNp9kE1Lw0AQhhdRsFb_gYccBUmczX7mIkixVSh40fOy2Y-yNc3W3VTx35saz85lYHjfB-ZB6BpDhQHzu201uKFzQ1UDphWwCgQ_QTMsBSkJk_gUzQAolBRIc44uct7COFzCDN0u4yEVvfsqNqF_38QumEKbYHPhU9wVq99j0YYutvoSnXndZXf1t-fobfn4ungq1y-r58XDujQU2FDaFjARXDPurXaaaS8YcBC68Y2osadOaAfQtETqxtZQE860xcRo6TW2kszRzcTdp_hxcHlQu5CN6zrdu3jICgtKuZQjc4zSKWpSzDk5r_Yp7HT6VhjU0Y3aqsmNOrpRwNToZqzdTzU3vvEZXFLZBNcbZ0NyZlA2hv8BP883bfo</recordid><startdate>20140709</startdate><enddate>20140709</enddate><creator>Deguchi, Jun</creator><creator>Hasegawa, Yuki</creator><creator>Takagi, Ayana</creator><creator>Kutsukake, Shihoko</creator><creator>Kono, Mizue</creator><creator>Hirasawa, Yusuke</creator><creator>Wong, Chin Piow</creator><creator>Kaneda, Toshio</creator><creator>Morita, Hiroshi</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20140709</creationdate><title>Four new ginkgolic acids from Ginkgo biloba</title><author>Deguchi, Jun ; Hasegawa, Yuki ; Takagi, Ayana ; Kutsukake, Shihoko ; Kono, Mizue ; Hirasawa, Yusuke ; Wong, Chin Piow ; Kaneda, Toshio ; Morita, Hiroshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c405t-db01376a56fdaea5af750607a9f9721f4e7ae009b38a9d202365ad13ca8fa1d83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Biotechnology</topic><topic>Bonding</topic><topic>Droplets</topic><topic>Ginkgo biloba</topic><topic>Ginkgoaceae</topic><topic>Ginkgolic acid</topic><topic>Isomers</topic><topic>Lipids</topic><topic>Structure elucidation</topic><topic>Synthesis</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Deguchi, Jun</creatorcontrib><creatorcontrib>Hasegawa, Yuki</creatorcontrib><creatorcontrib>Takagi, Ayana</creatorcontrib><creatorcontrib>Kutsukake, Shihoko</creatorcontrib><creatorcontrib>Kono, Mizue</creatorcontrib><creatorcontrib>Hirasawa, Yusuke</creatorcontrib><creatorcontrib>Wong, Chin Piow</creatorcontrib><creatorcontrib>Kaneda, Toshio</creatorcontrib><creatorcontrib>Morita, Hiroshi</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Deguchi, Jun</au><au>Hasegawa, Yuki</au><au>Takagi, Ayana</au><au>Kutsukake, Shihoko</au><au>Kono, Mizue</au><au>Hirasawa, Yusuke</au><au>Wong, Chin Piow</au><au>Kaneda, Toshio</au><au>Morita, Hiroshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Four new ginkgolic acids from Ginkgo biloba</atitle><jtitle>Tetrahedron letters</jtitle><date>2014-07-09</date><risdate>2014</risdate><volume>55</volume><issue>28</issue><spage>3788</spage><epage>3791</epage><pages>3788-3791</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>Four new compounds, 2-hydroxy-6-(12′-hydroxyheptadec-13′(E)-en-1-yl)benzoic acid (1), 2-hydroxy-6-(13′-hydroxyheptadec-11′(E)-en-1-yl)benzoic acid (2), 2-hydroxy-6-(10′-hydroxypentadec-11′(E)-en-1-yl)benzoic acid (3), and 2-hydroxy-6-(11′-hydroxypentadec-9′(E)-en-1-yl)benzoic acid (4) were isolated from the leaves of Ginkgo biloba and the structures of new ginkgolic acids were deduced on the basis of spectroscopic methods and chemical means. 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| ispartof | Tetrahedron letters, 2014-07, Vol.55 (28), p.3788-3791 |
| issn | 0040-4039 1873-3581 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1744688060 |
| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Biotechnology Bonding Droplets Ginkgo biloba Ginkgoaceae Ginkgolic acid Isomers Lipids Structure elucidation Synthesis Tetrahedrons |
| title | Four new ginkgolic acids from Ginkgo biloba |
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