New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of <i>Aster koraiensis</i>
Four new eudesmane-type sesquiterpenoids, (1<i>R</i>,5<i>S</i>,6<i>R</i>,7<i>S</i>,9<i>S</i>,10<i>S</i>)-1,6,9-trihydroxy-eudesm-3-ene-1,6-di-<i>O</i>-<i>β</i>-<span style="font-variant: small-cap...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-12-01
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| Series: | Plants |
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| Online Access: | https://www.mdpi.com/2223-7747/9/12/1811 |
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| author | Ji-Young Kim Young Hye Seo Im-Ho Lee He Yun Choi Hak Cheol Kwon Jung-Hye Choi Jun Lee Dae Sik Jang |
| author_facet | Ji-Young Kim Young Hye Seo Im-Ho Lee He Yun Choi Hak Cheol Kwon Jung-Hye Choi Jun Lee Dae Sik Jang |
| author_sort | Ji-Young Kim |
| collection | DOAJ |
| description | Four new eudesmane-type sesquiterpenoids, (1<i>R</i>,5<i>S</i>,6<i>R</i>,7<i>S</i>,9<i>S</i>,10<i>S</i>)-1,6,9-trihydroxy-eudesm-3-ene-1,6-di-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>1</b>), (1<i>R</i>,5<i>S</i>,6S,7<i>R</i>,9<i>S</i>,10<i>S</i>)-1,6,9,11-tetrahydroxy-eudesm-3-ene-1,6-di-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>3</b>), (1<i>R</i>,5<i>S</i>,6<i>R</i>,7<i>S</i>,9<i>S</i>,10<i>R</i>)-9-<i>O</i>-(<i>Z</i>-<i>p</i>-coumaroyl)-1,6,9-trihydroxy-eudesm-3-ene-6-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>6</b>), and (1<i>R</i>,5<i>S</i>,6<i>R</i>,7<i>S</i>,9<i>S</i>,10<i>R</i>)-9-<i>O</i>-(<i>E</i>-feruloyl)-1,6,9-trihydroxy-eudesm-3-ene-6-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>7</b>), were isolated from a 95% EtOH extract of the leaves of <i>Aster koraiensis</i> by repeated chromatography. Moreover, three sesquiterpenoids (<b>2</b>, <b>4</b>, and <b>5</b>) and two caffeoylquinic acids (<b>8</b> and <b>9</b>) having previously known chemical structures were isolated during the isolation procedure. The four new compounds (<b>1</b>, <b>3</b>, <b>6</b>, and <b>7</b>) were elucidated by spectroscopic data (1D- and 2D-NMR, MS, and ECD) interpretation and hydrolysis. Moreover, the absolute configurations of <b>2</b>, <b>4</b>, and <b>5</b> were determined for the first time in this study. The compounds isolated were tested for their viability on nitric oxide (NO) and prostaglandin E<sub>2</sub> (PGE<sub>2</sub>) production on LPS-stimulated RAW 264.7 cells. Among them, only <b>7</b> presented weak inhibitory effects on both NO and PGE<sub>2</sub> production. |
| first_indexed | 2024-03-10T13:53:51Z |
| format | Article |
| id | doaj.art-feb6a60eb3bf4dfd857ede8a33e2aeb8 |
| institution | Directory Open Access Journal |
| issn | 2223-7747 |
| language | English |
| last_indexed | 2024-03-10T13:53:51Z |
| publishDate | 2020-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Plants |
| spelling | doaj.art-feb6a60eb3bf4dfd857ede8a33e2aeb82023-11-21T01:52:25ZengMDPI AGPlants2223-77472020-12-01912181110.3390/plants9121811New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of <i>Aster koraiensis</i>Ji-Young Kim0Young Hye Seo1Im-Ho Lee2He Yun Choi3Hak Cheol Kwon4Jung-Hye Choi5Jun Lee6Dae Sik Jang7Department of Life and Nanopharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, KoreaHerbal Medicine Resources Research Center, Korea Institute of Oriental Medicine (KIOM), Naju 58245, KoreaDepartment of Life and Nanopharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, KoreaDepartment of Life and Nanopharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, KoreaNatural Product Informatics Research Center, Korea Institute of Science and Technology (KIST) Gangneung Institute, Gangneung 25451, KoreaDepartment of Life and Nanopharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, KoreaHerbal Medicine Resources Research Center, Korea Institute of Oriental Medicine (KIOM), Naju 58245, KoreaDepartment of Life and Nanopharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, KoreaFour new eudesmane-type sesquiterpenoids, (1<i>R</i>,5<i>S</i>,6<i>R</i>,7<i>S</i>,9<i>S</i>,10<i>S</i>)-1,6,9-trihydroxy-eudesm-3-ene-1,6-di-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>1</b>), (1<i>R</i>,5<i>S</i>,6S,7<i>R</i>,9<i>S</i>,10<i>S</i>)-1,6,9,11-tetrahydroxy-eudesm-3-ene-1,6-di-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>3</b>), (1<i>R</i>,5<i>S</i>,6<i>R</i>,7<i>S</i>,9<i>S</i>,10<i>R</i>)-9-<i>O</i>-(<i>Z</i>-<i>p</i>-coumaroyl)-1,6,9-trihydroxy-eudesm-3-ene-6-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>6</b>), and (1<i>R</i>,5<i>S</i>,6<i>R</i>,7<i>S</i>,9<i>S</i>,10<i>R</i>)-9-<i>O</i>-(<i>E</i>-feruloyl)-1,6,9-trihydroxy-eudesm-3-ene-6-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>7</b>), were isolated from a 95% EtOH extract of the leaves of <i>Aster koraiensis</i> by repeated chromatography. Moreover, three sesquiterpenoids (<b>2</b>, <b>4</b>, and <b>5</b>) and two caffeoylquinic acids (<b>8</b> and <b>9</b>) having previously known chemical structures were isolated during the isolation procedure. The four new compounds (<b>1</b>, <b>3</b>, <b>6</b>, and <b>7</b>) were elucidated by spectroscopic data (1D- and 2D-NMR, MS, and ECD) interpretation and hydrolysis. Moreover, the absolute configurations of <b>2</b>, <b>4</b>, and <b>5</b> were determined for the first time in this study. The compounds isolated were tested for their viability on nitric oxide (NO) and prostaglandin E<sub>2</sub> (PGE<sub>2</sub>) production on LPS-stimulated RAW 264.7 cells. Among them, only <b>7</b> presented weak inhibitory effects on both NO and PGE<sub>2</sub> production.https://www.mdpi.com/2223-7747/9/12/1811<i>Aster koraiensis</i>Compositaesesquiterpenoidsdicaffeoylquinic acidsnitric oxideprostaglandin E<sub>2</sub> |
| spellingShingle | Ji-Young Kim Young Hye Seo Im-Ho Lee He Yun Choi Hak Cheol Kwon Jung-Hye Choi Jun Lee Dae Sik Jang New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of <i>Aster koraiensis</i> Plants <i>Aster koraiensis</i> Compositae sesquiterpenoids dicaffeoylquinic acids nitric oxide prostaglandin E<sub>2</sub> |
| title | New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of <i>Aster koraiensis</i> |
| title_full | New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of <i>Aster koraiensis</i> |
| title_fullStr | New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of <i>Aster koraiensis</i> |
| title_full_unstemmed | New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of <i>Aster koraiensis</i> |
| title_short | New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of <i>Aster koraiensis</i> |
| title_sort | new eudesmane type sesquiterpene glycosides from the leaves of i aster koraiensis i |
| topic | <i>Aster koraiensis</i> Compositae sesquiterpenoids dicaffeoylquinic acids nitric oxide prostaglandin E<sub>2</sub> |
| url | https://www.mdpi.com/2223-7747/9/12/1811 |
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