Isolation of Unstable Isomers of Lucilactaene and Evaluation of Anti-Inflammatory Activity of Secondary Metabolites Produced by the Endophytic Fungus <i>Fusarium</i> sp. QF001 from the Roots of <i>Scutellaria baicalensis</i>
The filamentous fungal pathogen <i>Fusarium</i> sp. causes several crop diseases. Some <i>Fusarium</i> sp. are endophytes that produce diverse valuable bioactive secondary metabolites. Here, extensive chemical investigation of the endophytic fungus, <i>Fusarium</i>...
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MDPI AG
2020-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/4/923 |
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| author | Sailesh Maharjan Sang Bong Lee Geum Jin Kim Sung Jin Cho Joo-Won Nam Jungwook Chin Hyukjae Choi |
| author_facet | Sailesh Maharjan Sang Bong Lee Geum Jin Kim Sung Jin Cho Joo-Won Nam Jungwook Chin Hyukjae Choi |
| author_sort | Sailesh Maharjan |
| collection | DOAJ |
| description | The filamentous fungal pathogen <i>Fusarium</i> sp. causes several crop diseases. Some <i>Fusarium</i> sp. are endophytes that produce diverse valuable bioactive secondary metabolites. Here, extensive chemical investigation of the endophytic fungus, <i>Fusarium</i> sp. QF001, isolated from the inner rotten part of old roots of <i>Scutellariae baicalensis</i> resulted in the isolation of two new photosensitive geometrical isomers of lucilactaene (compounds <b>2</b> and <b>3</b>) along with lucilactaene (<b>6</b>) and six other known compounds (fusarubin (<b>1</b>), (+)-solaniol (<b>4</b>), javanicin (<b>5</b>), 9-desmethylherbarine (<b>7</b>), NG391 (<b>8</b>) and NG393 (<b>9</b>)). Newly isolated isomers and lucilactaene were unstable under light at room temperature and tended to be a mixture in equilibrium state when exposed to a polar protic solvent during reversed phase chromatography. Normal phase chromatography under dim light conditions with an aprotic mobile phase led to the successful isolation of the relatively unstable isomers <b>2</b> and <b>3</b>. Their structures were elucidated as 8(Z)-lucilactaene (<b>2</b>) and 4(<i>Z</i>)-lucilactaene (<b>3</b>) based on spectroscopic data. The absolute configuration of <b>4</b> was speculated to be <i>R</i> by computer-assisted specific rotation analysis. The isolated compounds could inhibit NO production and suppress pro-inflammatory cytokines expression in LPS-stimulated macrophage cells. These properties of the isolated compounds indicate their potential use as anti-inflammatory drugs. |
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| language | English |
| last_indexed | 2024-12-12T20:26:27Z |
| publishDate | 2020-02-01 |
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| series | Molecules |
| spelling | doaj.art-63b2e2f1fd7d4ade9200d9c4aff75e182022-12-22T00:13:08ZengMDPI AGMolecules1420-30492020-02-0125492310.3390/molecules25040923molecules25040923Isolation of Unstable Isomers of Lucilactaene and Evaluation of Anti-Inflammatory Activity of Secondary Metabolites Produced by the Endophytic Fungus <i>Fusarium</i> sp. QF001 from the Roots of <i>Scutellaria baicalensis</i>Sailesh Maharjan0Sang Bong Lee1Geum Jin Kim2Sung Jin Cho3Joo-Won Nam4Jungwook Chin5Hyukjae Choi6College of Pharmacy, Yeungnam University, Gyeongsan 38541, KoreaKorea Institute of Medical Microrobotics, Gwangju 61011, KoreaCollege of Pharmacy, Yeungnam University, Gyeongsan 38541, KoreaNew Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation, Daegu 41061, KoreaCollege of Pharmacy, Yeungnam University, Gyeongsan 38541, KoreaNew Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation, Daegu 41061, KoreaCollege of Pharmacy, Yeungnam University, Gyeongsan 38541, KoreaThe filamentous fungal pathogen <i>Fusarium</i> sp. causes several crop diseases. Some <i>Fusarium</i> sp. are endophytes that produce diverse valuable bioactive secondary metabolites. Here, extensive chemical investigation of the endophytic fungus, <i>Fusarium</i> sp. QF001, isolated from the inner rotten part of old roots of <i>Scutellariae baicalensis</i> resulted in the isolation of two new photosensitive geometrical isomers of lucilactaene (compounds <b>2</b> and <b>3</b>) along with lucilactaene (<b>6</b>) and six other known compounds (fusarubin (<b>1</b>), (+)-solaniol (<b>4</b>), javanicin (<b>5</b>), 9-desmethylherbarine (<b>7</b>), NG391 (<b>8</b>) and NG393 (<b>9</b>)). Newly isolated isomers and lucilactaene were unstable under light at room temperature and tended to be a mixture in equilibrium state when exposed to a polar protic solvent during reversed phase chromatography. Normal phase chromatography under dim light conditions with an aprotic mobile phase led to the successful isolation of the relatively unstable isomers <b>2</b> and <b>3</b>. Their structures were elucidated as 8(Z)-lucilactaene (<b>2</b>) and 4(<i>Z</i>)-lucilactaene (<b>3</b>) based on spectroscopic data. The absolute configuration of <b>4</b> was speculated to be <i>R</i> by computer-assisted specific rotation analysis. The isolated compounds could inhibit NO production and suppress pro-inflammatory cytokines expression in LPS-stimulated macrophage cells. These properties of the isolated compounds indicate their potential use as anti-inflammatory drugs.https://www.mdpi.com/1420-3049/25/4/923endophytes<i>fusarium</i><i>scutellaria baicalensis</i>anti-inflammatorylucilactaene |
| spellingShingle | Sailesh Maharjan Sang Bong Lee Geum Jin Kim Sung Jin Cho Joo-Won Nam Jungwook Chin Hyukjae Choi Isolation of Unstable Isomers of Lucilactaene and Evaluation of Anti-Inflammatory Activity of Secondary Metabolites Produced by the Endophytic Fungus <i>Fusarium</i> sp. QF001 from the Roots of <i>Scutellaria baicalensis</i> Molecules endophytes <i>fusarium</i> <i>scutellaria baicalensis</i> anti-inflammatory lucilactaene |
| title | Isolation of Unstable Isomers of Lucilactaene and Evaluation of Anti-Inflammatory Activity of Secondary Metabolites Produced by the Endophytic Fungus <i>Fusarium</i> sp. QF001 from the Roots of <i>Scutellaria baicalensis</i> |
| title_full | Isolation of Unstable Isomers of Lucilactaene and Evaluation of Anti-Inflammatory Activity of Secondary Metabolites Produced by the Endophytic Fungus <i>Fusarium</i> sp. QF001 from the Roots of <i>Scutellaria baicalensis</i> |
| title_fullStr | Isolation of Unstable Isomers of Lucilactaene and Evaluation of Anti-Inflammatory Activity of Secondary Metabolites Produced by the Endophytic Fungus <i>Fusarium</i> sp. QF001 from the Roots of <i>Scutellaria baicalensis</i> |
| title_full_unstemmed | Isolation of Unstable Isomers of Lucilactaene and Evaluation of Anti-Inflammatory Activity of Secondary Metabolites Produced by the Endophytic Fungus <i>Fusarium</i> sp. QF001 from the Roots of <i>Scutellaria baicalensis</i> |
| title_short | Isolation of Unstable Isomers of Lucilactaene and Evaluation of Anti-Inflammatory Activity of Secondary Metabolites Produced by the Endophytic Fungus <i>Fusarium</i> sp. QF001 from the Roots of <i>Scutellaria baicalensis</i> |
| title_sort | isolation of unstable isomers of lucilactaene and evaluation of anti inflammatory activity of secondary metabolites produced by the endophytic fungus i fusarium i sp qf001 from the roots of i scutellaria baicalensis i |
| topic | endophytes <i>fusarium</i> <i>scutellaria baicalensis</i> anti-inflammatory lucilactaene |
| url | https://www.mdpi.com/1420-3049/25/4/923 |
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