Cyclodepsipeptides and Sesquiterpenes from Marine-Derived Fungus <i>Trichothecium roseum</i> and Their Biological Functions
On the basis of the ‘one strain, many compounds’ (OSMAC) strategy, chemical investigation of the marine-derived fungus <i>Trichothecium roseum</i> resulted in the isolation of trichomide cyclodepsipeptides (compounds 1⁻4) from PDB medium, and destruxin cyclo...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2018-12-01
|
| Series: | Marine Drugs |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1660-3397/16/12/519 |
| _version_ | 1811184769669529600 |
|---|---|
| author | Yuan-Ming Zhou Guang-Lin Ju Lin Xiao Xiang-Fei Zhang Feng-Yu Du |
| author_facet | Yuan-Ming Zhou Guang-Lin Ju Lin Xiao Xiang-Fei Zhang Feng-Yu Du |
| author_sort | Yuan-Ming Zhou |
| collection | DOAJ |
| description | On the basis of the ‘one strain, many compounds’ (OSMAC) strategy, chemical investigation of the marine-derived fungus <i>Trichothecium roseum</i> resulted in the isolation of trichomide cyclodepsipeptides (compounds 1⁻4) from PDB medium, and destruxin cyclodepsipeptides (compounds 5⁻7) and cyclonerodiol sesquiterpenes (compounds 8⁻10) from rice medium. The structures and absolute configurations of novel (compounds 1, 8, and 9) and known compounds were elucidated by extensive spectroscopic analyses, X-ray crystallographic analysis, and ECD calculations. All isolated compounds were evaluated for cytotoxic, nematicidal, and antifungal activities, as well as brine shrimp lethality. The novel compound 1 exhibited significant cytotoxic activities against the human cancer cell lines MCF-7, SW480, and HL-60, with IC<sub>50</sub> values of 0.079, 0.107, and 0.149 μM, respectively. In addition, it also showed significant brine shrimp lethality, with an LD<sub>50</sub> value of 0.48 μM, and moderate nematicidal activity against <i>Heterodera avenae</i>, with an LC<sub>50</sub> value of 94.9 μg/mL. This study constitutes the first report on the cytotoxic and nematicidal potential of trichomide cyclodepsipeptides. |
| first_indexed | 2024-04-11T13:19:09Z |
| format | Article |
| id | doaj.art-5b9021aa6c1f4ae8aeb860a3d671cd45 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T13:19:09Z |
| publishDate | 2018-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-5b9021aa6c1f4ae8aeb860a3d671cd452022-12-22T04:22:18ZengMDPI AGMarine Drugs1660-33972018-12-01161251910.3390/md16120519md16120519Cyclodepsipeptides and Sesquiterpenes from Marine-Derived Fungus <i>Trichothecium roseum</i> and Their Biological FunctionsYuan-Ming Zhou0Guang-Lin Ju1Lin Xiao2Xiang-Fei Zhang3Feng-Yu Du4College of Chemistry and Pharmacy, Qingdao Agricultural University, Qingdao 266109, ChinaCollege of Chemistry and Pharmacy, Qingdao Agricultural University, Qingdao 266109, ChinaCollege of Chemistry and Pharmacy, Qingdao Agricultural University, Qingdao 266109, ChinaCollege of Chemistry and Pharmacy, Qingdao Agricultural University, Qingdao 266109, ChinaCollege of Chemistry and Pharmacy, Qingdao Agricultural University, Qingdao 266109, ChinaOn the basis of the ‘one strain, many compounds’ (OSMAC) strategy, chemical investigation of the marine-derived fungus <i>Trichothecium roseum</i> resulted in the isolation of trichomide cyclodepsipeptides (compounds 1⁻4) from PDB medium, and destruxin cyclodepsipeptides (compounds 5⁻7) and cyclonerodiol sesquiterpenes (compounds 8⁻10) from rice medium. The structures and absolute configurations of novel (compounds 1, 8, and 9) and known compounds were elucidated by extensive spectroscopic analyses, X-ray crystallographic analysis, and ECD calculations. All isolated compounds were evaluated for cytotoxic, nematicidal, and antifungal activities, as well as brine shrimp lethality. The novel compound 1 exhibited significant cytotoxic activities against the human cancer cell lines MCF-7, SW480, and HL-60, with IC<sub>50</sub> values of 0.079, 0.107, and 0.149 μM, respectively. In addition, it also showed significant brine shrimp lethality, with an LD<sub>50</sub> value of 0.48 μM, and moderate nematicidal activity against <i>Heterodera avenae</i>, with an LC<sub>50</sub> value of 94.9 μg/mL. This study constitutes the first report on the cytotoxic and nematicidal potential of trichomide cyclodepsipeptides.https://www.mdpi.com/1660-3397/16/12/519marine-derived funguscyclodepsipeptidessesquiterpenescytotoxic activitynematicidal activity |
| spellingShingle | Yuan-Ming Zhou Guang-Lin Ju Lin Xiao Xiang-Fei Zhang Feng-Yu Du Cyclodepsipeptides and Sesquiterpenes from Marine-Derived Fungus <i>Trichothecium roseum</i> and Their Biological Functions Marine Drugs marine-derived fungus cyclodepsipeptides sesquiterpenes cytotoxic activity nematicidal activity |
| title | Cyclodepsipeptides and Sesquiterpenes from Marine-Derived Fungus <i>Trichothecium roseum</i> and Their Biological Functions |
| title_full | Cyclodepsipeptides and Sesquiterpenes from Marine-Derived Fungus <i>Trichothecium roseum</i> and Their Biological Functions |
| title_fullStr | Cyclodepsipeptides and Sesquiterpenes from Marine-Derived Fungus <i>Trichothecium roseum</i> and Their Biological Functions |
| title_full_unstemmed | Cyclodepsipeptides and Sesquiterpenes from Marine-Derived Fungus <i>Trichothecium roseum</i> and Their Biological Functions |
| title_short | Cyclodepsipeptides and Sesquiterpenes from Marine-Derived Fungus <i>Trichothecium roseum</i> and Their Biological Functions |
| title_sort | cyclodepsipeptides and sesquiterpenes from marine derived fungus i trichothecium roseum i and their biological functions |
| topic | marine-derived fungus cyclodepsipeptides sesquiterpenes cytotoxic activity nematicidal activity |
| url | https://www.mdpi.com/1660-3397/16/12/519 |
| work_keys_str_mv | AT yuanmingzhou cyclodepsipeptidesandsesquiterpenesfrommarinederivedfungusitrichotheciumroseumiandtheirbiologicalfunctions AT guanglinju cyclodepsipeptidesandsesquiterpenesfrommarinederivedfungusitrichotheciumroseumiandtheirbiologicalfunctions AT linxiao cyclodepsipeptidesandsesquiterpenesfrommarinederivedfungusitrichotheciumroseumiandtheirbiologicalfunctions AT xiangfeizhang cyclodepsipeptidesandsesquiterpenesfrommarinederivedfungusitrichotheciumroseumiandtheirbiologicalfunctions AT fengyudu cyclodepsipeptidesandsesquiterpenesfrommarinederivedfungusitrichotheciumroseumiandtheirbiologicalfunctions |