Cytosporin Derivatives from Arctic-Derived Fungus <i>Eutypella</i> sp. D-1 via the OSMAC Approach
A chemical investigation of the Arctic-derived fungus <i>Eutypella</i> sp. D-1 based on the OSMAC (one strain many compounds) approach resulted in the isolation of five cytosporin polyketides (compounds <b>1</b>–<b>3</b> and <b>11</b>–<b>12</b...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-06-01
|
| Series: | Marine Drugs |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1660-3397/21/7/382 |
| _version_ | 1827732564307083264 |
|---|---|
| author | Hao-Bing Yu Zhe Ning Bo Hu Yu-Ping Zhu Xiao-Ling Lu Ying He Bing-Hua Jiao Xiao-Yu Liu |
| author_facet | Hao-Bing Yu Zhe Ning Bo Hu Yu-Ping Zhu Xiao-Ling Lu Ying He Bing-Hua Jiao Xiao-Yu Liu |
| author_sort | Hao-Bing Yu |
| collection | DOAJ |
| description | A chemical investigation of the Arctic-derived fungus <i>Eutypella</i> sp. D-1 based on the OSMAC (one strain many compounds) approach resulted in the isolation of five cytosporin polyketides (compounds <b>1</b>–<b>3</b> and <b>11</b>–<b>12</b>) from rice medium and eight cytosporins (compounds <b>2</b> and <b>4</b>–<b>11</b>) from solid defined medium. The structures of the seven new compounds, eutypelleudesmane A (<b>1</b>), cytosporin Y (<b>2</b>), cytosporin Z (<b>3</b>), cytosporin Y<sub>1</sub> (<b>4</b>), cytosporin Y<sub>2</sub> (<b>5</b>), cytosporin Y<sub>3</sub> (<b>6</b>), and cytosporin E<sub>1</sub> (<b>7</b>), were elucidated by analyzing their detailed spectroscopic data. Structurally, cytosporin Y<sub>1</sub> (<b>4</b>) may be a key intermediate in the biosynthesis of the isolated cytosporins, rather than an end product. Compound <b>1</b> contained a unique skeleton formed by the ester linkage of two moieties, cytosporin F (<b>12</b>) and the eudesmane-type sesquiterpene dihydroalanto glycol. Additionally, the occurrence of cyclic carbonate moieties in compounds <b>6</b> and <b>7</b> was found to be rare in nature. The antibacterial, immunosuppressive, and cytotoxic activities of all compounds derived from <i>Eutypella</i> sp. D-1 were evaluated. Unfortunately, only compounds <b>3</b>, <b>6</b>, <b>8</b>, and <b>10</b>–<b>11</b> displayed immunosuppressive activity, with inhibitory rates of 62.9%, 59.5%, 67.8%, 55.8%, and 68.7%, respectively, at a concentration of 5 μg/mL. |
| first_indexed | 2024-03-11T00:54:01Z |
| format | Article |
| id | doaj.art-91f3884534b04a2d9e2db2df8de5d4aa |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-11T00:54:01Z |
| publishDate | 2023-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-91f3884534b04a2d9e2db2df8de5d4aa2023-11-18T20:14:00ZengMDPI AGMarine Drugs1660-33972023-06-0121738210.3390/md21070382Cytosporin Derivatives from Arctic-Derived Fungus <i>Eutypella</i> sp. D-1 via the OSMAC ApproachHao-Bing Yu0Zhe Ning1Bo Hu2Yu-Ping Zhu3Xiao-Ling Lu4Ying He5Bing-Hua Jiao6Xiao-Yu Liu7Naval Medical Center of PLA, Department of Marine Biomedicine and Polar Medicine, Naval Medical University, Shanghai 200433, ChinaNaval Medical Center of PLA, Department of Marine Biomedicine and Polar Medicine, Naval Medical University, Shanghai 200433, ChinaNaval Medical Center of PLA, Department of Marine Biomedicine and Polar Medicine, Naval Medical University, Shanghai 200433, ChinaBasic Medical Experimental Teaching Center, College of Basic Medical Sciences, Naval Medical University, Shanghai 200433, ChinaDepartment of Biochemistry and Molecular Biology, College of Basic Medical Sciences, Naval Medical University, Shanghai 200433, ChinaNaval Medical Center of PLA, Department of Marine Biomedicine and Polar Medicine, Naval Medical University, Shanghai 200433, ChinaDepartment of Biochemistry and Molecular Biology, College of Basic Medical Sciences, Naval Medical University, Shanghai 200433, ChinaNaval Medical Center of PLA, Department of Marine Biomedicine and Polar Medicine, Naval Medical University, Shanghai 200433, ChinaA chemical investigation of the Arctic-derived fungus <i>Eutypella</i> sp. D-1 based on the OSMAC (one strain many compounds) approach resulted in the isolation of five cytosporin polyketides (compounds <b>1</b>–<b>3</b> and <b>11</b>–<b>12</b>) from rice medium and eight cytosporins (compounds <b>2</b> and <b>4</b>–<b>11</b>) from solid defined medium. The structures of the seven new compounds, eutypelleudesmane A (<b>1</b>), cytosporin Y (<b>2</b>), cytosporin Z (<b>3</b>), cytosporin Y<sub>1</sub> (<b>4</b>), cytosporin Y<sub>2</sub> (<b>5</b>), cytosporin Y<sub>3</sub> (<b>6</b>), and cytosporin E<sub>1</sub> (<b>7</b>), were elucidated by analyzing their detailed spectroscopic data. Structurally, cytosporin Y<sub>1</sub> (<b>4</b>) may be a key intermediate in the biosynthesis of the isolated cytosporins, rather than an end product. Compound <b>1</b> contained a unique skeleton formed by the ester linkage of two moieties, cytosporin F (<b>12</b>) and the eudesmane-type sesquiterpene dihydroalanto glycol. Additionally, the occurrence of cyclic carbonate moieties in compounds <b>6</b> and <b>7</b> was found to be rare in nature. The antibacterial, immunosuppressive, and cytotoxic activities of all compounds derived from <i>Eutypella</i> sp. D-1 were evaluated. Unfortunately, only compounds <b>3</b>, <b>6</b>, <b>8</b>, and <b>10</b>–<b>11</b> displayed immunosuppressive activity, with inhibitory rates of 62.9%, 59.5%, 67.8%, 55.8%, and 68.7%, respectively, at a concentration of 5 μg/mL.https://www.mdpi.com/1660-3397/21/7/382cytosporinarctic fungus<i>Eutypella</i> sp.immunosuppressive activity |
| spellingShingle | Hao-Bing Yu Zhe Ning Bo Hu Yu-Ping Zhu Xiao-Ling Lu Ying He Bing-Hua Jiao Xiao-Yu Liu Cytosporin Derivatives from Arctic-Derived Fungus <i>Eutypella</i> sp. D-1 via the OSMAC Approach Marine Drugs cytosporin arctic fungus <i>Eutypella</i> sp. immunosuppressive activity |
| title | Cytosporin Derivatives from Arctic-Derived Fungus <i>Eutypella</i> sp. D-1 via the OSMAC Approach |
| title_full | Cytosporin Derivatives from Arctic-Derived Fungus <i>Eutypella</i> sp. D-1 via the OSMAC Approach |
| title_fullStr | Cytosporin Derivatives from Arctic-Derived Fungus <i>Eutypella</i> sp. D-1 via the OSMAC Approach |
| title_full_unstemmed | Cytosporin Derivatives from Arctic-Derived Fungus <i>Eutypella</i> sp. D-1 via the OSMAC Approach |
| title_short | Cytosporin Derivatives from Arctic-Derived Fungus <i>Eutypella</i> sp. D-1 via the OSMAC Approach |
| title_sort | cytosporin derivatives from arctic derived fungus i eutypella i sp d 1 via the osmac approach |
| topic | cytosporin arctic fungus <i>Eutypella</i> sp. immunosuppressive activity |
| url | https://www.mdpi.com/1660-3397/21/7/382 |
| work_keys_str_mv | AT haobingyu cytosporinderivativesfromarcticderivedfungusieutypellaispd1viatheosmacapproach AT zhening cytosporinderivativesfromarcticderivedfungusieutypellaispd1viatheosmacapproach AT bohu cytosporinderivativesfromarcticderivedfungusieutypellaispd1viatheosmacapproach AT yupingzhu cytosporinderivativesfromarcticderivedfungusieutypellaispd1viatheosmacapproach AT xiaolinglu cytosporinderivativesfromarcticderivedfungusieutypellaispd1viatheosmacapproach AT yinghe cytosporinderivativesfromarcticderivedfungusieutypellaispd1viatheosmacapproach AT binghuajiao cytosporinderivativesfromarcticderivedfungusieutypellaispd1viatheosmacapproach AT xiaoyuliu cytosporinderivativesfromarcticderivedfungusieutypellaispd1viatheosmacapproach |