Integrating Molecular Networking and <sup>1</sup>H NMR Spectroscopy for Isolation of Bioactive Metabolites from the Persian Gulf Sponge <i>Axinella sinoxea</i>
The geographic position, highly fluctuating sea temperatures and hypersalinity make Persian Gulf an extreme environment. Although this unique environment has high biodiversity dominated by invertebrates, its potential in marine biodiscovery has largely remained untapped. Herein, we aimed at a detail...
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| Format: | Article |
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MDPI AG
2020-07-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/7/366 |
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| author | Reza Mohsenian Kouchaksaraee Mahdi Moridi Farimani Fengjie Li Melika Nazemi Deniz Tasdemir |
| author_facet | Reza Mohsenian Kouchaksaraee Mahdi Moridi Farimani Fengjie Li Melika Nazemi Deniz Tasdemir |
| author_sort | Reza Mohsenian Kouchaksaraee |
| collection | DOAJ |
| description | The geographic position, highly fluctuating sea temperatures and hypersalinity make Persian Gulf an extreme environment. Although this unique environment has high biodiversity dominated by invertebrates, its potential in marine biodiscovery has largely remained untapped. Herein, we aimed at a detailed analysis of the metabolome and bioactivity profiles of the marine sponge <i>Axinella sinoxea</i> collected from the northeast coast of the Persian Gulf in Iran. The crude extract and its Kupchan subextracts were tested in multiple in-house bioassays, and the crude extract and its CHCl<sub>3</sub>-soluble portion showed in vitro antibacterial activity against Methicillin-resistant <i>Staphylococcus aureus</i> (MRSA) and <i>Enterococcus faecium</i> (Efm). A molecular networking (MN)-based dereplication strategy by UPLC-MS/MS revealed the presence of phospholipids and steroids, while <sup>1</sup>H NMR spectroscopy indicated the presence of additional metabolites, such as diketopiperazines (DKPs). Integrated MN and <sup>1</sup>H NMR analyses on both the crude and CHCl<sub>3</sub> extracts combined with an antibacterial activity-guided isolation approach afforded eight metabolites: a new diketopiperazine, (-)-cyclo(<i>L</i>-<i>trans</i>-Hyp-<i>L</i>-Ile) (<b>8</b>); a known diketopiperazine, cyclo(<i>L</i>-<i>trans</i>-Hyp-<i>L</i>-Phe) (<b>7</b>); two known phospholipids, 1-<i>O</i>-hexadecyl-<i>sn</i>-glycero-3-phosphocholine (<b>1</b>) and 1-<i>O</i>-octadecanoyl-<i>sn</i>-glycero-3-phosphocholine (<b>2</b>); two known steroids, 3β-hydroxycholest-5-ene-7,24-dione (<b>3</b>) and (22<i>E</i>)-3β-hydroxycholesta-5,22-diene-7,24-dione (<b>4</b>); two known monoterpenes, loliolide (<b>5</b>) and 5-<i>epi</i>-loliolide (<b>6</b>). The chemical structures of the isolates were elucidated by a combination of NMR spectroscopy, HRMS and [α]<sub>D</sub> analyses. All compounds were tested against MRSA and Efm, and compound <b>3</b> showed moderate antibacterial activity against MRSA (IC<sub>50</sub> value 70 μg/mL). This is the first study that has dealt with chemical and bioactivity profiling of <i>A.</i> <i>sinoxea</i> leading to isolation and characterization of pure sponge metabolites. |
| first_indexed | 2024-03-10T18:26:49Z |
| format | Article |
| id | doaj.art-88da563133084f0b829321b69eaa9a8b |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T18:26:49Z |
| publishDate | 2020-07-01 |
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| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-88da563133084f0b829321b69eaa9a8b2023-11-20T06:56:44ZengMDPI AGMarine Drugs1660-33972020-07-0118736610.3390/md18070366Integrating Molecular Networking and <sup>1</sup>H NMR Spectroscopy for Isolation of Bioactive Metabolites from the Persian Gulf Sponge <i>Axinella sinoxea</i>Reza Mohsenian Kouchaksaraee0Mahdi Moridi Farimani1Fengjie Li2Melika Nazemi3Deniz Tasdemir4Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran 1983969411, IranDepartment of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran 1983969411, IranGEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products Chemistry, GEOMAR Helmholtz Centre for Ocean Research Kiel, Am Kiel-Kanal 44, 24106 Kiel, GermanyPersian Gulf and Oman Sea Ecological Center, Iranian Fisheries Science Research Institute, Agricultural Research, Education and Extension Organization (AREEO), Bandar Abbas 7916793165, IranGEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products Chemistry, GEOMAR Helmholtz Centre for Ocean Research Kiel, Am Kiel-Kanal 44, 24106 Kiel, GermanyThe geographic position, highly fluctuating sea temperatures and hypersalinity make Persian Gulf an extreme environment. Although this unique environment has high biodiversity dominated by invertebrates, its potential in marine biodiscovery has largely remained untapped. Herein, we aimed at a detailed analysis of the metabolome and bioactivity profiles of the marine sponge <i>Axinella sinoxea</i> collected from the northeast coast of the Persian Gulf in Iran. The crude extract and its Kupchan subextracts were tested in multiple in-house bioassays, and the crude extract and its CHCl<sub>3</sub>-soluble portion showed in vitro antibacterial activity against Methicillin-resistant <i>Staphylococcus aureus</i> (MRSA) and <i>Enterococcus faecium</i> (Efm). A molecular networking (MN)-based dereplication strategy by UPLC-MS/MS revealed the presence of phospholipids and steroids, while <sup>1</sup>H NMR spectroscopy indicated the presence of additional metabolites, such as diketopiperazines (DKPs). Integrated MN and <sup>1</sup>H NMR analyses on both the crude and CHCl<sub>3</sub> extracts combined with an antibacterial activity-guided isolation approach afforded eight metabolites: a new diketopiperazine, (-)-cyclo(<i>L</i>-<i>trans</i>-Hyp-<i>L</i>-Ile) (<b>8</b>); a known diketopiperazine, cyclo(<i>L</i>-<i>trans</i>-Hyp-<i>L</i>-Phe) (<b>7</b>); two known phospholipids, 1-<i>O</i>-hexadecyl-<i>sn</i>-glycero-3-phosphocholine (<b>1</b>) and 1-<i>O</i>-octadecanoyl-<i>sn</i>-glycero-3-phosphocholine (<b>2</b>); two known steroids, 3β-hydroxycholest-5-ene-7,24-dione (<b>3</b>) and (22<i>E</i>)-3β-hydroxycholesta-5,22-diene-7,24-dione (<b>4</b>); two known monoterpenes, loliolide (<b>5</b>) and 5-<i>epi</i>-loliolide (<b>6</b>). The chemical structures of the isolates were elucidated by a combination of NMR spectroscopy, HRMS and [α]<sub>D</sub> analyses. All compounds were tested against MRSA and Efm, and compound <b>3</b> showed moderate antibacterial activity against MRSA (IC<sub>50</sub> value 70 μg/mL). This is the first study that has dealt with chemical and bioactivity profiling of <i>A.</i> <i>sinoxea</i> leading to isolation and characterization of pure sponge metabolites.https://www.mdpi.com/1660-3397/18/7/366marine sponge<i>Axinella sinoxea</i>Persian Gulfmolecular networking<sup>1</sup>H NMR spectroscopydiketopiperazine |
| spellingShingle | Reza Mohsenian Kouchaksaraee Mahdi Moridi Farimani Fengjie Li Melika Nazemi Deniz Tasdemir Integrating Molecular Networking and <sup>1</sup>H NMR Spectroscopy for Isolation of Bioactive Metabolites from the Persian Gulf Sponge <i>Axinella sinoxea</i> Marine Drugs marine sponge <i>Axinella sinoxea</i> Persian Gulf molecular networking <sup>1</sup>H NMR spectroscopy diketopiperazine |
| title | Integrating Molecular Networking and <sup>1</sup>H NMR Spectroscopy for Isolation of Bioactive Metabolites from the Persian Gulf Sponge <i>Axinella sinoxea</i> |
| title_full | Integrating Molecular Networking and <sup>1</sup>H NMR Spectroscopy for Isolation of Bioactive Metabolites from the Persian Gulf Sponge <i>Axinella sinoxea</i> |
| title_fullStr | Integrating Molecular Networking and <sup>1</sup>H NMR Spectroscopy for Isolation of Bioactive Metabolites from the Persian Gulf Sponge <i>Axinella sinoxea</i> |
| title_full_unstemmed | Integrating Molecular Networking and <sup>1</sup>H NMR Spectroscopy for Isolation of Bioactive Metabolites from the Persian Gulf Sponge <i>Axinella sinoxea</i> |
| title_short | Integrating Molecular Networking and <sup>1</sup>H NMR Spectroscopy for Isolation of Bioactive Metabolites from the Persian Gulf Sponge <i>Axinella sinoxea</i> |
| title_sort | integrating molecular networking and sup 1 sup h nmr spectroscopy for isolation of bioactive metabolites from the persian gulf sponge i axinella sinoxea i |
| topic | marine sponge <i>Axinella sinoxea</i> Persian Gulf molecular networking <sup>1</sup>H NMR spectroscopy diketopiperazine |
| url | https://www.mdpi.com/1660-3397/18/7/366 |
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