Targeted Isolation of Anti-Trypanosomal Naphthofuran-Quinone Compounds from the Mangrove Plant <i>Avicennia lanata</i>
The discovery of new secondary metabolites from natural origins has become more challenging in natural products research. Different approaches have been applied to target the isolation of new bioactive metabolites from plant extracts. In this study, bioactive natural products were isolated from the...
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| Format: | Article |
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MDPI AG
2020-12-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/12/661 |
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| author | Noor Wini Mazlan Carol Clements RuAngelie Edrada-Ebel |
| author_facet | Noor Wini Mazlan Carol Clements RuAngelie Edrada-Ebel |
| author_sort | Noor Wini Mazlan |
| collection | DOAJ |
| description | The discovery of new secondary metabolites from natural origins has become more challenging in natural products research. Different approaches have been applied to target the isolation of new bioactive metabolites from plant extracts. In this study, bioactive natural products were isolated from the crude organic extract of the mangrove plant <i>Avicennia lanata</i> collected from the east coast of Peninsular Malaysia in the Setiu Wetlands, Terengganu, using HRESI-LCMS-based metabolomics-guided isolation and fractionation. Isolation work on the crude extract <i>A. lanata</i> used high-throughput chromatographic techniques to give two new naphthofuranquinone derivatives, hydroxyavicenol C (<b>1</b>) and glycosemiquinone (<b>2</b>), along with the known compounds avicenol C (<b>3</b>), avicequinone C (<b>4</b>), glycoquinone (<b>5</b>), taraxerone (<b>6</b>), taraxerol (<b>7</b>), β-sitosterol (<b>8</b>) and stigmasterol (<b>9</b>). The elucidation and identification of the targeted bioactive compounds used 1D and 2D-NMR and mass spectrometry. Except for <b>6–9</b>, all isolated naphthoquinone compounds (<b>1–5</b>) from the mangrove plant <i>A. lanata</i> showed significant anti-trypanosomal activity on <i>Trypanosoma brucei brucei</i> with MIC values of 3.12–12.5 μM. Preliminary cytotoxicity screening against normal prostate cells (PNT2A) was also performed. All compounds exhibited low cytotoxicity, with compounds <b>3</b> and <b>4</b> showing moderate cytotoxicity of 78.3% and 68.6% of the control values at 100 μg/mL, respectively. |
| first_indexed | 2024-03-10T13:53:06Z |
| format | Article |
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| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T13:53:06Z |
| publishDate | 2020-12-01 |
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| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-c058698835f34c0595d358d1d1d853562023-11-21T01:55:18ZengMDPI AGMarine Drugs1660-33972020-12-01181266110.3390/md18120661Targeted Isolation of Anti-Trypanosomal Naphthofuran-Quinone Compounds from the Mangrove Plant <i>Avicennia lanata</i>Noor Wini Mazlan0Carol Clements1RuAngelie Edrada-Ebel2Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, The John Arbuthnott Building, 161 Cathedral Street, Glasgow G4 0RE, UKStrathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, The John Arbuthnott Building, 161 Cathedral Street, Glasgow G4 0RE, UKStrathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, The John Arbuthnott Building, 161 Cathedral Street, Glasgow G4 0RE, UKThe discovery of new secondary metabolites from natural origins has become more challenging in natural products research. Different approaches have been applied to target the isolation of new bioactive metabolites from plant extracts. In this study, bioactive natural products were isolated from the crude organic extract of the mangrove plant <i>Avicennia lanata</i> collected from the east coast of Peninsular Malaysia in the Setiu Wetlands, Terengganu, using HRESI-LCMS-based metabolomics-guided isolation and fractionation. Isolation work on the crude extract <i>A. lanata</i> used high-throughput chromatographic techniques to give two new naphthofuranquinone derivatives, hydroxyavicenol C (<b>1</b>) and glycosemiquinone (<b>2</b>), along with the known compounds avicenol C (<b>3</b>), avicequinone C (<b>4</b>), glycoquinone (<b>5</b>), taraxerone (<b>6</b>), taraxerol (<b>7</b>), β-sitosterol (<b>8</b>) and stigmasterol (<b>9</b>). The elucidation and identification of the targeted bioactive compounds used 1D and 2D-NMR and mass spectrometry. Except for <b>6–9</b>, all isolated naphthoquinone compounds (<b>1–5</b>) from the mangrove plant <i>A. lanata</i> showed significant anti-trypanosomal activity on <i>Trypanosoma brucei brucei</i> with MIC values of 3.12–12.5 μM. Preliminary cytotoxicity screening against normal prostate cells (PNT2A) was also performed. All compounds exhibited low cytotoxicity, with compounds <b>3</b> and <b>4</b> showing moderate cytotoxicity of 78.3% and 68.6% of the control values at 100 μg/mL, respectively.https://www.mdpi.com/1660-3397/18/12/661mangrovemass spectrometryNMRmetabolic profilingdereplicationmultivariate analysis |
| spellingShingle | Noor Wini Mazlan Carol Clements RuAngelie Edrada-Ebel Targeted Isolation of Anti-Trypanosomal Naphthofuran-Quinone Compounds from the Mangrove Plant <i>Avicennia lanata</i> Marine Drugs mangrove mass spectrometry NMR metabolic profiling dereplication multivariate analysis |
| title | Targeted Isolation of Anti-Trypanosomal Naphthofuran-Quinone Compounds from the Mangrove Plant <i>Avicennia lanata</i> |
| title_full | Targeted Isolation of Anti-Trypanosomal Naphthofuran-Quinone Compounds from the Mangrove Plant <i>Avicennia lanata</i> |
| title_fullStr | Targeted Isolation of Anti-Trypanosomal Naphthofuran-Quinone Compounds from the Mangrove Plant <i>Avicennia lanata</i> |
| title_full_unstemmed | Targeted Isolation of Anti-Trypanosomal Naphthofuran-Quinone Compounds from the Mangrove Plant <i>Avicennia lanata</i> |
| title_short | Targeted Isolation of Anti-Trypanosomal Naphthofuran-Quinone Compounds from the Mangrove Plant <i>Avicennia lanata</i> |
| title_sort | targeted isolation of anti trypanosomal naphthofuran quinone compounds from the mangrove plant i avicennia lanata i |
| topic | mangrove mass spectrometry NMR metabolic profiling dereplication multivariate analysis |
| url | https://www.mdpi.com/1660-3397/18/12/661 |
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