Chlorophyll Derivatives from Marine Cyanobacteria with Lipid-Reducing Activities
Marine organisms, particularly cyanobacteria, are important resources for the production of bioactive secondary metabolites for the treatment of human diseases. In this study, a bioassay-guided approach was used to discover metabolites with lipid-reducing activity. Two chlorophyll derivatives were s...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-04-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/17/4/229 |
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| author | Sara Freitas Natália Gonçalves Silva Maria Lígia Sousa Tiago Ribeiro Filipa Rosa Pedro N. Leão Vitor Vasconcelos Mariana Alves Reis Ralph Urbatzka |
| author_facet | Sara Freitas Natália Gonçalves Silva Maria Lígia Sousa Tiago Ribeiro Filipa Rosa Pedro N. Leão Vitor Vasconcelos Mariana Alves Reis Ralph Urbatzka |
| author_sort | Sara Freitas |
| collection | DOAJ |
| description | Marine organisms, particularly cyanobacteria, are important resources for the production of bioactive secondary metabolites for the treatment of human diseases. In this study, a bioassay-guided approach was used to discover metabolites with lipid-reducing activity. Two chlorophyll derivatives were successfully isolated, the previously described 13<sup>2</sup>-hydroxy-pheophytin a (<b>1</b>) and the new compound 13<sup>2</sup>-hydroxy-pheofarnesin a (<b>2</b>). The structure elucidation of the new compound <b>2</b> was established based on one- and two-dimensional (1D and 2D) NMR spectroscopy and mass spectrometry. Compounds <b>1</b> and <b>2</b> showed significant neutral lipid-reducing activity in the zebrafish Nile red fat metabolism assay after 48 h of exposure with a half maximal effective concentration (EC<sub>50</sub>) of 8.9 ± 0.4 µM for <b>1</b> and 15.5 ± 1.3 µM for <b>2</b>. Both compounds additionally reduced neutral lipid accumulation in 3T3-L1 multicellular spheroids of murine preadipocytes. Molecular profiling of mRNA expression of some target genes was evaluated for the higher potent compound <b>1,</b> which indicated altered peroxisome proliferator activated receptor gamma (PPARγ) mRNA expression. Lipolysis was not affected. Different food materials (<i>Spirulina</i>, <i>Chlorella</i>, spinach, and cabbage) were evaluated for the presence of <b>1,</b> and the cyanobacterium <i>Spirulina</i>, with GRAS (generally regarded as safe) status for human consumption, contained high amounts of <b>1</b>. In summary, known and novel chlorophyll derivatives were discovered from marine cyanobacteria with relevant lipid-reducing activities, which in the future may be developed into nutraceuticals. |
| first_indexed | 2024-04-11T12:40:55Z |
| format | Article |
| id | doaj.art-6ea23d4e20284c12b00a6a5cea84efc4 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T12:40:55Z |
| publishDate | 2019-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-6ea23d4e20284c12b00a6a5cea84efc42022-12-22T04:23:29ZengMDPI AGMarine Drugs1660-33972019-04-0117422910.3390/md17040229md17040229Chlorophyll Derivatives from Marine Cyanobacteria with Lipid-Reducing ActivitiesSara Freitas0Natália Gonçalves Silva1Maria Lígia Sousa2Tiago Ribeiro3Filipa Rosa4Pedro N. Leão5Vitor Vasconcelos6Mariana Alves Reis7Ralph Urbatzka8Interdisciplinary Center of Marine and Environmental Research (CIIMAR/CIMAR), University of Porto, Terminal de Cruzeiros de Leixões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalInterdisciplinary Center of Marine and Environmental Research (CIIMAR/CIMAR), University of Porto, Terminal de Cruzeiros de Leixões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalInterdisciplinary Center of Marine and Environmental Research (CIIMAR/CIMAR), University of Porto, Terminal de Cruzeiros de Leixões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalInterdisciplinary Center of Marine and Environmental Research (CIIMAR/CIMAR), University of Porto, Terminal de Cruzeiros de Leixões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalInterdisciplinary Center of Marine and Environmental Research (CIIMAR/CIMAR), University of Porto, Terminal de Cruzeiros de Leixões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalInterdisciplinary Center of Marine and Environmental Research (CIIMAR/CIMAR), University of Porto, Terminal de Cruzeiros de Leixões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalInterdisciplinary Center of Marine and Environmental Research (CIIMAR/CIMAR), University of Porto, Terminal de Cruzeiros de Leixões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalInterdisciplinary Center of Marine and Environmental Research (CIIMAR/CIMAR), University of Porto, Terminal de Cruzeiros de Leixões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalInterdisciplinary Center of Marine and Environmental Research (CIIMAR/CIMAR), University of Porto, Terminal de Cruzeiros de Leixões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalMarine organisms, particularly cyanobacteria, are important resources for the production of bioactive secondary metabolites for the treatment of human diseases. In this study, a bioassay-guided approach was used to discover metabolites with lipid-reducing activity. Two chlorophyll derivatives were successfully isolated, the previously described 13<sup>2</sup>-hydroxy-pheophytin a (<b>1</b>) and the new compound 13<sup>2</sup>-hydroxy-pheofarnesin a (<b>2</b>). The structure elucidation of the new compound <b>2</b> was established based on one- and two-dimensional (1D and 2D) NMR spectroscopy and mass spectrometry. Compounds <b>1</b> and <b>2</b> showed significant neutral lipid-reducing activity in the zebrafish Nile red fat metabolism assay after 48 h of exposure with a half maximal effective concentration (EC<sub>50</sub>) of 8.9 ± 0.4 µM for <b>1</b> and 15.5 ± 1.3 µM for <b>2</b>. Both compounds additionally reduced neutral lipid accumulation in 3T3-L1 multicellular spheroids of murine preadipocytes. Molecular profiling of mRNA expression of some target genes was evaluated for the higher potent compound <b>1,</b> which indicated altered peroxisome proliferator activated receptor gamma (PPARγ) mRNA expression. Lipolysis was not affected. Different food materials (<i>Spirulina</i>, <i>Chlorella</i>, spinach, and cabbage) were evaluated for the presence of <b>1,</b> and the cyanobacterium <i>Spirulina</i>, with GRAS (generally regarded as safe) status for human consumption, contained high amounts of <b>1</b>. In summary, known and novel chlorophyll derivatives were discovered from marine cyanobacteria with relevant lipid-reducing activities, which in the future may be developed into nutraceuticals.https://www.mdpi.com/1660-3397/17/4/229zebrafish Nile red fat metabolism assayanti-obesity drugschlorophyll derivativesmurine pre-adipocytesPPARγ |
| spellingShingle | Sara Freitas Natália Gonçalves Silva Maria Lígia Sousa Tiago Ribeiro Filipa Rosa Pedro N. Leão Vitor Vasconcelos Mariana Alves Reis Ralph Urbatzka Chlorophyll Derivatives from Marine Cyanobacteria with Lipid-Reducing Activities Marine Drugs zebrafish Nile red fat metabolism assay anti-obesity drugs chlorophyll derivatives murine pre-adipocytes PPARγ |
| title | Chlorophyll Derivatives from Marine Cyanobacteria with Lipid-Reducing Activities |
| title_full | Chlorophyll Derivatives from Marine Cyanobacteria with Lipid-Reducing Activities |
| title_fullStr | Chlorophyll Derivatives from Marine Cyanobacteria with Lipid-Reducing Activities |
| title_full_unstemmed | Chlorophyll Derivatives from Marine Cyanobacteria with Lipid-Reducing Activities |
| title_short | Chlorophyll Derivatives from Marine Cyanobacteria with Lipid-Reducing Activities |
| title_sort | chlorophyll derivatives from marine cyanobacteria with lipid reducing activities |
| topic | zebrafish Nile red fat metabolism assay anti-obesity drugs chlorophyll derivatives murine pre-adipocytes PPARγ |
| url | https://www.mdpi.com/1660-3397/17/4/229 |
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