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Mar. Drugs 2019, 17(4), 229; https://doi.org/10.3390/md17040229

Chlorophyll Derivatives from Marine Cyanobacteria with Lipid-Reducing Activities

1
Interdisciplinary 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, Portugal
2
FCUP, Faculty of Science, Department of Biology, University of Porto, Rua do Campo, Alegre, 4169-007 Porto, Portugal
*
Author to whom correspondence should be addressed.
These authors contributed equally to this paper.
Received: 26 March 2019 / Revised: 11 April 2019 / Accepted: 14 April 2019 / Published: 17 April 2019
(This article belongs to the Special Issue Marine Natural Products and Obesity)
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Abstract

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 132-hydroxy-pheophytin a (1) and the new compound 132-hydroxy-pheofarnesin a (2). The structure elucidation of the new compound 2 was established based on one- and two-dimensional (1D and 2D) NMR spectroscopy and mass spectrometry. Compounds 1 and 2 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 (EC50) of 8.9 ± 0.4 µM for 1 and 15.5 ± 1.3 µM for 2. 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 1, which indicated altered peroxisome proliferator activated receptor gamma (PPARγ) mRNA expression. Lipolysis was not affected. Different food materials (Spirulina, Chlorella, spinach, and cabbage) were evaluated for the presence of 1, and the cyanobacterium Spirulina, with GRAS (generally regarded as safe) status for human consumption, contained high amounts of 1. 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. View Full-Text
Keywords: zebrafish Nile red fat metabolism assay; anti-obesity drugs; chlorophyll derivatives; murine pre-adipocytes; PPARγ zebrafish Nile red fat metabolism assay; anti-obesity drugs; chlorophyll derivatives; murine pre-adipocytes; PPARγ
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Freitas, S.; Silva, N.G.; Sousa, M.L.; Ribeiro, T.; Rosa, F.; Leão, P.N.; Vasconcelos, V.; Reis, M.A.; Urbatzka, R. Chlorophyll Derivatives from Marine Cyanobacteria with Lipid-Reducing Activities. Mar. Drugs 2019, 17, 229.

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