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Open AccessArticle

Biological Activities of Cyclic and Acyclic B-Type Laxaphycins in SH-SY5Y Human Neuroblastoma Cells

Departamento de Farmacología, Facultad de Veterinaria, Universidad de Santiago de Compostela, 27003 Lugo, Spain
Fundación Instituto de Investigación Sanitario Santiago de Compostela (FIDIS), Hospital Universitario Lucus Augusti, 27003 Lugo, Spain
PSL Research University: EPHE-UPVD-CNRS, USR 3278 CRIOBE, Université de Perpignan, 52 Avenue Paul Alduy, 66860 Perpignan, France
Laboratoire d’Excellence “CORAIL”, Université de Perpignan Via Domitia, 58 Avenue Paul Alduy, 66860 Perpignan, France
Author to whom correspondence should be addressed.
Mar. Drugs 2020, 18(7), 364;
Received: 8 June 2020 / Revised: 6 July 2020 / Accepted: 13 July 2020 / Published: 15 July 2020
Laxaphycins are a family of non-ribosomal lipopeptides that have been isolated from several cyanobacteria. Some of these compounds have presented cytotoxic activities, but their mechanism of action is poorly understood. In this work, the already described laxaphycins B and B3, and acyclolaxaphycins B and B3 were isolated from the marine cyanobacteria Anabaena torulosa. Moreover, two new acyclic compounds, [des-(Ala4-Hle5)] acyclolaxaphycins B and B3, were purified from the herviborous gastropod Stylocheilus striatus, with this being the first description of biotransformed laxaphycins. The structure of these new compounds was elucidated, together with the absolute configuration of acyclolaxaphycins B and B3. The bioactivities of the six peptides were determined in SH-SY5Y human neuroblastoma cells. Laxaphycins B and B3 were cytotoxic (IC50: 1.8 and 0.8 µM, respectively) through the induction of apoptosis. In comparison, acyclic laxaphycins did not show cytotoxicity but affected mitochondrial functioning, so their effect on autophagy-related protein expression was analyzed, finding that acyclic peptides affected this process by increasing AMPK phosphorylation and inhibiting mTOR. This work confirms the pro-apoptotic properties of cyclic laxaphycins B and is the first report indicating the effects on autophagy of their acyclic analogs. Moreover, gastropod-derived compounds presented ring opening and amino-acids deletion, a biotransformation that had not been previously described. View Full-Text
Keywords: biotransformation; laxaphycin; autophagy; apoptosis; cyanobacteria biotransformation; laxaphycin; autophagy; apoptosis; cyanobacteria
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Alvariño, R.; Alonso, E.; Bornancin, L.; Bonnard, I.; Inguimbert, N.; Banaigs, B.; Botana, L.M. Biological Activities of Cyclic and Acyclic B-Type Laxaphycins in SH-SY5Y Human Neuroblastoma Cells. Mar. Drugs 2020, 18, 364.

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