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Luis M. Botana
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Original research article
Published: 07 July 2021 in Frontiers in Pharmacology
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Crambescins are guanidine alkaloids from the sponge Crambe crambe. Crambescin C1 (CC) induces metallothionein genes and nitric oxide (NO) is one of the triggers. We studied and compared the in vitro, in vivo, and in silico effects of some crambescine A and C analogs. HepG2 gene expression was analyzed using microarrays. Vasodilation was studied in rat aortic rings. In vivo hypotensive effect was directly measured in anesthetized rats. The targets of crambescines were studied in silico. CC and homo-crambescine C1 (HCC), but not crambescine A1 (CA), induced metallothioneins transcripts. CC increased NO production in HepG2 cells. In isolated rat aortic rings, CC and HCC induced an endothelium-dependent relaxation related to eNOS activation and an endothelium-independent relaxation related to iNOS activation, hence both compounds increase NO and reduce vascular tone. In silico analysis also points to eNOS and iNOS as targets of Crambescin C1 and source of NO increment. CC effect is mediated through crambescin binding to the active site of eNOS and iNOS. CC docking studies in iNOS and eNOS active site revealed hydrogen bonding of the hydroxylated chain with residues Glu377 and Glu361, involved in the substrate recognition, and explains its higher binding affinity than CA. The later interaction and the extra polar contacts with its pyrimidine moiety, absent in the endogenous substrate, explain its role as exogenous substrate of NOSs and NO production. Our results suggest that CC serve as a basis to develop new useful drugs when bioavailability of NO is perturbed.

ACS Style

Juan A. Rubiolo; Emilio Lence; Concepción González-Bello; María Roel; José Gil-Longo; Manuel Campos-Toimil; Eva Ternon; Olivier P. Thomas; Antonio González-Cantalapiedra; Henar López-Alonso; Mercedes R. Vieytes; Luis M. Botana. Crambescin C1 Acts as A Possible Substrate of iNOS and eNOS Increasing Nitric Oxide Production and Inducing In Vivo Hypotensive Effect. Frontiers in Pharmacology 2021, 12, 694639 .

AMA Style

Juan A. Rubiolo, Emilio Lence, Concepción González-Bello, María Roel, José Gil-Longo, Manuel Campos-Toimil, Eva Ternon, Olivier P. Thomas, Antonio González-Cantalapiedra, Henar López-Alonso, Mercedes R. Vieytes, Luis M. Botana. Crambescin C1 Acts as A Possible Substrate of iNOS and eNOS Increasing Nitric Oxide Production and Inducing In Vivo Hypotensive Effect. Frontiers in Pharmacology. 2021; 12 ():694639.

Chicago/Turabian Style

Juan A. Rubiolo; Emilio Lence; Concepción González-Bello; María Roel; José Gil-Longo; Manuel Campos-Toimil; Eva Ternon; Olivier P. Thomas; Antonio González-Cantalapiedra; Henar López-Alonso; Mercedes R. Vieytes; Luis M. Botana. 2021. "Crambescin C1 Acts as A Possible Substrate of iNOS and eNOS Increasing Nitric Oxide Production and Inducing In Vivo Hypotensive Effect." Frontiers in Pharmacology 12, no. : 694639.

Organ toxicity and mechanisms
Published: 20 June 2021 in Archives of Toxicology
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The consumption of contaminated shellfish with okadaic acid (OA) group of toxins leads to diarrhoeic shellfish poisoning (DSP) characterized by a set of symptoms including nausea, vomiting and diarrhoea. These phycotoxins are Ser/Thr phosphatase inhibitors, which produce hyperphosphorylation in cellular proteins. However, this inhibition does not fully explain the symptomatology reported and other targets could be relevant to the toxicity. Previous studies have indicated a feasible involvement of the nervous system. We performed a set of in vivo approaches to elucidate whether neuropeptide Y (NPY), Peptide YY (PYY) or serotonin (5-HT) was implicated in the early OA-induced diarrhoea. Fasted Swiss female mice were administered NPY, PYY(3–36) or cyproheptadine intraperitoneal prior to oral OA treatment (250 µg/kg). A non-significant delay in diarrhoea onset was observed for NPY (107 µg/kg) and PYY(3–36) (1 mg/kg) pre-treatment. On the contrary, the serotonin antagonist cyproheptadine was able to block (10 mg/kg) or delay (0.1 and 1 mg/kg) diarrhoea onset suggesting a role of 5-HT. This is the first report of the possible involvement of serotonin in OA-induced poisoning.

ACS Style

M. Carmen Louzao; Celia Costas; Paula Abal; Toshiyuki Suzuki; Ryuichi Watanabe; Natalia Vilariño; Cristina Carrera; Andrea Boente-Juncal; Carmen Vale; Mercedes R. Vieytes; Luis M. Botana. Serotonin involvement in okadaic acid-induced diarrhoea in vivo. Archives of Toxicology 2021, 95, 1 -17.

AMA Style

M. Carmen Louzao, Celia Costas, Paula Abal, Toshiyuki Suzuki, Ryuichi Watanabe, Natalia Vilariño, Cristina Carrera, Andrea Boente-Juncal, Carmen Vale, Mercedes R. Vieytes, Luis M. Botana. Serotonin involvement in okadaic acid-induced diarrhoea in vivo. Archives of Toxicology. 2021; 95 (8):1-17.

Chicago/Turabian Style

M. Carmen Louzao; Celia Costas; Paula Abal; Toshiyuki Suzuki; Ryuichi Watanabe; Natalia Vilariño; Cristina Carrera; Andrea Boente-Juncal; Carmen Vale; Mercedes R. Vieytes; Luis M. Botana. 2021. "Serotonin involvement in okadaic acid-induced diarrhoea in vivo." Archives of Toxicology 95, no. 8: 1-17.

Journal article
Published: 23 March 2021 in Food Chemistry
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A simple method for the quantification of 40 mycotoxins in milk was developed. This method is based on a QuEChERS extraction followed by the ultra-high liquid chromatography tandem mass spectrometry (UHPLC-MS/MS) detection, and allows the simultaneous analysis of regulated, emerging, and modified compounds. A sample treatment procedure was optimized to include a concentration step for the analysis of some compounds such as aflatoxin M1. The method was in-house validated in terms of limits of detection (LODs), limits of quantification (LOQs), linearity, recoveries, and precision. LOQs lower than 10 ng/mL were obtained, and recoveries ranged from 61% to 120% with a precision, expressed as the relative standard deviation, lower than 15%. Therefore, acceptable performance characteristics were obtained fulfilling European regulations. The method was successfully applied for the quantification of mycotoxins in raw milk. It can be highlighted high occurrence of beauvericin and enniatins were found in low amounts.

ACS Style

Jesús M. González-Jartín; Inés Rodríguez-Cañás; Amparo Alfonso; María J. Sainz; Mercedes R. Vieytes; Ana Gomes; Isabel Ramos; Luis M. Botana. Multianalyte method for the determination of regulated, emerging and modified mycotoxins in milk: QuEChERS extraction followed by UHPLC–MS/MS analysis. Food Chemistry 2021, 356, 129647 .

AMA Style

Jesús M. González-Jartín, Inés Rodríguez-Cañás, Amparo Alfonso, María J. Sainz, Mercedes R. Vieytes, Ana Gomes, Isabel Ramos, Luis M. Botana. Multianalyte method for the determination of regulated, emerging and modified mycotoxins in milk: QuEChERS extraction followed by UHPLC–MS/MS analysis. Food Chemistry. 2021; 356 ():129647.

Chicago/Turabian Style

Jesús M. González-Jartín; Inés Rodríguez-Cañás; Amparo Alfonso; María J. Sainz; Mercedes R. Vieytes; Ana Gomes; Isabel Ramos; Luis M. Botana. 2021. "Multianalyte method for the determination of regulated, emerging and modified mycotoxins in milk: QuEChERS extraction followed by UHPLC–MS/MS analysis." Food Chemistry 356, no. : 129647.

Journal article
Published: 04 March 2021 in Molecules
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Marine natural products have exhibited uncommon chemical structures with relevant antitumor properties highlighting their potential to inspire the development of new anticancer agents. The goal of this work was to study the antitumor activities of the brominated diterpene sphaerodactylomelol, a rare example of the dactylomelane family. Cytotoxicity (10–100 µM; 24 h) was evaluated on tumor cells (A549, CACO-2, HCT-15, MCF-7, NCI-H226, PC-3, SH-SY5Y, SK-ML-28) and the effects estimated by MTT assay. Hydrogen peroxide (H2O2) levels and apoptosis biomarkers (membrane translocation of phosphatidylserine, depolarization of mitochondrial membrane potential, Caspase-9 activity, and DNA condensation and/or fragmentation) were studied in the breast adenocarcinoma cellular model (MCF-7) and its genotoxicity on mouse fibroblasts (L929). Sphaerodactylomelol displayed an IC50 range between 33.04 and 89.41 µM without selective activity for a specific tumor tissue. The cells’ viability decrease was accompanied by an increase on H2O2 production, a depolarization of mitochondrial membrane potential and an increase of Caspase-9 activity and DNA fragmentation. However, the DNA damage studies in L929 non-malignant cell line suggested that this compound is not genotoxic for normal fibroblasts. Overall, the results suggest that the cytotoxicity of sphaerodactylomelol seems to be mediated by an increase of H2O2 levels and downstream apoptosis.

ACS Style

Celso Alves; Joana Silva; Susete Pinteus; Eva Alonso; Rebeca Alvariño; Adriana Duarte; Diorge Marmitt; Márcia Goettert; Helena Gaspar; Amparo Alfonso; Maria Alpoim; Luis M. Botana; Rui Pedrosa. Cytotoxic Mechanism of Sphaerodactylomelol, an Uncommon Bromoditerpene Isolated from Sphaerococcus coronopifolius. Molecules 2021, 26, 1374 .

AMA Style

Celso Alves, Joana Silva, Susete Pinteus, Eva Alonso, Rebeca Alvariño, Adriana Duarte, Diorge Marmitt, Márcia Goettert, Helena Gaspar, Amparo Alfonso, Maria Alpoim, Luis M. Botana, Rui Pedrosa. Cytotoxic Mechanism of Sphaerodactylomelol, an Uncommon Bromoditerpene Isolated from Sphaerococcus coronopifolius. Molecules. 2021; 26 (5):1374.

Chicago/Turabian Style

Celso Alves; Joana Silva; Susete Pinteus; Eva Alonso; Rebeca Alvariño; Adriana Duarte; Diorge Marmitt; Márcia Goettert; Helena Gaspar; Amparo Alfonso; Maria Alpoim; Luis M. Botana; Rui Pedrosa. 2021. "Cytotoxic Mechanism of Sphaerodactylomelol, an Uncommon Bromoditerpene Isolated from Sphaerococcus coronopifolius." Molecules 26, no. 5: 1374.

Journal article
Published: 08 January 2021 in Marine Drugs
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Okadaic acid (OA) and its main structural analogs dinophysistoxin-1 (DTX1) and dinophysistoxin-2 (DTX2) are marine lipophilic phycotoxins distributed worldwide that can be accumulated by edible shellfish and can cause diarrheic shellfish poisoning (DSP). In order to study their toxicokinetics, mice were treated with different doses of OA, DTX1, or DTX2 and signs of toxicity were recorded up to 24 h. Toxin distribution in the main organs from the gastrointestinal tract was assessed by liquid chromatography-mass spectrometry (LC/MS/MS) analysis. Our results indicate a dose-dependency in gastrointestinal absorption of these toxins. Twenty-four hours post-administration, the highest concentration of toxin was detected in the stomach and, in descending order, in the large intestine, small intestine, and liver. There was also a different toxicokinetic pathway between OA, DTX1, and DTX2. When the same toxin doses are compared, more OA than DTX1 is detected in the small intestine. OA and DTX1 showed similar concentrations in the stomach, liver, and large intestine tissues, but the amount of DTX2 is much lower in all these organs, providing information on DSP toxicokinetics for human safety assessment.

ACS Style

M. Carmen Louzao; Paula Abal; Celia Costas; Toshiyuki Suzuki; Ryuichi Watanabe; Natalia Vilariño; Ana M. Botana; Mercedes R. Vieytes; Luis M. Botana. DSP Toxin Distribution across Organs in Mice after Acute Oral Administration. Marine Drugs 2021, 19, 23 .

AMA Style

M. Carmen Louzao, Paula Abal, Celia Costas, Toshiyuki Suzuki, Ryuichi Watanabe, Natalia Vilariño, Ana M. Botana, Mercedes R. Vieytes, Luis M. Botana. DSP Toxin Distribution across Organs in Mice after Acute Oral Administration. Marine Drugs. 2021; 19 (1):23.

Chicago/Turabian Style

M. Carmen Louzao; Paula Abal; Celia Costas; Toshiyuki Suzuki; Ryuichi Watanabe; Natalia Vilariño; Ana M. Botana; Mercedes R. Vieytes; Luis M. Botana. 2021. "DSP Toxin Distribution across Organs in Mice after Acute Oral Administration." Marine Drugs 19, no. 1: 23.

Journal article
Published: 17 October 2020 in Marine Pollution Bulletin
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In the last decades, due to monitoring programs and strict legislation poisoning incidents occurrence provoked by ingestion of naturally contaminated marine organisms has decreased. However, climate change and anthropogenic interference contributed to the expansion and establishment of toxic alien species to more temperate ecosystems. In this work, the coasts of Madeira, São Miguel islands and the northwestern Moroccan coast were surveyed for four groups of lipophilic toxins (yessotoxins, azaspiracids, pectenotoxins, and spirolides), searching for new vectors and geographical tendencies. Twenty-four species benthic organisms were screened using UHPLC-MS/MS technique. We report 19 new vectors for these toxins, six of them with commercial interest (P. aspera, P. ordinaria, C. lampas, P. pollicipes, H. tuberculata and P. lividus). Regarding toxin uptake a south-north gradient was detected. This study contributes to the update of monitoring routines and legislation policies, comprising a wider range of vectors, to better serve consumers and ecosystems preservation.

ACS Style

Marisa Silva; Inés Rodríguez; Aldo Barreiro; Manfred Kaufmann; Ana Isabel Neto; Meryem Hassouani; Brahim Sabour; Amparo Alfonso; Luis M. Botana; Vitor Vasconcelos. Lipophilic toxins occurrence in non-traditional invertebrate vectors from North Atlantic Waters (Azores, Madeira, and Morocco): Update on geographical tendencies and new challenges for monitoring routines. Marine Pollution Bulletin 2020, 161, 111725 .

AMA Style

Marisa Silva, Inés Rodríguez, Aldo Barreiro, Manfred Kaufmann, Ana Isabel Neto, Meryem Hassouani, Brahim Sabour, Amparo Alfonso, Luis M. Botana, Vitor Vasconcelos. Lipophilic toxins occurrence in non-traditional invertebrate vectors from North Atlantic Waters (Azores, Madeira, and Morocco): Update on geographical tendencies and new challenges for monitoring routines. Marine Pollution Bulletin. 2020; 161 ():111725.

Chicago/Turabian Style

Marisa Silva; Inés Rodríguez; Aldo Barreiro; Manfred Kaufmann; Ana Isabel Neto; Meryem Hassouani; Brahim Sabour; Amparo Alfonso; Luis M. Botana; Vitor Vasconcelos. 2020. "Lipophilic toxins occurrence in non-traditional invertebrate vectors from North Atlantic Waters (Azores, Madeira, and Morocco): Update on geographical tendencies and new challenges for monitoring routines." Marine Pollution Bulletin 161, no. : 111725.

Journal article
Published: 24 September 2020 in Toxins
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Seafood represents a significant part of the human staple diet. In the recent years, the identification of emerging lipophilic marine toxins has increased, leading to the potential for consumers to be intoxicated by these toxins. In the present work, we investigate the presence of lipophilic marine toxins (both regulated and emerging) in commercial seafood products from non-European locations, including mussels Mytilus chilensis from Chile, clams Tawerea gayi and Metetrix lyrate from the Southeast Pacific and Vietnam, and food supplements based on mussels formulations of Perna canaliculus from New Zealand. All these products were purchased from European Union markets and they were analyzed by UPLC-MS/MS. Results showed the presence of the emerging pinnatoxin-G in mussels Mytilus chilensis at levels up to 5.2 µg/kg and azaspiracid-2 and pectenotoxin-2 in clams Tawera gayi up to 4.33 µg/kg and 10.88 µg/kg, respectively. This study confirms the presence of pinnatoxins in Chile, one of the major mussel producers worldwide. Chromatograms showed the presence of 13-desmethyl spirolide C in dietary supplements in the range of 33.2–97.9 µg/kg after an extraction with water and methanol from 0.39 g of the green lipped mussels powder. As far as we know, this constitutes the first time that an emerging cyclic imine toxin in dietary supplements is reported. Identifying new matrix, locations, and understanding emerging toxin distribution area are important for preventing the risks of spreading and contamination linked to these compounds.

ACS Style

Paz Otero; Carmen Vale; Andrea Boente-Juncal; Celia Costas; M. Louzao; Luis Botana. Detection of Cyclic Imine Toxins in Dietary Supplements of Green Lipped Mussels (Perna canaliculus) and in Shellfish Mytilus chilensis. Toxins 2020, 12, 613 .

AMA Style

Paz Otero, Carmen Vale, Andrea Boente-Juncal, Celia Costas, M. Louzao, Luis Botana. Detection of Cyclic Imine Toxins in Dietary Supplements of Green Lipped Mussels (Perna canaliculus) and in Shellfish Mytilus chilensis. Toxins. 2020; 12 (10):613.

Chicago/Turabian Style

Paz Otero; Carmen Vale; Andrea Boente-Juncal; Celia Costas; M. Louzao; Luis Botana. 2020. "Detection of Cyclic Imine Toxins in Dietary Supplements of Green Lipped Mussels (Perna canaliculus) and in Shellfish Mytilus chilensis." Toxins 12, no. 10: 613.

Journal article
Published: 30 July 2020 in Toxins
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Palytoxin (PLTX) is one of the most poisonous substances known to date and considered as an emergent toxin in Europe. Palytoxin binds to the Na+-K+ ATPase, converting the enzyme in a permeant cation channel. This toxin is known for causing human fatal intoxications associated with the consumption of contaminated fish and crustaceans such as crabs, groupers, mackerel, and parrotfish. Human intoxications by PLTX after consumption of contaminated fishery products are a serious health issue and can be fatal. Different reports have previously explored the acute oral toxicity of PLTX in mice. Although the presence of palytoxin in marine products is currently not regulated in Europe, the European Food Safety Authority expressed its opinion on PLTX and demanded assessment for chronic toxicity studies of this potent marine toxin. In this study, the chronic toxicity of palytoxin was evaluated after oral administration to mice by gavage during a 28-day period. After chronic exposure of mice to the toxin, a lethal dose 50 (LD50) of 0.44 µg/kg of PLTX and a No-Observed-Adverse-Effect Level (NOAEL) of 0.03 µg/kg for repeated daily oral administration of PLTX were determined. These results indicate a much higher chronic toxicity of PLTX and a lower NOAEL than that previously described in shorter treatment periods, pointing out the need to further reevaluate the levels of this compound in marine products.

ACS Style

Andrea Boente-Juncal; Sandra Raposo-García; Carmen Vale; M. Carmen Louzao; Paz Otero; Luis M. Botana. In Vivo Evaluation of the Chronic Oral Toxicity of the Marine Toxin Palytoxin. Toxins 2020, 12, 489 .

AMA Style

Andrea Boente-Juncal, Sandra Raposo-García, Carmen Vale, M. Carmen Louzao, Paz Otero, Luis M. Botana. In Vivo Evaluation of the Chronic Oral Toxicity of the Marine Toxin Palytoxin. Toxins. 2020; 12 (8):489.

Chicago/Turabian Style

Andrea Boente-Juncal; Sandra Raposo-García; Carmen Vale; M. Carmen Louzao; Paz Otero; Luis M. Botana. 2020. "In Vivo Evaluation of the Chronic Oral Toxicity of the Marine Toxin Palytoxin." Toxins 12, no. 8: 489.

Journal article
Published: 15 July 2020 in Marine Drugs
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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.

ACS Style

Rebeca Alvariño; Eva Alonso; Louis Bornancin; Isabelle Bonnard; Nicolas Inguimbert; Bernard Banaigs; Luis M. Botana. Biological Activities of Cyclic and Acyclic B-Type Laxaphycins in SH-SY5Y Human Neuroblastoma Cells. Marine Drugs 2020, 18, 364 .

AMA Style

Rebeca Alvariño, Eva Alonso, Louis Bornancin, Isabelle Bonnard, Nicolas Inguimbert, Bernard Banaigs, Luis M. Botana. Biological Activities of Cyclic and Acyclic B-Type Laxaphycins in SH-SY5Y Human Neuroblastoma Cells. Marine Drugs. 2020; 18 (7):364.

Chicago/Turabian Style

Rebeca Alvariño; Eva Alonso; Louis Bornancin; Isabelle Bonnard; Nicolas Inguimbert; Bernard Banaigs; Luis M. Botana. 2020. "Biological Activities of Cyclic and Acyclic B-Type Laxaphycins in SH-SY5Y Human Neuroblastoma Cells." Marine Drugs 18, no. 7: 364.

Journal article
Published: 10 May 2020 in Chemosphere
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Marine and freshwater toxins contaminate water resources, shellfish and aquaculture products, causing a broad range of toxic effects in humans and animals. Different core-shell nanoparticles were tested as a new sorbent for removing marine and freshwater toxins from liquid media. Water solutions were contaminated with 20 μg/L of marine toxins and up to 50 μg/L of freshwater toxins and subsequently treated with 250 or 125 mg/L of nanoparticles. Under these conditions, carbon nanoparticles removed around 70% of saxitoxins, spirolides, and azaspiracids, and up to 38% of diarrheic shellfish poisoning toxins. In the case of freshwater toxins, the 85% of microcystin LR was eliminated; other cyclic peptide toxins were also removed in a high percentage. Marine toxins were adsorbed in the first 5 min of contact, while for freshwater toxins it was necessary 60 min to reach the maximum adsorption. Toxins were recovered by extraction from nanoparticles with different solvents. Gymnodinium catenatum, Prorocentrum lima, and Microcystis aeruginosa cultures were employed to test the ability of nanoparticles to adsorb toxins in a real environment, and the same efficacy to remove toxins was observed in these conditions. These results suggest the possibility of using the nanotechnology in the treatment of contaminated water or in chemical analysis applications.

ACS Style

Jesús M. González-Jartín; Lisandra De Castro Alves; Amparo Alfonso; Y. Piñeiro; Susana Yáñez Vilar; Inés Rodríguez; Manuel González Gomez; Zulema Vargas Osorio; María J. Sainz; Mercedes R. Vieytes; J. Rivas; Luis M. Botana. Magnetic nanostructures for marine and freshwater toxins removal. Chemosphere 2020, 256, 127019 .

AMA Style

Jesús M. González-Jartín, Lisandra De Castro Alves, Amparo Alfonso, Y. Piñeiro, Susana Yáñez Vilar, Inés Rodríguez, Manuel González Gomez, Zulema Vargas Osorio, María J. Sainz, Mercedes R. Vieytes, J. Rivas, Luis M. Botana. Magnetic nanostructures for marine and freshwater toxins removal. Chemosphere. 2020; 256 ():127019.

Chicago/Turabian Style

Jesús M. González-Jartín; Lisandra De Castro Alves; Amparo Alfonso; Y. Piñeiro; Susana Yáñez Vilar; Inés Rodríguez; Manuel González Gomez; Zulema Vargas Osorio; María J. Sainz; Mercedes R. Vieytes; J. Rivas; Luis M. Botana. 2020. "Magnetic nanostructures for marine and freshwater toxins removal." Chemosphere 256, no. : 127019.

Journal article
Published: 09 May 2020 in Toxins
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Tetrodotoxin (TTX) is a potent natural toxin causative of human food intoxications that shares its mechanism of action with the paralytic shellfish toxin saxitoxin (STX). Both toxins act as potent blockers of voltage-gated sodium channels. Although human intoxications by TTX were initially described in Japan, nowadays increasing concern about the regulation of this toxin in Europe has emerged due to its detection in fish and mollusks captured in European waters. Currently, TTX is only regularly monitored in Dutch fishery products. However, the European Food Safety Authority (EFSA) has established a safety level of 44 µg/kg TTX as the amount of toxin that did not cause adverse effects in humans. This level was extrapolated considering initial data on its acute oral toxicity and EFSA remarked the need for chronic toxicity studies to further reduce the uncertainty of future toxin regulations. Thus, in this work, we evaluated the oral chronic toxicity of TTX using the safety levels initially recommended by EFSA in order to exclude potential human health risks associated with the worldwide expanding presence of TTX. Using internationally recommended guidelines for the assessment of oral chronic toxicity, the data provided here support the proposed safety level for TTX as low enough to prevent human adverse effects of TTX even after chronic daily exposure to the toxin. However, the combination of TTX with STX at doses above the maximal exposure level of 5.3 µg/kg body weight derived by EFSA increased the lethality of TTX, thus confirming that both TTX and paralytic shellfish toxins should be taken into account to assess human health risks.

ACS Style

Andrea Boente-Juncal; Paz Otero; Inés Rodríguez; Mercedes Camiña; Mercedes Rodriguez-Vieytes; Carmen Vale; Luis M. Botana. Oral Chronic Toxicity of the Safe Tetrodotoxin Dose Proposed by the European Food Safety Authority and Its Additive Effect with Saxitoxin. Toxins 2020, 12, 312 .

AMA Style

Andrea Boente-Juncal, Paz Otero, Inés Rodríguez, Mercedes Camiña, Mercedes Rodriguez-Vieytes, Carmen Vale, Luis M. Botana. Oral Chronic Toxicity of the Safe Tetrodotoxin Dose Proposed by the European Food Safety Authority and Its Additive Effect with Saxitoxin. Toxins. 2020; 12 (5):312.

Chicago/Turabian Style

Andrea Boente-Juncal; Paz Otero; Inés Rodríguez; Mercedes Camiña; Mercedes Rodriguez-Vieytes; Carmen Vale; Luis M. Botana. 2020. "Oral Chronic Toxicity of the Safe Tetrodotoxin Dose Proposed by the European Food Safety Authority and Its Additive Effect with Saxitoxin." Toxins 12, no. 5: 312.

Journal article
Published: 24 January 2020 in Toxicon
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Palytoxin is an emergent toxin in Europe and one of the most toxic substances know to date. The toxin disrupts the physiological functioning of the Na+/K+-ATPase converting the enzyme in a permeant cation channel. Human intoxications by PLTX after consumption of contaminated fishery products are a serious health issue and can be fatal. Several reports have previously investigated the oral and intraperitoneal toxicity of PLTX in mice. However, in all cases short observation periods (24 and 48 h) after toxin administration were evaluated. In this work, single oral or intraperitoneal doses of PLTX were administered to healthy mice and surviving animals were followed up for 96 h. The data obtained here allowed us to calculate the oral and intraperitoneal lethal doses 50 (LD50) which were in the range of the values previously described. Surprisingly, the oral NOAEL for PLTX was more than 10 times lower than that previously described, a fact that indicates the need for the reevaluation of the levels of the toxin in edible fishery products.

ACS Style

Andrea Boente-Juncal; Carmen Vale; Mercedes Camiña; J. Manuel Cifuentes; Mercedes R. Vieytes; Luis M. Botana. Reevaluation of the acute toxicity of palytoxin in mice: Determination of lethal dose 50 (LD50) and No-observed-adverse-effect level (NOAEL). Toxicon 2020, 177, 16 -24.

AMA Style

Andrea Boente-Juncal, Carmen Vale, Mercedes Camiña, J. Manuel Cifuentes, Mercedes R. Vieytes, Luis M. Botana. Reevaluation of the acute toxicity of palytoxin in mice: Determination of lethal dose 50 (LD50) and No-observed-adverse-effect level (NOAEL). Toxicon. 2020; 177 ():16-24.

Chicago/Turabian Style

Andrea Boente-Juncal; Carmen Vale; Mercedes Camiña; J. Manuel Cifuentes; Mercedes R. Vieytes; Luis M. Botana. 2020. "Reevaluation of the acute toxicity of palytoxin in mice: Determination of lethal dose 50 (LD50) and No-observed-adverse-effect level (NOAEL)." Toxicon 177, no. : 16-24.

Journal article
Published: 22 July 2019 in Scientific Reports
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Amparo Alfonso; Jeremías Bayón; Sandra Gegunde; Eva Alonso; Rebeca Alvariño; Melisa Santás-Álvarez; Ana Testa-Fernández; Ramón Rios-Vázquez; Carlos González-Juanatey; Luis M. Botana. High Serum Cyclophilin C levels as a risk factor marker for Coronary Artery Disease. Scientific Reports 2019, 9, 1 .

AMA Style

Amparo Alfonso, Jeremías Bayón, Sandra Gegunde, Eva Alonso, Rebeca Alvariño, Melisa Santás-Álvarez, Ana Testa-Fernández, Ramón Rios-Vázquez, Carlos González-Juanatey, Luis M. Botana. High Serum Cyclophilin C levels as a risk factor marker for Coronary Artery Disease. Scientific Reports. 2019; 9 (1):1.

Chicago/Turabian Style

Amparo Alfonso; Jeremías Bayón; Sandra Gegunde; Eva Alonso; Rebeca Alvariño; Melisa Santás-Álvarez; Ana Testa-Fernández; Ramón Rios-Vázquez; Carlos González-Juanatey; Luis M. Botana. 2019. "High Serum Cyclophilin C levels as a risk factor marker for Coronary Artery Disease." Scientific Reports 9, no. 1: 1.

Journal article
Published: 05 July 2019 in Toxins
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The occurrence of marine harmful algae is increasing worldwide and, therefore, the accumulation of lipophilic marine toxins from harmful phytoplankton represents a food safety threat in the shellfish industry. Galicia, which is a commercially important EU producer of edible bivalve mollusk have been subjected to recurring cases of mussel farm closures, in the last decades. This work aimed to study the toxic profile of commercial mussels (Mytilus galloprovincialis) in order to establish a potential risk when ingested. For this, a total of 41 samples of mussels farmed in 3 Rías (Ares-Sada, Arousa, and Pontevedra) and purchased in 5 local markets were analyzed by liquid chromatography tandem mass spectrometry (LC–MS/MS). Chromatograms showed the presence of okadaic acid (OA), dinophysistoxin-2 (DTX-2), pectenotoxin-2 (PTX-2), azaspiracid-2 (AZA-2), and the emerging toxins 13-desmethyl spirolide C (SPX-13), and pinnatoxin-G (PnTX-G). Quantification of each toxin was determined using their own standard calibration in the range 0.1%–50 ng/mL (R2 > 0.99) and by considering the toxin recovery (62–110%) and the matrix correction (33–211%). Data showed that OA and DTX-2 (especially in the form of esters) are the main risk in Galician mollusks, which was detected in 38 samples (93%) and 3 of them exceeded the legal limit (160 µg/kg), followed by SPX-13 that was detected in 19 samples (46%) in quantities of up to 28.9 µg/kg. Analysis from PTX-2, AZA-2, and PnTX-G showed smaller amounts. Fifteen samples (37%) were positive for PTX-2 (0.7–2.9 µg/kg), 12 samples (29%) for AZA-2 (0.1–1.8 µg/kg), and PnTX-G was detected in 5 mussel samples (12%) (0.4 µg/kg–0.9 µg/kg). This is the first time Galician mollusk was contaminated with PnTX-G. Despite results indicating that this toxin was not a potential risk through the mussel ingestion, it should be considered in the shellfish safety monitoring programs through the LC–MS/MS methods.

ACS Style

Paz Otero; Natalia Miguéns; Inés Rodríguez; Luis M. Botana. LC–MS/MS Analysis of the Emerging Toxin Pinnatoxin-G and High Levels of Esterified OA Group Toxins in Galician Commercial Mussels. Toxins 2019, 11, 394 .

AMA Style

Paz Otero, Natalia Miguéns, Inés Rodríguez, Luis M. Botana. LC–MS/MS Analysis of the Emerging Toxin Pinnatoxin-G and High Levels of Esterified OA Group Toxins in Galician Commercial Mussels. Toxins. 2019; 11 (7):394.

Chicago/Turabian Style

Paz Otero; Natalia Miguéns; Inés Rodríguez; Luis M. Botana. 2019. "LC–MS/MS Analysis of the Emerging Toxin Pinnatoxin-G and High Levels of Esterified OA Group Toxins in Galician Commercial Mussels." Toxins 11, no. 7: 394.

Journal article
Published: 30 May 2019 in Marine Drugs
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So far, the Futuna Islands located in the Central Indo-Pacific Ocean have not been inventoried for their diversity in marine sponges and associated chemical diversity. As part of the Tara Pacific expedition, the first chemical investigation of the sponge Narrabeena nigra collected around the Futuna Islands yielded 18 brominated alkaloids: seven new bromotryptamine derivatives 1–7 and one new bromotyramine derivative 8 together with 10 known metabolites of both families 9–18. Their structures were deduced from extensive analyses of nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS) data. In silico metabolite anticipation using the online tool MetWork revealed the presence of a key and minor biosynthetic intermediates. These 18 compounds showed almost no cytotoxic effect up to 10 µM on human neuroblastoma SH-SY5Y and microglia BV2 cells, and some of them exhibited an interesting neuroprotective activity by reducing oxidative damage.

ACS Style

Maria Miguel-Gordo; Sandra Gegunde; Kevin Calabro; Laurence K. Jennings; Amparo Alfonso; Grégory Genta-Jouve; Jean Vacelet; Luis M. Botana; Olivier P. Thomas. Bromotryptamine and Bromotyramine Derivatives from the Tropical Southwestern Pacific Sponge Narrabeena nigra. Marine Drugs 2019, 17, 319 .

AMA Style

Maria Miguel-Gordo, Sandra Gegunde, Kevin Calabro, Laurence K. Jennings, Amparo Alfonso, Grégory Genta-Jouve, Jean Vacelet, Luis M. Botana, Olivier P. Thomas. Bromotryptamine and Bromotyramine Derivatives from the Tropical Southwestern Pacific Sponge Narrabeena nigra. Marine Drugs. 2019; 17 (6):319.

Chicago/Turabian Style

Maria Miguel-Gordo; Sandra Gegunde; Kevin Calabro; Laurence K. Jennings; Amparo Alfonso; Grégory Genta-Jouve; Jean Vacelet; Luis M. Botana; Olivier P. Thomas. 2019. "Bromotryptamine and Bromotyramine Derivatives from the Tropical Southwestern Pacific Sponge Narrabeena nigra." Marine Drugs 17, no. 6: 319.

Journal article
Published: 29 May 2019 in Toxins
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Tetrodotoxin (TTX) is an extremely toxic marine compound produced by different genera of bacteria that can reach humans through ingestion mainly of pufferfish but also of other contaminated fish species, marine gastropods or bivalves. TTX blocks voltage-gated sodium channels inhibiting neurotransmission, which in severe cases triggers cardiorespiratory failure. Although TTX has been responsible for many human intoxications limited toxicological data are available. The recent expansion of TTX from Asian to European waters and diversification of TTX-bearing organisms entail an emerging risk of food poisoning. This study is focused on the acute toxicity assessment of TTX administered to mice by oral gavage following macroscopic and microscopic studies. Necropsy revealed that TTX induced stomach swelling 2 h after administration, even though no ultrastructural alterations were further detected. However, transmission electron microscopy images showed an increase of lipid droplets in hepatocytes, swollen mitochondria in spleens, and alterations of rough endoplasmic reticulum in intestines as hallmarks of the cellular damage. These findings suggested that gastrointestinal effects should be considered when evaluating human TTX poisoning.

ACS Style

Paula Abal; M. Carmen Louzao; Natalia Vilariño; Mercedes R. Vieytes; Luis M. Botana. Acute Toxicity Assessment: Macroscopic and Ultrastructural Effects in Mice Treated with Oral Tetrodotoxin. Toxins 2019, 11, 305 .

AMA Style

Paula Abal, M. Carmen Louzao, Natalia Vilariño, Mercedes R. Vieytes, Luis M. Botana. Acute Toxicity Assessment: Macroscopic and Ultrastructural Effects in Mice Treated with Oral Tetrodotoxin. Toxins. 2019; 11 (6):305.

Chicago/Turabian Style

Paula Abal; M. Carmen Louzao; Natalia Vilariño; Mercedes R. Vieytes; Luis M. Botana. 2019. "Acute Toxicity Assessment: Macroscopic and Ultrastructural Effects in Mice Treated with Oral Tetrodotoxin." Toxins 11, no. 6: 305.

Journal article
Published: 29 May 2019 in Toxins
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Tetrodotoxin (TTX) is a potent alkaloid typically from tropical ecosystems, but in the last decade its presence has been more pronounced in the temperate waters of the Atlantic. In its last scientific opinion, the European Food Safety Authority (EFSA) stressed the need for data regarding TTX prevalence in European waters. To address EFSA’s concerns, benthic organisms such as mollusks, crustaceans, echinoderms and fish with different feeding habits were collected along the Portuguese continental coast, islands (São Miguel, Azores, and Madeira) and the northwestern Moroccan coast. A total of 165 samples were analyzed by ultra high performance liquid chromatography high resolution mass spectrometry (UHPLC-HRMS) and ultra high performance chromatography mass spectrometry (UHPLC-MS/MS). Geographical tendencies were detected as follows, by descending order: S. Miguel Island (Azores), Moroccan coast, Madeira Island and Portuguese continental coast. The toxin amounts detected were significant, above the Dutch limit value established in 2017, showing the importance and the need for continuity of these studies to gain more knowledge about the prevalence of these toxins, unraveling new vectors, in order to better assess human health risk. This work represents a general overview of new TTX bearers (7) most of them in gastropods (Patella depressa, Nucella lapillus, Onchidella celtica and Aplysia depilans), followed by echinoderms (Echinus esculentus and Ophidiaster ophidianus) and puffer fish Sphoeroides marmoratus.

ACS Style

Marisa Silva; Inés Rodríguez; Aldo Barreiro; Manfred Kaufmann; Ana Isabel Neto; Meryem Hassouani; Brahim Sabour; Amparo Alfonso; Luis M. Botana; Vitor Vasconcelos. Tetrodotoxins Occurrence in Non-Traditional Vectors of the North Atlantic Waters (Portuguese Maritime Territory, and Morocco Coast). Toxins 2019, 11, 306 .

AMA Style

Marisa Silva, Inés Rodríguez, Aldo Barreiro, Manfred Kaufmann, Ana Isabel Neto, Meryem Hassouani, Brahim Sabour, Amparo Alfonso, Luis M. Botana, Vitor Vasconcelos. Tetrodotoxins Occurrence in Non-Traditional Vectors of the North Atlantic Waters (Portuguese Maritime Territory, and Morocco Coast). Toxins. 2019; 11 (6):306.

Chicago/Turabian Style

Marisa Silva; Inés Rodríguez; Aldo Barreiro; Manfred Kaufmann; Ana Isabel Neto; Meryem Hassouani; Brahim Sabour; Amparo Alfonso; Luis M. Botana; Vitor Vasconcelos. 2019. "Tetrodotoxins Occurrence in Non-Traditional Vectors of the North Atlantic Waters (Portuguese Maritime Territory, and Morocco Coast)." Toxins 11, no. 6: 306.

Journal article
Published: 03 May 2019 in Food Chemistry
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Mycotoxins are toxic compounds that can be present in feed, food and beverages. In this work, 25 magnetic nanostructured materials were developed to remove the main types of mycotoxins from liquid food matrices. The efficiency for binding mycotoxins from contaminated aqueous solutions was studied. Nanocomposites (diameters lower to 15 μm) composed of mixtures of activated carbon, bentonite and aluminium oxide were able to eliminate up to 87% of mycotoxins with an adsorption efficiency of 450 µg/g. On the other hand, spheres with sizes below 3 mm and composed by biopolymers and activated carbon or graphene oxide removed up to 70% of mycotoxins (adsorption of 598 ng/g). These particles were tested for beer detoxification and, spheres composed of alginate and activated carbon or pectin maintain the ability to eliminate toxin from this beverage. Hence, this technology could be a useful tool for the food industry.

ACS Style

Jesús M. González-Jartín; Lisandra De Castro Alves; Amparo Alfonso; Y. Piñeiro; Susana Yáñez Vilar; Manuel González Gomez; Zulema Vargas Osorio; María J. Sainz; Mercedes R. Vieytes; J. Rivas; Luis M. Botana. Detoxification agents based on magnetic nanostructured particles as a novel strategy for mycotoxin mitigation in food. Food Chemistry 2019, 294, 60 -66.

AMA Style

Jesús M. González-Jartín, Lisandra De Castro Alves, Amparo Alfonso, Y. Piñeiro, Susana Yáñez Vilar, Manuel González Gomez, Zulema Vargas Osorio, María J. Sainz, Mercedes R. Vieytes, J. Rivas, Luis M. Botana. Detoxification agents based on magnetic nanostructured particles as a novel strategy for mycotoxin mitigation in food. Food Chemistry. 2019; 294 ():60-66.

Chicago/Turabian Style

Jesús M. González-Jartín; Lisandra De Castro Alves; Amparo Alfonso; Y. Piñeiro; Susana Yáñez Vilar; Manuel González Gomez; Zulema Vargas Osorio; María J. Sainz; Mercedes R. Vieytes; J. Rivas; Luis M. Botana. 2019. "Detoxification agents based on magnetic nanostructured particles as a novel strategy for mycotoxin mitigation in food." Food Chemistry 294, no. : 60-66.

Journal article
Published: 26 March 2019 in Bioorganic & Medicinal Chemistry
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Five new laxaphycins were isolated and fully characterised from the bloom forming cyanobacteria Anabaena torulosa sampled from Moorea, French Polynesia: three acyclic laxaphycin A-type peptides, acyclolaxaphycin A (1), [des-Gly11]acyclolaxaphycin A (2) and [des-(Leu10-Gly11)]acyclolaxaphycin A (3), as well as two cyclic ones, [l-Val8]laxaphycin A (4) and [d-Val9]laxaphycin A (5). The absolute configuration of the amino acids, established using advanced Marfey’s analysis for compounds 2–5, highlights a conserved stereochemistry at the Cα carbons of the peptide ring that is characteristic of this family. To the best of our knowledge, this is the first report of acyclic analogues within the laxaphycin A-type peptides. Whether these linear laxaphycins with the aliphatic β-amino acid on the N-terminal are biosynthetic precursors or compounds obtained after enzymatic hydrolysis of the macrocycle is discussed. Biological evaluation of the new compounds together with the already known laxaphycin A shows that [l-Val8]laxaphycin A, [d-Val9]laxaphycin A and [des-Gly11]acyclolaxaphycin induce cellular toxicity whereas laxaphycin A and des-[(Leu10-Gly11)]acyclolaxaphycin A do not affect the cellular viability. An analysis of cellular death shows that the active peptides do not induce apoptosis or necrosis but instead, involve the autophagy pathway.

ACS Style

Louis Bornancin; Eva Alonso; Rebeca Alvariño; Nicolas Inguimbert; Isabelle Bonnard; Luis M Botana; Bernard Banaigs. Structure and biological evaluation of new cyclic and acyclic laxaphycin-A type peptides. Bioorganic & Medicinal Chemistry 2019, 27, 1966 -1980.

AMA Style

Louis Bornancin, Eva Alonso, Rebeca Alvariño, Nicolas Inguimbert, Isabelle Bonnard, Luis M Botana, Bernard Banaigs. Structure and biological evaluation of new cyclic and acyclic laxaphycin-A type peptides. Bioorganic & Medicinal Chemistry. 2019; 27 (10):1966-1980.

Chicago/Turabian Style

Louis Bornancin; Eva Alonso; Rebeca Alvariño; Nicolas Inguimbert; Isabelle Bonnard; Luis M Botana; Bernard Banaigs. 2019. "Structure and biological evaluation of new cyclic and acyclic laxaphycin-A type peptides." Bioorganic & Medicinal Chemistry 27, no. 10: 1966-1980.

Journal article
Published: 22 March 2019 in Nature Chemistry
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The architecture and bioactivity of natural products frequently serve as embarkation points for the exploration of biologically relevant chemical space. Total synthesis followed by derivative synthesis has historically enabled a deeper understanding of structure–activity relationships. However, synthetic strategies towards a natural product are not always guided by hypotheses regarding the structural features required for bioactivity. Here, we report an approach to natural product total synthesis that we term ‘pharmacophore-directed retrosynthesis’. A hypothesized, pharmacophore of a natural product is selected as an early synthetic target and this dictates the retrosynthetic analysis. In an ideal application, sequential increases in the structural complexity of this minimal structure enable development of a structure–activity relationship profile throughout the course of the total synthesis effort. This approach enables the identification of simpler congeners retaining bioactivity at a much earlier stage of a synthetic effort, as demonstrated here for the spongiane diterpenoid, gracilin A, leading to simplified derivatives with potent neuroprotective and immunosuppressive activity. Pharmacophore-directed retrosynthesis targets a potential pharmacophore from early on in a natural product synthesis and incremental increases in the complexity of this minimal structure enable a SAR profile to develop over the course of the campaign. The method is applied to gracilin A, finding simplified derivatives displaying potent immunosuppressive effects or selective neuroprotective effects in cell-based assays.

ACS Style

Mikail E. Abbasov; Rebeca Alvariño; Christian M. Chaheine; Eva Alonso; Jon A. Sánchez; Michael L. Conner; Amparo Alfonso; Marcel Jaspars; Luis M. Botana; Daniel Romo. Simplified immunosuppressive and neuroprotective agents based on gracilin A. Nature Chemistry 2019, 11, 342 -350.

AMA Style

Mikail E. Abbasov, Rebeca Alvariño, Christian M. Chaheine, Eva Alonso, Jon A. Sánchez, Michael L. Conner, Amparo Alfonso, Marcel Jaspars, Luis M. Botana, Daniel Romo. Simplified immunosuppressive and neuroprotective agents based on gracilin A. Nature Chemistry. 2019; 11 (4):342-350.

Chicago/Turabian Style

Mikail E. Abbasov; Rebeca Alvariño; Christian M. Chaheine; Eva Alonso; Jon A. Sánchez; Michael L. Conner; Amparo Alfonso; Marcel Jaspars; Luis M. Botana; Daniel Romo. 2019. "Simplified immunosuppressive and neuroprotective agents based on gracilin A." Nature Chemistry 11, no. 4: 342-350.