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Investigating the Antiparasitic Potential of the Marine Sesquiterpene Avarone, Its Reduced Form Avarol, and the Novel Semisynthetic Thiazinoquinone Analogue Thiazoavarone

The chemical analysis of the sponge Dysidea avara afforded the known sesquiterpene quinone avarone, along with its reduced form avarol. To further explore the role of the thiazinoquinone scaffold as an antiplasmodial, antileishmanial and antischistosomal agent, we converted the quinone avarone into...

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Autores principales: Imperatore, Concetta, Gimmelli, Roberto, Persico, Marco, Casertano, Marcello, Guidi, Alessandra, Saccoccia, Fulvio, Ruberti, Giovina, Luciano, Paolo, Aiello, Anna, Parapini, Silvia, Avunduk, Sibel, Basilico, Nicoletta, Fattorusso, Caterina, Menna, Marialuisa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7074381/
https://www.ncbi.nlm.nih.gov/pubmed/32075136
http://dx.doi.org/10.3390/md18020112
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author Imperatore, Concetta
Gimmelli, Roberto
Persico, Marco
Casertano, Marcello
Guidi, Alessandra
Saccoccia, Fulvio
Ruberti, Giovina
Luciano, Paolo
Aiello, Anna
Parapini, Silvia
Avunduk, Sibel
Basilico, Nicoletta
Fattorusso, Caterina
Menna, Marialuisa
author_facet Imperatore, Concetta
Gimmelli, Roberto
Persico, Marco
Casertano, Marcello
Guidi, Alessandra
Saccoccia, Fulvio
Ruberti, Giovina
Luciano, Paolo
Aiello, Anna
Parapini, Silvia
Avunduk, Sibel
Basilico, Nicoletta
Fattorusso, Caterina
Menna, Marialuisa
author_sort Imperatore, Concetta
collection PubMed
description The chemical analysis of the sponge Dysidea avara afforded the known sesquiterpene quinone avarone, along with its reduced form avarol. To further explore the role of the thiazinoquinone scaffold as an antiplasmodial, antileishmanial and antischistosomal agent, we converted the quinone avarone into the thiazinoquinone derivative thiazoavarone. The semisynthetic compound, as well as the natural metabolites avarone and avarol, were pharmacologically investigated in order to assess their antiparasitic properties against sexual and asexual stages of Plasmodium falciparum, larval and adult developmental stages of Schistosoma mansoni (eggs included), and also against promastigotes and amastigotes of Leishmania infantum and Leishmania tropica. Furthermore, in depth computational studies including density functional theory (DFT) calculations were performed. A toxic semiquinone radical species which can be produced starting both from quinone- and hydroquinone-based compounds could mediate the anti-parasitic effects of the tested compounds.
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spelling pubmed-70743812020-03-20 Investigating the Antiparasitic Potential of the Marine Sesquiterpene Avarone, Its Reduced Form Avarol, and the Novel Semisynthetic Thiazinoquinone Analogue Thiazoavarone Imperatore, Concetta Gimmelli, Roberto Persico, Marco Casertano, Marcello Guidi, Alessandra Saccoccia, Fulvio Ruberti, Giovina Luciano, Paolo Aiello, Anna Parapini, Silvia Avunduk, Sibel Basilico, Nicoletta Fattorusso, Caterina Menna, Marialuisa Mar Drugs Article The chemical analysis of the sponge Dysidea avara afforded the known sesquiterpene quinone avarone, along with its reduced form avarol. To further explore the role of the thiazinoquinone scaffold as an antiplasmodial, antileishmanial and antischistosomal agent, we converted the quinone avarone into the thiazinoquinone derivative thiazoavarone. The semisynthetic compound, as well as the natural metabolites avarone and avarol, were pharmacologically investigated in order to assess their antiparasitic properties against sexual and asexual stages of Plasmodium falciparum, larval and adult developmental stages of Schistosoma mansoni (eggs included), and also against promastigotes and amastigotes of Leishmania infantum and Leishmania tropica. Furthermore, in depth computational studies including density functional theory (DFT) calculations were performed. A toxic semiquinone radical species which can be produced starting both from quinone- and hydroquinone-based compounds could mediate the anti-parasitic effects of the tested compounds. MDPI 2020-02-14 /pmc/articles/PMC7074381/ /pubmed/32075136 http://dx.doi.org/10.3390/md18020112 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Imperatore, Concetta
Gimmelli, Roberto
Persico, Marco
Casertano, Marcello
Guidi, Alessandra
Saccoccia, Fulvio
Ruberti, Giovina
Luciano, Paolo
Aiello, Anna
Parapini, Silvia
Avunduk, Sibel
Basilico, Nicoletta
Fattorusso, Caterina
Menna, Marialuisa
Investigating the Antiparasitic Potential of the Marine Sesquiterpene Avarone, Its Reduced Form Avarol, and the Novel Semisynthetic Thiazinoquinone Analogue Thiazoavarone
title Investigating the Antiparasitic Potential of the Marine Sesquiterpene Avarone, Its Reduced Form Avarol, and the Novel Semisynthetic Thiazinoquinone Analogue Thiazoavarone
title_full Investigating the Antiparasitic Potential of the Marine Sesquiterpene Avarone, Its Reduced Form Avarol, and the Novel Semisynthetic Thiazinoquinone Analogue Thiazoavarone
title_fullStr Investigating the Antiparasitic Potential of the Marine Sesquiterpene Avarone, Its Reduced Form Avarol, and the Novel Semisynthetic Thiazinoquinone Analogue Thiazoavarone
title_full_unstemmed Investigating the Antiparasitic Potential of the Marine Sesquiterpene Avarone, Its Reduced Form Avarol, and the Novel Semisynthetic Thiazinoquinone Analogue Thiazoavarone
title_short Investigating the Antiparasitic Potential of the Marine Sesquiterpene Avarone, Its Reduced Form Avarol, and the Novel Semisynthetic Thiazinoquinone Analogue Thiazoavarone
title_sort investigating the antiparasitic potential of the marine sesquiterpene avarone, its reduced form avarol, and the novel semisynthetic thiazinoquinone analogue thiazoavarone
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7074381/
https://www.ncbi.nlm.nih.gov/pubmed/32075136
http://dx.doi.org/10.3390/md18020112
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