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

1
The NeaNat Group, Department of Pharmacy, University of Naples “Federico II”, Via D. Montesano 49, 80131 Napoli, Italy
2
Italian Malaria Network, Centro Interuniversitario di Ricerche Sulla Malaria (CIRM), Department of Pharmacy, University of Naples “Federico II”, Via D. Montesano 49, 80131 Napoli, Italy
3
Institute of Biochemistry and Cell Biology, National Research Council, Campus A. Buzzati-Traverso, Via E. Ramarini, 32, 00015 Monterotondo (Roma), Italy
4
Dipartimento di Scienze Biomediche per la Salute, Università di Milano, Via Pascal 36, 20133 Milan, Italy
5
Department Vocational School of Medicinal Health Services, Mugla University, 48187 Mugla, Turkey
6
Dipartimento di Scienze Biomediche, Chirurgiche e Odontoiatriche, Università di Milano, Via Pascal 36, 20133 Milan, Italy
*
Authors to whom correspondence should be addressed.
These authors equally contributed.
Mar. Drugs 2020, 18(2), 112; https://doi.org/10.3390/md18020112
Received: 9 January 2020 / Revised: 6 February 2020 / Accepted: 11 February 2020 / Published: 14 February 2020
(This article belongs to the Special Issue Selected Papers from XVI MaNaPro and XI ECMNP)
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.
Keywords: Dysidea avara; avarone/avarol; redox-active compounds; quinones and hydroquinones; dioxothiazinoquinone; Schistosoma mansoni; Plasmodium falciparum; Leishmania spp.; 3D-SAR analysis; DFT studies Dysidea avara; avarone/avarol; redox-active compounds; quinones and hydroquinones; dioxothiazinoquinone; Schistosoma mansoni; Plasmodium falciparum; Leishmania spp.; 3D-SAR analysis; DFT studies
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Imperatore, C.; Gimmelli, R.; Persico, M.; Casertano, M.; Guidi, A.; Saccoccia, F.; Ruberti, G.; Luciano, P.; Aiello, A.; Parapini, S.; Avunduk, S.; Basilico, N.; Fattorusso, C.; Menna, M. Investigating the Antiparasitic Potential of the Marine Sesquiterpene Avarone, Its Reduced form Avarol, and the Novel Semisynthetic Thiazinoquinone Analogue Thiazoavarone. Mar. Drugs 2020, 18, 112.

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