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Aurantoside J: a New Tetramic Acid Glycoside from Theonella swinhoei. Insights into the Antifungal Potential of Aurantosides
The NeaNat Group, Department of Natural Compounds Chemistry, University of Naples “Federico II”, Via D. Montesano 49, 80131 Napoli, Italy
Department of Marine Sciences, Polytechnic University of Marche, Via Brecce Bianche, 60131 Ancona, Italy
Faculty of Fishery and Marine Science, Sam Ratulangi University, Manado, Indonesia
Department of Experimental Medicine, Section of Microbiology and Clinical Microbiology, Second University of Naples, Via Costantinopoli, 16-80138 Naples, Italy
Department of Chemistry, King Abdulaziz University, Jeddah 21589, Saudi Arabia.
* Author to whom correspondence should be addressed.
Received: 3 November 2011; in revised form: 7 December 2011 / Accepted: 15 December 2011 / Published: 20 December 2011
Abstract: The chemical investigation of an Indonesian specimen of Theonella swinhoei afforded four aurantosides, one of which, aurantoside J (5), is a new compound. The structure of this metabolite, exhibiting the unprecedented N-α-glycosidic linkage between the pentose and the tetramate units, has been determined through detailed spectroscopic analysis. The four obtained aurantosides have been tested against five fungal strains (four Candida and one Fusarium) responsible of invasive infections in immuno-compromised patients. The non-cytotoxic aurantoside I (4) was the single compound to show an excellent potency against all the tested strains, thus providing valuable insights about the antifungal potential of this class of compounds and the structure-activity relationships.
Keywords: Theonella swhinoei; aurantosides; N-glycosides; antifungal activity
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Angawi, R.F.; Bavestrello, G.; Calcinai, B.; Dien, H.A.; Donnarumma, G.; Tufano, M.A.; Paoletti, I.; Grimaldi, E.; Chianese, G.; Fattorusso, E.; Taglialatela-Scafati, O. Aurantoside J: a New Tetramic Acid Glycoside from Theonella swinhoei. Insights into the Antifungal Potential of Aurantosides. Mar. Drugs 2011, 9, 2809-2817.
Angawi RF, Bavestrello G, Calcinai B, Dien HA, Donnarumma G, Tufano MA, Paoletti I, Grimaldi E, Chianese G, Fattorusso E, Taglialatela-Scafati O. Aurantoside J: a New Tetramic Acid Glycoside from Theonella swinhoei. Insights into the Antifungal Potential of Aurantosides. Marine Drugs. 2011; 9(12):2809-2817.
Angawi, Rihab F.; Bavestrello, Giorgio; Calcinai, Barbara; Dien, Henny Adeleida; Donnarumma, Giovanna; Tufano, Maria Antonietta; Paoletti, Iole; Grimaldi, Elena; Chianese, Giuseppina; Fattorusso, Ernesto; Taglialatela-Scafati, Orazio. 2011. "Aurantoside J: a New Tetramic Acid Glycoside from Theonella swinhoei. Insights into the Antifungal Potential of Aurantosides." Mar. Drugs 9, no. 12: 2809-2817.