Mar. Drugs 2011, 9(12), 2809-2817; doi:10.3390/md9122809
Article

Aurantoside J: a New Tetramic Acid Glycoside from Theonella swinhoei. Insights into the Antifungal Potential of Aurantosides

Rihab F. Angawi1,† email, Giorgio Bavestrello2 email, Barbara Calcinai2 email, Henny Adeleida Dien3 email, Giovanna Donnarumma4 email, Maria Antonietta Tufano4 email, Iole Paoletti4 email, Elena Grimaldi4 email, Giuseppina Chianese1 email, Ernesto Fattorusso1 email and Orazio Taglialatela-Scafati1,* email
1 The NeaNat Group, Department of Natural Compounds Chemistry, University of Naples “Federico II”, Via D. Montesano 49, 80131 Napoli, Italy 2 Department of Marine Sciences, Polytechnic University of Marche, Via Brecce Bianche, 60131 Ancona, Italy 3 Faculty of Fishery and Marine Science, Sam Ratulangi University, Manado, Indonesia 4 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
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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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Cite This Article

MDPI and ACS Style

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.

AMA Style

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. Marine Drugs. 2011; 9(12):2809-2817.

Chicago/Turabian Style

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.

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