Aurantoside J: a new tetramic acid glycoside from Theonella swinhoei. Insights into the antifungal potential of aurantosides.

Marine Drugs
Rihab F AngawiOrazio Taglialatela-Scafati

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.

References

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Dec 8, 2009·Journal of Natural Products·Rihab F AngawiOrazio Taglialatela-Scafati

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Citations

Mar 24, 2016·Biochimica Et Biophysica Acta·Rafael Atillo EspirituShigeki Matsunaga
Jul 3, 2018·Chemical & Pharmaceutical Bulletin·Shanji LiYoshiji Takemoto
Oct 3, 2018·Marine Drugs·Sumi ShresthaGavin R Flematti
Dec 25, 2012·Natural Product Reports·John W BluntMichèle R Prinsep
Sep 26, 2013·Beilstein Journal of Organic Chemistry·Annamaria SinisiOrazio Taglialatela-Scafati
Dec 17, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Joana CardosoEugénia Pinto
May 1, 2021·Marine Drugs·Disha VarijakzhanChou-Min Chong

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Methods Mentioned

BETA
glycosylation
NMR

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