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J Nat Prod. 2014 Sep 26;77(9):2118-23. doi: 10.1021/np500577v. Epub 2014 Sep 12.

MDN-0104, an antiplasmodial betaine lipid from Heterospora chenopodii.

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Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía , Avenida del Conocimiento 34, Parque Tecnológico de Ciencias de la Salud, E-18016, Granada, Spain.


Bioassay-guided fractionation of the crude fermentation extract of Heterospora chenopodii led to the isolation of a novel monoacylglyceryltrimethylhomoserine (1). The structure of this new betaine lipid was elucidated by detailed spectroscopic analysis using one- and two-dimensional NMR experiments and high-resolution mass spectrometry. Compound 1 displayed moderate in vitro antimalarial activity against Plasmodium falciparum, with an IC50 value of 7 μM. This betaine lipid is the first monoacylglyceryltrimethylhomoserine ever reported in the Fungi, and its acyl moiety also represents a novel natural 3-keto fatty acid. The new compound was isolated during a drug discovery program aimed at the identification of new antimalarial leads from a natural product library of microbial extracts. Interestingly, the related fungus Heterospora dimorphospora was also found to produce compound 1, suggesting that species of this genus may be a promising source of monoacylglyceryltrimethylhomoserines.

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