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Fungal growth inhibitory properties of new phytosphingolipid analogues
Author(s) -
Mormeneo D.,
Manresa A.,
Casas J.,
Llebaria A.,
Delgado A.
Publication year - 2008
Publication title -
journal of applied microbiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.889
H-Index - 156
eISSN - 1365-2672
pISSN - 1364-5072
DOI - 10.1111/j.1365-2672.2007.03635.x
Subject(s) - cladosporium cladosporioides , penicillium chrysogenum , candida albicans , aspergillus niger , yeast , stereochemistry , penicillium , biology , saccharomyces cerevisiae , biochemistry , chemistry , microbiology and biotechnology , botany
Aims: To study the growth inhibitory properties of a series of phytosphingosine (PHS) and phytoceramide (PHC) analogues. Methods and Results: A panel of two yeast ( Candida albicans and Saccharomyces cerevisiae ) and six moulds (A spergillus repens , Aspergillus niger , Penicillium chrysogenum , Cladosporium cladosporioides , Arthroderma uncinatum and Penicillium funiculosum ) has been used in this study. A series of new PHS and PHC analogues differing at the sphingoid backbone and the functional group at C1 position were synthesized. Conclusions: Among PHS analogues, 1‐azido derivative 1c, bearing the natural d ‐ ribo stereochemistry, showed a promising growth inhibitory profile. Among PHC analogues, compound 12, with a bulky N ‐pivaloyl group and a Z double bond at C3 position of the sphingoid chain, was the most active growth inhibitor. Minimal inhibitory concentration values were in the range of 23–48 μ mol l −1 for 1c and 44–87 μ mol l −1 for 12. Significance and Impact of the Study: Only scattered data on the antifungal activity of phytosphingolipids have been reported in the literature. This is the first time that a series of analogues of this kind are tested and compared to discern their structural requirements for antifungal activity.