Hassallidin A, a glycosylated lipopeptide with antifungal activity from the cyanobacterium Hassallia sp.
Hassallidin A (1), a new antifungal glycosylated lipopeptide, was isolated from an epilithic cyanobacterium collected in Bellano, Italy, identified as Tolypothrix (basionym Hassallia) species. Chemical, mass spectrometric, and spectroscopic analyses, including one- and two-dimensional NMR, were performed to determine an esterified eight-residue cyclic peptide linked with a carbohydrate and a fatty acid residue. Chiral GC-MS analysis revealed the occurrence of the nonproteinogenic amino acids D-allo-Thr, D-Thr, D-Tyr, D-Gln, and dehydroaminobutyric acid (Dhb) within the peptide moiety. The additional components of hassallidin A could be identified as alpha,beta-dihydroxytetradecanoic acid (Dht) and mannose. This is the first report on a cyclic peptide of cyanobacterial origin that contains both a fatty acid and a carbohydrate moiety. Compound 1 exhibits antifungal activity against Aspergillus fumigatus and Candida albicans with MIC values of 4.8 microg/mL for both test organisms.
Neuhof
Torsten
T
Institut für Chemie, Fak. II, Technische Universität Berlin, 10587 Berlin, Germany.
Schmieder
Peter
P
Preussel
Karina
K
Dieckmann
Ralf
R
Pham
Huong
H
Bartl
Franz
F
von Döhren
Hans
H
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000595:Amino Acid Sequence; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001232:Aspergillus fumigatus / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D000458:Cyanobacteria / Q000737:chemistry*; D006017:Glycolipids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006020:Glycopeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007558:Italy; D055666:Lipopeptides; D008074:Lipoproteins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
D000470:Alkaloids; D000935:Antifungal Agents; D006017:Glycolipids; D006020:Glycopeptides; D055666:Lipopeptides; D008074:Lipoproteins; C501712:hassallidin A