Hofmannolin, a cyanopeptolin from Scytonema hofmanni PCC 7110.
Two depsipeptide metabolites, scyptolin A and B, were reported recently from the axenically grown terrestrial cyanobacterium Scytonema hofmanni PCC 7110. A related, novel depsipeptide was isolated from this Scytonema and designated hofmannolin. The amino acid analysis in context with infrared, mass and 1H/13C-NMR spectroscopies revealed a cyclic depsipeptide structure of M(r) 1073 belonging to the class of cyanopeptolins. Two peculiar features distinguish hofmannolin from other cyanopeptolins: O-methylated tyrosine forms the sixth moiety from the amino terminus, and the N-terminus is blocked by 2-hydroxy-3-methyl-valeric acid, a residue that has not yet been reported as a component in other cyanopeptolins. Preliminary assays of peptidase inhibitory and antimicrobial activities suggested negligible bioactivities for hofmannolin.
Matern
Ute
U
Institut für Biologie II (Mikrobiologie), Albert-Ludwigs-Universität, Schänzle-Strasse 1, D-79104 Freiburg i. Br., Germany. ute.matern@biologie.uni-freiburg.de
Oberer
Lukas
L
Erhard
Marcel
M
Herdman
Michael
M
Weckesser
Jürgen
J
D000595:Amino Acid Sequence; D000890:Anti-Infective Agents / Q000302:isolation & purification / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D000458:Cyanobacteria / Q000737:chemistry* / Q000235:genetics; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D011480:Protease Inhibitors / Q000302:isolation & purification / Q000494:pharmacology; D011487:Protein Conformation; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization / Q000379:methods
D000890:Anti-Infective Agents; C481033:Hofmannolin; D010456:Peptides, Cyclic; D011480:Protease Inhibitors