Cyanopeptolin S, a sulfate-containing depsipeptide from a water bloom of Microcystis sp

A new sulfated, cyclic depsipeptide, called cyanopeptolin S, from Microcystis sp. was isolated from a water bloom in the Auensee/Leipzig (Germany). The depsipeptide had a relative molecular mass of 925 and contained l-arginine, l-threonine, l-isoleucine, N-methyl- l-phenylalanine, a l-glutamic acid-...

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Published inFEMS microbiology letters Vol. 129; no. 2; pp. 129 - 133
Main Authors Jakobi, Clemens, Oberer, Lukas, Quiquerez, Charles, König, Wilfried A., Weckesser, Jürgen
Format Journal Article
LanguageEnglish
Published Elsevier B.V 15.06.1995
Subjects
Depsipeptide
Microcystis sp
Sulfate
Trypsin inhibition
Water bloom
Water bloom
NOE
ROESY
HMBC
TOCSY
HCCORR
COSY
Microcystis sp
Depsipeptide
FABMS
FTIR
Trypsin inhibition
NOESY
Sulfate
GC/MS
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Summary:A new sulfated, cyclic depsipeptide, called cyanopeptolin S, from Microcystis sp. was isolated from a water bloom in the Auensee/Leipzig (Germany). The depsipeptide had a relative molecular mass of 925 and contained l-arginine, l-threonine, l-isoleucine, N-methyl- l-phenylalanine, a l-glutamic acid-δ-aldehyde ring system and a sulfated d-configurated glyceric acid as a side chain. The structure was elucidated by means of two-dimensional 1H and 13C nuclear magnetic resonance spectroscopy, fast atom bombardment mass spectroscopy, Fourier transformed infrared spectroscopy and combined gas-liquid chromatography/mass spectrometry. Cyanopeptolin S inhibited trypsin with an IC 50 ≤ 0.2 μg ml −1.
ISSN:0378-1097
1574-6968
DOI:10.1016/0378-1097(95)00146-V