Microseiramide from the freshwater cyanobacterium Microseira sp. UIC 10445. (September 2015)

• Record Type: Journal Article
• Authors: Luo, Shangwen; Krunic, Aleksej; Chlipala, George E.; Orjala, Jimmy
• Is Part Of: Phytochemistry letters. Volume 13(2015:Sep.)
• Page Start: 47
• Page End: 52
• Publication Date: 2015-09
• Subjects: Cyanobacteria -- Microseira sp. -- Cyclic hetapeptide -- Microseiramide; Botanical chemistry -- Periodicals; Chimie végétale -- Périodiques; 572.205
• DOI: 10.1016/j.phytol.2015.05.003
• Languages: English
• ISSNs: 1874-3900

Abstract

Graphical abstract: Microseiramide, a cyclic heptapeptide, was isolated from a sample of the freshwater cyanobacterium Microseira sp. UIC 10445. It is the first cyclic peptide reported from a Microseira sp. Highlights: We isolated a cyclic hetapeptide, named microseiramide, from a freshwater cyanobacterium UIC 10445. UIC 10445 was identified as a member of the recently described genus Microseira . Microseiramide is the first cyclic peptide reported from a Microseira sp. Abstract: Microseiramide (1 ), a cyclic heptapeptide, was isolated from a sample of the freshwater cyanobacterium Microseira sp. UIC 10445 collected in a shallow lake in Northern Indiana. Taxonomic identification of UIC 10445 was performed by a combination of morphological and phylogenetic characterization. Phylogenetic analysis revealed that UIC 10445 was a member of the recently described genus Microseira, which is phylogenetically distinct from the morphologically similar genera, Moorea and Lyngbya . The planar structure of microseiramide (1 ) was determined by extensive 1D and 2D NMR experiments as well as HRESIMS analysis. The absolute configurations of amino acid residues were determined using acid hydrolysis followed by the advanced Marfey's analysis. Microseiramide (1 ) is the first cyclic peptide reported from a Microseira sp., and the structure of microseiramide (1 ) is distinct from the previously known metabolites from cyanobacteria of the genera Moorea and Lyngbya .