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. 2015 Sep 1:13:47-52.
doi: 10.1016/j.phytol.2015.05.003.

Microseiramide from the Freshwater Cyanobacterium Microseira sp. UIC 10445

Affiliations

Microseiramide from the Freshwater Cyanobacterium Microseira sp. UIC 10445

Shangwen Luo et al. Phytochem Lett. .

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.

Keywords: Cyanobacteria; Microseira sp; cyclic hetapeptide; microseiramide.

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Figures

Figure 1
Figure 1
Key 2D NMR correlations of microseiramide (1).
Figure 1
Figure 1
Key 2D NMR correlations of microseiramide (1).
Figure 2
Figure 2
Q-TOF MS/MS fragmentation analysis of microseiramide (1).
Figure 3
Figure 3
Neighbor-joining (NJ) phylogenetic tree based on the 16S rRNA gene sequence. Species and strain numbers are given with accession numbers in parentheses. Reference strains obtained from Bergey’s Manual were denoted with an asterisk (*). (Castenholz, 2001) Reference strains characterized by Engene et al were denoted with two asterisks (**). (Engene et al., 2012) Only bootstrap values greater than or equal to 75% are displayed.

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