Schizotrin A; a novel antimicrobial cyclic peptide from a cyanobacterium

A Novel β‐Amino Acid in Cytotoxic Peptides from the Cyanobacterium Tychonema sp.

“…Because of the overlapping 1 H NMR signals of 5-H and 66-H (δ H = 5.03 and 5.00 ppm, respectively) an HMBC correlation between 5-H and C-65 (δ C = 170.4 ppm) could not be detected unambiguously. However, all experimental data and comparison with literature data [3,4,8] led us to conclude that N-acetyl-N-methylleucine is bound through an ester functionality to C-5 of the β-amino acid Atpoa, which gives rise to fragment A. 1 H and 13 C NMR spectroscopic data indicated a second aromatic moiety, which consisted of a 1,4-disubstituted benzene ring as shown by characteristic resonances for 25/ 26-H (δ H = 7.10 ppm) and 27/28-H (δ H = 6.80 ppm).…”

“…They are structurally related to some other cyclic peptides, for example, schizotrin A, isolated from the cyanobacterium Schizotrix sp. [3] and pahayokolide A from Lyngbya sp. [4] Tychonamide A and B contain the novel β-amino acid 3-amino-2,5,7-trihydroxy-8-phenyloctanoic acid (Atpoa).…”

“…(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) compounds are thus further members of the β-amino acid containing peptides, such as microcystins, [5] nodularins, [6] nostophycin, [7] scytonemin A, [8] calophycin, [9] cryptophycin, [10] puwainaphycins, [11] schizotrin A, [3] and pahayokolide A and B. [4] Tychonamide A and B exhibit cytotoxic activity towards several cancer cell lines (mean IC 50 value of 0.9 and 3.3 µg mL -1 , respectively).…”

Synechocystis MCCB 114 and 115 as putative probionts for Penaeus monodon post-larvae

“…Cyanobacteria (blue-green algae ) have not yet been suggested as candidate probiotics in aquaculture. However, marine cyanobacteria in particular have been in focus for quite some time as a potential source of antagonistic compounds (Pergament & Carmeli 1994, Mundt et al 2001. The secretion of antimicrobial substances is an important part of the competition process in the natural environment, having a beneficial effect on the host by modifying the host-associated ambient microbial community (Verschuere et al 2000).…”

Absolute Configuration and Biosynthesis of Pahayokolide A from Lyngbya sp. Strain 15-2 of the Florida Everglades

“…Both pahayokolides A and B contain a cyclic undecapeptide and an unusual β-amino acid, 5,7,. Although β-amino acids are common in cyanobacterial peptides, only the pahayokolides, lyngbyazothrins A-D and schizotrin A contain Athmu Pergament et al, 1994).…”