Biologically active cyclic polypeptides with fragments of β-amino acid derivatives isolated from marine organisms (review)

Abstract

Published data on the structure, stereochemistry, and biological activity of natural cyclic polypeptides containing fragments of β-amino acids are reviewed, and an attempt is made to relate the structure to the biological activity.According to available estimates [1], there are more β-amino acids in the nature than the 22 proteinogenic α-amino acids that take part in ribosomal protein synthesis. The β-amino acids exist either as such or as fragments of the molecules of natural compounds with various degrees of complexity [2] and most often as linear or cyclic peptides that are, in all probability, formed by such microorganisms as bacteria and fungi as a result of non-ribosomal protein synthesis [3].Before 1996 nothing was known about the structure of the simplest β-peptides in the crystal and in solution. Today there are numerous papers and reviews on natural, semisynthetic, and fully synthetic β-peptides, the most comprehensive of which are the papers [4][5][6]. For this reason we will not dwell on these aspects here.The aim of our review is to classify published data on the structure, stereochemistry, and biological activity and also to study the structure-activity relationship of cyclic β-peptides, which have shown greater resistance to the action of enzymes than their linear analogs and α-peptides and therefore exhibit biological selectivity.

Marine natural products

“…6 A number of reviews describing pharmacological development and potential for biomedical application of marine natural products have appeared. [7][8][9][10][11][12][13] Many classes of marine-sourced compounds have been reviewed to varying extents, including briarane-type diterpenoids, 14 cyclic polypeptides containing b-amino acid fragments, 15 pyrroloiminoquinone alkaloids, 16 antitumour peptides, 17 cyclic imines including spirolides and gymnodimines, 18 kahalalides, 19 guanidine-containing alkaloids, 20 ascidian-derived alkaloids, 21 2-aminoimidazole alkaloids, 22,23 other assorted alkaloids, 24 carotenoids, 25,26 algal bromophenols, 27 volatile algal halogenated compounds, 28 brominated compounds from Aplysina sponges, 29 furanocembranoids 30 and norcembranoids (from Sinularia sp. ), 31 a-conotoxins, 32 cladiellins, asbestinins and briarellins, 33 and eleutherobins, fuscosides and pseudopterosins.…”

Marine Peptide Secondary Metabolites

“…Highlights of bioactive modified peptides from marine sources have been reported in several reviews (Aneiros and Garateix, 2004;Romanova et al, 2011). Modified peptides from particular types of organism were detailed in reviews on marine sponges (Matsunaga and Fusetani, 2003;Andavan and LemmensGruber, 2010) or marine cyanobacteria from the genus Lyngbya (Liu and Rein, 2010).…”

Medusamide A, a Panamanian Cyanobacterial Depsipeptide with Multiple β-Amino Acids

“…To the best of our knowledge, multiple adjacent β-amino acids have not been previously observed in any cyanobacterial or other marine natural product. Moreover, only a very few marine natural products possess multiple β-amino acids (dihydrocyclotheonamide A, cyclocinamide A, theonellamides F, B, C, and onchidin), , and none have contiguous β-amino acids. This suggests involvement of a unique biosynthetic pathway to account for such an unusual structural motif as in medusamide A ( 1 ).…”