Almiramide D, cytotoxic peptide from the marine cyanobacterium Oscillatoria nigroviridis

Quintana, Jairo; Bayona, Lina M.; Castellanos, Leonardo; Puyana, Mónica; Camargo, Paola; Aristizábal, Fabio; Edwards, Christine; Tabudravu, Jioji N.; Jaspars, Marcel; Ramos, Freddy A.

doi:10.1016/j.bmc.2014.10.039

Cited by 25 publications

(11 citation statements)

References 34 publications

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“…395 Other new metabolites 643-655 were obtained from the genera Anabaena, Lyngbya, Moorea, Oscillatoria and Symploca. [396][397][398][399][400][401][402] The absolute congurations of coibacins A and B 403 have been determined as 656 and 657 respectively by total synthesis. 404 Syntheses of biselyngbyolide A 405 (Lyngbya (Moorea) sp.…”

Section: Cyanobacteriamentioning

confidence: 99%

Marine natural products

et al. 2016

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This review covers the literature published in 2014 for marine natural products (MNPs), with 1116 citations (753 for the period January to December 2014) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1378 in 456 papers for 2014), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Cyanobacteriamentioning

confidence: 99%

Marine natural products

et al. 2016

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“…While the configuration of C-37 could not be rigorously established by chemical means, analysis of molecular models in conjunction with NOE data suggested an S -configuration for this chiral center. The double bond configuration of 3-methoxy-2-en-7-octynoic acid ( k ) in dragonamide C and that of 2-methyloct-2-en-7-ynoic acid ( m ) in dragonamide E, were both assigned as E-geometry by NOE analysis [47,48]. …”

Section: Different Methods To Determine the Absolute Configurationmentioning

confidence: 99%

“…Biological evaluation of these three compounds showed that almiramides B and C possessed good selectivity between parasite and mammalian cells with strong in vitro antiparasitic activity against leishmania (IC 50 = 2.4 and 1.9 μM, respectively), and weak activity against Vero cells (IC 50 = 52.3 and 33.1 μM, respectively). Just recently, a series of new terminal Moya-containing linear peptides, almiramides D–H ( 55 – 59 ) along with known almiramide B (Figure 8), were isolated and identified from a cyanobacterium sample of Oscillatoria nigroviridis collected at the Colombian Caribbean Sea [48]. Intriguingly, two structurally representative almiramides B and D showed mild toxicity against five human tumor cell lines, but high toxicity against the gingival fibroblast cell line was used as reference to evaluate selectivity against tumor cell lines compared with primary cell line.…”

Section: Acyclic Lipopeptides Containing Terminal Alkyne From Marimentioning

confidence: 99%

Alkynyl-Containing Peptides of Marine Origin: A Review

et al. 2016

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Since the 1990s, a number of terminal alkynyl residue-containing cyclic/acyclic peptides have been identified from marine organisms, especially cyanobacteria and marine mollusks. This review has presented 66 peptides, which covers over 90% marine peptides with terminal alkynyl fatty acyl units. In fact, more than 90% of these peptides described in the literature are of cyanobacterial origin. Interestingly, all the linear peptides featured with terminal alkyne were solely discovered from marine cyanobacteria. The objective of this article is to provide an overview on the types, structural characterization of these unusual terminal alkynyl fatty acyl units, as well as the sources and biological functions of their composed peptides. Many of these peptides have a variety of biological activities, including antitumor, antibacterial, antimalarial, etc. Further, we have also discussed the evident biosynthetic origin responsible for formation of terminal alkynes of natural PKS (polyketide synthase)/NRPS (nonribosome peptide synthetase) hybrids.

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“…Compounds 10 and 12 exhibit mild toxicity against five human tumor cell lines (A549, MCF-7, HeLa, PC3 and MDA-MB231) and high toxicity against the gingival fibroblast cell line [21]. …”

Section: Linear Peptidesmentioning

confidence: 99%

New Peptides Isolated from Marine Cyanobacteria, an Overview over the Past Decade

Zhang

et al. 2017

Marine Drugs

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Marine cyanobacteria are significant sources of structurally diverse marine natural products with broad biological activities. In the past 10 years, excellent progress has been made in the discovery of marine cyanobacteria-derived peptides with diverse chemical structures. Most of these peptides exhibit strong pharmacological activities, such as neurotoxicity and cytotoxicity. In the present review, we summarized peptides isolated from marine cyanobacteria since 2007.

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Almiramide D, cytotoxic peptide from the marine cyanobacterium Oscillatoria nigroviridis

Cited by 25 publications

References 34 publications

Marine natural products

Marine natural products

Alkynyl-Containing Peptides of Marine Origin: A Review

New Peptides Isolated from Marine Cyanobacteria, an Overview over the Past Decade

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