Almiramide D, cytotoxic peptide from the marine cyanobacterium Oscillatoria nigroviridis

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

*Corresponding author for this work

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Marine benthic cyanobacteria are widely known as a source of toxic and potentially useful compounds. These microorganisms have been studied from many Caribbean locations, which recently include locations in the Colombian Caribbean Sea. In the present study, six lipopeptides named almiramides D to H, together with the known almiramide B are identified from a mat characterized as Oscillatoria nigroviridis collected at the Island of Providence (Colombia, S.W. Caribbean Sea). The most abundant compounds, almiramides B and D were characterized by NMR and HRESIMS, while the structures of the minor compounds almiramides E to H were proposed by the analysis of their HRESIMS and MS<sup>2</sup> spectra. Almiramides B and D were tested against six human cell lines including a gingival fibroblast cell line and five human tumor cell lines (A549, MDA-MB231, MCF-7, HeLa and PC3) showing a strong but not selective toxicity.

Original languageEnglish
Pages (from-to)6789-6795
Number of pages7
JournalBioorganic & Medicinal Chemistry
Volume22
Issue number24
Early online date4 Nov 2014
DOIs
Publication statusPublished - 15 Dec 2014

Fingerprint

Oscillatoria
Cyanobacteria
Cells
Oceans and Seas
Peptides
Lipopeptides
Cell Line
Colombia
Poisons
Fibroblasts
Tumor Cell Line
Islands
Microorganisms
Toxicity
Tumors
Nuclear magnetic resonance
almiramide D
almiramide B

Keywords

  • Almiramides
  • Lipopeptides
  • Marine benthic cyanobacteria
  • Marine natural products
  • Oscillatoria nigroviridis
  • Toxicity against human cell

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Medicine(all)

Cite this

Quintana, J., Bayona, L. M., Castellanos, L., Puyana, M., Camargo, P., Aristizábal, F., ... Ramos, F. A. (2014). Almiramide D, cytotoxic peptide from the marine cyanobacterium Oscillatoria nigroviridis. Bioorganic & Medicinal Chemistry, 22(24), 6789-6795. https://doi.org/10.1016/j.bmc.2014.10.039

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.

In: Bioorganic & Medicinal Chemistry, Vol. 22, No. 24, 15.12.2014, p. 6789-6795.

Research output: Contribution to journalArticle

Quintana, J, Bayona, LM, Castellanos, L, Puyana, M, Camargo, P, Aristizábal, F, Edwards, C, Tabudravu, JN, Jaspars, M & Ramos, FA 2014, 'Almiramide D, cytotoxic peptide from the marine cyanobacterium Oscillatoria nigroviridis', Bioorganic & Medicinal Chemistry, vol. 22, no. 24, pp. 6789-6795. https://doi.org/10.1016/j.bmc.2014.10.039
Quintana J, Bayona LM, Castellanos L, Puyana M, Camargo P, Aristizábal F et al. Almiramide D, cytotoxic peptide from the marine cyanobacterium Oscillatoria nigroviridis. Bioorganic & Medicinal Chemistry. 2014 Dec 15;22(24):6789-6795. https://doi.org/10.1016/j.bmc.2014.10.039
Quintana, Jairo ; Bayona, Lina M. ; Castellanos, Leonardo ; Puyana, Mónica ; Camargo, Paola ; Aristizábal, Fabio ; Edwards, Christine ; Tabudravu, Jioji N. ; Jaspars, Marcel ; Ramos, Freddy A. / Almiramide D, cytotoxic peptide from the marine cyanobacterium Oscillatoria nigroviridis. In: Bioorganic & Medicinal Chemistry. 2014 ; Vol. 22, No. 24. pp. 6789-6795.
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abstract = "Marine benthic cyanobacteria are widely known as a source of toxic and potentially useful compounds. These microorganisms have been studied from many Caribbean locations, which recently include locations in the Colombian Caribbean Sea. In the present study, six lipopeptides named almiramides D to H, together with the known almiramide B are identified from a mat characterized as Oscillatoria nigroviridis collected at the Island of Providence (Colombia, S.W. Caribbean Sea). The most abundant compounds, almiramides B and D were characterized by NMR and HRESIMS, while the structures of the minor compounds almiramides E to H were proposed by the analysis of their HRESIMS and MS2 spectra. Almiramides B and D were tested against six human cell lines including a gingival fibroblast cell line and five human tumor cell lines (A549, MDA-MB231, MCF-7, HeLa and PC3) showing a strong but not selective toxicity.",
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AU - Quintana, Jairo

AU - Bayona, Lina M.

AU - Castellanos, Leonardo

AU - Puyana, Mónica

AU - Camargo, Paola

AU - Aristizábal, Fabio

AU - Edwards, Christine

AU - Tabudravu, Jioji N.

AU - Jaspars, Marcel

AU - Ramos, Freddy A.

N1 - Acknowledgments This research was supported by grants from COLCIENCIAS Proyecto1216-452-21241, Universidad Jorge Tadeo Lozano, Universidad Nacional de Colombia sede Bogotá (DIB and Facultad de Ciencias), Fundación para la Promoción de la Investigación y la Tecnología del Banco de la República and Fundación Mariano Ospina Pérez-ICETEX. We want to acknowledge Jerónimo Vásquez, Rafael Barragán and Enrique Pomare for field assistance. The Ministerio de Ambiente, Vivienda y Desarrollo Territorial granted permission for scientific research on biological diversity (permission No. 4 of 10/02/2010).

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N2 - Marine benthic cyanobacteria are widely known as a source of toxic and potentially useful compounds. These microorganisms have been studied from many Caribbean locations, which recently include locations in the Colombian Caribbean Sea. In the present study, six lipopeptides named almiramides D to H, together with the known almiramide B are identified from a mat characterized as Oscillatoria nigroviridis collected at the Island of Providence (Colombia, S.W. Caribbean Sea). The most abundant compounds, almiramides B and D were characterized by NMR and HRESIMS, while the structures of the minor compounds almiramides E to H were proposed by the analysis of their HRESIMS and MS2 spectra. Almiramides B and D were tested against six human cell lines including a gingival fibroblast cell line and five human tumor cell lines (A549, MDA-MB231, MCF-7, HeLa and PC3) showing a strong but not selective toxicity.

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