Amphidinol 22, a New Cytotoxic and Antifungal Amphidinol from the Dinoflagellate Amphidinium carterae

Kevin A Martínez, Chiara Lauritano (Corresponding Author), Dana Druka, Giovanna Romano, Teresa Grohmann, Marcel Jaspars, Jesús Martín, Caridad Díaz, Bastien Cautain, Mercedes de la Cruz, Adrianna Ianora, Fernando Reyes

Research output: Contribution to journalArticle

Abstract

Due to the unique biodiversity and the physical-chemical properties of their environment, marine microorganisms have evolved defense and signaling compounds that often have no equivalent in terrestrial habitats. The aim of this study was to screen extracts of the dinoflagellate Amphidinium carterae for possible bioactivities (i.e., anticancer, anti-inflammatory, anti-diabetes, antibacterial and antifungal properties) and identify bioactive compounds. Anticancer activity was evaluated on human lung adenocarcinoma (A549), human skin melanoma (A2058), human hepatocellular carcinoma (HepG2), human breast adenocarcinoma (MCF7) and human pancreas carcinoma (MiaPaca-2) cell lines. Antimicrobial activities were evaluated against Gram-positive bacteria (Staphylococcus aureus MRSA and MSSA), Gram-negative bacteria (i.e., Escherichia coli and Klebsiella pneumoniae), Mycobacterium tuberculosis and the fungus Aspergillus fumigatus. The results indicated moderate biological activities against all the cancer cells lines and microorganisms tested. Bioassay-guided fractionation assisted by HRMS analysis allowed the detection of one new and two known amphidinols that are potentially responsible for the antifungal and cytotoxic activities observed. Further isolation, purification and structural elucidation led to a new amphidinol, named amphidinol 22. The planar structure of the new compound was determined by analysis of its HRMS and 1D and 2D NMR spectra. Its biological activity was evaluated, and it displayed both anticancer and antifungal activities.

Original languageEnglish
Article number385
JournalMarine Drugs
Volume17
Issue number7
DOIs
Publication statusPublished - 27 Jun 2019

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Dinoflagellida
Cell Line
Aspergillus fumigatus
Biodiversity
Klebsiella pneumoniae
Gram-Positive Bacteria
Methicillin-Resistant Staphylococcus aureus
Gram-Negative Bacteria
Mycobacterium tuberculosis
Biological Assay
Ecosystem
Staphylococcus aureus
Pancreas
Hepatocellular Carcinoma
Melanoma
Adenocarcinoma
Breast
Fungi
Anti-Inflammatory Agents
Escherichia coli

Keywords

  • marine microalgae
  • dinoflagellates
  • marine natural products (MNPs)
  • bioactive compounds
  • blue biotechnology
  • amphidinol
  • antifungal
  • anticancer

Cite this

Martínez, K. A., Lauritano, C., Druka, D., Romano, G., Grohmann, T., Jaspars, M., ... Reyes, F. (2019). Amphidinol 22, a New Cytotoxic and Antifungal Amphidinol from the Dinoflagellate Amphidinium carterae. Marine Drugs, 17(7), [385]. https://doi.org/10.3390/md17070385

Amphidinol 22, a New Cytotoxic and Antifungal Amphidinol from the Dinoflagellate Amphidinium carterae. / Martínez, Kevin A; Lauritano, Chiara (Corresponding Author); Druka, Dana; Romano, Giovanna; Grohmann, Teresa; Jaspars, Marcel; Martín, Jesús; Díaz, Caridad; Cautain, Bastien; de la Cruz, Mercedes; Ianora, Adrianna; Reyes, Fernando.

In: Marine Drugs, Vol. 17, No. 7, 385, 27.06.2019.

Research output: Contribution to journalArticle

Martínez, KA, Lauritano, C, Druka, D, Romano, G, Grohmann, T, Jaspars, M, Martín, J, Díaz, C, Cautain, B, de la Cruz, M, Ianora, A & Reyes, F 2019, 'Amphidinol 22, a New Cytotoxic and Antifungal Amphidinol from the Dinoflagellate Amphidinium carterae', Marine Drugs, vol. 17, no. 7, 385. https://doi.org/10.3390/md17070385
Martínez, Kevin A ; Lauritano, Chiara ; Druka, Dana ; Romano, Giovanna ; Grohmann, Teresa ; Jaspars, Marcel ; Martín, Jesús ; Díaz, Caridad ; Cautain, Bastien ; de la Cruz, Mercedes ; Ianora, Adrianna ; Reyes, Fernando. / Amphidinol 22, a New Cytotoxic and Antifungal Amphidinol from the Dinoflagellate Amphidinium carterae. In: Marine Drugs. 2019 ; Vol. 17, No. 7.
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abstract = "Due to the unique biodiversity and the physical-chemical properties of their environment, marine microorganisms have evolved defense and signaling compounds that often have no equivalent in terrestrial habitats. The aim of this study was to screen extracts of the dinoflagellate Amphidinium carterae for possible bioactivities (i.e., anticancer, anti-inflammatory, anti-diabetes, antibacterial and antifungal properties) and identify bioactive compounds. Anticancer activity was evaluated on human lung adenocarcinoma (A549), human skin melanoma (A2058), human hepatocellular carcinoma (HepG2), human breast adenocarcinoma (MCF7) and human pancreas carcinoma (MiaPaca-2) cell lines. Antimicrobial activities were evaluated against Gram-positive bacteria (Staphylococcus aureus MRSA and MSSA), Gram-negative bacteria (i.e., Escherichia coli and Klebsiella pneumoniae), Mycobacterium tuberculosis and the fungus Aspergillus fumigatus. The results indicated moderate biological activities against all the cancer cells lines and microorganisms tested. Bioassay-guided fractionation assisted by HRMS analysis allowed the detection of one new and two known amphidinols that are potentially responsible for the antifungal and cytotoxic activities observed. Further isolation, purification and structural elucidation led to a new amphidinol, named amphidinol 22. The planar structure of the new compound was determined by analysis of its HRMS and 1D and 2D NMR spectra. Its biological activity was evaluated, and it displayed both anticancer and antifungal activities.",
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N2 - Due to the unique biodiversity and the physical-chemical properties of their environment, marine microorganisms have evolved defense and signaling compounds that often have no equivalent in terrestrial habitats. The aim of this study was to screen extracts of the dinoflagellate Amphidinium carterae for possible bioactivities (i.e., anticancer, anti-inflammatory, anti-diabetes, antibacterial and antifungal properties) and identify bioactive compounds. Anticancer activity was evaluated on human lung adenocarcinoma (A549), human skin melanoma (A2058), human hepatocellular carcinoma (HepG2), human breast adenocarcinoma (MCF7) and human pancreas carcinoma (MiaPaca-2) cell lines. Antimicrobial activities were evaluated against Gram-positive bacteria (Staphylococcus aureus MRSA and MSSA), Gram-negative bacteria (i.e., Escherichia coli and Klebsiella pneumoniae), Mycobacterium tuberculosis and the fungus Aspergillus fumigatus. The results indicated moderate biological activities against all the cancer cells lines and microorganisms tested. Bioassay-guided fractionation assisted by HRMS analysis allowed the detection of one new and two known amphidinols that are potentially responsible for the antifungal and cytotoxic activities observed. Further isolation, purification and structural elucidation led to a new amphidinol, named amphidinol 22. The planar structure of the new compound was determined by analysis of its HRMS and 1D and 2D NMR spectra. Its biological activity was evaluated, and it displayed both anticancer and antifungal activities.

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