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

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

doi:10.3390/md17070385

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

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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.

Original language	English
Article number	385
Journal	Marine Drugs
Volume	17
Issue number	7
DOIs	https://doi.org/10.3390/md17070385
Publication status	Published - 27 Jun 2019

Bibliographical note

The research leading to these results has received funding from Marie Skłodowska-Curie Innovative Training Networks PhD (Project Marpipe MSCA-ITN-ETN Proposal number: 721421) and European Union 7th Framework Program PHARMASEA (312184)

Keywords

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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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

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

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.",

keywords = "marine microalgae, dinoflagellates, marine natural products (MNPs), bioactive compounds, blue biotechnology, amphidinol, antifungal, anticancer",

author = "Mart{\'i}nez, {Kevin A} and Chiara Lauritano and Dana Druka and Giovanna Romano and Teresa Grohmann and Marcel Jaspars and Jes{\'u}s Mart{\'i}n and Caridad D{\'i}az and Bastien Cautain and {de la Cruz}, Mercedes and Adrianna Ianora and Fernando Reyes",

note = "The research leading to these results has received funding from Marie Sk{\l}odowska-Curie Innovative Training Networks PhD (Project Marpipe MSCA-ITN-ETN Proposal number: 721421) and European Union 7th Framework Program PHARMASEA (312184)",

year = "2019",

month = jun,

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doi = "10.3390/md17070385",

language = "English",

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T1 - Amphidinol 22, a New Cytotoxic and Antifungal Amphidinol from the Dinoflagellate Amphidinium carterae

AU - Martínez, Kevin A

AU - Lauritano, Chiara

AU - Druka, Dana

AU - Romano, Giovanna

AU - Grohmann, Teresa

AU - Jaspars, Marcel

AU - Martín, Jesús

AU - Díaz, Caridad

AU - Cautain, Bastien

AU - de la Cruz, Mercedes

AU - Ianora, Adrianna

AU - Reyes, Fernando

N1 - The research leading to these results has received funding from Marie Skłodowska-Curie Innovative Training Networks PhD (Project Marpipe MSCA-ITN-ETN Proposal number: 721421) and European Union 7th Framework Program PHARMASEA (312184)

PY - 2019/6/27

Y1 - 2019/6/27

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.

AB - 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.

KW - marine microalgae

KW - dinoflagellates

KW - marine natural products (MNPs)

KW - bioactive compounds

KW - blue biotechnology

KW - amphidinol

KW - antifungal

KW - anticancer

UR - http://www.mendeley.com/research/amphidinol-22-new-cytotoxic-antifungal-amphidinol-dinoflagellate-amphidinium-carterae

U2 - 10.3390/md17070385

DO - 10.3390/md17070385

M3 - Article

C2 - 31252576

SN - 1660-3397

VL - 17

JO - Marine Drugs

JF - Marine Drugs

IS - 7

M1 - 385

ER -

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

Abstract

Bibliographical note

Keywords

UN SDGs

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