Journal Article

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

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

2019

Overview

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.

• Publisher: MDPI AG,MDPI
• Subject: Adenocarcinoma / Algae / Amphidinium / Amphidinium carterae / amphidinol / Antibiotics / anticancer / Anticancer properties / antifungal / Antifungal activity / Antifungal agents / Antifungal Agents - chemistry / Antifungal Agents - isolation & purification / Antifungal Agents - pharmacology / antifungal properties / antineoplastic activity / Antineoplastic Agents - chemistry / Antineoplastic Agents - isolation & purification / Antineoplastic Agents - pharmacology / Antitumor activity / Aspergillus fumigatus / Aspergillus fumigatus - drug effects / Bacteria / Bio-assays / Bioactive compounds / Bioassays / Biodiversity / Biological activity / Biological effects / blue biotechnology / Breast / breast neoplasms / breasts / Cancer / Cell Line, Tumor / Cell lines / Chemical properties / Chemicophysical properties / Coliforms / Cytotoxicity / Diabetes mellitus / Dinoflagellates / Dinoflagellida - chemistry / Disease resistance / Drug resistance / Drug Screening Assays, Antitumor / E coli / Embryos / Escherichia coli / Fractionation / Fungi / Fungicides / Gram-negative bacteria / Gram-positive bacteria / habitats / Hepatocellular carcinoma / hepatoma / Humans / Inflammation / Klebsiella / Klebsiella pneumoniae / Liver cancer / Lung cancer / lungs / Magnetic Resonance Spectroscopy / marine microalgae / Marine microorganisms / marine natural products (MNPs) / mass spectrometry / Melanoma / Metabolism / Metabolites / methicillin-resistant Staphylococcus aureus / Microbial Sensitivity Tests / Microorganisms / Molecular Structure / Mycobacterium tuberculosis / neoplasm cells / Neoplasms / NMR / Nuclear magnetic resonance / nuclear magnetic resonance spectroscopy / Pancreas / Pancreatic cancer / Pancreatic carcinoma / physicochemical properties / Planar structures / Polyketides - chemistry / Polyketides - isolation & purification / Polyketides - pharmacology / skin (animal) / Skin cancer / Solvents / Staphylococcus infections / Structure-Activity Relationship / Tuberculosis / Tumor cell lines / Water purification