Ernesto Fattorusso

Ernesto Fattorusso
University of Naples Federico II | UNINA · Department of Pharmacy

Professor Emeritus of Organic Chemistry

About

407
Publications
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Introduction
Academic activity: 2011 Professor Emeritus of Organic Chemistry at University of Naples Federico II; 1975-2010 full professor of Organic Chemistry at University of Naples Federico II; 1987/1990 and 1997/2000: Dean of the Faculty of Pharmacy. Research activity: 430 publications and 10 int. patents mainly focused upon Chemistry of bioactive metabolites from marine organisms Editorial Activity: Editor of Steroids; Editorial Board of Marine Drugs and Chinese Journal of Natural Medicines

Publications

Publications (407)
Article
Blooms of the toxic dinoflagellates Ostreopsis have become common along rocky shores of the Mediterranean Sea. In addition to health problems for beach-goers, Ostreopsis toxins may accumulate in benthic marine animals used for human consumption, which however at times have shown signals of stress and even mortality. In order to elucidate the actual...
Article
Full-text available
In the present work we performed a combined experimental and computational study on the interaction of the natural antimalarial endoperoxide plakortin and its synthetic analogue 4a with heme. Obtained results indicate that the studied compounds produce reactive carbon radical species after being reductively activated by heme. In particular, similar...
Article
Full-text available
The organic extract from Oceanapia bartschi has been shown to contain the antibiotic diterpene Ambliol A (1) and three indole derivatives, 3-bromoindole (2), 6-bromo-3-indolecarboxyaldehyde (3), and 6-bromo-5-hydroxy-3-indolecarboxyaldehyde (4). The structure of the novel compound 4 has been established from its spectroscopic (
Article
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Two linear dihydroxy diterpenes were isolated from the sponge Myrmekioderma styx. The structure of these com pounds were deduced by MS, UV, IR
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The red-pigmented caribbean sponge Thorecta horridus contains thorexanthin (3-methoxy-β-X-caroten-4-one) as a new carotenoid pigment. Its structure was determined by spectroscopic methods, including 2 D NMR experiments.
Article
Full-text available
A new sesquiterpene phenol, containing the rather uncommon chlorine atom, was isolated from a sample of Smenospongia aurea collected along Bahama’s Islands. Its structure has been elucidated by spectroscopic analysis and confirmed via synthesis. This com pound exhibited antibacterial activity.
Article
Full-text available
Since the late 1990's, a respiratory syndrome has been repetitively observed in humans concomitant with Ostreopsis spp. blooms (mainly O. cf. ovata) in the Mediterranean area. Previous studies have demonstrated that O. cf. ovata produces analogues of palytoxin (ovatoxins and a putative palytoxin), one of the most potent marine toxins. Based on the...
Article
For the optimization of the plakortin pharmacophore, we recently proposed a straightforward synthesis of 4-carbomethoxy-3-methoxy-1,2-dioxanes as potential antimalarial drug candidates. Herein we report the chemoselective reduction of the 4-carbomethoxy group which has allowed us to prepare in good yields twenty-four new endoperoxides carrying eith...
Article
Full-text available
The role of lipids in controlling water exchange is fundamentally a matter of molecular organization. In the present study we have observed that in snake molt the water permeability drastically varies among species living in different climates and habitats. The analysis of molts from four snake species: tiger snake, Notechis scutatus, gabon viper,...
Article
Full-text available
The harmful dinoflagellate Ostreopsis cf. ovata has been causing toxic events along the Mediterranean coasts and other temperate and tropical areas, with increasing frequency during the last decade. Despite many studies, important biological features of this species are still poorly known. An integrated study, using different microscopy and molecul...
Article
Blooms of Ostreopsis spp. once confined to tropical and subtropical areas have recently spread to more temperate regions such as the Mediterranean and the Southern-Atlantic coasts of Europe. However, while O. confronta (cf.) ovata has caused several toxic outbreaks, the presence of O. cf. siamensis has been reported rather occasionally and in very...
Article
Full-text available
Two new sulfoxide-containing metabolites, aplisulfamines A and B, have been isolated from an Aplidium sp. collected in the Bay of Naples. Their planar structure and geometry of a double bond were readily determined by using standard methods, mainly NMR spectroscopy. An original approach was used to assign the absolute configuration at the three con...
Article
Full-text available
The Northern Adriatic Sea is the area of the Mediterranean Sea where eutrophication and episodes related to harmful algae have occurred most frequently since the 1970s. In this area, which is highly exploited for mollusk farming, the first occurrence of human intoxication due to shellfish consumption occurred in 1989, nearly 10 years later than oth...
Article
Full-text available
Leucettamols, bifunctionalized sphingoid-like compounds obtained from a marine sponge Leucetta sp., act as non-electrophilic activators of the TRPA1 channel and potent inhibitors of the icilin-mediated activation of the TRPM8 channel, while they are inactive on CB(1), CB(2) and TRPV1 receptors. Leucettamols represent the first compounds of marine o...
Article
Full-text available
An exhaustive exploration into the metabolic content of the Mediterranean sponge Axinella-polypoides resulted in the isolation of the new betaine 5 and the new cyclonucleoside 8. The structures of the new metabolites were elucidated by spectroscopic methods assisted by computational methods. The analysis also provided evidence that the sponge does...
Article
Ovatoxin-a is the main toxin produced by Ostreopsis ovata, a benthic dinoflagellate that has bloomed massively across the Mediterranean basin over the past years, inflicting both human and environmental suffering. Ovatoxin-a has recently been isolated from cultures of O. ovata and structurally identified as an analogue of palytoxin: in comparison w...
Chapter
This book offers an integrated review of the most recent trends in natural products drug discovery and key lead candidates that are outstanding for their chemistry and biology as a starting point in novel drug development. The authors focus on different trends that are and will continue to be impacting multiples stages of modern drug discovery from...
Article
Chemical investigation of the marine sponge Plakortis cfr. lita afforded a library of endoperoxyketal polyketides, manadoperoxides B-K (3-5 and 7-13) and peroxyplakoric esters B(3) (6) and C (14). Eight of these metabolites are new compounds and some contain an unprecedented chlorine-bearing THF-type ring in the side chain. The library of endoperox...
Article
Chemical analysis of the Indonesian soft coral Sinularia sp. (order Alcyonacea, family Alcyoniidae) afforded two new alkaloids, named sinulasulfoxide (1) and sinulasulfone (2), characterized by an amide linkage between a phytanic acid moiety and an uncommon sulfur-containing unit. Their complete stereostructures were elucidated by interpretation of...
Article
Full-text available
Background: Palytoxin and, likely, its analogues produced by the dinoflagellate genus Ostreopsis, represent a class of non-proteinaceous compounds displaying high toxicity in animals. Owing to the wide distribution and the poisonous effects of these toxins in humans, their chemistry and mechanism of action have generated a growing scientific inter...
Article
Full-text available
Mass appearances of the toxic dinoflagellate genus Ostreopsis are known to cause dangerous respiratory symptoms in humans exposed to aerosols. The outbreaks can appear in shallow marine waters of temperate regions around the globe. We followed a massive bloom event on a public beach on the northern Adriatic coast near Rovinj, Croatia. We identified...
Article
Currently, the benthic dinoflagellate Ostreopsis cf. ovata represents a serious concern to human health in the whole Mediterranean basin due to the production of palytoxin congeners, a putative palytoxin and ovatoxins (ovatoxin-a, -b, -c, -d/-e), listed among the most potent marine toxins. High resolution liquid chromatography-mass spectrometry (HR...
Article
Full-text available
There may be biogeographic aspects of interactions between toxic phytoplankton and their zooplankton grazers. Grazers that naturally co-occur with a given species of toxic phytoplankton may have evolved mechanisms to counteract adverse effects of phytoplankton toxins. Conversely, grazers that have no coevolutionary experience with a toxic phytoplan...
Article
Ring strain causes planar chirality in tedarenes A and B, two cyclic diarylheptanoids isolated from the marine sponge Tedania ignis. In both molecules, the chiral plane is an olefinic system, which is very rare among natural products. In tedarene A (1), interconversion is too fast to allow isolation of the enantiomeric atropisomers but still slow e...
Chapter
Protozoa are the causative agents of human diseases which affect more than one billion people and cause more than one million deaths per year, with a particular incidence in developing countries. The major contribution to these dramatic numbers is given by malaria, followed by leishmaniasis and trypanosomiasis (African trypanosomiasis and Chagas’ d...
Article
Ostreopsis cf. ovata is an epiphytic/benthic dinoflagellate that produces palytoxin-like compounds (putative palytoxin, ovatoxin-a, -b, -c, d and -e). Here we report on effects of nitrogen (N) and phosphorous (P) limited conditions on cell growth, cell size, biovolume, and toxin production of an O. cf. ovata strain isolated from the Adriatic Sea (I...
Article
Full-text available
Palytoxin is a potent marine toxin and one of the most complex natural compounds ever described. A number of compounds identified as palytoxin congeners (e.g., ovatoxins, mascarenotoxins, ostreocins, etc.) have not been yet structurally elucidated due to lack of pure material in quantities sufficient to an NMR-based structural investigation. In thi...
Article
Since 2005, the benthic dinoflagellate Ostreopsis cf. ovata has bloomed across the Mediterranean basin, provoking serious toxic outbreaks. LC/MS studies have identified a number of palytoxin-like compounds, termed ovatoxins, along with trace amounts of putative palytoxin as the causative agents of the O. cf. ovata -related human sufferings. So far,...
Article
Chemical investigation of the Indonesian soft coral Sinularia sp. resulted in the isolation of three known (1, 2 and 7) and five new (3–6 and 8) sterols, characterized by either 24-methylcholestane or gorgostane skeletons. The stereostructures of the new compounds have been elucidated by application of HR-MS and 2D NMR techniques. The isolated ster...
Book
Introduction (Fattorusso and Taglialatela-Scafati) Section I: Natural Product Trends in Different Groups of Marine Life 1.1. Taxonomy and marine natural products research (J. Blunt) 1.2. Chemistry of microalgae and macroalgae (Gerwick) 1.3. Chemistry of marine bacteria and fungi (W. Fenical) 1.4. Chemistry of marine invertebrates (sponges) (P. Prok...
Article
Full-text available
The chemical investigation of an Indonesian specimen of Theonella swinhoei afforded four aurantosides, one of which, aurantoside J (5), is a new compound. The structure of this metabolite, exhibiting the unprecedented N-α-glycosidic linkage between the pentose and the tetramate units, has been determined through detailed spectroscopic analysis. The...
Article
Full-text available
About 300 alkaloid structures isolated from marine ascidians are discussed in term of their occurrence, structural type and reported pharmacological activity. Some major groups (e.g., the lamellarins and the ecteinascidins) are discussed in detail, highlighting their potential as therapeutic agents for the treatment of cancer or viral infections.
Article
In the last years Ostreopsis spp. blooms have been reported in several Italian coastal stretches, showing a clear trend towards their extension. In 2005, during summer, an O. ovata bloom occurring in the coastal area in front of Genoa was tentatively associated with some human effects. Symptoms like rhinorrea, cough, fever, conjunctivitis, bronchoc...
Article
A new series of simple endoperoxides, characterized by a 3-methoxy-1,2-dioxane scaffold, was designed on the basis of a previously developed pharmacophore. Through a simplified and versatile scheme of synthesis, which utilizes cheap and commercially available starting materials, it was possible to obtain several structurally and stereochemically di...
Article
One new (1) and three known (2-4) isonitrile diterpenes, isolated from the Caribbean sponge Pseudoaxinella flava, were assayed in human cancer cell lines in vitro using an MTT colorimetric assay and quantitative videomicroscopy. Compounds 1-4 displayed activity for human PC3 prostate apoptosis-sensitive cancer cell lines. Compounds 3 and 4 demonstr...
Article
In the Mediterranean Sea, blooms of Ostreopsis cf. ovata and Ostreopsis siamensis have become increasingly frequent in the last decade and O. cf. ovata was found to produce palytoxin-like compounds (putative palytoxin, ovatoxin-a, -b, -c, -d and -e), a class of highly potent toxins. The environmental conditions seem to play a key role in influencin...
Article
Chemical analysis of the Indonesian soft coral Sinularia sp. (order Alcyonacea, family Alcyoniidae) afforded two known and three new C-4 norcembranoids, named chloroscabrolides A (3) and B (4) and prescabrolide (5). Chloroscabrolide A is a pentacyclic norcembranoid including an unprecedented THF-type ring to connect C-13 and C-15; furthermore, it i...
Chapter
Cancer cells often become resistant to structurally unrelated chemotherapeutics by overexpressing within their plasma membranes adenosine-5'-triphosphate (ATP)-binding cassette (ABC) transporters behaving as drug-efflux pumps at the expense of ATP hydrolysis. Three main transporters have been successively identified to confer such a multidrug-resis...
Article
Intense blooms of the benthic dinoflagellate Ostreopsis cf. ovata have occurred in the northern Adriatic Sea since 2006. These blooms are associated with noxious effects on human health and with the mortality of benthic organisms because of the production of palytoxin-like compounds. The O. cf. ovata bloom and its relationships with nutrient concen...
Article
Full-text available
Blooms of Ostreopsis spp. have been recently reported along the Mediterranean coasts of Spain, France, Italy, and Greece posing serious risks to human health. Occurrence of Ostreopsis spp. may result in palytoxin contamination of seafood and, in order to prevent sanitary risks, the need exists to develop efficient extraction procedures to be couple...
Article
Full-text available
Chemical analysis of the Mediterranean ascidian Polyandrocarpa zorritensis (Van Name 1931) resulted in the isolation of a series of molecules including two monoindole alkaloids, 3-indolylglyoxylic acid (3) and its methyl ester (4), 4-hydroxy-3-methoxyphenylglyoxylic acid methyl ester (1) and a new alkaloid we named zorrimidazolone (2). The structur...
Article
Full-text available
Free radicals are implicated in the aetiology of some gastrointestinal disorders such as gastric ulcer, colorectal cancer and inflammatory bowel disease. In the present study we investigated the antioxidant and genoprotective activity of some rotenoids (i.e. boeravinones) isolated from the roots of Boerhaavia diffusa, a plant used in the Ayurvedic...
Article
Spirocurcasone (14), a diterpenoid possessing the unprecedented "spirorhamnofolane" skeleton, was isolated from the root barks of Jatropha curcas, a plant extensively cultivated throughout the world, along with 11 known and two other new diterpenoids. The stereostructure of spirocurcasone was established using HRESIMS, NMR, and quantum mechanical c...
Article
From the polar organic extract of the Indonesian sponge Dasychalina sp. we have isolated haplosamate A (1), a unique C(28) sterol containing a sulfate group at C-3 and a methyl phosphate at C-15, along with its new desulfo analogue 2, whose structure has been secured by detailed NMR investigation. Compounds 1 and 2, as well as their semi-synthetic...
Article
Six new nitrogenous sesquiterpenes (1–6), which form two new isocyanide-isothiocyanate-formamide series, have been isolated from the marine sponge Axinellacannabina. The structure elucidation of these compounds is based upon spectral data, including 2D-nmr, and chemical interconversions. The complete assignment of all proton and carbon resonances i...
Article
Full-text available
Mumijo is a widely used traditional medicine, especially in Russia, Altai Mountains, Mongolia, Iran Kasachstan and in Kirgistan. Mumijo preparations have been successfully used for the prevention and treatment of infectious diseases; they display immune-stimulating and antiallergic activity as well. In the present study, we investigate the chemical...
Article
In our search for new antimalarial agents inspired by natural products, we describe herein the synthesis, the evaluation of in vitro antiplasmodial activity, and the SAR studies for a series of endoperoxide antimalarials based on the plakortin scaffold. These simplified analogues are characterized by: (i) a 3,6-dihydro-1,2-dioxin ring or a 1,2-diox...
Article
Full-text available
Extracts from Jatropha curcas, a plant used in African traditional medicine for various diseases, were tested for cytotoxic activity. The root extracts strongly reduced cell growth of tumor cells in vitro, a result consistent with the knowledge of the application of these plant extracts in traditional medicine, especially to cure/ameliorate cancer....
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
A new antiproliferative C11 alkyl sulfate, (3Z)-4,8-dimethylnon-3-en-1- sodium (or potassium) sulfate (1a) has been isolated from the Mediterranean ascidian Microcosmus vulgaris. Its structure determination was performed by spectroscopic and chemical methods.
Article
Palytoxins are a class of extremely potent non-proteic marine biotoxins, whose main biological target is the Na+/K+-ATPase. Since its isolation in 1971 from samples of Hawaiian Palythoa spp., palytoxin has drawn scientists’ attention from across the world because of its high toxicity, intriguing chemical structural architecture, and involvement in...
Article
Malaria, a pathology caused by protozoa belonging to the genus Plasmodium, is one of the major threats to global health, with about 300–500 million new clinical cases occurring every year and 1–3 million annual deaths. The recrudescence in the number of fatal cases registered in recent years can be attributed to the diffusion of multi-drug resistan...
Article
Alexandrium ostenfeldii is a widespread toxic dinoflagellate that has recently bloomed across the Adriatic Sea, seriously threatening both shellfish consumers and aquacultures. In 2007 we reported on preliminary studies carried out on field samples and cultures of A. ostenfeldii. At the time, along with three major spirolides - among which 27-hydro...
Article
The state of the art of LC-MS of palytoxin and its analogues is reported in the present review. MS data for palytoxin, 42-hydroxy-palytoxin, ostreocin-D, mascarenotoxins, and ovatoxins, obtained using different ionization techniques, namely fast-atom bombardment (FAB), matrix assisted laser desorption ionization (MALDI), and electrospray ionization...
Poster
Full-text available
Around the turn of the century, blooms of O. ovata have become very popular among scientists and the general public. Besides pathological problems in beach-goers, signals of stress and/or mortality have been detected in benthic organisms during blooms, while toxins have been shown to accumulate in marine animals used for human consumption (Rhodes e...
Article
Since the end of the 1990s the occurrence of blooms of the benthic dinoflagellates Ostreopsis spp. is spreading in many tropical and temperate regions worldwide, sometimes causing benthonic biocenosis suffering and occasional human distress. Ostreopsis ovata has been found to produce palytoxin-like compounds, a class of highly potent toxins. As gen...
Article
Over the past decades, Italian coastlines have been plagued by recurring presence of the benthic dinoflagellate Ostreopsis ovata. Such an alga has caused severe sanitary emergencies and economic losses due to its production of palytoxin-like compounds. Previous studies have confirmed the presence of ovatoxin-a (OVTX-a) as the major toxin of the alg...
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
The polyketides dihydroplakortin (3), and the dodecanoic acid derivatives 4 and 5, were isolated from the Caribbean marine sponge Plakortis simplex, and their structures fully characterized by spectroscopic and chemical means. The absolute stereochemistries of the known plakortin (1) and of compounds 3–5 were determined by applying Mosher's and Kus...
Article
Since its isolation dated back to as far as 1971, palytoxin has all along drawn scientists’ attention from across the world because of its high toxicity and fascinating chemical architecture. Commitment of the international scientific community to the study of this extremely potent non-proteic toxin has led to discover quite a number of palytoxin a...
Article
Eight known and two new triterpenoid derivatives, neemfruitins A (9) and B (10), have been isolated from the fruits of neem, Azadirachta indica, a traditional antimalarial plant used by Asian and African populations. In vitro antiplasmodial tests evidenced a significant activity of the known gedunin and azadirone and the new neemfruitin A and provi...
Article
A bioassay guided approach was used to isolate two antiproliferative sulfated metabolites, the 3,7,11,15-tetramethyl-hexadecan-1,19-sodium disulfate (1a) and the heneicosane-1,21-sodium disulfate (2a) from the Mediterranean tunicate Ascidia mentula. Their structures were determined by an extensive spectroscopic analysis and chemical methods.
Article
Agelongine (1), a novel bromopyrrole alkaloid containing a pyridinium ring in place of the imidazole nucleus, usually found in Agelas alkaloids, has been isolated from the Caribbean sponge Agelas longissima, and its structure established by spectroscopic analysis and chemical degradation. Agelongine exhibited an antiserotonergic activity tested in...
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
Terpioside B (2a), a unique glycolipid containing two fucose residues in the furanose form in its pentasaccharide chain, was isolated from the marine sponge Terpios sp. Its complete stereostructure was solved by interpretation of mass spectrometric and NMR data along with CD and GG-MS analyses of its degradation products. Terpioside B is a potent i...
Article
Full-text available
In the present study, 13 bromopyrrole alkaloids, including the oroidin analogs hymenidin (2), dispacamide B (3) and dispacamide D (4), stevensine (5) and spongiacidin B (6), their derivatives lacking the imidazole ring bromoaldisin (7), longamide B (8) and longamide A (9), the dimeric oroidin derivatives sceptrin (10) and dibromopalau'amine (11), a...
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
The new endoperoxyketal polyketides manadoperoxides A-D (2-5) have been isolated from the Indonesian sponge Plakortis cfr. simplex and their stereostructures established by means of spectroscopic data and semisynthetic transformations. Manadoperoxides were assayed in vitro against D10 and W2 strains of Plasmodium falciparum and showed moderate anti...
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.