Biomedical subjects
Publications and source records attributed to E Fattorusso.
The diarrhetic shellfish toxin composition in the hepatopancreas of mussels from the northern Adriatic sea was investigated. The major toxins were shown to be yessotoxin (YTX), homoyessotoxin (homoYTX) and 45-hydroxyyessotoxin (45-OHYTX), identified by comparison of their chromatographic and spectral properties with those reported in the literature.
A detailed analysis of the secondary metabolites of the sponge Aplysina cauliformis has been performed. Eight compounds were identified, two of which (13 and 14) are new bromotyrosine derivatives whose structures were determinated from spectroscopic evidence, including 2D NMR. The new compounds were analyzed for cytotoxic activity, and compound 14 was shown to inhibit mammalian protein synthesis and cell proliferation.
Three new 9,11-secosterols, 3 beta,6 alpha,11-trihydroxy-9,11-seco-5 alpha-cholest-7-ene-9-one (1), 24S- (2a), and 24R-methyl-3 beta,6 alpha, 11-trihydroxy-9,11-seco-5 alpha-cholest-7,22E-diene-9-one (2b), were isolated from the Indian Ocean gorgonia, Subergorgia suberosa. Their structures were established by spectroscopic data.
Two new sesterterpenes, lintenolides F (6 a, b) and G (7 a, b), were isolated from the Caribbean sponge Cacospongia cf. linteiformis. Their stereostructures were determined using spectroscopic and chemical methods. The new compounds (6 a, b and 7 a, b) and the related compounds lintenolides A-E (1 a, b-5 a, b), previously isolated from the sponge, exhibited antiproliferative activity on four cell lines.
Further investigation of the Caribbean marine sponge Agelas dispar for biologically active constituents has led to the isolation of the novel bromopyrrole alkaloids longamide B (1), and clathramides C (2) and D (3), whose structures have been determined by spectroscopic methods. Isolation of the known keramadine (4) and of the ecdysonic sterols ecdysterone (5) and ajugasterone C (6) is also reported. The antimicrobial activities of the isolated bromopyrrole alkaloids is summarized.
Three novel betaine alkaloids, called aminozooanemonin (1), pyridinebetaine A (2), and pyridinebetaine B (3), have been isolated from the Caribbean sponge Agelas dispar. Their structures were determined by FABMS, IR, UV, and 1D and 2D NMR spectroscopic experiments. Aminozooanemonin and pyridinebetaine A showed moderate antibacterial activity.
An investigation of the extracts from Allium neapolitanum has led to the isolation of 13 flavonoid glycosides, based on kaempferol, quercetin and isorhamnetin. Four of them are new compounds and have been identified as: kaempferol 3-O-[[2-O-alpha-L-rhamnopyranosyl-4-O-beta-D-glucopyranosyl]-beta-D- glucopyranoside]], isorhamnetin 3-O-[[2-O-alpha-L-rhamnopyranosyl-6-O-beta- D-glucopyranosyl]-beta-D-glucopyranoside], isorhamnetin 3-O-[[2-O-alpha-L-rhamnopyranosyl-6-O-beta-D-glycopyranosyl] beta-D-glucopyranoside]-7-O-beta-D-glucopyranoside and isorhamnetin 3-O-[[2-O-alpha-L-rhamnopyranosyl-6-O-beta-D-gentiobiosyl]- beta-D-glucopyranoside]]. The isolated compounds were evaluated for their anti-aggregation human platelet activity.
This study investigated the composition of diarrhoetic shellfish toxins in the hepatopancreas of mussels from the northern Adriatic Sea. The major toxins were shown to be yessotoxin, identified by its chromatographic properties and spectral data, and okadaic acid, detected both by fluorometric high-performance liquid chromatography and by comparison of its spectral properties with those of an authentic sample.
Four new sapogenins, porrigenins A (2a) and B (3a), identified as (25R)-5 alpha-spirostan-2 beta,3 beta,6 beta-triol and (25R)-2-oxo-5 alpha-spirostan-3 beta,6 beta-diol, respectively, and neoporrigenins A (2b) and B (3b) were also isolated from Allium porrum. In addition, the known agigenin (1a) and its 25S epimer, neoagigenin (1b), were also identified. Their structure elucidation was provided by comprehensive spectroscopic analyses. Compounds 1a, 2a, and 3a exhibited cytotoxicity and high antiproliferative activity on four different tumor cell lines in vitro.
From wild garlic Allium ursinum three new flavonoid glycosides were identified as kaempferol 3-O-beta-neohesperidoside-7-O-[2-O-(trans-p-coumaroyl)]-beta -D- glucopyranoside, kaempferol 3-O-beta-neohesperidoside-7-O-[2-O-(trans-feruloyl)]-beta-D- glucopyranoside, kaempferol 3-O-beta-neohesperidoside-7-O-[2-O-(trans-p-coumaroyl)-3-O-b eta-D- glucopyranosyl]-beta-D-glucopyranoside and characterized as the peracetates. Additionally, two known flavonoid glycosides kaempferol 3-O-beta-glucopyranoside and kaempferol 3-O-beta-neohesperidoside were isolated. The isolated compounds showed an inhibition of human platelet aggregation.
The sterol composition of the sponge Dysidea fragilis, coming from the lagoon of Venice, has been investigated; our results confirmed the variability of D. fragilis biochemistry. The sponge elaborates, in addition to eight usual 3 beta-hydroxy sterols, thirteen polyhydroxysterols, eight of them (6-13) were novel compounds. Their structures were established by spectroscopic data. New compounds 3 beta,5 alpha,6 beta,7 alpha-tetrahydroxy-cholest-8(9)-en-11-one (8), 3 beta,5 alpha,6 alpha-trihydroxy-9,11-secocholest-7-en-9-one (9) and 3 beta,5 alpha,6 alpha,9 alpha-tetrahydroxy-cholest-7-ene-6-sulfate (11) were proved to be cytotoxic on two different tumor cell lines in vitro.
The sterol composition of the Caribbean sponge Neofibularia nolitangere has been investigated. In addition to usual sterols this sponge elaborates comparable amounts of 24-methylene-4 alpha-methyl-5 alpha-cholest-8-en-3 beta-ol (1), which is very unusual among sponge sterols, and lesser quantities of two new polyoxygenated sterols, (24S)-24-ethyl-5 alpha-cholest-8-ene-5,6 beta,7 alpha-triol (2) and (24S)-24-ethyl-5 alpha-cholest-8(14)-ene-5,6 beta,7 alpha-triol (3).
A new polymeric pyridinium alkaloid named amphitoxin [2] has been isolated from Amphimedon compressa, and its structure determined by spectroscopic analysis. In laboratory feeding experiments, crude extracts and purified amphitoxin [2] from A. compressa at lower than natural concentration levels effectively deterred feeding of a generalist predatory Caribbean reef fish, Thalassoma bifasciatum.
The Senegalese sponge Microscleroderma spirophora has been found to produce exclusively very unusual 3 beta-methoxysteroids in place of the common 3 beta-hydroxysteroids. Six different methoxysteroids (three of which are novel compounds) have been isolated and identified by spectroscopic means (MS, IR, 1H and 13C NMR), and their taxonomic significance discussed. A new method for the determination of the configuration at C-24 in saturated 24-ethyl side chains is also proposed.
Three novel sterols with a rare D-ring unsaturation were isolated from the marine sponge Topsentia aurantiaca and identified as 5 alpha-cholest-14-ene-3 beta,16 alpha-diol (2), 24R-ethyl-5 alpha-cholest-14-ene-3 beta,16 alpha-diol (3), and 24S-ethyl-5 alpha-cholest-14-ene-3 beta,16 alpha-diol (4). The sponge also elaborates a further D-ring unsaturated sterol, 5 alpha-cholest-15-en-3 beta-ol (1), which has been previously described only as a synthetic product. All the 1H and 13C nuclear magnetic resonances of compounds 1 and 2 were assigned to the relevant protons and carbons by bidimensional COSY, HETCOR, and HMQC nuclear magnetic resonance experiments.
From the fruit body of the fungus Marasmius oreades (family Tricholomataceae), 4,4-dimethyl-5 alpha-ergosta-8,24(28)-dien-3 beta-ol (1), probably a biogenetic precursor of ergosterol, has been isolated along with ergosterol. Its stereostructure has been established unequivocally by spectroscopic methods, including 13C nuclear magnetic resonance.
Four new polyoxygenated sterols 2-5 were isolated from the marine black coral Antipathes subpinnata. The structures of these compounds, including stereochemical details, were deduced by ms, 1H- and 13C-nmr, 1H-1H COSY, and nOe difference spectroscopy. Compounds 2-5 are lethal to brine shrimp (Artemia salina).