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Biomedical subjects

Marina DellaGreca

Publications and source records attributed to Marina DellaGreca.

17 recordsLinked to original sources

Structure elucidation and phytotoxicity of ecdysteroids from Chenopodium album.

The leaves of Chenopodium album were infused in H2O/MeOH. The extract treated with cold acetone gave heavy precipitation, which was removed by centrifugation. Solid material was fractionated into acidic and neutral fractions. The acidic material was subjected to different silica-gel column chromatographies, and then it was purified by reversed-phase HPLC to afford four known ecdysteroids and the new 3beta,14alpha-dihydroxy-5beta-pregn-7-ene-2,6,20-trione that were characterized by extensive spectroscopic investigation, especially by 1D- and 2D-NMR. Their effects on germination and growth of Lactuca sativa L. have been studied. The results are reported as percentage differences of germination, root elongation and shoot elongation, from the control at concentrations ranging from 10(-4) to 10(-7) M.

Chenopodium album↗

Phototransformation of carboxin in water. Toxicity of the pesticide and its sulfoxide to aquatic organisms.

Sunlight exposure of aqueous suspensions of carboxin (1) causes its phototransformation to sulfoxide 2 and minor components. Similar effects are observed in the presence of humic acid or nitrate or at different pH values. Photoproducts 2-9 were isolated by chromatographic techniques and/or identified by spectroscopic means. Carboxin 1 and its main photoproduct sulfoxide 2 were tested to evaluate acute toxicity to primary consumers typical of the aquatic environment: the rotifer Brachionus calyciflorus and two crustaceans, Daphnia magna and Thamnocephalus platyurus. Chronic tests comprised a producer, the alga Pseudokirchneriella subcapitata, and a consumer, the crustacean Ceriodaphnia dubia.

Animals↗

Low molecular weight phenols from the bioactive aqueous fraction of Cestrum parqui.

The aqueous fraction of fresh leaves of Cestrum parqui and its organic fractions have been assayed for their phytotoxicity on Lactuca sativa, Lycopersicon esculentum, and Allium cepa. The tests showed that the bioactivity was retained in the organic fractions. Chromatographic processes led to isolation and characterization of the N-(p-carboxymethylphenyl)-p-hydroxybenzamide together with 17 low molecular weight phenols and 2 flavones. The phytotoxicity tests showed a good activity of these compounds on the target species. Comparison of some metabolites with commercial herbicides revealed a major activity of the natural compounds at lower concentrations.

Cestrum↗

Chenoalbicin, a novel cinnamic acid amide alkaloid from Chenopodium album.

The roots of Chenopodium album were infused in MeOH, and the extract was partitioned between AcOEt and H2O. AcOEt-Soluble material was subjected to different silica-gel column chromatographies and then purified by reverse-phase HPLC to afford a new cinnamic acid amide alkaloid as a racemic mixture. The new compound, named chenoalbicin (1), was characterized by extensive spectroscopic investigation, especially 1D and 2D NMR spectroscopy. Its effects on the germination and growth of Lactuca sativa L. has been studied. The results are reported as percentage differences of germination, root elongation, and shoot elongation from the control at concentrations ranging from 10(-4) to 10(-7) M.

Alkaloids↗

Toxicity of prednisolone, dexamethasone and their photochemical derivatives on aquatic organisms.

Light exposure of aqueous suspensions of prednisolone and dexamethasone causes their partial phototransformation. The photoproducts, isolated by chromatographic techniques, have been identified by spectroscopic means. Prednisolone, dexamethasone and their photoproducts have been tested to evaluate their acute and chronic toxic effects on some freshwater chain organisms. The rotifer Brachionus calyciflorus and the crustaceans Thamnocephalus platyurus and Daphnia magna were chosen to perform acute toxicity tests, while the alga Pseudokircheneriella subcapitata (formerly known as Selenastrum capricornutum) and the crustacean Ceriodaphnia dubia to perform chronic tests. The photochemical derivatives are more toxic than the parent compounds. Generally low acute toxicity was found. Chronic exposure to this class of pharmaceuticals caused inhibition of growth population on the freshwater crustacean C. dubia while the alga P. subcapitata seems to be less affected by the presence of these drugs.

Animals↗

A mild photochemical approach to the degradation of phenols from olive oil mill wastewater.

Photooxidation of cathecol (1) is carried out in aqueous solution at lambda > 300 nm using different sensitizers: rose bengal (RB), 9,10-dicyanoanthracene (DCA), 2,4,6-triphenylpyrylium tetrafluoroborate (Pyryl). The highest degradation is observed in the UV/RB-sensitized reaction (66% after 15 h of irradiation), mineralization and formation of dimers are the final events. This procedure has been extended to tyrosol (2), caffeic acid (3), vanillic acid (4), 4-hydroxycinnamic acid (5) and 4-hydroxybenzoic acid (6) as well as to a mixture of all phenols. A reduced toxicity of the UV/RB-irradiated solutions of cathecol and tyrosol towards alga Ankistrodesmus braunii is also verified.

Analysis of Variance↗

Structure elucidation and phytotoxicity of C13 nor-isoprenoids from Cestrum parqui.

Twelve C(13) nor-isoprenoids have been isolated from the leaves of Cestrum parqui (Solanaceae). The structure (2R,6R,9R)-2,9-dihydroxy-4-megastigmen-3-one has been assigned to the new compound. All the structures have been determined by spectroscopic means and chemical correlations. The compounds showed phytotoxic effect on the germination and growth of Lactuca sativa L.

Cestrum↗

Isolation and phytotoxicity of apocarotenoids from Chenopodium album.

Two new compounds (1, 2) and 16 apocarotenoids (3-18) were isolated from the weed Chenopodium album. The structures of new apocarotenoids were determined to be (3R,6R,7E,9E,11E)-3-hydroxy-13-apo-alpha-caroten-13-one (1) and (6S,7E,9E,11E)-3-oxo-13-apo-alpha-caroten-13-one (2) by spectroscopic, NMR, and MS analysis. Five of the known compounds (5, 6, 13, 15, and 17) were previously reported only as synthetic compounds. Effects of these compounds on germination and growth of Lactuca sativa (lettuce) were studied in the 10(-4)-10(-7) M concentration range.

Carotenoids↗

Bioactivity of phenanthrenes from Juncus acutus on Selenastrum capricornutum.

Twenty-five 9,10-dihydrophenanthrenes, four phenanthrenes, a dihydrodibenzoxepin, and a pyrene, isolated from the wetland plant Juncus acutus, were tested to detect their effects on the green alga Selenastrum capricornutum. Nine of the compounds were isolated and identified for the first time. Most of the compounds caused inhibition of algal growth. The 9,10-dihydrophenanthrenes 1, 5, 21, and 22 were the most active.

Chlorophyta↗

Lignans and neolignans from Brassica fruticulosa: effects on seed germination and plant growth.

Five lignans, five neolignans, two sesquilignans, and a dilignan were identified from a phytotoxic extract of Brassica fruticulosa L. Compounds 8, 9, 12, and 13 have been isolated for the first time. Structures were determined on the basis of their spectroscopic features. Their effects on the germination and growth of two dicotyledons, Lactuca sativa (lettuce) and Lycopersicon esculentum (tomato), and a monocotyledon, Allium cepa (onion), as standard target species have been studied.

Brassica↗

Cinnamic acid amides from Chenopodium album: effects on seeds germination and plant growth.

Seven cinnamic acid amides have been isolated from Chenopodium album. The structures have been attributed by means of their spectral data. One of them, N-trans-4-O-methylferuloyl 4'-O-methyldopamine, is described for the first time. Their effects on germination and growth of dicotyledons Lactuca sativa L. (lettuce) and Lycopersicon esculentum L. (tomato) and of monocotyledon Allium cepa L. (onion) as standard target species have been studied in the range concentration 10(-4)-10(-7) M.

Amides↗

Identification of phototransformation products of prednisone by sunlight: toxicity of the drug and its derivatives on aquatic organisms.

Solar simulator irradiation of an aqueous suspension of prednisone, a widely prescribed drug, produces seven photochemical derivatives. The compounds have been identified on the basis of their physical features. All the chemicals have been tested to evaluate their toxic effects on freshwater organisms from different trophic levels. The rotifer Brachionus calyciflorus and two crustaceans, the cladoceran Daphnia magna and the anostracan Thamnocephalus platyurus, were used to perform acute toxicity tests. Chronic toxicity tests have been performed on the alga Pseudokirchneriella subcapitata (formerly known as Selenastrum capricornutum) and the crustacean Ceriodaphnia dubia. The results showed low acute and chronic toxicity of prednisone. Some of the photoproducts had high toxic effects on C. dubia.

Animals↗

Solid-state photodimerization of steroid enones.

Androst-4-ene-3,17-dione (1) and 17alpha-methyltestosterone (2) are dimerized in the solid-state by UV radiation. These substances were selected by a search in the CSD among the steroid enones presenting in the crystalline state an intermolecular short contact between a hydrogen alpha to a carbonyl group and the oxygen of an enone system. Dimerization occurs by transfer of the hydrogen to the oxygen and connection between the two involved carbons. Androst-4-ene-3,17-dione (1) affords dimer 3 and trimer 4, both formed by connection of the C-16 of a molecule with the C-3 of a near one. Irradiation of 17alpha-methyltestosterone (2) gives the isomeric trienones 5 and 6. These compounds are reasonably formed by dehydration of unisolated intermediate products 7 and/or 8 obtained by coupling of two molecules through a linkage between the C-2 and the C-3' carbons. The formation mechanisms of the photoproducts are satisfactory explained on the basis of the molecular arrangement of the monomers in the crystal state. Modeling of the dimeric molecules was done using molecular mechanics calculations. A single-crystal X-ray of the dimer of androst-4-ene-3,17-dione confirms the structural interpretation of spectral data. The conformer found in the solid-state agrees well with the results of molecular mechanics calculations.

Androstenedione↗

Phenanthrenoids from the wetland Juncus acutus.

Nine 9,10-dihydrophenanthrenes, three phenanthrenes and a related pyrene have been isolated from the wetland plant Juncus acutus. The structures have been attributed by means of their spectral data and chemical correlation. 5-(1-Ethoxy-ethyl)-2-hydroxy-7-methoxy-1,8-dimethyl-9,10-dihydrophenanthrene and 5-(1-phytoxy-ethyl)-2-hydroxy-7-methoxy-1,8-dimethyl-9,10-dihydrophenanthrene, 2,7-dihydroxy-1-methyl-5-vinylphenanthrene, 2,7-dimethoxy-1,6-dimethyl-5-vinylphenanthrene and 2,7-dihydroxy-1,6-dimethylpyrene are described for the first time. Many of the compounds showed in vitro phytotoxicity against Selenastrum capricornutum, a microalga used in aquatic tests.

Chlorophyta↗

Low-molecular-weight components of olive oil mill waste-waters.

A new lignan 1-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-(3-acetyl-4-hydroxy-5-methoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane, the secoiridoid 2H-pyran-4-acetic acid,3-hydroxymethyl-2,3-dihydro-5-(methoxycarbonyl)-2-methyl-, methyl ester, the phenylglycoside 4-[beta-D-xylopyranosyl-(1-->6)]-beta-D-glucopyranosyl-1,4-dihydroxy-2-methoxybenzene and the lactone 3-[1-(hydroxymethyl)-1-propenyl] delta-glutarolactone were isolated and identified on the basis of spectroscopic data including two-dimensional NMR, as components of olive oil mill waste-waters. The known aromatic compounds catechol, 4-hydroxybenzoic acid, protocatechuic acid, vanillic acid, 4-hydroxy-3,5-dimethoxybenzoic acid, 4-hydroxyphenylacetic acid, 3,4-dihydroxyphenylacetic acid, tyrosol, hydroxytyrosol, 2-(4-hydroxy-3-methoxy)phenylethanol, 2-(3,4-dihydroxy)phenyl-1,2-ethandiol, p-coumaric acid, caffeic acid, ferulic acid, sinapic acid, 1-O-[2-(3,4-dihydroxy)phenylethyl]-(3,4-dihydroxy)phenyl-1,2-ethandiol, 1-O-[2-(4-hydroxy)phenylethyl]-(3,4-dihydroxy)phenyl-1,2-ethandiol, D(+)-erythro-1-(4-hydroxy-3-methoxy)-phenyl-1,2,3-propantriol, p-hydroxyphenethyl-beta-D-glucopyranoside,2(3,4-dihydroxyphenyl)ethanol 3beta-D-glucopyranoside, and 2(3,4-dihydroxyphenyl)ethanol 4beta-D-glucopyranoside were also confirmed as constituents of the waste-waters.

Carbohydrate Sequence↗

Phenols and lignans from Chenopodium album.

Cinnamic acid, 4-hydroxy-cinnamic acid, ferulic acid, methyl ferulate, sinapic acid, methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate, 4-(1-hydroxyethyl)-2-methoxyphenol, vanillyl alcohol, 4-(hydroxymethyl)-2-methoxyphenol, 4-hydroxy-3-methoxybenzoic acid, 4-vinylphenol, 4-methylbenzaldehyde, N-[2-(1H-indol-3-yl)ethyl]acetamide, pinoresinol, syringaresinol, lariciresinol, 5,5'-dimethoxy-lariciresinol, threo-guaiacylglycerol-3-beta-4-syringaresinol ether and two new sesquilignans, namely, threo-guaiacylglycerol-alpha-O-methyl-beta-O-4-syringaresinol ether and threo-syringylglycerol-alpha-O-methyl-beta-O-4-syringaresinol ether, were isolated and identified as components of Chenopodium album. Constitutions were established on the basis of spectroscopic data, including two-dimensional NMR analyses.

Chenopodium album↗