Synthesis of dimeric phenylethanoids isolated from olive oil mill wastewaters.
Two dimeric phenylethanoids isolated from olive oil mill wastewaters have been synthesized from cathecol, tyrosol and 3,4-dihydroxyphenylacetic acid.
Biomedical subjects
Publications and source records attributed to Marina Dellagreca.
Two dimeric phenylethanoids isolated from olive oil mill wastewaters have been synthesized from cathecol, tyrosol and 3,4-dihydroxyphenylacetic acid.
Forty-nine secondary metabolites were isolated from aqueous and alcoholic extracts of the aquatic plant Shoenoplectus lacustris. All compounds were characterized based on spectroscopic data. Eleven free and glycosylated low-molecular polyphenols, 17 cinnamic acid and dihydrocinnamic acid derivatives, 11 flavonoids, and 10 C13 nor-isoprenoids were identified. The structure of the new compound, 1-benzoyl-glycerol-2-alpha-L-arabinopyranoside, was elucidated by 2D NMR experiments (COSY, HSQC, HMBC, NOESY). To evaluate potential phytotoxic effects, all compounds were tested on the green alga Selenastrum capricornutum, a unicellular organism commonly used in tests of toxicity as a bioindicator of eutrophic sites. The most active compound was (-)-catechin, showing an inhibition similar to that of the algaecide CuSO4.
A sesquiterpene and a tetrahydroxylated acyclic diterpene as well as two known monoterpenes, 6 C(13)nor-terpenes and 11 aromatic compounds were isolated from the water extract of Malva silvestris. The structures of the compounds were determined by spectroscopic NMR and MS analysis. Effects of these compounds on germination and growth of dicotyledon Lactuca sativa L. (lettuce) were studied in the 10(-4)-10(-7)M concentration range.
Isolation, chemical characterization and phytotoxicity of nine polyhydroxylated terpenes (five C13nor-isoprenoids, two sesquiterpenes, a spirostane and a pseudosapogenin) from Cestrum parqui L'Herr are reported. In this work we completed the phytochemical investigation of the terpenic fraction of the plant and described the structural elucidation of polar isoprenoids using NMR methods. All the configurations of the compounds have been assigned by NOESY experiments. Four new structures have been identified as (3S,5R,6R,7E,9R)-5,6,9-trihydroxy-3-isopropyloxy-7-megastigmene, 5alpha-spirostan-3beta,12beta,15alpha-triol, and 26-O-(3'-isopentanoyl)-beta-d-glucopyranosyl-5alpha-furost-20(22)-ene-3beta,26-diol, and as an unusual tricyclic sesquiterpene. The compounds have been assayed for their phytotoxicity on lettuce at the concentrations ranging between 10(-4) and 10(-7)M. The activities of some compounds were similar to that of the herbicide pendimethalin.
The isolation and the structure determination of an unusual xyloside from the plant Chenopodium album is reported. The structure has been attributed by means of its spectral data.
Five C13 norisoprenoids, one of them glucosilated, have been isolated from the leaves of Brassica fruticulosa (Brassicaceae). The structure (3S,4R,7E,9S)-3,4,9-trihydroxy-5,7-megastigmadiene, has been assigned to the new compound. All the structures have been determined by spectroscopic means and chemical correlations.
Two new dimeric phenanthrenoids have been isolated by the methanol extract of rhizomes of Juncus acutus. The structures have been determined on the basis of their spectroscopic properties and by chemical correlation. The compounds showed in vitro phytotoxicity against Selenastrum capricornutum, a microalga used in aquatic tests.
Two natural cyanohydrins, isolated from Sambucus nigra, have been synthesised from mandelonitrile and penta-O-acetyl-beta-galactopyranose. The synthesis confirmed the stereochemistry of the compounds, which had been assigned on biogenetic grounds.
Twenty ent-labdane diterpenes, isolated from the aquatic plants Ruppia maritima and Potamogeton natans, were tested to detect their effects on aquatic organisms from different trophic levels. Toxicity tests were performed on aquatic producers (the alga Selenastrum capricornutum), and consumers including a rotifer (Brachionus calyciflorus), a cladoceran crustacean (Daphnia magna), and two anostracan crustaceans (Thamnocephalusplatyurus and Artemia salina). Furano-ent-labdanes exhibited high toxicity toward all of these organisms. 15,16-Epoxy-12(S)-hydroxy-8(17),13(16),14-ent-labdatrien-20.19-olide had a high toxicity only toward the algae and the rotifers. It was inactive for the crustaceans.