Brigida D'Abrosca

Potential allelochemicals from Sambucus nigra

Twenty-four aromatic metabolites belonging to cyanogenins, lignans, flavonoids, and phenolic glycosides were obtained from Sambucus nigra. Structures were determined on the basis of their spectroscopic features. Two compounds have been isolated and identified as (2S)-2-O-beta-D-glucopyranosyl-2-hydroxyphenylacetic acid and benzyl 2-O-beta-D-glucopyranosyl-2,6-dihydroxybenzoate. All the compounds have been assayed on dicotyledons Lactuca sativa (lettuce) and Raphanus sativus (radish) and monocotyledon Allium cepa (onion) to test their stimulatory or inhibitory effects on seed germination and radicle elongation. Cyanogenins have a mainly inhibiting effect while lignans stimulate the growth. Some compounds show different effects on dicotyledons and monocotyledons.

Chemical Constituents of the Aquatic Plant Schoenoplectus lacustris: Evaluation of Phytotoxic Effects on the Green Alga Selenastrum capricornutum

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 C13nor-isoprenoids were identified. The structure of the new compound, 1-benzoyl-glycerol-2-α-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 Selenastrumcapricornutum, 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.

Spectroscopic characterization and antiproliferative activity on HepG2 human hepatoblastoma cells of flavonoid C-glycosides from Petrorhagia velutina.

Eight flavonoid C-glycosides, including three new analogues, have been isolated from leaf and root methanolic extracts of Petrorhagia velutina, a Mediterranean herbaceous plant. The antiproliferative activity against human hepatoblastoma cancer cell line HepG2 has been analyzed by the MTT (3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide) test. Isoorientin (4) significantly reduces the proliferation of HepG2 cells as determined by the complete conversion of the tetrazolium probe into formazan after 48 h of exposure.

Phytotoxicity evaluation of five pharmaceutical pollutants detected in surface water on germination and growth of cultivated and spontaneous plants.

The phytotoxicity of 5 pharmaceuticals detected in Italian rivers, atorvastatin (7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-yl-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid), gemfibrozil (5-(2,5-dimethylphenoxy)-2,2-dimethyl-pentanoic acid), tamoxifene (2-[4-(1,2-diphenylbut-1-enyl)phenoxy]-N,N-dimethyl-ethanamine), ethinyl estradiol (17-ethynyl-13-methyl-7,8,9,11, 12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol) and sildenafil (methyl-9-propyl-2,4,7,8-tetrazabicyclo[4.3.0] nona-3,8,10-trien-5-one), has been assessed in a laboratory model. The treatment system consists of three main successive sections. The first one includes the phytotoxic evaluation of the single compounds on crops, Lactuca sativa (lettuce), Dacus carota subsp. sativa (carrot), and Lycopersicon esculentum (tomato), until the 10−9 M, concentration lower then the environmental amounts. The second section includes the phytotoxicity assessment of all the selected chemicals on wild species, Avena fatua (wild oats), Amaranthus retroflexus (redroot pigweed), Lolium perenne (perennial ryegrass), Taraxacum officinale (common dandelion), and Chenopodium album (lambsquarter), at the same concentration as previously used. The third section of the procedure includes the evaluation of the effects of the five pharmaceuticals, at 1 μM and 1 nM environmental concentrations, on the metabolism of L. sativa. The variation of the composition of the photosynthetic pigments, sugars, lipids, phenols, fatty acids and flavonoids in lettuce seedlings exposed to the pollutants in respect to the blank was evaluated. The results of the phytotoxicity assays showed the possibility of a notable impact on the different vegetal communities and evidenced different sensitivity among cultivated and wild species, probably due to the different plant physiology.

Potential allelopathic interference of Melilotus neapolitana metabolites on three coexisting species of Mediterranean herbaceous plant community

Abstract This study is focused on the allelopathic interference of Melilotus neapolitana, an annual stenomediterranean species frequently occurring in the herbaceous plant community of the Mediterranean macchia, on three coexisting species of the Mediterranean herbaceous plant community. The ethereal and methanol extracts of the plant led to the isolation of 11 allelochemicals: coumarin, cis- and trans-melilotoside, the dihydromelilotoside, seven flavone glycosides, as well as the inactive β-sitosterol, a C13-norterpene glucoside and a polyphenol. All the structures have been elucidated on the basis of their spectroscopic features. The organic extracts and all the pure compounds have been assayed for their allelopathic activity on three coexisting species, Petrorhagia velutina, Dactylis hispanica, and Phleum subulatum. The cluster analysis has shown a clear structure-activity relationship, by evidencing four main groups of compounds with a specific effect patterns. Coumarin, the most abundant compound both in the plant extracts and soil, is found to be highly phytotoxic on all the tested species. As for the flavone glycosides, it is shown that aglycones play an important role due to their bioactivity.

Chemical Composition and Seasonality of Aromatic Mediterranean Plant Species by NMR-Based Metabolomics.

An NMR-based metabolomic approach has been applied to analyse seven aromatic Mediterranean plant species used in traditional cuisine. Based on the ethnobotanical use of these plants, the approach has been employed in order to study the metabolic changes during different seasons. Primary and secondary metabolites have been detected and quantified. Flavonoids (apigenin, quercetin, and kaempferol derivatives) and phenylpropanoid derivatives (e.g., chlorogenic and rosmarinic acid) are the main identified polyphenols. The richness in these metabolites could explain the biological properties ascribed to these plant species.

Kaempferol glycosides from Lobularia maritima and their potential role in plant interactions.

Six kaempferol glycosides, four of them characterized for the first time, were isolated from the leaf extract of Lobularia maritima. The structural elucidation was performed by a combined approach using Electrospray-Ionization Triple-Quadrupole Mass-Spectrometric (ESI/TQ/MS) techniques, and 1D- and 2D-NMR experiments (1H, 13C, DEPT, DQ-COSY, TOCSY, ROESY, NOESY, HSQC, HMBC, and HSQC-TOCSY). The isolated kaempferol derivatives have different disaccharide substituents at C(3) and four of them have a rhamnose unit at C(7). To evaluate their potential allelopathic role within the herbaceous plant community, the compounds, as well as the aglycone obtained from enzymatic hydrolysis, have been tested in vitro on three coexisting plant species, Dactylis hispanica, Petrorhagia velutina, and Phleum subulatum. The results obtained allow us to hypothesize that the type of the sugar modulates the biological response. The bioassay data, analyzed by a multivariate approach, and grouping the compounds on the basis of the number of sugar units and the nature of carbohydrates present in the disaccharide moiety, indicate a structure-activity relationship.

Chemical constituents and in vitro anti-inflammatory activity of Cistanche violacea Desf. (Orobanchaceae) extract

A new iridoid (1) and a new phenylethanoid glycoside (4), together with five known compounds (2, 3, 5, 6 and 7), were isolated for the first time from the ethyl acetate soluble part of the hydroalcoholic extract of the aerial parts of Cistanche violacea Desf. (Orobanchaceae), an endemic species of the North of the Sahara. The structures of these compounds have been elucidated on the basis of extensive 2D NMR spectroscopic analysis, including COSY, TOCSY, NOESY, HSQC, CIGAR-HMBC, H2BC and HSQC-TOCSY. All compounds were isolated from C. violacea for the first time. The anti-inflammatory activity of the EtOAc extract of C. violacea, was investigated by using human red blood cell (HRBC) membrane stabilization and inhibition of the albumin denaturation method. This study demonstrates, for the first time the effectiveness of C. violacea in combating inflammation, this might be believed to be influenced by the synergistic action of the above isolated compounds. The present study suggests that C. violacea would serve as a source for the discovery of novel anti-inflammatory agents.

Structure determination of chamaedryosides A-C, three novel nor-neo-clerodane glucosides from Teucrium chamaedrys, by NMR spectroscopy.

Three new nor‐neo‐clerodane diterpenes, named chamaedryoside A (1), B (2) and C (3), have been isolated from the organic extracts of Teucrium chamaedrys (L.) and their structural characterization has been accomplished by 1H and 13C‐NMR spectra, and DEPT, by COSY, TOCSY, HSQC, HSQC‐TOSCY and HMBC experiments, as well as by ESI‐MS/MS techniques. The stereostructures have been elucidated by NOESY and computational calculations. Copyright

Synthesis and Biological Properties of Caffeic Acid-PNA Dimers Containing Guanine

Caffeic acid (CA; 3,4-dihydroxycinnamic acid) is endowed with high antioxidant activity. CA derivatives (such as amides) have gained a lot of attention due to their antioxidative, antitumor and antimicrobial properties as well as stable characteristics. Caffeoyl-peptide derivatives showed different antioxidant activity depending on the type and the sequence of amino acid used. For these reasons, we decided to combine CA with Peptide Nucleic Acid (PNA) to test whether the new PNA-CA amide derivatives would result in an improvement or gain of CA’s biological (i.e., antioxidant, cytotoxic, cytoprotective) properties. We performed the synthesis and characterization of seven dimer conjugates with various combinations of nucleic acid bases and focused NMR studies on the model compound ga-CA dimer. We demonstrate that PNA dimers containing guanine conjugated to CA exhibited different biological activities depending on composition and sequence of the nucleobases. The dimer ag-CA protected HepG2, SK-B-NE(2), and C6 cells from a cytotoxic dose of hydrogen peroxide (H2O2).