Contribution to a Taxonomic Revision of the Sicilian Helichrysum Taxa by PCA Analysis of Their Essential-Oil Compositions.

The chemical profile of the essential oils in ten populations of the genus Helichrysum Mill. (Asteraceae), collected in the loci classici of the nomenclatural types of the taxa endemic to Sicily, were analyzed. Our results confirm that the analysis of secondary metabolites can be used to fingerprint wild populations of Helichrysum, the chemical profiles being coherent with the systematic arrangement of the investigated populations in three main clusters, referring to the aggregates of H. stoechas, H. rupestre, and H. italicum, all belonging to the section Stoechadina. The correct nomenclatural designation of the investigated populations is discussed and the following two new combinations are proposed: Helichrysum preslianum subsp. compactum (Guss.) Maggio, Bruno, Guarino, Senatore & Ilardi and Helichrysum panormitanum subsp. latifolium Maggio, Bruno, Guarino, Senatore & Ilardi.

Essential-Oil Variability in a Collection of Ocimum basilicum L. (Basil) Cultivars.

Ocimum basilicum L. (Lamiaceae) is an aromatic plant of great tradition in the Mediterranean area. Its economic importance is growing up determining an expansion of cultivation. This paper evaluated the morphological traits, the chemical profiles, and antibacterial activity of 21 cultivars of basil belonging to 'Genovese', 'Napoletano', and 'Purple basil' types. The cultivars were characterized by different growth rate and morphological traits. The chemical composition of the oils analyzed by GC and GC/MS analysis, supported by the PCA analysis, underlined the strong influence of chemotype. It is noteworthy that estragole, never present in Genovese and purple basil types, occurred in Napoletano type. The high presence of eugenol, methyl eugenol, and linalool in the majority of cultivars, belonging both to Genovese and to Napoletano types was registered. Of great interest resulted the composition of the purple basil 'Opal'. All the samples tested exhibited similar antibiotic profiles with moderate antibacterial activity. The results enhanced the importance of determination of essential-oil profile in the selection of cultivars characterized by diverse morphological traits and are useful for different purposes.

Volatile constituents of the aerial parts of Pulicaria sicula (L.) Moris growing wild in Sicily: chemotaxonomic volatile markers of the genus Pulicaria Gaertn.

The chemical composition of the essential oil isolated from the aerial parts of Pulicaria sicula (L.) Moris was characterized by GC-FID and GC/MS analyses. The oil was particularly rich in oxygenated terpenoids. Among the oxygenated monoterpenes (content of 44.5%), the most abundant were borneol (23.7%), bornyl acetate (6.5%), and isothymol isobutyrate (6.2%). Caryophyllene oxide (10.2%), caryophylladienol I (4.3%), and caryophylla-3,8(13)-dien-5ß-ol (4.4%) were identified as the main constituents among the oxygenated sesquiterpenes. Furthermore, a complete literature review on the composition of the essential oils of all the Pulicaria taxa studied so far was performed and a principal component analysis (PCA) was carried out.

Cytotoxic activity and composition of petroleum ether extract from Magydaris tomentosa (Desf.) W. D. J. Koch (Apiaceae).

The petroleum ether extract of Magydaris tomentosa flowers (Desf.) W. D. J. Koch has been analyzed by GC-MS. It is mainly constituted by furanocoumarins such as xanthotoxin, xanthotoxol, isopimpinellin, and bergaptene. Other coumarins such as 7-methoxy-8-(2-formyl-2-methylpropyl) coumarin and osthole also occurred. The antiproliferative activity of Magydaris tomentosa flower extract has been evaluated in vitro on murine monocye/macrophages (J774A.1), human melanoma (A375) and human breast cancer (MCF-7) tumor cell lines, showing a major activity against the latter.

Chemical composition of the essential oils of three endemic species of Anthemis Sect. Hiorthia (DC.) R.Fern. growing wild in Sicily and chemotaxonomic volatile markers of the genus Anthemis L.: an update.

The chemical composition of the essential oils isolated from the aerial parts of Anthemis pignattiorum Guarino, Raimondo & Domina and A. ismelia Lojac. and the aerial parts and flowers of Anthemis cupaniana Tod. ex Nyman, three endemic Sicilian species belonging to the section Hiorthia, was determined by GC-FID and GC/MS analyses. (Z)-Muurola-4(14),5-diene (27.3%) was recognized as the main constituent of the A. pignattiorum essential oil, together with isospathulenol (10.6%), sabinene (7.7%), and artemisyl acetate (6.8%), while in the oil obtained from the aerial parts of A. ismelia, geranyl propionate (8.8%), bornyl acetate (7.9%), ß-thujone (7.8%), neryl propionate (6.5%), and τ-muurolol (6.5%) prevailed. α-Pinene was the main compound of both the aerial part and flower oils of A. cupaniana (18.4 and 13.2%, resp.). Also noteworthy are the considerable amounts of artemisyl acetate (12.7%) and ß-thujone (11.8%) found in the oil from the aerial parts and those of tricosane (9.8%) and sabinene (7.6%) evidenced in the flower oil. Furthermore, an update on the main compounds identified in the essential oils of all the Anthemis taxa studied so far was presented, and cluster analyses were carried out, to compare the essential oils of these taxa.

Phytomorphological and essential-oil characterization in situ and ex situ of wild biotypes of oregano collected in the Campania region (Southern Italy).

Oregano is an aromatic species of great interest, which spreads spontaneously over the Mediterranean area, but its genetic resources are not yet adequately developed. Moreover, the results of studies of wild strains of different origin - although quite numerous - are not always comparable, and, therefore, the influence of the environment and genotype on the variability cannot be distinguished. Hence, the plant morphology and the essential-oil composition of three wild, white-flowering biotypes of oregano collected in the Campania region (southern Italy) were characterized, and the effects of genotype and environment were assessed by comparison in situ and ex situ. This allowed deducing that the biotypes belonged to two different subspecies, i.e., Origanum vulgare ssp. virens and O. vulgare ssp. viridulum. The essential-oil yield was higher for the biotype belonging to ssp. virens, and it was significantly correlated with the glandular and stomatal density. The chemical composition of the oils obtained by hydrodistillation was found to be influenced by the genotype and the conditions of plant growth.

Chemical composition and biological activity of essential oils of Origanum vulgare L. subsp. vulgare L. under different growth conditions.

This research was aimed at investigating the essential oil production, chemical composition and biological activity of a crop of pink flowered oregano (Origanum vulgare L. subsp. vulgare L.) under different spatial distribution of the plants (single and binate rows). This plant factor was shown to affect its growth, soil covering, fresh biomass, essential oil amount and composition. In particular, the essential oil percentage was higher for the binate row treatment at the full bloom. The chemical composition of the oils obtained by hydrodistillation was fully characterized by GC and GC-MS. The oil from plants grown in single rows was rich in sabinene, while plants grown in double rows were richer in ocimenes. The essential oils showed antimicrobial action, mainly against Gram-positive pathogens and particularly Bacillus cereus and B. subtilis.

Phytochemical profile and apoptotic activity of Onopordum cynarocephalum.

A phytochemical investigation of acetone and chloroform extracts of the aerial parts of Onopordum cynarocephalum Boiss. et Blanche was carried out. It led to the isolation of two new sesquiterpenes, the elemane aldehyde (2) and the eudesmane (11), together with 15 known compounds: two lignans (1 and 15) and 13 sesquiterpenes (3-10, 12-14, 16, 17). The structures were elucidated by spectroscopic analyses, especially 1D and 2D NMR spectra. The anti-growth effect against three human melanoma cell lines, M14, A375, and A2058, of the different extracts and compounds of O. cynarocephalum was also investigated. Among them, the chloroform extract exhibited the strongest biological activity, while the most active compounds were the lignan arctigenin (1), and the sesquiterpenes, compounds 3, 5, and 6 belonging to the elemane type, and 7 belonging to the eudesmane type. Our data also demonstrate that acetone and chloroform extracts induce, in the A375 cell line, apoptotic cell death that could be related to an overall action of the compounds present, but in particular to the lignans arctigenin (1) and the sesquiterpenes compounds 3-8 and 16. In fact, these molecules were able to induce a high DNA fragmentation, correlated to a significant increase of the caspase-3 enzyme activity. Furthermore, apoptosis appears to be mediated, at least in part, via PTEN activity and the inhibition of Hsp70 expression.

Flavonoids in subtribe Centaureinae (Cass.) Dumort. (tribe Cardueae, Asteraceae): distribution and (13)C-NMR spectral data.

This review reports the occurrence of flavonoids in subtribe Centaureinae of Asteraceae family. It extensively covers the literature up to 2010 and collects all available (13)C-NMR data.

Chemical composition of essential oil from Italian populations of Artemisia alba Turra (Asteraceae).

The use of essential oils as chemotaxonomic markers could be useful for the classification of Artemisia species and to caracterize biodiversity in the different populations. An analysis of the chemical composition of four essential oils from Italian populations of Artemisia alba Turra (collected in Sicily, Marche and Abruzzo) was investigated. In this paper an in depth study of the significant differences observed in the composition of these oils is reported.

A study on the essential oil of Ferulago campestris: how much does extraction method influence the oil composition?

The essential oil of different parts of Ferulago campestris (Bess.) collected in Sicily has been extracted by microwave-assisted hydrodistillation (MAHD) and by classic hydrodistillation (HD). A comparative qualitative-quantitative study on the composition of the oils was carried out. A total of 100 compounds were identified in the oils obtained by MAHD, whereas 88 compounds characterized the HD oils. The most prominent components were, in all different parts of F. campestris and in both extraction methods, 2,4,5-trimethylbenzaldehyde and 2,4,6-trimethylbenzaldehyde isomers; the latter was not previously found. The attempt to evaluate where the oil components are located in all parts of the plant was carried out by means of a kinetic study. Then, electron microscopy observation on the different parts before and after MAHD and HD was performed.

Metabolite profile and in vitro activities of Phagnalon saxatile (L.) Cass. relevant to treatment of Alzheimer's disease.

The present study describes for the first time the in vitro properties (inhibition of NO production and anticholinesterase) of Phagnalon saxatile (L.) Cass. (Asteraceae). The methanolic extract showed antioxidant activity that was measured by DPPH assay and beta-carotene bleaching test. The same extract inhibited NO production in the murine monocytic macrophage cell line RAW 264.7. Acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition was assessed by modifications of Ellman's method. Purification of the MeOH extract of P. saxatile allowed the isolation of phenolic compounds. Among them, the compounds that most effectively inhibited lipopolysaccharide-induced NO production were caffeic acid and methylchlorogenic acid, with IC50 values of 7 microg/mL and 12 microg/mL, respectively. Luteolin and 3,5-dicaffeoylquinic acid exhibited the most promising activity against AChE with an IC50 of 25.2 and 54.5 microg/mL, respectively, while caffeic acid and luteolin exhibited higher activity against BChE with an IC50 of 32.2 and 37.2 microg/mL, respectively.

Essential oil composition of stems and fruits of Caralluma europaea N.E.Br. (Apocynaceae).

The essential oil of the stems and fruits of Caralluma europaea (Guss.) N.E.Br. (Apocynaceae) from Lampedusa Island has been obtained by hydrodistillation and its composition analyzed. The analyses allowed the identification and quantification of 74 volatile compounds, of which 16 were aromatic and 58 non-aromatic. Stems and fruits contained 1.4% and 2.7% of aromatic compounds respectively, while non-aromatic were 88.3% and 88.8%. Non-aromatic hydrocarbons were the most abundant compounds in both organs, followed by fatty acids. Data showed differences in the profiles between stems and fruits which shared only eighteen compounds; stems accounted for 38 compounds while fruits for 53. Fruits showed a higher diversity especially in aromatic compounds with twelve versus four in stems. Among the volatiles identified in stems and fruits of C. europaea 26 are present in other taxa of Apocynaceae, 52 are semiochemicals for many insects, and 21 have antimicrobial activity. The possible ecological role of the volatiles found is briefly discussed.

Antispasmodic effects and structure-activity relationships of labdane diterpenoids from Marrubium globosum ssp. libanoticum.

Marrubium globosum ssp. libanoticum is a medicinal plant used in Lebanon to reduce pain and smooth muscle spasms. A chloroform extract obtained from M. globosum aerial parts reduced acetylcholine-induced contractions in the isolated mouse ileum. The purification of this extract identified, among 12 isolated labdane diterpenoids, four new compounds, named 13-epicyllenin A (4), 13,15-diepicyllenin A (5), marrulibacetal (9), and marrulactone (11). Their structures were determined by spectroscopic methods. Compound 9, which exerted antispasmodic activity, is likely the active ingredient of the extract. Preliminary structure-activity relationships for this class of compounds are suggested.

Antiproliferative activity on human cancer cell lines after treatment with polyphenolic compounds isolated from Iris pseudopumila flowers and rhizomes.

The present study describes the antiproliferative properties of Iris pseudopumila flowers and rhizomes extracts and fourteen constituents isolated from them. The in vitro cytotoxic activity assay against two human cancer cell lines, large lung carcinoma (CORL-23) and amelanotic melanoma (C32), showed that the most antiproliferative extract was the MeOH extract from flowers with a percentage of inhibition of 50.9 at 100 microg/ml against amelanotic melanoma cells. The most antiproliferative compounds against amelanotic melanoma cells were kaempferol-3-O-beta-D-glucopyranoside and irisolidone with a percentage of inhibition of 100 and 96.6, respectively, and against large lung carcinoma cells with a percentage of inhibition of 82.1 and 84.6, respectively. Significant activity on the amelanotic melanoma cell line was also showed by irigenin-7-O-beta-D-glucopyranoside, with a percentage of inhibition of 89.3. The compounds isovitexin and isoorientin-6-O''-beta-D-glucopyranoside showed a selective activity against amelanotic melanoma cells with a percentage of inhibition of 83.2 and 79.8, respectively.

Chemical composition and antimicrobial activity of the essential oils from three chemotypes of Origanum vulgare L. ssp. hirtum (Link) Ietswaart growing wild in Campania (Southern Italy).

Essential oils obtained from inflorescences of three Origanum vulgare L.ssp. hirtum (Link) Ietswaart samples, growing wild in different locations in Campania (Southern Italy), were analysed. Three chemotypes were found: the first, with a prevalence of carvacrol/thymol; the second, characterized by the prevalence of thymol/alpha-terpineol; the third, featuring a prevalence of linalyl acetate and linalool. This chemical study attempts to provide a contribution in shedding light on the relationship between chemical composition and biotypes and/or chemotypes in Origanum vulgare ssp. hirtum. The essential oils were also evaluated for their antibacterial activity against 10 selected microorganisms. The data obtained contribute to the future view to use the essential oils as natural preservatives for food products, due to their positive effect on their safety and shelf life.

Headspace volatile composition of the flowers of Caralluma europaea N.E.Br. (Apocynaceae).

The volatile constituents of the flowers of Caralluma europaea (Guss.) N.E.Br (Apocynaceae) from Lampedusa Island were analyzed by a headspace GC method. The analyses allowed the identification and quantification of 41 compounds. The main components were, among the monoterpenoids, terpinolene (23.3%), alpha-terpinene (19.1%) and linalool (18.4%), whereas, among the carbonylic compounds the major constituents were heptanal (2.0%), octanoic acid (2.4%) and hexanoic acid (1.7%). The presence of a nitrogen containing compound, indole (0.8%) and of a sulphur containing compound, dimethylsulphide (t), noteworthy. The compounds found in the flowers of C. europaea have been compared with data available in the literature as regard to their odor, presence in other sapromyiophilous taxa, possible role as semiochemicals, and presence in decaying organic matter. 89.3% of total constituents have been described in other sapromyiophilous taxa. Some of the compounds are present in several types of decaying organic matter (excrements, decomposing bodies, and spoiled fish, etc). Several volatiles found in C. europaea flowers are used as semiochemicals by Hymenoptera, Coleoptera, Diptera, Lepidoptera and other insects. Sixteen volatiles, accounting for 32.4% of the total constituents, are described as attractants of some Diptera families, with a biology linked to decaying organic matter. Our data thus confirm that C. europaea floral bouquet falls within the sapromyiophilous pollination syndrome.

Chemical composition and antimicrobial activity of the essential oils from two species of Thymus growing wild in southern Italy.

The volatile constituents of the aerial parts of two samples of Thymus longicaulis C. Presl, collected in Campania and in Sicily, and two samples of Thymus pulegioides L. from the same regions, were extracted by hydrodistillation and analyzed. Considering the four oils together, seventy-eight different compounds were identified: 57 for Thymus longicaulis from Sicily (91.1% of the total oil), 40 for Thymus longicaulis from Campania (91.5% of the oil), 39 for Thymus pulegioides from Sicily (92.5% of the oil) and 29 for Thymus pulegioides from Campania (90.1% of the oil). The composition of the oils is different, although the most abundant components are identical in T. pulegioides. The essential oils showed antibacterial activity against eight selected microorganisms.

Chemical composition and phytotoxic effects of essential oils of Salvia hierosolymitana Boiss. and Salvia multicaulis Vahl. var. simplicifolia Boiss. growing wild in Lebanon.

The chemical composition of the essential oils of S. hierosolymitana Boiss. and S. multicaulis Vahl. var. simplicifolia Boiss. collected in Lebanon was studied by means of GC and GC-MS analysis. In all 115 compounds were identified: 82 for S hierosolymitana and 72 for S. multicaulis var. simplicifolia. The presence of carbonylic compounds (17%) characterizes the oil from S. hierosolymitana,while S. multicaulis var. simplicifolia oil is rich of monoterpenes (34.5%) and sesquiterpenes (46.9%). The effects of the essential oils on germination and initial radical elongation of Raphanus sativus L. (radish) and Lepidium sativum L. (garden cress) were studied, indicating in a different activity against radical elongation of the species tested.

Chemical composition of essential oils of Anthemis secundiramea Biv. subsp. secundiramea (Asteraceae) collected wild in Sicily and their activity on micro-organisms affecting historical art craft.

In the present study, the chemical composition of the essential oil from the aerial parts of Anthemis secundiramea Biv. subsp. secundiramea L. collected in Sicily was evaluated by GC and gas chromatography-mass spectrometry. The main components of A. secundiramea were (Z)-lyratyl acetate (14.6%), (Z)-chrysanthenyl acetate (9.9%), (Z)-chrysanthenol (8.7%) and (E)-chrysanthenyl acetate (7.7%). The comparing with other studied oils of genus Anthemis belonging to the same clade is discussed. Antibacterial and antifungal activities against some micro-organisms infesting historical art craft, were also determined.