Screening of the essential oil of Thapsia garganica subsp. messanensis (Guss.) Brullo & al., an endemic plant of Sicily (Italy).

The genus Thapsia L., belonging to the Scandiceae tribe of the Apiaceae family, is mainly distributed in the Mediterranean area, North Africa, and the Iberian Peninsula. The use of plants of this genus in popular medicine dates back to the age of ancient Greeks. In the present study the chemical composition of the essential oil from aerial parts of Thapsia garganica subsp. messanensis (Guss.) Brullo & al., an endemic plant of Sicily, never previously investigated, was evaluated by GC-MS. The main components of its essential oil (Tgm) were 1,4-dimethylazulene (17.0%), chamazulene (10.1%), 3-methyl nonane (7.0%), and butyl heptanoate (4.6%). The comparison with all the other studied essential oils of the genus Thapsia is discussed.

The essential oil composition of Phlomis bovei subsp. maroccana Maire, an endemic species of Morocco.

Phlomis L. is a genus belonging to the Lamiaceae family, distributed in Macaronesia, the Mediterranean basin, Northeast Africa, Central Asia, and Western Himalaya. Plants of this genus are used against various diseases in the ethno-medicine of several countries and some of them are also utilised for culinary purposes. In the present study, the essential oil chemical composition of the aerial parts of Phlomis bovei subsp. maroccana Maire, an endemic species of Morocco, was analysed by GC-MS. No previous paper has been previously published on this taxon. Main constituents of the essential oil were sesquiterpene hydrocarbons (44.48%) with curcumene (11.20%), a very rare compound in Phlomis essential oils, ß-himachalene (6.22%), and ß-cedrene (3.81%) as principal metabolites. 1-hexadecanol (7.75%) and 1-octadecanol (5.32%) were the main constituents among the alcohols (19.66%). A comparison with all the other essential oils from Phlomis taxa has been carried out.

The chemical composition of the aerial parts' essential oil of Limonium lobatum (L.f.) Chaz. growing wild in Algeria.

The Limonium genus (Plumbaginaceae) includes several species of perennial herbs and shrubs belonging to a particular type of halophytes, known as 'recretohalophytes'. Limonium species are widely distributed in the Mediterranean region, mainly in the North-Eastern and Southern countries and several bioactivities have been well documented. In the present study, the chemical composition of the essential oil (EO) of the aerial parts of Limonium lobatum (L.f.) Chaz., a species never chemically previously studied and collected in Algeria, which grows in South Spain, North Africa, and SW Asia, was analysed using GC-MS. The main constituents of the EO were monoterpenes involving eucalyptol (14.21%), ß-pinene (8.62%), ß-myrcene (8.18%). Among the sesquiterpene compounds ß-caryophyllene (8.94%) was the major one. The chemical profile of the EO presented here was compared with the EOs of previously investigated Limonium taxa. Furthermore, a complete literature review on the ethno-pharmacological uses of Limonium species was performed.

Phytochemical profile, in vitro antioxidant and antibacterial activities of different extracts of an Algerian endemic: Teucrium atratum.

Teucrium atratum Pomel. is a species belonging to the Lamiaceae family used in Algerian folk medicine. The present work essentially aimed to assess the phenolic composition and to evaluate some of the biological effects of different extracts, never previously studied, of T. atratum growing in Algeria. High levels of total phenolic and flavonoids were recorded in the hydromethanolic extract. Chlorogenic acid, isoquercetin, coumarin, cinnamic acid, quercetin dihydrate, and catechin were identified in the methanolic extract by mean of HPLC. The antioxidant activity assessed showed that the methanolic extract was the most active, while, the hydromethanolic extract showed a great power to reduce iron. In addition, all extracts had a significant antibacterial effect against the four tested bacterial strains, with Staphylococcus aureus as the most sensitive one. These findings can be a starting point to evaluate the plant as a source of natural bioactive compounds with antioxidant and antibacterial effects.

Phytochemical Characterization, Antioxidant, and Anti-Proliferative Activities of Wild and Cultivated Nigella damascena Species Collected in Sicily (Italy).

The use of Nigella damascena seeds in the culinary field or as aerial parts infusions in the pharmaceutical and cosmetic fields is widely reported. The biological activity of this plant, as demonstrated over the years, is closely related to its phytochemical content. This investigation focused on the comparative study of the same plants of N. damascena, one totally wild (WND), while the other two, one with white flowers (CWND) and the other with blue flowers (CBND), were subject to cultivation, irrigation, and manual weeding. Using the potential of 1D and 2D-NMR spectroscopy, coupled with MS/MS spectrometric studies, the three methanolic extracts of N. damascena were investigated. Chemical studies have highlighted the presence of triterpene saponin compounds and various glycosylated flavonoids. Finally, the in vitro antiproliferative and antioxidant activities of the three individual extracts were evaluated. The antiproliferative activity performed on U-937, HL-60, and MCF-7 tumor cell lines highlighted a greater anticancer effect of the CBND and CWND extracts compared to the data obtained using WND. The antioxidant activity, however, performed to quantify ROS generation is comparable among the extracts used.

Paeonia mascula subsp. russoi (biv.) Cullen & Heywood: the chemical composition of the aerial parts essential oils of two different populations collected in Sicily (Italy).

In the present study, the chemical composition of the essential oil from aerial parts of two populations of Paeonia mascula subsp. russoi, collected in Sicily, was evaluated by GC-MS. No previously phytochemical investigation has been reported for this subspecies. The main components of the essential oil of the population with pink flowers were salicylaldehyde (34.31%), nonanal (16.95%) and 2-hexenal (10.17%), whereas essential oil of the population with white flowers, was shown to be rich of myrtanal (14.14%), eugenol (14.02%) and salicylaldehyde (12.21%). Furthermore, a complete literature review, not present in literature, on the composition of the essential oils of all the other taxa of Paeonia, studied so far, was performed. PCA and HCA analyses of the composition of essential oils obtained from the aerial parts were also carried out.

Synthetic Derivatives of Natural ent-Kaurane Atractyligenin Disclose Anticancer Properties in Colon Cancer Cells, Triggering Apoptotic Cell Demise.

The antitumor activity of different ent-kaurane diterpenes has been extensively studied. Several investigations have demonstrated the excellent antitumor activity of synthetic derivatives of the diterpene atractyligenin. In this research, a series of new synthetic amides and their 15,19-di-oxo analogues obtained from atractyligenin by modifying the C-2, C-15, and C-19 positions were designed in order to dispose of a set of derivatives with different substitutions at the amidic nitrogen. Using different concentrations of the obtained compounds (10-300 µM) a reduction in cell viability of HCT116 colon cancer cells was observed at 48 h of treatment. All the di-oxidized compounds were more effective than their alcoholic precursors. The di-oxidized compounds had already reduced the viability of two colon cancer cells (HCT116 and Caco-2) at 24 h when used at low doses (2.5-15 µM), while they turned out to be poorly effective in differentiated Caco-2 cells, a model of polarized enterocytes. The data reported here provide evidence that di-oxidized compounds induced apoptotic cell death, as demonstrated by the appearance of condensed and fragmented DNA in treated cells, as well as the activation of caspase-3 and fragmentation of its target PARP-1.

Glucose Uptake-Stimulating Metabolites from Aerial Parts of Centaurea sicula.

A comprehensive phytochemical investigation of aerial parts obtained from Centaurea sicula L. led to the isolation of 14 terpenoids (1-14) and nine polyphenols (15-23). The sesquiterpenoid group (1-11) included three structural families, namely, elemanolides (1-6), eudesmanolides (7 and 8), and germacranolides (9-11) with four unreported secondary metabolites (5-8), whose structure has been determined by extensive spectroscopic analysis, including 1D/2D NMR, HR-MS, and chemical conversion. Moreover, an unprecedented alkaloid, named siculamide (24), was structurally characterized, and a possible biogenetic origin was postulated. Inspired by the traditional use of the plant and in the frame of ongoing research on compounds with potential activity on metabolic syndrome, all the isolated compounds were evaluated for their stimulation of glucose uptake, disclosing remarkable activity for dihydrocnicin (10) and the lignan salicifoliol (15).

The chemical composition of the aerial parts' essential oil of matthiola fruticulosa (L.) maire growing in Sicily, Italy.

Matthiola Aiton is a genus belonging to the Brassicaceae family, distributed in Macaronesia, the Mediterranean basin, and the Saharo-Sindian region. Plants of this genus are used against various diseases in the ethno-medicine of several countries and a complete review of their usage has been carried out in this paper. In the present study, the essential oil chemical composition of the aerial parts of the Sicilian accession of Matthiola fruticulosa (L.) Maire, a species growing in South-Western Europe, Northern Africa, and Western Asia, was analysed by GC and GC-MS. No previous paper has been previously published on the essential oil of this species. Main constituents of the oil were sulphur compounds (45.5%) with the two quite rare cis and trans isomers of 5-(methylthio)-4-pentenenitrile as principal metabolites (16.3% and 10.7%, respectively). Principal compound of the oil was the diterpene phytol (16.5%) whereas other terpenoids were less abundant (10.6%).

Seseli tortuosum L. subsp. tortuosum Essential Oils and Their Principal Constituents as Anticancer Agents.

Seseli tortuosum L. subsp. tortuosum, belonging to the Apiaceae family, is a species that grows in Europe, mainly in the Mediterranean regions. The history of its application in traditional medicine highlights its various biological properties. Trying to explore the phytochemistry and pharmacological aspects of this species, the essential oils (EOs) extracted from flowers, stems, and roots of a locally wild accession, never previously investigated, growing in Sicily, Italy, were investigated. The chemical composition of all EOs, obtained by the hydrodistillation method, was evaluated by GC-MS. The most abundant class of all investigated samples was that of monoterpene hydrocarbons (79.98-91.21%) with p-cymene, α-pinene, ß-pinene, and ß-ocimene as major compounds. These EOs, and their main components, were tested for their possible anticancer activity. Obtained data provided evidence that among the different EOs tested, at the dose of 100 µg/mL, those extracted from stems and roots were particularly effective, already at 24 h of treatment, in reducing the cell viability of 42% and 95%, respectively, in HCT116 colon cancer cell line. These EOs also exerted a remarkable cytotoxic effect that was accompanied by morphological changes represented by cell shrinkage as well as a reduction in residual cell population. Differently, modest effects were found when EOs extracted from flowers were tested in the same experimental conditions. The evaluation of the phytocompounds mainly represented in the EOs extracted from different parts of the plant and tested in a range of concentrations between 20 and 200 µg/mL, revealed that α-pinene, ß-pinene, and p-cymene exerted only modest effects on cell viability. Differently, a remarkable effect was found when ß-ocimene, the most abundant phytocomponent in EOs from roots, was tested on colon cancer cells. This phytocompound, among those identified in EOs from Seseli tortuosum L. subsp. tortuosum, was found to be the most effective in reducing colon cancer cell viability with IC50 = 64.52 µg/mL at 24 h of treatment. All together, these data suggest that ß-ocimene could be responsible for the effects observed in colon cancer cells.

The chemical composition of the aerial parts essential oils of Centaurea erycina (Asteraceae), an endemic species of Sicily (Italy).

In the present study, the chemical composition of the essential oil from aerial parts of a very rare Centaurea species, not previously investigated, Centaurea erycina Raimondo and Bancheva, collected in Sicily, was evaluated by GC-MS. The new species, classified just twenty years ago, belongs to Centaurea cineraria group (sect. Pannophyllum Hayek, Asteraceae) and grows in an extremely limited area in the NW part of Sicily. The oil was shown to be rich of aldehydes (41.4%) and sesquiterpenes (33.4%). The main components of the essential oil were ß-caryophyllene (13.4%), caryophyllene oxide (12.6%), hexanal (11.9%), and trans-2-hexenal (10.0%). Furthermore, a complete literature review on the composition of the essential oils of all the other taxa of Centaurea, belonging to sections Pannophyllum, studied so far, was carried out.

Phytochemical investigation and antitumor activity of coumarins from Sicilian accession of Ferulago nodosa (L.) Boiss. roots.

Ferulago nodosa (L.) Boiss. (Apiaceae) is a species occurring in the Balkan-Tyrrhenian area being present in Crete, Greece, Albania, and probably in Macedonia. From the roots of this accession of species, not previously investigated, four coumarins, grandivittin, aegelinol benzoate, felamidin and aegelinol, and two terpenoids, (2E)-3-methyl-4-[(3-methyl-1-oxo-2-buten-1yl)oxy]-2-butenoic acid and pressafonin-A, were isolated and spectroscopically characterized. The last one was never detected in Ferulago species. The evaluation of the anti-tumor effects of F. nodosa coumarins on colon cancer HCT116 cells showed only a modest effect on reduction of tumor cell viability. For aegelinol, the reduction of colon cancer cell viability already appears with 25 µΜ, while using 50 e 100 µM doses of marmesin the residual viability amounted to 70% and 54%, respectively. This effect resulted more evident at higher doses of compounds (at 200 µM from 80% to 0%). The most effective compounds resulted coumarins lacking ester group.

The Biological Properties of the Essential Oil from the Jordan Accession of Phagnalon sinaicum Bornm. & Kneuck.

The genus Phagnalon Cass. (Asteraceae) is composed of widely distributed species and most of them, due to the medicinal properties they possess, are widely used in folk medicine but also as spices in the culinary field. The polar and non-polar extracts, as well as the complex mixtures of their essential oils, from several Phagnalon species and ssp., have shown antibiotic, antiviral, cytotoxic, and several other biological properties. In this work, the chemical composition and the antimicrobial, cytotoxic, and antioxidant properties of the Jordan accession of Phagnalon sinaicum Bornm. & Kneuck. essential oil (EO), an extremely rare plant that grows in ravines in the Middle East, were investigated. The EO, analyzed by GC-MS, was found to be rich in terpenoid compounds, and, in particular, in oxygenated monoterpenes, with the main compound being artemisia ketone (22.3%), followed by α-thujone (17.7%), and santolin alcohol (14.8%). The EO had good antimicrobial activity, especially against Escherichia coli Gram-negative bacterium (3 mg/mL MIC values) and was also effective in counteracting in vitro biofilm formation. Furthermore, this EO showed low cytotoxicity against immortalized human keratinocytes lines, but had good antioxidant activity on the same eukaryotic cellular models.

The chemical composition of the aerial parts' essential oil of Geocaryum capillifolium (Guss.) Coss growing in Sicily (Italy).

The three genera Geocaryum Coss., Conopodium W.D.J. Koch, and Bunium L. are closely related, and their correct identification is complex. The first two genera are distributed in Europe and North Africa, while several Bunium species also occur in Asia. In the present study, we analysed the chemical composition of the essential oil of the aerial parts of Geocaryum capillifolium (Guss.) Coss. a rare species collected in Sicily, which also grows in the Iberian Peninsula, Algeria, and Greece, was analysed using GC-MS. The main constituents of the essential oil were sesquiterpene hydrocarbons involving cis-ß-farnesene (31.2%), trans-ß-caryophyllene (20.0%), and germacrene D (8.5%). The chemical profile of the essential oil presented here was compared with the oils of previously investigated Geocaryum, Conopodium, and Bunium taxa, as reported in the literature. To the best of our knowledge, no report has been previously published about the essential oil of the Sicilian accession of this species.

The chemical composition of the aerial parts' essential oil of Cynoglossum clandestinum Desf. growing in Sicily, Italy.

Cynoglossum L. is a taxonomically difficult genus belonging to the Boraginaceae family, distributed in Asia, Europe, mainly in Turkey, and in the Mediterranean region. Plants of this genus are used against various diseases in the ethnomedicine of several countries. In the present study, the chemical composition of the essential oil was obtained from the hydrodistillation of aerial parts of the Sicilian accession of Cynoglossum clandestinum Desf. was analysed by GC and GC-MS. The main constituents of the essential oil were aldehydes and ketones (69.9%) with nonanal (18.9%), 4-sec-butoxy-2-butanone (18.1%), and 3-methyl-butanal (13.1%) as main metabolites. No one paper has been previously published on the essential oil of this species, and there is a lack of studies also in the near related genera. The aim of this work is in fact, to study a species that has never been investigated, and through this, try to help place it within the Boraginaceae family.

Essential oil of Apium nodiflorum (L.) Lag. growing in Ksob River, Algeria.

The essential oil from the aerial parts of Apium nodiflorum (L.) Lag. (Apiaceae), collected in Ksob River (Algeria) and obtained by hydrodistillation, was analysed by GC-MS. Sixty-seven components have been identified, representing more than 98.7% of the total oil. The essential oil was found to be rich in terpinolene (32.9 ± 4.6%), myristicin (10.6 ± 2.3%), myrcene (6.2 ± 1.1%), limonene (6.0 ± 0.9%), γ-terpinene (5.9 ± 1.2%) and (Z)-caryophyllene (5.3 ± 1.0%).

The chemical composition of the essential oils of two Mediterranean species of Convolvulaceae: Convolvulus althaeoides subsp. tenuissimus collected in Sicily (Italy) and Calystegia silvatica collected in Algeria.

Convolvulus L. and Calystegia R.Br. are two closely related genera of the Convolvulaceae family distributed in Asia, Mediterranean, Macaronesia, East Africa, and Arabia, including about 210 and 30 accepted species, respectively, of flowering plants, present as trees, shrubs, and herbs. The ethnomedical use of Convolvulus species dates to 1730s as they displayed profuse medicinal properties. In the present study, the not previously investigated chemical compositions of the essential oils from aerial parts of Convolvulus althaeoides subsp. tenuissimus (Sm.) Bat., collected in Sicily, and Calystegia sylvatica (Kit.) Griseb., collected in Algeria, were evaluated by GC-MS. The main components of the essential oil of the first one were ß-caryophyllene (28.68%), γ-muurolene (23.75%), and γ-elemene (17.55%), whereas the C. silvatica essential oil was shown to be rich of valeranone (10.77%), viridiflorol (9.45%), and germacrene D (8.61%). Furthermore, a complete literature review on the ethno-pharmacological uses of Convolvulus and Calystegia species was performed.

The chemical composition of the aerial parts essential oils of four Andryala species (Asteraceae) growing wild in Morocco.

Andryala (Asteraceae: Cichorieae) is a little-known Mediterranean-Macaronesian genus whose taxonomy is very much in need of revision. In the present study, the chemical composition of the essential oils (EOs) from aerial parts of as many Andryala species, A. integrifolia, A. cossyrensis, and A. rothia, never studied before, and of A. pinnatifida subsp. mogadorensis, all collected in Morocco, was evaluated by GC-MS. The main components of the EOs of A. integrifolia and A. pinnatifida subsp. mogadorensis were organic acid compounds (41.10% and 43.52%, respectively), whereas A. cossyrensis, and A. rothia were shown to be rich in alkane derivatives (43.10% and 34.29%, respectively). Aldehydic compounds were the second class of metabolites in A. integrifolia and A. rothia (26.67% and 21.91%, respectively), whereas terpenoids, represented in all the four species in limited amounts, were more abundant only in A. pinnatifida subsp. mogadorensis (9.90%) and A. rothia (11.79%) species.

Chemical composition, antimicrobial, and antioxidant activities of Opuntia stricta (Haw.) Haw. mucilage collected in Sicily, Italy.

In this work the mucilage obtained from the cladodes of a not previously investigated accession of Opuntia stricta (Haw.) Haw. (syn. Opuntia dillenii (Ker-Gawl) Haw), collected in Sicily, was analysed by 13C-NMR. The yield of mucilage extracted from cladodes in aqueous medium was 2.55%. The monosaccharides identified, after acidic hydrolyses of the mucilage, were arabinose (36.48%), galactose (32.31%), xylose (15.33%), glucose (10.45%) and rhamnose (5.40%). The mucilage showed a sufficient antimicrobial activity and excellent antioxidant property.

Chemical Composition of Salvia fruticosa Mill. Essential Oil and Its Protective Effects on Both Photosynthetic Damage and Oxidative Stress in Conocephalum conicum L. Induced by Environmental Heavy Metal Concentrations.

The genus Salvia L., belonging to the Lamiaceae family, contains more than 900 species distributed in various parts of the world. It is a genus containing aromatic plants used both in the culinary field and above all in the cosmetic area to produce several perfumes. Salvia fruticosa Mill., notoriously known as Greek Salvia, is a plant used since ancient times in traditional medicine, but today cultivated and used in various parts of Europe and Africa. Polar and apolar extracts of this plant confirmed the presence of several metabolites such as abietane and labdane diterpenoids, triterpenoids, steroids, and some flavonoids, causing interesting properties such as sedative, carminative, and antiseptic, while its essential oils (EOs) are mainly characterized by compounds such as 1,8-cineole and camphor. The aim of this work concerns the chemical analysis by GC and GC-MS, and the investigation of the biological properties, of the EO of S. fruticosa plants collected in eastern Sicily. The gas-chromatographic analysis confirmed the presence of 1,8-cineole (17.38%) and camphor (12.81%), but at the same time, also moderate amounts of α-terpineol (6.74%), ß-myrcene (9.07%), camphene (8.66%), ß-pinene (6.55%), and α-pinene (6.45%). To study the protective effect of EOs from S. fruticosa (both the total mixture and the individual compounds) on possible damage induced by heavy metals, an in vitro system was used in which a model organism, the liverwort Conocephalum conicum, was subjected to the effect of a mix of heavy metals (HM) prepared using values of concentrations actually measured in one of the most polluted watercourses of the Campania region, the Regi Lagni. Finally, the antioxidant response and the photosynthetic damage were examined. The exogenous application of the EO yields a resumption of the oxidative stress induced by HM, as demonstrated by the reduction in the Reactive Oxygen Species (ROS) content and by the increased activity of antioxidant enzyme catalase (CAT) and glutathione-S-transferase (GST). Furthermore, plants treated with HMs and EO showed a higher Fv/Fm (maximal quantum efficiency of PSII in the dark) with respect to HMs-only treated ones. These results clearly indicate the protective capacity of the EO of S. fruticosa against oxidative stress, which is achieved at least in part by modulating the redox state through the antioxidant pathway and on photosynthetic damage.