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.

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 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%).

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 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.

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 oil of Pulicaria odora (L.) Rchb. growing in Sicily (Italy).

The genus Pulicaria Gaertn. (Asteraceae) comprises more than ninety-two species as annual or perennial herbs or small shrubs, distributed in Africa, Europe, and Asia, and concentrated mainly in the Mediterranean region. Several species have been used in the traditional medicine of many countries. In the present study the chemical composition of the essential oil from aerial parts of Pulicaria odora (L.) Rchb., present in the Mediterranean region and collected in Sicily, was analysed by GC-MS. No papers have been previously published on the essential oil of the aerial part of this species. The result showed the presence of large quantity of carbonyl compounds (25.29%), oxygenated sesquiterpenes (23.28%) and thymol derivatives (16.76%). Chemical considerations with respect of other oils of Pulicaria taxa were carried out.

Chemical composition of the essential oils of three taxa of Cytisus growing wild in Sicily, Italy.

The genus Cytisus is native Canary Islands, Europe to Mediterranean, Morocco, Algeria and Tunisia and several species of the genus are used in folk medicine of different countries. In this work the chemical composition of the essential oils from the aerial parts of three taxa of this genus growing wild in Sicily, Cytisus scoparius (L.) Link, C. villosus Pourr. and C. aeolicus Guss., has been investigated. No one report has been published on the Sicilian accession of the former two species, and, at the best of our knowledge, C. aeolicus is devoid of any chemical investigation. Cytisus scoparius and C. aeolicus essential oils have similar composition characterised by the occurrence of almost the same amount of compounds belonging to "other" class (59.5-52.0%) and carbonyl compounds (22.2-19.6%). Cytisus villosus showed a different composition with hydrocarbons as the main class (52.0%), totally absent in the other two species.

The chemical composition of the aerial parts' essential oil of Nepeta apuleji Ucria (Lamiaceae) growing in Sicily (Italy).

The genus Nepeta L. (Lamiaceae) comprises about 300 species as annual or perennial herbs or small shrubs, spread in central and southern Europe, the Near East, central and southern Asia, and some areas of Africa. Several species have been used in the traditional medicine. In the present study, the chemical composition of the essential oils from aerial parts of two populations of Nepeta apuleji Ucria collected in Sicily, a rare species, growing also in South Spain and NW Africa, were analysed by GC-MS. No one has been previously worked and published on the essential oil of this species. Main constituents of the two oils of the two populations were the monoterpenes ß-pinene (11.6-6.3%) and γ-terpinene (9.4-5.0%), and the sesquiterpenes ß-caryophyllene (11.9-9.8%) and germacrene D (1.8-13.0%). The chemical profile of the two essential oils presented herein and they compared with previously investigated Nepeta taxa oils, reported in the article.

Seseli bocconei Guss. and S. tortuosum subsp. maritimum Guss. essential oils inhibit colon cancer cell viability.

In this study, the chemical compositions of two essential oils (EOs) obtained from different parts (flowers, leaves, stems, and roots) of Seseli bocconei Guss. and of Seseli tortuosum subsp. maritimum Guss., wild endemic species of Sicily, were investigated. The main classes of metabolites for the essential oils of S. bocconei were, respectively, monoterpenes hydrocarbons for flowers, sesquiterpenes hydrocarbons for leaves, and a breakdown between the two previously mentioned classes for stems. In the case of S. tortuosum subsp. maritimum, on the other hand, the main metabolite class for all the vegetative parts analyzed (flowers, stems, and roots) was monoterpene hydrocarbons, with a slight percentage in other non-terpenoid compounds. Furthermore, the EOs' antitumor effects against HCT116, human colon cancer cells were evaluated. Cell viability assays evidenced that stems' EOs of both plants exhibit strong cytotoxic effects at low concentrations, while the EOs from other vegetative parts do not show a relevant effect. In fact, EO of stems of S. tortuosum subsp. maritimum reduced the cell viability of 82% at the concentration of 125 µg/mL, while at the concentration of 250 µg/mL of stems EO of S. bocconei the 97% of cells resulted dead. The analysis of the effects exerted by the main phytocostituents (S-(-)-limonene, R-(+)-limonene, sabinene, (1S)-(-)-α-pinene, (1R)-(+)-α-pinene, and (-)-ß-pinene, and germacrene D) of these EOs on colon cancer cells revealed germacrene D as a new promising molecule with anticancer properties that deserve to be explored in future directions.

The chemical composition of the aerial parts essential oil of Stachys ocymastrum L. Briq. (Lamiaceae) growing in Sicily (Italy).

The genus Stachys L. (Lamiaceae) comprises more than 300 species as annual or perennial herbs or small shrubs, spread in temperate regions of Mediterranean, Asia, America, and Southern Africa. Several species have been used in the traditional medicine to treat stress, skin inflammations, gastrointestinal disorders, asthma, and genital tumours. In the present study the chemical composition of the essential oil from aerial parts of Stachys ocymastrum L. Briq., belonging to section Olisia, endemic of the Western Mediterranean and Greece and collected in Sicily, was analysed by GC-MS. No one report has been previously published on any European accession of this species. The result showed the presence of large quantity of the diterpenoid phytol (23.80%). Other metabolites present in high quantity were ß-caryophyllene (17.95%), geranyl-α-terpinene (13.26%) and trans-chrysanthenyl acetate (9.85%). Chemical considerations with respect all the other oils of Stachys taxa, belonging to section Olisia studied so far, were carried out.

Chemical composition and antioxidant activities of the essential oil of Tordylium apulum L. collected in Sicily.

The genus Tordylium L. (Apiaceae) is distributed in almost all the countries bordering the Mediterranean. They are plants widely used in ethnomedicine in various countries, especially in the Eastern part of Mediterranean, and, furthermore largely used as food. Consequently, in order to evaluate not only the chemical aspects but also the biological properties, the essential oil (EO), obtained from the Sicilian accession of Tordilym apulum L., not previously studied, were investigated. The chemical composition of the essential oil, obtained by classical hydrodistillation and GC-MS analysis, showed the occurrence of large amount of monoterpene hydrocarbons (68.8%) containing huge quantity of ß-cis-ocimene (65.0%). The second most abundant metabolite was octyl hexanoate (14.4%), that can be considered a marker of genus Tordylium. ROS levels and the activity of antioxidant enzymes SOD and CAT on normal and OZ-stressed PMNs were measured in order to study the effects of EO of T. apulum.

Thymus richardii subsp. nitidus (Guss.) Jalas Essential Oil: An Ally against Oral Pathogens and Mouth Health.

The genus Thymus L., belonging to the Lamiaceae family, contains about 220 species with a distribution that mainly extends in Europe, northwest Africa, Ethiopia, Asia, and southern Greenland. Due to their excellent biological properties, fresh and/or dried leaves and aerial parts of several Thymus ssp. have been utilized in the traditional medicine of many countries. To evaluate not only the chemical aspects but also the biological properties, the essential oils (EOs), obtained from the pre-flowering and flowering aerial parts of Thymus richardii subsp. nitidus (Guss.) Jalas, endemic to Marettimo Island (Sicily, Italy), were investigated. The chemical composition of the EOs, obtained by classical hydrodistillation and GC-MS and GC-FID analyses, showed the occurrence of similar amounts of monoterpene hydrocarbons, oxygenated monoterpenes, and sesquiterpene hydrocarbons. The main constituents of the pre-flowering oil were ß-bisabolene (28.54%), p-cymene (24.45%), and thymol methyl ether (15.90%). The EO obtained from the flowering aerial parts showed as principal metabolites ß-bisabolene (17.91%), thymol (16.26%), and limonene (15.59%). The EO of the flowering aerial parts, and its main pure constituents, ß-bisabolene, thymol, limonene, p-cymene, and thymol methyl ether were investigated for their antimicrobial activity against oral pathogens and for their antibiofilm and antioxidant properties.

The chemical composition of the aerial parts essential oil of Ferulago nodosa (L.) Boiss. (Apiaceae) growing wild in Crete (Greece).

Ferulago nodosa (L.) Boiss. (Apiaceae) is a species occurring in the Balkan-Tyrrhenian area being present in Crete, Greece, Albania, and probably in Macedonia. Although the western disjointed population of Sicily has been classified as an endemic sub-species, F. nodosa subsp. geniculata (Guss.) Troia & Raimondo, its official acceptance is quite controversial. In order to verify the existence of two different sub-species, we investigated the chemical composition of the essential oil of F. nodosa, collected in Crete (Greece), not previously reported, and we compared it with the previously oil compositions reported in literature. Main constituents of the Cretan accessions of F. nodosa were trimethyl benzaldehyde derivatives (29.5%) and monoterpene hydrocarbons (56.14%).

Chemical composition, antimicrobial and antioxidant activities of the essential oil of Italian Prangos trifida (Mill.) Herrnst. & Heyn.

In this work, the essential oil of the aerial parts of a not previously investigated accession of Prangos trifida (Mill.) Herrnst. & Heyn (Apiaceae), collected in Northern Italy, was analysed by GC/MS. Twenty-five compounds were identified, accounting for 91.30% of the total oil, which is characterised by a high content of monoterpene hydrocarbons (71.26%). The main constituents of the essential oil were cis-ß-ocimene (18.12%), α-phellandrene (12.14%), sylvestrene (11.32%), p-mentha-1,3,8-triene (9.56%) and α-pinene (8.85%). The essential oil of P. trifida showed a good antimicrobial activity directed above all against Gram-positive bacteria, and had an interesting antioxidant activity, thus making it an excellent candidate for future cosmetic and pharmaceutical applications.

The chemical composition of essential oil from Seseli tortuosum subsp. tortuosum and S. tortuosum subsp. maritimum (Apiaceae) aerial parts growing in Sicily (Italy).

Seseli L. genus, belonging to the Apiaceae family, includes more than eighty taxa, mainly growing in Europe and Asia. Due to the several biological properties, species of this genus have been largely investigated, showing to be a rich source of coumarins, as well as, of essential oils with anti-inflammatory, antiviral, antifungal, cytotoxic, etc. properties. In the present study, the chemical composition of the essential oils from aerial parts of Sicilian accessions of Seseli tortuosum subsp. tortuosum and S. tortuosum subsp. maritimum were analysed by GC-MS. No one report has been previously published on the subsp. maritimum. The results showed the presence, in both oils, of large quantity of monoterpene hydrocarbons. Main metabolites were ß-pinene (15.81-19.84%), α-pinene (14.63-18.52%), sylvestrene (11.18-17.45%) and 3-carene (14.58%), the last one being absent in the oil of subsp. maritimum. Chemotaxonomic considerations with respect to other oils of Seseli taxa were carried out.

The chemical composition of essential oil from Seseli bocconei (Apiaceae) aerial parts growing in Sicily (Italy).

Seseli is a large genus of aromatic and economically important herbs of the Apiaceae family that includes eighty-seven taxa, mainly distributed in Europe and Asia. Several species of this genus are extensively used in various popular medicines and based on their traditional uses, much research concerning biological activities have been carried out. In the present study, the chemical composition of the essential oil from aerial parts of Seseli bocconei Guss., a rare plant endemic of Sicily, was analysed by GC-MS. No one report has been previously published on the essential oil of this species. The result showed the presence of large quantity of monoterpene and sesquiterpene hydrocarbons whereas it was practically devoid of oxygenated terpenes. Main metabolites of the oil were germacrene D (18.48%) and sabinene (17.46%). Chemotaxonomic considerations with respect to other oils of Seseli taxa were carried out.

A new ferulol derivative isolated from the aerial parts of Ferulago nodosa (L.) Boiss. growing in Sicily (Italy).

Ferulago nodosa (L.) Boiss. (Apiaceae) is a species occurring in the Balkan-Tyrrhenian area being present in Crete, Greece, Albania, and probably in Macedonia. Although the western disjointed population of Sicily has been classified as an endemic sub-species, F. nodosa subsp. geniculata (Guss.) Troia & Raimondo, it is not officially accepted. From the aerial parts of the Sicilian accession of this species four known metabolites (1-4), and a new ferulol derivative (5), were isolated and characterized. The structure of the new compounds was determined by mean of extensive NMR spectroscopic experiments.