Volatile constituents of Calamintha origanifolia boiss. Growing wild in Lebanon

The essential oil of aerial parts of Calamintha origanifolia Boiss. (Lamiaceae), growing wild in Lebanon, was obtained by hydrodistillation and was analysed by GC and GC-MS. 49 compounds, representing 92.2% of the oil, were identified. The major components, belonging to the class of oxygenated monoterpenes, were pulegone (22.5%), isomenthone (12.2%) and piperitenone (9.6%). The oil showed a slight antimicrobial activity against three bacterial strains.

Composition and allelopathic effect of essential oils of two thistles: Cirsium creticum (Lam.) D.�Urv. ssp. triumfetti (Lacaita) Werner and Carduus nutans L.

Abstract Cirsium and Carduus are two of the main genera of true thistles. Different species in these genera share a quantity of secondary metabolites and have interesting ecological properties. The essential oils of two species, Cirsium creticum and Carduus nutans, were analysed, showing the presence as main compounds of 4-ethyl guaiacol (15%), hexadecanoic acid (10.6%), (E)-β-damascenone (7.8%), dihydroactinidiolide (6.0%) and 4-vinyl guaiacol (4.5%) for C. creticum and hexadecanoic acid (18.6%), hexahydrofarnesylacetone (7.8%), heptacosane (5.9%), 4-vinyl guaiacol (5.8%), pentacosane (3.8%) and eugenol (3.6%) for C. nutans. The oils were evaluated at different doses for their effect on ge…

Chemical composition and antimicrobial activity of the essential oil from aerial parts of Micromeria fruticulosa (Bertol.) Grande (Lamiaceae) growing wild in Southern Italy

The essential oil of aerial parts of Micromeria fruticulosa (Lamiaceae) growing wild in Southern Italy was obtained by hydrodistillation and analysed by GC and GC–MS. Sixty-one compounds, representing 91.3% of the oil, were identified. The major components were γ-terpinene (14.5%), β-caryophyllene (12.6%), p-cymene (8.9%), α-pinene (8.2%) and β-bisabolene (7.2%). The essential oil showed action mainly against Gram-positive bacteria. Copyright © 2007 John Wiley & Sons, Ltd.

Chemical composition of the essential oils of Centaurea sicana and C. giardinae growing wild in Sicily

The essential oils of Centaurea sicana (S) and C. giardinae (G) were studied by GC and GC-MS. Thirty constituents for S, representing 81.5% of the total oil, and 24 compounds for G (94.2% of the total) were identified. The oils were rich in sesquiterpenoids (47.9% for S and 54.7% for G) and hydrocarbons (25.9% for S and 31.7% for G). Germacrene D (13.3%), ( E)-β-farnesene (8.3%), nonacosane (7.3%), heptacosane (6.5%) and phytol (6%) were recognized as the main constituents for S, while caryophyllene oxide (17.7%), nonacosane (14.5%), germacrene D (11.5%), caryophyllene (11.2%) and heptacosane (10.3%) were the main compounds for G.

Antiproliferative activity against leukemia cells of sesquiterpene lactones from the Turkish endemic plant Centaurea drabifolia subsp. detonsa

The apolar organic extract obtained from aerial parts of Centaurea drabifolia Sibth. & Sm. subsp. detonsa (Bornm.) Wagenitz, growing wild in Turkey, was investigated for the first time for its secondary metabolite composition. Seven sesquiterpene lactones belonging to the guaiane class (1-7), including the new compound 4, along with a fatty acid lactone derivative (8), were isolated. The structures of these compounds were established by spectroscopic analysis, including 2D NMR spectroscopic techniques, with the stereostructure of the new guaiane 4 determined with the help of MTPA derivatization. Cytotoxic activities of compounds 1-7 were evaluated against two cancer cell lines, namely acute…

Volatile constituents of aerial parts ofCentaurea sibthorpii(Sect. Carduiformes, Asteraceae) from Greece and their biological activity

The volatile constituents of the aerial parts of Centaurea sibthorpii [Sect. Carduiformes, Asteraceae] collected in Greece were extracted by hydrodistillation and analysed by GC and GC-MS. Altogether 63 components were identified. Fatty acids and sesquiterpenoidic compounds were the most abundant components in the oil. A study on the biological activity of the oil showed no action against Gram-positive and Gram-negative bacteria.

Volatile Components from Aerial parts of Centaurea gracilenta and C. ovina ssp. besserana Growing Wild in Bulgaria

The essential oils of Centaurea gracilenta Velen. (CG) and C. ovina Pall. ex Willd. ssp. besserana (DC.) Dostál (COB) growing wild in Bulgaria, were studied by GC and GC-MS. Forty-five compounds for CG, representing the 90.1% of the oil, and 68 compounds for COB, representing the 91.9% of the oil, were identified. The oils were rich in sesquiterpenoids (33.4% for CG and 27.3% for COB), hydrocarbons (28.3% for CG and 10.7% for COB) and carbonylic compounds (12.7% for CG and 13.1% for COB). Fatty acids were abundant only for COB (31.3%). β-Eudesmol (12.8%), nonacosane (11.8%) and p-vinyl guiacol (7.5%) were recognized as the main constituents for CG, while hexadecanoic acid (21.4%), spathule…

Phytochemical composition, anti-inflammatory and antitumour activities of four Teucrium essential oils from Greece

Abstract The essential oils of four Teucrium species were studied and 150 components, in all, were identified. All oils were rich in sesquiterpenes (50.1–55.8%). Spathulenol and δ-cadinene were the main compounds of Teucrium brevifolium oil; caryophyllene and 4-vinyl guaiacol predominated in Teucrium flavum . Carvacrol and caryophyllene oxide predominated in Teucrium montbretii ssp. heliotropiifolium , while carvacrol and caryophyllene were the most abundant components in Teucrium polium ssp. capitatum . The oil which most effectively inhibited LPS-induced NO production in macrophage cell line RAW 264.7 was that from T. brevifolium (IC 50  = 7.1 μg/ml), followed by T. montbretii ssp. heliot…

Anthemis wiedemanniana essential oil prevents LPS-induced production of NO in RAW 264.7 macrophages and exerts antiproliferative and antibacterial activities in vitro.

Anthemis wiedemanniana is known in folk medicine for the treatment of microbial infections, cancer and also urinary and pulmonary problems. In this study, the chemical composition of the essential oil from A. wiedemanniana was evaluated and its antibacterial activity was tested against 10 bacterial strains. The oil was also tested for its potentiality to inhibit nitric oxide production in RAW 264.7 macrophages and for its cytotoxicity against four human cancer cell lines. A. wiedemanniana oil, rich of oxygenated monoterpenes (25.4%), showed a good antibacterial activity against Gram-positive bacteria and a good activity against the two Gram-negative bacteria, Escherichia coli and Proteus vu…

Characterisation of the essential oil of Nepeta glomerata Montbret et Aucher ex Bentham from Lebanon and its biological activities.

The essential oil of Nepeta glomerata from Lebanon was studied by means of GC and GC/MS analysis; 70 compounds were identified. The oil was constituted mainly by monoterpenes and the most abundant components were α-pinene, spathulenol and carvacrol. Nepeta glomerata oil showed antibacterial activity, particularly towards Gram-positive bacteria, and also inhibited LPS-induced NO production in macrophage cell line RAW 264.7, with an IC(50) value of 78.1 µg mL(-1). Furthermore, an in vitro cytotoxic assay showed that the oil was more active on a renal adenocarcinoma cell line (48% of inhibition of proliferation at 100 µg mL(-1)) in comparison to an amelanotic melanoma.

Essential oil composition and antifeedant properties of Bellardia trixago (L.) All. (sin. Bartsia trixago L.) (Scrophulariaceae)

Attività antibatterica dei composti fenolici isolati da Marrubium globosum ssp. libanoticum

Volatile components from flower-heads of Centaurea nicaeensis All., C. parlatoris Helder and C. solstitialis L. ssp. schouwii (DC.) Dostál growing wild in southern Italy and their biological activity.

The volatile constituents of the flowerheads of Centaurea nicaeensis All., C. parlatoris Helder and C. solstitialis L. ssp. schouwii (DC.) Dostal were extracted by hydrodistillation and analysed by GC and GC-MS. Altogether 113 components were identified. Fatty acids and hydrocarbons were the most abundant components in the oils. Caryophyllene and caryophyllene oxide were the main compounds of the sesquiterpene fraction. The study on the biological activity of the oils shows no significant activity.

Comparison of essential oil components and in vitro anticancer activity in wild and cultivated Salvia verbenaca.

The objectives of our research were to study the chemical composition and the in vitro anticancer effect of the essential oil of Salvia verbenaca growing in natural sites in comparison with those of cultivated (Sc) plants. The oil from wild (Sw) S. verbenaca presented hexadecanoic acid (23.1%) as the main constituent, while the oil from Sc plants contained high quantities of hexahydrofarnesyl acetone (9.7%), scarce in the natural oil (0.7%). The growth-inhibitory and proapoptotic effects of the essential oils from Sw and Sc S. verbenaca were evaluated in the human melanoma cell line M14, testing cell vitality, cell membrane integrity, genomic DNA fragmentation and caspase-3 activity. Both t…

Volatile Components of Centaurea Bracteata and C. Pannonica subsp. Pannonica growing wild in Croatia

This paper reports on the volatile components of oils from the aerial parts (CBA) and roots (CBR) of Centaurea bracteata Scop. and aerial parts of C. pannonica (Heuffel) Simonkai subsp. pannonica (CPA), two Asteraceae growing wild in Croatia. The volatile components, obtained by hydrodistillation, were determined by GC-MS analysis. The yields (w/w) of the dried oils were 0.10% (CBA), 0.22% (CBR) and 0.09% (CPA), respectively. A total of 91 compounds were identified accounting for 91.1%, 93.3% and 87.9% of the total oil for CBA, CBR and CPA, respectively. All the samples were characterized mainly by hydrocarbons (7.1-34.1%), fatty acids (9.7-45.9%), and oxygenated sesquiterpenes (15.2-16.6%…

Volatile compounds of flowers and leaves of Sideritis italica (Miller)Greuter et Burdet (Lamiaceae), a plant used as mountain tea

Sideritis italica (Miller) Greuter et Burdet (Lamiaceae), widely used in ethnopharmacological medicine, occurs in Southern Italy and Sicily. The phytochemical composition of the essential oils of S. italica flowers and leaves, harvested in Piano Battaglia (Sicily), was analysed by GC and GC-MS. Of the 51 compounds, 43 in the oil from flowers and 29 in the oil from leaves were identified. Kaur-15-ene (20.0%) was recognised as the main constituent of the oil from flowers, together with beta-cubebene (12.1%), beta-pinene (8.5%), (Z)-nuciferol (6.5%), tricyclene (4.5%) and alpha-bisabolol (4.0%). In the oil from leaves, p-methoxyacetophenone (26.0%) prevailed, as did hexadecanoic acid (21.3%), …

Comparative chemical composition, free radical-scavenging and cytotoxic properties of essential oils of six Stachys species from different regions of the Mediterranean Area

Abstract The chemical composition of essential oils of six Stachys species, S. cretica L. ssp. vacillans Rech. fil., S. germanica L., S. hydrophila Boiss., S. nivea Labill., S. palustris L. and S. spinosa L., obtained by hydrodistillation, was studied by GC and GC–MS. All the oils have in common a great percentage of fatty acids and esters (24.2–58.5%) and a high amount of sesquiterpenes (16–35.9%), with the exception of the oil from S. palustris , which consisted mainly of carbonylic compounds (25.4%). The antioxidant activity by DPPH test and the antiproliferative activity on a series of human cancer cell lines (C32, amelanotic melanoma and ACHN, renal cell adenocarcinoma) were investigat…

Labdane Diterpenoids from Marrubium globosum ssp. libanoticum

From the aerial parts of Marrubium globosum ssp. libanoticum, seven labdane diterpenoids were isolated. Three of them are new natural products [(13R)-9alpha,13alpha-epoxylabda-6beta(19),16(15)-diol dilactone (2), deacetylvitexilactone (7), marrulanic acid (8)], whereas the other four, namely, (13S)-9alpha,13alpha-epoxylabda-6beta(19),16(15)-diol dilactone (1), cyllenin A (3), 15-epi-cyllenin A (4), and marrulibanoside, are previously known compounds. The structures of 2, 7, and 8 were determined by spectroscopic and chemical methods.

Furostanol saponins and ecdysones with cytotoxic activity from Helleborus bocconei ssp. intermedius

Two furostanol saponins helleboroside A (1) and helleboroside B (2) were isolated from the methanol extract of Helleborus bocconei Ten. subsp. intermedius (Guss.) Greuter and Burdet, along with the furospirostanol saponin 4 and two ecdysones: ecdysterone (5) and polypodyne B (6). Compound 2 was enzymatically hydrolysed to give product 3. The biological activity of all compounds was tested against rat C6 glioma cells showing a significant cytotoxicity for compounds 3, 4 and 6. Copyright © 2009 John Wiley & Sons, Ltd.

Chemical composition of the essential oil of Phagnalon saxatile (L.) Cass. (Asteraceae) growing wild in Southern Italy

Abstract The essential oil from aerial parts of Phagnalon saxatile (L.) Cass. (Asteraceae) was obtained by hydrodistillation. The oil content was 0.15% (v/w), on a dry weight basis. The oil composition was analyzed by GC and GC/MS. Altogether 66 compounds were identified accounting for 93.2% of the oil. Sesquiterpenes represent the 23.9% of the oil. In the oil were also present fatty acids (21.8%) and waxes (19.3%). The oil shows no antibacterial activity.

Chemical Composition and antimicrobial activity of the essential oils from two species of Thimus 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 essent…

Volatile constituents of aerial parts of three endemicCentaureaspecies from Turkey:Centaurea amanicolaHub.-Mor.,CentaureaconsanguineaDC. andCentaurea ptosimopappaHayek and their antibacterial activities

The volatile constituents of the aerial parts of Centaurea amanicola Hub.-Mor., Centaurea consanguinea DC. and Centaurea ptosimopappa Hayek were extracted by hydrodistillation and analysed by GC and GC–MS. Altogether 94 components were identified. Sesquiterpenoids, fatty acids and carbonylic compounds were the most abundant components in the oils. Hexadecanoic acid and (Z,Z )-9,12-octadecadienoic acid were the main fatty acids in all the examined samples, that showed different patterns of composition. The study on the biological activity of the oils showed an action mainly against the Gram-positive pathogens.

A new irregular diterpenoid of biogenetic interest from the flowers of Magydaris tomentosa (Desf.) DC. (Apiaceae)

A new irregular acyclic diterpene, magytomol acetate (2), has been isolated from the light petroleum extract of the flowers of Magydaris tomentosa (Desf.) DC. (Apiaceae) and its structure has been elucidated by means of extensive spectroscopic experiments. The new compound can be considered the acetyl derivative of the biogenetic precursor of other irregular diterpenes isolated from other species belonging to the family Apiaceae.

Cytotoxic properties of Marrubium globosum ssp. libanoticum and its bioactive components

Marrubium globosum Montbr. et Auch. ex Benth. ssp. libanoticum Boiss. (Lamiaceae) is a medicinal plant used in Lebanon for the treatment of inflammatory diseases, asthma, coughs and other pulmonary and urinary problems. The goal of our study was to assess the biological activity of M. globosum by testing different extracts of the aerial parts for their antiproliferative activity against human melanoma cells using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The chloroform fraction showed the greatest activity. The compounds isolated from the extracts were also tested: the mixture of (13 S)-9α,13α-epoxylabda-6β(19),16(15)-diol dilactone and (13 R)-9α,13α-epo…

Essential oils of Salvia bracteata and Salvia rubifolia from Lebanon: Chemical composition, antimicrobial activity and inhibitory effect on human melanoma cells

Aim of the study: Salvia bracteata Banks et Sol. and Salvia rubifolia Boiss. are known in folk medicine of Lebanon for the treatment of microbial infections, cancer, urinary and pulmonary problems. In the present study the chemical composition and antimicrobial activity of essential oils from aerial parts of Salvia bracteata and Salvia rubifolia collected in Lebanon were evaluated. The oils were also tested for their potential antiproliferative effects against M14 human melanoma cells. Material and methods: The oils were studied by GC and GC-MS and their antibacterial activity (MIC and MBC) was tested against ten bacteria species using the broth dilution method. The inhibitory effect on hum…

Composition of the essenthial oil of Petagnaea gussonei (Sprengel) Rauschert, a relict species from Sicily (Southern Italy).

The essential oil from leaves, stems and roots of Petagnaea gussonei (Sprengel) Rauschert ( = Petagnia saniculifolia Guss.), endemic to the Nebrodi Mountains (Sicily, Italy), has been analysed by the gas chromatography–mass spectrometry (GC–MS) system on two fused-silica capillary columns of different polarities. A total of 94 components were identified. Quantitative and qualitative differences were found among the analysed parts. The principal compounds from the leaves oil were found to be (w/w%) germacrene D (19.9%), γ-muurolene (7.96%) and caryophyllene oxide (6.85%), while in the oil from stems hexadecanoic acid (23.40%), germacrene D (18.50%) and (Z,Z)-9,12-octadecadienoic acid (13.20%…

Inhibitory effects of cynaropicrin on human melanoma progression by targeting MAPK, NF-κB, and Nrf-2 signaling pathways in vitro

Malignant melanoma is the deadliest skin cancer, due to its propensity to metastasize. MAPKs and NF-κB pathways are constitutively activated in melanoma and promote cell proliferation, cell invasion, metastasis formation, and resistance to therapeutic regimens. Thus, they represent potential targets for melanoma prevention and treatment. Phytochemicals are gaining considerable attention for the management of melanoma because of their several cellular and molecular targets. A screening of a small library of sesquiterpenes lactones selected cynaropicrin, isolated from the aerial parts of Centaurea drabifolia subsp. detonsa, for its potential anticancer effect against melanoma cells. Treatment…

Volatile constituents of Scutellaria rubicunda Hornem subsp. linnaeana (Caruel) Rech. (Lamiaceae) endemic in Sicily

Essential oil composition of the fruits of Periploca laevigata Aiton subsp. angustifolia (Labill.) Markgraf (Apocynaceae – Periplocoideae)

The essential oil of the fruits of Periploca laevigata Aiton subsp. angustifolia (Labill.) Markgraf (Apocynaceae) from Lampedusa Island was obtained by hydrodistillation and its composition was analysed. The analyses allowed the identification and quantification of 64 volatile compounds belonging to different classes. The most abundant compounds were nonacosane, heptacosane, hentriacontane and δ-cadinene. Among the volatile compounds identified in the fruits of P. laevigata subsp. angustifolia, 31 are present in other taxa of Apocynaceae, 19 have antimicrobial activity and four are pheromones for the butterfly Danaus chrysippus. The possible ecological role of the volatile compounds found i…

Volatile constituents of Stachys palaestina L. (Palestine woundwort) growing in Lebanon

The hydrodistillation of the aerial parts of Stachys palaestina L. collected in Lebanon in the Kadisha Valley, yielded 0.1% (w/w) of essential oil. GC and GC-MS analyses enabled the identification of 87 compounds representing 90.8% of the total oil. Hexadecanoic acid (10%), hexahydrofarnesyl acetone (6.9%), eugenol (4.3%) and (E)-caryophyllene (4.3%) were the main components. On the whole, the oil was constituted mainly of sesquiterpenes (37.7%), among which sesquiterpene hydrocarbons (20.7%) slightly prevailed over oxygenated sesquiterpenes (17.0%). This is the first report on the chemical composition of S. palaestina essential oil.

Volatile constituents of aerial parts of two Mediterranean species of Inula: Inula crithmoides L. and I. verbascifolia (Willd.) Hausskn. (Asteraceae)

Inula crithmoides L. grows along the Mediterranean coasts and is used as an edible vegetable as the young leaves or shoots are eaten raw, cooked or pickled. Inula verbascifolia (Willd.) Hausskn. is a quite localised species growing mainly along the Adriatic Sea coasts. In this study the volatile components of the aerial part of both species are described. Gas chromatography and gas chromatography mass spectrometry analysis showed the presence of 41 components in I. crithmoides and 75 compounds in I. verbascifolia, respectively, and a very different profile in the composition of the two species. The chemotaxonomy of I. crithmoides, by comparison with other data reported in the literature, is…

Essential Oil Composition of Tanacetum vulgare Subsp. Siculum (Guss.) Raimondo et Spadaro (Asteraceae) from Sicily

Ninety-four components of the essential oils from aerial parts and capitula of Tanacetum vulgare subsp. siculum (Guss.) Raimondo et Spadaro were detected. α-Thujone, β-thujone and 1,8-cineole were the main constituents of the oils. The analysis allows the assignment of this Tanacetum species to the thujone chemotype.

Analysis of Essential Oils from Scutellaria orientalis ssp. alpina and S. utriculata by GC and GC-MS

The chemical composition of the essential oils obtained from aerial parts of Scutellaria orientalis L. ssp. alpina (Boiss.) O. Schwarz and S. utriculata Labill. growing wild in Lebanon, were analyzed by GC and GC-MS. In S. orientalis ssp. alpina, strongly characterized by sesquiterpenes (41.2%) and particularly sesquiterpene hydrocarbons (31.7%), hexahydrofarnesylacetone (11.7%) was recognized as the main constituent, together with hexadecanoic acid (7.6%), caryophyllene (7.4%), caryophyllene oxide (6.8%), 4-vinylguaiacol (5.4%) and germacrene D (5.4%). S. utriculata oil was instead constituted above all by monoterpenes (42.2%), particularly oxygen containing monoterpenes (39.9%), and in t…

Chemical composition of the essential oil of Jacobaea maritima (L.) PelserMeijden and Jacobaea maritima subsp. bicolor (Willd.) B. Nord.Greuter (Asteraceae) collected wild in Croatia and Sicily, respectively.

In this study, the chemical compositions of the essential oils from aerial parts (JmA) and radices (JmR) of Jacobaea maritima (L.) Pelser & Meijden, collected in Croatia, and of Jacobaea maritima subsp. bicolor (Willd.) B. Nord. & Greuter, collected in Sicily, were evaluated by using gas chromatography and gas chromatography–mass spectrometry. The main components of the essential oil from J. maritima, both in JmA and JmR, were pentacosane (15.7%), heptacosane (13.1%) and nonacosane (8.1%) whereas the essential oil from J. maritima subsp. bicolor was characterised by the presence of hexadecanoic acid (14.6%), caryophyllene oxide (9.3%) and hexahydrofarnesylacetone (6.5%). The comparison of t…

Flavonoids in Subtribe Centaureinae (Cass.) Dumort. (Tribe Cardueae, Asteraceae): Distribution and 13C-NMR Spectral Data

Abstract 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.

Effect of Marrubium globosum ssp libanoticum on intestinal motility

New diterpenes from Marrubium globosum Montbr. et Auch. ex Benth. ssp. libanoticum Boiss. (Lamiaceae)

Chemical composition and anticancer activity of essential oils of Mediterranean sage (Salvia officinalis L.) grown in different environmental conditions

Salvia officinalis L. can be found worldwide and its leaves are commonly used as ingredient in food industry. Sage essential oil is applied in the treatment of a range of diseases and has been shown to possess different biological activities. The objectives of our research were to study the effects of environment on crop, chemical composition and anticancer activity on S. officinalis essential oil. Sage was cultivated at eighteen experimental sites in south-central Italy (Molise) in different growing environments. The essential oils (S1-S18), extracted by hydrodistillation, were analyzed by GC and CG/MS. Results show that the main components were α-thujone, camphor, borneol, γ-muurolene and…

Phenolic compounds of Marrubium globosum ssp.libanoticum from Lebanon

Phytotoxic effects of essential oils of Nepeta curviflora Boiss and Nepeta nuda L.subsp. albiflora growing wild in Lebanon

The chemical composition of the essential oils of two Nepeta species collected in Lebanon was studied by means of GC and GC-MS analysis. The essential oil from N. curviflora Boiss. contained high amounts of β-caryophyllene (41.6%), caryophyllene oxide (9.5%), (E)-β-farnesene (6.2%) and (Z)-β-farnesene (4.8%); in the oil from N. nuda L. subsp. albiflora (Boiss.) Gams. collected in Laklouk the main compounds were β-bisabolene (11.8%), pulegone (10.8%), (E,Z)-nepetalactone (8.0%), (E)-β-farnesene (7.1%) and caryophyllene oxide (6.9%), while N. nuda L. subsp. albiflora collected in Tannourine Cedar Forest contained high percentages of hexadecanoic acid (10.1%), β-bisabolene (7.8%), caryophyllen…

Chemical Composition and Antibacterial Activity of Extracts of Helleborus bocconei Ten. subsp. intermedius

Helleborus bocconei Ten. subsp. intermedius (Ranunculaceae) is a Sicilian medicinal plant used for the treatment of pneumonia affecting cows and horses and for the removal of human decayed molars. The goal of our study was to assess the biological activity of Helleborus bocconei subsp. intermedius by testing its extracts for their activity against bacteria known to cause respiratory diseases. The two more active extracts (light petroleum from roots and aerial parts), as well as the dichloromethane extracts, were analyzed by GC/MS and their composition is reported.

GC and GC-–MS Analysis of Volatile Compounds From Ballota nigra subsp. uncinata Collected in Aeolian Islands, Sicily (Southern Italy)

In the present study, the chemical composition of the essential oils from aerial parts of Ballota nigra subsp. uncinata (Bég.) Patzak collected in Sicily was evaluated by gas chromatography (GC) and GC-mass spectrometry. The main components of the oil were ( E)-phytol (20.0%), α-pinene (9.0%), hexahydrofarnesyl acetone (5.7%), and α-selinene (5.1%). Cluster analysis of the essential oil compositions of all the taxa belonging to B. nigra s.l. group was performed.

Phytochemical profile of three Ballota species essential oils and evaluation of the effects on human cancer cells

Three Ballota species, Ballota undulata, Ballota saxatilis and Ballota nigra ssp. foetida, were investigated for their cytotoxicity against two human cancer cells, hepatoma HepG2 cell line and breast cancer MCF-7 cell line, and for their antioxidant activity. The chemical composition of essential oils was studied by GC and GC–MS. Sesquiterpenes were the main constituents. The most antiproliferative essential oil against HepG2 cells was B. undulata with a percentage of inhibition of 81.36 ± 3.54 at a concentration of 100 μg/mL, while against MCF-7 cells essential oil from B. saxatilis was the most active with a percentage of inhibition of 24.18 ± 1.13 at a concentration of 100 μg/mL. The ant…

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 t…

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.

Volatile constituents of aerial parts of Lasiopogon muscoides

Effects of solvent-free microwave extraction on the chemical composition of essential oil of Calamintha nepeta (L.) Savi compared with the conventional production method

The essential oil of Calamintha nepeta has been obtained by solvent-free microwave extraction (SFME) and by classical hydrodistillation (HD). A comparative qualitative-quantitative study on the composition of the oils was carried out. A total of 38 compounds, constituting 97.6% of the oil, were identified in the oil obtained by SFME, whereas 46 compounds, representing 95.4% of the oil, were characterized in the HD oil. SFME-distilled oil is richer in lightly oxygenated monoterpenes (LOM) than HD oil. It also has a higher amount of sesquiterpenes and a lower quantity of hydrocarbon monoterpenes. HD oil seems to be affected by chemical changes more than SFME oil.

Two New Flavonoids fromBonannia graeca: a DFT-NMR Combined Approach in Solving Structures

Two new cyclized C-geranylated flavonoids, the dihydroflavonol bonanniol C (4a) and the flavanone bonannione B (6a), were isolated as minor compounds from the aerial parts of Bonannia graeca (Umbelliferae). Their structures were elucidated by a combined approach of extensive spectroscopic means and quantum mechanical methods. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

Volatile constituents of the aerial parts of white salsify (Tragopogon porrifolius L., Asteraceae).

Tragopogon porrifolius L. grows as a vegetable in southern Italy and all parts of it are edible. In the present study the volatile components of the aerial part are described. Gas chromatography and gas chromatography-mass spectrometry analysis showed the presence of 38 components in all. On the whole, the volatile fraction was constituted mainly by carbonylic compounds (24.6%), phenols (21.5%) and fatty acids and esters (19.7%). The most abundant compounds were 4-vinyl guaiacol (19.0%), hexadecanoic acid (17.9%), hexahydrofarnesylacetone (15.8%) and hentriacontane (10.7%).

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.

Essential oils of three species of scutellaria and their influence on Spodoptera littoralis

Chemical composition of the essential oils of Centaurea formanekii and C. orphanidea ssp. thessala, growing wild in Greece.

The volatile constituents of the aerial parts of Centaurea formanekii Halacsy and the aerial parts, capitula and roots of C. orphanidea Heldr. & Sart. ex Boiss. ssp. thessala (Hausskn.) Dostál from Greece were extracted by hydrodistillation and analyzed. The main components in C. formanekii were hexadecanoic acid (13.6%), δ-elemene (9.1%), and spathulenol (6.9%). The main components in C. orphanidea ssp. thessala were γ-elemene (26.1%) and caryophyllene oxide (13.2%) in the aerial parts, hexadecanoic acid (33.5%) and heptacosane (6.3%) in the capitula, and hexadecanoic acid methyl ester (22.0%) and α-chamigrene (14.0%) in the roots. The chemotaxonomic significance with respect to other…

Chemical composition of the essential oil of Salvia microstegia Boiss. et Balansa growing wild in Lebanon.

The essential oil of aerial parts of Salvia microstegia Boiss. et Balansa (Lamiaceae) growing wild in Lebanon was obtained by hydrodistillation and was analysed by GC and GC–MS. 70 compounds, representing 94.0% of the oil, were identified. The major components were caryophyllene oxide (6.2%), pulegone (5.7%), 4-vinylguaiacole (5.3%), hexadecanoic acid (5.1%) and menthone (4.9%). © 2006 Elsevier B.V. All rights reserved.

GC and GC/MS analysis of the essential oil of Salvia hierosolymitana boiss. Growing wild in Lebanon

The essential oil of the aerial parts of Salvia hierosolymitana Boiss. (Lamiaceae), growing wild in Lebanon, was obtained by hydrodistillation and analysed by GC and GC-MS. Ninety-two compounds, representing 92.7% of the oil, were identified. The major components were hexadecanoic acid (15.5%), phytol (5.4%), hexahydrofarnesyl acetone (4.6%), (Z,Z)-9,12-octadecadienoic acid (4.5%) and 4-vinylguaiacol (4.4%).

Chemical composition and biological activity of Salvia verbenaca essential oil

Salvia verbenaca L. (syn. S. minore) is a perennial herb known in the traditional medicine of Sicily as “spaccapetri” and is used to resolve cases of kidney stones, chewing the fresh leaves or in decoction. The chemical composition of the essential oil obtained from aerial parts of S. verbenaca collected in Piano Battaglia (Sicily) on July 2009, was analyzed by GC and GC-MS. The oil was strongly characterized by fatty acids (39.5%) and carbonylic compounds (21.2%), with hexadecanoic acid (23.1%), ( Z)-9-octadecenoic acid (11.1%) and benzaldehyde (7.3%) as the main constituents. The in vitro activity of the essential oil against some microorganisms in comparison with chloramphenicol by the …

Volatile constituents of aerial parts of three endemic Centaurea species from Turkey: Centaurea amanicola Hub.-Mor., Centaurea consanguinea DC. and Centaurea ptosimopappa Hayek and their antibacterial activities.

The volatile constituents of the aerial parts of Centaurea amanicola Hub.-Mor., Centaurea consanguinea DC. and Centaurea ptosimopappa Hayek were extracted by hydrodistillation and analysed by GC and GC-MS. Altogether 94 components were identified. Sesquiterpenoids, fatty acids and carbonylic compounds were the most abundant components in the oils. Hexadecanoic acid and (Z,Z )-9,12-octadecadienoic acid were the main fatty acids in all the examined samples, that showed different patterns of composition. The study on the biological activity of the oils showed an action mainly against the Gram-positive pathogens.

Analysis of Essential Oil from Teucrium maghrebinum Greuter et Burdet Growing Wild in Algeria

The chemical composition of the essential oil obtained from aerial parts of Teucrium maghrebinum growing wild in Algeria was analyzed by GC and GC-MS. Among the 66 identified compounds, δ-cadinene (12.7%), germacrene D (11.4%), γ-cadinene (9.5%) and 4-vinyl guaiacol (4.0%) were the most abundant. The oil is strongly characterized by the presence of sesquiterpenes (61.5%), particularly hydrocarbon sesquiterpenes (49.6%).

Chemical composition and antimicrobial activity of the essential oil ofPhlomis ferruginea Ten. (Lamiaceae) growing wild in Southern Italy

The essential oil of aerial parts of Phlomis ferruginea (Lamiaceae), growing wild in Southern Italy, was obtained by hydrodistillation and analysed by GC and GC–MS. 60 compounds, representing 92.3% of the oil, were identified. The major components were β-caryophyllene (15.6%), hexadecanoic acid (12.8%), germacrene D (8.9%), caryophyllene oxide (6.7%) and α-thujone (5.5%). The evaluation of antimicrobial activity against some bacterial species has been tested. Copyright © 2006 John Wiley & Sons, Ltd.

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 microorganism…

Essential Oil Composition and Antibacterial Activity of Anthemis mixta and A. Tomentosa(Asteraceae)

In the present study the chemical composition of the essential oils from aerial parts and roots of Anthemis mixta L. and A. tomentosa L. was evaluated by GC and GC-MS, and their antibacterial activity tested against ten bacterial species. Hexadecanoic acid (15.2%) was recognized as the main constituent of A. mixta, together with τ-cadinol (6.7%), while in both aerial parts and roots of A. tomentosa nonacosane (21.9% and 20.7%), heptacosane (8.1% and 6.0%), hexadecanoic acid (8.1% and 27.1%) and hexahydrofarnesylacetone (6.8% and 5.5%) prevailed. The oils from aerial parts of both species showed a good activity against Gram-positive bacteria. These results suggest that the plants could be p…

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 a…

Constituents of leaves and flowers essential oils of Helichrysum pallasii (Spreng.) Ledeb. growing wild in Lebanon.

The chemical compositions of the essential oils obtained from leaves and flowers of Helichrysum pallasii were analyzed by gas chromatography and gas chromatography-mass spectrometry. Among the 102 identified constituents, hexadecanoic acid (16.2%), (Z,Z)-9,12-octadecadienoic acid (6.8%), tetradecanoic acid (2.6%), and (Z)-caryophyllene (4.2%) were the main constituent of the oil from leaves, while in the oil from flowers hexadecanoic acid (14.7%), (Z,Z)-9,12-octadecadienoic acid (14.2%), (Z)-caryophyllene (3.6%), and delta-cadinene (3.1%) predominated. The oils were both characterized by sesquiterpenes (33.4% for leaves and 33.7% for flowers, respectively) and fatty acids and esters (30.3% …

Headspace Volatile Composition of the Flowers of Caralluma europaea N.E.Br. (Apocynaceae)

The volatile constituents of the flowers of Caralluma (Apteranthes) europaea (Guss.) N.E. Br. (Apocynaceae - Asclepiadoideae) from Lampedusa Island were analyzed by headspace method. The analyses allowed the identification and quantification of 41 compounds. The main components were, among the monoterpenoids, terpinolene (23.3%), a-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%). It is worth to mention the presence of a nitrogen containing compound, indole (0.8%) and of a sulphur containing compound, dimethylsulphide (t). The compounds found in the flowers of C. europea…

Chemical Composition of the Essential Oils of Three Species of Apiaceae Growing Wild in Sicily: Bonannia graeca, Eryngium maritimum and Opopanax chironium

In the present study the chemical composition of the essential oils from aerial parts of Bonannia graeca (L.) Halácsy and Opopanax chironium (L.) Kock, and from aerial parts and roots of Eryngium maritimum L. was evaluated by GC and GC-MS. α-Pinene (15.2%) and β-pinene were recognized as the main constituents of B. graeca, whereas the aerial parts of O. chironium contained mainly the diterpene cembrene and the coumarin angelicin. In both aerial parts and roots of E. maritimum germacrene D (10.4% and 15.9%, respectively) and 2,4,5-trimethylbenzaldehyde (8.3% and 6.7%) were the most abundant components.

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…

Essential oil from the aerial parts of Centaurea cuneifolia Sibth. & Sm. and C. euxina Velen., two species growing wild in Bulgaria

Abstract The volatile constituents of the aerial parts of Centaurea cuneifolia Sibth. & Sm. and Centaurea euxina Velen. from Bulgaria were extracted by hydrodistillation and were analyzed. The main components in C. cuneifolia were β-eudesmol (26.5%) and hexadecanoic acid (17.6%). The main components in C. euxina were hexadecanoic acid (20.3%), spathulenol (10.8%) and caryophyllene oxide (6.2%). The chemotaxonomic significances with respect to other previously studied species of the same sections ( Achrolopus and Phalolepis , respectively) are discussed.

Antibacterial activity of flavonoids and phenylpropanoids from Marrubium globosum ssp. libanoticum.

Marrubium globosum Montbr. et Auch. ex Benth. ssp. libanoticum Boiss. (Lamiaceae) is a medicinal plant used for the treatment of inflammatory diseases, asthma, coughs and other pulmonary and urinary problems. The goal of our study was to assess the biological activity of M. globosum testing the methanol extract of aerial parts for its antibacterial activity against bacteria known to cause respiratory, gastrointestinal, skin and urinary disorders; the extract showed antibacterial effects against all the strains of bacteria used. A purification of this active extract showed the presence, as main constituents, of verbascoside, isorhamnetin 3-O-beta-D-rutinoside, quercetin 3-O-beta-D-rutinoside…

Volatile components of aerial parts of Centaurea nigrescens an C. stenolepis growing wild in the Balkans

The volatile constituents of the aerial parts of Centaurea nigrescens Willd, collected in Romania and of two samples of C. stenolepis A. Kerner from Bulgaria and Romania were obtained by hydrodistillation and analyzed. The main components of C. stenolepis were caryophyllene oxide (6.9-15.6%), hexahydrofarnesyl acetone (6.5-4.4%), heptacosane (6.0-4.9%) and p-vinyl guiacol (4.3-5.0%). The main components of C. nigrescens were caryophyllene oxide (9.9%), β-eudesmol (9.5%), spathulenol (7.6%), heptacosane (6.1%) and p-vinyl guiacol (5.5%). The chemotaxonomic significance with respect to their co-location in Sections Lepteranthus and Nigrescentes, respectively, is discussed.

GC and GC–MS analysis of the essential oil of Nepeta cilicica Boiss. ex Benth. from Lebanon

The hydrodistillation of the aerial parts of Nepeta cilicica Boiss. ex Benth., collected in Lebanon in the Horsh Ehden reserve, yielded 0.13% (w/w) of essential oil. Gas chromatography (GC) and GC-mass spectroscopy analysis enabled the identification of 75 compounds representing 96.8% of the total oil. The most abundant compounds were spathulenol (15.1%), hexadecanoic acid (14%), δ-cadinene (5.5%) and α-copaene (4.5%). On the whole, the oil was constituted mainly by sesquiterpenes (45.9%), among which sesquiterpene hydrocarbons (27.6%) slightly prevailed over oxygenated sesquiterpenes (18.3%).

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 …

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 …

Effect of Germacrene-Rich Essential Oil of Parentucellia latifolia (L.) Caruel Collected in Central Sicily on the Growth of Microorganisms Inhabiting Historical Textiles

In the present study, the chemical composition of the essential oil from aerial parts of Parentucellia latifolia (L.) Caruel collected in Central Sicily was analyzed by gas chromatography and gas chromatography–mass spectrometry. The results showed the presence of sesquiterpene hydrocarbons, with germacrene D and germacrene B accounting, respectively, for 59.2% and 24.3% of the total oil. Different colonies of bacteria and fungi frequently affect cellulosic objects such as books stored in libraries and museums. The antibacterial and antifungal activity against some microorganisms infesting historical-artistic craftsmanship was determined, demonstrating that the essential oil was particular…

Antibacterial and anticoagulant activities of coumarins isolated from the flowers of Magydaris tomentosa.

The phytochemical investigation of the acetone and methanol extracts of the flowers of Magydaris tomentosa (Desf.) DC afforded six known coumarins as well as (+)-meranzin hydrate (7), not previously reported as a natural product. The antibacterial activity of umbelliprenin (1), osthol (2), imperatorin (3), citropten (4) and (+)-meranzin hydrate (7) was tested against Gram-positive and Gram-negative bacteria. All coumarins (1-7) isolated in this study inhibited growth of all bacterial strains tested (MIC between 16 and 256 microg/mL), the most active being imperatorin (3) (MICs between 32 and 128 microg/mL) and citropten (4) (MICs between 16 and 256 microg/mL). The anticoagulant activity of …

Cytotoxic activity of diterpenoids isolated from the aerial parts of Elaeoselinum asclepium subsp. meoides.

The phytochemical investigation of the acetone extract of the aerial parts of Elaeoselinum asclepium (L.) Bertol. subsp. meoides (Desf.) Fiori afforded several known diterpenoids as well as meoidic acid ( 5), new in the literature. The cytotoxic activities of elasclepic acid ( 1), ENT-atis-16-en-19-oic acid ( 2), ent-beyer-15-en-19-oic acid ( 3), ent-kaur-16-en-19-oic acid ( 4) and meoidic acid ( 5) were investigated on rat glioma C6 cells by evaluation of cell growth inhibition.