The Diterpenoids of the Genus Marrubium (Lamiaceae)

The occurrence and chemical structures of labdane diterpenoids from the genus Marrubium are reviewed and the published 13C NMR spectroscopic data for these compounds is presented. The pharmacological activities and biogenesis of these diterpenoids are also reported.

Lipase-catalysed preparation of acyl derivatives of the germacranolide cnicin

Several acyl derivatives of cnicin were obtained through lipase-catalysed acylation and alcoholysis reactions. In most reactions lipases showed a regioselective behaviour affording only one product. Longer chain acyl derivatives were prepared at lower temperature than the used in lipase-catalysed reactions, to preclude side products formation. The enzymatic approach let to prepare a family of novel acetyl and fatty acid derivatives of cnicin which are not obtainable following traditional organic synthetic procedures. Fil: Monsalve, Leandro Nicolas. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis…

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.

Essential oil compositions of Teucrium fruticans, T. scordium subsp. scordioides and T. siculum growing in Sicily and Malta

In the present study, the chemical composition of the essential oils from the aerial parts of Teucrium fruticans L. collected in Sicily and Malta, Teucrium scordium subsp. scordioides (Schreb.) Arcang. and Teucrium siculum (Raf.) Guss., collected in Sicily, were evaluated by GC-MS. The main volatile components of both T. fruticans collections were germacrene D (29.4% and 50.0%), (E)-β-caryophyllene (19.6% and 21.9%), and 1-octen-3-ol (19.7% and 7.4%); T. scordium subsp. scordioides essential oil was rich in caryophyllene oxide (25.8%), α-pinene (19.4%) and β-pinene (8.5%); T. siculum essential oil was rich in (E)-β-caryophyllene (30.9%), 1-octen-3-ol (9.0%), α-humulene (8.6%) and germacrene…

Floral scent in Iris planifolia (Iridaceae) suggests food reward

Iris species can adopt different pollination strategies to attract their pollinators, generalized shelter-mimicking, specialized deceptive sexual-mimicking or food-rewarding. As attractive stimuli, Iris flowers may use their colours, large-size, symmetry, and volatile organic compounds (VOCs). However, relatively few studies in- vestigated Iris floral olfactory cues in the context of plant-visitor/pollinator interactions. In the present study we combined the identification of the floral volatiles of the nectariferous I. planifolia with insects visiting its flowers to gather data on its biology. Floral volatiles were collected in the natural environment by dynamic headspace and analysed by g…

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.

Sesquiterpene lactones of Anthemis alpestris

Photoinduced functionalization of diterpenes: transformation of the C-20 methyl of atractyligenin into a carbomethoxymethyl or carbamoylmethyl group

Abstract Irradiation of the nor-diterpene atractyligenin 1a and of its methyl ester 1b at λ=254 nm in methanol or in methanol in the presence of nitrogen nucleophiles such as ammonia or methylamine gave, besides the decarboxylation product 2, the ester 3a or the amides 3b, 3c, respectively, providing the transformation of the C-20 angular methyl into a carbomethoxymethyl or carbamoylmethyl group. A photochemical pathway involves formation of C-19/C-20 bond in the excited state, followed by a collapse into a ketene intermediate which will capture the nucleophilic reagent.

Anti-HIV Agents Derived from the ent-Kaurane Diterpenoid Linearol

Twenty-six semisynthetic ent-kaurane derivatives of linearol (1) have been investigated for their anti-HIV effects. Five compounds (4, 7, 11, 25, and 26) showed significant activity against HIV replication in H9 lymphocyte cells with EC(50) values in the range <0.1-3.11 microg/mL. With TI values of 163 and 184, compounds 4 and 25 are especially promising for further development as potential anti-HIV agents.

Advances on the chemistry of furano-diterpenoids from Teucrium genus

This paper updates the previous reviews, reporting the results published in the last six years on the chemistry of these diterpenoids.

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…

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

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

Assigning the C-15 configuration of 15-hydroxy-, 15-methoxy-, 15-ethoxy- hexahydrofurofuran neoclerodane diterpenoids

The Essential Oil Compositions of Three Teucrium Taxa Growing Wild in Sicily: HCA and PCA Analyses

The chemical composition and the qualitative and quantitative variability of the essential oils of three taxa belonging to the Teucrium genus were studied. The investigated taxa, that grow wild in Sicily, were Teucrium flavum L. (section Chamaedrys (Mill.) Scheb.), Teucrium montanum and Teucrium capitatum L. of section Polium (Mill.) Scheb. Essential oils were extracted by hydrodistillation and analyzed by GC-MS. In total, 74 compounds were identified. Sesquiterpene hydrocarbons were found to be the main group for T. flavum (48.3%). T. capitatum consisted essentially of monoterpene hydrocarbons (72.7%), with &alpha

INDAGINE FITOCHIMICA SUGLI OLI DEI SEMI DI PTILOSTEMON GREUTERI (ASTERACEAE)

Guaianolides from the Aerial Parts of Centaurea Hololeuca

Seven guaianolides were isolated from the acetone extract of the aerial parts of Centaurea hololeuca Boiss. The antifeedant activity of the natural compounds (1–7) and of four chloro derivatives (8–11), synthesized from repin (1) and janerin (3) were tested against larvae of Spodoptera littoralis. Cebellin J (6) and chlorojanerin (11) showed significant antifeedant activity at 100 ppm, whereas at this concentration cebellin G (4) and 15-deschloro-15-hydroxychlorojanerin (7) stimulated feeding. Cebellin G (4) stimulated larvae of S. littoralis to feed at low concentration, but deterred feeding at high concentrations. The addition of chlorine to repin (1) resulted in an increase in antifeeda…

The Diterpenoids of the Genus Elaeoselinum (Apiaceae) and their Biological Properties

The natural kaurane, beyerane and atisane diterpenoids isolated from the genus Elaeoselinum (Apiaceae)and their semi-synthetic derivatives are reviewed. Published 13C NMR spectroscopic data and biological properties of these diterpenes are also reported.

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…

Acid-induced rearrangement of epoxygermacra-8,12-olides: synthesis and absolute configuration of guaiane and eudesmane derivatives from artemisiifolin

A study on the acid-induced rearrangement of 4,5-epoxy- and 1,10-epoxygermacra-8,12-olides was carried out. From a 4,5-epoxy derivative, guaianes were obtained, whereas 1,10-epoxy derivatives furnished, depending on the stereochemistry of the C-1/C-10 epoxy ring, trans-5β,10α- or trans-5α,10β-eudesmanolides.

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

Antibacterial and Antifungal Activities of Acetonic Extract from Paullinia cupana Mart Seeds

The antibacterial and antifungal activities of the acetone extract from Paullinia cupana var. sorbilis Mart. (Sapindaceae) seeds, commonly called guarana, were assessed against selected bacterial and fungal strains. We tested the extract against both standard American Type Culture Collection (ATCC) and clinically isolated (CI) bacterial strains and three fungal strains. Minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values for bacteria and MIC and minimum fungicidal concentration for fungi were determined. The extract showed an activity against the nine bacterial strains tested, both CI and ATCC strains (MIC comprised between 32 and 128 μm/mL and MBC bet…

Lipase-catalysed preparation of acyl derivatives of the germacranolide sesquiterpenoid cnicin

Several acyl derivatives of cnicin were obtained through lipase-catalysed acylation and alcoholysis reactions. In most reactions lipases showed a regioselective behaviour affording only one product. Longer chain acyl derivatives were prepared at lower temperature than the used in lipase-catalysed reactions, to preclude side products formation. The enzymatic approach let to prepare a family of novel acetyl and fatty acid derivatives of cnicin which are not obtainable following traditional organic synthetic procedures.

Chemical Composition and Antimicrobial Activity of the Essential Oil from Flowers of Eryngium triquetrum (Apiaceae) Collected Wild in Sicily

The chemical composition of the essential oil from flowers of Eringium triquetrum Vahl. collected in Sicily was evaluated by GC and GC-MS. The main components were pulegone (50.6%), piperitenone (30.5%) and menthone (7.0%). Comparison of this oil with other studied oils of Eringium species is discussed. The oil showed good antibacterial and antifungal activities against some microorganisms that infest historical art works.

Phytochemical analysis ofAchillea ligusticaAll. from Lipari Island (Aeolian Islands)

A complete chemical investigation of Achillea ligustica All. growing at Lipari (Aeolian Island, Sicily) has been carried out. Seventeen metabolites have been isolated and characterised from dichloromethane and methanol extracts of flowers and aerial parts, and GC/MS analyses of petroleum ether extracts was carried out, revealing a composition in sesquiterpenoids similar to those reported for populations from Greece, Sicily and Algeria, showing the presence of (3RS,6RS)-2,6-dimethyl-1,7-octadiene-3,6-diol (1), 2,6-dimethyl-octa-3(E),7-diene-2,6-diol (2), iso-seco-tanapartholide (3) from DCM fraction. In addition from the methanolic extract of the aerial parts, peculiar flavonoid glucuronides…

Indagini fitochimiche su alcune popolazioni italiane di Artemisia alba (Asteraceae)

Studio dell'attività biocatalitica delle piante del genere Citrus: risultati preliminari

ChemInform Abstract: Further Furoclerodanes from Teucrium “maghrebinum”

Two more pairs of C-12 epimeric neoclerodanes were isolated from the aerial parts of Teucrium “maghrebinum” (Teucriumpolium subspecies still unidentified). They are the known teukotschyn 1, the new 12-epi-teukotschyn 2, the new teughrebin 3 and the new 12-epi-teughrebin 4. The structures of the new products were elucidated mainly by spectroscopic methods.

Neoclerodanes from Teucrium orientale

Abstract Two new neoclerodane diterpenoids, 6-deacetyl-teucrolivin A (5) and 8beta-hydroxy-teucrolivin B (6), were isolated from the aerial parts of Teucrium orientale, along with four already known neoclerodane diterpenoids, teucrolivin A (1), teucrolivin B (2), teucrolivin C (3) and teucrolivin H (4), previously isolated from Teucrium oliverianum. Their structures were elucidated on the basis of spectroscopic evidence and chemical transformations. Compounds 1-3 were assayed for antifeedant activity against Spodoptera littoralis, S. frugiperda and Heliocoverpa armigera. Teucrolivin A was the most potent of the three compounds tested.

Chemical composition of the essential oil from Thapsia garganica L. (Apiaceae) grown wild in Sicily and its antimicrobial activity.

In this study, the chemical composition of the essential oil from flowers and leaves of Thapsia garganica L. collected in Sicily was evaluated by GC and GC-MS. The main components of T. garganica flower oil (T.f.) were chamazulene (58.3%), humulene oxide II (9.0%), tricosane (8.2%) and pentacosane (8.2%). Also the oil from leaves (T.l.) was characterised by high content of chamazulene (49.2%). Other abundant metabolites were 1,4-dimethylazulene (18.5%), (E)-phytol (6.3%) and neophytadiene (5.1%). The comparison with other studied oils of genus Thapsia is discussed. Antimicrobial activity against several micro-organisms, including some ones infesting historical art craft, was also determined.

Fixed oil from seeds of narrow-leaved ash (F. angustifolia subsp. angustifolia): Chemical profile, antioxidant and antiproliferative activities.

Fraxinus angustifolia subsp. angustifolia is a plant with an age-old use for the production of manna. However, it is also a valuable source of fixed oil rich-seeds. In the present study we examined the chemical and biological properties of this oil in order to support a possible application in foodstuffs, nutraceuticals and cosmetics. Fatty acid composition, volatile and phenolic substances were evaluated. Oleic and linoleic acid represented 45.5% and 50.0%, respectively, of the total fatty acid composition. Among polar phenolic substances identified (secoiridoids, phenylethanoid glycosides, phenolic acids and alcohols, flavonoids, coumarins) isoverbascoside is for the first time reported i…

Guaianolides and lignans from the aerial parts of Centaurea ptosimopappa.

The genus Centaurea L. (Asteraceae, tribe Cardueae, subtribe Centaureinae) comprises ca. 600 species distributed in Asia, Europa, North Africa and America (Hickey and King, 1981; Heywood, 1979). Turkish flora numbers 187 species, 114 of which being endemic (Davis, 1975; Davis et al., 1988; Wagenitz et al., 1988; Guner et al., 2000; Duran and Duman, 2000; Turkoglu et al., 2003). Centaurea ptosimopappa Hayek is an endemic species distributed in the Mediterranean and South-Eastern Anatolian regions of Turkey; widespread and locally frequent in the Amanos and Casus mountains (Davis, 1975; Reeves and Adiguzel, 2004). Aerial parts of C. ptosimopappa were collected in Hatay, the Amanos Mountain ab…

Phytochemical composition and antimicrobial activity of essential oil from different parts of Ferulago campestris growing wild in the Natural Park of Madonie (Sicily)

Cytotoxic activity of some natural and syntetic sesquiterpene lactones

Several natural and synthetic sesquiterpene lactones with different skeletons were tested and found to be active against nine cancer cell lines. Elemane (4), heliangolane (5) and their hydroxy analogues 9 and 10, all containing an α,β-unsaturated aldehyde substituent, were the most potent compounds.

Graphene oxide-silica nanohybrids as fillers for PA6 based nanocomposites

Graphene oxide (GO) was prepared by oxidation of graphite flakes by a mixture of H2SO4/H3PO4 and KMnO4 based on Marcano's method. Two different masterbatches containing GO (33.3%) and polyamide-6 (PA6) (66.7%) were prepared both via solvent casting in formic acid and by melt mixing in a mini-extruder (Haake). The two masterbatches were then used to prepare PA6-based nanocomposites with a content of 2% in GO. For comparison, a nanocomposite by direct mixing of PA6 and GO (2%) and PA6/graphite nanocomposites were prepared, too. The oxidation of graphite into GO was assessed by X-ray diffraction (XRD), Micro-Raman spectroscopy, scanning electron microscopy (SEM), X-ray photoelectron spectrosco…

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

Ferulago nodosa Subsp. geniculata (Guss.) Troia &amp; Raimondo from Sicily (Italy): Isolation of Essential Oil and Evaluation of Its Bioactivity

Ferulago nodosa (L.) Boiss. (Apiaceae) is a species occurring in the Balkan-Tyrrhenian area. The object of the present study is Sicilian F. nodosa subsp. geniculata (Guss.) Troia & Raimondo, classified as an endemic F. nodosa subspecies. Aerial parts of this plant species were subjected to hydrodistillation to obtain an essential oil. A total of 93 compounds were identified with 2,3,6-trimethyl benzaldehyde (19.0%), spathulenol (9.0%), (E)-caryophyllene (5.4%), and caryophyllene oxide (5.4%) as the main components. The biological activities of F. nodosa essential oil were also investigated. This oil showed an interesting antioxidant potential in a 2,2′-Azino-bis(3-ethylbenzothiazoline-6-sul…

Fetid odors in Caralluma europaea (Guss.) N.E.Br. (Apocynaceae-Asclepiadoideae): a chemical characterization

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%…

Neoclerodane Diterpenoids from Teucrium maghrebinum

Eight neoclerodane diterpenoids were identified in the extract of the aerial parts of Teucrium maghrebinum. Three of these, 12-epi-teucjaponin A (1), 12-epi-montanin D (2), and 12-epi-montanin B (3), are new natural products, whereas five, teucjaponin A, montanin D, 19-deacetylteuscorodol, teusalvin C (4), and montanin B, are already known. These eight compounds form four pairs of epimers at carbon C-12.

ChemInform Abstract: Photoinduced Functionalization of the C-20 Methyl Group of the Nor-diterpene Atractyligenin.

Abstract Irradiation of the nor-diterpene atractyligenin at λ =254 nm in methanol gave, on one hand, the decarboxylation product, and provided, on the other hand, the transformation of the C-20 angular methyl into a methylene-carbomethoxy group. A photochemical pathway involving formation of C-19/C-20 bond is suggested.

Studio della reazione di Grignard su derivati dell'acido ursolico

NMR-based quantification of rosmarinic and carnosic acids, GC-MS profile and bioactivity relevant to neurodegenerative disorders of Rosmarinus officinalis L. extracts

Abstract A comparative study of phytochemicals content and biological properties of eight Rosmarinus officinalis (rosemary) populations (RO1–RO8) collected in different areas of Tunisia was carried out. Two of the main rosemary constituents, rosmarinic and carnosic acids, were quantified by an NMR technique. Carnosic acid content was higher than that of rosmarinic acid. The non-polar constituents were examined by GC and GC–MS. Total phenols and flavonoids content were also determined in order to discuss the possible correlation between these phytochemicals and bioactivity. Antioxidant activity was investigated through different in vitro assays. Sample RO3 from a sub-humid area showed the hi…

A novel approach to prevent graphene oxide re-aggregation during the melt compounding with polymers

Abstract The technology for the preparation of polymer-GO nanocomposites was investigated by studying the structure-properties relationships of two different systems, based on PA6 and EVA, fabricated by using different preparation methods, i.e. melt mixing, wet phase inversion, and the combination of the two. The morphology of nanocomposites resulted dramatically influenced by the technique adopted and showed to be the critical variable affecting the physical properties of the materials. Finally, the mechanical and dynamic-mechanical of the nanocomposites were improved by using the hybrid technique combining the two procedures.

Sintesi di lattoni sesquiterpenici e loro attività citotossica

Solid state 13C-NMR methodology for the cellulose composition studies of the shells of Prunus dulcis and their derived cellulosic materials.

Lignocellulosic fibers and microcellulose have been obtained by simple alkaline treatment from softwood al- mond shells. In particular, the Prunus dulcis Miller (D.A.) Webb. was considered as a agro industrial waste largely available in southern Italy. The materials before and after purification have been characterized by 13C CPMAS NMR spectroscopy methodology. A proper data analysis provided the relative composition of lignin and holo- cellulose at each purification step and the results were compared with thermogravimetric analysis and FT-IR. To value the possibility of using this material in a circular economy framework, the fibrous cellulosic material was used to manufacture a handmade c…

Natural products and derivatives from Ferulago campestris (Apiaceae)

Indagini fitochimiche sul galbano di Sicilia

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.

Sesquiterpene lactones and other constituents of three Cardueae from Cyprus

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.

Cytotoxic geranylflavonoids from Bonannia graeca

The analysis of the aerial parts of Bonannia graeca led to the isolation and characterization of two new polar geranylated flavonoids (6 and 7). The structure elucidation was performed by extensive spectroscopic methods (1D and 2D NMR) and comparison with literature data. All natural flavonoids isolated from B. graeca (1–7) and some synthetic derivatives (8–11) were tested for cytotoxic activity against four human tumor cell lines. Preliminary structure-activity relationship correlations are discussed.

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…

Citrus peels as biocatalyst for deacetylation reactions

The first example of natural cyclic carbonate in terpenoids

Abstract The first natural occurring cyclic carbonate terpenoid, the guaianolide hololeucin ( 1 ), was isolated from the aerial part of Centaurea hololeuca . Its structure was elucidated on the basis of extensive proton, 13 C and two-dimensional NMR experiments, as well as by transformation in its diacetyl derivative.

Phytochemical investigation of the needles of Aabies nebrodensis (Lojac.) Mattei

Abies nebrodensis (Lojac.) Mattei (Pinaceae) is a species living in a very small population only in a confined area of Sicily. In this study, the dichloromethane extract of the leaves was analyzed. Apart from three already known metabolites namely dehydroabietic acid; maltol; and rheosmin, previously detected in other species of Abies, a lanostane derivative was isolated. Its chemical structure was elucidated by means of extensive spectroscopic methods.

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.

Antibacterial and anticoagulant activities of coumarins isolated from the flowers of Magydaris tomentosa (Desf.) DC (Apiaceae)

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 μg/mL), the most active being imperatorin (3) (MICs between 32 and 128 μg/mL) and citropten (4) (MICs between 16 and 256 μg/mL). The anticoagulant activity of compounds 1-…

Minor diterpenoids from Scutellaria polyodon.

Four minor neoclerodane diterpene constituents were isolated from the aerial parts of Scutellaria polyodon. These compounds were characterized as the new scupolins J (1) and K (2) and the previously known scutalpin O (3) and scutalsin.

The cytotoxic activity of natural and semisynthetic sesquiterpene lactones

Monoterpene derivatives from the flowers of Ferulago campestris, (Apiaceae).

Ferulago campestris (Besser) Grec., (Ferula galbanifera (Mill) Kock. = F. campestris), finocchiazzo, is an annual or perennial herb of the Mediterranean area. In this paper the phytochemical studies of the CH2Cl2 and MeOH extracts of the flowers are described. Several ferulol derivatives and a new 10-hydroxy-verbenone ester (7) were isolated. The structure of the new compound was established by extensive NMR analysis, including HMBC and HSQC pulse sequences.

Conformational analysis and DFT calculations of 8α-hydroxy-germacradiene-6,12-olide derivatives

The Systematic Conformational Search Analysis (SCSA) code was employed to study the conformational properties of the 8α-hydroxy-germacradiene-6,12-olide isomers. This procedure was extended to the trans,cis- and trans,trans-1(10),4-isomers of 8α,15-dihydroxy-germacradiene-6,12-olides and 8α-hydroxy-15-oxo-germacradiene-6,12-olides, to investigate structural and energetic analogies between these and the 8α-hydroxy-germacradiene-6,12-olide species. The calculated 13C NMR spectra, at the hybrid DFT mPW1PW91 level, showed a sound correlation with the corresponding experimental spectra, providing a valid support to the reliability of the calculated structures and to the consistence of our confor…

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.

Antifeedant activity of neo-clerodane diterpenoids from Teucrium fruticans and derivatives of fruticolone

The antifeedant activity of three neo-clerodane diterpenoids, fruticolone, isofruticolone and fruticolide from Teucrium fruticans was assessed using larvae of Spodoptera littoralis. Isofruticolone was one of the most potent of the Teucrium derived neo-clerodanes. Chemical modification of functional groups on fruticolone showed that its activity could be enhanced.

Cytotoxic Activity of Some Natural and Synthetic ent-Kauranes

Atractyligenin (1) and several synthetic derivatives were tested and found to be active against tumor cell replication. Compound 1 was readily converted to the 2,15-diketo (3) or 15-keto (4) derivatives, which contain an alpha,beta-unsaturated ketone. Compounds 3 and 4 showed significant cytotoxic activity against all six tested cancer cell lines and were most potent against 1A9 ovarian cancer cells with EC50 values of 0.2 and 0.3 microM, respectively. These two 1-analogues are promising lead compounds for further investigation.

Conformational analysis and DFT calculations of 8 alpha-hydroxy-germacradiene-6,12-olide derivatives

The Diterpenoids from the Genus Hyptis (Lamiaceae)

The genus Hyptis (family Lamiaceae) is known mainly for the essential oils isolated from the aerial parts of several species. Less known are the diterpenoids, extracted from a limited number of species. In consideration of the interest for the structures of this class of compounds, largely occurring in the whole Lamiaceae family, the present paper means to review and update their chemistry. Also the use of many species of Hyptis in folk-medicine is reported.

The Cytotoxic Properties of Natural Coumarins Isolated from Roots ofFerulago campestris(Apiaceae) and of Synthetic Ester Derivatives of Aegelinol

Grandivittin (1), agasyllin (2), aegelinol benzoate (3) and felamidin (20), four natural coumarins isolated from Ferulago campestris, and several synthetic ester derivatives of aegelinol (4) were tested against four tumor cell lines. Some of them were shown to be marginally cytotoxic against the A549 lung cancer cell line.

Antimicrobial activity of coumarins from the roots of Ferulago campestris (Apiaceae)

Metabolites from the Aerial Parts of the Sicilian Population of Artemisia alba

Phytochemical investigation of the CH2Cl2 extract of the aerial parts of Artemisia alba Turra afforded one new irregular sesquiterpenoid, artemiric acid, and five known metabolites: hydroxydavanone, the coumarins isofraxidin and scopoletin, (6 S*,7 S*,10 R*)–6,10-dimethyl-7,10-epoxyocta-11-enoic acid and artalbic acid. From the MeOH extract three flavonoids were identified: chrysoeriol, quercetin and isorhamnetin. The possible biogenetic pathways of artemiric and artalbic acids are discussed.

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

Rapid and eco-friendly synthesis of graphene oxide-silica nanohybrids

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…

Nuovi flavonoidi da Bonannia graeca (L.) Halácsy e loro attività biologica

Hand-made paper obtained by green procedure of cladode waste of Opuntia ficus indica (L.) Mill. from Sicily

Cellulosic fibres have been obtained by green procedures from the cladodes of Opuntia ficus indica (L.) Mill., constituting a large agro industrial waste in our territory. The materials have been analysed for its relative composition, applying, IR and TG methodologies and it was characterised by the absence of lignin. The fibrous material allowed the manufacture of a handmade paper obtaining an ecological material suitable for packaging purposes. The authors evidenced that the simple protocol based on hot water treatment was able to decrease the amount of hemicellulose in the final material.

Flavonoids from Teucrium fruticans L.

From aerial parts of &lt;em&gt;Teucrium fncticans&lt;/em&gt; L. three flavonoids were isolated and identified as 5-hydroxy-6, 7, 3', 4'-tetramethoxyflavone, 5, 4'-dihydroxy-6, 7, 3'-trimethoxyflavone (cirsilineol) and 5, 4'-dihydroxy-6, 7-dimethoxyflavone (cirsimaritin). The former compound was found to be a predominant flavone aglycone constituent of the plant material. This is the first report on the isolation of flavonoids from the plant.

Effects of air pollution on production of essential oil in Feijoa Sellowiana Berg. grown in the "Italian triangle of death"

The composition of the essential oils of fruits from Feijoa sellowiana grown in the district of Acerra is compared with those collected from unpolluted sites. Essential oils from the fruits of F. sellowiana were analysed by GC/MS. Sixty compounds, representing 96.6% and 97.8% (unpolluted site and Acerra site, respectively) of the oils, were identified. The major constituents were β-caryophyllene (12.4% and 16.8%), ledene (9.6% and 11.1%), α-humulene (6.3% and 8.2%), β-elemene (4.9% and 5.3%) and δ-cadinene (4.7% and 5.2%) in the control site and Acerra site, respectively. The antioxidant components were increased in response to polluted condition. The acetonic extracts of F. sellowiana from…

A Review of the Phytochemistry, Traditional Uses, and Biological Activities of the Genus Ballota and Otostegia

AbstractThe 2 genera Ballota and Otostegia, belonging to the Lamiaceae family, are closely related taxonomically and found mainly in the Mediterranean area, Middle East, and North Africa. Since ancient times, they have been largely employed in traditional medicine for their biological properties such as antimicrobial, anti-inflammatory, antispasmodic, insecticidal, anti-malaria, etc. Phytochemical investigations of Ballota and Otostegia species have revealed that diterpenoids are the main constituents of the genera. A large number of flavonoids and other metabolites were also identified. This review, covering literature from 1911 up to 2018, includes traditional uses, chemical profiles (bot…

Ceiba speciosa (A. St.-Hil.) Seeds Oil: Fatty Acids Profiling by GC-MS and NMR and Bioactivity

This study aimed to evaluate the chemical composition by gas chromatography-mass spectrometry (GC-MS) and Nuclear Magnetic Resonance (NMR) analyses, the antioxidant activities evaluated by different in vitro assays namely 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2&prime

Essential oils composition of two Sicilian cultivars of Opuntia ficus-indica (L.) Mill. (Cactaceae) fruits (prickly pear).

The essential oils composition of the skin, pulp and seeds from fruits of two Sicilian cultivars of Opuntia ficus-indica (cv. Sanguigna and cv. Surfarina) has been obtained by hydrodistillation and the possible antioxidant, antimicrobial and semiochemical roles have been investigated comparing the data with those reported in the literature. The presence of antioxidants and antimicrobials found in this study increases the spectrum of compounds that have beneficial properties in O. ficus-indica. In addition, several compounds identified in this study have been reported to influence the behaviour of Ceratitis capitata, a phytophagous pest which causes severe damages to several crops including …

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.

Artalbic acid, a sesquiterpene with an unusual skeleton from Artemisia alba (Asteraceae) from Sicily

Abstract From the aerial parts of Artemisia alba (Asteraceae) artalbic acid ( 1 ), a sesquiterpene with an unusual skeleton, was isolated. Its structure was elucidated on the basis of extensive proton, 13 C and two-dimensional NMR experiments, as well as by transformation in its methyl ester derivative.

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.

Guaianolides from Centaurea babylonica

Further Furoclerodanes fromTeucrium “maghrebinum”

Two more pairs of C-12 epimeric neoclerodanes were isolated from the aerial parts of Teucrium “maghrebinum” (Teucriumpolium subspecies still unidentified). They are the known teukotschyn 1, the new 12-epi-teukotschyn 2, the new teughrebin 3 and the new 12-epi-teughrebin 4. The structures of the new products were elucidated mainly by spectroscopic methods.

Functional investigation and applications of the acetylesterase activity of the Citrus sinensis (L.) Osbeck peel

The hydrolysis of acetyl moieties on a set of commercially relevant substrates was performed by employing the whole tissue of Citrus sinensis (L.) Osbeck peel as an efficient biocatalyst in mild reaction conditions with high degree of regioselectivity. The reaction is done in aqueous media and the product is easily recovered. Optimal reaction conditions were deduced and two practical applications were investigated: the elaboration of acetylglicerols and the preparation of vitamin K1 precursor. Peel waste (flavedo and albedo) from orange juice manufacturing was successfully employed as a biocatalyst.

Bioactive Constituents of Juniperus turbinata Guss. from La Maddalena Archipelago.

A comprehensive phytochemical study of Juniperus turbinata (Cupressaceae) collected from La Maddalena Archipelago (Sardinia, Italy) is reported. Both the essential oil and the ethanolic extract obtained from the aerial parts were analyzed. The essential oil appears to belong to a new chemotype compared to other Mediterranean juniper accessions, as it was favored by geographic isolation of the isles. It showed a low content of monoterpene hydrocarbons and -terpineol, ent-manoyl oxide, 1,10-di-epi-cubenol as the major constituents. The ethanolic fraction contained mainly diterpenoids. Among these, 15-formyloxyimbricatolic acid (7) is a new natural product since it has hitherto been obtained o…

Metaboliti secondari in Caralluma europaea

Effect of Marrubium globosum ssp libanoticum on intestinal motility

Essential Oil Composition of Alluaudia procera and in Vitro Biological Activity on Two Drug-Resistant Models

Drug resistance is a major obstacle in antibiotic and antitumor chemotherapy. In response to the necessity to find new therapeutic strategies, plant secondary metabolites including essential oils (EOs) may represent one of the best sources. EOs in plants act as constitutive defenses against biotic and abiotic stress, and they play an important role in the pharmacology for their low toxicity, good pharmacokinetic and multitarget activity. In this context, natural products such as EOs are one of the most important sources of drugs used in pharmaceutical therapeutics. The aim of this paper was to identify the chemical composition of the essential oil of Alluaudia procera leaves, obtained by hy…

Phytochemical investigation of the needles of Abies nebrodensis (Lojac.) Mattei

Abies nebrodensis (Lojac.) Mattei (Pinaceae) is a species living in a very small population only in a confined area of Sicily. In this study, the dichloromethane extract of the leaves was analyzed. Apart from three already known metabolites namely dehydroabietic acid; maltol; and rheosmin, previously detected in other species of Abies, a lanostane derivative was isolated. Its chemical structure was elucidated by means of extensive spectroscopic methods.

Chemical composition of volatile and fixed oils from of Salvia argentea L. (Lamiaceae) growing wild in Sicily.

The chemical compositions of the essential oil and of the non-polar extracts (petroleum ether, dichloromethane) of the aerial parts (flowers, leaves and stems) of Salvia argentea L. were determined by GC-FID and gas chromatography–mass spectrometry analysis. 14-Hydroxy-α-humulene (40.1%) was recognised as the main constituents of the essential oil of S. argentea, together with 1,3,8-p-menthatriene (12.1%), globulol (7.4%) and β-sesquiphellandrene (5.8%). Tritriacontane (9.9% and 14.1%), heptacosane (8.4% and 10.5%), hentriacontane (8.3% and 10.9%), tetradecanal (8.4% and 10.2%) and methyldotriacontane (7.9% and 7.6%) were recognised as the main constituents of the extracts in petroleum …

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…

Chemical composition of the essential oil from aerial parts of Stachys palustris L. (Lamiaceae) growing wild in Southern Italy

The paper reports the composition of the essential oil from aerial parts of Stachys palustris L. (Lamiaceae) from Southern Italy. The essential oil was extracted by hydrodistillation from selected plants and its chemical composition was determined by the GC-MS system on two fused- silica capillary columns of different polarity. The mass fraction of oil was 0.21 % on a dry weight basis. Altogether, 92 compounds were identified accounting for 93.6 % of the total oil, which was characterized mainly by carbonylic compounds (25.4 %), fatty acids and their esters (24.2 %), along with sesquiterpenoidic compounds (16.0 %) and phenols (11.2 %). The major components of the sample were caryophyllene o…

Chemodiversity of the essential oil from leaves of Abies nebrodensis (Lojac.) Mattei

As activities of the project "Preservation of Abies nebrodensis and restore of Geraci Siculo peatlands", the chemical composition of essential oils, obtained from leaves of Madonie fir, was compared with the ones of essential oils derived from Eurasian species studied up to now

Potential allelopathic activity ofSideritis italica(Miller) Greuter et Burdet essential oil

Sideritis italica (Miller) Greuter et Burdet is a widespread Mediterranean Lamiacea. Essential oils from S. italica flowerheads and leaves were extracted by hydrodistillation and then tested for their potential allelopathic activity against Raphanus sativus L. (Magnoliophyta) and the moss Tortula muralis (Hedw.) (Bryophyta), two organisms already tested for allelopathy, and against two bryophytes growing in the same environment as S. italica: the moss Bryum capillare Hedw. and the liverwort Lunularia cruciata (L.) Dum. For R. sativus, we considered seed germination and root and epicotyl growth. For the mosses, we used spore germination and protonemata development, while for the liverwort, w…

Essential Oils and Pure Volatile Compounds as Potential Drugs in Alzheimer's Disease Therapy: An Updated Review of the Literature

Background: The use of aromatic plants to relief different illness is not a new therapy. Actually aromatic plants have been used for many centuries by different cultures around the world. Pharmacological studies provide scientific support to the traditional use of aromatic medicinal plants and aromatherapy; nevertheless, more clinical trials are required regarding to their effectiveness in order to establish a guidance for their use in routine healthcare. Moreover, modern medicine in studies about olfactory function has attained great achievements and got Nobel Prize in 2004. These new searches have obviously fueled interest in the essential oils and volatile compounds of natural origin. Se…

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.

The cytotoxic activity of natural and semisynthetic guaianolides

Indagine fitochimica sulle radici di Helleborus bocconei Ten. subsp. intermedius.

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…

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

The essential oil of roots, branches, leaves, flowers and fruits of Periploca laevigata Aiton subsp. angustifolia (Apocynaceae) from Lampedusa Island has been obtained by hydrodistillation and its composition analysed. The analyses allowed the identification and quantification of 86 volatile compounds. Branches showed the higher diversity with 57 compounds followed by fruits with 33, roots with 23, flowers with 16 and leaves with six compounds, respectively. In the matrices examined three constituents, heneicosane, docosane and tricosane are in common, although with different percentages. At least the most abundant compounds found in the matrices have been reported to have several biologica…

Chemical Composition, In Vitro Antitumor and Pro-Oxidant Activities of Glandora rosmarinifolia (Boraginaceae) Essential Oil

The biological properties of essential oils have been demonstrated in the treatment of several diseases and to enhance the bioavailability of other drugs. In natural habitats the essential oils compounds may play important roles in the protection of the plants as antibacterials, antivirals, antifungals, insecticides and also against herbivores by reducing their appetite for such plants or by repelling undesirable others. We analyzed by gas-chromatography mass spectrometry the chemical composition of the essential oil of aerial parts of Glandora rosmarinifolia (Ten.) D.C. Thomas obtained by hydrodistillation and verified some biological activities on a panel of hepatocellular carcinoma cell …

Metabolites from the aerial parts of the Sicilian population of Artemisia alba Turra

Phytochemical investigation of the CH2Cl2 extract of the aerial parts of Artemisia alba Turra afforded one new irregular sesquiterpenoid, artemiric acid, and five known metabolites: hydroxydavanone, the coumarins isofraxidin and scopoletin, (6S*,7S*,10R*)-6,10-dimethyl-7,10-epoxyocta-11-enoic acid and artalbic acid. From the MeOH extract three flavonoids were identified: chrysoeriol, quercetin and isorhamnetin. The possible biogenetic pathways of artemiric and artalbic acids are discussed.

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.

Sintesi e attività antitumorale di derivati dell'acido ursolico

Secondary metabolites from Pinus mugo Turra subsp. mugo growing in the Majella National Park (Central Apennines, Italy).

In this study, we examined the composition regarding secondary metabolites of P. mugo Turra ssp. mugo growing in the protected area of Majella National Park, which is the southernmost station of the habitat of this species. Both the nonpolar and polar fractions were considered. In particular, the essential-oil composition showed a high variety of compounds, and 109 compounds were detected, and 101 were identified, among which abietane-type compounds have a taxonomic relevance. Abietanes were also isolated from the polar fraction, together with an acylated flavonol and a remarkably high amount of shikimic acid.

Volatile constituents of aerial parts of Lasiopogon muscoides

Phytochemical profile and insecticidal activity of Drimia pancration (Asparagaceae) against adults of Stegobium paniceum (Anobiidae)

Chemical and spectroscopic investigation of the bulbs of Drimia pancration resulted in the isolation of one known flavonol (1), never isolated from this plant species, and of three previously described steroidal saponins (2–4), but whose configuration at their stereogenic centres was not clearly determined. By mean of 1H NMR, 13C NMR, nuclear overhauser effects (NOE) and two-dimensional NMR spectra the full stereochemical structures of compounds 2–4 were proved and all the 1H and 13C signals were assigned. Furthermore, the methanol and butanol extracts of D. pancration were tested against adults of Stegobium paniceum beetles. Despite the non-significant results regarding the repellent activ…

New oxidative derivatives of atractyligenin and their cytotoxic activity

ent-Kauranes are naturally occurring diterpenoids isolated from several families, such as Asteraceae and Lamiaceae. These compounds have attracted interest because of their structures and their biological activities as anti-tumorals, anti-HIV and anti-bacterials [1]. Extensive chemical work [2] was carried out on the structure of atractyligenin, the nor-diterpene aglycone of the glucoside atractyloside, occurring, together with its diterpene homologous carboxy-atractyloside, in the root of Atractylis gummifera L. (Compositae). The interest for these compounds was stimulated by the high toxicity [3] of both glucosides, responsible of many deadly poisoning in past time. Due to the 15-hydroxyl…

The diterpenoids from the genus Sideritis

ABSTRACT: The genus Sideritis consists of 100-150 or more species, growing mainly in the countries around the Mediterranean area. The genus is particularly rich in diterpenoids, occurring in almost all the species, and shows many different carbon skeleta. Several species are still used in traditional medicine. Recent studies indicated the occurrence of interesting biological activities, like anti-inflammatory, antibacterial, antimicrobial, anti-HIV replication, antifeedant, antiulcerogenic, analgesic, and antihypoglycaemic.

Synthesis of Rosmarinic Acid Amides as Antioxidative and Hypoglycemic Agents

Type 2 diabetes mellitus (T2DM) is an important metabolic disorder for which there is an urgent need for new antidiabetic drugs. α-Glucosidase inhibition is an established protocol for T2DM therapy. Because hyperglycemia causes oxidative tissue damage, the development of agents with both α-glucosidase inhibition and antioxidant activity from natural or natural-derived polyphenols such derivatives of rosmarinic acid (RA) represents an attractive therapeutic option. We report a study on amides 1-10 derived from RA and their evaluation for yeast α-glucosidase inhibition and antioxidant activity (DPPH and ORAC tests). All amides showed higher inhibitory activity than that of RA, were by far mor…

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.

Chemical composition and anticancer activity of essential oil of Mediterranean sage (Salvia officinalis L.)

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)

Lignans and an unusual steroids from the seeds of Centaurea sclerolepis Boiss

ChemInform Abstract: Natural and Hemisynthetic Neoclerodane Diterpenoids from Scutellaria and Their Antifeedant Activity

Covering: Up to June 2001. Previous review: on the clerodanes, Nat. Prod. Rep., 1992, 9, 243.

Structure and Biological Activity of the Furan-Diterpenoids from the Genera Leonotis and Leonurus

The present review, covering the literature up to 2006, reports the chemistry and the biological activities of the diterpenoids occurring in the aerial parts of species belonging to the genera Leonotis and Leonurus, family Lamiaceae.

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.

Attività citotossica di derivati ent-kauranici.

The ethnobotany, phytochemistry and biological properties of genus Ferulago – A review

Abstract Ethnopharmacological relevance The genus Ferulago, belonging to the Apiaceae family, is found mainly in the Mediterranean area, Southwest and Middle Asia, the Caucasus and North Africa. Since ancient times, species of this genus have been largely employed in traditional medicine for their biological properties such as antimicrobial, anti-inflammatory, antispasmodic, insecticidal, and anti-malaria, cholinesterase inhibition effects, etc. Aims The scope of this paper is to present a comprehensive respect review of this interesting genus including traditional uses, chemical composition of volatile and non-volatile metabolites, and in vitro and in vivo biological properties either util…

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

Photoinduced functionalization of diterpenes: photochemical behaviour of grandifloric acid in methanol and acetonitrile

Abstract Irradiation of grandiflorolic acid (11) at λ=254 nm in acetonitrile gave the two epimers 13 and 14 through a photodecarboxylation reaction of the carboxylic group on C-4. Irradiation of compound 11 in methanol at λ=254 nm provided the transformation of the C-20 angular methyl into a carbomethoxymethyl group. In this case, unlike compounds 13 and 14, only one of the two possible isomers (15) was obtained (equatorial methyl at C-4). A mechanistic approach of this reaction in discussed, and the role of mutual stereochemistry between C-20 methyl and C-19 carboxylic group in determining the course of the reaction is pointed out.

Phytochemical investigation of four Teucrium species

Essential Oils of Chiliadenus Lopadusanus (Asteraceae)

The essential oils from the leaves and flowers of Chiliadenus lopadusanus growing on Lampedusa Island were obtained by hydrodistillation and analyzed by GC-MS. The major component was camphor (39.4% in the leaves and 24.0% in the flowers), followed in the leaves by torreyol (6.7%), t-cadinol (5.2%) and 1,8-cineole (3.8%), while in the flowers by t-cadinol (15.2%), t-muurolol (5.1%) and torreyol (4.5%). Among the compounds identified, several seem to play a role in antibacterial, antifungal, allelopathic and spasmolytic activity. In addition, several compounds identified in this study seem to influence the attraction of Megachile ( Eutricharaea) apicalis (Megachilidae) and Halictus ( Selado…

Cytotoxic activity of some natural and synthetic guaianolides

Several natural guaianolides and synthetic derivatives of repin (1) were tested and found to be active against tumor cell replication. Repin (1) and both mono- and di-halohydrin analogues (2, 7-9, 11, 12) showed significant antitumor potency. A more effective compound (17) was obtained by esterificating repin with the paclitaxel side chain.

Chemical composition of the essential oil 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.

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. alpha-Thujone, beta-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.

Enzyme-catalysed transformations of ent-kaurane diterpenoids

Several acetyl derivatives of linearol, atractyligenin and atractylitriol were obtained through enzyme-catalysed acetylation and deacetylation reactions. In most reactions lipases showed regio- and stereoselective behaviour, allowing a family of novel compounds to be prepared. Fil: Monsalve, Leandro Nicolas. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y …

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%).

Rearrangement of Germacranolides. Synthesis and Absolute Configuration of Elemane and Heliangolane Derivatives from Cnicin

A study of the Cope rearrangement of 15-oxo-germacranolides to 15-oxo-elemanolides has been carried out. The synthesis of two natural elemanolides, isolated from Centaurea paui, and an efficent isomerization of the C-4/C-5 double bond of 15-oxo-germacranolides to form heliangolides are reported. The absolute configuration of all the compounds has been ascertained. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

Hastifolins A-G, antefeedant neo-clerodane diterpenoids from Scutellaria hastifolia

From the aerial parts of Scutellaria hastifolia, family Lamiaceae (Labiatae), seven neo-clerodane diterpenoids (hastifolins A-G) were isolated. The products are similar to the known scuteparvin and are characterized by being trans-cinnamoyl derivatives. Structures and stereochemistry were determined by intensive NMR investigation. Six of the products form three pairs of epimers at C-13. Hastifolins A-C showed significant antifeedant activity.

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 …

Synthesis of β-methylfurolabdanes from (+)-sclareolide

An efficient synthesis of the methylfurolabdane 3 from (+)-sclareolide (6) via the hydroxyalkenes 12 is reported. Alternative modes of cyclization of 12 allowed the synthesis of methyldihydrofuran derivatives 4 and 5 and methyltetrahydrofuran derivatives 15. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002)

Biological activities of natural guaianolides from Centaurea hololeuca Boiss and their derivatives

Photoinduced functionalization of the C-20 methyl group of the nor-diterpene atractyligenin

Abstract Irradiation of the nor-diterpene atractyligenin at λ =254 nm in methanol gave, on one hand, the decarboxylation product, and provided, on the other hand, the transformation of the C-20 angular methyl into a methylene-carbomethoxy group. A photochemical pathway involving formation of C-19/C-20 bond is suggested.

Cytotoxic Effect of Eudesmanolides Isolated from Flowers of Tanacetum vulgare ssp. siculum

WOS: 000306752700042

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.

The metabolites of the genus onopordum (asteraceae): Chemistry and biological properties

Onopordum is an interesting genus belonging to the tribe Cardueae (Asteraceae family), and the species of this genus are used as food and in the popular medicine of several countries. The present paper reviews all the metabolites present in all the species of this genus, reported up to 2009, and several chemotaxonomic consideration have been made. Furthermore, the occurrence in other genus, the spectral data, the synthetic approaches, the chemical modifications and the biological properties of the sesquiterpenes of genus Onopor- dum have been reviewed.

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%).

A Review of the Phytochemistry, Traditional Uses and Biological Activities of the Essential Oils of Genus Teucrium

AbstractThe genus Teucrium is a large and polymorphic genus of the Lamiaceae family distributed in mild climate zones, particularly in the Mediterranean basin and Central Asia. Studies of nonvolatile constituents of Teucrium species showed that they are a rich source of neo-clerodane diterpenoids, considered as chemotaxonomic markers of the genus. In addition to the nonvolatile metabolites, there has been a large interest in the essential oils of this genus. In this review, a complete survey of the chemical composition and biological properties of the essential oils isolated from Teucrium taxa is provided. In traditional medicine, since ancient times, species of this genus have been widely …

Antimicrobial and Antioxidant Activities of Coumarins from the Roots of Ferulago campestris (Apiaceae)

We report the isolation of several coumarins and the stereochemical assessment of some pyranocoumarins, as well as the antibacterial and antioxidant activities of the three most abundant ones (grandivittin, agasyllin and aegelinol benzoate) isolated from the roots of Ferulago campestris collected in Sicily and of the hydrolysis product (aegelinol). Aegelinol and agasyllin showed antibacterial activity against nine ATCC and the same clinically isolated Gram-positive and Gram-negative bacterial strains. At a concentration between 16 and 125 μg/mL both coumarins showed a significant antibacterial effect against both Gram-negative and Gram-positive bacteria. In particular the ATCC strains Staph…

Acid Rearrangment of Epoxy-germacranolides and Absolute Configuration of 1β,10α-Epoxy-salonitenolide

The acid-catalyzed cyclization of mono epoxides of cnicin acetonide (3) was investigated. Several 6,12-eudesmanolides were obtained, and their stereochemistry established by extensive spectroscopic analyses. Chemical correlations also led to the assignment of the absolute configuration of 1β,10α-epoxy-salonitenolide (13), a previously isolated natural product. The cytotoxic activities of some compounds were determined against A549 and MCF-7 tumor cell lines. The esterified germacranolides 2–6 were selectively cytotoxic against the MCF-7 breast cancer cell line.

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

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

Floral scent in a sexually deceptive Ophrys orchid: from headspace collections to solvent extractions

Sexually deceptive orchid flowers use visual, tactile and olfactory cues of female insects in order to attract males of one or a few closely related species as pollinators. Ophrys L. is the most species-rich genus of sexually deceptive orchids in the Mediterranean Basin. Despite Ophrys pollinated by Andrena male bees use alkanes and mainly alkenes with specific double-bond positions as key signals that trigger pseudocopulatory behavior, some volatile organic compounds (VOCs) with low molecular weight were found as long-range attractants non-eliciting copulatory behavior. Since floral scents in Ophrys have been extensively studied by solvent extractions here we aimed to understand which flor…

Antifeedant activity of neo-clerodane diterpenoids from Teucrium arduini

Antibacterial and antifungal activities of Otanthus maritimus (L.) Hoffmanns.Link essential oil from Sicily.

The chemical composition of the essential oil obtained from the flowers of Otanthus maritimus L., a perennial plant growing wild in maritime sands in the Mediterranean region, was investigated by GC and GC-MS analyses. Totally 66 were identified. The oil was dominated by the high content of monoterpene compounds, especially oxygenated monoterpenes which accounted for 73.1%. The most abundant components were yomogi alcohol (20.8%), camphor (15.8%), artemisyl acetate (15.3%) and artemisia alcohol (13.7%). The oil was tested against two Gram (+) and six Gram (-) bacterial strains, both American Type Culture Collection standard strains and clinically isolated (CI), one potentially pathogenic ye…

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% …

Chemical composition of salvia argentea L. (laminaceae)

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…

In Vitro Modulation of P-Glycoprotein Activity by Euphorbia intisy Essential Oil on Acute Myeloid Leukemia Cell Line HL-60R

Euphorbia species have a large spectrum of traditional medicinal uses. We tested the biological activities of the essential oil (EO) of Euphorbia intisy Drake in an acquired multidrug resistance leukemia model to assess whether the EO obtained by hydrodistillation of stems was able to reverse the resistant phenotype. HL-60R cell lines are characterized by the overexpression of P-glycoprotein (P-gp), inhibitors of apoptosis proteins (IAPs) and constitutive expression of NF-κB. EO chemical composition was determined by GC/MS analysis

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…

Volatile components and antifeedant activity of the essential oil from Scutellaria hastifolia L.

ChemInform Abstract: Artalbic Acid, a Sesquiterpene with an Unusual Skeleton from Artemisia alba (Asteraceae) from Sicily.

Abstract From the aerial parts of Artemisia alba (Asteraceae) artalbic acid ( 1 ), a sesquiterpene with an unusual skeleton, was isolated. Its structure was elucidated on the basis of extensive proton, 13 C and two-dimensional NMR experiments, as well as by transformation in its methyl ester derivative.

Natural and hemisynthetic neoclerodane diterpenoids from Scutellaria and their antifeedant activityElectronic supplementary information (ESI) available: natural neoclerodanes from Scutellaria. See http://www.rsc.org/suppdata/np/b1/b111150g/

Covering: Up to June 2001. Previous review: on the clerodanes, Nat. Prod. Rep., 1992, 9, 243.

The Essential Oil of Thymbra capitata and its Application as A Biocide on Stone and Derived Surfaces

Many chemicals used nowadays for the preservation of cultural heritage pose a risk to both human health and the environment. Thus, it is desirable to find new and eco-friendly biocides that can replace the synthetic ones. In this regard, plant essential oils represent effective alternatives to synthetic substances for the preservation of historical monuments. Thymbra capitata (syn. Thymus capitatus) is a medicinal and aromatic plant growing in the Mediterranean area and endowed with important pharmacological properties related to its essential oil. Among them, the antimicrobial ones make the T. capitata essential oil an ideal candidate for industrial applications

Extremely potent antifeedant neo-clerodane derivatives of scutecyprol A

Two known neo-clerodane diterpenoids, scutecyprol A (1) and scutalbin C (2), have been isolated from the acetone extract of the aerial parts of Scutellaria sieberi. The antifeedant activity of scutecyprol A (1), of its 15-oxo derivative (3), and of several halohydrins (4-9), synthesized starting from compounds 1 and 3, against Spodoptera littoralis have been determined and structure-antifeedant relationships are discussed.

Scuteparvin, a new neoclerodane diterpenoid from Scutellaria parvula

Abstract The diterpenoid fraction occurring in the acetone extract of the aerial parts of Scutellaria parvula has been investigated. Only one neoclerodane diterpenoid, scuteparvin, was isolated and its structure elucidated as 4α,18-epoxy-6α- trans -cinnamoyloxy- neo clerod-13-en-15,16-olide, a new natural product. Scuteparvin is quite similar to the already known ajugarin V from Ajuga remota , the only difference being the occurrence of a trans -cinnamoyl ester system instead of an acetate on the 6α-OH group. This finding confirms that the genera Scutellaria and Ajuga are closely related taxonomically.

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.

Sesquiterpene lactones from Anthemis wiedemanniana

Asteraceae; Anthemis wiedemanniana; sesquiterpene lactones; germacranolides; eudesmanolide

Photochemical reactivity of 6α-hydroxy, 7-keto neoclerodane diterpenoids

Abstract The photochemical reactivity, in methanol at λ  = 254 nm, of two 6α-hydroxy-7-keto neoclerodane, isoeriocephalin ( 1 ) and teucrolivin B ( 2 ) was evaluated. From the first compound, two new products were obtained: the 6β-hydroxy epimer ( 3 ) and the ɛ-lactone ( 4 ). The second one yielded exclusively the new spiro γ-lactone ( 5 ). The formation of these new products can be explained by the well-known radical mechanism Norrish type I.

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

Composition of essential oil of lemon thyme (Thymus × citriodorus) at different hydrodistillation times.

Distillation time can both to optimise the production and to engineer the composition of essential oil in essential oil bearing plants. Purpose of this study was to evaluate the effect of duration of hydrodistillation on composition of essential oil of Thymus × citriodorus, the natural source of commercially important geraniol and citral, a component with valuable biological properties. Essential oils were isolated by hydrodistillation at different distillation times and analysed by GC/MS analytical methods. Increase in percentage of essential oil during all hydrodistillation time gradient was uneven. Elongation of hydrodistillation time decreased percentages of monoterpenes but increased p…

Assigning the C-15 configuration of 15-hydroxy-, 15-methoxy-, 15-ethoxy-hexahydrofurofuran neoclerodane diterpenoids

Abstract Examination of 1 H and 13 C NMR spectra allows the establishment of rules for assigning the correct configuration at C-15 of 15-hydroxy-, 15-methoxy-, 15-ethoxy-hexahydrofurofuran neoclerodane diterpenoids. The structure of several diterpenoids has been assigned or ammended.

Cytotoxicity of oleanolic and ursolic acid derivatives toward hepatocellular carcinoma and evaluation of NF-κB involvement.

Oleanolic and ursolic acids are two ubiquitous isomeric triterpene phytochemicals known for their anticancer activity. A set of derivatives of the two compounds with a modified oxidation state and lipophylicity at C-3 and C-28 positions, were prepared and tested as anticancer agents versus the lines HepG2, Hep3B and HA22T/VGH of hepatocarcinoma, a strongly aggressive tumor that is not responsive toward the standard therapies. New derivatives containing a three carbons side chain on the C-3 position were synthetized in both stereoisomeric forms by the Barbier-Grignard procedure and three of them were found to be active toward all of the three targets. The implication of the transcriptional n…

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.

Powerful tumor cell growth-inhibiting activity of a synthetic derivative of atractyligenin: Involvement of PI3K/Akt pathway and thioredoxin system

The semi-synthetic ent-kaurane 15-ketoatractyligenin methyl ester (SC2017) has been previously reported to possess high antiproliferative activity against several solid tumor-derived cell lines. Our study was aimed at investigating SC2017 tumor growth-inhibiting activity and the underlying mechanisms in Jurkat cells (T-cell leukemia) and xenograft tumor models. METHODS: Cell viability was evaluated by MTT assay. Cell cycle progression, reactive oxygen species (ROS) elevation and apoptotic hallmarks were monitored by flow cytometry. Inhibition of thioredoxin reductase (TrxR) by biochemical assays. Levels and/or activation status of signaling proteins were assessed by western blotting. Xenogr…

Composizione chimica degli olii essenziali di due nuove specie di Centaurea (Centaureinae, Asteraceae) della Sicilia

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 …

Flavonoids in sbtribe Centaureinae (Cass.) Dumort (tribe Carduae, Asteraceae): distibution and 13C spectral data

Asteraceae Bercht. & J. Presl is one of the biggest and most economically important plant families. The taxonomy and phylogeny of Asteraceae is rather complex and according to the latest and most reliable taxonomic classification of Panero & Funk, based on the analysis of nine chloroplast regions, the family is divided into 12 subfamilies and 35 tribes. One of the largest tribes of Asteraceae is Cardueae Cass. with four subtribes (Carlininae, Echinopinae, Carduinae and Centaureinae) and more than 2500 species. Susanna & Garcia-Jacas have organized the genera of Centaureinae (about 800 species) into seven informal groups, which recent molecular studies have confirmed: 1. Basal genera; 2. Vol…

Sesquiterpenes from Onopordum illyricum and their antifeedant activity

Phytochemical investigation of the acetone extract of the aerial parts of Onopordum illyricum L. afforded five known sesquiterpenoids: compounds 3 and 4 already isolated from O. illirycum, and 8α-[4′-hydroxymethacryloyloxy]-sonchucarpolide (1), 8α-[4′-hydroxymethacryloyloxy]-4-epi-sonchucarpolide (2) and 8-(4′-hydroxymethacryloyl)-dehydromelitensin (5), not previously detected in this species. Compounds 4 and 5 showed moderate antifeedant activity against larvae of Spodoptera littoralis.

Sesquiterpene lactones and other constituents of Centaurea paniculata ssp. castellana

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

Asteraceae Bercht. & J. Presl is one of the biggest and most economically important plant families. The taxonomy and phylogeny of Asteraceae is rather complex and according to the latest and most reliable taxonomic classification of Panero & Funk, based on the analysis of nine chloroplast regions, the family is divided into 12 subfamilies and 35 tribes. One of the largest tribes of Asteraceae is Cardueae Cass. with four subtribes (Carlininae, Echinopinae, Carduinae and Centaureinae) and more than 2500 species. Susanna & Garcia-Jacas have organized the genera of Centaureinae (about 800 species) into seven informal groups, which recent molecular studies have confirmed: 1. Basal genera; 2. Vol…

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 …

Chemodiversity of the Essential Oil from Leaves of Abies nebrodensis (Lojac.) Mattei

Abies nebrodensis (Lojac.) Mattei (Pinaceae) is a species occurring in a very small population only in a restricted area of Sicily. Its taxonomic classification as different species has been object of discussion. In this work the chemical composition of the essential oil from the leaves is presented for the first time and compared to the essential oils from other euroasiatic species reported in literature. Peculiar characteristics of the essential oil of A. nebrodensis are highlighted.

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.