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.

Essential oil of Foeniculum vulgare subsp. piperitum fruits exerts an anti‑tumor effect in triple‑negative breast cancer cells

At present, the growing spread of tumor cases worldwide renders the research of new promising and selective anticancer drugs urgent. The biological action of extracts of medicinal plants or their essential oils (EOs) is an emerging field of interest, since they could comprise a rich source of phytochemicals that can prove promising. In the present study, the biological activity and mechanism of action of the EO of Foeniculum vulgare subsp. piperitum fruits (FVPEO) were investigated using MTT assays, morphological analyses and western blotting in MDA‑MB231 cells, a triple‑negative breast cancer cell line. The findings revealed that FVPEO could exert strong anticancer effects, causing a dose‑…

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…

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.

Medicinal and aromatic plants in agricultural research, when considering criteria of multifunctionality and sustainability

Over the last twenty years, agriculture has witnessed significant changes in terms of energy requirements, advanced technologies and practices. This is in response to the impacts of crop production on the climate and environment and increasing awareness of the importance of agricultural sustainability through organic farming. Agriculture encompasses complex production systems and certain aspects of multifunctionality and sustainability have become fundamental for these systems. Agricultural activity can provide various functions in agro-ecosystems, such as producing food, managing natural resources, and conserving landscape and plant biodiversity; contributing to the cultural, historical an…

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.

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

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

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.

Antibacterial activity and HPLC analysis of extracts from Mediterranean brown algae

The antibacterial activity of methanolic extracts of eight Mediterranean brown algae belonging to the genera Cystoseira sensu lato, Dictyopteris and Padina was investigated. Extracts from Sargassaceae showed antibacterial activity. Specifically, Carpodesmia crinita and Carpodesmia brachycarpa extracts inhibited the growth of the Gram-positive strain Kocuria rhizophila whereas Cystoseira compressa and Carpodesmia amentacea extracts showed antibacterial activity against the Gram-positive strains, Kocuria rhizophila and Staphylococcus aureus. None of them inhibited the growth of the Gram-negative bacterium Escherichia coli. The extracts of Cystoseira sp. pl. and Treptacantha ballesterosii did …

Flavouring Extra-Virgin Olive Oil with Aromatic and Medicinal Plants Essential Oils Stabilizes Oleic Acid Composition during Photo-Oxidative Stress

Essential oils (EOs) from medicinal and aromatic plants (MAPs) are well-known as natural antioxidants. Their addition to extra-virgin olive oil (EVOO) can contribute to reducing fat oxidation. The main aim of this study was to improve both food shelf-life and aromatic flavour of EVOO, adding different EOs of Sicilian accessions of common sage, oregano, rosemary and thyme. The morphological and production characteristics of 40 accessions of MAPs were preliminarily assessed. EOs from the most promising accessions of MAPs were analysed by gas-chromatography and mass spectrometry. Photo-oxidative studies of the EOs were carried out and the determination of the EVOO fatty acids obtained from 4 I…

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.

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

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

Technological screening and application of Saccharomyces cerevisiae strains isolated from fermented honey by-products for the sensory improvement of Spiritu re fascitrari, a typical Sicilian distilled beverage

“Spiritu re fascitrari” is a Sicilian alcoholic beverage obtained through distillation of a decoction of spontaneously fermented honey by-products (FHP). The production process often leads to sensorial defects due to the unstable alcoholic fermentation. The objective of this work was to select Saccharomyces cerevisiae strains from FHP to be used as starter in decoction fermentation. Based on chemical, microbiological and technological data, from a total of 91 strains three S. cerevisae were selected for further testing to produce FHP at laboratory scale level. After FHP distillation, the analysis of volatile organic compounds showed a complex mixture of sensory active molecules, mainly alco…

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.

Metabolite and mineral profiling of “Violetto di Niscemi” and “Spinoso di Menfi” globe artichokes by 1H-NMR and ICP-MS

Globe artichoke has been long considered a nutraceutical food for its valuable content of bioactive compounds. However, beside a well-known polyphenol profile, poor information is available about its metabolite and mineral composition. The aim of this study was to investigate edible parts of Sicilian artichokes, ‘Spinoso di Menfi’ and ‘Violetto di Niscemi’, by 1H NMR and ICP-MS for elucidating these compositional aspects. Although bracts and hearts of both artichokes shared a very similar metabolite pattern, ‘Spinoso di Menfi’ showed a higher number of metabolites, such as amino acids and polyphenols, than ‘Violetto di Niscemi’. ‘Spinoso di Menfi’ was also marked by higher levels of macro- …

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…

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.

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%…

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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…

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.

Effects of different yeast strains, nutrients and glutathione-rich inactivated yeast addition on the aroma characteristics of Catarratto wines

Catarratto is one of the most common non-aromatic white grape varieties cultivated in Sicily (Southern Italy). In order to improve the aromatic expression of Catarratto wines a trial was undertaken to investigate the effect of yeast strain, nutrition and reduced glutathione. Variables included two Saccharomyces cerevisiae strains, an oenological strain (GR1) and one isolated from honey by-products (SPF52), three different nutrition regimes (Stimula Sauvignon Blanc™ (SS), Stimula Chardonnay™ (SC) and classic nutrition practice), and a specific inactivated yeast rich in reduced glutathione to prevent oxidative processes [Glutastar™ (GIY)] ensuing in ten treatments (T1-T10). Microbiological an…

Low mimosine content and nutrient-rich foliage of two Leucaena leucocephala varieties: a potential fodder resource in Mediterranean agroforestry systems

Leucaena leucocephala is worldwide used for wood production, reforestation and for feeding livestock. To assess the potential use of leucaena for animal nutrition, we analysed the composition of methanolic extracts of leaf samples of two varieties occurring in Sicily (Mediterranean area), also determining the presence of mimosine.

The Anti-Cancer Effect of Mangifera indica L. Peel Extract is Associated to γH2AX-mediated Apoptosis in Colon Cancer Cells

Ethanolic extracts from Mangifera indica L. have been proved to possess anti-tumor properties in many cancer systems. However, although most effects have been demonstrated with fruit pulp extract, the underlying molecular mechanisms of mango peel are still unclear. This study was designed to explore the effects of mango peel extract (MPE) on colon cancer cell lines. MPE affected cell viability and inhibited the colony formation trend of tumor cells, while no effects were observed in human dermal fibroblasts used as a non-cancerous cell line model. These events were a consequence of the induction of apoptosis associated to reactive oxygen species (ROS) production, activation of players of th…

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.

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.

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.

Sesquiterpene lactones from Anthemis plutonia.

Abstract Aerial parts of Anthemis plutonia furnished three guaianolides, one of them new.

Essential oil variability in a collection of Ocimum basilicum L. (basil) cultivars.

Ocimum basilicum L. (Lamiaceae) is an aromatic plant of great tradition in the Mediterranean area. Its economic importance is growing up determining an expansion of cultivation. This paper evaluated the morphological traits, the chemical profiles, and antibacterial activity of 21 cultivars of basil belonging to Ê»Genoveseʼ, Ê»Napoletanoʼ, and Ê»Purple basilʼ types. The cultivars were characterized by different growth rate and morphological traits. The chemical composition of the oils analyzed by GC and GC/MS analysis, supported by the PCA analysis, underlined the strong influence of chemotype. It is noteworthy that estragole, never present in Genovese and purple basil types, occurred in …

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.

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.

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.

Influence of indigenous Hanseniaspora uvarum and Saccharomyces cerevisiae from sugar-rich substrates on the aromatic composition of loquat beer

The demand for unique and exclusive food products and beverages is constantly on the increase. One of the products that mostly evolved to encounter market dynamics in the last decade is craft beer. For a long time, craft breweries have included fruit in beer production to enrich flavour and aroma profile of different beer styles. In this study, for the first time, the use of Saccharomyces and non-Saccharomyces yeast strains isolated from high -sugar matrices (manna and fermented honey by-products) were investigated to diversify fruit craft beer pro-duction, in order to improve the fermentation process and highlight the complexity of aroma profiles generated during alcoholic fermentation. Tw…

Improving the Aromatic Profiles of Catarratto Wines: Impact of Metschnikowia pulcherrima and Glutathione-Rich Inactivated Yeasts

Catarratto is one of the most widely cultivated grape varieties in Sicily. It is an indigenous non-aromatic white grape variety. Despite its widespread use in winemaking, knowledge of the aroma and chemical and microbiological properties of Catarratto wines is quite limited. The influence of Metschnikowia pulcherrima combined with Saccharomyces cerevisiae on the aromatic expression of Catarratto wines was investigated with and without the addition of glutathione-rich inactivated yeast. The substance is a natural specific inactivated yeast with a guaranteed glutathione level used to limit oxidative processes. The aromatic profiles of the final wines were determined through analysis of the vo…

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

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

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…

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 …

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

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

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.

Use of sequentially inoculation of Saccharomyces cerevisiae and Hanseniaspora uvarum strains isolated from honey by-products to improve and stabilize the quality of mead produced in Sicily

Mead is a beverage produced by alcoholic fermentation of honey-must. The starter yeasts that are commonly used for the alcoholic fermentation of honey-must are oenological Saccharomyces cerevisiae strains. The objective of the present work was, for the first time, to apply yeasts of honey by-products origin to evaluate the influences the taste-olfactory attributes of mead. For this purpose, three experimental productions were set up, which included: (i) single inoculation of S. cerevisiae; (ii) single inoculation of Hanseniaspora uvarum; (iii) sequential inoculation of H. uvarum/S. cerevisiae. Two control trials were performed, using a commercial strain of S. cerevisiae of oenological origi…

Guaianolides from Centaurea babylonica

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.

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

Ferulago nodosa (L.) Boiss. (Apiaceae) is a species occurring in the Balkan-Tyrrhenian area being present in Crete, Greece, Albania, and probably in Macedonia. From the roots of this accession of species, not previously investigated, four coumarins, grandivittin, aegelinol benzoate, felamidin and aegelinol, and two terpenoids, (2E)-3-methyl-4-[(3-methyl-1-oxo-2-buten-1yl)oxy]-2-butenoic acid and pressafonin-A, were isolated and spectroscopically characterized. The last one was never detected in Ferulago species. The evaluation of the anti-tumor effects of F. nodosa coumarins on colon cancer HCT116 cells showed only a modest effect on reduction of tumor cell viability. For aegelinol, the red…

Agronomic, metabolomic and lipidomic characterization of Sicilian Origanum vulgare (L.) ecotypes

Although Origanum vulgare (L.) has been deeply analysed at phytochemical level, poor knowledge is available regarding non-volatile compounds such as lipids. The aim of this work was to characterise five wild Sicilian Origanum ecotypes from an agronomic, metabolomic and lipidomic perspective. Serradifalco presented higher dry weight and inflorescences/plant than the others while Favara had a significantly higher number of branches per plant and more extensive flowered stratum. Metabolomic analysis, performed with LC-MS-TOF, allowed a preliminary characterisation of the non-volatile metabolome of the five oregano ecotypes Origanum vulgare ssp. hirtum. Twenty-five metabolites were identified b…

Comparative chemical composition and bioactivity of leaves essential oils from nine Sicilian accessions of Myrtus communis L.

In this study, the essential oils obtained from the leaves of Myrtus communis L. stored in a collection orchard located at the experimental station ‘Orleans’ of the Department of Agricultural and Forest Sciences of the University of Palermo (Italy) were investigated. The essential oils, analysed by gas chromatography–mass spectrometry, revealed the presence of α-pinene, 1,8-cineole, linalool, limonene and myrtenyl acetate as dominant constituents. The neuroprotective effects of M. communis essential oils were investigated by analysing the antioxidant properties and cholinesterases (acetylcholinesterase, AChE, and butyrylcholinesterase, BChE) inhibitory activity. Essential oils from Scopello…

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 …

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

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.

Chemical composition, antimicrobial and antioxidant activity of the essential oils from Pimpinellatragium Vill. subsp. glauca (C. Presl.) C. BrulloBrullo (Apiaceae) growing wild in Sicily.

The essential oils from flowers, leaves and stems hydrodistilled from Pimpinella tragium Vill, subsp. glauca were characterised by GC and gas chromatography-mass spectrometry analysis. The C-12 nor-sesquiterpenes are the principal class of metabolites (56.6-70.6%) among which geijerene (28.9÷49.3%) and pregeijerene (10÷19.1%) predominate. Antimicrobial and antioxidant activities were evaluated. The minimum inhibitory concentration values indicate that oil obtained from the stems is the most active for antimicrobial activities and the sample with the biggest antioxidant capacity is the flower oil.

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 of the essential oil of Centaurea grinensis Reuter and Centaurea apiculata Ledeb: Growing wild in Croatia and Bulgaria, respectively and PCA analysis of subgenus Lopholoma (Cass.) Dobrocz

AbstractIn the present study, the chemical composition of the essential oils from aerial parts of Centaurea grinensis Reuter (K) collected at Žuta Lova, near Senj (Croatia), and aerial parts (L1) and flowers (L2) of C. apiculata Ledeb. collected near Rebro village, near Breznik town, Znepole Region (Bulgaria), both belonging to subgenus Lopholoma (Cass.) Dobrocz, was evaluated by GC and GC-MS. The main components of K were 4-vinyl guaiacol (21.5%), hexadecanoic acid (16.2%), acetophenone (12.5%). Caryophyllene oxide (15.8%) together with sphathulenol (14.5%) and humulene epoxide II (9.4%) were recognized as the main constituent of both the aerial part (L1) and flowers (L2) of C. apiculata. …

Chemical Composition of the Essential Oil of Teucrium flavum ssp. flavum from Zakynthos, Greece

Essential oil extracted from dried aerial parts of Teucrium flavum ssp. flavum harvested in Zakynthos, Greece, was analysed by gas phase chomatography (GC) and gas chomatography mass spectrometry (GC-MS). The main constituents were caryophyllene (13.5%), caryophyllene oxide (8.5%), 4-vinyl guaiacol (6.0%) and α- humulene (5.0%).

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 …

Volatile constituents of aerial parts of Lasiopogon muscoides

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.

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)

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.

The diterpenoids of the genus Marrubium (Lamiaceae)

Chemical composition and antimicrobial activity of the essential oils of some species of Anthemis sect. Anthemis (Asteraceae) from Sicily

The chemical composition of the essential oils isolated from the aerial parts of Anthemis arvensis L. subsp. arvensis, Anthemis cretica subsp. messanensis (Brullo) Giardina & Raimondo and from flowers and leaves of Anthemis cretica subsp. columnae (Ten.) Frezén were determinated by GC–FID and GC–MS analyses. Torreyol (85.4%) was recognised as the main constituent of the Anthemis arvensis subsp. arvensis essential oil, while in the essential oils of Anthemis cretica subsp. messanensis, collected on the rock and cultivated in Hortus Botanicus Panormitanus, (E)-chrysanthenyl acetate (28.8 and 24.2% resp.), 14-hydroxy-α-humulene (8.1 and 5.3% resp.), santolina triene (8 and 5.8% resp.) and …

Labdane Diterpenes from Stachys plumosa

Three new labdane diterpenoids were isolated from the aerial parts of Stachys plumosa. The first two (1, 2) were the dextrorotatory enantiomers of the known 6-deoxyandalusol and 13-epijabugodiol. Structures were determined using NMR and MS techniques. The absolute stereochemistry of the third compound (3) was not experimentally proved.

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 the local endemics Centaurea davidovii and C. parilica (Asteraceae, sect. Lepteranthus) from Bulgaria

In the present study the chemical compositions of the essential oils from aerial parts of Centaurea davidovii Urum. and C. parilica Stoj. & Stef., both endemic to Bulgaria, were evaluated by GC and GC-MS. The main components of C. davidovii were β-eudesmol (13.9%), spathulenol (13.3%), caryophyllene oxide (10.1%) and ( Z)-phytol (5.4%). The main components of C parilica were hexadecanoic acid (39.2%), ( Z, Z)-9,12-octadecadienoic acid (11.9%), caryophyllene oxide (6.8%) and spathulenol (6.6%). In order to compare the essential oils composition of these taxa and of related species a PCA analysis was carried out.

Reuse of almond by-products: Functionalization of traditional semolina sourdough bread with almond skin

Almond production generates large amounts of by-products rich in polyphenols. In this study, almond skin was explored as a valuable food ingredient in bread making. To this purpose, almond skin was used to produce functional products modifying a traditional sourdough bread recipe. The doughs were prepared replacing semolina with powdered almond skin (PAS) at 5 and 10 % (w/w). Sourdough inoculum was started with a mix of lactic acid bacteria (LAB) and propagated in semolina until reaching pH 3.7. The pH of PAS added breads was higher than that of control (CTR) breads before and after fermentation. Plate counts showed a similar evolution of LAB and total mesophilic microorganisms, but members…

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)

Polyphenols pattern and correlation with antioxidant activities of berries extracts from four different populations of SicilianSambucus nigraL.

Sambucus nigra L. (Caprifoliaceae) is wide spread in temperate and sub-tropical zones. The consumption of its berries has been associated with health benefits especially for its high content of natural antioxidants such as polyphenols, in particular anthocyanins. In this work we investigated the polyphenolic composition and the in vitro antioxidant activities (ABTS, DPPH, BCB and FRAP-ferrozine (FRAP-FZ) assays) of S. nigra berries, collected in four different Sicilian areas (Italy). Elderberries are considered one of the fruits with highest anthocyanins content, the amount of phenolic compounds, other than anthocyanins, is approximately 1.5 times greater than the latter. The LC–MS analyses…

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.

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

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

Fatty Acid Composition of Gluten-Free Food (Bakery Products) for Celiac People

The aim of this study (first analytical approach) was to obtain data concerning the fatty acid composition of gluten-free foods (bakery products) for celiac people. The study included 35 different products (snacks, biscuits, bakery products, pasta, flours, etc.) from several manufacturers. After extraction and esterification, the fatty acid composition was determined by Gaschromatography (GC&ndash

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

WOS: 000306752700042

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.

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

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

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.

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

Antifeedant activity of neoclerodane diterpenoids from two Sicilian species of Scutellaria

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

The volatile constituents of the flowers of Caralluma (Apteranthes) europaea (Guss.) N.E. Br. (Apocynaceae - Asclepiadoideae) from Lampedusa Island were analyzed by headspace method. The analyses allowed the identification and quantification of 41 compounds. The main components were, among the monoterpenoids, terpinolene (23.3%), a-terpinene (19.1%) and linalool (18.4%), whereas, among the carbonylic compounds the major constituents were heptanal (2.0%), octanoic acid (2.4%) and hexanoic acid (1.7%). It is worth to mention the presence of a nitrogen containing compound, indole (0.8%) and of a sulphur containing compound, dimethylsulphide (t). The compounds found in the flowers of C. europea…

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

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

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

The chemical composition of the essential oils isolated from the aerial parts of Anthemis pignattiorum Guarino, Raimondo & Domina and A. ismelia Lojac. and the aerial parts and flowers of Anthemis cupaniana Tod. ex Nyman , three endemic Sicilian species belonging to the section Hiorthia, was determined by GC-FID and GC/MS analyses. (Z)-Muurola-4(14),5-diene (27.3%) was recognized as the main constituent of the A. pignattiorum essential oil, together with isospathulenol (10.6%), sabinene (7.7%), and artemisyl acetate (6.8%), while in the oil obtained from the aerial parts of A. ismelia , geranyl propionate (8.8%), bornyl acetate (7.9%), β-thujone (7.8%), neryl propionate (6.5%), and t-muurol…

An integrated proteomic and metabolomic study to evaluate the effect of nucleus-cytoplasm interaction in a diploid citrus cybrid between sweet orange and lemon.

Key message: Our results provide a comprehensive overview how the alloplasmic condition might lead to a significant improvement in citrus plant breeding, developing varieties more adaptable to a wide range of conditions. Abstract: Citrus cybrids resulting from somatic hybridization hold great potential in plant improvement. They represent effective products resulting from the transfer of organelle-encoded traits into cultivated varieties. In these cases, the plant coordinated array of physiological, biochemical, and molecular functions remains the result of integration among different signals, which derive from the compartmentalized genomes of nucleus, plastids and mitochondria. To dissect …

Sicilian Litchi Fruit Extracts Induce Autophagy versus Apoptosis Switch in Human Colon Cancer Cells

Litchi chinensis Sonnerat is a tropical tree whose fruits contain significant amounts of bioactive polyphenols. Litchi cultivation has recently spread in Sicily where the climate conditions are particularly favorable for this crop. Recent findings have shown that Litchi extracts display anti-tumor and pro-apoptotic effects in vitro, but the precise underlying mechanisms have not been fully elucidated. In this study, we report for the first time the effects of Sicilian litchi fruit extracts on colon cancer cells. The results indicated that litchi exocarp, mesocarp and endocarp fractions reduce the viability and clonogenic growth of HT29 cells. These effects were due to cell cycle arrest in t…

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.

Chemical Composition and Free Radical Scavenging Activity of the Essential Oil of Achillea ligustica Growing Wild in Lipari (Aeolian Islands, Sicily)

In the present study the chemical composition of the essential oils from aerial parts and flowers of Achillea ligustica All., collected in Lipari (Aeolian Islands) was evaluated by GC and GC-MS. ( Z)-Chrysanthenyl acetate was the most abundant component of both oils (29.6% in A1 and 27.8% in F1), followed by viridiflorol (16.8% in A1 and 21.6% in F1), bornyl acetate (8.7% in A1 and 11.6% in F1) and 1,8-cineole (7.4% in A1 and 9.3% in F1). A comparison was made of the composition of the different populations studied so far. Futhermore, the free radical scavenging activity of the oil was determined by DPPH and ABTS methods.

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

Bio-Waste Products of Mangifera indica L. Reduce Adipogenesis and Exert Antioxidant Effects on 3T3-L1 Cells

Several studies highlighted the beneficial value of natural compounds in the prevention and treatment of obesity. Here, we investigated the anti-obesity effects of extracts of peel and seed of mango (Mangifera indica L.) cultivated in Sicily (Italy) in 3T3-L1 cells. Mango Peel (MPE) and Mango Seed (MSE) extracts at a 100 µg/mL concentration significantly reduced lipid accumulation and triacylglycerol contents during 3T3-L1 adipocyte differentiation without toxicity. HPLC-ESI-MS analysis showed that both the extracts contain some polyphenolic compounds that can account for the observed biological effects. The anti-adipogenic effect of MPE and MSE was the result of down-regulation of th…

Cytotoxic activity of several ent-kaurane derivatives of atractyligenin. Synthesis of unreported diterpenic skeleton by chemical rearrangement

Atractyloside, carboxyatractyloside, their aglycon atractyligenin, and several synthetic derivatives were tested and found to be active against a panel of human tumor cell lines. Atractyligenin was subjected to oxidation, bromination, and elimination reactions, obtaining several compounds. A singular skeleton was synthesized by chemical rearrangement starting from 3 beta-bromo-2,15-diketoatractyligenin methyl ester. The synthesized compounds resulted active against all cell lines tested. In particular, 15-ketoatractyligenin methyl ester and 3 beta bromo-2,15-diketoatractyligenin methyl ester resulted the most active with IC50 values of 0.427 and 0.723 mu M against A375 melanoma cell line. E…

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.

Development of "Quadrello di Ovino", a Novel Fresh Ewe's Cheese.

This work was performed to produce a new soft ewe’s milk cheese, namely “Quadrello di ovino” (QdO) cheese, to enlarge ewe’s dairy product portfolio of South Italy, barely limited to Pecorino cheese typology. Cheese making was performed applying the technology for “Crescenza” cheese typology with some modifications. In particular, pasteurized ewes’ milk was inoculated with two commercial starter formulations (SF1 and SF2) of Streptococcus thermophilus to obtain two different productions (QdO-P1 and QdO-P2, respectively). Plate counts demonstrated the ability of both starter formulations to drive the fermentation process, since S. thermophilus counts reached 109 CFU/g in both productions. Gen…

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.

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 …

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.