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…
Bioactivity of Carlina acaulis essential oil and its main component to the olive fruit fly, Bactrocera oleae: ingestion toxicity, electrophysiological and behavioural insights
In recent years, botanical insecticides based on essential oils (EOs), or their main components, have received much attention as promising tools for Integrated Pest Management, due to their environmental safety and low side effects on non-target organisms. In this study, Carlina acaulis EO and its main component, carlina oxide, recently proven to be effective larvicidal and adulticidal agents against some insect pests, were analyzed for their toxicity, electroantennographic (EAG), and behavioral responses to adult olive fruit fly (Bactrocera oleae). The C. acaulis EO was more toxic to the tephritid than the carlina oxide, and both were more toxic to the same insect pest than EOs from other …
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…
Ferulago nodosa Subsp. geniculata (Guss.) Troia & 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…
Chemical Composition and Broad-Spectrum Insecticidal Activity of the Flower Essential Oil from an Ancient Sicilian Food Plant, Ridolfia segetum
Several species of the family Apiaceae are aromatic herbs that produce essential oils usable on an industrial scale for pharmaceutical, cosmetic, and food purposes. In particular, some essential oils, such as green insecticides for example, may replace synthetic insecticides, keeping most of their efficacy and avoiding environmental pollution or human poisoning. In the present study, we explored the insecticidal potential of Ridolfia segetum (L.) Moris essential oil (EO) against three different pests: Culex quinquefasciatus Say, Musca domestica L., and Spodoptera littoralis (Boisduval). For this purpose, the EO was obtained by hydrodistillation of flowers and its composition was achieved by…
Comparative HPLC/ESI-MS and HPLC/DAD study of different populations of cultivated, wild and commercial Gentiana lutea L.
The root of Gentiana lutea L., famous for its bitter properties, is often used in alcoholic bitter beverages, food products and traditional medicine to stimulate the appetite and improve digestion. This study presents a new, fast, and accurate HPLC method using HPLC/ESI-MS and HPLC/DAD for simultaneous analysis of iridoids (loganic acid), secoiridoids (gentiopicroside, sweroside, swertiamarin, amarogentin) and xanthones (isogentisin) in different populations of G.lutea L., cultivated in the Monti Sibillini National Park, obtained wild there, or purchased commercially. Comparison of HPLC/ESI-MS and HPLC/DAD indicated that HPLC/ESI-MS is more sensitive, reliable and selective. Analysis of twe…
Toxics or Lures? Biological and Behavioral Effects of Plant Essential Oils on Tephritidae Fruit Flies.
The family Tephritidae (Diptera) includes species that are highly invasive and harmful to crops. Due to globalization, international trade, and human displacement, their spread is continuously increasing. Unfortunately, the control of tephritid flies is still closely linked to the use of synthetic insecticides, which are responsible for detrimental effects on the environment and human health. Recently, research is looking for alternative and more eco-friendly tools to be adopted in Integrated Pest Management (IPM) programs. In this regard, essential oils (EOs) and their main compounds represent a promising alternative to chemical insecticides. EOs are made up of phytoconstituents formed fro…
Acaricidal Activity of Bufadienolides Isolated from Drimia pancration against Tetranychus urticae, and Structural Elucidation of Arenobufagin-3-O-α-L-rhamnopyranoside
Chemical characterization of the bulbs of Drimia pancration was conducted to isolate four steroidal saponins (1–4). Earlier, we focused on the structural elucidation of compounds 1–3. Herein, by means of 1H-NMR, 13C-NMR, Nuclear Overhauser Effects (NOE), and 2D-NMR spectra, the full stereochemical structure of 4 is reported, and all the 1H and 13C signals are assigned. Compounds 1–4 were tested for their acaricidal properties against the two-spotted spider mite Tetranychus urticae. Our results showed excellent activity of compound 1, with an LD50 (µg/cm2) of 0.29 and a LD90 (µg/cm2) of 0.96, whereas compounds 2, 3, and 4 showed moderate activity. Furthermore, t…
Larvicidal Activity of Essential Oils of Five Apiaceae Taxa and Some of Their Main Constituents Against Culex quinquefasciatus.
Apiaceae are aromatic herbs producing essential oils which are used on an industrial scale for various purposes. Notably, Apiaceae essential oils may replace synthetic insecticides keeping most of their efficacy and avoiding environmental pollution and human poisoning. In the present work, we explored the insecticidal potential of the essential oils from five Apiaceae taxa, namely Sison amomum, Echinophora spinosa, Heracleum sphondylium subsp. sphondylium, Heracleum sphondylium subsp. ternatum, and Trachyspemum ammi, as well as their major constituents (sabinene, p-cymene, terpinolene, myristicin, and thymol), against the filariasis vector Culex quinquefasciatus. For the purpose, the essent…
Lethal and behavioural effects of a green insecticide against an invasive polyphagous fruit fly pest and its safety to mammals
Abstract Plant essential oil-based insecticides, with special reference to those that may be obtained from largely available biomasses, represent a valuable tool for Integrated Pest Management. However, the sublethal effects and the potential effects on aggressive insect traits of these green insecticides are understudied. Herein, the lethal and sub-lethal effects of the carlina oxide, constituting more than 97% of the whole Carlina acaulis (Asteraceae) root essential oil (EO), were determined against an invasive polyphagous tephritid pest, Ceratitis capitata (medfly). The carlina oxide was formulated in a mucilaginous solution containing carboxymethylcellulose sodium salt, sucrose, and hyd…
Chemical composition of the essential oil of Elaeoselinum asclepium (L.) Bertol subsp. meoides (Desf.) Fiori (Umbelliferae) collected wild in Central Sicily and its antimicrobial activity
In the present study, the chemical composition of the essential oils from flowers and leaves of Elaeoselinum asclepium(L.) Bertol subsp. meoides(Desf.) Fiori collected in Central Sicily was evaluated by GC and GC-MS. The main volatile components of the flowers were alpha-phellandrene (42.5%), terpinolene (15.7%), p-cymene (11.6%) and beta-phellandrene (10.2%), whereas the ones of the leaves were p-cymene (44.0%), alpha-pinene (13.2%), alpha-phellandrene (11.0%), beta-phellandrene (10.2%) and beta-pinene (9.2%). Furthermore, the antibacterial and antifungal activities against some microorganisms infesting historical art craft were determined. The essential oil from leaves (EL) showed to be p…
The Nonvolatile and Volatile Metabolites of Prangos ferulacea and Their Biological Properties
Abstract Prangos ferulacea (L.) Lindl. (Fam. Apiaceae), an orophilous species of eastern Mediterranean and western Asia, possesses a number of biological properties that are worthy of exploitation in different fields. Phytochemical investigations revealed the presence of coumarins, prenyl-coumarins, and furano-coumarins as the main constituents of this species, as well as several flavonoids. Among prenyl-coumarins, osthol is a promising apoptotic agent quite selective toward cancer cells. In addition, the essential oils have been extensively investigated, and several chemotypes have been identified. This work reviews the literature on this species published between 1965 and 2018, describes …
Efficacy of sea fennel (Crithmum maritimum L., Apiaceae) essential oils against Culex quinquefasciatus Say and Spodoptera littoralis (Boisd.)
The effective management of insect pests and vectors still represents a major challenge in current entomology. Culex quinquefasciatus Say is a key vector of lymphatic filariasis, Rift Valley fever, West Nile, St. Louis encephalitis and Western equine encephalitis virus. Recently, the importance of the eco-friendly control of C. quinquefasciatus larval population using plant-borne biopesticides, including essential oils (EOs), has been stressed. Spodoptera littoralis (Boisd.) also known as tobacco cutworm, is one of the most destructive moth agricultural pests in tropic and sub-tropic regions. Despite the fact that sea fennel (Crithmum maritimum L., Apiaceae) is considered as a promising bio…
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…
Composition and biological activities of the essential oil from a Sicilian accession of Prangos ferulacea (L.) Lindl
Prangos ferulacea (L.) Lindl. (Fam. Apiaceae), is an orophilous species of eastern Mediterranean and western Asia which possesses several biological properties, which are worthy of exploitation in different fields. With the aim to provide new insights into the phytochemistry and pharmacology of this species, a local accession growing in Sicily (South Italy) was investigated as well. Notably, the P. ferulacea essential oil chemical composition and the antioxidant, anti-acetylcholinesterase (AChE) and cytotoxic activities have been studied. This analysis allowed to identify a new chemotype and to report good biological results for this oil. © 2019 Informa UK Limited, trading as Taylor & F…
The chemical composition of the aerial parts essential oil of Acinos alpinus subsp. nebrodensis (Lamiaceae) growing in Sicily (Italy)
Acinos is a small genus of economically important plants belonging to Lamiaceae family whose botanical collocation is quite problematic due to the disagreement among the botanists and the presence in literature of several names and synonyms from different sources. In the present study the chemical composition of the essential oil from aerial parts of Acinos alpinus subsp. nebrodensis (Strobl) Brullo & Brullo collected in Central Sicily was analyzed by GC-MS. The result showed the presence of large quantity of sesquiterpene hydrocarbons with germacrene D (37.9%) as the most abundant component followed by (E)-β-caryophyllene (5.1%). Among the oxygenated monoterpenes thymol (8.3%) was the …
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.
Carlina acaulis and Trachyspermum ammi essential oils formulated in protein baits are highly toxic and reduce aggressiveness in the medfly, Ceratitis capitata
Abstract Essential oil (EO)-based botanical insecticides are considered a promising option for Integrated Pest Management (IPM). However, the sublethal effects of EO-based insecticides are understudied. No information is available on the potential effects of EO exposure on insect aggressive traits. In this study, the toxicity of two EOs with documented efficacy on insect vectors and agricultural pests, and which were obtained from the roots of silver thistle (Carlina acaulis L., Asteraceae) and seeds (i.e. schizocarps) of ajwain (Trachyspermum ammi (L.) Sprague, Apiaceae), was evaluated against adults of the Mediterranean fruit fly, Ceratitis capitata (Wiedemann) (medfly), a cosmopolitan fr…
Chemical composition, antioxidant and anticholinesterase activity of the essential oil of algerian cachrys sicula L
In this work, in order to explore a new Algerian medicinal plant used in traditional medicine, the essential oil of the leaves of Cachrys sicula L. (Apiaceae) collected from Algeria, obtained by hydrodistillation, was analyzed by GC/MS. Thirty-two compounds were identified accounting for 98.6% of the total oil, which is characterized by a high content of monoterpene hydrocarbons (74.8%). The main constituents of the essential oil were β-pinene (17.9%), sabinene (17.8%), myrcene (12%), and α-pinene (11.4%). In vitro antioxidant activity of the essential oil was assayed by three methods, namely ABTS•+, metal chelating, and DPPH• assays. The antioxidant activity of the oil was higher in the AB…
Identification of highly effective antitrypanosomal compounds in essential oils from the Apiaceae family
The Apiaceae family encompasses aromatic plants of economic importance employed in foodstuffs, beverages, perfumery, pharmaceuticals and cosmetics. Apiaceae are rich sources of essential oils because of the wealth of secretory structures (ducts and vittae) they are endowed with. The Apiaceae essential oils are available on an industrial level because of the wide cultivation and disposability of the bulky material from which they are extracted as well as their relatively cheap price. In the fight against protozoal infections, essential oils may represent new therapeutic options. In the present work, we focused on a panel of nine Apiaceae species (Siler montamon, Sison amomum, Echinophora spi…
Anti-Pseudomonas aeruginosa activity of hemlock (Conium maculatum, Apiaceae) essential oil
Conium maculatum is a nitrophilous weed belonging to the Apiaceae family and occurring in hedgerows, pastures, waste ground, along rivers and roadsides. Little is known on the chemistry and bioactivity of other secondary metabolites occurring in the plant. In the present work, we have analysed the chemical composition and antimicrobial activity of the essential oils hydrodistilled from leaves and inflorescenes of C. maculatum growing in Sicily, Italy. The composition of essential oils was achieved by gas chromatography-mass spectrometry (GC-MS) analysis, whereas the inhibitory effects on the growth of two Gram negative strains, namely Escherichia coli and Pseudomonas aeruginosa were assesse…
Essential oils from three Algerian medicinal plants (Artemisia campestris, Pulicaria arabica, and Saccocalyx satureioides) as new botanical insecticides?
Medicinal and aromatic plants represent an outstanding source of green active ingredients for a broad range of real-world applications. In the present study, we investigated the insecticidal potential of the essential oils obtained from three medicinal and aromatic plants of economic importance in Algeria, Artemisia campestris, Pulicaria arabica, and Saccocalyx satureioides. Gas chromatography coupled with mass spectrometry (GC-MS) was used to study the essential oil chemical compositions. The three essential oils were tested against a mosquito vectoring filariasis and arboviruses, i.e., Culex quinquefasciatus, a fly pest acting also as pathogens vector, Musca domestica, and an agricultural…
Determination of soyasaponins I and βg in raw and cooked legumes by solid phase extraction (SPE) coupled to liquid chromatography (LC)-mass spectrometry (MS) and assessment of their bioaccessibility by an in vitro digestion model.
Legumes contain a rich variety of phytochemicals as soyasaponins, triterpenoidal glycosides that possess multiple health-promoting properties, such as lowering of cholesterol. In this work, the quantification of soyasaponins I and βg in 60 raw and cooked legumes by using a solid phase extraction (SPE) coupled to a liquid chromatography (LC)-mass spectrometry (MS) method was carried out. Results showed that lentils are a good source of soyasaponins, with a content of soyasaponin I that ranged from 636 to 735 mg kg(-1) and of soyasaponin βg from 672 to 1807 mg kg(-1). The cooking process produced a small loss of soyasaponins in water, that is, 4.8-8.7%, and partially converted soyasaponin βg …
Developing green insecticides to manage olive fruit flies? Ingestion toxicity of four essential oils in protein baits on Bactrocera oleae
Abstract Effective and eco-friendly plant-borne insecticides for developing lure and kill control tools against tephritid flies are scarce. Herein, the activity of four essential oils (EOs) obtained from two Apiaceae, Pimpinella anisum L. and Trachyspermum ammi (L.) Sprague, and two Lamiaceae, Thymbra spicata L. and Ocimum gratissimum L., was evaluated against the olive fruit fly, Bactrocera oleae (Rossi), a key pest of olive groves. The EO chemical composition was determined by gas chromatography coupled with mass spectrometry (GC-MS) analyses. The four EOs incorporated in protein baits were tested for ingestion toxicity on B. oleae adults, mimicking lure and kill assays. Results showed con…
Hairy Garlic (Allium subhirsutum) from Sicily (Italy): LC-DAD-MSn Analysis of Secondary Metabolites and In Vitro Biological Properties
Allium subhirsutum, known as hairy garlic, is a bulbous plant widespread in the Mediterranean area and locally used as a food and spice. In the present study, the chemical profile of the ethanolic extracts from bulbs (BE) and aerial parts (APE) were analyzed by HPLC-ESI-MSn, and antioxidant properties were evaluated by DPPH, ABTS and TEAC assays. The traditional use in the diet, and the well documented biological activity of Allium species suggest a potential as a new nutraceutical. For this reason, the potential usefulness of this food can be considered in the treatment and prevention of degenerative Alzheimer disease. For this reason, acetylcholinesterase inhibitory property was investiga…
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
Kundmannia sicula (L.) DC: a rich source of germacrene D
AbstractObjective: Kundmannia sicula is an herbaceous plant belonging to the family Apiaceae and is distributed in the Mediterranean coastal areas where it occurs in arid places. In this work, we have analysed the essential oil distilled from the aerial parts of K. sicula from Sicily (Italy) and its biological activity. Methods: GC-MS was used to analyze the chemical composition, whereas its antioxidant capacity and cytotoxicity on three human tumour cells (A375, MDA MB-231 and HCT 116) were evaluated by DPPH, ABTS, FRAP and MTT methods, respectively. Result: The essential oil resulted very rich of the sesquiterpene hydrocarbon germacrene D (81.2%). Moreover, the K. sicula oil displayed rel…
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…