Chemical Profile and Healthy Properties of Sicilian Diplotaxis harra subsp. crassifolia (Raf.) Maire.

This study was aimed at investigating the phytochemical profile and bioactivity of Diplotaxis harra subsp. crassifolia (Brassicaceae), a species from central-southern Sicily (Italy), where it is consumed as a salad. For this purpose, LC-ESI/HRMSn analysis of the ethanolic extract was performed, highlighting the occurrence, along with flavonoids, hydroxycinnamic acid derivatives, and oxylipins, of sulfated secondary metabolites, including glucosinolates and various sulfooxy derivatives (e.g., C13 nor-isoprenoids, hydroxyphenyl, and hydroxybenzoic acid derivatives), most of which were never reported before in the Brassicaeae family or in the Diplotaxis genus. Following ethnomedicinal information regarding this species used for the treatment of various pathologies such as diabetes and hypercholesterolemia, D. harra ethanolic extract was evaluated for its antioxidant potential using different in vitro tests such as 2,2-diphenyl-1-picrylhydrazyl, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), Ferric Reducing Ability Power, and ß-carotene bleaching tests. The inhibitory activity of carbohydrate-hydrolyzing enzymes (α-amylase and α-glucosidase) and pancreatic lipase was also assessed. In the 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid assay, an IC50 value comparable to the positive control ascorbic acid (2.87 vs. 1.70 µg/mL, respectively) was obtained. The wild-wall rocket salad extract showed a significant α-amylase inhibitory effect. Obtained results indicate that Sicilian wild-wall rocket contains phytochemicals that can prevent hyperglycemia, hyperlipidemia, and obesity.

Chemical Composition and Evaluation of Insecticidal Activity of Calendula incana subsp. maritima and Laserpitium siler subsp. siculum Essential Oils against Stored Products Pests.

The problems of the environment and human health related to the use of synthetic and broad-spectrum insecticides have increasingly motivated scientific research on different alternatives and among these, the use of green systems, such as essential oils, have been explored. Several species of the Apiaceae and Asteraceae families, aromatic herbs rich in secondary bioactive metabolites, are used in the industrial field for pharmaceutical, cosmetic, and food purposes. Different essential oils extracted from some species of these families have shown acute toxicity and attractive and/or repellent effects towards different insects. In our work, we investigated the toxic potential of Calendula incana subsp. maritima and Laserpitium siler subsp. siculum essential oils against four insect species, Sitophilus oryzae, Lasioderma serricorne, Necrobia rufipes, and Rhyzoperta dominica, which are common pests of stored products. The composition of both oils, extracted by hydrodistillation from the aerial parts of the two plants, was evaluated by GC×GC-MS. Calendula incana subsp. maritima essential oil was rich in oxygenated sesquiterpenoids, such as cubebol (35.39%), 4-epi-cubebol (22.99%), and cubenol (12.77%), while the Laserpitium siler subsp. siculum essential oil was composed mainly of monoterpene hydrocarbons, such as ß-phellandrene (42.16%), limonene (23.87%), and ß-terpinene (11.80%). The toxicity Petri dish bioassays indicated that C. maritima oil killed a mean of 65.50% of S. oryzae and 44.00% of R. dominica adults, indicating a higher biocidal activity in comparison with L. siculum oil, while toward the other species, no significant differences in mortality were recorded. Calendula maritima oil could be, then, considered a promising candidate for further tests as an alternative biocide toward S. oryzae and R. dominica. The possibility that the relatively high content of oxygenated sesquiterpenoids in C. maritima essential oil determines its higher biocidal activity is discussed.

Chemical Constituents and Biological Properties of Genus Doronicum (Asteraceae).

The genus Doronicum, belonging to tribe Senecioneae (Fam. Asteraceae), is found mainly in the Asia, Europe and North Africa. This genus of plant has always been used in traditional medicinal treatments due to the many biological properties shown such as killing parasitic worms and for relieving constipation, as well as to improve heart health, to alleviate pain and inflammation, to treat insect bites, etc. According to the World Flora the genus Doronicum contains 39 subordinate taxa.[1-3] The purpose of this article, which covers data published from 1970 to 2021 with more than 110 articles, aims to carry out a complete and critical review of the Doronicum genus, examining traditional uses and reporting the antioxidant, antimicrobial, anti-inflammatory and antitumor activity shown from crude extracts or essential oils, and from single isolated compounds. Furthermore, critical considerations of the published data have been highlighted by comparing them with the results obtained from species of other genus belonging to the Asteraceae family.

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

The chemical composition and the qualitative and quantitative variability of the essential oils of three taxa belonging to the Teucrium genus were studied. The investigated taxa, that grow wild in Sicily, were Teucrium flavum L. (section Chamaedrys (Mill.) Scheb.), Teucrium montanum and Teucrium capitatum L. of section Polium (Mill.) Scheb. Essential oils were extracted by hydrodistillation and analyzed by GC-MS. In total, 74 compounds were identified. Sesquiterpene hydrocarbons were found to be the main group for T. flavum (48.3%). T. capitatum consisted essentially of monoterpene hydrocarbons (72.7%), with α-pinene (19.9%), ß-pinene (27.6%) and sylvestrene (16.6%) as the most abundant compounds whereas ledene oxide (12.1%), epiglobulol (13.5%) and longifolenaldehyde (14.5%) were identified as the main constituents among the oxygenated sesquiterpenes (63.5%) of T. montanum. Furthermore, a complete literature review on the composition of the essential oils of all the other accessions of these Teucrium taxa, studied so far, was performed. Hierarchical Cluster Analysis (HCA) and Principal Component Analyses (PCA) were used in order to demonstrate geographical variations in the composition of the essential oils.

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-sulfonic acid) (ABTS) test (IC50 of 14.05 µg/mL). Additionally, hypoglycemic and antilipidemic effects were evaluated. Lipase enzyme was inhibited with an IC50 value of 41.99 µg/mL. Obtained data demonstrated that F. nodosa could be considered a promising source of bioactive compounds useful for the treatment and management of obesity.

High-Performance Liquid Chromatography/Electrospray Ionization Tandem Mass Spectrometry (HPLC-ESI-MSn) Analysis and Bioactivity Useful for Prevention of "Diabesity" of Allium commutatum Guss.

This study aimed at evaluating and comparing the chemical profile obtained by HPLC-ESI-MSn analysis, the inhibitory activity of enzymes linked to obesity (α-amylase, α-glucosidase, and lipase) and the antioxidant properties (DPPH, ABTS, FRAP, and ß-carotene bleaching tests) of ethanol extracts of bulbs (BE) and aerial parts (APE) from Allium commutatum Guss. (known in Italy as "aglio delle isole"). The chemical profile revealed alliin as the main abundant compound with values of 31.5 and 38.8 mg/g extract for BE and APE, respectively. APE is rich also in quercetin (38.5 mg/g extract) and luteolin (31.8 mg/g extract). Bulbs extract exhibited the highest activity as inhibitor of enzymes linked to obesity. Except for DPPH test, APE showed the highest antioxidant potential with IC50 of 7.6 and 56.6 µg/mL in ABTS and ß-carotene bleaching test after 60 min of incubation, respectively. In conclusion, the present investigation revealed A. commutatum bulbs and aerial parts as a promising source of inhibitors of enzyme linked to the obesity and of antioxidant compounds.

The Nonvolatile and Volatile Metabolites of Prangos ferulacea and Their Biological Properties.

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 its volatile and nonvolatile metabolites, and outlines its pharmacological effects.

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 are proposed: Helichrysum preslianum subsp. compactum (Guss.) Maggio, Bruno, Guarino, Senatore & Ilardi and Helichrysum panormitanum subsp. latifolium Maggio, Bruno, Guarino, Senatore & Ilardi.

Stachys durandiana Coss., an endemic plant of Morocco: chemical composition of its aerial parts essential oil.

The genus Stachys L. (Lamiaceae) comprises more than 300 species as annual or perennial herbs or small shrubs, spread in temperate regions of Mediterranean, Asia, America, and Southern Africa and several species have been used in the traditional medicine of many countries. Section Stachys, one of nineteen sections of genus Stachys, is divided in two subsections: Sylvaticae and Circinatae. In the present study the chemical composition of the essential oil from aerial parts of Stachys durandiana Coss., endemic of Morocco, and belonging to subsection Circinatae, was analysed by GC-MS. No report has been previously published on this species. The result showed the presence of large quantity of monoterpene hydrocarbons (73.3%), being α-pinene (38.0%) ß-pinene (14.8%), and limonene (11.1%) the principal constituents. Furthermore, a complete review on the chemical composition and biological properties of all the other Stachys taxa, belonging to section Stachys, studied so far, was carried out.

The essential oil chemical composition of a sicilian (Italy) accession of Doronicum caucasicum M. Bieb.

Doronicum is a relatively small genus belonging to the tribe Senecioneae (Fam. Asteraceae), distributed in Asia, Europe, and North Africa. Some of its species are considered toxic due to the presence of pyrrolizidine alkaloids whereas some other ones are largely utilised in the ethnopharmacology of several countries. In the present study, the essential oil composition of a Sicilian accession of Doronicum caucasicum M. Bieb (syn. D. orientale Hoffm.), not previously investigated, is particularly rich in sesquiterpene hydrocarbons (80.3%) with germacrene D (58.9%), α-humulene (8.8%), and ß-caryophyllene (6.5%) as main metabolites. A comparison with all the essential oils from Doronicum taxa studied so far has been carried out.

The essential oil composition of Phlomis bovei subsp. maroccana Maire, an endemic species of Morocco.

Phlomis L. is a genus belonging to the Lamiaceae family, distributed in Macaronesia, the Mediterranean basin, Northeast Africa, Central Asia, and Western Himalaya. Plants of this genus are used against various diseases in the ethno-medicine of several countries and some of them are also utilised for culinary purposes. In the present study, the essential oil chemical composition of the aerial parts of Phlomis bovei subsp. maroccana Maire, an endemic species of Morocco, was analysed by GC-MS. No previous paper has been previously published on this taxon. Main constituents of the essential oil were sesquiterpene hydrocarbons (44.48%) with curcumene (11.20%), a very rare compound in Phlomis essential oils, ß-himachalene (6.22%), and ß-cedrene (3.81%) as principal metabolites. 1-hexadecanol (7.75%) and 1-octadecanol (5.32%) were the main constituents among the alcohols (19.66%). A comparison with all the other essential oils from Phlomis taxa has been carried out.

Cladanthus scariosus Essential Oil and Its Principal Constituents with Cytotoxic Effects on Human Tumor Cell Lines.

Cladanthus is a small genus of the Asteraceae family comprising just five species that, apart from Cladanthus mixtus (L.) Chevall., has a large distribution in all the Mediterranean countries, mainly in the North Africa area. Several ethnopharmacological uses have been reported for species of this genus. Notably, Cladanthus scariosus (Ball) Oberpr. & Vogt is endemic to Morocco. Seeking to delve deeper into the phytochemistry and pharmacological aspects of this species, in this work, we investigated the essential oil (EO) obtained from the aerial parts of a locally sourced accession, hitherto unexplored, growing wild near Tizi n'Ticha, Morocco. The chemical composition of the EO, obtained by the hydrodistillation method, was evaluated by GC and GC-MS. The most abundant EO constituent was germacrene D (13.2%), the principal representative of the sesquiterpene hydrocarbons class (27.2%). However, the major class of constituents was monoterpene hydrocarbons (43.0%), with α-pinene (11.9%), sabinene (10.2%), p-cymene (8.5%), and α-phellandrene (5.2%) as the most abundant. The EO and its main constituents have been tested for their possible cytotoxic activity against three human tumor cell lines (MDA-MB 231, A375, and CaCo2) using the MTT assay, with corresponding IC50 values of 13.69, 13.21, and 22.71 µg/mL, respectively. Germacrene D and terpinen-4-ol were found to be the most active constituents with IC50 values between 3.21 and 9.53 µg/mL. The results demonstrate remarkable cytotoxic activity against the three human tumor cell lines studied, and in the future, further analyses could demonstrate the excellent potential of C. scariosus EO as an antitumor agent.

The chemical composition of the aerial parts' essential oil of matthiola fruticulosa (L.) maire growing in Sicily, Italy.

Matthiola Aiton is a genus belonging to the Brassicaceae family, distributed in Macaronesia, the Mediterranean basin, and the Saharo-Sindian region. Plants of this genus are used against various diseases in the ethno-medicine of several countries and a complete review of their usage has been carried out in this paper. In the present study, the essential oil chemical composition of the aerial parts of the Sicilian accession of Matthiola fruticulosa (L.) Maire, a species growing in South-Western Europe, Northern Africa, and Western Asia, was analysed by GC and GC-MS. No previous paper has been previously published on the essential oil of this species. Main constituents of the oil were sulphur compounds (45.5%) with the two quite rare cis and trans isomers of 5-(methylthio)-4-pentenenitrile as principal metabolites (16.3% and 10.7%, respectively). Principal compound of the oil was the diterpene phytol (16.5%) whereas other terpenoids were less abundant (10.6%).

Chemical Characterization, Free Radical Scavenging, and Cellular Antioxidant Properties of the Egadi Island Endemic Brassica macrocarpa Guss Leaf Extract.

The genus Brassica is an important source of food in the Mediterranean diet with documented nutritional and medicinal properties. However, few studies have investigated the phytochemical composition and the biological activity of wild Sicilian taxa. Thus, we aimed to study the chemical profile and the antioxidant potential, in vitro and in LPS-stimulated RAW 264.7 cells, of a methanolic extract of leaves of wild Brassica macrocarpa Guss (B. macrocarpa) (Egadi Islands; Sicily-Italy). B. macrocarpa methanolic extract showed a large amount of glucosinolates and different phenolic compounds. It exhibited antioxidant activity in the DPPH assay and in LPS-stimulated RAW 264.7 cells, being able to reduce NO and ROS levels and NOS2 mRNA expression. Our study demonstrated that Sicilian B. macrocarpa methanolic extract, in LPS-stimulated macrophages, efficiently counteracts oxidative stress and displays radical scavenging activity. Future studies are required to identify the contribution of the single phytocomponents, to characterize the action mechanism, and to reveal possible applications in human health.

The chemical composition of the aerial parts essential oils of four Andryala species (Asteraceae) growing wild in Morocco.

Andryala (Asteraceae: Cichorieae) is a little-known Mediterranean-Macaronesian genus whose taxonomy is very much in need of revision. In the present study, the chemical composition of the essential oils (EOs) from aerial parts of as many Andryala species, A. integrifolia, A. cossyrensis, and A. rothia, never studied before, and of A. pinnatifida subsp. mogadorensis, all collected in Morocco, was evaluated by GC-MS. The main components of the EOs of A. integrifolia and A. pinnatifida subsp. mogadorensis were organic acid compounds (41.10% and 43.52%, respectively), whereas A. cossyrensis, and A. rothia were shown to be rich in alkane derivatives (43.10% and 34.29%, respectively). Aldehydic compounds were the second class of metabolites in A. integrifolia and A. rothia (26.67% and 21.91%, respectively), whereas terpenoids, represented in all the four species in limited amounts, were more abundant only in A. pinnatifida subsp. mogadorensis (9.90%) and A. rothia (11.79%) species.

The chemical composition of the aerial parts essential oil of S. spreitzenhoferi Heldr. (Lamiaceae) growing in Kythira island (Greece).

Stachys is a large genus of economically important plants belonging to Lamiaceae family that includes about 300 species as annual or perennial herbs. Several species of this genus are extensively used in various traditional medicines. In the present study the chemical composition of the essential oil from aerial parts of Stachys spreitzenhoferi Heldr., a very rare plant, belonging to Section Candidae, endemic of South Greece and collected in the island of Kythira, was analysed by GC-MS. No one reports have been previously published on this species. The result showed the presence of large quantity of diterpenoids with manoyl oxide (22.1%), as the most abundant component. Other metabolites present in high quantity were trans-nerolidol (18.5%), ß-caryophyllene (11.0%) and germacrene D (8.1%). Chemotaxonomic considerations with respect all the other oils of Stachys taxa, belonging to the same section studied so far, were carried out.

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

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

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

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

Centaurea polyacantha and C. maroccana: the chemical composition of the aerial parts essential oils of these Centaurea species (Asteraceae) collected in Morocco.

In the present study, the chemical composition of the essential oil from the aerial parts of two Centaurea species not previously investigated, C. polyacantha Willd. (sect. Seridia, Asteraceae) and C. maroccana Ball. (sect. Calcitrapa, Asteraceae), collected in Morocco, was evaluated by GC-MS. The main components of the essential oil of the first one were limonene (18.2%), ß-bisabolene (11.5%), (Z)-ß-farnesene (8.6%), and spathulenol (8.3%), whereas the C. maroccana essential oil, practically devoid of terpenoids, was shown to be rich in some unusual Centaurea metabolites: 1-hexadecanol (24.9%), docosane (23.7%), and 1-octadecanol (19.5%). Furthermore, a complete literature review on the composition of the essential oils of all the other taxa of Centaurea, belonging to sections Seridia and Calcitrapa, studied so far, was performed.

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

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