Dihydrophenanthrenes from a Sicilian Accession of Himantoglossum robertianum (Loisel.) P. Delforge Showed Antioxidant, Antimicrobial, and Antiproliferative Activities
The peculiar aspect that emerges from the study of Orchidaceae is the presence of various molecules, which are particularly interesting for pharmaceutical chemistry due to their wide range of biological resources. The aim of our study was to investigate the properties of two dihydrophenanthrenes, isolated, for the first time, from Himantoglossum robertianum (Loisel.) P. Delforge (Orchidaceae) bulbs and roots. Chemical and spectroscopic study of the bulbs and roots of Himantoglossumrobertianum (Loisel.) P. Delforge resulted in the isolation of two known dihydrophenanthrenes—loroglossol and hircinol—never isolated from this plant species. The structures were evaluated based on 1H-NMR, 13C-NMR…
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…
The chemical composition of the aerial parts essential oil of Ammi crinitum Guss. (Apiaceae) endemic of Sicily (Italy)
Ammi L. is a small genus of economically important plants belonging to Apiaceae family that includes only six taxa. In the present study the chemical composition of the essential oil from aerial parts of Ammi crinitum Guss., a very rare plant, endemic of Sicily, was analyzed by GC–MS. No previously paper has been published on this species. The results showed the presence of large quantity of monoterpene hydrocarbons with sabinene (63.9%), as the most abundant component. Other metabolites present in good quantity were γ-terpinene (8.0%), and 4-terpineol (3.7%). Based on the composition of the essential oil of all the other Ammi taxa, several considerations have been carried out.
The chemical composition of the aerial parts essential oil of four Phagnalon species collected in Sicily (Italy) and Greece
The genus Phagnalon Cass., included in the Asteraceae family, has a wide distribution, expanding from Macaronesia in the West to the Himalayas in the East, from South France and Nord Italy to Ethiopia and Arabian Peninsula. Various species of Phagnalon have been used in the popular medicine of several countries as medicinal herbs and food. The extracts and the secondary metabolites, have a varied application spectrum at several biological levels, with antimicrobial, antioxidant, antidiabetic, antitumor, etc. properties having been reported. The essential oils of four taxa, Phagnalon rupestre, Phagnalon saxatile var. viride, and Phagnalon rupestre subsp. illyricum var. metlesicsii collected …
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.
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 wher…
The chemical composition of the aerial parts essential oil of Lonas annua (L.) Vines & Druce (Asteraceae)
Lonas annua (L.) Vines & Druce (Asteraceae), commonly known as African Daisy or Yellow Ageratum is a rare therophyte native to northwestern Africa (Algeria, Morocco, and Tunisia) and Italy (Sicily and Sardinia). In the present study, the chemical composition of the essential oil from aerial parts of Lonas annua was analyzed by GC-MS. No one report has been previously published on the essential oil of this species. The results showed the presence of large quantity of two unusual metabolites 2,3-dihydrofarnesol (41.64%), and acenaphthene (36.18%). Chemotaxonomic considerations were carried out in order to confirm the phylogenetic reconstructions of Anthemideae.
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…
Chemical Composition and Evaluation of Insecticidal Activity of Seseli bocconei Essential Oils against Stored Products Pests
In this study, the chemical composition of the essential oils (EOs) obtained from different aerial parts (flowers, leaves, and stems) of Seseli bocconei Guss., a wild species endemic of Sicily, was investigated. Furthermore, the EOs’ biocidal effects towards two pests of stored products, Sitophilus oryzae and Callosobruchus maculates, were evaluated. This activity was evaluated in Petri dish bioassays to establish the survival rate of adults treated with the EOs comparing them with solvent and a commonly used insecticide (pyrethrum). The data obtained from the toxicity bioassay evidenced that stems’ EOs and leaves’ EOs have a contact/fumigation effect towards the two insec…
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…
Chemical composition, antimicrobial and antioxidant activities of the essential oil of Italian Prangos trifida (Mill.) Herrnst. & Heyn
In this work, the essential oil of the aerial parts of a not previously investigated accession of Prangos trifida (Mill.) Herrnst. & Heyn (Apiaceae), collected in Northern Italy, was analysed by GC/MS. Twenty-five compounds were identified, accounting for 91.30% of the total oil, which is characterised by a high content of monoterpene hydrocarbons (71.26%). The main constituents of the essential oil were cis-beta-ocimene (18.12%), alpha-phellandrene (12.14%), sylvestrene (11.32%), p-mentha-1,3,8-triene (9.56%) and alpha-pinene (8.85%). The essential oil of P. trifida showed a good antimicrobial activity directed above all against Gram-positive bacteria, and had an interesting antioxidan…
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…