Chemical composition and anticancer activity of the essential oil from Vicia ochroleuca Ten., quite rare plant in Kabylia (Algeria).

The search for new bioactive substances with anticancer activity and the understanding of their mechanisms of action are high priorities in the research effort toward more effective cancer treatments. In this article, we analyzed, for the first time, the chemical composition of the essential oil (EO) hydrodistilled from the aerial parts of Vicia ochroleuca Ten. (Leguminosae) by GC-MS. A total of sixteen compounds representing 82.2% of the total composition were identified. The major compounds were phytone (20.11%), hexadecanoic acid (10.23%), 1-octen-3-ol (9.84%), and 10-epi-α-cadinol (7.13%). Additionally, using the MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide) method, the EO was tested in vitro against a panel of human cancer cells, including breast (MDA-MB 231), colon (HCT116), melanoma (A375), and glioblastoma (T98G), with corresponding IC50 values of 23.07, 47.05, 51.64, and 64.07 µg/mL, respectively. The results demonstrate cytotoxic activity and suggest that V. ochroleuca EO could be regarded as a natural bioactive source.

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 3ß-bromo-2,15-diketoatractyligenin methyl ester. The synthesized compounds resulted active against all cell lines tested. In particular, 15-ketoatractyligenin methyl ester and 3ß-bromo-2,15-diketoatractyligenin methyl ester resulted the most active with IC50 values of 0.427 and 0.723 µM against A375 melanoma cell line. Excellent results were also obtained against the colon cancer cell line CaCo2, with slightly lower antiproliferative activity. An interesting extension of the study should be to analyze the atractyligenin derivatives also as target for human melanoma and human colon cancer cells.

A vibrational in vitro approach to evaluate the potential of monoolein nanoparticles as isofuranodiene carrier in MDA-MB 231 breast cancer cell line: New insights from Infrared and Raman microspectroscopies.

Isofuranodiene (IFD) is a sesquiterpene occurring in several plant species, which proved to have multiple anticancer activities. IFD has a lipophilic nature and, hence, a very low water solubility and a poor bioavailability; moreover, it is not stable, undergoing the "Cope rearrangement" to the less active curzerene. The use of appropriate delivery systems can thus be considered as a valid tool to enhance IFD bioavailability, solubility, stability and at the same time also to improve its intracellular uptake and pharmacological activity. Within this frame, monoolein (GMO) nanoparticles loaded with IFD were prepared and their enhanced anticancer activity, compared to pristine IFD, was assessed. In this study, for the first time, an in vitro Fourier Transform Infrared and Raman Microspectroscopy approaches were exploited to evaluate the effects of IFD, alone and loaded in GMO nanoparticles, on MDA-MB 231 breast cancer cell line. The anti-cancer effects of IFD were evidenced by both the spectroscopic techniques and discriminated from the GMO-induced changes in the culture environment; moreover, a synergistic effect of IFD and GMO administration can be envisaged by the experimental results.

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.

Chemical Composition and Antiproliferative Effect of Essential Oils of Four Solidago Species (S. canadensis, S. gigantea, S. virgaurea and S.×niederederi).

There is a growing interest in the research of natural products with potent activity in the prevention and treatment of diseases. Thereby, essential oil phytochemicals have demonstrated broad bioactivities. This study highlights the chemical composition of essential oils obtained from the leaves and inflorescences of diverse species of the genus Solidago (Solidago canadensis, Solidago gigantea, Solidago virgaurea and Solidago×niederederi), also known as Goldenrod, through GC/MS analysis, and their antiproliferative activity on three human tumor cell lines (MDA-MB 231, A375 and HCT116) by the MTT assay. The most represented chemical classes in the essential oils were oxygenated sesquiterpenes, sesquiterpene hydrocarbons, oxygenated monoterpenes and monoterpene hydrocarbons, with a remarkable contribution of compounds such as germacrene D (3.89-19.51 %), α-pinene (3.59-18.82 %), bornyl acetate (3.30-12.73 %) and caryophyllene oxide (3.07-9.18 %). Chemical quali- and quantitative differences were noticed between the leaves and flowers of the same species, as well as between the studied species. The MTT assay showed that the essential oils from the leaves were more active than those from the flower ones. The essential oil having the highest impact on cell viability was that from S.×niederederi (IC50 =12.93, 6.72, and 6.82 µg/ml), followed by S. virgaurea (IC50 =13.39, 7.96, and 8.36 µg/ml) and finally S. gigantea (IC50 =18.04, 5.94, and 8.10 µg/ml) on MDA-MB 231, A375 and HCT116 cell lines, respectively. The essential oil from S. canadensis showed the lowest activity (IC50 =29.33, 12.63, and 18.03 µg/ml, respectively). Taken together, these findings highlight the Solidago species as good sources of cytotoxic compounds. Further studies are encouraged on the in vivo effects and safety of these products.

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 investigated. Furthermore, due to the observed presence of sulfur-containing and phenolic constituents, the cytotoxicity on tumor cells line was investigated. Results revealed significant AChE inhibitory activity for BE and APE. Both extracts exhibited also moderate antioxidant properties in the in vitro assays. Finally, limited cytotoxic activity was observed towards Human colon carcinoma and adenocarcinoma cell line, with differences between the individual parts tested. HPLC-ESI-MSn analysis showed that hairy garlic is a good source of sulphur compounds, flavonoids and phenylpropanoids derivatives, thus being a valid alternative to the common garlic (A. sativum). This work opens new opportunities for the application of A. subhirsutum as a health-promoting food.

Kisspeptin/GnRH1 system in Leydig cells of horse (Equus caballus): Presence and function.

The objectives of this study were to evaluate in horse testes the expression of kisspeptin (KiSS) and GnRH1 neuropeptides and their cognate receptors, KiSS1R and GnRH1R, as well as their action on testosterone, GnRH1, prostaglandin F2α (PGF2α), and PGE2 synthesis and cyclooxygenase 1 (COX1) and COX2 activity by Leydig cells in vitro. Testes were obtained from 9 sexually mature horses by surgical castration. Immunohistochemistry, evidenced the presence of KiSS, KiSS1R, GnRH, and GnRH1R in Leydig cells, whereas germinal and Sertoli cells were positive only for GnRH1. Transcripts for both neuropeptides and their cognate receptors were revealed in isolated Leydig cells by RT-PCR. Isolated and purified Leydig cells were in vitro cultured with agonists and antagonists of KiSS (KiSS-10 and KiSS-234, respectively) and GnRH1 (buserelin and antide, respectively). KiSS-10 and buserelin increased (P < 0.01) COX1 activity and testosterone and PGF2α basal secretion, while decreased (P < 0.01) that of PGE2. KiSS-10 and buserelin did not affect COX2 activity. GnRH1 basal production was increased (P < 0.01) by KiSS-10, but not by buserelin. Antide counteracted the KiSS and GnRH1 effects, whereas KiSS-234 influence only those of KiSS. Summarizing, the KiSS/GnRH1 system is present in horse Leydig cells and modulates their endocrine activity. In particular, the endocrine effects of KiSS are mediated by GnRH1, so suggesting that hypothalamic-like interaction between KiSS and GnRH1 occurs also in Leydig cells.

AcGly-Phe-Asn(OH) and AcGly-Phe-Asn(NH2) tripeptides selectively affect the proliferation rate of MDA-MB 231 and HuDe cells.

There is increasing interest in the bioactivity of peptides carrying out antiproliferative, antihypertensive, antimicrobial, antioxidant, anticholesterolemic, opioid, and antidiabetic activities. The bioavailability of peptides depends on how readily they are digested by endopeptidases and their ability to pass through cell membranes, features that are determined by the peptide's chemical and physical structure. On the basis of structures present in peptides that have biological activity, particularly antiproliferative activity, the tripeptides AcGly-Phe-Asn(OH) and AcGly-Phe-Asn(NH2) have been designed and synthesized, then tested for their antiproliferative activity on human breast adenocarcinoma cells (MDA-MB 231) and human dermal fibroblasts (HuDe). The results show that the peptides significantly affect the proliferation of MDA-MB 231 and HuDe cells, with differentiated response between tumor and normal cells, and thus indicate that C-terminal amidation plays a role. Interestingly, the activity of both peptides in dermal fibroblasts follows the characteristic biphasic pattern of hormesis, a dose-response relationship.

The volatile oils from the oleo-gum-resins of Ferula assa-foetida and Ferula gummosa: A comprehensive investigation of their insecticidal activity and eco-toxicological effects.

Since time immemorial, the oleo-gum-resins of Ferula assa-foetida and F. gummosa are used in the traditional medical systems as well as in foodstuffs, perfumery and cosmetics. In the present study, we explored the insecticidal efficacy of the essential oils obtained from these oleo-gum-resins to widen their fields of industrial applications. The two essential oils were mainly composed of sulfides [sec-butyl (Z)-propenyl disulfide, sec-butyl (E)-propenyl disulfide, sec-butyl (Z)-propenyl trisulfide and sec-butyl (E)-propenyl trisulfide)] and monoterpenes (α-pinene, ß-pinene and ß-phellandrene), respectively, as determined by GC-MS analysis. The two essential oils were assayed for toxicity on a panel of insects, represented by species of public health relevance (Culex quinquefasciatus and Musca domestica), agricultural (Spodoptera littoralis) and stored-product pests (Prostephanus truncatus and Trogoderma granarium). The ecotoxicological effects of the essential oils were assessed on the aquatic microcrustacean Daphnia magna and the earthworm Eisenia fetida, as well as on human cells. Overall, the two essential oils were effective against important insect pests and vectors. On the other hand, they resulted cytotoxic to fibroblasts and non-target aquatic microcrustaceans. Thus, further insights are needed to determine the full spectrum of their eco-toxicological effects.

Nanostructured liquid crystalline particles as delivery vectors for isofuranodiene: Characterization and in-vitro anticancer activity.

Isofuranodiene is an oxygenated sesquiterpene containing a furan ring isolated from the essential oil of Smyrnium olusatrum L. (Apiaceae) owning notable anticancer activity. Despite its biological potential, the high lipophilicity along with a relatively low stability due to Cope rearrangement giving rise to a less active compound, make the perspective of its therapeutical use unlikely. On this basis, in the present work we evaluated bulk and dispersed non lamellar liquid crystalline phases as effective delivery vectors for isofuranodiene, and capable of preserving its structure and enhancing the biological activity. Small-angle X-ray scattering, dynamic light scattering, and UV resonance Raman spectroscopy were used to characterize the nanosystems in an integrated experimental approach. Encapsulation of isofuranodiene in the lipid matrix resulted in a transition from a cubic Im3m to a reversed hexagonal phase because of the highly lipophilic character of the drug, as obtained in SAXS measurements, and in significant shifts in the components of the Raman spectrum of isofuranodiene. The anticancer activity of isofuranodiene-loaded lipidic nanoparticles was assessed on MDA-MB 231 cell line by MTT assay and was found to be higher than that of pristine isofuranodiene.

Chemical composition and biological activities of the essential oil from Pulicaria undulata (L.) C. A. Mey. growing wild in Egypt.

Pulicaria undulata is used as a traditional herbal remedy in Egypt. We used gas chromatography-mass spectrometry for analysis of essential oil of this plant growing wild in Egypt and 64 compounds were identified. The oil was rich in oxygenated monoterpenes (64.0%) and aromatic derivatives (18.8%). The major components were carvacrol (46.5%), xanthoxylin (18.1%) and carvotanacetone (8.7%). The oil of the Egyptian plant showed significant differences from the oil results reported on this species derived from different accessions. Antioxidant activity was performed by FRAP, DPPH and ABTS assays, and the oil demonstrated a powerful antioxidant properties. Furthermore, cytotoxicity was assessed using MTT assay against three cell lines (A375, T98G, HCT116) and the oil showed moderate results with IC50 of 18.53, 40.64 and 22.23 µg/ml; respectively. The oil showed a good anti-acetylcholinesterase activity (IC50 = 139.2 µg/ml) using Ellman method. In conclusion, the studied oil exhibited a peculiar fingerprint and promising biological activities.

Exploring new applications of tulip tree (Liriodendron tulipifera L.): leaf essential oil as apoptotic agent for human glioblastoma.

Liriodendron tulipifera L. (Magnoliaceae), also known as "tulip tree," is a hardwood plant native to North America, cultivated all over the world and used on an industrial level, especially for its fine wood and to make honey. It has also been traditionally exploited for its antimalarial properties. However, our knowledge about the bioactivity of its essential oil remains patchy. In this research, we focused on the biological evaluation of the volatile fractions obtained from different parts of the plant which are normally discharged by industry, including leaves, flowers, and fruits. For the purpose, the essential oils were obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry (GC-MS). Then, they were evaluated as radical scavenging, antioxidant, antimicrobial, and antiproliferative agents by using DPPH, ABTS, FRAP, disk diffusion, and MTT methods, respectively. The significant toxicity exhibited on human tumor cells, namely A375 malignant melanoma, HCT116 colon carcinoma, MDA-MB 231 breast adenocarcinoma, and T98G glioblastoma multiforme cell lines, prompted us to study the mechanism of action by acridine orange/ethidium bromide double staining and caspase 3 assays. Our findings shed light on the potential applications of tulip tree derivatives as anticancer drugs.

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.

Steroidal saponins from the aerial parts of Cordyline fruticosa L. var. strawberries.

A new sulfated steroidal derivative (fruticogenin A: 1-sulfo-australigenin-3-sodium sulphate, 1) and three new steroidal saponins named fruticoside K (3-sulfo-spirostan-25(27)-ene-1ß,3ß-diol-1-O-[α-L-rhamnopyranosyl-(1 → 4)-ß-D-fucopyranoside], 2), fruticoside L (3-sulfo-spirostan-25(27)-ene-1ß,3ß,6α-triol-1-O-[α-L-rhamnopyranosyl-(1 → 4)-ß-D-fucopyranoside], 3) and fruticoside M (spirostan-25(27)-ene-1ß,3α-diol-1-O-[α-L-rhamnopyranosyl-(1 → 2)-α-L-rhamnopyranoside], 4) were isolated from the aerial parts of Cordyline fruticosa L. var. strawberries. Their structures were established on the basis of 1D and 2D NMR data, mass spectrometry and chemical methods. Compounds 2 and 4 exhibited weak cytotoxicity against melanoma (A375), breast adenocarcinoma (MDA-MB-231), and colon carcinoma (HCT116) human tumor cell lines.

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 α-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 only by synthetic route. The phenolic fraction contained biflavonoids: cupressuflavone (9), followed by minor amounts of amentoflavone (10) and hinokiflavone (11). The essential oil and six purified compounds (1 - 4, 8 and 9) were assessed for biological activities, namely antioxidant (assessed by DPPH· , ABTS·+ and FRAP methods) and cytotoxic effects towards selected human tumor cell lines (MDA-MB 231, A375 and HCT116 cells). Compound 3 exhibited higher radical scavenging activity against ABTS·+ radical than the reference Trolox. Noteworthy, compound 8 showed powerful effects towards tumor cell lines, with IC50 values in the range of 0.060 - 0.201 µm, which make it a promising anticancer drug candidate.

Cytotoxic Essential Oils from Eryngium campestre and Eryngium amethystinum (Apiaceae) Growing in Central Italy.

Eryngium campestre and E. amethystinum are thorny herbs belonging to the Apiaceae family and spontaneously growing in stony pastures and dry meadows, preferentially on calcareous substrates. In the Mediterranean countries, these plants have been used as a food or traditional remedies to treat various ailments. In the present work, we have analyzed the chemical composition of the essential oils distilled from the aerial parts by GC-FID and GC/MS, and evaluated their cytotoxic effects on a panel of human cancer cells, namely A375 (human malignant melanoma), MDA-MB 231 cells (human breast adenocarcinoma), and HCT116 cells (human colon carcinoma), by the MTT assay. Furthermore, the Eryngium essential oils were evaluated for antioxidant and acetylcholinesterase (AChE) activities. The two essential oils were rich in sesquiterpene hydrocarbons, with germacrene D as the major compound, accompanied by allo-aromadendrene, ß-elemene, spathulenol, and ledol. They turned out to be highly cytotoxic on the tumor cells, with IC50 values (1.65 - 5.32 and 1.57 - 2.99 µg/ml for E. amethystinum and E. campestre, respectively) comparable or close to those of the anticancer drug cisplatin. The E. amethystinum essential oil exhibited a moderate antioxidant activity, whereas that of E. campestre a weak AChE inhibition.

Chemical composition, antioxidant activity and cytotoxicity on tumour cells of the essential oil from flowers of Magnolia grandiflora cultivated in Iran.

Magnolia grandiflora (Magnoliaceae) is an evergreen tree with fragrant and showy flowers native to southeastern USA but widely cultivated all over the world and used in cosmetics industry in treatment of skin diseases. Here, we report on the chemical analysis of the essential oil obtained from flowers of plants cultivated in Iran, together with the evaluation of its antioxidant and cytotoxic activities. The essential oil composition was dominated by bioactive sesquiterpenes, namely ß-elemene, bicyclogermacrene, germacrene D and (E)-caryophyllene. The oil exhibited moderate radical scavenging activity towards the [Formula: see text] radical, and mild non-selective inhibitory effects against A375, MDA-MB 231 and T98 G tumour cell lines. The latter were influenced by the presence of the anticancer ß-elemene. These results provided new insights for potential application of M. grandiflora volatile oil in the pharmaceutical and cosmetics industry where only the non-volatile magnolol and honokiol have hitherto been fully exploited.

Phytochemical investigations and antiproliferative secondary metabolites from Thymus alternans growing in Slovakia.

CONTEXT: Thymus alternans Klokov (Lamiaceae) is a neglected species of the genus Thymus (Sect. Serpyllum) endemic to Carpathian area, where it is used as a flavouring agent and for medicinal purposes. OBJECTIVE: The aim of the work was to identify antiproliferative constituents from the flowering aerial parts of this plant. MATERIALS AND METHODS: Thymus alternans extracts were analyzed by HPLC-MSn and subjected to extensive chromatographic separations. The isolated compounds (phenolics and triterpenes) were structurally elucidated by MS and 1D and 2D NMR experiments. Essential oil (EO) composition was determined by GC-FID and GC-MS. Six purified triterpenes and EO were assayed for in vitro antiproliferative activity against a panel of human cancer cells, namely, breast (MDA-MB 231), colon (HCT-15 and HCT116), lung (U1810), pancreatic (BxPC3), melanoma (A375) and cervical carcinoma (A431) cells. RESULTS: The structures of the isolated compounds were achieved on the basis of H-NMR and MS experiments. Luteolin-4'-O-ß-d-glucopyranoside (P1), chrysoeriol-7-O-ß-d-glucopyranoside (P2), chrysoeriol-5-O-ß-d-glucopyranoside (P3), apigenin-7-O-ß-d-glucopyranoside (P4), rosmarinic acid (P5), rosmarinic acid-3'-O-ß-d-glucopyranoside (P6), caffeic acid-3-O-ß-d-glucopyranoside (P7), 3α-hydroxy-urs-12,15-diene (T1), α-amyrin (T2), ß-amyrin (T3), isoursenol (T4), epitaraxerol (T5), and oleanolic acid (T6). GC-MS analysis revealed that the EO of T. alternans was devoid of phenols and belonged to the nerolidol-chemotype, that is typical of the Sect. Serpyllum. The six purified triterpenes (T1-T6) were active with IC50 ranging from 0.5 to 5 µM being comparable or better than those of reference compounds betulinic acid and cisplatin. The EO exhibited significant effects on A375, MDA-MB 231 and HCT116 cell lines with IC50 in the range of 5-8 µg/mL. CONCLUSION: The reported results suggest that T. alternans can be considered as a good source of phytoconstituents with possible importance in the pharmaceutical field.

Stabilization of the cyclodecadiene derivative isofuranodiene by silver (I) coordination. Mechanistic and biological aspects.

The industrial extraction and further applications of isofuranodiene are limited because at room temperature it spontaneously converts to curzerene, a structurally less active isomer. This work definitively identified the structure of isofuranodiene in the solid state, showing the two methyl groups in syn position. In addition, two bioactive metal cations, namely, silver(I) and copper(II) ions, were used in the attempt to obtain the chemical stability of isofuranodiene: in the case of silver(I), a labile adduct was formed, while in the case of copper(II), a more stable 1:1 adduct was achieved. In the former, the presence of silver did not significantly affect the biological activities of isofuranodiene, while in the latter, the copper(II) coordination suppressed them. The biological activities of the isofuranodiene adducts were then evaluated as antiproliferative agents against human tumor cell lines (HCT116, MDA-MB 231, and T98G). In addition, for the first time, isofuranodiene was tested as an inhibitor of DHFR (DiHydroFolateReductase) from Escherichia coli. Anticancer activity was observed in the isofuranodiene with the AgCF3SO3 adduct, in the tested cell lines, with IC50 values ranging from 4.89µM to 13.06µM, while inhibition assays highlighted a Ki of 6.22µM for isofuranodiene and of 0.17µM for the related silver adduct. Docking studies indicated a binding mode score of -6.83Kcal/mol for isofuranodiene, and an energy value of -11.82Kcal/mol for methotrexate (a classic DHFR inhibitor).

Essential Oil of Thymus munbyanus subsp. coloratus from Algeria: Chemotypification and in vitro Biological Activities.

Thymus munbyanus subsp. coloratus (Lamiaceae) is a small shrub endemic to Algeria and Morocco where is found in lawns, rockeries and mountainous regions. From a phytochemical point of view this taxon has never been characterized. In this work we have analysed the chemical compositions of the essential oils obtained from inflorescences and vegetative parts by GC/MS. A new chemotype, i.e. borneol-chemotype, was characterized for the first time in the species. Furthermore, we assessed the biological activities of essential oils, namely the antioxidant, antimicrobial and cytotoxicity on tumor cells that were evaluated by the DPPH, ABTS, and FRAP, disc diffusion, and MTT methods, respectively. Biological assays highlighted a moderate inhibitory effect on Staphylococcus aureus, Escherichia coli and Candida albicans (inhibition zone diameter in the range 9 - 10 mm), and noteworthy cytotoxicity on A375 human melanoma cells (IC50 of 46.95 µg/ml).