What Socrates drank? Comparative chemical investigation of two Greek Conium taxa exhibiting diverse chemical profiles.

Conium divaricatum, even though exhibiting morphological differences in comparison to its congener of European origin Conium maculatum, is still considered a disputed taxon often referred to as a synonym of the latter. Herein, essential oils of various plant tissues from several populations of both taxa were comparatively investigated, showing distinct chemical profiles. In the case of C. divaricatum, the essential oils were dominated by hydrocarbon esters, among which the main constituents 4'-oxodecyl hexanoate, 4'-oxododecyl hexanoate and 4'-oxooctyl hexanoate were isolated and identified as undescribed natural products. In contrast, the essential oils of C. maculatum were dominated by hydrocarbon alkanes, alkenes and ketones, as well as the polyacetylene (Z)-falcarinol. Even though determination of the total alkaloids content and toxicity assessment against the crustacean Artemia salina did not reveal significant differences, the distinct chemical profiles and the morphological differences observed for both taxa, strongly support their distinction as separate species.

Metabolites with Antioxidant Activity from Marine Macroalgae.

Reactive oxygen species (ROS) attack biological molecules, such as lipids, proteins, enzymes, DNA, and RNA, causing cellular and tissue damage. Hence, the disturbance of cellular antioxidant homeostasis can lead to oxidative stress and the onset of a plethora of diseases. Macroalgae, growing in stressful conditions under intense exposure to UV radiation, have developed protective mechanisms and have been recognized as an important source of secondary metabolites and macromolecules with antioxidant activity. In parallel, the fact that many algae can be cultivated in coastal areas ensures the provision of sufficient quantities of fine chemicals and biopolymers for commercial utilization, rendering them a viable source of antioxidants. This review focuses on the progress made concerning the discovery of antioxidant compounds derived from marine macroalgae, covering the literature up to December 2020. The present report presents the antioxidant potential and biogenetic origin of 301 macroalgal metabolites, categorized according to their chemical classes, highlighting the mechanisms of antioxidative action when known.

Antioxidant Potential of Pine Needles: A Systematic Study on the Essential Oils and Extracts of 46 Species of the Genus Pinus.

The antioxidant activity of the essential oils, as well as of the organic and hydroethanolic extracts, of the fresh needles of 54 pine taxa was evaluated using the peroxy-oxalate and luminol chemiluminescence assays. Among all evaluated essential oils, P. canariensis and P. attenuata displayed the highest levels of activity. P. contorta var. murrayana, followed by P. nigra var. caramanica, exhibited the highest antioxidant capacity among the organic extracts, while the most active hydroethanolic extract was that of P. nigra subsp. nigra. Based on the overall levels of activity, the latter taxon was selected for phytochemical analysis targeting the isolation of the bioactive constituents. As such, the organic extract of P. nigra subsp. nigra was subjected to chromatographic separations to yield 11 secondary metabolites (1-11) that were evaluated for their antioxidant activity. Nonetheless, the isolated compounds were found to be less active than the crude extract, thus suggesting the potential role of synergism.

Chemical Composition of Juniperus phoenicea and J. drupacea Essential Oils and their Biological Effects in the Choriallantoic Membrane (CAM) Assay.

The aim of the present study was the chemical analysis of the essential oils from Juniperus phoenicea and J. drupacea female cones and evaluation of their biological effects. Fresh samples, collected in Greece, were subjected separately to hydrodistillation and the oils obtained analyzed by GC-FID and GC-MS. The oils Were assessed using the CAM (chorioallantoic membrane) assay to evaluate their anti-angiogenic potential and the lack of irritant effects in topical application. GC analysis showed that mainly quantitative differences among the samples were observed: limonene was the most abundant compound in J. drupacea (27.0%) compared with J. phoenicea oil (1.6%); the content of a-pinene was high in both essential oils (J. phoenicea 22.1%, J. drpacea 26.1%) followed by germacrene D (J. phoenicea 7.4%, J. drpacea 7.1%, respectively). Nevertheless, qualitative differences were also detected as the diterpene 4-epi-abietal was present in a considerable amount (13.2%) in J. phoenicea essential oil, but was not detected in J. drupacea oil. In the CAM assay, only J. phoenicea. essential oil evidenced a rather weak anti-angiogenic activity compared with the standard retinoic acid, but no irritant effect was observed for either essential oil suggesting their safety for topical application.

Chemical Composition and Larvicidal Activity of Greek Myrtle Essential Oils against Culex pipiens biotype molestus.

Fresh leaves of Myrtus communis collected from different localities in Greece, were subjected to hydrodistillation and the oils obtained were analyzed by GC-FID and GC-MS. The analyses showed mainly quantitative differences, with the monoterpenes myrtenyl acetate, α-pinene, 1,8-cineole, and linalool, along with limonene, dominating the majority of the analyzed Myrtle oils. The evaluation of the larvicidal activity of the samples against Culex pipiens biotype molestus mosquito showed that all tested samples exhibited moderate to weak toxicity, with cultivated M. communis subsp. communis oil being the most active.

Greek Pinus essential oils: larvicidal activity and repellency against Aedes albopictus (Diptera: Culicidae).

The needle volatiles metabolites of seven Pinus spp.: Pinus nigra (3 samples), Pinus stankewiczii, Pinus brutia, Pinus halepensis, Pinus canariensis, Pinus pinaster and Pinus strobus from Greece were determined by gas chromatography and gas chromatography-mass spectrometry. P. nigra and P. canariensis essential oils were dominated by α-pinene (24.9-28.9 % and 15 %, respectively) and germacrene D (20.3-31.9 % and 55.8 %, respectively), whereas P. brutia and P. strobus by α-pinene (20.6 % and 31.4 %, respectively) and ß-pinene (31.7 % and 33.6 %, respectively). P. halepensis and P. pinaster oils were characterized by ß-caryophyllene (28.5 % and 22.5 %, respectively). Finally, ß-pinene (31.4 %), germacrene D (23.3 %) and α-pinene (17.5 %) were the most abundant compounds in the needle oil of P. stankewiczii. Additionally the larvicidal and repellent properties of their essential oils were evaluated against Aedes albopictus, a mosquito of great ecological and medical importance. The results of bioassays revealed that repellent abilities of the tested essential oils were more potent than their larvicidal activities. The essential oils of P. brutia, P. halepensis and P. stankewiczii presented considerable larvicidal activity (LC50 values 67.04 mgL(-1) and 70.21 mgL(-1), respectively), while the others were weak to inactive against larvae. The essential oils of P. halepensis, P. brutia, and P. stankewiczii presented a high repellent activity, even at the dose of 0.2 µL cm(-2), while in the dose of 0.4 µL cm(-2), almost all the tested EOs displayed protection against the mosquito.

Volatile compounds in Thymus sect. Teucrioides (Lamiaceae): intraspecific and interspecific diversity, chemotaxonomic significance and exploitation potential.

Thymus sect. Teucrioides comprises three species, namely, T. hartvigii, T. leucospermus, and T. teucrioides, distributed in Greece and Albania. The volatile constituents of all species of the section were obtained by hydrodistillation and investigated by GC-FID and GC/MS analyses. Twenty populations were sampled and a total of 103 compounds were identified, representing 98.0-99.9% of the oil compositions. The oils were mainly characterized by high contents of monoterpene hydrocarbons (42.7-92.4%), with the exception of three oils for which oxygenated monoterpenes were the dominating constituents, viz., that of T. hartvigii ssp. macrocalyx, with linalool as main compound (89.2±0.5%), and those of T. hartvigii ssp. hartvigii and of one population of T. teucrioides ssp. candilicus, containing thymol as major component (46.4±3.1 and 38.2±3.9%, resp.). The most common compound in the oils of the 20 populations of the section was p-cymene. Considerable variation was detected within and among populations, and seven chemotypes were distinguished, i.e., p-cymene, linalool, p-cymene/thymol, p-cymene/γ-terpinene, p-cymene/borneol, p-cymene/γ-terpinene/borneol, and p-cymene/linalool chemotypes. Different chemotypes may exist in the same population. Multivariate statistical analyses enabled the segregation of the oils within Thymus sect. Teucrioides into two groups, one consisting of the three subspecies of T. teucrioides and the second comprising the species T. hartvigii and T. leucospermus. A linalool-rich chemotype, unique within the section, distinguished the oil of T. hartvigii ssp. macrocalyx from all other oils. The high oil content of p-cymene and the preference for serpentine substrates render T. teucrioides species promising for future exploitation.

Essential oil composition, adult repellency and larvicidal activity of eight Cupressaceae species from Greece against Aedes albopictus (Diptera: Culicidae).

The present study evaluated leaf essential oils from eight Cupresaceae species; Cupressus arizonica, Cupressus benthamii, Cupressus macrocarpa, Cupressus sempervirens, Cupressus torulosa, Chamaecyparis lawsoniana, Juniperus phoenicea, and Tetraclinis articulata for their larvicidal and repellent properties against Aedes albopictus, a mosquito of great ecological and medical importance. Based on the LC(50) values, C. benthamii essential oil was the most active (LC(50) = 37.5 mg/L) while the other tested Cupressaceae essential oils provided rather moderate toxicity against larvae (LC(50) = 47.9 to 70.6 mg/L). Under the used laboratory conditions, three of the essential oils (C. benthamii, C. lawsoniana, and C. macrocarpa) provided sufficient protection against mosquito adults, equivalent to the standard repellent "Deet" in the 0.2 mg/cm(2) dose, while C. macrocarpa assigned as the superior repellent oil in the 0.08 mg/cm(2) dose. Chemical analysis of the essential oils using gas chromatography and gas chromatography-mass spectrometry revealed the presence of 125 components.

Secondary metabolites from Asperula lutea subsp. rigidula.

From the aerial parts of Asperula lutea subsp. rigidula (Halacsy) Ehrend., an endemic plant of south-eastern Greece, nine known compounds, beta-sitosterol, geniposidic acid, deacetyl-asperuloside, scandoside, chlorogenic acid, quercetin, hyperin, isoquercitrin and rutin, were isolated. From the analysis of a non polar fraction of the methanolic extract by means of GC and GC-MS, eighteen compounds were identified, mainly esters of fatty acids. The major components were the ethyl esters ofpalmitic acid (32.7%), linolenic acid (20.1%) and linoleic acid (10.5%).

Chemical composition and antimicrobial activity of Anthriscus nemorosa root essential oil.

The essential oil obtained by hydrodistillation from the roots of Anthriscus nemorosa (Bieb.) Sprengel (Umbelliferae) was analyzed by GC and GC-MS. Among sixty-two compounds identified (representing 89.0% of the total oil), the main components were: n-nonane (12.1%), n-hexadecanol (6.9%), delta-cadinene (6.4%), beta-pinene (6.0%) and germacrene D (5.4%). Furthermore, the antimicrobial activity of the oil was evaluated against the Gram-positive bacteria Staphylococcus epidermidis (ATCC 12228) and Bacillus subtilis (ATCC 6633), the Gram-negative bacterium Escherichia coli (ATCC 25922), and a yeast Candida albicans (ATCC 10259 and ATCC 24433) using the broth microdilution method.

Antimicrobial activity of the essential oil of Greek endemic Stachys spruneri and its main component, isoabienol.

The essential oils of Stachys spruneri Boiss. (sample A and sample B) were analyzed by GC and GC-MS. (+)-Isoabienol was the dominant component (49.5 and 48.2%, respectively of the total oils) among seventy-two identified constituents. Isoabienol was separated, purified by preparative thin-layer chromatography, and further identified by means ofphysicochemical and spectrometric analysis. The microbial growth inhibitory properties of the essential oil and its main metabolite, the labdane diterpene isoabienol, were determined using the broth microdilution method against eight laboratory strains of bacteria (Gram-positive: Staphylococcus aureus, S. epidermidis, Micrococcus luteus, Enterococcus faecalis, Bacillus subtilis, and Gram- negative: Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, and two strains of the yeast Candida albicans. Both essential oil and isoabienol showed considerable activity against all the microorganisms tested, with the isolated compound being most active.

Chemical composition, larvicidal evaluation, and adult repellency of endemic Greek Thymus essential oils against the mosquito vector of West Nile virus.

The volatile metabolites of Greek wild growing Thymus leucospermus and Thymus teucrioides subsp. candilicus were determined by gas chromatography and gas chromatography-mass spectrometry. The monoterpene hydrocarbon p-cymene (64.2%) dominated T. leucospermus oil, followed by γ-terpinene (7.9%), thymol (4.8%), and borneol (4.7%), whereas the most abundant constituents in T. teucrioides subsp. candilicus oil were p-cymene (25.5%), γ-terpinene (19.0%), thymol (18.8%), borneol (5.7%), and α-pinene (5.7%). The larvicidal and repellent activities of the analyzed essential oils were tested on Culex pipiens larvae and adults, respectively. Additionally, the main metabolite of the essential oils, p-cymene was tested against C. pipiens adults in order to define the affiliation between p-cymene and the repellent properties of the oil. The essential oils of T. leucospermus and T. teucrioides subsp. candilicus provided repellency 78.1% and 72.9%, respectively, statistically equal to the reference product icaridin. The compound p-cymene showed almost no repellent activity. The essential oil of T. leucospermus presented lower larvicidal activity (LC(50) = 34.26 mgl(-1)) against C. pipiens third-fourth instar larvae while T. teucrioides subsp. candilicus was the most active with an estimated LC(50) value of 23.17 mgl(-1).

Chemical composition and biological activities of Calamintha officinalis Moench essential oil.

Calamintha officinalis Moench essential oil is used in cooking as an aromatic herb and also to improve the flavor and fragrance of several pharmaceutical products. The essential oil, obtained by hydrodistillation (5 mL/kg), was analyzed by gas chromatography-mass spectrometry and gas chromatography-flame ionization detection. Sixty-four components were identified, constituting 99.7% of the total oil. The major component was found to be carvone (38.7%), followed by neo-dihydrocarveol (9.9%), dihydrocarveol acetate (7.6%), dihydrocarveol (6.9%), 1,8 cineole (6.4%), cis-carvyl acetate (6.1%), and pulegone (4.1%). The essential oil showed antifungal and antimicrobial activity against Gram-positive bacteria. In addition, it presented a very low toxicity both in vivo (50% lethal dose >100 mg/kg) and in vitro in the Artemia salina test (50% lethal concentration >500 µL/mL). C. officinalis essential oil, in rodents, produces the typical effects in behavior of a nonselective central nervous system-depressant drug; it potentiates the hypnotic effects of sodium pentobarbital, decreasing the induction time and enhancing the sleeping time. Moreover, it produces a decrease in body temperature and a protection against pentylenetetrazole-induced convulsions.

Antioxidant activity of Nepeta nuda L. ssp. nuda essential oil rich in nepetalactones from Greece.

Essential oils from air-dried leaves and verticillasters of Nepeta nuda ssp. nuda from Greece were analyzed by means of gas chromatography-flame ionization detection and gas chromatography-mass spectrometry. The dominant constituent in the verticillaster oils was 4aα,7α,7aß-nepetalactone (75.7%). The main metabolites of the leaf oil were 1,8-cineole (16.7%), 4aα,7α,7aß-nepetalactone (24.7%), and caryophyllene oxide (16.3%). The oils were examined for their antioxidant activity. Neutralization of stable 2,2-diphenyl-1-picrylhydrazyl radical ranged from 10.83% (2.50 µg/mL) to 58.64% (50.00 µg/mL) for verticillaster oil and from 6.25% (2.50 µg/mL) to 57.79% (50.00 µg/mL) for leaf oil. The essential oil from verticillasters had significant effects on lipid peroxidation (in the range of 41.18-59.23%), compared to tert-butylated hydroxytoluene (37.04%). In contrast, the essential oil from leaves exhibited pro-oxidant activity at the highest concentration applied.

Comparative analysis of essential oils of six Anthemis taxa from Serbia and Montenegro.

The essential-oil composition of six Anthemis taxa from several populations in Serbia and Montenegro, Anthemis triumfetti (L.) DC., A. tinctoria L., A. austriaca Jacq., A. ruthenica Bieb., A. cotula L., and A. cretica ssp. carpatica (Willd.) Grierson were analyzed by GC and GC/MS. The main constituents have been identified as follows: camphor (13.8-15.4%), alpha-pinene (5.2-9.3%), beta-pinene (4.9-7.8%), and (E)-caryophyllene (7.3-9.8%) in three populations, and cis-chrysanthenol (27.0%) and 1,8-cineole (8.4%) in one population of A. triumfetti; 1,8-cineole (9.0-25.8%) in the oils of five populations, and borneol (16.0%) and spatulenol (16.0%) in the oil of one population of A. tinctoria; cis-chrysanthenyl acetate (17.5-22.0%), beta-pinene (8.6-13.2%), and 1,8-cineole (7.2-10.4%) in the oils of A. austriaca; germacrene D (8.3-11.3%) and terpinen-4-ol (6.3-7.3%) in A. ruthenica oils; beta-cedrene (10.3-19.0%), (E)-beta-farnesene (7.8-13.5%), and germacrene D (5.2-9.1%) in the oils of A. cotula; cis-thujone (39.0%), trans-thujone (13.5%), and yomogi alcohol (7.1%) in the oil of A. cretica ssp. carpatica. The essential oil of A. austriaca was studied for the first time. A cluster analysis based on the relative percentages of all components of the essential oils was used to determine the distances between taxa and populations.

Chemical composition and larvicidal evaluation of Mentha, Salvia, and Melissa essential oils against the West Nile virus mosquito Culex pipiens.

The volatile metabolites of wild-growing Mentha spicata, M. longifolia, M. suaveolens, Melissa officinalis, Salvia fruticosa, S. pomifera subsp. calycina, and S. pomifera subsp. pomifera from Greece were determined by gas chromatography and gas chromatography-mass spectrometry. The insecticidal properties of the analyzed essential oils were screened on Culex pipiens larvae. Additionally two of the main components of the essential oils, piperitenone oxide and 1,8-cineole were assayed against C. pipiens in order to define the affiliation between them and the larvicidal properties of the oils. The most effective oils were M. suaveolens (major constituent piperitenone oxide, 62.4%), M. spicata (piperitenone oxide, 35.7% and 1,8-cineole, 14.5%) and M. longifolia--Central Greece (piperitenone oxide, 33.4%; 1,8-cineole, 24.5% and trans-piperitone epoxide, 17.4%), which exhibited LC(50) values ranging from 47.88 to 59.33 mg l(-1). Medium activity revealed the oils of M. officinalis (terpin-4-ol, 15.8%; caryophyllene oxide, 13.2%; sabinene, 12.9%; beta-pinene, 12.1%; and trans-caryophyllene, 10.2%), M. longifolia--Southern Greece (carvone, 54.7% and limonene 20.0%), S. pomifera subsp. pomifera (trans-caryophyllene, 22.5% and trans-thujone, 21.0%), S. pomifera subsp. calycina--West Southern Greece (trans-thujone, 56.1% and 1,8-cineole, 10.4%), and S. fruticosa--population 2 (camphor, 23.1%; alpha-pinene, 12.7%; and borneol, 12.6%), with LC(50) values ranging from 78.28 to 91.45 mg l(-1). S. pomifera subsp. calycina (Central Greece) essential oil (trans-thujone, 26.5% and cis-thujone, 12.0%) presented rather low activity (LC(50) values 140.42 mg l(-1)), while S. fruticosa--population 1 (1,8-cineole, 31.4% and camphor, 22.6%) was the only inactive oil. Additionally, the constituent piperitenone oxide was found to be highly active (LC(50) values 9.95 mg l(-1)), whereas 1,8-cineole revealed no toxicity.

Essential oil from the underground parts of Laserpitium zernyi: potential source of alpha-bisabolol and its antimicrobial activity.

The composition and antimicrobial activity of the essential oil from the underground parts (roots and rhizomes) of Laserpitium zernyi Hayek (Apiaceae) were investigated. The pale blue essential oil, obtained by hydrodistillation, was analyzed by GC and GC-MS. Forty-three compounds were identified (94.3% of total oil). The main constituent, beside alpha-pinene (31.6%) was alpha-bisabolol (30.9%), so this oil may be a novel potential natural source of this sesquiterpene alcohol. The antimicrobial activity was tested using the microdilution method against Gram (+) bacteria (Staphylococcus aureus, S. epidermidis, Micrococcus luteus, Enterococcus faecalis), Gram (-) bacteria (Pseudomonas aeruginosa, Klebsiella pneumoniae, Escherichia coli), and two strains of yeast (Candida albicans). L. zernyi oil showed significant antibacterial activity against S. epidermidis, S. aureus and M. luteus, but lower activities against the other tested strains.

Volatile constituents of different parts of Smyrnium olusatrum from Greece.

The essential oils from stems, leaves, inflorescences, and both unripe and ripe infructescences of Smyrnium olusatrum L. (Umbelliferae) collected in Greece were obtained by hydrodistillation and analyzed by GC-FID and GC-MS. Fifty-eight components were identified. Among the samples analyzed, the differences observed were mainly quantitative. All oils were characterized by the abundance of sesquiterpenes. The major components of the stem and leaf oils were furanoeremophil-1-one (54.3% and 28.7%, respectively) and curzerene (18.8%, 29.0%). The main constituents of the inflorescence oil were curzerene (38.1%), germacrone (20.2%) and furanoeremophil-1-one (20.0%), while those of the unripe and ripe infructescence oils were 1beta-acetoxy-furanoeudesm-4(15)-ene (22.1%, 30.8%) and curzerene (29.7%, 17.4%).

Essential oil composition and enantiomeric distribution of fenchone and camphor of Lavandula cariensis and L. stoechas subsp. stoechas grown in Greece.

The essential oils from leaves and inflorescences of L. cariensis Boiss. and L. stoechas L. subsp. stoechas collected in Greece were analyzed by GC and GC/MS. In the inflorescences and leaves essential oils of L. cariensis the most abundant metabolite was camphor (51.8, 48.8% respectively), whereas in the essential oils of L. stoechas subsp. stoechas, the main constituents were fenchone (39.9, 21.0% respectively) and camphor (24.2, 26.3% respectively). Both enantiomers of camphor were present, whereas only (+) fenchone was detected.