Anthemis tricolor Containing Unusual Totarol with Cytotoxic and Acetylcholinesterase-Inhibitory Activity.

Anthemis tricolor is an endemic species of Cyprus, and there is very limited information on its chemistry and pharmacological activities. The study aims to identify the in-vitro cytotoxic and acetylcholinesterase activities of Anthemis tricolor. The compounds responsible for the activities were also identified. Potent extracts of A. tricolor were subjected to preparative isolation and spectral structure determination studies. The chloroform extract contained many components, and due to the small quantity of extract available, enough pure compound(s) cannot be obtained for structure determination studies, though the n-hexane extract afforded two known compounds, totarol (1) and taraxasterol (2). The structures of the compounds (1 and 2) were determined by 1 H and 13 C NMR experiments. The pure compounds were also tested for their acetylcholinesterase inhibitory properties. For compound 1, the IC50 value was found to be 87.88 µg/mL. However, no inhibition was seen for 2. Anthemis tricolor was established to be a valuable source of pharmacologically active compounds and requires further studies.

Essential Oil Composition of Endemic Arabis purpurea Sm. & Arabis cypria Holmboe (Brassicaceae) from Cyprus.

There are very few reports on the phytochemistry of the Arabis L. (Brassicaceae) species in the literature. Here we present essential oil composition of aerial parts of two endemic Arabis species from Cyprus. The essential oils of Arabis purpurea Sm. and Arabis cypria Holmboe afforded very low oil yields (< 0.01% (v/w) yield). Sixty six compounds were identified in the essential oil of A. purpurea that represent 82.75 ± 0.21 % (n = 3) of the oil. The major components of the oil were nonacosane 16.18 ± 0.13 %, heptacosane 14.91 ± 0.17 %, hexahydrofarnesyl acetone 12.44 ± 0.10 % and phytol 7.36 ± 0.10 % (n = 3). Forty three compounds were identified in the essential oil of A. cypria which represent 81.28 ± 1.55 % (n = 3) of the oil. The major components of the oil were nonacosane 20.25 ± 0.47 %, heptacosane 9.13 ± 1.88 %, hexahydrofarnesyl acetone 9.03 ± 0.44 % and 1-tetradecanol 4.38 ± 2.60 % (n = 3). To the best of our knowledge this is the first report on the essential oil compositions of these species.

High Amounts of n-Alkanes in the Composition of Asphodelus aestivus Brot. Flower Essential Oil from Cyprus.

There is only a couple of reports indicating essential oil composition of Asphodelus species in the literature. However, from the members of this genus many non-volatile secondary metabolites were isolated. In Cyprus, Asphodelus aestivus Brot. can be found abundantly in all regions of the island. This plant has various ethnobotanical uses in Cyprus. There is no report on the volatiles nor the essential oil composition of A. aestivus. The smell of A. aestivus flowers resembles that of a cat pee which caught our attention. Therefore, we have carried out GC, GC/MS analysis of the essential oil (yield: 0.01 v/w) obtained from Asphodelus aestivus flowers. Seventeen compounds were identified in the essential oil comprising 96.2% of the oil. The major components of the essential oil were hexadecanoic acid 35.6%, pentacosane 17.4%, tricosane 13.4% and heptacosane 8.4%. In our results, we expected to see sulfur containing cat pee odorants due to the odor of the flower whereas high amounts of n-alkanes, saturated fatty acids and minor amounts of acyclic diterpenes were observed.

Unexpected Irregular Monoterpene "Yomogi Alcohol" in the Volatiles of the Lathyrus L. species (Leguminosae) of Cyprus.

Lathyrus species including L. ochrus and L. sativus are known for their food, feed and horticultural uses. Despite their widespread uses and cultivation, there is limited information on their chemistry. Previously, only the essential oil composition of L. rotundifolius, L. vernus and volatiles of L. odoratus have been reported. In the present research, volatiles of seven Lathyrus L. species, namely, L. aphaca, L. ochrus, L. cicera, L. sativus, L. gorgonei, L. saxatilis and L. blepharicarpos var. cyprius were analyzed by SPME GC-MS for the first time. Plant materials were collected from five different locations in Cyprus (February-March 2012). The main components of L. aphaca volatiles from four locations were yomogi alcohol 26.1-16.5%, camphor 21.6-10.1%, tetradecane 14.3-0%; L. cicera from five locations were yomogi alcohol 20.3-3.0%, camphor 18.7-2.0%; L. gorgonei from two locations were yomogi alcohol 24.5-13.1%, camphor 17.1-9.0% and L. sativus was yomogi alcohol 11.4%, camphor 9.0%. Yomogi alcohol was not present as the major compound in L. ochrus (2-methyl butanoic acid 7.2%), L. saxatilis (hexanal 7.7%) and L. blepharicarpos var. cyprius ((Z)-3-hexenal 8.6%) volatiles. The volatiles of the Lathyrus species were also compared with each other quantitative and qualitatively using AHC analysis to find out differences among the species. The irregular monoterpene yomogi alcohol is reported from the Lathyrus and the Leguminosae family for the first time. The existence of yomogi alcohol in Lathyrus volatiles points out that the irregular monoterpenes are not restricted solely to Asteraceae family.

Essential Oil Composition of Helichrysum conglobatum from Cyprus.

The essential oil of aerial parts of Helichrysum conglobatum (Viv.) Steudel. (Asteraceae) from Cyprus was analyzed by GC and GC-MS. The essential oil yield was 0.01, v/w. Forty five compounds were identified in the oil comprising 96.1% of the total. The essential oil was mainly composed of sesquiterpene type compounds and oxygenated sesquiterpene derivatives. The main components of the oil were P-caryophyllene (14.6%), Y-curcumene (14.1%), hexadecanoic acid (13.5%), tetradecanoic acid (7.5%), rosifoliol (5.4%) and 6-cadinene (5.3%). This is the first report on the essential oil composition of H. conglobatum from Cyprus.

Sitophilus granarius L. (Coleoptera) Toxicity and Biological Activities of the Essential Oils of Tanacetum macrophyllum (Waldst. & Kit.) Schultz Bip.

Insecticides of the natural origin are an important alternative to the synthetic insecticides that are being employed for the preserving stored products. The volatiles obtained from T. cinerariifolium (=Pyrethrum cinerariifolium) is being used for many types of insecticidal applications; however there is a very little information on the insecticidal activity of the essential oils of other Tanacetum species. The main purpose of the present study is to determine the chemical composition of T. macrophyllum (Waldst. & Kit.) Schultz Bip. essential oils and evaluate their insecticidal activity against S. granarius as well as its other beneficial biological activities. Highest contact toxicity was observed in the leaf oil of (88.93%) against S. granarius. The flower oil showed considerable fumigant toxicity against L. minor at 10 mg/mL application concentration (61.86 %) when compared with other samples at the same concentration. The highest DPPH (2,2-Diphenyl-1-picrylhydrazyl) scavenging activity (47.7%) and phosphomolybdenum reducing activity was observed also for the flower oil of T. macrophyllum at 10 mg/mL concentration. The essential oils were analyzed by GC, GC/MS. The flower and leaf oils were characterized with γ-eudesmol 21.5%, (E)-sesquilavandulol 20.3%, copaborneol 8.5% and copaborneol 14.1%, 1,8-cineole 11%, bornyl acetate 9.6%, borneol 6.3% respectively. AHC analysis of the qualitative and quantitative data obtained from the essential oil composition of the T. macrophyllum essential oil from the present research and previous reports pointed out that two different chemotypes could be proposed with current findings which are p-methyl benzyl alcohol/ cadinene and eudesmane chemotypes.

DPPH scavenging, PRAP activities and essential oil composition of edible Lathyrus ochrus L. (Cyprus Vetch, Luvana) from Cyprus.

The essential oil of the aerial parts of edible Lathyrus ochrus L. was investigated by simultaneous GC, GC/MS analyses under the same conditions. Trace amount of oil (0.01> mL) obtained by hydro distillation of 200 g fresh plants was trapped in 1 mL n-hexane. Twenty components were detected representing 91.55 ± 0.56 % of the oil. The main components were phytol 49.39 ± 0.44 %, hexadecanoic acid 20.64 ± 0.89 % and pentacosane 4.20 ± 0.09 %. Essential oil solution (1% oil: n-hexane) afforded similar DPPH scavenging activity (9.28 ± 1.30 %) when compared with positive controls α-tocopherol (9.74 ± 0.21 %) and BHT (7.79 ± 0.26 %) at the same concentrations. Antioxidant activity of the oil was determined using a new HPTLC-PRAP assay. The oil afforded two fold higher reducing activity of phosphomolybdenum complex (594.85 ± 5.14 AU) when compared with positive controls α- tocopherol (271.10 ± 2.86 AU) and BHT (210.53 ± 1.81 AU) at the same concentration.

Chemistry and biological activities of Tanacetum chiliophyllum var. oligocephalum extracts.

Tanacetum chiliophyllum (Fisch. & Mey.) var. oligocephalum (D.C.) Sosn. collected in Turkey was subjected to phytochemical and biological evaluations in this study. Pure compounds were obtained from ethyl acetate extracts of the stems of the plant material. Structures of isolated compounds were determined using spectral methods. Seven known flavones, i.e., 5-hydroxy-3',4',6,7-tetramethoxyflavone, eupatilin (6-hydroxyluteolin-6,3',4'-trimethylether), cirsimaritin (scuttellarin-6,7-dimethylether), cirsilineol, 5-hydroxy-3',4',7-trimethoxy flavone, desmethoxy-centaureidin, and jaceosidin and one known triterpene, taraxasterol acetate, were identified from the ethyl acetate extracts. The first seven compounds, as well as the ethyl acetate and methanol extracts, were also investigated for their insecticidal, antimicrobial, and 1,1-diphenyl-2-picrylhydrazil radical (DPPH)-scavenging activities. The insecticidal contact toxicity of the extracts were evaluated on Sitophilus granarius. The ethyl acetate (81.8%) and methanol (88.4%) extracts of T. chiliophyllum var. oligocephalum showed high toxicity against this pest. Most promising antimicrobial activity was observed for ethyl acetate extracts of the stems against Bacillus cereus. This extract showed the same inhibition concentration (125 microL/mg) with the positive control chloramphenicol. The ethyl acetate (91.9%) and methanol (93%) extracts of the stems showed significant DPPH-scavenging activity compared with the positive controls alpha-tocopherol (94.5%) and butylated hydroxytoluene (92.9%) at 10 mg/mL concentration. Among the isolated compounds, the highest DPPH-scavenging activity was observed for jaceosidin at 1 mg/mL concentration (81.5%).

Essential oil composition of endemic Tanacetum zahlbruckneri (Nab.) and Tanacetum tabrisianum (Boiss.) Sosn. and Takht. from Turkey.

In this study, water-distilled essential oils from the flowers of Tanacetum zahlbruckneri and flowers and stems of Tanacetum tabrisianum from Turkey were analysed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The flower oil of T. zahlbruckneri was characterised by the sesquiterpenes germacrene D (29.7%) and spathulenol (12%). Flower (A) and stem (B) oil of T. tabrisianum was characterised by 1,8-cineole: 17.6% (A), 22.5% (B), hexadecanoic acid: 10.3% (A), 8% (B), decanoic acid: 5.8% (A) and trans-linalooloxide acetate: 5.3% (A), 4% (B). Unlike a previous report on the essential oil composition of T. tabrisianum, in this study a 1,8-cineole and hexadecanoic acid-rich oil with a low percentage of caryophyllene oxide and spathulenol was obtained. The composition of the essential oil of endemic T. zahlbruckneri was investigated for the first time.

Essential oil composition and antibacterial activity of Tanacetum argenteum (Lam.) Willd. ssp. argenteum and T. densum (Lab.) Schultz Bip. ssp. amani heywood from Turkey.

Water-distilled essential oils from aerial parts of Tanacetum argenteum ssp. argenteum and T. densum ssp. amani from Turkey were analyzed by GC and GC/MS. The essential oil of T. argenteum ssp. argenteum was characterized with alpha-pinene 36.7%, beta-pinene 27.5% and 1,8-cineole 9.8%. T. densum ssp. amani was characterized with beta-pinene 27.2%, 1,8-cineole 13.1%, alpha-pinene 9.7% and p-cymene 8.9%. Antibacterial activity of the oils were evaluated for five Gram-positive and five Gram-negative bacteria by using a broth microdilution assay. The highest inhibitory activity was observed against Bacillus cereus for T. argenteum ssp. argenteum oil (125 microg/mL) when compared with positive control chloramphenicol it showed the same inhibition potency. However, the same oil showed lower inhibitory activity against B. subtilis when compared. The oil of T. densum ssp. amani did not show significant activity against the tested microorganisms. DPPH radical scavenging activity of the T. argenteum ssp. argenteum oil was investigated for 15 and 10 mg/mL concentrations. However, the oil did not show significant activity when compared to positive control alpha-tocopherol. Both oils showed toxicity to Vibrio fischeri in the TLC-bioluminescence assay.

Antimicrobial activity and essential oil composition of a new T. argyrophyllum (C. Koch) Tvzel var. argyrophyllum chemotype.

Water-distilled essential oils from flowers and stems of Tanacetum argyrophyllum var. argyrophyllum from Turkey were analyzed by GC and GC/MS. The flower oil of T. argyrophyllum var. argyrophyllum was characterized with camphor 29.7%, borneol 12.0%, 1,8-cineole 8.4% and bornyl acetate 6.1%. Stem oil was characterized with camphor 26.6%, 1,8-cineole 17.5%, and borneol 15.0%. Our previous research and literature on the essential oil of this plant reported oils with high thujone content unlike the present study. Antibacterial activity of the oils were evaluated for five Gram-positive and five Gram-negative bacteria by using a broth microdilution assay. The highest inhibitory activity was observed against Bacillus cereus for stem oil (125 microg/mL) when compared with positive control chloramphenicol it showed the same inhibition potency. However, the same oil showed lower inhibitory activity against B. subtilis. The flower oil did not show significant activity against the tested microorganisms. DPPH radical scavenging activity of the T. argyrophyllum var. argyrophyllum oil was investigated at 15 and 10 mg/mL concentrations. However, the oils did not show any significant activity when compared to positive control alpha-tocopherol. Both of the oils showed toxicity to Vibrio fischeri in the TLC-bioluminescence assay.

Antibacterial activity and the variation of Tanacetum parthenium (L.) Schultz Bip. essential oils from Turkey.

Water-distilled essential oils from herbal parts of Tanacetum parthenium from two different localities in Turkey were analyzed by GC and GC/MS. The essential oil of T. parthenium collected from Davutpasa-Istanbul location were characterized with camphor 49%, trans-chrysanthenyl acetate 22.1% and camphene 9.4%. Second plant sample is collected from the remote east end of the country Savsat-Ardahan location. The essential oil from this location was characterized with camphor 60.8% and camphene 6.8%. Unlike the former this sample contains trans-chrysanthenyl acetate in trace amount and cis- chrysanthenyl acetate in very small amount (0.6%) which is not present in the first sample. Antibacterial activity of the oils were evaluated for five Gram (+) and five Gram (-) bacteria by using a broth microdilution assay. The highest activity was observed on Bacillus subtilis, Staphylococcus aureus and methicillin-resistant S.aureus however when compared with positive control oils showed higher MIC values. The oil of Istanbul-sample showed highest activity on B. subtilis (125 microg/mL) and methicillin-resistant S. aureus (125 microg/mL) which is two fold concentration when compared with the positive control chloramphenicol (62.5 microg/mL). The oil of Ardahan sample showed the highest activity on S. aureus (125 microg/mL) which is likewise two fold concentration of the positive control chloramphenicol (62.5 microg/mL). DPPH scavenging activity was 59.3% of the oil from Davutpasa at 15 mg/mL concentration. When compared to positive control alpha-tocopherol (94.6%) Savsat oil (28.2%) showed low and Davutpasa oil showed medium DPPH scavenging activity. All of the oils showed toxicity to Vibrio fischeri in the TLC-bioluminescence assay.