A new eudesmanolide from Tanacetum balsamita L. and biological activities of extracts.

The ethyl acetate and methanol extracts from aerial parts of Tanacetum balsamita yielded a new derivative of 1-acetyl-erivanin, namely 1-acetyl-3-epi-erivanin (17), some known compounds, namely seventeen sesquiterpene lactones, five flavonoids, four coumarins, and a steroid. All extracts displayed antibacterial activity against test microorganisms except for Escherichia coli. The methanol (TBM) extract with an IC50 value of 0.180 mg/mL exhibited good antioxidant activity against DPPH radical while all extracts showed significant anti-inflammatory activity against lipoxygenase enzyme. The ethyl acetate (TBEA) extract presented moderate activity against α-glucosidase enzyme with an IC50 of 0.808 mg/mL. The highest total phenol content with 91.050 mg GAE/g extract was found in TBM. It is the first study on the isolation of secondary metabolites as well as 5-lipoxygenase and α-glucosidase inhibitory activity of T. balsamita growing in Turkey.

Chemical constituents from Parrotia persica- Structural derivatization and their potential prolyl endopeptidase inhibition activity.

The current study was aimed to evaluate the prolyl endopeptidase (PEP) inhibitory activity of glutinol (1), azadiradione (2), quercetin 3-O-ß-d-glactopyranoside (3), catechin (4), quercetin (5), naringenin (6) isolated from Parrotia persica C. A. Mey. Naringenin (6) was further derivatized into 7-O-propargylnaringenin (7), 4',6',4″-O-propargylchalcone (8), and 4',4″-O-propargylchalcone (9). All compounds 1-9 were evaluated for their PEP inhibition activity. PEP is associated with several diseases, including dementia, and Alzheimer's disease (AD). Azadiradione (2) was less active with IC50 = 356.80 ± 2.9 µM, whereas quercetin (5) showed a potent activity with IC50 = 37.12 ± 2.2 µM, as compared to IC50 = 125.00 ± 1.5 µM of standard drug bacitracin. Naringenin (6) was found to be inactive, whereas its new analogues 7-9 were identified as potent inhibitors of PEP with IC50 = 35.20, 41.20, and 29.60 µM, respectively. Kinetic studies of active compounds indicated their modes of inhibition. Compounds 7-9 were found to be mixed-type inhibitors, while compound 5 was found to be non-competitive inhibitor.

Anti-glycating and anti-oxidant compounds from traditionally used anti-diabetic plant Geigeria alata(DC) Oliv. & Hiern.

A new sesquiterpene lactone geigerianoloide (1) and four known flavonoids axillarin (2), quercetin (3), 3-methoxy-5,7,3',4'-tetrahydroxy-flavone (4) and hispidulin (5) were isolated from Geigeria alata (DC) Oliv. & Hiern. (Asteraceae). Structures were deduced using 1H- and 13C- NMR spectroscopy, mass spectrometry, while the structure of compound 1 was also deduced using X-ray crystallography technique.Geigeria alata is traditionally used for diabetes, therefore compounds were tested for anti-glycation activity, in which compounds 2 and 3 showed potent activities (IC50 values of 246.97 ± 0.83 and 262.37 ± 0.22 µM, respectively) compared to IC50 value 294.50 ± 1.5 µM of rutin. Moreover, compound 4 exhibited a comparable activity to rutin (IC50 = 293.28 ± 1.34 µM). Compound 5 showed a weak activity.Compounds 2, 3, and 4 exhibited potent DPPH radical scavenging activity (IC50 = 0.1 ± 0.00, 0.13 ± 0.00 and 0.15 ± 0.01 µM, respectively). Compounds 2, 3, and 4 demonstrated significant superoxide anion scavenging activity with IC50 values of 0.14 ± 0.001, 0.17 ± 0.00, and 0.11 ± 0.006 µM, respectively.

Bioassay-guided isolation of cytotoxic compounds from Chrysophthalmum montanum (DC.) Boiss.

Bioassay-guided isolation of the 80% methanol extract of the aerial parts of Chrysophthalmum montanum (DC.) Boiss. (Asteraceae) led to the isolation of four known guaianolide-type sesquiterpene lactones, 6α-acetoxy-4α-hydroxy-1ßH-guaia-9.11(13)-dien-12.8α-olide (1), 6α-acetoxy-4α-hydroxy-9ß.10ß-epoxy-1ßH-guaia-11(13)-en-12.8α-olide (2), 4α,6α-dihydroxy-1ß,5α,7αH-guaia-9(10),11(13)-dien-12,8α-olide (3), and (4α,5α,8ß,10ß)-4,10-dihydroxy-1,11(13)-guaidien-12,8-olide (4), along a steroidal glycoside mixture (5a and 5b). The structures of the compounds were identified on the basis of spectroscopic data. Among them, 2, 4 and a steroidal glycoside mixture were obtained from C. montanum for the first time. All isolates were also first time assayed for in vitro cytotoxicities against four human cancer cell lines, i.e. breast (MCF-7, MDA-MB 231), colon (HT-29), and lung (PC3). Among the isolates, 1-3 showed significant inhibitory effect on the proliferation of cancer cells with viability ranging from 6.86 to 26.51%, while steroidal glycoside mixture showed no cytotoxicity, except against HT-29 (viability 61.99%). Compound 4 exhibited strong and selective cell growth inhibition against HT-29 with viability 20.99% and was identified as a promising compound with high selectivity between cancer cells and normal human lung cells (BEAS-2B), especially against HT-29 (IC50 = 12.2 µg/mL) compared to that of cisplatin. These results suggested that 4 is worthy of further study to determine its cytotoxicity mechanisms.

Cytotoxic, Anti-inflammatory, and Leishmanicidal Activities of Diterpenes Isolated from the Roots of Caesalpinia pulcherrima.

A phytochemical investigation on the chloroform extract of Caesalpinia pulcherrima roots led to the isolation of ten known furanocassane diterpenoids, vouacapen-5α-ol (1), 8,9,11,14-didehydrovouacapen-5α-ol (2), 6ß-cinnamoyl-7ß-hydroxyvouacapen-5α-ol (3), pulcherrin A (4), pulcherrin B (5), pulcherrin J (6), pulcherrimin A (7), pulcherrimin B (8), pulcherrimin C (9), and pulcherrimin E (10). Chemical transformation of 3 and 7 gave compounds 6ß-hydroxyisovouacapenol C (11), 6ß-cinnamoyl-7ß-acetoxyvouacapen-5α-ol (12), and pulcherrimin D (13). Cytotoxicity of compounds 1-13 was evaluated against three cancer cell lines (MCF-7, HeLa, and PC-3). Anti-inflammatory potential of the compounds was evaluated via the oxidative burst assay using a luminol-amplified chemiluminescence technique. Leishmanicidal activity was tested against promastigotes of Leishmania major in vitro. Compounds 3, 4, 8, 9, and 10 were found active against all three cancer cell lines with IC50s ranging from 7.02 ± 0.31 to 36.49 ± 1.39 µM. Compounds 8 and 13 exhibited a potent inhibitory effect on reactive oxygen species generated from human whole blood phagocytes (IC50 = 15.30 ± 1.10 µM and 8.00 ± 0.80 µM, respectively). Compounds 3, 9, and 13 showed significant activity against promastigotes of L. major (IC50 = 65.30 ± 3.20, 58.70 ± 2.80, and 55.90 ± 2.40 µM, respectively).

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.

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%).

A novel isopimarane diterpenoid with acetylcholinesterase inhibitory activity from Nepeta sorgerae, an endemic species to the Nemrut Mountain.

From the dichloromethane extract of Nepeta sorgerae, the isolation and structure elucidation are now reported of a new isopimarane diterpenoid, named sorgerolone, and two known triterpenoids, oleanolic acid and ursolic acid. Antioxidant activity of the extracts and the isolated terpenoids was determined by the DPPH free radical scavenging and lipid peroxidation inhibition (beta-carotene bleaching) methods. Anticholinesterase activity of the extracts and isolates was investigated by Ellman's method against AChE and BChE enzymes. Although the antioxidant activity results were low, the AChE enzyme inhibition of the extracts and terpenoids was very promising.

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.