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.

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.

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).

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.

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.