One new sulfated saponin 3β,23,30-trihydroxyurs-20-en-28-al-23-sulfate 3-O-β-D-xylopyranoside (Zygofaboside C; 1) was purified from the water soluble fraction of ethanolic extract of the aerial parts of Zygophyllum fabago Linn. The structure of the compound was elucidated through spectral studies, especially 1Dand 2D-NMR, HR-FAB mass spectrometry, and comparison with literature data.
Five ursane type sulfated saponins have been isolated from the aerial parts of Zygophyllum fabago Linn. (locally called Chashum). The urease inhibitory effects of these compounds have been investigated for the first time as well as their molecular docking studies have also been carried out to check the structure-activity relationship. The IC50 values of these compounds could not be found due to paucity of the samples. The molecular docking studies were performed only for the most active compound mono sodium salt of 3β,23-di-O-sulfonyl-23-hydroxyurs-20(21)-en-28-oic acid 28-O-[β-D-glucopyranosyl] ester (Zygofaboside A; 1).
From the aerial parts of Zygophyllum fabago, two new monosodium salts of sulfated derivatives of ursolic acid, along with two known quinovic acid glycosides were isolated. The structures of the new compounds were determined as (3 beta,4 alpha)-3,23,30-trihydroxyurs-20-en-28-al 3,23-di(sulfate) sodium salt (1:1) (1) and of (3 beta,4 alpha)-3,23,28-trihydroxyurs-20-en-30-yl beta-D-glucopyranoside 3,23-di(sulfate) sodium salt (1:1) (2) with the molecular formula C(30)H(47)NaO(10)S(2) and C(36)H(59)Na(O)15S(2), respectively. The structures of the known compounds were 3-O-(2-O-sulfo-beta-D-quinovopyranosyl)quinovic acid 28-beta-D-glucopyranosyl ester (3) and 3-O(beta-D-glucopyranosyl)quinovic acid 28-beta-D-glucopyranosyl ester (4) (quinovic acid = (3 beta)-3-hydroxyurs-12-ene-27,28-dioic acid). The structures of all these compounds were determined by using 1D- and 2D-NMR spectroscopic techniques.
A new flavonoid, kaempferol-3,4′-di-O-α-L-rhamnopyranoside (1), and three known flavonoids (2–4) were isolated from the aerial parts of T. communis L. The structure of the new compound was elucidated on the basis of spectroscopic data. Compounds 1 and 2 showed significant antioxidant activity (IC50 187.151 ± 0.821 μM, and 92.079±0.513 μM, respectively), whereas compounds 3 and 4 showed moderate activity in DPPH free radical scavenging assays.
The objective of this study was to examine antibacterial, antifungal, and antimycobacterial properties of Ilex aquifolium L. (Aquifoliaceae) growing in Turkey. The ethanol, ethyl acetate, chloroform, and n-hexane extracts prepared from the leaves of I. aquifolium were tested against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Enterobacter aerogenes, Proteus vulgaris, Salmonella typhimurium, and Candida albicans for antibacterial and antifungal evaluation using the microdilution broth susceptibility assay. In addition, antimycobacterial activity of the crude extracts of I. aquifolium was evaluated by microplate Alamar blue assay. The results showed that the extracts tested, except n-hexane, possessed moderate antibacterial and antifungal activity varying from 62.5 to 250 μg/mL. On the other hand, the ethanol extract of the leaves exhibited a minimum inhibitory concentration value (MIC) against Mycobacterium tuberculosis H37Ra strain of 200 μg/mL.
In the present study, the alkaloid composition of the aerial parts of Genista vuralii A. Duran & H. Dural (Fabaceae) was investigated by capillary GC-MS. Ten quinolizidine alkaloids were identified by capillary GC-MS, namely, N-methylcytisine, cytisine, tetrahydrorhombifoline, 17-oxosparteine, 5,6-dehydrolupanine, lupanine, 17-oxolupanine, anagyrine, baptifoline, and 13 alpha-tigloyloxylupanine. Among them, anagyrine (93.04%) was the most abundant alkaloid. Furthermore, antibacterial and antifungal activities of the alkaloid extract of G. vuralii were tested against standard strains of bacteria (Escherichia coli, Pseudomonos aeruginosa, Bacillus subtilis, Staphylococcus aureus) as well as fungi (Candida albicans, Candida krusei). The alkaloid extract of G. vuralii presented good activity against S. aureus, B. subtilis, and C krusei, with minimum inhibitory concentrations (MIC) of 62.5 mu g/mL. The remaining MIC values were found to range between 125 and 500 mu g/mL. To the best of our knowledge, the current work is the first to report the alkaloid profile and antimicrobial activity of G. vuralii L. growing in Turkey.
Ethnopharmacological relevance: Arctium minus (Hill) Bernh. ssp. minus (Asteraceae) leaves are used to alleviate rheumatic pain, against fever and sunstroke with externally application in Turkish folk medicine.Aim of the study: To evaluate the anti-inflammatory, antinociceptive and antioxidant activities of aqueous and ethanol extracts prepared from the leaves of Arctium minus ssp. minus.Materials and methods: The ethanolic and aqueous extracts from the leaves of Arctium minus ssp. minus were evaluated in mice for anti-inflammatory activity using carrageenan-induced hind paw edema model and for antinociceptive activity using p-benzoquinone-induced abdominal contractions test. Moreover, the antioxidant power of the extracts has been determined by using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and flow injection analysis-luminol chemiluminescence (FIA-CL). In addition, the total phenolic content in both extracts was determined with spectro photometric method.Results: Our results showed that only the ethanol extract exhibited a dose-dependent anti-inflammatory activity ranging between 11.1 and 23.6% at 200 mg/kg dose as well as displayed a significant antinociceptive activity without inducing any gastric damage. Although, both extracts were shown to possess significant DPPH radical-scavenging activity, that of aqueous extract was found to have more pronounced activity. In FIA-CL system, the ethanol extract was shown to possess a significant scavenger activity against H2O2 while the aqueous extract was much more potent antioxidant activity against HOCl-luminol CL than ethanol extract.Conclusion: According to our results, it was concluded that Arctium minus ssp. minus contains potent natural antioxidants. In this study, in vivo experimental results have also supported the folk medicinal utilization of Arctium minus ssp. minus. (C) 2008 Elsevier Ireland Ltd. All rights reserved.
Ethnopharmacological relevance: Rhododendron ponticum L. (Ericaceae) is used for the treatment of inflammatory diseases and to alleviate rheumatic pain and against toothache in Turkish traditional medicine. Aim of the study: To evaluate the anti-inflammatory and antinociceptive effects of Rhododendron ponticum leaves using in vivo models, and isolation and chemical characterization of the biologically active constituents through bioassay-guided fractionation procedures. Material and Methods: Carrageenan-induced hind paw edema model was used for anti-inflammatory activity and p-benzoquinone induced abdominal contractions model for the antinociceptive activity assessment. Results: The ethylacetate fraction displayed marked anti-inflammatory (28.4-40.7% inhibition) and antinociceptive (50.7% inhibition) effects as compared to reference compounds. Through bioassay-guided fractionation and isolation procedures flavonol glycosides [a mixture of hyperoside and isoquercitrin (1) and quercitrin (2)] along with one flavanone glycoside [6-C-glycosylnaringenin (3)] were isolated as the active ingredients of ethylacetate extract against carrageenan-induced edema and p-benzoquinone-induced writhes and their structures were elucidated by spectral techniques. 1 and 2 also showed a significant anti-inflammatory activity against 12-O-tetradecanoyl-13-acetate (TPA)- induced mouse ear edema model. Conclusion: Results of the present study supported the utilization of the plant in Turkish folk medicine and revealed that flavones are the major anti-inflammatory and antinociceptive principles of the leaves.
Purpose of the present study was to evaluate alkaloid profile of the aerial parts of Lupinus angustifolius growing in Turkey by capillary gas chromatography-mass spectrometry (GC-MS). Fifteen alkaloids were identified by capillary GC-MS. 13α-Hydroxylupanine (50.78%) and lupanine (23.55%) were determined as the main alkaloids in the aerial parts of L. angustifolius. Ammodendrine, isoangustifoline, tetrahydrorhombifoline, angustifoline, α-isolupanine, 5,6-dehydrolupanine, 11,12-dehydrolupanine, 13α-acetoxylupanine, 13α-isovaleroyloxylupanine, 13α-valeroyloxylupanine, 13α-tigloyloxylupanine, 13α-cis-cinnamoyloxylupanine and 13α-cis-cinnamoyloxy-17-oxolupanine were identified as the minor alkaloids of the plant. Furthermore, antibacterial and antifungal activities of L. angustifolius alkaloid extract were tested against standard strains of the following bacteria; Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis and Staphylococcus aureus as well as the fungi; Candida albicans and C. krusei. The alkaloid extract showed significant activity on B. subtilis, S. aureus and P. aeruginosa while it was weakly active on E. coli. On the other hand, the extract possessed moderate activity against C. albicans and C. krusei.
Aim: Tamus communis L. ssp. cretica (L.) Kit Tan (Dioscoreaceae), is a perennial herbaceous climbing plant with large fleshy tubers [1]. The aim of work was to examine antioxidant and antimicrobial properties of T. communis. ssp. cretica.
In this research, total and free daidzein content in Genista species growing in Turkey were investigated using the LC-MS method. The highest amount of total and free daidzein in these species was found in Genista sessilifolia and G. lydia var. antiochia as 0.0056 and 0.0009%, respectively. Total and free daidzein content of the aerial parts of other Genista species varied from 0.0003 to 0.0044%, and from 0.0001 to 0.0008%, respectively.
The antioxidant activities of four Lamiaceae plants, Salvia viridis L., Salvia multicaulis Vahl, Stachys byzantina C. Koch and Eremostachys laciniata (L.) Bunge have been determined by using 1,1-diphenyl-2-picrylhydrazyl (DPPH) as well as by flow injection analysis-luminol chemiluminescence (FIA-CL). All extracts were shown to possess a significant scavenger activity against DPPH free radical and an inhibitory effect on H2O2- or HOCl-luminol chemiluminescence. The extracts scavenged 50% of DPPH radical ranging in the following descending order: Salvia viridis > Stachys byzantina > Salvia multicaulis > Eremostachys laciniata. The most potent extract on H2O2-induced peak chemiluminescence was that of Salvia viridis and on HOCl-induced peak chemiluminescence was that of Stachys byzantina. The results concluded that the extracts have a potential source of antioxidants of natural origin.
As a part of our ongoing investigations on Taxus baccata L. (Taxaceae), we have isolated two lignans, lariciresinol (1) and taxiresinol (2), from chloroform extract of the heartwood of this plant. This is the first report for the isolation of lariciresinol from T. baccata. Their structures were elucidated on the basis of spectroscopic methods (IR, EIMS, DCI, 1D and 2D NMR). In addition, molecular mechanic and semi-empirical calculations of these compounds have been carried out by using MM3, PM3 and AM1 programs to obtain three-dimensional most probable geometries.
Eleven species of the Boraginaceae family collected in Turkey were analyzed with respect to the amount of gamma-linolenic acid as well as fatty acid composition. gamma-Linolenic acid was found in all species, except for Heliotropium lasiocarpum Fisch. & Mey. and Heliotropium dolosum De Not. Seed oil content ranged from 1.5% in H. lasiocarpum to 22.0% in Anchusa leptophylla ssp. leptophylla. The content of gamma-linolenic acid ranged from 1.7% of total fatty acids in Paracaryum racemosum (Schreber) Britten var. racemosum to 13.7% in A. leptophylla Roemer & Shultes ssp. leptophylla. According to data from our study, A. leptophylla ssp. leptophylla (13.7%), Anchusa azurea Miller var. azurea (11.9%) and Echium plantagineum L. (12.2%) might be considered as new sources of gamma-linolenic acid.
Four lignan type compounds, lariciresinol, taxiresinol, isolariciresinol and 3-demethyl-iso-lariciresinol, were isolated from the heartwood of Taxus baccata L. (Taxaceae) growing in Turkey through chromatographic techniques. In vivo anti-ulcerogenic potency of these compounds was investigated on ethanol-induced ulcerogenesis model in rats at two different doses, 50 and 100 mg/kg. All compounds were shown to possess significant anti-ulcerogenic activity at both doses. However, the effect of taxiresinol was the most prominent.
Three lignan derivatives, (-)-taxiresinol (1), (-)-3'-demethylisolariciresinol-9'-hydroxyisopropylether (2) and (-)-3-demethylisolariciresinol (3), previously isolated from the heartwood of Taxus baccata L. (Taxaceae) were investigated for cytotoxicity against the Oncology Cell Line Panel (breast, colon, ovary, prostate, lung and a normal adult bovine aortic endothelial cell line) as well as for antimicrobial activities. Besides, a chloroform-soluble portion of the ethanol extract from the heartwood of T baccata was also tested for antimicrobial activities. Compounds 1 - 3 did not demonstrate much cytotoxic potency according to the reference drug etoposide. With the exception of compound 2, the other two lignans (1 and 3) and the chloroform extract were shown to possess antifungal activity, whereas only the chloroform extract exhibited antibacterial activity against Pseudomonas aeruginosa.
Crude extracts prepared from the heartwood of Taxus baccata L. were evaluated for their antiplatelet and vasorelaxing effect. The ethanol extract of the heartwood of T baccata (1) and their fractions, CHCl3 (2) and CHCl3 nonsoluble extract (3) were preincubated with platelets, and then thrombin, arachidonic acid (AA), collagen or platelet-activating factor (PAF) was added for testing antiplatelet activity. In other set of experiments, all extracts were tested on high potassium or norepinephrine (NE) depolarized isolated rat thoracic aorta for investigating the vasorelaxing effect. All tested extracts showed a significant inhibitory effect on platelet aggregation induced by AA, collagen and PAF at a concentration of 400 mug/ml, but not thrombin. However, not all extracts relaxed NE-induced vasocontraction, extracts 1 and 2 showed a weak inhibitor effect on high potassium depolarized smooth muscle. To the best of our knowledge, this is the first report on antiplatelet activity and vasorelaxing effect of the heartwood of T baccata.
The effect of irrigation on the seed yield, oil yield, and oil composition of sunflower in populations of Ekiz1 and VNIIMK 8931, a mixture of N2, N3, and N4 lines, and a synthetic variety obtained from these lines has been studied. The major fatty acid was found to be oleic acid, in addition to linoleic, palmitic, and stearic acids. Irrigation increased seed yield, oil yield, and oil content of all samples. In two of them, the synthetic variety and VNIIMK 8931, the increase was found to be statistically significant. In addition, irrigation of the samples did not increase significantly the amount of oleic and linoleic acids. On the contrary, the amount of linoleic acid in the mixture of N2, N3, and N4 lines and oleic acid in VNIIMK 8931 decreased statistically significantly.
Four taxoids (taxusin, baccatin VI, baccatin III and 1β-hydroxybaccatin I) and five lignans (lariciresinol, taxiresinol, 3′-demethylisolariciresinol-9′-hydroxyisopropylether, isolariciresinol and 3-demethylisolariciresinol) were isolated from the heartwood of Taxus baccata L. (Taxaceae) growing in Turkey through chromatographic techniques. In vivo anti-inflammatory and antinociceptive activity of these compounds were investigated. All the compounds were shown to possess significant antinociceptive activity against p-benzoquinone-induced abdominal contractions, while only lignan derivatives significantly inhibited carrageenan-induced hind paw edema in mice.
Zygophyllum fabago L. a member of the Zygophyllaceae family, is a herbaceous plant found widely in the Mediterranean area. Genus Zygophyllum is represented by only two species, Z. album and Z. fabago, and Z. fabago is widely distributed in Turkey [1]. The plant is reported to be used as antihelmentic, antirheumatic, and antiasthmatic [2]. To date, li ttle phytochemical study has been performed on Z. fabago. From the aerial part of the plant triterpenoid saponins have been isolated [3]. There is no investigation on the seed oil of Z. fabago. Fatty acids, especially essential fatty acids (E FAs), are of vital significance for human beings. The role of E FAs such as linoleic (18:2ω6) and γ-linolenic (18:3ω6) acids obtained from various oils (mainly evening primrose, borage, and black currant oils) in the diet is crucial. It has also been suggested that consumption of a diet enriched in E FAs confers beneficial health effects such as a protective effect on the development of cardiovascular diseases, inflammatory symptoms (rheumatoid arthritis and ulcerative colitis), atopic dermatitis, psoriasis and malignant diseases [4, 5]. In our search to find new source s of EFAs, we have investigated about one hundred oils from plant seeds in previous studies [6‐9]. Therefore, we aimed to determine the fatty acid composition of the seed oil of Z. fabago in this study. Mature plant seeds were collected from the vicinity of Ankara, Turkey in the natural habitats of the plants in September 2002. The plants were identified by M. Vural, Ph.D. A voucher specimen (GUE 2312) was kept in the Herbarium of the Faculty of Pharmacy, Gazi University (GUE), Ankara, Turkey. Seeds were weighed accurately and powdered with anhydrous Na 2 SO 4 . They were extracted with petroleum ether (bp 40‐60°C) in a Soxhlet apparatus, and the fatty acids were later converted to methyl esters with a Boron trifluoride-methanol complex (20%) reagent [10]. The methyl esters of fatty acids were dissolved in CH 2 Cl 2 and applied into a GC-MS apparatus (Hewlett Packard Model 6890 series) equipped with a mass selective detector. Experimental conditions for capillary GC-MS analysis were developed under the following conditions. Capillary column HP-5MS (5% phenylmethylsiloxane, 30 m × 250 μm, i.d., with 0.25 μm film thickness, model No. HP 190915-433), detector temperature 280°C, injector temperature 250°C, carrier gas helium (1 mL/min), split ratio 1/20, injection volume 0.2 mL, and mass range m/z 20‐440. GC oven temperature was kept at 180°C for 5 min and programmed to 280°C at a rate of 2°C/min and kept constant at 280°C for 10 min. Identification of the peaks was carried out through a Wiley library databank search as well as comparison with the standards. The relative percentage amounts of the separated fatty acids were calculated from total ion chromatography by a computerized integrator. Data obtained from three analyses of the seed oil were expressed as means (±SD). In this study, seed oil was obtained at an average yield of 3.7%. The composition of the fatty acids of the seed oil and their relative percentages are given in Table 1. The major constituents of the oil were unsaturated fatty acids. The total unsaturated acid content was 72.58%. The main component was linoleic acid (51.02%), followed by oleic acid (21.56%). When we compared the saturated fatty acids, the amount of palmitic acid (8.34%) was higher than the others such as stearic (4.88%), arachidic (1.41%), and behenic acid (1.05%). In conclusion, according to the results obtained by capillary GC-MS analysis, Z. fabago seed oil could be considered