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From the aerial parts of Teucrium creticum L. (Lamiaceae) eight compounds, 1 – 8 were isolated using chromatographical methods. Based on the results of spectroscopical analysis such as UV, 1D-NMR (1H-, 13C-NMR, DEPT-135), 2D-NMR (COSY, HSQC, HMBC, NOESY) and HRMS, the structure of the compounds were determined as two iridoids, 8-O-acetylharpagide (1) and teuhircoside (2), two phenylethanoid glycosides, verbascoside (= acteoside) (3) and lavandulifolioside (4), and four neoclerodane-type diterpenoids, teucrin H3 (= 19-acetylgnaphalin) (5), teucjaponin B (6), teucretol (7) and diacetylteumassilin (8).

The aim of the present study is to determine the potent biological activities and carry out isolation studies on Barbarea integrifolia. The antioxidant capacity of the species was evaluated by total phenolic content, FRAP, CUPRAC, and DPPH radical scavenging activity. Anticancer activity studies were performed by MTT assay in MDA-MB-231, MCF-7, Hep3B, PC-3, A549, HCT116, L-929 cell lines. It was observed that the remaining aqueous fraction has higher total phenolic content while higher activity in the CUPRAC and FRAP assays was displayed for the methanolic extract and chloroform fraction. The extracts showed anticancer activity as compared with vincristine. It was observed that chloroform fraction has the highest anticancer activity on MCF-7 cell line, while ethyl acetate fraction has the highest anticancer activity on Hep-3B and A549 cell lines. Methanolic extract has the highest anticancer activity on HCT116 and MDA-MB-23 cell lines. The isolation studies have been performed using several chromatographic methods. The chemical structures of compounds have been identified by means of 1H NMR, 13C NMR, 2D-NMR, and MS. Five major compounds, one steroid (β-Sitosterol), one phenolic acid (Rosmarinic acid), one flavonol heteroside (kaempferol 7-O-α-l-rhamnoside-3-O-β-d-(2-O-β- d -glucosyl)-β-d-glucoside), and two glucosinolates (Gluconasturtiin, Gluconasturtiin choline salt) have been isolated.

Objectives Mesenchymal stem cells are self-renewing stem cells. The human foreskin has potential to be used as a source of stem cells. The aim of the study was to obtain spheroid formation of human foreskin cells (hnFSSCs) isolated from newborn human foreskin tissue. In addition, the apoptotic and proliferative effects of a traditional plant, Corchorus olitorius L. (C. olitorius), on hnFSSC spheroids were investigated. Materials and methods After a routine circumcision procedure the cells were isolated and cultured in suitable medium. The plant leaves was extracted with ethanol and their composition was analyzed by liquid chromatography coupled with mass spectrometry (LC-MS/MS). The foreskin stem cells were characterized immunocytochemically by CD45, CD34, and CD90 antibodies. hnFSSC spheroids were formed using the hanging drop technique. Immunofluorescence staining was used on the obtained spheroids to determine the distribution of caspase-3 and Ki-67 after being treated with C. olitorius extract for 48 h. Results Immunostaining analysis showed that hnFSSCs were positive for CD45 and CD34 and negative for CD90. According to LC-MS/MS C. olitorius was rich in flavanols and hydrocinnamic acid derivatives. Although the spheroids obtained were loose and floating, the cells interacted with each other. Caspase-3 activity was higher in the control group than in the extract-treated group and Ki-67 was higher in the extract-treated group than in the control group, suggesting that the plant might have the capacity to increase stem cell proliferation due to its rich polyphenolic content. Conclusion The results suggest that hnFSSCs and spheroids might be used in stem cell generation, tissue repair and renewal as human foreskin tissue has potential to be used as a stem cell source. C. olitorius also increased proliferation of hnFSSCs, showing that polyphenols might increase proliferation of stem cells.

OBJECTIVES: Verbascoside, also known as acteoside/kusaginin, has attracted a great attention due to its pharmacological features. In this study, we aimed to determine the cytotoxic effects of pure verbascoside isolated from Phlomis nissolii L. plant in both MCF-7 and MDA-MB-231 cell lines in vitro. MATERIALS AND METHODS: MCF-7 and MDA-MB 231 cells were treated with verbascoside (100, 48, 25, 10, 1, 0.5, and 0.1 μM) for 24, 48, and 72 hours. Cytotoxic effect of verbascoside in MCF-7 and MDA-MB-231 cells was assessed using TEBU-BIO cell counting kit 8. RESULTS AND CONCLUSION: IC(50) values for 24, 48, and 72 h verbascoside exposure of MCF-7 cells were determined as 0.127, 0.2174, and 0.2828 μM, respectively. R(2) values were calculated as 0.9630, 0.8789 and 0.8752, respectively. Two-Way ANOVA multiple comparison test results showed that 100 μM verbascoside has the highest cytotoxic effect on MCF-7 breast cancer (BC) cells after 72 h of exposure. IC(50) values for 24, 48 and 72 h verbascoside exposure of MDA-MB 231 cells were determined as 0.1597, 0.2584 and 0.2563 μM, respectively and R(2) values were calculated as 0.8438, 0.5107 and 0.9203, respectively. Two-Way ANOVA multiple comparisons test results showed that 100 μM verbascoside has the highest cytotoxic effect on MDA-MB 231 BC cells after 24, 48 and 72 h of exposure.

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WOS: 000499103400003, Non-polar and polar compounds were isolated from the leaves and chemical composition of the essential oil from aerial parts of Sideritis cypria endemic in Northern Cyprus was also determined. the structures of all the isolated compounds were elucidated by means of spectroscopic (UV, NMR: 1D and 2D-NMR: H-1, C-13, COSY, HSQC, HMBC) methods and comparison with literature data. the essential oil composition of the plant material was analysed by GC-FID and GC-MS, simultaneously. To the best of our knowledge, secondary metabolites of this endemic species were determined for the first time. As a result, two mixtures of four entkaurane diterpenes; sidol (1) and isosidol (2), linearol (3) and isolinearol (4); four phenylethanoid glycosides; verbascoside (5), lavandulifolioside (6), leonoside A (7), leucoseptoside A (8); four flavone glycosides, apigenin-7 -O-glucopyrano side (9), isoscutellarein-7 -O[6'''-O-acetyl-allopyrano syl -(1 -> 2)-glucopyrano side] (10) and a mixture of apigenin-7-O-(4 ''-O-p-coumaroyl)-glucopyranoside (11) and apigenin-7-O-(3 ''-O-p-coumaroyl)-glucopyranoside (12) were elucidated. 7-O-acetyl-8-epi-loganic acid (13), an iridoid glycoside, was reported herein for the first time for genus Sideritis. in addition, major compounds of the essential oil were determined as alpha-pinene (14.73 +/- 0.15%), beta-pinene (16.60 +/- 0.20%), beta-phellandrene (17.83 +/- 0.23%) and epi-cubebol (7.70 +/- 0.20%), respectively., Near East University, Experimental Health Sciences Research Center [SAG-1-2016-044], This work is a part of PhD thesis supported by Near East University, Experimental Health Sciences Research Center [Project No: SAG-1-2016-044]. the authors thanks to Anzarulhaqur Anwarulhaqur, Dr. for NMR spectroscopy and Mohammed Ayman Salkini for HRLCMS-MS measurements from Prince Sattam Bin Abdulaziz University, College of Pharmacy.

The aerial parts of Chrysophthalmum montanum (DC.) Boiss. (Asteraceae) is traditionally used for wound healing, as well as for the treatment of common cold, sinusitis, and other inflammatory diseases. The objectives of this study were to identify potential anti-inflammatory effects of the methanol extract, and its different polarity subextracts (n-hexane, chloroform, n-butanol, and remaining aqueous), and guaianolide-type sesquiterpene lactones [6α-acetoxy-4α-hydroxy-1βH-guaia-9.11(13)-dien-12.8α-olide (1), 6α-acetoxy-4α-hydroxy-9β.10β-epoxy-1βH-guaia-11(13)-en-12.8α-olide (2), 4α,6α-dihydroxy-1β,5α,7αH-guaia-9(10),11(13)-dien-12,8α-olide (3), and (4α,5α,8β,10β)-4,10-dihydroxy-1,11(13)-guaidien-12,8-olide (4)] from the aerial parts of C. montanum. In order to evaluate the anti-inflammatory activity of C. montanum, carrageenan- and PGE2-induced hind paw edema, and acetic acid-induced increase in capillary permeability mice models were used. The methanol extract, the chloroform subextract, and compounds 3, and 4 were shown to possess anti-inflammatory activity in in vivo models at 100 mg/kg dose. The results provide a biological, and phytochemical basis for the traditional use of C. montanum aerial parts for inflammatory conditions in Turkish folk medicine.

Objectives Hydatid disease is a parasitic disease caused by Echinococcus granulosus and is still endemic in many parts of the world. Scolicidal solutions are generally used in any type of intervention, either surgical or percutaneous, to neutralize the cyst contents, although completeness of their effect is obscure and solid evidence is scarce. On the other hand, the use of these scolicidal solutions is not devoid of complications and many serious complications such as caustic sclerosing cholangitis may be seen in relation with their usage. Recent investigations proved protoscolicidal properties of olive leaf extract although the active ingredient has not been attributed to any component. The aim of this experimental study was to isolate oleuropein and test for in vitro protoscolicidal activity. Material and methods Oleuropein, a phenolic compound found in olive leaves, is extracted and prepared in different concentrations. Echinococcal cyst containing livers of sheep are obtained from the government slaughterhouse. Cysts were punctured and live protoscolex suspensions were prepared under aseptic conditions. Different concentrations of oleuropein solutions were prepared and protoscolicidal property is analyzed and compared with positive and negative controls for different exposure times. Results Oleuropein 2% concentration was found to be protoscolicidal in all exposure times starting from 5 minutes. Conclusion 2% oleuropein is a powerful, natural protoscolicidal agent which should be evaluated clinically before its application in routine treatment practice.

As the sixth-largest Angiosperm family, Lamiaceae contains more than 245 genera and 7886 species that are distributed worldwide. It is also the third-largest family based on the number of taxa in Turkey where it is represented by 46 genera and 782 taxa with a high endemism ratio (44%). Besides, Lamiaceae are rich in plants with economic and medicinal value containing volatile and nonvolatile compounds. Many aromatic plants of Lamiaceae such as Salvia, Sideritis, Stachys, Phlomis, and Teucrium species are used in traditional herbal medicine throughout Turkey as well as in other Mediterranean countries. Salvia (Sage tea “Adaçayı”), Sideritis (Mountain tea “Dağçayı”), Stachys (Hairy Tea “Tüylü Çay”), and Phlomis (Turkish sage “Çalba or Şalba”) are the largest genera that are used as herbal teas. This review focuses on the volatile and nonvolatile compounds of Lamiaceae from the genera Phlomis and Eremostachys of the subfamily Lamioideae with emphasis on iridoids, phenylethanoid glycosides, and essential oils.

Cholinesterase (ChE) inhibition is an important treatment strategy for Alzheimer’s disease (AD) as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) are involved in the pathology of AD. In the current work, ChE inhibitory potential of twenty-four natural products from different chemical classes (i.e., diosgenin, hecogenin, rockogenin, smilagenin, tigogenin, astrasieversianins II and X, astragalosides I, IV, and VI, cyclocanthosides E and G, macrophyllosaponins A-D, kokusaginin, lamiide, forsythoside B, verbascoside, alyssonoside, ipolamide, methyl rosmarinate, and luteolin-7-O-glucuronide) was examined using ELISA microtiter assay. Among them, only smilagenin and kokusaginine displayed inhibitory action against AChE (IC50 = 43.29 ± 1.38 and 70.24 ± 2.87 µg/mL, respectively). BChE was inhibited by only methyl rosmarinate and kokusaginine (IC50 = 41.46 ± 2.83 and 61.40 ± 3.67 µg/mL, respectively). IC50 values for galantamine as the reference drug were 1.33 ± 0.11 µg/mL for AChE and 52.31 ± 3.04 µg/mL for BChE. Molecular docking experiments showed that the orientation of smilagenin and kokusaginine was mainly driven by the interactions with the peripheral anionic site (PAS) comprising residues of hAChE, while kokusaginine and methyl rosmarinate were able to access deeper into the active gorge in hBChE. Our data indicate that similagenin, kokusaginine, and methyl rosmarinate could be hit compounds for designing novel anti-Alzheimer agents.

Mathematical modeling is a key tool in understanding complicated behavior of large signal transduction networks. In this paper a mathematical model is developed to understand the complex signaling behavior of induced apoptosis in Colo-320 and Colo-741 cell lines. The model studies the intrinsic pathway of apoptosis induced by Apaf-1, Cyt-c, and Caspase 3. Experimentally these tests were carried out five times for three groups; namely Control, DCM and Aqueous groups. The main aim is to compare the rate of the occurrence of apoptosis in the two cells Colo-320 and Colo-741 using experimental data. Numerical results reveal that apoptosis takes place at the same time in DCM for Colo-320 and Colo-741, but slightly faster in Aqueous group for Colo-320. It was observed that it took place between the 5–7th h in all the cases.

Dispersive liquid-liquid microextraction (DLLME) was combined with high-performance liquid chromatography-diode-array detector (HPLC-DAD) for the extraction and quantitation of three major capsaicinoids (i.e. capsaicin, dihydrocapsaicin and nordihydrocapsaicin) from pepper (Capsicum annuum L.). Chloroform (extraction solvent, 100 μL), acetonitrile (disperser solvent, 1250 μL) and 30 s extraction time were found optimum. The analytes were back-extracted into 300 μL of 50 mM sodium hydroxide/ methanol, 45/55% (v/v), within 15 s before being injected into the instrument. Enrichment factors ranged from 3.3 to 14.7 and limits of detection from 5.0 to 15.0 µg g-1. Coefficients of determination (R2) and %RSD were higher than 0.9962 and lower than 7.5%, respectively. The proposed method was efficiently applied for the extraction and quantitation of the three capsaicinoids in six cultivars of Capsicum annuum L. with percentage relative recoveries in the range of 92.0%-108.0%. DLLME was also scaled up for the isolation of the three major capsaicinoids providing purity greater than 98.0% as confirmed by liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR) analysis, which significantly reduced the extraction time and organic solvent consumption.

In addition to two known ecdysteroids, 20-hydroxyecdysone and turkesterone, three previously undescribed stigmastane-type ecdysteroids were isolated from the underground parts of Rhaponticum acaule (L.) DC. by chromatographic techniques (CC, VLC, MPLC). The structures of the compounds were established by chemical (acetylation) and spectroscopic methods including UV, IR, HRMS, 1D-NMR: 1H-NMR, 13C-NMR, DEPT-135. and 2D-NMR: COSY, NOESY, HSQC, HMBC. Two compounds were isolated as an isomeric mixture and each of them was purified and converted to the corresponding acetylated derivative. Based on all of the evidence, the structures of three undescribed stigmastane-type ecdysteroids were established as 2β,3β,11α,20β,22α,24,28-heptahydroxy-6-oxo-stigmast-7-en-25,29-lactone and the cyclic 22,29-hemiacetals 22R and 22S stigmast-7-en-29-al,2β,3β,11α,20α,22,28-hexahydroxy-6-oxo, and the trivial names acaulesterone and rhapocasterones A and B are suggested, respectively. The structures and absolute configurations of 20-hydroxyecdysone and cyclic-22,29-hemiacetal-22R-stigmast-7-en-29-al,2β,3β,11α,20α,22,28-hexahydroxy-6-oxo were confirmed by X-ray crystal-structure analyses of their acetyl derivatives.

WOS: 000461670400003, Essential oils of the leaves and flowers of Phlomis cypria and P. brevibracteata were isolated by hydrodistillation and analysed by GC and Gas chromatography - mass spectroscopy (GC-MS), simultaneously. Essential oil yields of the four samples ranged between 0.07% and 0.09% (v/w). The essential oils of leaves (L) and flowers (F) of P. brevibracteata were found to be rich in -caryophyllene (L: 21.9%, F: 24.2%) and caryophyllene oxide (L: 26.0%, F: 7.2%). Main constituents of the essential oils of P. cypria leaves (L) and flowers (F) were determined as -caryophyllene (L: 37.4%, F: 20.8%) and germacrene D (L: 47.7%, F: 17.2%)., Near East University, Experimental Health Sciences Research Center [SAG-1-2016-043], This work was supported by the Near East University, Experimental Health Sciences Research Center [SAG-1-2016-043].

S. grandis Freitag, Vural & N. Adiguzel is an endemic plant species to Turkey. Since some other Salsola species have been reported to exert cholinesterase inhibitory effect, we aimed to investigate its inhibitory potential against AChE. The EtOH extract and thirteen constituents [ ten flavonol derivatives; e.g. isorhamnetin-3-O-rutinoside (1), quercetin-3-O-rutinoside (2), quercetin-3-O-metylether (3), tiliroside (4), isorhamnetin-3-glucuronide (5), isorhamnetin-3-O-glucoside (6), quercetin-3-O-galactoside (7), quercetin-3-O-rhamnoside (8), quercetin (9), and manghaslin (10), two oleanane-type saponosides; e. g. momordin II b (11) and IIc (12) as well as one amino acid derivative, N-acetyltryptophan (13)] isolated from the aerial parts of Salsola grandis (Chenopodiaceae) were tested for their possible inhibitory activity against acetylcholinesterase (AChE), related to pathogenesis of Alzheimer's disease. Although the EtOH extract was inactive, among the isolated compounds, only compound 13 exerted a notable inhibition of 64.90 +/- 1.61% at 50 mu g mL (1), while compound 12 displayed a low inhibition (21.72 +/- 0.99%). Then, compound 13 was further subjected to molecular modeling experiments in order to give insights about its interactions at atomic level with AChE. The data indicated that N-acetyltryptophan (13) could be a promising model molecule for AD treatment. a 2016 Phytochemical Society of Europe. Published by Elsevier Ltd. All rights reserved.

Switchable-hydrophilicity solvent liquid-liquid microextraction and dispersive liquid-liquid microextraction were compared for the extraction of piperine from Piper nigrum L. prior to its analysis by using high-performance liquid chromatography with UV detection. Under optimum conditions, limits of detection and quantitation were found as 0.2-0.6 and 0.7-2.0 μg/mg with the two methods, respectively. Calibration graphs showed good linearity with coefficients of determination (R2 ) higher than 0.9962 and percentage relative standard deviations lower than 6.8%. Both methods were efficiently used for the extraction of piperine from black and white pepper samples from different origins and percentage relative recoveries ranged between 90.0 and 106.0%. The results showed that switchable-hydrophilicity solvent liquid-liquid microextraction is a better alternative to dispersive liquid-liquid microextraction for the routine analysis of piperine in food samples. A novel scaled-up dispersive liquid-liquid microextraction method was also proposed for the isolation of piperine providing a yield of 102.9 ± 4.9% and purity higher than 98.0% as revealed by NMR spectroscopy.

Three undescribed sesquiterpene lactones (1-3), 1 beta,4 beta-dihydroxy-guaia-10(14),11(13)-dien-8 alpha,12-olide (1), 4 alpha, 6 alpha-dihydroxy-9 beta,10 beta-epoxy-1 beta H-guaia-11(13)-en-8 alpha,12-olide (2), and 4 alpha,9 beta-dihydroxy-6 alpha-acetoxy-1 beta H-guaia-10(14),11(13)-dien-8 alpha,12-olide (3), as well as a known sesquiterpene lactone, (4 alpha,5 alpha,8 beta,10 alpha)-4,10-dihydroxy-1,11(13)-guaiadien-12,8-olide (4), along with a lignan, pinoresinol (5), a flavonoid, chrysosplenol C (6), and two triterpenes, a mixture of isomers, taraxasterol acetate and Psi-taraxasterol acetate (7a/7b), and a mixture of isomers taraxasterol and Psi-taraxasterol (8a/8b) were isolated from the aerial parts of Chrysophthalmum montanum (DC.) Boiss. The structures of 1-6, 7a/7b, and 8a/8b were established on the basis of spectroscopic evidence, such as MS, NMR, UV, and IR spectroscopy. All isolated compounds, except for 5 and 8a/8b, were assayed for their antiproliferative activities against three human cancer cell lines, i.e. cervical (HeLa), breast (MCF-7), and lung (A549), and a normal human lung cell line (BEAS-2B) using MTT method. Compounds 1, 4, and 6 showed significant inhibitory effects on cancer cell growth at 20 mu g/mL concentration, with cell viability ranging from 53 to 64 % against MCF-7 cell line. In addition, compounds 4, and 6 exhibited cytotoxicity against HeLa cancer cell line with the viability of approximately 64 %. In conclusion, compounds 1, 4, and 6 may serve as leads for further research towards the development of anticancer agents.

Eight iridoid glucosides were reported from the aerial parts of Wendlandia ligustroides. 10-deoxygeniposidic acid (1), 7-deoxygardoside (2), geniposidic acid (3), 7-deoxy-8-epi-loganic acid (4), deacetyl-daphylloside (5), scandoside methyl ester (6), 6-O-methyl-deacetyl-daphylloside (7), 6-O-methyl-scandoside methyl ester (8). Compounds 3 – 8 were isolated as a pure form while 1 and 2 as a mixture. The structures of the compounds 1 – 8 were established by spectroscopic methods including 1D-NMR (1H NMR, 13C NMR, DEPT-135), 2D-NMR (COSY, NOESY, HSQC, HMBC) and HRMS.

This Corchorus olitorius L. isknown to be a medicinal plant widely consumed in the Eastern Mediterraneanregion and has anti-bacterial, anti-inflammatory and anti-cancer properties.Breast cancer has one of the highest mortality rates among all cancers.Therefore, the main aim of the study is to evaluate the effectiveness of C. olitorius plant on viability ofestrogen receptor (ER) positive breast cancer cell line, MCF-7. C. olitorius leaves first extracted withethanol, then LC-MS/MS analysis was done for identification of phytochemicals.MTT assay was used for assessment of cell viability of MCF-7 cells. Cells weretreated with C. olitorius extracts atfive concentrations (5, 10, 20, 50, 100 µg/ml) and four different incubationperiods (24, 48, 72, 96 h). LC-MS/MS analysis identified seven phytochemicalsin the extract, mainly quercetin and caffeoylquinic acid derivatives. MTTresults showed that the extract was only slightly effective in terms ofreduction of cell viability at 50 and 100 µg/ml doses which were incubated for24 and 48 h. Lower concentration doses did not show any effect in cellviability of MCF-7 cells. Longer incubation periods tend to increase cellviability of breast cancer cells. Quercetin identified within the extract might interfere with ER and promote MCF-7 cellproliferation. Therefore, in ER positive breast adenocarcinoma, quercetinintake and doses should carefully be monitored. More studies regarding therelationship between C. olitorius,quercetin and breast cancer should be done for further clarification of thetopic.

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, 6 alpha-acetoxy-4 alpha-hydroxy-113H-guaia-9.11(13)-dien-12.8a-olide (1), 6 alpha-acetoxy-4 alpha-hydroxy-9 beta.10 beta-epoxy-1 beta H-guaia-11(13)-en12.8 alpha-olide (2), 4 alpha,6 alpha-dihydroxy-1 beta H,5 alpha,7 alpha H-guaia-9(10),11(13)-dien-12,8 alpha-olide (3), and (4 alpha,5 alpha,8 beta,10 beta)-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 (FIT-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 (SEAS-2B), especially against HT-29 (IC50 = 12.2 pg/mL) compared to that of cisplatin. These results suggested that 4 is worthy of further study to determine its cytotoxicity mechanisms. Gazi University Research FoundationGazi University [02/2017-03]; Scientific and Technological Research Council of Turkey (TUBITAK) from TurkeyTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [2211/A, 2214/A]; International Center for Chemical and Bological Sciences (International Center for Chemical and Bological Sciences (ICCBS)-Hussain Ebrahim Jamal Research Institute of Chemistry from Pakistan This study was supported by Gazi University Research Foundation [grant number 02/2017-03],The Scientific and Technological Research Council of Turkey (TUBITAK) 2211/A and 2214/A, from Turkey, as well as International Center for Chemical and Bological Sciences (International Center for Chemical and Bological Sciences (ICCBS)-Hussain Ebrahim Jamal Research Institute of Chemistry from Pakistan. WOS:000463305000002 30580030 Q1

Officinal European Leonurus cardiaca, East Asian L. japonicus, and South African Leonotis leonurus are traditionally used for cardiovascular, gynecological, and neurological disorders. Nevertheless, a phytochemical assessment as a basis for their quality control and comparison amongst them has not yet been reported up to now. Here, a novel RP-HPLC method is presented for quantifying twelve phenolics, lavandulifolioside, verbascoside, hyperoside, ferulic acid, isoquercitrin, rutoside, apigenin-7-0-D-glucoside, and quercitrin, as well as chlorogenic, caffeic, rosmarinic, and cichoric acids, in 18 herbal and fruit samples of the three species, as well as in a L. cardiaca refined extract. Only ferulic acid was found in every sample, whereas rosmarinic acid and apigenin-7-0-D- glucoside were not detected in any sample. Chlorogenic, caffeic, and cichoric acids and rutoside were detected in all three species. Lavandulifolioside and verbascoside, the dominant phenolics of L. cardiac, were not present in any sample of L. japonicus. Lavandulifolioside was found in this first ever HPLC analysis on phenolics of L. leonurus. Hyperoside was not found in L. cardiaca, but in both L. japonicus and L. leonurus, whereas isoquercitrin was detected in L. cardiaca and L. leonurns, but not in L. japonicus. This approach facilitates identification and quality control via HPLC/HPTLC fingerprints.

Glutathione reductase (GR; E.C 1.6.4.2) catalyzes the reduction of oxidized glutathione to reduced glutathione by the nicotinamide adenine dinucleotide phosphate (NADPH) dependent mechanism. GR participates in the protection of the cell from the toxic effects of free radicals. In this study, we have investigated in vitro effects of isoorientin (C-glycosyl flavonoid), verbascoside, and forsythoside B (phenylethanoids) on purified bovine kidney cortex GR. These compounds present in many plant species that have been used as medicinal plants and have an interesting spectrum of biological activity. We have demonstrated that these compounds inhibit bovine kidney cortex GR in a concentration-dependent manner. Kinetic characterization of the inhibition is also done. Isoorientin is a noncompetitive inhibitor with respect to both glutathione disulfide (GSSG) (KiGSSG 0.023 ± 0.001 mM) and NADPH (KiNADPH 0.032 ± 0.001 mM). Forsythoside B acts as an uncompetitive inhibitor with respect to GSSG (KiGSSG 0.20 ± 0.014 mM) and NADPH (KiNADPH 0.267 ± 0.028 mM). Verbascoside acts as an uncompetitive inhibitor with respect to both GSSG (KiGSSG 0.242 ± 0.024 mM) and NADPH (KiNADPH 0.175 ± 0.016 mM). Inhibition of GR causes accumulation of reactive oxygen species and depletion of the glutathione pool. Inhibition of this enzyme may be significant in drug resistance.

The Sideritis species are widely used in the treatment of gastrointestinal disorders, rheumatism, cough, the common cold and as a diuretic, and they are commonly used as an herbal tea in folk medicine in Turkey. The teas of Sideritis have unique tastes, pleasant aromas and a transparent yellow colour, and are preferred as a hot beverage. In order to evaluate this information, the crude methanolic extract and the water soluble part of the methanolic extract after partition with chloroform and n-butanol were investigated for their anti-inflammatory and antinociceptive activities. Phytochemical studies performed on the n-butanol extract of the overground parts of Sidentis brevibracteata, which is rich in phenolic compounds with promising activities, resulted in the isolation of six acetylated allose containing 8-hydroxyflavone glycosides and a phenylethanoid glycoside. The structures of the compounds were established by spectroscopic evidence (UV, IR, NMR, MS). Furthermore, these phenolic compounds of S. brevibracteato were studied for anti-inflammatory, anti nociceptive, antioxidant and aldose reductase inhibitory activities. The experimental data demonstrated that S. brevibracteata displayed remarkable anti-inflammatory, antinociceptive and antioxidant activities. (C) 2009 Elsevier 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. © 2008 Elsevier Ireland Ltd. All rights reserved. This study is financially supported by The Scientific Research Fund of Gazi University.

From the leaves of Globularia alypum, three new phenylethyl glycosides, namely galypumosides A (=2-(3,4-dihydroxyphenyl)ethyl O-α-rhamnopyranosyl-(13)-4-O-[(E)-caffeoyl]-6-O-[(E)-p-coumaroyl]-β-glucopyranoside; 1), B (=2-(3,4-dihydroxyphenyl)ethyl O-α-rhamnopyranosyl-(13)-4-O-[(E)-caffeoyl]-6-O-[(E)-feruloyl]-β-glucopyranoside; 2), and C (=2-(3,4-dihydroxyphenyl)ethyl O-α-rhamnopyranosyl-(13)-4-O-[(E)-caffeoyl]-6-O-menthiafoloyl-β-glucopyranoside; 3), were isolated, together with two known phenylethyl glycosides, calceolarioside A and verbascoside. Eight iridoid glucosides, catalpol, globularicisin, globularin, globularidin, globularinin, globularimin, lytanthosalin, and alpinoside, a flavon glycoside, 6-hydroxyluteolin 7-O-sophoroside, a lignan glycoside, syringaresinol 4′-O-β-glucopyranoside, and a phenylpropanoid glycoside, syringin, were also obtained and characterized. The structures of the isolates were elucidated on the basis of 1D- and 2D-NMR experiments as well as HR-MALDI-MS.

Background Hepatocellular carcinoma is the second deadliest cancer with limited treatment options. Loss of PTEN causes the P13K/Akt pathway to be hyperactive which contributes to cell survival and resistance to therapeutics in various cancers, including the liver cancer. Hence molecules targeting this pathway present good therapeutic strategies for liver cancer. Hypothesis It was previously reported that Cardiac glycosides possessed antitumor activity by inducing apoptosis of multiple cancer cells through oxidative stress. However, whether Cardiac glycoside Lanatoside C can induce oxidative stress in liver cancer cells and induce cell death both in vitro and in vivo remains unknown. Methods Cell viability was measured by SRB assay. Cell death analysis was investigated by propidium iodide staining with flow cytometry and PARP cleavage. DCFH-DA staining and cytometry were used for intracellular ROS measurement. Protein levels were analyzed by western blot analysis. Antitumor activity was investigated on mice xenografts in vivo. Results In this study, we found that Cardiac glycosides, particularly Lanatoside C from Digitalis ferruginea could significantly inhibit PTEN protein adequate Huh7 and PTEN deficient Mahlavu human liver cancer cell proliferation by the induction of apoptosis and G2/M arrest in the cells. Lanatoside C was further shown to induce oxidative stress and alter ERK and Akt pathways. Consequently, JNK1 activation resulted in extrinsic apoptotic pathway stimulation in both cells while JNK2 activation involved in the inhibition of cell survival only in PTEN deficient cells. Furthermore, nude mice xenografts followed by MRI showed that Lanatoside C caused a significant decrease in the tumor size. In this study apoptosis induction by Lanatoside C was characterized through ROS altered ERK and Akt pathways in both PTEN adequate epithelial and deficient mesenchymal liver cancer cells. Conclusion The results indicated that Lanatoside C could be contemplated in liver cancer therapeutics, particularly in PTEN deficient tumors. This is due to Lanatoside C's stress inducing action on ERK and Akt pathways through differential activation of JNK1 and JNK2 by GSK3β. © 2015 Elsevier GmbH. © 2016 Elsevier GmbH. All rights reserved.

From the aerial parts of Eremostachys moluccelloides BUNGE, a new iridoid glucoside, lamalbidic acid (7). was isolated as its choline salt 7a together with six known iridoid glucosides, 5-deoxysesamoside (1). 6 ss-hydroxy-7-epiloganin (2), lamalbide (3), shanzhiside methyl ester (4), sesamoside (5), and 5-deoxypulchelloside 1 (6). The structures of 7a and 7 (obtained from 7a) were elucidated by spectroscopic (UV. IR, 1D- and 2D-NMR, and ESI-MS) methods.

WOS: 000245699500023, PubMed ID: 17125946, Lythrum salicaria (purple loosestrife) known as "Tibbi hevhulma" in Turkish is used for its several beneficial health effects against as diarrhea, chronic intestinal catarrh, hemorrhoid and eczema in the form of a decoction or a fluid extract and to treat varicose veins, bleeding of the gums, hemorrhoid and eczema, externally. Dried herbal parts of Lythrum salicaria L. (Lythraceae) were sequentially extracted with different solvents such as petroleum ether, ethyl acetate, methanol and 50% aqueous methanol. Water extract of Lythrum salicaria was also prepared under reflux. Antioxidant, anti-inflammatory and anti-nociceptive activities of all the extracts were investigated using in vitro and in vivo methods, respectively. Free radical scavenging activity (1,1-diphenyl-2-picrylhydrazyl, DPPH center dot assay), iron(III) reductive activity, capacity of the inhibition of linoleic acid peroxidation and MDA formation, anti-nociceptive activity (p-benzoquinone-induced abdominal constriction test) and anti-inflammatory activity (carrageenan-induced hind paw edema model) were used for all the extracts. In addition, the content of total phenolics, flavonoids and flavonols in all the extracts were determined with spectrophotometric methods. Results were compared with reference antioxidants via ascorbic acid, butylated hydroxytoluene, and gallic acid. Qualitative and quantitative compositions of all the extracts were analysed using a HPLC-PDA system. Polar fractions were found to be rich in flavonoids such as isovitexin and isoorientin

Two new iridoid glycosides, eriobioside (1) and lamerioside (2), were isolated from the aerial parts of Lamium eriocephalum subsp. eriocephalum, along with the two known compounds lamiide (3) and ipolamiide (4). Their structures were elucidated by spectroscopic methods (UV, 1D- and 2D-NMR) and by mass spectrometry (HR-ESI-MS).

The structures of six different iridoid glucosides have been revised. Three compounds isolated from Eremostachys glabra and designated 6,9-epi-8-O-acetylshanziside (1), 5,9-epi-penstemoside (2), and 5,9-epi-7,8-didehydropenstemoside (3) have been shown to be identical to the known iridoids barlerin (4, 8-O-acetylshanziside), penstemoside (5), and 7,8-didehydropenstemoside (6), respectively. Another compound named harpagoside-B, isolated from Scrophularia deserti and proposed to be 9-epi-6-O-methylharpagoside (11), was demonstrated from the spectroscopic data given to be the known harpagoside (10b). Finally, two alleged iridoid galactosides from Buddleja crispa named buddlejosides A and B (12a and 12b) have been shown to be the corresponding glucosides; the former is identical to agnuside (13a), while the latter is 3,4-dihydroxybenzoylaucubin (13b), an iridoid glucoside not previously published. This clearly showed that care should be taken with the interpretation of NOEs involving bridgehead protons in iridoid structures because they can be capricious and lead to erroneous structural assignments.

The water-soluble part of the methanolic extract from the aerial parts of Scrophularia crypthophila, through chromatographic methods, yielded three new resin glycosides, crypthophilic acids A - C (1-3). Compounds 1-3 are tetraglycosides of (+)-3S,12S-dihydroxypalmitic acid. The structures of these and 10 known compounds were elucidated by spectroscopic and chemical means. All natural resin glycosides known so far have been obtained from Convolvulaceae plants; this is the first report of such glycosides from another, taxonomically unrelated family (Scrophulariaceae).

The inhibitory effects of flavonoids on monoamine oxidases (MAOs) have attracted great interest since alterations in monoaminergic transmission are reported to be related to neurodegenerative diseases such as Parkinson’s and Alzheimer’s diseases and psychiatric disorders such as depression and anxiety, thus MAOs may be considered as targets for the treatment of these multi-factorial diseases. In the present study, four Sideritis flavonoids, xanthomicrol (1), isoscutellarein 7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (2), isoscutellarein 7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-6''-O-acetyl-β-D-glucopyranoside (3) and salvigenin (4) were docked computationally into the active site of the human monoamine oxidase isoforms (hMAO-A and hMAO-B) and were also investigated for their hMAO inhibitory potencies using recombinant hMAO isoenzymes. The flavonoids inhibited hMAO-A selectively and reversibly in a competitive mode. Salvigenin (4) was found to be the most potent hMAO-A inhibitor, while xanthomicrol (1) appeared as the most selective hMAO-A inhibitor. The computationally obtained results were in good agreement with the corresponding experimental values. In addition, the x-ray structure of xanthomicrol (1) has been shown. The current work warrants further preclinical studies to assess the potential of xanthomicrol (1) and salvigenin (4) as new selective and reversible hMAO-A inhibitors for the treatment of depression and anxiety.

From the aerial parts of Calendula arvensis a new triterpene saponin arvensoside C (1) was isolated together with four known triterpene saponins. The aglycon moieties had the oleanane skeleton for all of them. Three known flavonol glycosides, isorhamnetin 3-O-β -D-glucopyranoside, quercetin 3-O-β -D-glucopyranoside and quercetin 3-O-β -D-galactopyranoside were also obtained and characterized. Their structures were elucidated by 1D and 2D NMR experiments including 1D-TOCSY, DQF-COSY, HOHAHA, HSQC and HMBC spectroscopy as well as HRESIMS analysis.

Baibutoside (5), a new cycloartane-type triterpene glycoside, has been isolated from the roots of Astragalus baibutensis along with four known glycosides, acetylastragaloside I (1), and astragalosides I, II, and IV (2-4, resp.). The structure elucidation of the compounds were achieved by a combination of one- and two-dimensional NMR techniques (DQF-COSY, HSQC, HMBC, and ROESY), and mass spectrometry (ESI-MS), where all the compounds were shown to have cycloastragenol (=(20R,24S)-3beta,6alpha,16beta,25-tetrahydroxy-20,24-epoxy-9,19-cyclolanostane) as aglycone. All compounds were tested for in vitro antiprotozoal activity. Compounds 1-4 displayed notable activity vs. Trypanosoma brucei rhodesiense, with acetylastragaloside I (1) being the most potent (IC50 9.5 microg/ml). Acetylastragaloside I (1) was also lethal to T. cruzi (IC50 5.0 microg/ml), and it is the first cycloartane-type triterpene with remarkable trypanocidal activity against both T. brucei rhodesiense and T. cruzi. However, it exhibits some cytotoxicity on mammalian cells.

From the aerial parts of Phlomis tuberosa a new iridoid glucoside, chlorotuberoside was isolated together with five known iridoid glucosides, lamalbide, shanzhiside methyl ester, 7-epi-phlomiol (= phloyoside I), sesamoside and 5-deoxysesamoside. Two known phenylethanoid glycosides, forsythoside B, and decaffeoylacteoside, three known neolignan glycosides, dehydrodiconiferyl alcohol 9’-O-β -D-glucopyranoside, dihydrodehydrodiconiferyl alcohol 9-O-β -D-glucopyranoside and dihydrodehydrodiconiferyl alcohol 9’-O-β -D-glucopyranoside, one flavone glycoside, luteolin 7-O-β - D-glucopyranoside, as well as β -sitosterol 3-O-β -D-glucopyranoside and 1-methyl-O-β -D-glucopyranoside were also obtained and characterized. The structures of the isolates were elucidated on the basis of spectroscopic data. The three known phenylethanoid glycosides, verbascoside, leucosceptoside A and martynoside were identified by TLC comparison with authentic compounds.

This investigation evaluated the gastroprotective activity of Astragaloside IV, a cycloartane-type triterpene glycoside isolated from Astragalus zahlbruckneri. Gastric mucosal damage was induced in rats by intragastric ethanol (1 mL/rat). Rats treated orally with Astragaloside IV suspended in Tween 80 at 3, 10 and 30 mg kg−1, showed 15, 37 and 52% gastroprotection, respectively. The gastroprotection observed at 30 mg kg−1 for this compound was attenuated in rats pretreated with NG-nitro-l-arginine methyl ester (70 mg kg−1, i.p), a nitric oxide (NO)-synthase inhibitor, suggesting that the gastroprotective mechanism of this glycoside involves, at least in part, the participation of NO. The gastroprotective effect of Astragaloside IV was not affected by the inhibition of prostaglandin synthesis with indometacin (10 mg kg−1, s.c.) nor by the block of endogenous sulfhydryls with N-ethylmaleimide (NEM, 10 mg kg−1, s.c.). Carbenoxolone was used as a gastroprotective model drug and showed a dose-dependent gastroprotective effect (25, 43 and 88% of gastroprotection, at 3, 10 and 30 mg kg−1, respectively). The partial participation of prostaglandins, sulfhydryls and NO was observed in the gastroprotective mechanism of carbenoxolone.

The ethanolic root extract of Scrophularia lepidota, an endemic plant of the Turkish flora, has been investigated for its anti-protozoal and inhibitory effect towards plasmodial enoyl-ACP reductase (FabI), a key enzyme of fatty acid biosynthesis in Plasmodium falciparum. Chromatographic separation of the extract yielded 10 iridoids (1–10), two of which are new, and a known phenylethanoid glycoside (11). The structures of the new compounds were determined as 3,4-dihydro-methylcatalpol (8) and 6-O-[4″-O-trans-(3,4-dimethoxycinnamoyl)-α-l-rhamnopyranosyl]aucubin (scrolepidoside, 9) by spectroscopic means. The remaining metabolites were characterized as catalpol (1), 6-O-methylcatalpol (2), aucubin (3), 6-O-α-l-rhamnopyranosyl-aucubin (sinuatol, 4), 6-O-β-d-xylopyranosylaucubin (5), ajugol (6), ajugoside (7), an iridoid-related aglycone (10) and angoroside C (11). Nine isolates were active against Leishmania donovani, with the new compound 9 being most potent (IC50 6.1 μg/ml). Except for 4, all pure compounds revealed some trypanocidal potential against Trypanosoma brucei rhodesiense (IC50 values 29.3–73.0 μg/ml). Only compound 10 showed moderate anti-plasmodial (IC50 40.6 μg/ml) and FabI enzyme inhibitory activity (IC50 100 μg/ml). 10 is the second natural product inhibiting the fatty acid biosynthesis of Plasmodium falciparum.

The qualitative and quantitative determination of phenylethanoid glycosides in methanolic extracts of five species of the genus Phlomis (Lamiaceae) has been investigated using a new reversed-phase HPLC method combined with photodiode-array detection and electrospray/MS analysis. Forsythoside B, verbascoside, samioside, alyssonoside, isoverbascoside, leucosceptosides A and B and martynoside were detected. The quantification of the above constituents was performed using echinacoside as internal standard. Knowledge of the content of phenylethanoid glycosides contributes to the chemotaxonomy of the genus.

Anti-plasmodial activity-guided fractionation of Phlomis brunneogaleata (Lamiaceae) led to the isolation of two new metabolites, the iridoid glycoside, brunneogaleatoside and a new pyrrolidinium derivative (2 S,4 R)-2-carboxy-4-( E)- p-coumaroyloxy-1,1-dimethylpyrrolidinium inner salt [(2 S,4 R)-1,1-dimethyl-4-( E)- p-coumaroyloxyproline inner salt]. Moreover, a known iridoid glycoside, ipolamiide, six known phenylethanoid glycosides, verbascoside, isoverbascoside, forsythoside B, echinacoside, glucopyranosyl-(1--G (i)-6)-martynoside and integrifolioside B, two flavone glycosides, luteolin 7- O-beta- D-glucopyranoside ( 10) and chrysoeriol 7- O-beta- D-glucopyranoside ( 11), a lignan glycoside liriodendrin, an acetophenone glycoside 4-hydroxyacetophenone 4- O-(6'- O-beta- D-apiofuranosyl)-beta- D-glucopyranoside and three caffeic acid esters, chlorogenic acid, 3-O-caffeoylquinic acid methyl ester and 5- O-caffeoylshikimic acid were isolated. The structures of the pure compounds were elucidated by means of spectroscopic methods (UV, IR, MS, 1D and 2D NMR, [alpha] (D)) and X-ray crystallography. Compounds 10 and 11 were determined to be the major anti-malarial principles of the crude extract (IC (50) values of 2.4 and 5.9 micrograms/mL, respectively). They also exhibited significant leishmanicidal activity (IC (50) = 1.1 and 4.1 micrograms/mL, respectively). The inhibitory potential of the pure metabolites against plasmodial enoyl-ACP reductase (FabI), which is the key regulator of type II fatty acid synthases (FAS-II) in P. falciparum, was also assessed. Compound 10 showed promising FabI inhibiting effect (IC (50) = 10 micrograms/mL) and appears to be the first anti-malarial natural product targeting FabI of P. falciparum.

A new iridoid glycoside, sintenoside (1) and two new phenylethyl glycosides, globusintenoside (=2-(3,4-dihydroxyphenyl)ethyl-O-6-O-feruloyl-β-D-glucopyranosyl-(14)-α-L-rhamnopyranosyl-(13)-4-O-caffeoyl-β-D-glucopyranoside; 2) and 3′′′-O-methylcrenatoside (=1,2-O-[2-(3,4-dihydroxyphenyl)ethan-1,2-diyl]-3-O-α-L-4-O-feruloyl-rhamnopyranosyl-β-D-glucopyranose; 3) were isolated from the underground parts of Globularia sintenisii, along with three known iridoid glycosides, lytanthosalin, globularin, catalpol, and six known phenylethyl glycosides, verbascoside, isoverbascoside, leucoscepthoside A, plantainoside C, martynoside, and isocrenatoside. The structure elucidation of the isolated compounds was performed by spectroscopic methods (MS and 1D and 2D NMR).

The isolation and structure elucidation of two new oleanane-type triterpene glycosides, 29-(β-D-glucopyranosyloxy)-2α,3β,23-trihydroxyolean-12-en-28-oic acid (=(2α,3β,4α,29α)-29-(β-D-glucopyranosyloxy)-2,3,23-trihydroxyolean-12-en-28-oic acid; 1) and its C(20)-epimer, 30-(β-D-glucopyranosyloxy)-2α,3β,23-trihydroxyolean-12-en-28-oic acid (=(2α,3β,4α,29β)-29-β-D-glucopyranosyloxy)-2,3,23-trihydroxyolean-12-en-28-oic acid; 2), and a novel nortriterpene glycoside, (17S)-2α,18β,23-trihydroxy-3,19-dioxo-19(18[RIGHTWARDS ARROW]17)- abeo-28-norolean-12-en-25-oic acid β-D-glucopyranosyl ester (=(1R,2S,4aS,4bR,6aR,7R,9R,10aS,10bS)-3,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11-tetradecahydro-1-hydroxy-7-(hydroxymethyl)-3′,4′,4a,4b,7-pentamethyl-2′,8- dioxospiro[chrysene-2(1H),1′-cyclopentane]-10a-carboxylic acid β-D-glucopyranosyl ester; 3) from Phlomis viscosa (Lamiaceae) are reported. The structures of the compounds were asigned by means of spectroscopic (IR, 1D- and 2D-NMR, and LC-ESI-MS) and chemical (acetylation) methods.

Using thin-layer chromatography (TLC) bioautography, a total of 58 extracts from various organs (aerial parts, leaves, flowers, fruits, roots) of 16 Turkish plants were tested for their antibacterial, antifungal, acetylcholinesterase inhibitory, antioxidant, and radical scavenging activities. The hexane, CHCl3/CH2Cl2, water, and total MeOH extracts were used. No activity was observed against two Gram-negative bacteria (Escherichia coli and Pseudomonas aureginosa) and the yeast Candida albicans. However, 23 plant extracts, mostly the CHCl3/CH2Cl2 and H2O-solubles, inhibited the growth of all five Gram-positive bacteria tested, Micrococcus luteus, Bacillus subtilis, Bacillus cereus, Staphylococcus aureus, and Staphylococcus epidermidis. Of the active extracts, the CHCl3-soluble of the roots of Putoria calabrica (L. fil) DC (Rubiaceae) displayed the highest antibacterial potential. The majority of the CHCl3/CH2Cl2 crude extracts also appeared to inhibit acetylcholinesterase on TLC plates at 100 µg/spot concentration. Particularly active samples were the middle polarity extracts (CHCl3/CH2Cl2) of the leaves of Rhododendron smirnovii Trautv., R. ponticum L., and R. ungernii Trautv. (Ericaceae). β-Carotene, β-carotene/linoleic acid mixture, and 2,2-diphenyl-l-pieryhydrazyl (DPPH) solutions sprayed onto TLC plates were used for detecting antioxidant and radical scavenging properties of the crude extracts. Antioxidant and radical scavenging activities were found to be predominant in highly polar extracts. The water-solubles of all Rhododendron (Ericaceae) and Phlomis (Lamiaceae) species presented the most significant activity.

Two new phenylethanoid glycosides integrifoliosides A (2) and B (3), along with a known phenylethanoid glycoside alyssonoside (1) and a flavone glucoside chrysoeriol-7-O-β-ᴅ-glucopyranoside (4) were isolated from the aerial parts of Phlomis integrifolia. The structures of the new compounds were identified as 3,4-dihydroxy-β-phenylethoxy-O-β-ᴅ-apiofuranosyl- (1 →4)-α-ʟ-rhamnopyranosyl-(1 →3)-4-O-feruloyl-β-ᴅ-glucopyranoside (2) and 3-hydroxy-4-methoxy-β-phenylethoxy-O-β-ᴅ-apiofuranosyl-(154)-α-ʟ-rhamnopyranosyl-(1→3)-4-O-feruloyl-β-ᴅ-glucopyranoside (3), on the basis of spectroscopic (UV, IR, 1D- and 2D-NMR, and HR-FABMS) methods.

WOS: 000185928600005, PubMed ID: 14577621, From the underground parts of Thalictrum orientale Boiss., a new phenolic compound 1 was isolated in addition to one known cyanoglycoside, lithospermoside (2). For the structure elucidation of all compounds, 1D- and 2D-NMR techniques (DEPT, COSY, HMBC, HSQC) and MS (HR-MALDI) were used. The structure of the new compound was established as 2(4'-hydroxyphenyl)-nitroethane-4'-O-[beta-xylopyranosyl-(1-->6)-beta-glucopyranoside] (1).

From the methanolic extract of the underground parts of Globularia cordifolia, a new iridoid glycoside, 5-hydroxydavisioside (1) and a new bisiridoid glycoside, globuloside C (2) were isolated along with six known iridoid glycosides, aucubin, melampyroside, monomelittoside, globularifolin, alpinoside and asperuloside. The structures of the isolates were established by 1D and 2D NMR spectroscopy in combination with IR, UV and MS analyses.