Biological Activities and Chemical Compositions of Prangos platychlaena Boiss. Essential Oil and Fractions, Multivariate Statistical Analyses.

In this research, essential oil was obtained from the aerial parts of Prangos platychlaena Boiss. by hydrodistillation using a Clevenger-type apparatus, separated into fractions having different polarities by column chromatography. Both essential oil and the fractions were analyzed by GC-FID and GC/MS simultaneously. Nona-3,5-diyne-2-yl acetate (46%) and 3,5-nonadiyne (13.5%) were found to be the main constituents of the essential oil. While the main components of the n-hexane fraction were characterized as 3,5-nonadiyne (45.6%) and germacrene B (16.4%), the major components of the methanol fraction were found to be nona-3,5-diyne-2-yl acetate (59.6%) and 3,5-nonadiyne-2-ol (25.9%). In addition, principal multivariate statistical analyses were performed with principal component analyses and Venn diagram calculations, utilizing chemical compositions of the essential oil and the fractions. Furthermore, in vitro anti-inflammatory activities of the essential oil and the fractions were evaluated to correlate the chemical composition with the biological activity, and to the best of our knowledge, this study was performed for the first time in this aspect. LOX inhibitions of the essential oil, n-hexane, and methanol fractions were determined to be 70.98 ± 1.7, 67.10 ± 2.5, and 50.11 ± 4.8%, respectively. Preliminary initial findings of this study will be extended in the future with new biological assays.

Essential Oil Composition of Fruits of Eight Ferulago Species Growing in Türkiye and Multivariate Statistical Analyses.

In this study, the composition of the volatile oils obtained from the fruits of 8 Ferulago species (Ferulago cassia Boiss., F. isaurica Pesmen, F. humilis Boiss., F. macrosciadia Boiss. & Balansa, F. setifolia K.Koch, F. silaifolia (Boiss.) Boiss., F. syriaca Boiss., F. trojana Akalin & Pimenov) growing naturally in Türkiye were examined by means of GC/MS and GC-FID and α-pinene was determined to be present in the fruits of four species along with other monoterpenes as major components. Principal Component Analyses (PCA) and Hierarchical Cluster Analysis (HCA) was performed, utilizing ten major components in the eight essential oils. Also, a Venn diagram was used to demonstrate chemotaxonomical variations in the composition of the essential oils of eight Ferulago species.

Essential Oils of Ferulago glareosa Kandemir&Hedge Roots and Aerial Parts: PCA and HCA Analyses.

Ferulago glareosa Kandemir & Hedge. is an endemic species of the family Apiaceae for Turkey and has interesting morphological characteristics compared to the other members of the genus Ferulago Koch. In this study we investigated the essential oil compositions of the roots and aerial parts of F. glareosa for the first time and compared them with essential oil compositions of the roots and aerial parts of other species of the genus. In our study, major components of the essential oil of the roots were determined to be 2,3,6-trimethylbenzaldehyde (32.2 %), falcarinol (23.7 %), hexadecanoic acid (9.5 %) and 2,5-dimethoxy-p-cymene (5.9 %); and major components of the essential oil of the aerial parts were found to be α-pinene (33.7 %), p-cymene (14.8 %), γ-terpinene (13.2 %), (Z)-ß-ocimene (12.4 %) and terpinolene (8.2 %). The essential oil compositions of F. glareosa root compare with essential oils components in the literature differ varies greatly. Hierarchical Cluster Analysis (HCA) was performed with Minitab software, utilizing 8 major components in the published 20 literatures, as well as in this study. Principal Component Analyses (PCA) were used in order to demonstrate chemotaxonomical variations in the composition of the essential oils of Ferulago species.

The five Ferulago species inhibited cell proliferation and induced apoptosis of A549, MCF-7, PC3 and SW480 cancer cells in vitro.

In this study, it was aimed to evaluate the cytotoxic and apoptotic activities of ethanolic extracts prepared from the roots of 5 Ferulago species [F. humilis Boiss., F. macrosciadia Boiss. & Balansa, F. sandrasica Pesmen & Quézel, F. silaifolia (Boiss.) Boiss., F. trojana Akalin & Pimenov] on various human cancer cell lines. The cytotoxicity analyses against human lung (A549), breast (MCF-7), prostate (PC3) and colon (SW480) cancer cell lines were determined by MTT test; while the apoptotic effect was evaluated by Annexin V binding assay. All studied extracts showed concentration-dependent cytotoxic activity with an IC50 value ranging from 0.416 to 5.336 mg/mL. The studied Ferulago species significantly induced apoptosis of cancer cells, while F. macrosciadia had the highest apoptotic activity on MCF-7 cells with 21.79 ± 1.63% apoptotic cell population (p < 0.0001). In addition, felamedin and prantschimgin content of the extracts, which are common coumarins in Ferulago species, were evaluated by HPLC. According to HPLC analysis, the highest amount of felamedin content was found in F. trojana, while the highest content of prantschimgin was found in F. sandrasica among the studied Ferulago species. This preliminary research has revealed that the studied Ferulago species have promising effects on various cancer cell lines. Further studies are planned to determine the compounds responsible for the effect and underlying mechanism.

Cytotoxic Effects of Some Nepeta Species against Breast Cancer Cell Lines and Their Associated Phytochemical Properties.

Nepeta is one of the largest genera of the Lamiaceae family. Nepeta species are commonly employed in traditional medicine for a variety of ailments, as well as food additives. In addition, they also come to the fore with their rich phytochemical content. In the present study, the quantitative phytochemical content of methanolic extracts and infusions prepared from the aerial parts of 14 Nepeta taxa collected from Turkey and their cytotoxic effects on two breast cancer cell lines, MCF-7 and MDA-MB-231, were investigated by using the MTT (3-(4,5-dimethylthiazol-2-yl))-2,5-diphenyltetrazolium-bromide) test. According to HPLC-PDA analysis, N. racemosa methanolic extract had the highest ursolic acid content with 165.9 mg/g extract. Total sterol, total iridoid, and total triterpenoid content were determined to be greatest in the methanolic extracts of N. meyeri, N. trichocalyx and N. phyllochlamys. The MTT experiment demonstrated that certain Nepeta species suppressed the growth of MCF-7 and MDA-MB-231 cells in a dose-dependent manner. Statistical analysis revealed a strong correlation between the cytotoxic effects of the extracts and their triterpene content. In conclusion, the data obtained from this study are important in terms of forming a basis for advanced anticancer activity studies on breast cancer with Nepeta sp.

Anatomical and Phytochemical Characteristics of Different Parts of Hypericum scabrum L. Extracts, Essential Oils, and Their Antimicrobial Potential.

Hypericum (Hypericaceae) is a genus that comprises a high number of species around the world. In this study, the roots, aerial parts, flowers, fruits, and aerial parts with flowers from Hypericum scabrum were macerated separately by methanol and water and then fractionated by different solvents of, such as ethyl acetate, n-hexane, butanol, dichloromethane, aqueous residue sub-extracts, and ethnobotanical use. All the extracts, sub-extracts and essential oils of H. scabrum were investigated for the first time in detail for their antimicrobial, total phenolics, and antioxidant activities. Anatomical structures of the root, stem, leaf, upper and lower leaf surface, stamen, sepal, and petal of H. scabrum were examined. The biochemical layout of essential oils was determined by GC and GC/MS. The antioxidant activity was determined by free radical scavenging activity (by DPPH). Antimicrobial activity was applied against Candida albicans ATCC 10231, Escherichia coli ATCC 8739, Staphylococcus aureus ATCC 6538, Bacillus subtilis ATCC 19659, and C. tropicalis ATCC 750 using microdilution methods. The essentials of the aerial parts, flower, and fruit are characterized by the presence of monoterpene hydrocarbons, whereas roots oil include alkanes. The GC-FID and GC-MS analysis showed that major components of roots, aerial parts, flowers, and fruits oils were undecane (66.1%); α-pinene (17.5%), γ-terpinene (17.4%), and α-thujene (16.9%); α-pinene (55.6%), α-thujene (10.9%), and γ-terpinene (7.7%); α-pinene (85.2%), respectively. The aerial part sub-extracts indicated a greater level of total phenolics and antioxidant potential. The n-hexane sub-extracts (from aerial part, flower, and aerial part with flower) showed the best activity against B. subtilis, with 39.06 µg/mL MIC value. The presented research work indicates that H. scabrum can be a novel promising resource of natural antioxidant and antimicrobial compounds.

Morphology of pollen in Ferula genus (Apiaceae).

In this study, the pollen morphology of all Ferula species distributed throughout the country of Turkey was studied with light and scanning electron microscopy for the first time. The aim is to identify the pollen morphological characteristics of 23 Ferula species. The pollen is radially symmetrical, isopolar and tricolporate in all examined species. Pollen grains are prolate and perprolate with the polar axis ranging from 22.28 to 40.47 µm and the equatorial axis from 13.70 to 18.73 µm. Their polar shapes are triangular, triangular to subtriangular and circular to subcircular. Several types of exine ornamentations have been observed on pollen through the use of scanning electron microscopy. The dendrogram constructed by using Average Linkage of the examined data revealed two main groups. It was determined that some pollen characteristics are more useful for classification than others. In particular, P, E, the ratio of P/E (pollen shape) and ornamentation in the polar and equatorial views are the most valuable variables for discrimination the Ferula species.

Determination of natural phenolic compounds of Ferula longipedunculata Pesmen and assessment their antioxidant and anticholinesterase potentials.

The paper reports anticholinesterase and antioxidant activities of extracts, fractions from aerial parts, roots, flowers, fruits of Ferula longipedunculata Pesmen (Apiaceae). Phenolic content, antioxidant activities of samples were carried out using Folin-Ciocalteu, DPPH, TBA methods. Anticholinesterase activity was actualised through Ellman's method. The utmost and least total phenolic content were detected in root MeOH extract (36.4 mg GAE g-1 DW) and aerial part (23.74 mg GAE g-1 DW), respectively. Hexane fraction of root exhibited significant inhibition against AChE (37.99%) and BuChE (81.66%) at 20 µg/mL as well as remarkable antioxidant and anticholinesterase activities. However, investigations on roots will be substantial for improved usage of F. longipedunculata for pharmaceutical and food search needs.

The natural phenolic compounds and their antioxidant and anticholinesterase potential of herb Leiotulus dasyanthus (K. Koch) Pimenov & Ostr.

The presented work reports anticholinesterase and antioxidant activities of extracts, fractions from aerial parts, fruits, flowers, roots and isolated compounds of roots from Leiotulus dasyanthus (bergapten, pimpinellin, umbelliferone, quercetin, rutin and kaempferol). Phenolic contents, antioxidant activities of samples were carried out by Folin-Ciocalteu, DPPH, TBA methods. Anticholinesterase activity was evaluated by Ellman's method. The highest and lowest total phenolic content were detected in root MeOH extract (88.6 mg GAE g-1 DW) and aerial part (51.83 mg GAE g-1 DW), respectively. The highest antioxidant activity among isolated secondary metabolites got coumarins umbelliferone, bergapten and pimpinellin. Pimpinellin (66.55%) and umbelliferone (61.09%) demonstrated strong inhibition towards acetylcholinesterase and butyrylcholinesterase, respectively. Dichloromethane fraction of root demonstrated significant inhibition against AChE (49.66%) and BuChE (92.21%) at 20 µg/mL. Dichloromethane fractions of roots had a notableness antioxidant and anticholinesterase activities. The further studies on roots will be important for development use of this plant for pharmaceutical and food research needs.[Formula: see text].

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.

Comparison of the Essential Oils of Ferula orientalis L., Ferulago sandrasica Pesmen and Quézel, and Hippomarathrum microcarpum Petrov and Their Antimicrobial Activity.

OBJECTIVES: To determine the chemical composition and antimicrobial activity of the essential oils of the aerial parts of Ferula orientalis L., roots of Ferulago sandrasica Pesmen and Quézel, and aerial parts of Hippomarathrum microcarpum Petrov. MATERIALS AND METHODS: Essential oils were analyzed by gas chromatography and gas chromatography/mass spectrometry. The antimicrobial activity of the essential oils was determined by bioautography assay. RESULTS: α-Pinene (75.9%) and ß-pinene (3.4%) were the major components of the aerial parts of F. orientalis; with limonene (28.9%), α-pinene (15.6%), and terpinolene (13.9%) for F. sandrasica; and ß-caryophyllene (31.4%) and caryophyllene oxide (23.1%) for the aerial parts of H. microcarpum. Essential oils from the aerial parts of F. orientalis, the roots of F. sandrasica, and the aerial parts of H. microcarpum were active against Staphylococcus aureus and Candida albicans strains. However, essential oils were not active against Pseudomonas aeruginosa or Escherichia coli. CONCLUSION: The antimicrobial activities against S. aureus and C. albicans of these species may be attributed to the presence of the main components in the essential oils.

Effect of Extracts of the Aerial Parts and Roots from Four Ferulago Species on Erectile Dysfunction in Rats with Streptozotocin-Induced Diabetes.

OBJECTIVES: The extracts of Ferulago species are used as aphrodisiacs in Turkey and so we aimed to demonstrate in vivo and in vitro the relaxant effect of four Ferulago species' extracts on the corpus cavernosum (CC). MATERIALS AND METHODS: A total of 30 adult male Sprague Dawley rats were divided into control and diabetic groups. Diabetes was induced by a single intraperitoneal injection of 40 mg/kg streptozotocin. In vivo erectile responses were obtained by stimulation of the cavernosal nerves and repeated after intracavernosal injection of extracts in rats, and the data were expressed as intracavernosal pressure (ICP)/mean arterial pressure and total ICP. The relaxant and contractile responses of CC strips were analyzed in the presence or absence of extracts. RESULTS: The extracts were active in both control and diabetic rats. The extract-induced maximum relaxation responses (especially of methanol extract of the root of Ferulago bracteata) (98.30±2.6%) were decreased after incubation with L-NAME (44.8±1.8). ODQ, a soluble guanylate cyclase inhibitor, inhibited 77% of extract-induced maximum relaxation in the CC from the control rats. CONCLUSION: These species can be utilized in erectile dysfunction and may be an herbal alternative to synthetic drugs.

Cytotoxic, Phytotoxic and Insecticidal Activities of Chrysophthalmum montanum (DC.) Boiss.

OBJECTIVES: To investigate the in vitro cytotoxic, phytotoxic, and insecticidal activity of Chrysophthalmum montanum (DC.) Boiss. MATERIALS AND METHODS: The crude methanol (80%) extract of the aerial parts of C. montanum was fractionated to obtain n-hexane, chloroform, n-butanol, and remaining water fractions. The crude extract and subsequent solvent fractions of the plant were evaluated for their biological activities using screening bioassays such as cytotoxicity on brine shrimp lethality, phytotoxicity against Lemna minor L., and insecticidal activity against Rhyzopertha dominica and Tribolium castaneum. RESULTS: The cytotoxicity assay revealed that the crude extract, n-hexane, and chloroform fractions of the plant had positive lethality with LD50 values of 71.51, 126.62, and 75.95 µg/mL, respectively. The extract and its fractions, except for the remaining water fraction, showed phytotoxic activity, which was expressed as percentage growth regulation in a concentration-dependent manner. n-hexane and chloroform fractions in particular had 100% growth inhibition (GI) at 1000 µg/mL, followed by the n-butanol fraction (62.6% GI) and crude extract (40.0% GI) of the plant at the same concentration. Otherwise, all samples had no insecticidal activity against R. dominica and T. castaneum. CONCLUSION: This study demonstrates that C. montanum contains bioactive compounds related to potential biological activities such as cytotoxic and phytotoxic.

Phtytochemical Studies and Quantitative HPLC Analysis of Rosmarinic Acid and Luteolin 5-O-ß-D-Glucopyranoside on Thymus praecox subsp. grossheimii var. grossheimii.

Thymus praecox ssp. grossheimii (RONNIGER) JALAS var. grossheimii (Lamiaceae) is used as an herbal tea for cold, stomachache, cough, and infections in Turkey. There are no phytochemical studies on this species. We performed phytochemical studies and quantitative analysis of rosmarinic acid and luteolin 5-O-ß-D-glucopyranoside in the methanol extract of the plant. Several chromatographic methods were used for the isolation of major compounds. HPLC methods were applied for quantitative analysis of rosmarinic acid and luteolin 5-O-ß-D-glucopyranoside in the methanol extract. In this study, ursolic acid (1), oleanolic acid (2), methyl rosmarinate (3), ethyl rosmarinate (4), rosmarinic acid (5), luteolin 5-O-ß-D-glucopyranoside (6), and thymoquinol 2,5-O-ß-diglucopyranoside (7) were isolated from the aerial parts of the plant. The relative contents of rosmarinic acid and luteolin 5-O-ß-D-glucopyranoside in the extract were 15.2 and 57.8 mg/g of dry weight, respectively. Compounds isolated from this plant and the contents of rosmarinic acid and luteolin 5-O-ß-D-glucopyranoside provided reasonable evidence for the traditional usages of this plant.

Cytotoxic compounds from endemic Arnebia purpurea.

Phytochemical studies of the roots and aerial parts of endemic Arnebia purpurea S. Erik & H. Sumbul resulted in the isolation and characterization of four naphthoquinones [isovalerylalkannin (1), α-methyl-n-butanoyl alkannin (2), acetylalkannin (3), and alkannin (4)], a triterpene derivative [3-O-acetyl-oleanolic acid (5)], a steroid [ß-sitosterol (6)], three flavonoid glycosides [isorhamnetin-3-O-rutinoside (7), kaempferol-3-O-rutinoside (8), kaempferol 3-O-(5"-acetyl) apiofuranoside 7-O-rhamnopyranoside (9)] and a phenolic acid [rosmarinic acid (10)]. 3-O-Acetyl-oleanolic acid, isorhamnetin-3-O-rutinoside, kaempferol-3-O-mrutinoside, and kaempferol 3-O-(5"-acetyl) apiofuranoside 7-O-rhamnopyranoside are reported from an Arnebia species for the first time. Cytotoxic activities on L929 murine fibrosarcoma cell line of the isolated compounds were investigated using MTT assay. Naphthoquinones (1-4) showed intermediate cytotoxic activity in comparison with the standard, doxorubicin.

Antioxidant secondary metabolites from Geranium lasiopus Boiss. & Heldr.

Chromatographic studies on the EtOAc soluble portion of the MeOH extract of Geranium lasiopus led to the isolation of eight flavonoids (kaempferol (1), quercetin (2), quercetin 3-O-ß-glucopyranoside (3), quercetin 3-O-ß-galactopyranoside (4), kaempferol 3-O-α-rhamnopyranosyl-(1 → 6)-ß-glucopyranoside (5), quercetin 3-O-α-rhamnopyranosyl-(1 → 6)-ß-glucopyranoside (6), kaempferol 3-O-α-rhamnopyranosyl-(1 → 2)-ß-glucopyranoside (7) and quercetin 3-O-α-rhamnopyranosyl-(1 → 2)-ß-glucopyranoside (8)), two simple phenolic compounds (gallic acid (9) and its methyl ester (10)) and a hydrolysable tannin (pusilagin (11)). The structures of the compounds were elucidated by 1- and 2-dimensional NMR techniques ((1)H, (13)C, COSY, HMBC, HMQC) and ESI-TOF-MS spectrometry. Inhibitory effects on H(2)O(2)-induced lipid peroxidation in human red blood cells of the different extracts of G. lasiopus, as well as isolated compounds, were investigated. All tested compounds showed comparable or higher activity than that of ascorbic acid and trolox.

Cycloartane glycosides from Astragalus stereocalyx Bornm.

Six cycloartane-type triterpene glycosides were isolated from Astragalus stereocalyx along with six known cycloartane-type glycosides. Their structures were established by the extensive use of 1D and 2D-NMR experiments along with ESIMS and HRMS analysis. Three compounds are based on an aglycon characterized by the occurrence of an unusual hydroxyl group at position 20, whereas three other compounds are based on cycloasgenin C as aglycon, so far reported from Astragalus spp. All the compounds were tested for their cytotoxic activity against a number of cancer cell lines. One compound exhibited activity versus human cervical cancer (Hela) with an IC(50) value = 10 µM.