Chemical profile, antibacterial and antioxidant properties of Rubia tinctorum L. essential oils.

Plants have gained great importance. Secondary metabolites contribute to the drug discovery and development by their bioactive properties. Rubia tinctorum L. essential oil (EO) was obtained and analysed. Antioxidant and antibacterial activities were evaluated. The plant's EOs were obtained through steam distillation, and the compounds were identified using gas chromatography-mass spectrometry (GC-MS) analysis. DPPH free radical scavenging and ferric-reducing antioxidant power (FRAP) were employed to assess antioxidant activity. Total antioxidant capacity (TAC) was also presented. The disc diffusion method was employed for testing antibacterial activity. Cyclohexanone was identified as the predominant component in the EO, constituting 88.74% of the total composition. The EO did not show significant antioxidant capacity, while it demonstrated antimicrobial effect against Bacillus cereus ATCC 6633 (>13 mm of inhibition; 500 mg/mL) and Shigella ATCC 12022 (≥12 mm of inhibition; 500 mg/mL). R. tinctorum L. is new source of cyclohexanone.

Enhancement of yogurt functionality by adding Mentha piprita phenolic extract and evaluation of its quality during cold storage.

New functional food products with health benefits are currently in high demand among health-conscious consumers. The present research aims to improve the functional properties of yogurt by adding peppermint hydroethanolic extract (PHE) at different doses. The impact of PHE (0%, 2%, 4%, and 6%) on yogurt was studied for acidity, pH, organoleptic quality, antioxidant activity, lipid peroxidation, and fatty acid profile. The results revealed that PHE is rich in phenolic compounds, of which rosmarinic acid was the main one (339.88 mg/g lyophilized extract) and has considerable antioxidant potential, which remarkably (p < .01) increased antioxidant capacity in yogurt by over 39.51%, even at a low dose of 2%, giving the product better protection against lipid peroxidation and preserving its physicochemical and sensory quality. At 4%, PHE increased significantly (p < .01) the content of omega-3 fatty acids, notably alpha-linolenic acid, in fortified yogurt compared with the control, and reduced (p < .01) the ratio of omega-6/omega-3, which dropped from 5.21 to 4.11. It looks feasible to prepare a yogurt with health-giving properties by adding Mentha piperita hydroethanolic extract at a concentration of up to 4% as an alternative to synthetic antioxidants, which would also extend its shelf life.

Green synthesis of silver nanoparticles using Stachys spectabilis: Identification, catalytic degradation, and antioxidant activity.

Nanotechnology has become the focus of scientific research due to its widespread and effective use. Silver nanoparticles (AgNPs) were produced utilizing Stachys spectabilis, and their antioxidant effect and catalytic degradation of methylene blue were investigated. The structure of ss-AgNPs was clarified by spectroscopy. FTIR demonstrated the possible functional group responsible for reducing agents. The absorption at 498 nm in the UV-Vis measurement verified the nanoparticle structure. XRD measurement demonstrated the nanoparticles to be face-centered cubic crystalline structures. TEM image proved the nanoparticles as spherical, and the size was determined as 10.8 nm. The intense signals at 2.8-3.5 keV in EDX confirmed desired product. The observation of zeta potential at -12.8 mV indicated the stability of nanoparticles. The nanoparticles can degrade the methylene blue with 54% at 40 h. The antioxidant effect of extract and nanoparticles was performed by ABTS radical cation, DPPH free radical scavenging, and FRAP assay. Nanoparticles revealed excellent ABTS activity (4.42 ± 0.10) in comparison to the standard BHT (7.12 ± 0.10). ss-AgNPs may be a promising agent for the pharmacy.

assessment of antioxidant, neuroprotective, anti-urease and anti-tyrosinase capacities of leaves extracts.

OBJECTIVE: To characterize the chemical profile of methanolic crude extract and its fractions (Ethyl acetate, n-butanol and aqueous) using liquid chromatography-mass spectrometry (LC-MS) analysis, to evaluate their biological and pharmacological properties: antioxidant (1, 1-diphenyl-2-pycrylhydrazyl (DPPH), 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic) (ABTS), galvinoxyle free radical scavenging, reducing power, phenanthroline and ß carotene-linoleic acid bleaching assays), enzymes inhibitory ability against several enzymes [acetyl-cholinesterase (AChE), buthyrylcholinesterase (BChE), urease and tyrosinase]. METHODS: Secondary metabolites were extracted from Tamarix africana air-dried powdered leaves by maceration, the crude extract was fractionated using different solvents with different polarities (Ethyl acetate, n-butanol and aqueous). The amount of polyphenols, flavonoids and tannins (hydrolysable and condensed) were determined using colorimetric assays. A variety of biochemical tests were carried out to assess antioxidant and oxygen radical scavenging properties using DPPH, ABTS, galvinoxyle free radical scavenging, reducing power, phenanthroline and ß carotene-linoleic acid bleaching methods. Neuroprotective effect was examined against acetylcholinesterase and buthy-rylcholinesterase enzymes. The anti-urease and anti-tyrosinase activities were performed against urease and tyrosinase enzymes respectively. The extract's components were identified using LC-MS and compared to reference substances. RESULTS: The results indicated that Tamarix africana extracts presented a powerful antioxidant activity in all assays and exhibited a potent inhibitory effect against AChE and BChE as well as urease and tyrosinase enzymes. LC-MS analysis identified amount of eight phenolic compounds were revealed in this analysis; Apigenin, Diosmin, Quercetin, Quercetine-3-glycoside, Apigenin 7-O glycoside, Rutin, Neohesperidin and Wogonin in methanolic extract and its different fractions of Tamarix africana from leaves. CONCLUSIONS: Based on these findings, it is reasonable to assume that Tamarix africana could be considered as a potential candidate for pharmaceutical, cosmetics, and food industries to create innovative health-promoting drugs.

The preventive effects of Centaurea maroccana Ball. extract against oxidative stress induced by cisplatin in mice brains: in vitro and in vivo studies.

Since antiquity, Centaurea species have been used in folk medicine to treat several diseases owing to their potential biological activities that distinguish this genus such as antioxidant, anticancer, and anti-inflammatory effect. The current study aimed to investigate the possible neuroprotective effects of the n-butanol extract of Centaurea maroccana (BECM) against cisplatin (CP) induced neurotoxicity in mice. BECM's potential neuroprotective properties were studied in vitro and in vivo models. Male Swiss albino mice were orally received BECM (200 mg/kg) for 10 days before a single intraperitoneal injection of cisplatin (8 mg/kg). Vitamin E (100 mg/kg) was given daily by gavage as a positive control. In vitro results revealed that BECM inhibited lipid peroxidation (LPO) levels and acetylcholinesterase (AChE) activity. In vivo findings showed that BECM pretreatment was able to regulate lactate dehydrogenase (LDH) levels and to improve CP-induced cholinergic dysfunction by inhibiting AChE activity in mice brains. Moreover, BECM attenuated CP-provoked oxidative stress by suppressing LPO levels, increasing total antioxidant capacity (TAC) and enhancing the activities of antioxidant enzymes (catalase (CAT), superoxide dismutase (SOD), reduced glutathione (GSH), glutathione peroxidase (GPx) and glutathione S-transferase (GST)) in both brain cytosolic and mitochondrial fractions. The histological analysis exhibited neurotoprotective effect of BECM by protecting the cerebral cortex and reducing the histomorphological alterations resulted by cisplatin. Interestingly, our extract achieved neuroprotection comparable to vitamin E in most evaluated parameters. It appears that protective potency of BECM against CP-induced neurotoxicity could be related to its richness in polyphenols confirmed by liquid-chromatography tandem mass spectrometry analysis (LC-MS/MS).

Antiproliferative and cytotoxic effects of bioactive compounds isolated from Onosma bourgaei.

Onosma species have been used commonly for traditional medicine for years due to their bioactive compounds content. Onosma bourgaei aerial part was extracted with hexane and methanol successively. The methanol extract was subjected to chromatographic techniques to isolate allantoin (1), 3,4-dihydroxybenzaldehyde (2), luteolin-7-O-glucoside (3), apigenin-7-O-ß-glucoside (4), diosmetin-7-O-ß-glucoside (5), rosmarinic acid (6), and globoidnan A (7). The structure of isolated compounds were identified by spectroscopic techniques such as 1D-NMR, 2D-NMR, FTIR, and LC-TOF/MS/MS. Antiproliferative activity of extract and natural compounds were carried out using HeLa (human epithelial cervix adenocarcinoma, ATCC® CCL-2™), HT29 (human colorectal adenocarcinoma, ATCC® HTB38™), MCF7 (human mammary gland adenocarcinoma, ATCC® HTB22™), and A549 (human lung carcinoma, ATCC® CCL185™) cancerous cells and normal cells, FL (human epithelial amnion cell, ATCC® CCL62™). Lactate dehydrogenase (LDH) was performed for cytotoxicity. The compounds, 4, 6, and 7 displayed the strong antiproliferative activity against corresponding cell lines. Apigenin-7-O-ß-glucoside (4) revealed the excellent activity on HeLa, HT29, A549, and MCF6 cancer cell lines with the values of (IC50, µM) 167.3, 196.8 181.1, and 203.5, respectively, compared standard compound, cisplatin.

Synthesis and characterization of silver nanoparticles using curcumin: cytotoxic, apoptotic, and necrotic effects on various cell lines.

Nanostructures have distinctive chemical and physical features owing to their surface area and nanoscale size. In this study, silver nanoparticles were synthesized using curcumin, a medicinally valuable natural product. The structure of curcumin-mediated silver nanoparticles (c-AgNPs) was identified by extensive spectroscopic techniques. The maximum absorption was observed at 430 nm in UV-Vis spectrum. The crystal structure of c-AgNPs was identified by XRD. The morphology of the structure was determined by SEM image. The particle size was found as 51.13 nm. The functional groups of curcumin and c-AgNPs were established by FTIR spectroscopy. Cytotoxic activity of c-AgNPs was carried out using A549, DLD-1, and L929 with MTT assay. c-AgNPs revealed excellent activity on DLD-1 cell lines and A549 cell lines at 1.0 mg/mL concentration with the lethal effect of 80%. However, nanoparticles did not show the considerable effect on L929. Moreover, they induced apoptosis. Consequently, c-AgNPs are a promising material for anticancer drugs candidate.

Chemical composition, antioxidant, and antimicrobial activities of two essential oils from Algerian propolis.

This study aims to investigate the chemical composition, antioxidant, and antimicrobial activity of two essential oils (EOs) from Algerian propolis. The volatile constituents were analyzed by gas chromatography-mass spectrometry. Fifty components were identified from the oils. The major components were found to be: cedrol (17.0%), ß-eudesmol (7.7%), and α-eudesmol (6.7%) in EO of propolis from Oum El Bouaghi (EOPO) whilst α-pinene (56.1%), cis-verbenol (6.0%), and cyclohexene,3-acetoxy-4-(1-hydroxy-1-methylethyl)-1-methyl (4.4%) in EO of propolis from Batna (EOPB). The antioxidant properties of EOPO and EOPB were determined using 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonate) (ABTS•+) and cupric reducing antioxidant capacity (CUPRAC assays), respectively. Both EOs had more cupric ion reducing ability than scavenging ABTS•+ radicals. The antimicrobial potential of the two EOs against eight pathogens was assayed by the agar diffusion method and the mode of action was determined by microdilution assay. The results revealed that EOPB was bactericidal for all tested pathogenic bacteria and fungicidal for Candida albicans ATCC 10231, whereas, EOPO showed bacteriostatic effect against Escherichia coli O157:H7 and Pseudomonas aeruginosa ATCC27853 and fungistatic effect against C. albicans ATCC 10231. Thus, the obtained results suggest the important use of propolis EOs as preservative agents.

Chemical Composition, Acetylcholine Esterase and Anti-bacterial Activities of Essential Oils of Elaeosilenum thapsioides (Desf.) Maire from Algeria.

BACKGROUND: Traditionally, the Algerian medicinal plant Elaeosilenum thapsioides (Desf.) Maire has been used for many diseases. The present research work aims to explore the chemical and biological characterization of its essential oil. METHODS: The essential oils were obtained by hydrodistillation of different Elaeosilenum thapsioides (Apiaceae) aerial parts samples collected from two different regions (Mahouane and Megres) from Setif, Eastern Algeria. The chemical characterization of the obtained essential oils is reported here for the first time. Besides, they were evaluated for their in vitro Acetylcholinesterase (AChE) inhibitory activity involved in Alzheimer's disease using Ellman's spectrophotometric method. RESULTS: Additionally, their in vitro antimicrobial activity was assessed by the disc diffusion method. Both activities were performed at various oil concentrations. The GC/MS analysis of the essential oils from aerial parts (leaves, stems, flowers, and seeds) of E. thapsioides identified 47 constituents. Monoterpene hydrocarbons were the main components, ranging from 72.78 to 99.13%. Oxygenated monoterpenes and oxygenated sesquiterpenes ranged between 1.37 and 17.25% and 0.12 and 3.53% in essential oils from leaves and stems. Sesquiterpene hydrocarbons were present in small to large quantities in the essential oils of both populations, ranging from 0.69 to 13.44%. The presence of m-Methoxybenzyl isothiocyanate was recorded in stems essential oils from Mahouane and leaves essential oils from Merges, which was 9.73% and 3.72%, respectively. CONCLUSION: The stems essential oils obtained from plants collected in Mahouane showed the highest AChE inhibitory activity. The highest anti-bacterial activity was shown by the essential oil obtained from Megres leaves against Bacillus cereus ATCC 11778. The oils exhibited a moderate inhibitory activity in both tests.

Isolation, identification of secondary metabolites from Salvia absconditiflora and evaluation of their antioxidative properties.

Salvia absconditiflora Greuter & Burdet (Synonym Salvia cryptantha Montbret & Aucher ex Benth) has been used extensively for traditional medicine. The aerial of plant material was boiled in water then filtrated. The filtrate was partitioned with ethyl acetate and n-butanol sequentially to yield the ethyl acetate and n-butanol extract. A sample of water was lyophilized to yield the water extract. Ethyl acetate extract revealed the highest antioxidant activity and included the most phenolic compounds among the extracts. Hence, ethyl acetate extract was subjected to chromatographic techniques. Ursolic acid (1), crismaritin (2), luteolin (3), rosmarinic acid methyl ester (4), 3,4-dihydroxyl benzaldehyde (protocatechuic aldehyde) (5), caffeic acid (6), apigenin-7-O-ß-glucoside (7), rosmarinic acid (8) and luteolin-7-O-ß-glucoside (9) were isolated and the structures were elucidated by spectroscopic methods including 1D, 2D NMR, and LC-TOF/MS. Cirsimaritin (2), luteolin (3), rosmarinic acid methyl ester (4), rosmarinic acid (8), luteolin-7-O-ß-glucoside (9) displayed the considerable antioxidant activity.

Crystal structure and Hirshfeld surface analysis of 2-oxo-13-epi-manoyl oxide isolated from Sideritis perfoliata.

The title compound, C20H32O2 (systematic name: 3-ethenyl-3,4a,7,7,10a-penta-methyl-dodeca-hydro-9H-benzo[f]chromen-9-one), was isolated from Sideritis perfoliata. In the crystal, mol-ecules pack in helical supra-molecular chains along the 21 screw axis running parallel to the a axis, bound by C-H⋯O hydrogen bonds. These chains are efficiently inter-locked in the other two unit-cell directions via van der Waals inter-actions. Hirshfeld surface analysis shows that van der Waals inter-actions constitute the major contribution to the inter-molecular inter-actions, with H⋯H contacts accounting for 86.0% of the surface.

Screening of Norharmane from Seven Cyanobacteria by High-performance Liquid Chromatography.

BACKGROUND: Cyanobacteria, including pharmaceutically and medicinally valuable compounds attract the great attention lately. Norharmane (9H-pyrido (3,4-b) indole found in some cyanobacteria revealed a great number of biological effects. OBJECTIVE: Seven cyanobacteria were isolated and identified from Yesilirmak River and Gaziosmanpasa University Campus to determine the norharmane content. MATERIALS AND METHODS: Cyanobacteria collected from Tokat, Turkey were isolated and identified by morphologically. Norharmane (9H-pyrido [3,4-b] indole) quantities were presented for seven cyanobacteria, Chroococcus minutus (Kütz.) Nägeli, Geitlerinema carotinosum (Geitler) Anagnostidis, Nostoc linckia Bornet ex Bornet and Flahault, Anabaena oryzae F. E. Fritsch, Oscillatoria limnetica Lemmermann, Phormidium sp. Kützing ex Gomont, and Cylindrospermum sp. Kutzing ex E. Bornet and C. Flahault by high-performance liquid chromatography. RESULTS: The norharmane amount indicated for cyanobacterial culture media altered in a species-dependent kind in the range of 0.81-10.87 µg/g. C. minutus produced the most norharmane among the investigated cyanobacteria as 10.87 µg/g. CONCLUSION: Cyanobacteria could be an important source of norharmane as well as pharmaceutically valuable compounds. SUMMARY: Seven cyanobacteria were isolated and identified from Yesilirmak RiverQuantitative analysis of norharmane was executed on isolated cyanobacteriaFour cyanobecteria species included the norharmaneChroococcus minutus contained the most norharmane (10.87 µg/g). Abbreviations used: HPLC: High performance liquid chromatograph.

Bioassay-guided isolation and identification of antioxidant flavonoids from Cyclotrichium origanifolium (Labill.) Manden and Scheng.

BACKGROUND: Medicinal and aromatic plants play a significant role in drug discovery and development process. Flavonoids, revealing a wide spectrum of biological activities, extensively found in plants are important secondary metabolites. MATERIALS AND METHODS: Aerial parts of Cyclotrichium origanifolium were collected, dried, and boiled in water then extracted with hexane, ethyl acetate, and n-butanol. Total phenolic content, DPPH• scavenging activity, reducing power (FRAP) activity, and ABTS•+ scavenging activity assays were applied for all extracts. The ethyl acetate extract revealing the most antioxidant activity as well as including the highest phenolic contents was subjected to chromatographic techniques (column chromatography, sephadex LH-20, semipreparative HPLC) to isolate the active compounds. The structure of isolated compounds were elucidated by spectroscopic methods (1D NMR, 2D NMR, and LC-TOF/MS). RESULTS: Isosakuranetin (1), eriodictyol (2), luteolin (3), naringenin (4), and apigenin (5) were isolated and identified. All isolated flavonoids displayed the excellent antioxidant activity. CONCLUSION: The isolated flavonoids and also plant extract have potency to be a natural antioxidant. SUMMARY: Five flavonoids were isolated from Cyclotrichium origanifoliumIsolated compounds revealed the good antioxidant activityC. origanifolium has a potency to be used in food industries Abbreviations used: DPPH•: 1,1-diphenyl-2-picryl-hydrazyl free radical, ABTS•+: 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid), UV:Ultraviolet, DNA: Deoxyribonucleic acid, BHT: Butylated hydroxytoluene, BHA: Butylated hydroxyanisole, HPLC: High performance liquid chromatography.

Bioassay-guided isolation, identification of compounds from Origanum rotundifolium and investigation of their antiproliferative and antioxidant activities.

CONTEXT: Origanum (Lamiaceae) has been used in food and pharmaceutical industries. OBJECTIVE: Isolation and identification of bioactive compounds from Origanum rotundifolium Boiss. and investigation of their antiproliferative and antioxidant activities. MATERIALS AND METHODS: The aerial part of O. rotundifolium was dried and powdered (1.0 kg ±2.0 g) then extracted with hexane, ethyl acetate, methanol and water. Solvent (3 × 1 L) was used for each extraction for a week at room temperature. The aqueous extract was partitioned with ethyl acetate (3 × 1 L) to yield the water/EtOAc extract subjected to chromatography to isolate the active compounds. The structures of isolated compounds were elucidated by 1 D, 2 D NMR and LC-TOF/MS. RESULTS: Apigenin (1), ferulic acid (2), vitexin (3), caprolactam (4), rosmarinic acid (5), and globoidnan A (6) were isolated and identified. Globoidnan A (6), vitexin (3), and rosmarinic acid (5) revealed the excellent DPPH• scavenging effect with IC50 values of 22.4, 31.4, 47.2 µM, respectively. Vitexin (3) (IC50 3.6), globoidnan A (6) (IC50 4.6), apigenin (1) (IC50 8.9) and ferulic acid (2) exhibited more ABTS•+ activity than standard Trolox (IC50 13.8 µg/mL). Vitexin (3) revealed the most antiproliferative activity against HeLa, HT29, C6 and Vero cells lines with IC50 values of 35.6, 32.5, 41.6, 46.7 (µM), respectively. DISCUSSION AND CONCLUSION: Globoidnan A (6) has the most antioxidant effects on all assays. This has to do with the chemical structure of the compound bearing the acidic protons. Vitexin (3) could be a promising anticancer agent.

Bioactivity-guided isolation of flavonoids from Cynanchum acutum L. subsp. sibiricum (willd.) Rech. f. and investigation of their antiproliferative activity.

Cynanchum acutum L. subsp. sibiricum (Willd.) Rech. f. was extracted with hexane, acetone, methanol and water individually. A sample was heated in water then extracted with ethyl acetate. Among the extracts, the ethyl acetate extract exhibited the most antiproliferative activity, so isolation of bioactive compounds was carried out from this extract. A new compound, kaempferol-3-O-ß-xylopyranosyl-(1-2)-ß-rhamnopyranoside (1) along with five known compounds, quercetin-3-O-ß-xyloside (2), kaempferol-3-O-ß-glucoside (3), quercetin-3-O-ß-glucoside (4), kaempferol-3-O-ß-rhamnopyranoside (5), and kaempferol-3-O-ß-d-neohesperidoside (6) were isolated from ethyl acetate extract. The structures were elucidated by spectroscopic techniques, basically 1D NMR, 2D NMR and LC-TOF/MS. Antiproliferative effects of isolated compounds were determined by xCELLigence using the HeLa (human uterus carcinoma) cell lines. Compound 2 and compound 5 revealed the good antiproliferative activity against HeLa cell lines.

Crystal structure of 3,4a,7,7,10a-penta-methyl-3-vinyl-dodeca-hydro-1H-benzo[f]chromen-9-ol isolated from Sideritis perfoliata.

The asymmetric unit of the title compound, C20H34O2, contains two crystallographically independent mol-ecules (1 and 2) with similar conformations. In both mol-ecules, the cyclo-hexane rings adopt a chair conformation, while the oxane rings are also puckered. In the crystal, O-H⋯O hydrogen bonds connect adjacent mol-ecules, forming C(6) helical chains located around a 21 screw axis and running along the crystallographic a axis. The packing of these chains is governed only by van der Waals inter-actions. Semi-empirical PM3 quantum chemical calculations are in a satisfactory agreement with the structural results of the X-ray structure analysis. The absolute structure was indeterminate in the present experiment.

Chemical constituents and antiproliferative effects of cultured Mougeotia nummuloides and Spirulina major against cancerous cell lines.

In this study, the effect of Mougeotia nummuloides and Spirulina major on Vero cells (African green monkey kidney), C6 cells (rat brain tumor cells) and HeLa cells (human uterus carcinoma) was investigated in vitro. The antiproliferative effect of the methanol extract of M. nummuloides and S. major compared with 5-fluorourasil (5-FU) and cisplatin was tested at various concentrations using the BrdU Cell Proliferation ELISA. Both M. nummuloides and S. major extracts significantly inhibited the proliferation of Vero, HeLa and C6 cancer cell lines with IC50 and IC75 values. The M. nummuloides extract exhibited higher activity than 5-FU and cisplatin on Vero and C6 cells at high concentrations. The S. major extract revealed better antifproliferative activity than standards against Vero cells at 500 µg/mL. The compounds of methanol extracts were determined by GC-MS after the silylation process. Trehalose, monostearin and 1-monopalmitin were detected as major products in the M. nummuloides extract where as in the S. major extract; monostearin, 1-monopalmitin and hexyl alcohol were the main constituents.

Bioactivity-Guided Isolation of Antiproliferative Sesquiterpene Lactones from Centaurea solstitialis L. ssp. solstitialis.

Centaurea solstitialis L. ssp. solstitialis (CSS) has been used as medicine for various diseases. In this work, root, stem and flower parts of the plant were separately extracted with methanol to execute bioassay-guided isolation. Antiproliferative activities of each extracts on C6 cells (Rat Brain tumor cells) and HeLa cells (human uterus carcinoma) were investigated in vitro. The methanol extract of stem exhibited the most antiproliferative activity therefore isolation of active compounds was carried out for stem of the plant. Methanol extract of stem was boiled at 97 °C for 2 hours in water and then hexane and ethyl acetate were extracted sequentially. Solstitialin A 1 and 15-dechloro-15-hydroxychlorojanerin 2 were isolated from ethyl acetate extract by column chromatography and identified by spectroscopic techniques. Solstitialin A 1 was isolated from CSS and 15-dechloro-15-hydroxychlorojanerin 2 was isolated from Saussurea lipschitz and Rhaponticum pulchrum previously. These two compounds exhibited very high antiproliferative activity on C6 and HeLa cells. IC50 and IC75 values of compound 1 were obtained as 10.78 and 53.65 against C6 cell and as 48.78 and 68.52 against HeLa, respectively. IC50 and IC75 values of compound 2 were determined as 432.43 and 109.79 against C6 cell.

Isolation and identification of a new neo-clerodane diterpenoid from Teucrium chamaedrys L.

Teucrium chamaedrys L. is an aromatic and medicinal plant used as traditional medicine. Aerial parts of the plant material were dried and extracted with hexane-dichloromethane (extract 1), ethyl acetate-dichloromethane (extract 2) and methanol-dichloromethane (extract 3) in a ratio of 1:1 at rt successively. The solvents were evaporated to give crude extracts. Extract 1 was suspended in water at 60°C then partitioned successively with hexane and ethyl acetate to give hexane and ethyl acetate portions. After the column chromatography (silica gel) of ethyl acetate extract, one new and four known compounds were isolated. The new compound was named as 1(12S,18R)-15,16-epoxy-2ß,6ß-dihydroxy-neo-cleroda-13(16),14-dien-20,l2-olide-l8,l9-hemiacetal (teuchamaedryn D) (4). The known compounds were teucrin A (1), dihydroteugin (2), teucroxide (3), syspirensin A (5). The chromatographic methods were also applied for extract 3 to isolate verbascoside (6) and teucrioside (7). The structure of isolated compounds was elucidated by spectroscopic methods including LC-TOF/MS, 1D NMR and 2D NMR.

Isolation and identification of chemical constituents from Origanum majorana and investigation of antiproliferative and antioxidant activities.

BACKGROUND: Origanum majorana L., belonging to the Lamiaceae family, has great potential and has been used as a folk medicine against asthma, indigestion, headache and rheumatism; in addition, the essential oils of this plant have been used widely in the food industry. Plant materials have been harvested from the Medicinal and Aromatic Plant Field of Gaziosmanpasa University. Air-dried plant materials were boiled in water, filtered, and the solvent part subsequently extracted with hexane and ethyl acetate. The chromatographic method was applied to the ethyl acetate extract to isolate bioactive secondary metabolites, the structures of which were elucidated by spectroscopic techniques: basically one-dimensional and two-dimensional nuclear magnetic resonance and quadrupole time-of-flight liquid chromatography. Antiproliferative and antioxidant activities of isolated secondary metabolites were determined. RESULTS: 5,6,3'-Trihydroxy-7,8,4'-trimethoxyflavone, hesperetin, hydroquinone, arbutin and rosmarinic acid were isolated from the water-soluble ethyl acetate extract of aerial parts of O. majorana. Antioxidant activities of isolated compounds and water-soluble ethyl acetate extract were investigated using assays of DPPH(•), ABTS(•+), reducing power and total phenolic content. Antiproliferative activities of the isolated compounds and plant extracts were investigated against C6 and HeLa cell lines using BrdU cell proliferation enzyme-linked immunosorbent assay and xCELLigence assay, respectively. Both hesperetin and hydroquinone were determined to have stronger antiproliferative activities against C6 and HeLa cells than the other isolated compounds and 5-fluorouracil. CONCLUSION: The results showed that the extract and isolated compounds exhibited significant antioxidant activities. Hence this plant has the potential to be a natural antioxidant in the food industry and an anticancer drug.