The chemical composition and antibacterial activity of a methanolic extract of Satureja khuzistanica

Abstract In the present study, the metabolite profiling of methanolic extract from aerial parts of Satureja khuzistanica Jamzad, as an endemic medicinal plant from Iran, was evaluated using HPLC-PDA-ESI. Then, the main compound from the extract was isolated and purified by using extensive chromatographic techniques. In addition, the structure of the isolated compounds was elucidated using 1D, 2D NMR, and MS spectrometry, upon which 22 compounds were identified. The antibacterial activity of diosmetin 7-rutinoside (6) and linarin (13) in combination with carvacrol as a major compound of the essential oil was tested against Pseudomonas aeruginosa and Staphylococcus aureus through disc diffusion and minimum inhibitory concentration methods. The results indicated that the linarin, when mixed with carvacrol as the main compounds in the essential oil of the plant, has a satisfactory activity against both Pseudomonas aeruginosa and Staphylococcus aureus with MIC values of 0.16 and 0.18 µg/mL, respectively. Further, the fractional inhibitory concentration (FIC) index indicated that this compound had synergism with carvacrol.

Phytochemical Synthesis of Silver Nanoparticles by Two Techniques Using Saturaja rechengri Jamzad Extract: Identifying and Comparing in Vitro Anti-Proliferative Activities.

Purpose: A lot of plants are available which can produce nanoparticles used in medicine, life sciences, and the pharmaceutical industry. The present study aims to introduce safe biological and eco-friendly methods for synthesizing silver nanoparticles (AgNPs) by using Saturaja rechengri Jamzad extract, which can replace traditional chemical methods. In addition, the chemical nature and antimicrobial activities were identified and accordingly the anticancer effects of AgNPs was successfully reported on colon cancer cells (HT-29). Methods: Light and ultrasound, as two green chemistry techniques were first used for AgNPs synthesis. Then, morphological and crystalline structure of AgNPs was evaluated by scanning electron microscopy (SEM) and X-ray diffraction (XRD) analysis, respectively. In addition, functional groups were determined by using the Fourier transform infrared spectroscopy (FTIR) spectrum. Further, a maximum adsorption of AgNPs was observed in UV-visible spectrum. In the next stage, antibacterial activity of green synthesized AgNPs was evaluated against two pathogenic bacteria including Escherichia coli and Staphylococcus aureus. Finally, the cytotoxicity of AgNPs on HT-29 at different concentrations and times of AgNPs was determined by MTT assay. Results: The findings indicated that the synthesis of AgNPs by ultrasonic technique leads to smaller particle size and more distribution. Based on the results of MTT test for calculating the IC50%, the anti-proliferative effects of the light and ultrasound AgNPs were observed on HT-29 cell lines depending on the dose and time. Finally, the AgNPs had the most cytotoxicity HT-29 cell lines at 100 µg/ml concentration although the lowest toxicity effect was reported on HEK-293 cell lines at the same conditions. Conclusion: The change in the concentration, physical and chemical properties of AgNPs including the form and size of particles, and their type of covering and fields can influence the induction of cytotoxicity and morphological change in the treated cells. The present research opens a new horizon on the development of new biological and cytotoxicity agents.

Biosynthesis and application of Ag/bone nanocomposite for the hydration of cyanamides in Myrica gale L. extract as a green solvent.

This study focuses on the green synthesis of the Ag/bone nanocomposite by using Myrica gale L. aqueous extract as a reducing and stabilizing agent and investigation of its catalytic activity in the hydration of cyanamides under environmentally benign reaction conditions in aqueous extract as a green solvent without use of toxic and hazardous chemicals. The green synthesized Ag/bone nanocomposite was characterized by various analytical techniques such as X-ray diffraction analysis (XRD), field emission scanning electron microscope (FESEM), transmission electron microscopy (TEM) images, energy-dispersive X-ray spectroscopy (EDS), elemental mapping, and FT-IR spectroscopy. The advantages of this system include the use of green catalyst, benign reaction conditions without use of expensive and hazardous materials, easy work up, reusability of the catalyst and excellent yield of the products. The Ag/bone nanocomposite can be recovered and recycled several times without significant loss of activity.

Green synthesis of the Cu/ZnO nanoparticles mediated by Euphorbia prolifera leaf extract and investigation of their catalytic activity.

A green synthesis process was developed for the preparation of the Cu/ZnO nanoparticles (NPs) using Euphorbia prolifera leaf extract as a mild, renewable and non-toxic reducing agent and efficient stabilizer without using dangerous, hazardous and toxic materials. The approach of biosynthesis appears to be cost efficient eco-friendly and easy alternative to conventional methods of the Cu/ZnO NPs synthesis. The Cu/ZnO NPs were characterized by FESEM, EDS, elemental mapping, TEM and XRD. TEM micrograph has shown the formation of Cu NPs with the size in the range of 5-17 nm. In addition, the synthesized Cu/ZnO NPs presented excellent catalytic activity for the degradation of Methylene blue (MB) and Congo red (CR) in the presence of NaBH4 in water at room temperature.

Investigation of in vitro cytotoxic, mutagenic and anti-mutagenic effects of shirazolide extracted from Jurinea leptoloba.

Shirazolide is an elemanolide isolated from Jurinea leptoloba DC. The aim of this study was to determine the cytotoxic, mutagenic and anti-mutagenic properties of shirazolide from J. leptoloba DC in vitro. Cytotoxicity was measured using a modified MTT (3-(4,5-di methyl thiazol-2-yl)-2,5-di phenyltetrazolium bromide) assay on normal human lymphocytes and tumor HeLa cells, showing that the cytotoxicity of shirazolide is much higher for HeLa cells than for normal lymphocytes. Mutagenic and anti-mutagenic activities of shirazolide were evaluated using the Salmonella typhimurium tester strains TA98 and TA100 showing anti-mutagenic properties against the former strain under metabolic activation.

Alpha-amylase inhibitory activity and sterol composition of the marine algae, Sargassum glaucescens.

BACKGROUND: Sargassum species (phaeophyceae) are economically important brown algae in southern parts of Iran. Sargassum is mainly harvested as a row material in alginate production industries and is a source of plant foods or plant bio-stimulants even a component of animal foods. OBJECTIVE: In this study, Sargassum glaucescens, collected from the seashore of Chabahar, was employed for phytochemical and biological evaluations. MATERIALS AND METHODS: For that purpose, the dried algae was extracted by methanol and subjected to different chromatographic separation methods. RESULTS: Six sterols, fucosterol (1), 24(S)-hydroxy-24-vinylcholesterol (2), 24(R)-hydroxy-24-vinylcholesterol (3), stigmasterol (4), ß-sitosterol (5) and cholesterol (6) were identified by spectroscopic methods including (1)H-NMR, (13)C-NMR and mass spectroscopy. In vitro alpha-amylase inhibitory test was performed on the methanolic extract and the results revealed a potent inhibition (IC50 = 8.9 ± 2.4 mg/mL) of the enzyme compared to acarbose as a positive control. CONCLUSION: Various biological activities and distribution of sterols in Sargassum genus have been critically reviewed here. The results concluded that these algae are a good candidate for further anti-diabetic investigations in animals and human.

Comparison of the volatile composition of Stachys pubescence oils obtained by hydro distillation and steam distillation.

The oils obtained by hydrodistillation and steam distillation of the aerial part of Stachys pubescence Ten. was analyzed by GC and GC/MS. Water distilled essential oil of the aerial part of S. pubescence, was rich in fatty acids like hexadecanoic acid and linoleic acid and also benzaldehyde and spathulenol whereas the steam distilled oil of the plant contained hexadecanoic acid, spathulenol and eugenol. Both of oils were rich in fatty acids (36.6 and 27.9%, respectively). Moreover, the content of oxygenated mono and sesquiterpenss were defined higher in steam distilled oil than hydrodistiledd oil (24.5, 17.2 and 6.1, 15.5%, respectively). In conclusion it seems that oxygenated terpenoids were trended to steam distillation method more than hydrodistillation, respectively.

Labdane-Type Diterpene and Two Flavones from Salvia Sharifii Rech. f. and Esfan. and their Biological Activities.

Two flavones, ladanein and 6-hydroxy-5,7,4'-trimethoxyflavone and one labdane-type diterpene, ent-13-epi-manoyloxide, were isolated from an ethyl acetate-methanol extract of the aerial parts of Salvia sharifii. The compounds were purified using several chromatographic methods. Structural elucidation of the compounds was performed using their (1)H and (13)C-NMR data, EI mass and UV spectral data. The compounds have been subjected to antimicrobial, antioxidant and cytotoxic activity. The diterpene showed higher cytotoxic activity than the flavones while the later compounds were better antioxidants compared with the isolated diterpene.

Comparison of antimalarial activity of Artemisia turanica extract with current drugs in vivo.

BACKGROUND & OBJECTIVES: The purpose of this study was to compare antimalarial activity of Artemisia turanica Krasch as Iranian flora with current antimalarial drugs against Plasmodium berghei in vivo in mice. METHODS: Air-dried aerial parts of Iranian flora A. turanica were collected from Khorasan, northeastern Iran, extracted with Et2O/MeOH/Petrol and defatted. Toxicity of herbal extracts was assessed on male NMRI mice, and their antimalarial efficacy was compared with antimalarial drugs [artemether, chloroquine and sulfadoxinepyrimethamine (Fansidar)] on infected P. berghei animals. All the groups were investigated for parasitaemia, body weight, hepatomegaly, splenomegaly and anemia. The significance of differences was determined by Analysis of Variances (ANOVA) and Student's t-test using Graph Pad Prism software. RESULTS: The inhibitory effects of A. turanica extract on early decline of P. berghei parasitaemia highlights its antimalarial activity, however, this effect no longer can be observed in the late infection. This may be due to the metabolic process of A. turanica crude extract by mice and reduction of its concentration in the body. Crude extract of A. turanica represented its antisymptomatic effects by stabilization of body, liver and spleen weights. CONCLUSION: This study confirmed antimalarial effects of A. turanica extracts against murine malaria in vivo during early infection, however, there are more benefits on pathophysiological symptoms by this medication.

A cytotoxic hydroperoxy sterol from the brown alga, Nizamuddinia zanardinii.

BACKGROUND: The marine environment is a unique source of bioactive natural products, of which Nizamuddinia zanardinii is an important brown algae distributed in Oman Sea. Literature revealed that there is no report on phytochemistry and pharmacology of this valuable algae. METHODS: Bioguided fractionation of the methanolic extract of Nizamuddinia zanardinii, collected from Oman Sea, led to the isolation of a hydroperoxy sterol. Its structure was determined by analysis of the spectroscopic data as 24-hydroperoxy-24-vinyl cholesterol (HVC). In vitro cytotoxic activity of this compound was evaluated against HT29, MCF7, A549, HepG2 and MDBK cell lines. RESULTS: Although 24(R)-hydroproxy-24-vinylcholesterol has been previously reported from Sargassum and Padina species, it is the first report on the presence of this compound from N. zanardinii. This compound exhibited cytotoxicity in all cell lines (IC50, 3.62, 9.09, 17.96, 32.31 and 37.31 µg/mL respectively). HVC was also evaluated for apoptotic activity and demonstrated positive results in terminal deoxynucleotidyl transferase dUTP Nick End labeling (TUNEL) assay suggesting it a candidate for further apoptotic studies. CONCLUSIONS: Nizamuddinia zanardinii, a remarkable brown algae of Oman Sea, is a good source of hydroproxy sterols with promising cytotoxic on various cell lines particularly human colon adenocarcinoma.

Green biosynthesis of silver nanoparticles using Callicarpa maingayi stem bark extraction.

Different biological methods are gaining recognition for the production of silver nanoparticles (Ag-NPs) due to their multiple applications. The use of plants in the green synthesis of nanoparticles emerges as a cost effective and eco-friendly approach. In this study the green biosynthesis of silver nanoparticles using Callicarpa maingayi stem bark extract has been reported. Characterizations of nanoparticles were done using different methods, which include; ultraviolet-visible spectroscopy (UV-Vis), powder X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray fluorescence (EDXF) spectrometry, zeta potential measurements and Fourier transform infrared (FT-IR) spectroscopy. UV-visible spectrum of the aqueous medium containing silver nanoparticles showed absorption peak at around 456 nm. The TEM study showed that mean diameter and standard deviation for the formation of silver nanoparticles were 12.40 ± 3.27 nm. The XRD study showed that the particles are crystalline in nature, with a face centered cubic (fcc) structure. The most needed outcome of this work will be the development of value added products from Callicarpa maingayi for biomedical and nanotechnology based industries.

Composition of the essential oils and antibacterial activities of Hymenocrater yazdianus, Stachys obtusicrena and Nepeta asterotricha three Labiatae herbs growing wild in Iran.

Water-distilled essential oils from leaves of Hymenocrater yazdianus Rech.f., flowers of Stachys obtusicrena Boiss., and stems and flowers of Nepeta asterotricha Rech.f., which are endemic to Iran, were analyzed by GC and GC/MS. Fifty-five components of the leaf oil of H. yazdianus were characterized, representing 95.1% of the total components detected. The major constituents were identified as 1,8-cineole (17.6%), beta-caryophyllene (13.9%), alpha-pinene (10.6%) and caryophyllene oxide (10.4%). Germacrene-D (37.5%) and alpha-bisabolol (23.5%) were the main components among the twenty constituents characterized in the flower oil of S. obtusicrena, representing 90.8% of the total components detected. Thirty-five compounds representing 93.0% of the stem oil of N. asterotrica were identified among which terpinen-4-ol (22.8%) and gamma-terpinene (14.1%) were the major ones. The flower oil of the species was characterized by higher amounts of terpinen-4-ol (24.8%), 4a alpha, 7a beta-nepetalactone (18.2%) and 1,8-cineole (11.6%) among the thirty-three components comprising 98.5% of the total oil detected. The antibacterial activity of the stem, leaf and flower oils of Hymenocrater yazdianus, Stachys obtusicrena and Nepeta asterotricha against seven Gram-positive and Gram-negative bacteria were determined using the MIC method. The growth inhibitory zone (mm) was also measured.

Volatile oil constituents of different parts of Artemisia chamaemelifolia and the composition and antibacterial activity of the aerial parts of A. turcomanica from Iran.

The essential oils obtained by hydrodistillation from the aerial parts, stem, leaf and flower of Artemisia chamaemelifolia Vill. and the aerial parts of A. turcomanica Gand. were analyzed by GC and GC/MS. Thirty-one compounds representing 96.6%, 94.6%, 93.2% and 91.0% of the oil were identified in the aerial parts, stem, leaf and flower oils of A. chamaemelifolia. Menthyl acetate (26.5%, 22.0%, 20.5% and 20.5%) and (Z)-nerolidol (20.8%, 26.3%, 14.7% and 18.1%) were the main constituents in the aerial parts, stem, leaf and flower oils, respectively. The other main component in the aerial parts, leaf and flower oils was 1, 8-cineole (13.9%, 11.7% and 12.8%, respectively). Yomogi alcohol (10.4%) and artemisyl acetate (10.4%) were the main components of the leaf and flower oil of the plant, respectively. No significant difference was observed between compositions of the aerial parts, stem, leaf and flower oils. Twenty-four compounds representing 90.5% of the oil of the aerial parts of A. turcomanica were identified, of which 1,8-cineole (15.5%), spathulenol (15.2%), camphor (14.8%), santolina alcohol (14.6%) and trans-beta-terpineol (11.6%) were the major ones. The stem, leaf and flower oils of A. turcomanica demonstrated antibacterial activity using the MIC method.

Biotransformation of germacranolide from Onopordon leptolepies by Aspergillus niger.

Terpenes are present in the essential oils obtained from herbs and spices. They are produced by these plant species as a chemical defense mechanism against phytopathogenic microorganisms. Therefore, terpenes have attracted great attention in the food industry, e.g., they have been used in foods such as cheese as natural preservatives to prevent fungal growth. Herein, we describe the microbial transformation of onopordopicrin (1) by Aspergillus niger. Four product 11α H-dihydroonopordopicrin (2), 11ß H-dihydroonopordopicrin (3), 3ß-hydroxy-11ß H-dihydroonopordopicrin (4), and 14-hydroxy-11ß H-dihydroonopordopicrin (5) were obtained. Their structures were identified on the basis of chemical and spectroscopic data. All the four compounds were novel.

Synthesis of silver nanoparticles in montmorillonite and their antibacterial behavior.

Silver nanoparticles (Ag NPs) were synthesized by the chemical reducing method in the external and interlamellar space of montmorillonite (MMT) as a solid support at room temperature. AgNO(3) and NaBH(4) were used as a silver precursor and reducing agent, respectively. The most favorable experimental conditions for synthesizing Ag NPs in the MMT are described in terms of the initial concentration of AgNO(3). The interlamellar space limits changed little (d-spacing = 1.24-1.47 nm); therefore, Ag NPs formed on the MMT suspension with d-average = 4.19-8.53 nm diameter. The Ag/MMT nanocomposites (NCs), formed from AgNO(3)/MMT suspension, were characterizations with different instruments, for example UV-visible, PXRD, TEM, SEM, EDXRF, FT-IR, and ICP-OES analyzer. The antibacterial activity of different sizes of Ag NPs in MMT were investigated against Gram-positive, ie, Staphylococcus aureus and methicillin-resistant S. aureus (MRSA) and Gram-negative bacteria, ie, Escherichia coli, Escherichia coli O157:H7, and Klebsiella pneumoniae, by the disk diffusion method using Mueller-Hinton agar (MHA). The smaller Ag NPs were found to have significantly higher antibacterial activity. These results showed that Ag NPs can be used as effective growth inhibitors in different biological systems, making them applicable to medical applications.

Green synthesis of silver/montmorillonite/chitosan bionanocomposites using the UV irradiation method and evaluation of antibacterial activity.

In this study, silver nanoparticles (Ag-NPs) were synthesized using a green physical synthetic route into the lamellar space of montmorillonite (MMT)/chitosan (Cts) utilizing the ultraviolet (UV) irradiation reduction method in the absence of any reducing agent or heat treatment. Cts, MMT, and AgNO(3) were used as the natural polymeric stabilizer, solid support, and silver precursor, respectively. The properties of Ag/MMT/Cts bionanocomposites (BNCs) were studied as the function of UV irradiation times. UV irradiation disintegrated the Ag-NPs into smaller sizes until a relatively stable size and size distribution were achieved. Meanwhile, the crystalline structure and d-spacing of the MMT interlayer, average size and size distribution, surface morphology, elemental signal peaks, functional groups, and surface plasmon resonance of Ag/MMT/Cts BNCs were determined by powder X-ray diffraction, transmission electron microscopy, scanning electron microscopy, energy dispersive X-ray fluorescence, Fourier transform infrared, and UV-visible spectroscopy. The antibacterial activity of Ag-NPs in MMT/Cts was investigated against Gram-positive bacteria, ie, Staphylococcus aureus and methicillin-resistant S. aureus and Gram-negative bacteria (ie, Escherichia coli) by the disk diffusion method on Muller-Hinton Agar at different sizes of Ag-NPs. All of the synthesized Ag/MMT/Cts BNCs were found to have high antibacterial activity. These results show that Ag/MMT/Cts BNCs can be useful in different biologic research and biomedical applications, such as surgical devices and drug delivery vehicles.

Structure elucidation of new oleanane-type glycosides from three species of Acanthophyllum.

From the roots of three species of Acanthophyllum (Caryophyllaceae), two new gypsogenic acid glycosides, 1 and 2, were isolated, 1 from A. sordidum and A. lilacinum, 2 from A. elatius and A. lilacinum, together with three known saponins, glandulosides B and C, and SAPO50. The structures of 1 and 2 were established mainly by 2D NMR techniques as 23-O-beta-D-galactopyranosylgypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-galactopyranoside (1) and gypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-galactopyranoside (2). The cytotoxicity of several of these saponins was evaluated against two human colon cancer cell lines (HT-29 and HCT 116).

Composition and antimicrobial activity of the essential oil of Artemisia kulbadica from Iran.

The hydrodistilled volatile oil from the aerial parts of Artemisia kulbadica Boiss. & Buhse was investigated by a combination of GC and GC/MS. Twenty-seven compounds were identified, representing 92.9% of the total oil. Sabinene (25.1%), trans-thujone (18.7%) and gamma-cadinene (16.0%) were the main components. The antimicrobial activity was determined against six bacterial strains and one fungal. The oil was active against all the tested strains.

Chemical composition and antibacterial activity of essential oils from leaves, stems and flowers of Salvia reuterana Boiss. grown in Iran.

The essential oils obtained by hydrodistillation of the leaves, stems and flowers of Salvia reuterana (Lamiaceae) were analysed by GC and GC/MS. Germacrene D and beta-caryophyllene were the major constituents in all the three oils: (28.5, 27.7 and 32.5%) and (15.5, 11.4 and 16.6%), respectively. Bicyclogermacrene (10.2 and 13.2%) was also prodominated in the stem and flower oils. The composition of the oils was mostly quantitativel rather than qualitatively different. All the oils consisted mainly of sesquiterpenes and a small percentage of non-terpenoid compounds. In all the three oils, monoterpenes were in a concentration less than 0.5%. Antibacterial activity was determined by the measurement of growth inhibitory zones.

Biosorption of copper, cobalt and nickel by marine brown alga Sargassum sp. in fixed-bed column.

The biosorption of copper, cobalt and nickel by marine brown alga Sargassum sp. were investigated in a fixed-bed column (temperature = 30 degrees C; different pH). Langmuir and Freundlich sorption models were used to represent the equilibrium data. The maximum Cu2+ uptake was obtained at pH 4 and the optimum Co2+ and Ni2+ uptake were at pH 7. Different dosage of biosorbent did not have an effect on the results, but the 3.5 and 5 g of biosorbent were shown higher uptake. The metal removal rates were rapid, with about 80% of the total adsorption tacking place within 40 min.