The Thai medicinal plant Gynura pseudochina var. hispida: chemical composition and in vitro NF-kappaB inhibitory activity

Gynura pseudochina (L.) var. hispida Thv. (Asteraceae) has been used in traditional medicine in Thailand for the treatment of conditions associated with chronic and acute inflammation. In continuation of our search for bioactive natural products from Thai medicinal plants, G. pseudochina var. hispida showed potential in vitro NF-kappaB (Nuclear Factor kappa B) inhibitory activity and, therefore, was chosen for bio-assay-guided isolation of active compounds. Bioassay-guided fractionation of the methanol extract of the leaves of G. pseudochina var. hispida led to the isolation and identification, by spectroscopic and mass spectrometric methods, of four compounds previously not reported from this poorly studied species: Quercetin 3- rutinoside (1), 3,5-di-caffeoylquinic acid (2), 4,5-di-caffeoylquinic acid (3), and 5-monocaffeoylquinic acid (4). This paper discusses the current knowledge of these active components as NF-kappaB inhibitors, which lends some support to the use of this plant in traditional medicine. Potential risks associated with pyrrolizidine alkaloids will, however, have to be investigated further.     

A liquid chromatography‐atmospheric pressure photoionization tandem mass spectrometric (LC‐APPI‐MS/MS) method for the determination of triterpenoids in medicinal plant extracts

An analytical method using liquid chromatography‐atmospheric pressure photoionization tandem mass spectrometry with toluene as a dopant was developed for the determination of triterpenes in medicinal plant extracts. The 12 compounds determined have been shown to exhibit biological activity, such as gastroprotective, hepatoprotective, anti‐inflammatory, antiviral and anti‐tumor effects. The parameters of the atmospheric pressure photoionization interface were optimized to obtain the highest possible sensitivity for all of the compounds. The limits of detection and quantification ranged from 0.4 to 157.9 µg l^?1 and 1.3 to 526.4 µg l^?1, respectively. The method was validated and applied to extracts of five medicinal plants species (Mansoa alliacea (Lam.) A.H.Gentry, Bauhinia variegata var variegata, Bauhinia variegata var alboflava, Cecropia obtuse Trécul and Cecropia palmate Willd) from the Amazonian region. The concentrations of the six triterpenes quantified in the samples ranged from 0.424 mg kg^?1 for ursolic acid to 371.96 mg kg^?1 for β‐amyrin, which were quantified by using the standard addition method (n = 3). Copyright © 2016 John Wiley & Sons, Ltd.     

Studies on rhizosphere microbial diversity of some commercially important medicinal plants

A preliminary study was made on four medicinal plants viz., Ocimum sanctum L., Coleus forskholii Briq, Catharanthus roseus (L.) G. Don. and Aloe vera in order to identify and enumerate the rhizosphere, non-rhizosphere and diazotrophic microorganisms in soil. The diazotrophic bacterial population studied includes Azospirillum, Azotobacter and Pseudomonas. The rhizosphere bacterial populations were 23.33 x 10(6)g(-1) in O. sanctum followed by C. roseus (20.46 x 10(6)g(-1)), A. vera (18.44 x 10(6)g(-1)) and C. forskholii (16.64 x 10(6)g(-1)). The fungi populations were 19.44 x 10(4)g(-1) in C. roseus, 18.66 x 10(4)g(-1) in O. sanctum, 16.44 x 10(4)g(-1) in A. vera and 14.22 x 10(4)g(-1) in C. forskholii. The actinomycetes population was 12.22 x 10(5)g(-1) in O. sanctum, 10.44 x 10(5)g(-1) in C. roseus, 8.44 x 10(5)g(-1) in A. vera and 6.22 x 10(5)g(-1) in C. forskholii. The diazotrophic bacterial population of Azospirillum, Azotobacter and Pseudomonas is 8.2 x 10(4)g(-1), 12 x 10(4)g(-1), 6 x 10(4)g(-1) in the rhizosphere soil. In all the four medicinal plants the microbial population is more in the rhizosphere soil, when compared to non-rhizosphere soil. These results are helpful in developing a biofertilizer consortium for these commercially grown medicinal plants.     

Two Novel Dibutyltin Complexes with Trimers and Hexanuclear Based on the Bis(5-Cl/Me-salicylaldehyde) Carbohydrazide: Syntheses,Structures, Fluorescent Properties and Herbicidal Activity

Two novel bis(2-hydroxy-5-R-benzylidene) carbohydrazide dibutyltin complexes(R: Cl(T1), Me(T2)) with hexanuclear and triangular frame structures were obtained by microwave-assisted solvothermal reaction of dibutyltin oxide precursor with the ligands in methanol environments, However, their structures are characterized by elemental analysis, IR,(1 H, 13 C) NMR spectra, and the molecular structures of T1 and T2 were confirmed by X-ray diffraction. The crystal of T1 belongs to triclinic system, space group P1, and T2 is of monoclinic system, space group C2/c. Five-coordinated distorted triangular bipyramids and six-coordinated distorted octahedral configurations were formed by the coordination of oxygen and nitrogen atoms of ligands with two dibutyltins, respectively, and trimer hexanuclear dibutyltin complexes were constructed by the cross-coordination of enol imines. The two complexes exhibit fluorescence emission in DMF solvents and DMF-water mixtures. When the volume fraction of water content is between 0 and 10%(V/V), the aggregation fluorescence enhancement effect is good, and fluorescence quenching occurs when the water content is more than 10%(V/V). The T1 can inhibit the growth of target plants, such as Portulaca oleracea, Cassia tora L., Brassica campestris L.ssp.chinensis var.utilis Tsen et Lee and Amaranthus tricolor L. The T2 can selectively inhibit the growth of Portulaca oleracea L., Amaranthus spinosus L. and Amaranthus tricolor L. It can be used as a candidate herbicide for Portulaca oleracea L., Amaranthus spinosus L. and Amaranthus tricolor L.     

Diversity of Volatile Compounds in Ten Varieties of Zingiberaceae

Zingiberaceae plants are distributed in the tropical and subtropical regions of the world, being used in many famous medicinal materials. Meanwhile, some Zingiberaceae plants are important horticultural flowers because they are green all year round and have special aromas. To conduct an extensive investigation of the resources of Zingiberaceae plants, the volatile compounds of ten species of Zingiberaceae were extracted and analyzed by GC–MS, including Costus comosus var. bakeri (K.Schum.) Maas, Curcuma rubescens Roxb., Curcuma aeruginosa Roxb., Curcuma attenuata Wall., Hongfengshou, Hedychium coronarium Koeng, Zingiber zerumbet (L.) Smith, Hedychium brevicaule D. Fang, Alpinia oxyphylla Miq., and Alpinia pumila Hook.F. A total of 162 compounds were identified, and most of those identified were monoterpenes and sesquiterpenes. (E)-labda-8(17),12-diene-15,16-dial, n-hexadecanoic acid, 4-methoxy-6-phenethyl-2H-pyran-2-one, and L-β-pinene were found in high concentrations among the plants. These ten species of Zingiberaceae contained some of the same volatiles, but their contents were different. Pharmacological effects may be associated with the diversity of volatiles in these ten plants.     

Antioxidant potentials and ajmalicine accumulation in Catharanthus roseus after treatment with giberellic acid

Changes in antioxidant potentials and indole alkaloid, ajmalicine, production were studied in Catharanthus roseus (L.) G. Don. plants under treatment with gibberellic acid (GA(3)). The GA(3) treatments were given in two ways, foliar spray and soil drenching methods on 30, 45, 60 and 75 days after planting (DAP). The plants were uprooted randomly on 90 DAP and separated into root, stem and leaves and used for analyses. The antioxidant potential was studied in terms of non-enzymatc antioxidant molecules like ascorbic acid (AA), alpha-tocopherol (alpha-toc) and reduced glutathione (GSH) and activities of antioxidant enzyme, viz., superoxide dismutase (SOD), ascorbate peroxidase (APX) and catalase (CAT). The alkaloid ajmalicine was extracted and estimated from roots of both control and treated plants. It was found that, GA(3) has a profound effect upon the antioxidant potentials and it caused a significant enhancement in the production of ajmalicine when compared to untreated control as well as foliar-sprayed plants. There was no significant enhancement in GSH and ajmalicine content under GA(3) foliar spray in C. roseus. These preliminary results suggest that, the application of GA(3) may be a useful tool to increase the antioxidant potential and alkaloid production in medicinal plants like C. roseus.     

Selenium concentrations of selected medicinal and aromatic plants in Turkey

Recent scientific studies have proven the importance of trace elements on human health. The main food supplies are plants and animals, which are significant sources of these minerals. Studies on determining mineral compositions of herbs, spices and some other crops have increased all over the world. Published works revealed that spices, herbs and medicinal plants should be consumed to obtain beneficial trace elements. Selenium (Se), one of the most vital trace elements, has a significant role in human diet acting as a preventative agent against some serious illnesses. Despite numerous scientific works on mineral compositions of medicinal and aromatic plants, investigations of selenium content in these foods could not be successfully studied until recently due to the lack of suitable analytical methods for selenium analysis. Thus, publications on selenium concentrations of foods are recent. In this regard, selenium contents of some medicinal and aromatic plants commonly used as spices, herbal teas and traditional medicines in Turkey were studied in the present research. Selenium contents of the most used parts of these plants were analyzed by ICP-OES (Varian Vista-Pro, Australia). Of the analyzed 26 medicinal and aromatic plants, the highest Se concentration (1133 microg kg-1) was found in sweet basil (Ocimum basilicum L.) and the lowest in sumac (Rhus coriaria L.) fruits (11 microg kg(-1)).     

The Potential Use of Herbal Fingerprints by Means of HPLC and TLC for Characterization and Identification of Herbal Extracts and the Distinction of Latvian Native Medicinal Plants

The growing market of herbal medicines, the increase in international trade in Latvia, and the lack of adequate analytical methods have raised the question of the potential use of herbal fingerprinting methods. In this study, high-performance liquid chromatography (HPLC) and thin layer chromatography (TLC) methods were developed for obtaining chromatographic fingerprints of four taxonomically and evolutionary different medicinal plants (Hibiscus sabdariffa L., Calendula officinalis L., Matricaria recutita L., Achillea millefolium L.). Retention time shifting, principal component analysis (PCA), hierarchical cluster analysis (HCA), and orthogonal projections to latent structures (OPLS) analysis were used to improve and analyze the obtained fingerprints. HPLC data detection at 270 nm was determined superior to 360 nm for the distinction of medicinal plants and used data alignment method significantly increased similarity between samples. Analyzed medicinal plant extracts formed separate, compact clusters in PCA, and the results of HCA correlated with the evolutionary relationships of the analyzed medicinal plants. Herbal fingerprinting using chromatographic analysis coupled with multivariate analysis has a great potential for the identification of medicinal plants as well as for the distinction of Latvian native medicinal plants.     

Antibacterial activity and GC/MS analysis of the essential oils from flower, leaf and stem of Origanum vulgare ssp. viride growing wild in north-west Iran

Essential oils obtained from flowers, leaves and stems of Origanum vulgare L. ssp. viride (Boiss.) Hayek., growing wild in Ardabil Province (north-west Iran), were analyzed by GC and GC/MS. beta-Caryophyllene was the major constituent in all three oils (48.1%, 50.1% and 60.2%, respectively). Of the 19 components detected in the flower oil, comprising 96.3% of the total, the major components were 1,8-cineole (11.6%), alpha-pinene (6.9%), and gamma-cadinene (4.8%). 1-Octen-3-ol (23.8%), and 1,8-cineole (8.5%) predominated in the leafoil. In the stem oil, other main constituents were bicyclogermacrene (9.8%), 1,8-cineole (6.4%), borneol (5.1%), and pinocarvone (4.4%). The essential oils were evaluated for their antibacterial activity against 10 selected microorganisms. The data obtained contribute to the future use of certain essential oils as natural preservatives for food products, due to their safety and positive effect on shelf life.     

Fatty acid composition of Juniperus species (Juniperus section) native to Turkey

Fatty acid compositions of seeds of five taxa of the Juniperus section of the genus Juniperus L. (Cupressaceae), i. e. J. drupacea Lab., J. communis L. var. communis, J. communis var. saxatilis Pall., J. oxycedrus L. subsp. oxycedrus, and J. oxycedrus subsp. macrocarpa (Sibth. & Sm.) Ball, were investigated. Methyl ester derivatized fatty acids of the lipophylic extracts of the five species were comparatively analyzed by capillary gas chromatography-mass spectrometry (GC-MS). Juniperus taxa showed uniform fatty acid patterns, among which linoleic (25.8 - 32.5%), pinolenic (11.9 - 24.1%) and oleic acids (12.4 - 17.2%) were determined to be the main fractions in the seed oils. Juniperonic acid was found to be remarkably high in J. communis var. saxatilis (11.4%), J. oxycedrus subsp. oxycedrus (10.4%), and J. communis var. communis (10.1%). To the best of our knowledge, the present work discloses the first report on the fatty acid compositions of seeds of this Juniperus section grown in Turkey.     

Water deficit stress effects on reactive oxygen metabolism in Catharanthus roseus; impacts on ajmalicine accumulation

In the present work, we have analysed the changes in the reactive oxygen metabolism of Catharanthus roseus (L.) G. Don. plants in terms of H(2)O(2) content, lipid peroxidation and the free radical quenching systems (non-enzymatic and enzymatic antioxidants) under drought stress. In addition to this, the root alkaloid ajmalicine was extracted and quantified from both control and drought stressed plants. The H(2)O(2) content was analysed from both stressed and unstressed control plants. Lipid peroxidation was estimated as thiobarbituric acid reactive substances. The non-enzymatic antioxidants viz., ascorbic acid, alpha-tocopherol and reduced glutathione contents, antioxidant enzymes like superoxide dismutase, ascorbate peroxidase, and catalase were extracted and estimated from the samples. The alkaloid ajmalicine was extracted and quantified from shade dried root samples and found significantly increased over control. From the results of this investigation, it can be concluded that the water deficit areas may be well used for the cultivation of medicinal plants like C. roseus and the economically important alkaloid production can be enhanced in the plant level.     

Two new β-carboline-type alkaloids from Stellaria dichotoma var.lanceolata

Two new β-carboline-type alkaloids,dichotomine K(1) and dichotomine L(2),were isolated from the roots of Chinese medicinal plant Stellaria dichotoma L.var.lanceolata Bge.Structures of 1 and 2 were determined on the basis of chemical and spectroscopic means.     

Antiviral properties from plants of the Mediterranean flora

Natural products are a successful source in drug discovery, playing a significant role in maintaining human health. We investigated the in vitro cytotoxicity and antiviral activity of extracts from 18 traditionally used Mediterranean plants. Noteworthy antiviral activity was found in the extract obtained from the branches of Daphne gnidium L. against human immunodeficiency virus type-1 (EC₅₀ = 0.08 μg/mL) and coxsackievirus B5 (EC₅₀ = 0.10 μg/mL). Other relevant activities were found against BVDV, YFV, Sb-1, RSV and HSV-1. Interestingly, extracts from Artemisia arborescens L. and Rubus ulmifolius Schott, as well as those from D. gnidium L., showed activities against two different viruses. This extensive antiviral screening allowed us to identify attractive activities, offering opportunities to develop lead compounds with a great pharmaceutical potential.     

The essential oils of the aerial parts of two Hypericum taxa (Hypericum triquetrifolium and Hypericum aviculariifolium subsp. depilatum var. depilatum (Clusiaceae)) from Turkey

In this study, essential oil compositions of two Hypericum L. taxa (Hypericum triquetrifolium Turra. and Hypericum aviculariifolium Jaub. et Spach subsp. depilatum var. depilatum (Freyn et Bornm.) Robson) naturally grown in Turkey were determined using gas chromatography and gas chromatography-mass spectrometry systems. The essential oils were obtained by hydrodistillation from the aerial parts of plants. A total of 45 compounds were identified in the essential oils of H. triquetrifolium; 1-hexanal (18.8%), 3-methylnonane (12.5%) and α-pinene (12.3%). In this study, 41 components were identified in H. aviculariifolium subsp. depilatum var. depilatum oil; α-pinene (52.1%), germacrene D (8.5%) and β-pinene (3.6%) were the predominant constituents. The essential oil analysis showed that monoterpene concentrations were higher than that of the sesquiterpenes in both oils. The results were discussed in the meaning of the usefulness of these plants and their chemicals as natural products and potential usage in chemotaxonomy.     

Chemical composition and insecticidal activity of essential oils of two aromatic plants from Ivory Coast against Bemisia tabaci G. (Hemiptera: Aleyrodidae)

Essential oils of aromatic plants with insecticidal properties are nowadays considered as alternative insecticides to protect cultures from attack by insect pest. The aims of the present work were to evaluate the toxicity of the essential oils vapors of two aromatic plants (Lippia multiflora Mold. and Aframomum latifolium K. Schum) against Bemisia tabaci and to characterize their chemical composition. The highest fumigant toxicity against B. tabaci adults was observed with the L. multiflora oil: by exposure to 0.4 microL/L air, the lethal time inducing 90% mortality (LT90) was below 2 hours for this essential oil whereas it reached 15 h in the case of the A. latifolium oil. Both oils were analyzed by GC-FID and GC-MS on two capillary columns. The oil of L. multiflora contained a majority of oxygenated terpenoids mainly represented by the two acyclic components linalool (46.6%) and (E)-nerolidol (16.5%); the oil of A. latifolium was dominated by hydrocarbonated terpenoids among them beta-pinene (51.6%) and beta-caryophyllene (12.3%) were the two major components.     

Alterations in osmoregulation, antioxidant enzymes and indole alkaloid levels in Catharanthus roseus exposed to water deficit

Catharanthus roseus (L.) G. Don plants were grown in different water regimes in order to study the drought induced osmotic stress and proline (PRO) metabolism, antioxidative enzyme activities and indole alkaloid accumulation. The plants under pot culture were subjected to 10, 15 and 20 days interval drought (DID) stress from 30 days after sowing (DAS) and regular irrigation was kept as control. The plants were uprooted on 41 DAS (10 DID), 46 DAS (15 DID) and 51 DAS (20 DID). The drought stressed plants showed increased aminoacid (AA), glycine betaine (GB) and PRO contents and decreased proline oxidase (PROX) and increased γ-glutamyl kinase (γ-GK) activities when compared to control. The antioxidative enzymes like peroxidase (POX) and polyphenol oxidase (PPO) increased to a significant level in drought stressed plants when compared to control. The drought stressed C. roseus plants showed an increase in total indole alkaloid content in shoots and roots when compared to well-watered control plants. Our results suggest that the cultivation of medicinal plants like C. roseus in water deficit areas would increase its PRO metabolism, osmoregulation, defense system and the level of active principles.     

Chemical constituents from Farfugium japonicum var. formosanum

Two new eremophilenolides, 6beta,8beta,10beta-trihydroxyeremophil-7(11)-en-12,8-olide (1) and 3beta-acetoxy-8alpha-hydroxy-6beta-methoxyeremophila-7(11),9-dien-12,8-olide (2) along with twenty-nine other compounds were obtained from the methanolic extracts of the aerial parts and rhizomes of Farfugium japonicum (L.) Kitam. var. formosanum (Hayata) Kitam. (Compositae = Asteraceae). The structures of the isolated compounds were characterized and identified by spectral techniques. Compounds 5, 6, 10, 12-24, 29, and 30, were reported for the first time from this genus. Cytotoxicity and anti-inflammatory activity of the isolated compounds were evaluated. Compounds 3 and 16 possessed moderate cytotoxicity against human breast cancer cell line (MCF 7). Compounds 3, 16, 25 and 26 exhibited moderate cytotoxicity against hepatoma cells (Hep G2 and Hep 3B). With respect to the anti-inflammatory activity, compounds 15 and 16 (each 10 microg/mL) inhibited superoxide anion generation by human neutrophils in response to fMLP/CB by 92.0% and 87.3%, respectively.     

Essential oil constituents and biological activities of Peristrophe bicalyculata and Borreria verticillata

Peristrophe bicalyculata (Retz) Nees (Acanthaceae) or 'The Goddess of Mercy' and Borreria verticillata (L.) G.F.W. Mey., (Rubiaceae), or 'Irawo-Ile' (Yoruba, South-west, Nigeria), are annual herbs, which are poorly exploited. The volatile oils obtained by hydrodistillation in an all glass Clevenger-type apparatus from the plant samples have been investigated by gas chromatography-mass spectrometry (GC-MS). With respect to the oil of P. bicalyculata, beta-caryophyllene (33.9%), alpha-zingiberene (10.4%), germacrene D and globulol (5.0%) were the compounds occurring in abundance. The oil of B. verticillata had an abundance of phytol (56.3%) and 1, 8-cineole (20.4%), with sizeable proportions of alpha-pinene (7.1%) and p-cymene (4.0%). In addition, the volatile oils displayed promising in-vitro antimicrobial activity against the tested micro-organisms, (MIC 12.5-22.3 microg/mL), while only the oil of P. bicalyculata displayed in-vitro cytotoxicity to MCF-7 (human breast tumor) and MDA-MB-468 (human breast tumor) cells. The present investigation may be the first of its kind for the evaluation of the volatile oil constituents of the studied plants.     

Structure-based virtual screening and molecular dynamics of phytochemicals derived from Saudi medicinal plants to identify potential COVID-19 therapeutics

Coronavirus disease 2019 (COVID-19) has affected almost every country in the world by causing a global pandemic with a high mortality rate. Lack of an effective vaccine and/or antiviral drugs against SARS-CoV-2, the causative agent, has severely hampered the response to this novel coronavirus. Natural products have long been used in traditional medicines to treat various diseases, and purified phytochemicals from medicinal plants provide a valuable scaffold for the discovery of new drug leads. In the present study, we performed a computational screening of an in-house database composed of ~1000 phytochemicals derived from traditional Saudi medicinal plants with recognised antiviral activity. Structure-based virtual screening was carried out against three druggable SARS-CoV-2 targets, viral RNA-dependent RNA polymerase (RdRp), 3-chymotrypsin-like cysteine protease (3CL^pro) and papain like protease (PL^pro) to identify putative inhibitors that could facilitate the development of potential anti-COVID-19 drug candidates. Computational analyses identified three compounds inhibiting each target, with binding affinity scores ranging from −9.9 to −6.5 kcal/mol. Among these, luteolin 7-rutinoside, chrysophanol 8-(6-galloylglucoside) and kaempferol 7-(6″-galloylglucoside) bound efficiently to RdRp, while chrysophanol 8-(6-galloylglucoside), 3,4,5-tri-O-galloylquinic acid and mulberrofuran G interacted strongly with 3CL^pro, and withanolide A, isocodonocarpine and calonysterone bound tightly to PL^pro. These potential drug candidates will be subjected to further in vitro and in vivo studies and may assist the development of effective anti-COVID-19 drugs.     

Secoiridoids Glycosides from Some Selected Jasminum SPP

Secoiridoid glycosides of three oleaceaous plants are described. Fractionation of the ethanolic extracts of Jasminum nitidum Skan, J. giraldii Diels and J. sambac (L.) Ait. var. trifoliatum Hort. (Oleaceace) resulted in the isolation of syringalactones A ( 1 ) and B ( 2 ), oleoside 7,11‐dimethyl ester ( 3 ), jasminoside (7), jaslanceosides B ( 8 ), sambacoside A ( 9 ) and molihuaside D ( 10 ). The structures of these secoiridoid glycosides were elucidated on the basis of spectral methods. Chemotaxonomy for plants of Jasminum is also discussed.