bluuebunny/crossref_metadata_2025 huggingface dataset:
Comparative Chemical, Cytotoxicity and Antileishmanial Properties of Essential Oils from Chenopodium ambrosioides
Authors: Monzote Lianet , Nance Marcelina R. , García Marley , Scull Ramón , Setzer William N.
Published: March 2019

In countries where leishmaniasis is endemic, there are not very many treatment alternatives and most options have problems associated with their use. Plants and their natural products constitute good sources of interesting lead compounds that could be potentially active against Leishmania. Chenopodium ambrosioides is a plant that is widely used in popular medicine and its antiparasitic effects have been documented, including the antileishmanial potentialities of Chenopodium oil. The objective of this study was to determine the chemical composition, in-vitro cytotoxicity and antileishmanial activity of essential oils extracted from C. ambrosioides, which received different treatments prior to extraction. The chemical characterization by GC-MS of the three essential oil samples showed similar composition and the major components were α-terpinene (17.0-20.7%), p-cymene (20.2-21.1%) and ascaridole (30.5-47.1%). The essential oils exhibited similar antileishmanial activities against intracellular amastigote form, with IC50 values between 4.7 and 12.4 μg/mL. However, a lower cytotoxicity was displayed by the essential oil extracted from fresh green vegetable material, which was statistically different ( P < 0.05) from the other samples. This study demonstrated that the prior treatment of plant material did not interfere with the antiparasitic activity of essential oils from C. ambrosioides but did change their cytotoxicity, which should be taken into account in further studies.
Cytotoxic Bibenzyls, and Germacrane- and Pinguisane-type Sesquiterpenoids from Indonesian, Tahitian and Japanese Liverworts
Authors: Komala Ismiarni , Ito Takuya , Nagashima Fumihiro , Yagi Yasuyuki , Asakawa Yoshinori
Published: March 2019

Cytotoxic bibenzyls, and germacrane- and pinguisane-type sesquiterpenoids have been isolated from unidentified Indonesian and Tahitian Frullania sp. and Japanese Porella perrottetiana by using a combination of chromatographic methods. The structure activity relationship (SAR) study showed that the presence of a phthalide group in bibenzyls, an α-methylene-γ-lactone in germacrane-type sesquiterpenoids, and β-hydroxycarbonyl in pinguisane-type sesquiterpenoids play an important role in providing cytotoxic activity against both human promyelocytic leukemia (HL-60) and human pharyngeal squamous carcinoma (KB) cell lines. The structure of each isolated compound was elucidated by using spectroscopic methods and the cytotoxicity was determined by using the WST-8 colorimetric assay.
Chemosystematics of Porella (Marchantiophyta, Porellaceae)
Authors: Ludwiczuk Agnieszka , Gradstein S. Rob , Nagashima Fumihiro , Asakawa Yoshinori
Published: March 2019

The taxonomy of the liverwort genus Porella based on plant morphology has been regarded as difficult. Recent DNA-based studies have brought new insights into the systematics of these liverworts and have uncovered some novel relationships that allowed the resolution of controversial treatments based on morphology. One of the outstanding features of these plants, in addition to their form, is their chemical composition, which is characterized by great diversity of secondary metabolites. In this paper the sesqui- and diterpenoids occurring in Porella species are described and their chemosystematic relevance is explored. On the basis of chemical data, the Porella species have been divided into six chemotypes: the drimane- (I), sacculatane- (II), pinguisane-sacculatane- (III), guaiane-germacrane- (IV), pinguisane- (V) and africane- (VI) types. Species belonging to type I are characterized by their hot taste, whereas the other chemotypes are comprised of non-pungent species. Consideration of recent DNA data shows striking correlations between molecular groups and their terpenoid chemistry. The chemical data suggest that the P. vernicosa complex (chemotype I) deserves recognition as a separate section of Porella and that terpenoids are important chemosystematic markers in the family Porellaceae.
Chemical Constituents of Melicope ptelefolia
Authors: Shaari Khozirah , Zareen Seema , Akhtar Muhammad Nadeem , Lajis Nordin Hj.
Published: March 2019

Phytochemical investigations on the methanolic extract of Melicope ptelefolia Champ ex Benth. resulted in the isolation of three new compounds, identified as 3β-stigmast-5-en-3-ol butyl tridecanedioate (melicoester) (1), (2 Z,6 Z,10 Z,14 Z,18 Z,22 Z,26 E)-3′,7′,11′,15′,19′,23′,27′,31′-octamethyldotriaconta-2,6,10,14,18,22,26,30-octadecanoate (melicopeprenoate) (2) and p- O-geranyl-7″-acetoxy coumaric acid (3). The compounds were isolated along with twenty-one other known compounds, lupeol (4), oleanolic acid (5), kokusaginine (6) genistein (7), p-O-geranyl coumaric acid (8), 4-stigmasten-3-one (9), 3β-hydroxystigma-5-en-7-one (10) cis-phytyl palmitate (11), dodecane, dodecan-1-ol, ceryl alcohol, hentriacontanoic acid, eicosane, n-amyl alcohol, caprylic alcohol, octatriacontane, nonatriacontane, hexatriencontan-1-ol, methyl octacosanoate, β-sitosterol, β-sitosterol glucoside. Structures of all the compounds were established on the basis of MS and 1D and 2D NMR spectral data, as well as comparison with reported data.
Synthesis of a Natural γ-Butyrolactone from Nerylacetone by Acremonium roseum and Fusarium oxysporum Cultures
Authors: Gliszczyńska Anna , Świtalska Marta , Wietrzyk Joanna , Wawrzenczyk Czesłtaw
Published: March 2019

Natural γ-butyrolactone - (4 R, 5 R)-5-(4′-methyl-3′pentenyl)-4-hydroxy-5-methyl-dihydrofuran-2-one (2) was isolated as the product of microbial transformation of nerylacetone (1) by fungal strains. This product was obtained as the enantiomer (+) in high yields 24% and 61% with ee=94% and 82% by the biotransformation in the cultures of Acremonium roseum AM336 and Fusarium oxysporum AM13 respectively.
Myrtenal, a Controversial Molecule for the Proper Application of the CIP Sequence Rule for Multiple Bonds
Authors: Zepeda L. Gerardo , Burgueño-Tapia Eleuterio , Joseph-Nathan Pedro
Published: March 2019

This communication highlights the need of building hierarchical digraphs for the unequivocal assignment of stereochemical descriptors of (-)-myrtenal, a naturally-occurring oxygenated monoterpene whose absolute configuration (AC) is sometimes misrepresented in its structural formulae. Differentiation between duplicated atoms and phantom atoms for the proper application of the sequence rules is shown to be an essential step to get a proper construction of hierarchical digraphs.
Synthesis of Pterocarpans
Authors: Jiménez-González Leticia , Hernández-Cervantes Carmen , Álvarez-Corral Míriam , Muñoz-Dorado Manuel , Rodríguez-García Ignacio
Published: March 2019

The total synthesis of natural pterocarpans and analogs is reviewed.
Redox Properties of 8-Quinolinol and Implications for its Mode of Action
Authors: Chobot Vladimir , Drage Sigrid , Hadacek Franz
Published: March 2019

8-Quinolinol (oxine, 8-hydroxyquinoline) is a simple aromatic alkaloid with allelopathic, antibacterial, antifungal, and cytotoxic activities. Generally, it is assumed that 8-quinolinol toxicity depends on transition metal chelation that negatively affects their availability for metalloenzymes in the cell or reactive oxygen species generation (ROS), which are formed following reduction of molecular oxygen by autoxidation of the redox active metal central atom of the 8-quinolinol complex. On the contrary, beneficial effects of 8-quinolinol and its derivatives in the medication of certain degenerative diseases are known. In this context, the activity of 8-quinolinol derivatives is attributed to their antioxidant activity following iron complex formation. To address this controversial issue, we explore the possible anti- or pro-oxidant effects of 8-quinolinol and its iron complexes in the deoxyribose degradation assay, by cyclic voltammetry and in a biological assay. The antibacterial effects of 8-quinolinol and its complex with iron were evaluated on Curtobacterium flaccumfacies and Paenibacillus amylolyticus. 8-Quinolinol showed strong antioxidant activity in the deoxyribose degradation assay. This activity may not depend exclusively on iron chelation, but probably more on the notable reducing properties of 8-quinolinol; it proved to be a more efficient antioxidant than the flavonoids catechin and quercetin. By contrast, 8-quinolinol showed no pro-oxidative effects in the deoxyribose degradation assay, both in free form and in complex with iron, as it may occur with redox cyclers. Cyclic voltammetry confirmed this too. 8-Quinolinol significantly inhibited bacterial growth and respiration. Idiosyncratically, its 50:1 mixture with iron(III) ions was less active compared with free 8-quinolinol; it even caused a U-shaped nonlinear hormetic effect on growth and failed to inhibit respiration as totally as the pure mixture; the respiration was even accelerated compared with the control as a result of lower stress. Our results support the notion that complex formation with either iron or other transition metals affects the reducing power of 8-quinolinol, but, in contrast to general assumptions, this study finds no support that complex formation with iron represents the major mode of action.
Effect of Ascorbigen and 1′-Methylascorbigen on Disease Resistance of Bean Plants to Uromyces Phaseoli
Authors: Kátay György , Tyihák Ernő , Kátay Edith
Published: March 2019

The effect of ascorbigen and 1′-methylascorbigen on the disease resistance of bean (Phaseolus vulgaris L.,. cv. Debreceni Tarka) to the fungal pathogen Uromyces phaseoli Pers. is reported. Contrary to ascorbigen, pretreatment of bean plants with 1′-methylascorbigen, as in the case of other endogenous N-, O- and S-methyl compounds, induced the double immune response leading to the biochemical immunization of plants. The effectiveness of protection depended on the dosage of the applied 1′-methylascorbigen and on the time interval between the chemical pretreatment and inoculation. Results of our greenhouse experiments revealed, in accordance with previous results, that the presence of the N-methyl group in the 1′-methylascorbigen molecule is the precondition of the effect, and formaldehyde formed from this N-methyl group and its reaction products (e.g. singlet oxygen, ozone) can have a determining role in the manifestation of the effect.
The Thai Medicinal Plant Gynura Pseudochina var. hispida: Chemical Composition and in vitro NF-κB Inhibitory Activity
Authors: Siriwatanametanon Nisarat , Heinrich Michael
Published: March 2019

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-κB (Nuclear Factor kappa B) inhibitory activity and, therefore, was chosen for bioassay-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-dicaffeoylquinic acid (2), 4,5-dicaffeoylquinic acid (3), and 5-mono-caffeoylquinic acid (4). This paper discusses the current knowledge of these active components as NF-κB 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.
Fatty Acids as Chemotaxonomic Markers of Marine Macrophytes from Rio de Janeiro State, Brazil
Authors: Fleury Beatriz Grosso , Figueiredo Luciana , Marconi Márcia Iara , Teixeira Valéria Laneuville , Ferreira Aurélio Baird Buarque , Pinto Angelo C.
Published: March 2019

The distribution of fatty acids in 13 species of macroalgae (Chlorophyta, Ochrophyta and Rhodophyta) and 1 seagrass ( Spartina sp), collected on the Rio de Janeiro state coast was determined. The results were evaluated in search of correlations between the taxonomic and phylogenetic position of these macrophytes. Statistical analyses showed the effectiveness as taxonomic and phylogenetic markers of the distribution of the methyl fatty acid esters in these macrophytes.
Lecythomycin, a New Macrolactone Glycoside from the Endophytic Fungus Lecythophora sp
Authors: Sugijanto Noor Erma , Diesel Arnulf , Rateb Mostafa , Pretsch Alexander , Gogalic Selma , Zaini Noor Cholies , Ebel Rainer , Indrayanto Gunawan
Published: March 2019

A new macrolactone glycoside, lecythomycin (1), 23-methyl-3-(1- O-mannosyl)-oxacyclotetracosan-1-one, was isolated from the endophytic fungus Lecythophora sp. (code 30.1), an endopyte of the Indonesian plant Alyxia reinwardtii. The structure of 1 was elucidated on the basis of NMR spectroscopic and mass spectrometric data. The isolated compound displayed antifungal activity against strains of Aspergillus fumigatus and Candida kruzei at minimal inhibitory concentrations (MIC) of 62.5 – 125 μg/mL.
Concept of Biogenic Ferromanganese Crust Formation: Coccoliths as Bio-seeds in Crusts from Central Atlantic Ocean (Senghor Seamount/Cape Verde)
Authors: Wang Xiaohong , Peine Florian , Schmidt Alexander , Schröder Heinz C. , Wiens Matthias , Schloßmacher Ute , Müller Werner E.G.
Published: March 2019

At depths of 2,000 to 3,000 m, seamounts from the Cape Verde archipelago (Central Atlantic Ocean) are largely covered with ferromanganese crusts. Here we studied 60 to 150 mm thick crusts from the Senghor Seamount (depth: 2257.4 m). The crusts have a non lamellated texture and are covered with spherical nodules. The chemical composition shows a dominance of MnO2 (26.1%) and Fe2O3 (38.8%) with considerable amounts of Co (0.74%) and TiO2 (2.1%). Analysis by scanning electron probe microanalyzer (EPMA) revealed a well defined compositional zonation of micro-layers; the distribution pattern of Mn does not match that of Fe. Analysis by high resolution scanning electron microscopy (SEM) revealed that coccospheres/coccoliths exist in the crust material as microfossils; most of the coccospheres/coccoliths are not intact. The almost circular coccoliths belong to the type of heterococcoliths and are taxonomically related to species of the family Calcidiscaceae. By energy dispersive X-ray spectroscopic analysis an accumulation of the coccoliths in the Mn- and Fe rich micronodules was detected. Focused ion beam assisted SEM mapping highlighted that the coccoliths in the crust are Mn rich, suggesting that the calcareous material of the algal skeleton has been replaced by Mn-minerals. We conclude that a biologically induced mechanism has been involved in the formation of the crusts, collected from the Cape Verde archipelago from depths of 2,000 to 3,000 m in the mixing region between the oxygen-minimum surface zone and the oxygen-rich deep waters; the deposition process might have been triggered by chemical reactions during the dissolution of the Ca-carbonate skeletons of the coccoliths allowing Mn(II) to oxidize to Mn(IV) and in turn to deposit this element in the crust material.
Chionanthus Virginicus L.: Phytochemical Analysis and Quality Control of Herbal Drug and Herbal Preparations
Authors: Boyer Laurent , Baghdikian Béatrice , Bun Sok-Siya , Taoubi Khalil , Diaz-Lanza Ana , Elias Riad , Ollivier Evelyne
Published: March 2019

Root barks of Chionanthus virginicus L. are used in homeopathic medicines in the treatment of icterus and hepatitis. The objective of this study is to identify novel secoiridoids and lignans and to develop a simple and reliable HPLC method for the determination of oleuropein, phillyrin, total secoiridoids and total lignans for quality control and stability studies of C. virginicus herbal drug and preparations. Secoiridoids and lignans were purified by preparative HPLC. Compounds previously described were identified by HPLC according to their retention times and UV spectra. Structures of new compounds were determined by NMR. Two compounds namely excelside B and acetoxypinoresinol-4″- O-β-D-glucoside are described for the first time in the drug. HPLC separation was performed on Symmetry C18 (Waters) by gradient elution using acetonitrile and 0.2% aqueous phosphoric acid. The method was validated for specificity, linearity, precision, accuracy, limits of detection and quantification for simultaneous determination of secoiridoids and lignans in herbal drug and herbal preparations as mother tinctures. The proposed HPLC method is linear in the range studied (r2 ≥ 0.9989) for all the analytes. The method is precise with intra- and inter-day variations of less than 4%. The mean recoveries of the analytes range from 99.65 to 102.81%. The method is successfully applied to the quantification of nine compounds belonging to secoiridoids and lignans and for the stability studies of these compounds. The study allowed completing the phytochemical knowledge of C. virginicus. This simple developed assay could be used as tools for routine quality control of C. virginicus herbal drug and herbal medicinal products.
Evaluation of ent-Kaurenoic Acid Derivatives for their Anticariogenic Activity
Authors: de Andrade Bruna B. , Moreira Monique R. , Ambrosio Sérgio R. , Furtado Niege A. J. C. , Cunha Wilson R. , Heleno Vladimir C. G. , Silva Aline N. , Simão Marília R. , da Rocha Erilda M. P. , Martins Carlos H. G. , Veneziani Rodrigo C. S.
Published: March 2019

Ent-kaur-16(17)-en-19-oic acid (kaurenoic acid, KA) is a tetracyclic diterpene prototype for natural anticaries agents. Six KA derivatives were prepared and their antimicrobial activity against the main microorganisms involved in the caries process evaluated. The sodium salt of KA (KA-Na) was the most active, displaying very promising MIC values for most pathogens. Time-kill assays against the primary causative agent of caries ( Streptococcus mutans) indicated that KA and KA-Na only inhibited growth in the first 12 h, suggesting a bacteriostatic effect. After this period (12-24 h), their bactericidal effect was clearly noted. KA and KA-Na showed no synergy when combined with the gold standard anticariogenic (chlorhexidine dihydrochloride, CHD) in the checkerboard assays against S. mutans.
Chemical Constituents of the New Endophytic Fungus Mycosphaerella sp. nov. and Their Anti-parasitic Activity
Authors: Moreno Eufemio , Varughese Titto , Spadafora Carmenza , Arnold A. Elizabeth , Coley Phyllis D. , Kursar Thomas A. , Gerwick William H. , Cubilla-Rios Luis
Published: March 2019

Chemical investigation of a new endophytic fungus, Mycosphaerella sp. nov. strain F2140, associated with the foliage of the plant Psychotria horizontalis (Rubiaceae) in Panama, resulted in the isolation of cercosporin (1) and a new cercosporin analog (3) as the major components. The structures of minor compounds in the extract were elucidated by detailed spectroscopic analysis as 2-(2-butyl)-6-ethyl-3-hydroxy-6-methylcyclohex-2-ene-1, 5-dione (4), 3-(2-butyl)-6-ethyl-5-hydroxy-2-methoxy-6-methyl-cyclohex-2-enone (5), and an isomer of 5 (6). To study the influence of the hydroxy groups on the antiparasitic activity of cercosporin, compound 1 was acetylated to obtain derivative 2. The isolated compounds 1-6 were tested in vitro to determine their antiparasitic activity against the causal agents of malaria ( Plasmodium falciparum), leishmaniasis ( Leishmania donovani), and Chagas disease ( Trypanosoma cruzi). Cytotoxicity and potential anticancer activity of these compounds were evaluated using mammalian Vero cells and MCF7 cancer cell lines, respectively. Compounds 1 and 2 displayed high potency against L. donovani (IC50 0.46 and 0.64 μM), T. cruzi (IC50 1.08 and 0.78 μM), P. falciparum (IC50 1.03 and 2.99 μM), and MCF7 cancer cell lines (IC50 4.68 and 3.56 μM). Compounds 3-6 were not active in these assays at a concentration of 10 μg/mL.
Valine and Phenylalanine as Precursors in the Biosynthesis of Alkamides in Acmella Radicans
Authors: Cortez-Espinosa Nancy , Aviña-Verduzco Judit A. , Ramírez-Chávez Enrique , Molina-Torres Jorge , Ríos-Chávez Patricia
Published: March 2019

Acmella radicans (Asteraceae) produces at least seven alkamides, most with either an isobutyl- or phenylethyl group as the amine moiety. These moieties suggest that the amino acids valine and phenylalanine are the biosynthetic precursors of these alkamides. On the basis of labeled feeding experiments using either L-[2H8]valine or L-[2H8]phenylalanine we present evidence for the involvement of these two amino acids in the biosynthesis of (2 E,6 Z,8 E)- N-isobutyl-2,6,8-decatrienamide (affinin) (1), (2 Z,4 E)- N-(2-phenylethyl)-2,4-octadienamide (2), (2 E)- N-(2-phenylethyl)-nona-2-en-6,8-diynamide (3), and 3-phenyl- N-(2-phenylethyl)-2-propenamide (4). Alkamides were isolated from young A. radicans plants and analyzed by gas chromatography-mass spectrometry (GC-MS). Additionally, in cell free in vitro experiments based on isobutyl and phenylethylamide biosynthesis, using a colorimetric assay and GC-MS, valine and phenylalanine decarboxylase activities were assayed in the soluble extract of A. radicans leaves.
Acaricidal Activity against Tetranychus Urticae and Essential Oil Composition of Four Croton Species from Caatinga Biome in Northeastern Brazil
Authors: Neves Ilzenayde Araújo , da Camara Claudio Augusto Gomes
Published: March 2019

Volatile components of essential oils from the leaves and stems of Croton jacobinensis, C. rhamnifolius, C. muscicapa and C. micans, which are medicinal plants found in the Caatinga biome of northeastern Brazil, were analyzed using GC and GC/MS. The acaricidal activity of these oils against Tetranychus urticae was evaluated using the fumigation method. Oil yields from the Croton species ranged from 1.1±0.0 to 0.6±0.0%, w/w, for leaves and 0.7±0.0 to 0.1±0.0% for stems. Sesquiterpenoids were dominant in all oils, except the stem oil from C. rhamnifolius, which exhibited a high monoterpene content, and the leaf and stem oils from C. muscicapa, which were rich in phenylpropanoids. The major volatile components of the leaf and stem oils from C. jacobinensis were ( Z)-α-atlantone (24.3±0.4%) and trans-isolongifolanone (22.8±0.5%), respectively. The most abundant constituents detected in C. rhamnifolius were #aL-cedrene epoxide (23.3±0.1%) and caryophyllene oxide (21.9±0.0%) in the leaf oil, and camphor (16.6±0.5%) and tricyclene (12.8±0.1%) in the stem oil. Foenicolin was the main compound identified in the leaf (50.6±0.2%) and stem (72.7±0.6%) oils of C. muscicapa, while α-bulnesene (32.9±0.2%) and guaiol (17.9±0.7%) were the principal components of C. micans oils. These oils exhibited a high degree of toxicity in the fumigation assay. The stem oils from C. jacobinensis and C. rhamnifolius exhibited high lethality rates, with LC50 values of 0.3 and 0.2 μL/L of air after 24 h, respectively. The results suggest the potential use of stem essential oil, especially from C. rhamnifolius and C. jacobinensis, for the integrated control of Tetranychus urticae.
Composition and Antimicrobial Activity of Achillea Distans Essential Oil
Authors: Konakchiev Angel , Todorova Milka , Mikhova Bozhanka , Vitkova Antonina , Najdenski Hristo
Published: March 2019

The essential oil of Achillea distans W. et K. flower heads was analyzed by GC and GC-MS. Altogether 43 components in concentrations more than 0.1% were identified representing 93.5% of the oil composition. The main constituents were 1,8-cineole (16.8%), trans-thujone (9.8%), sabinene (8.2%), borneol (7.5%), β-pinene (6.5%), and camphor (5.8%). The oil showed moderate activity against Staphylococcus aureus and Candida albicans, and weak activity against Salmonella typhimurium, Proteus vulgaris, and Escherichia coli.
Citrus Bergamia Juice: Phytochemical and Technological Studies
Authors: Picerno Patrizia , Sansone Francesca , Mencherini Teresa , Prota Lucia , Aquino Rita Patrizia , Rastrelli Luca , Lauro Maria Rosaria
Published: March 2019

Fresh juice from bergamot ( Citrus bergamia Risso) has been studied to evaluate the polyphenolic composition by HPLC-DAD analysis and total polyphenols content by UV method. The main constituent, Naringin, has been selected as analytical and biological marker of the juice. Juice has been loaded onto maltodextrin matrix by spray-drying. The produced maltodextrin/juice powder (BMP) showed neither significant change in total polyphenols content nor decrease in antioxidant properties with respect to fresh juice. Moreover, BMP displayed high in vitro dissolution rate of the bioactive constituents in water and in simulated biological fluids. BMP appears as promising functional raw material for food, nutraceutical and pharmaceutical products. With this aim, a formulation study to develop tablets (BMT) for oral administration has been also performed. The produced solid oral dosage form preserved high polyphenols content, showed complete disaggregation in few minutes and satisfying dissolution rate of the bioactive constituents in simulated biological fluids.
Bioactivities of Chuquiraga Straminea Sandwith
Authors: Mendiondo María Elena , Juárez Berta E. , Zampini Catiana , Isla María Inés , Ordoñez Roxana
Published: March 2019

Methanolic extracts of Chuquiraga straminea Sandwith, subfamily Barnadesioideae (Asteraceae) showed the presence of quercetin-3- O-glucoside, quercetin-3- O-rutinoside, kaempferol, kaempferol-3- O-glucoside and kaempferol-3- O-rutinoside. Antioxidant and antimicrobial activity was determined. The total extracts showed antioxidant activity by DPPH and ABTS method (SC50 14.5 to 34.9 μg/mL). A significantly positive correlation was observed between the antioxidant activity and the total phenolics (R2>0.93). The extracts were active against ten methicillin resistant and sensitive Staphylococcus aureus strains isolated from nosocomial infection (MIC values between 200 to 800 μg/mL). These preliminary studies are highly interesting as they open new ways for further applications in the treatment of infections by methicillin resistant S. aureus.
Activity of Cuban Propolis Extracts on Leishmania Amazonensis and Trichomonas vaginalis
Authors: Fidalgo Lianet Monzote , Ramos Idalia Sariego , Parra Marley García , Cuesta-Rubio Osmany , Hernández Ingrid Márquez , Fernández Mercedes Campo , Piccinelli Anna Lisa , Rastrelli Luca
Published: March 2019

In this paper we analyzed the antiprotozoal effects of eighteen Cuban propolis extracts (brown, red and yellow type) collected in different geographic areas, using Leishmania amazonensis (as a model of intracellular protozoa) and Trichomonas vaginalis (as a model of extracellular protozoa). All evaluated propolis extracts caused inhibitory effect on intracellular amastigotes of L. amazonensis. However, cytotoxicity on peritoneal macrophages from BALB/c mice was observed. Only five samples decreased the viability of T. vaginalis trophozoites at concentrations lower than 10 μg/mL. No correlation between the type of propolis and antiprotozoal activity was found. Cuban propolis extracts demonstrated activity against both intracellular and extracellular protozoa model, as well as the potentialities of propolis as a natural source to obtain new antiprotozoal agents.
Chemical Composition and Biological Activity of Salvia Verbenaca Essential Oil
Authors: Canzoneri Marisa , Bruno Maurizio , Rosselli Sergio , Russo Alessandra , Cardile Venera , Formisano Carmen , Rigano Daniela , Senatore Felice
Published: March 2019

Salvia verbenaca L. (syn. S. minore) is a perennial herb known in the traditional medicine of Sicily as “spaccapetri” and is used to resolve cases of kidney stones, chewing the fresh leaves or in decoction. The chemical composition of the essential oil obtained from aerial parts of S. verbenaca collected in Piano Battaglia (Sicily) on July 2009, was analyzed by GC and GC-MS. The oil was strongly characterized by fatty acids (39.5%) and carbonylic compounds (21.2%), with hexadecanoic acid (23.1%), ( Z)-9-octadecenoic acid (11.1%) and benzaldehyde (7.3%) as the main constituents. The in vitro activity of the essential oil against some microorganisms in comparison with chloramphenicol by the broth dilution method was determined. The oil exhibited a good activity as inhibitor of growth of Gram + bacteria.
Secretory Cavities and Volatiles of Myrrhinium Atropurpureum Schott var. atropurpureum (Myrtaceae): An Endemic Species Collected in the Restingas of Rio de Janeiro, Brazil
Authors: Victório Cristiane Pimentel , Moreira Claudio B. , da Costa Souza Marcelo , Sato Alice , de Oliveira Arruda Rosani do Carmo
Published: March 2019

In this study, we investigated the leaf anatomy and the composition of volatiles in Myrrhinium atropurpureum var. atropurpureum endemic to Rio de Janeiro restingas. Particularly, leaf secretory structures were described using light microscopy, and histochemical tests were performed from fresh leaves to localize the secondary metabolites. To observe secretory cavities, fixed leaf samples were free-hand sectioned. To evaluate lipophilic compounds and terpenoids the following reagents were employed: Sudans III and IV, Red oil O and Nile blue. Leaf volatiles were characterized by gas chromatography after hydrodistillation (HD) or simultaneous distillation-extraction (SDE). Leaf analysis showed several cavities in mesophyll that are the main sites of lipophilic and terpenoid production. Monoterpenes, which represented more than 80% of the major volatiles, were characterized mainly by α- and β-pinene and 1,8-cineole. In order to provide tools for M. atropurpureum identification, the following distinguishing characteristics were revealed by the following data: 1) adaxial face clear and densely punctuated by the presence of round or ellipsoidal secretory cavities randomly distributed in the mesophyll; 2) the presence of cells overlying the upper neck cells of secretory cavities; 3) the presence of numerous paracytic stomata distributed on the abaxial leaf surface, but absent in vein regions and leaf margin; and 4) non-glandular trichomes on both leaf surfaces. Our study of the compounds produced by the secretory cavities of M. atropurpureum led us to conclude that volatile terpenoid class are the main secretory compounds and that they consist of a high concentration of monoterpenes, which may indicate the phytotherapeutic importance of this plant.
New Virescenosides from the Marine-derived Fungus Acremonium striatisporum
Authors: Afiyatullov Shamil Sh. , Kalinovsky Anatoly I. , Antonov Alexandr S.
Published: March 2019

Five new diterpene glycosides, virescenosides Z4-Z8 (1-5) have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures were determined by HRESIMS and 1D and 2D NMR. Virescenosides Z4-Z8 contain rare altruronic acid 4C1 and 1C4 conformations as their carbohydrate components. Virescenosides Z5 and Z7 exhibit an unusual 16-chloro, 15-hydroxyethylgroup as their side chains.
Gastroprotective Activity of Epitaondiol and Sargaol
Authors: Areche Carlos , San-Martín Aurelio , Rovinosa Juana , Sepúlveda Beatriz
Published: March 2019

The effects of epitaondiol (1) and sargaol (2), isolated from the brown alga Stypopodium flabelliforme on HCl/ethanol-induced gastric lesions in mice were evaluated and compared with that of lansoprazole. Epitaondiol and sargaol (6.25- 50 mg/kg) dose-dependently inhibited the appearance of gastric lesions in mice, displaying similar values to lansoprazole at 20 mg/kg. Both epitaondiol and sargaol showed gastroprotective activity with ED50 values of 40 mg/kg and 35 mg/kg, respectively. The results suggest that epitaondiol and sargaol protect the gastric mucosa in the HCl/EtOH model in mice.
A Set of Two Diastereomers of Cyanogenic Glycosides from Passiflora quadrangularis
Authors: Saeki Daisuke , Yamada Takeshi , Kajimoto Tetsuya , Muraoka Osamu , Tanaka Reiko
Published: March 2019

A set of two diastereomers of phenylcyano glycosides, (7 S)- and (7 R)-phenylcyanomethyl 1′- O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (1, 2), were isolated from the methanol extract of dried vines of P. quadrangularis. The absolute configurations of the benzylic methine centers were determined mainly by the comparison of 13C NMR spectra of these compounds, prunasin (3) and sambunigrin (4), of which the last two cyanoglycosides are known to have ( R)- and ( S)-configurations, respectively.
Antimicrobial Activity and Cytotoxic Effects of Magnolia dealbata and its Active Compounds
Authors: Jacobo-Salcedo Maria del Rosario , Gonzalez-Espindola Luis Angel , Alonso-Castro Angel Josabad , Gonzalez-Martinez Marisela del Rocio , Domínguez Fabiola , Garcia-Carranca Alejandro
Published: March 2019

Multi-drug resistance is of great concern for public health worldwide and necessitates the search for new antimicrobials from sources such as plants. Several Magnolia (Magnoliaceae) species have been reported to exert antimicrobial effects on sensitive and multidrug-resistant microorganisms. However, the antimicrobial properties of Magnolia dealbata have not been experimentally evaluated. The antimicrobial effects of an ethanol extract of Magnolia dealbata seeds (MDE) and its active compounds honokiol (HK) and magnolol (MG) were tested against the phytopathogen Clavibacter michiganensis subsp. michiganensis and several human multi-drug resistant pathogens using the disk-diffusion assay. The effects of MDE and its active compounds on the viability of human peripheral blood mononuclear cells (PBMC) were evaluated using MTT assay. MDE and its active compounds had antimicrobial activity (inhibition zone > 10 mm) against C. michiganensis, Pseudomonas aeruginosa, Acinetobacter baumannii, Acinetobacter lwoffii, Candida albicans, Candida tropicalis and Trichosporon belgeii. The results suggest that M. dealbata and its active compounds have selective antimicrobial effects against drug-resistant fungal and Gram (-) bacteria and exert minimal toxic effects on human PMBC.
Two Compounds from the Endophytic Colletotrichum sp. of Ginkgo biloba
Authors: Zhou Sheng-Liang , Zhou Song-Lin , Wang Mei-Xia , Chen Shuang-Lin
Published: March 2019

Two compounds, apigenin-8- C-β-D-glucopyranoside and 2-(hydroxymethylthio)ethanol, were extracted from the fermentation products of a strain of endophytic fungus, Colletotrichum sp. NTB-2, isolated from the leafstalk of Ginkgo biloba. The structures of the two compounds were determined on the basis of extensive spectroscopic analysis, including 1D and 2D NMR spectral data. The compounds were obtained from microorganisms for the first time.
Cordioxime: A New Dioxime γ-Lactam from Cordia platythyrsa
Authors: Christelle Tsague Dongmo , Hussain Hidayat , Dongo Etienne , Julius Oben Enyong , Hussain Javid
Published: March 2019

Cordia platythyrsa Baker is known for its medicinal value. This paper deals with a phytochemical investigation of this species, from which cordioxime (1), a new dioxime γ-lactam has been isolated. Its structure was determined by comprehensive analyses of its 1H and 13C NMR, COSY, HMQC, and HMBC spectroscopic, and HREIMS data. The remaining two known compounds were identified as β-sitosterol, and β-sitosterol glucopyranoside.
Influence of Viral Infection on Essential Oil Composition of Ocimum basilicum (Lamiaceae)
Authors: Nagai Alice , Duarte Lígia M.L. , Santos Déborah Y.A.C.
Published: March 2019

Ocimum basilicum L., popularly known as sweet basil, is a Lamiaceae species whose essential oil is mainly composed of monoterpenes, sesquiterpenes and phenylpropanoids. The contents of these compounds can be affected by abiotic and biotic factors such as infections caused by viruses. The main goal of this research was an investigation of the effects of viral infection on the essential oil profile of common basil. Seeds of O. basilicum L. cv. Genovese were sowed and kept in a greenhouse. Plants presenting two pairs of leaves above the cotyledons were inoculated with an unidentified virus isolated from a field plant showing chlorotic yellow spots and foliar deformation. Essential oils of healthy and infected plants were extracted by hydrodistillation and analyzed by GCMS. Changes in essential oil composition due to viral infection were observed. Methyleugenol and p-cresol,2,6-di- tert-butyl were the main constituents. However, methyleugenol contents were significantly decreased in infected plants.
A New Bisabolene from Stevia tomentosa
Authors: Valdez-Calderón Alejandro , Torres-Valencia J. Martín , Manríquez-Torres J. Jesús , Velázquez-Jiménez René , Gómez-Hurtado Mario A. , Román-Marín Luisa U. , Hernández-Hernández Juan D. , Cerda-García-Rojas Carlos M. , Joseph-Nathan Pedro
Published: March 2019

The new sesquiterpene (1 R,2 R,3 R,6 R,7 S)-1-acetoxy-2,3-dmydroxy-2,3-dihydrobisabolene (3) together with ten known terpenes and three known flavonoids were isolated from the aerial parts and from the roots of Stevia tomentosa. The structure of 3 follows from spectral studies, the relative chirality at C-3 follows from 1H NMR coupling constants comparison with the corresponding calculated values obtained by applying a generalized Karplus-type relationship to the dihedral angles of model compounds, and the absolute configuration is assumed in analogy to known (2 R,3 R,6 R,7 S)-2,3-epoxy-2,3-dihydrobisabolen-1-one (2).
Isolation and X-ray Structure of Deoxycholic Acid from the Sponge Ircinia sp
Authors: Singh Keisham Sarjit , Kaminsky Werner
Published: March 2019

Ethyl acetate extract of the sponge Ircinia sp., collected by SCUBA divers off the coast of southern India, contained a cholest-based sterol of insignificant antimicrobial activity, with one carboxylic acid side chain (3α, 7β-dihydroxy-5β-cholan-24-oic acid, DCA). The structure of the compound was determined by spectroscopic data and single crystal X-ray diffraction studies. DCA crystallizes in the tetragonal space group P41212, chirality documented by solution optical rotation [α]D = +67.4° ( c 0.16, CHCl3).
GC/MS Analysis of Three Amaryllidaceae Species and Their Cholinesterase Activity
Authors: Cahlíková Lucie , Benešová Nina , Macáková Kateřina , Urbanová Klára , Opletal Lubomír
Published: March 2019

Alzheimer's disease (AD), characterized by the death of nerve cells in the cerebral cortex, is the most common subtype of dementia. Despite the exponential growth in the number of AD patients, acetylcholinesterase (AChE) inhibitors are currently used to treat AD. Plants of the Amaryllidaceae family are known to synthesize a particular type of bioactive compounds, named Amaryllidaceae alkaloids, which have shown AChE inhibitory activity. Alkaloid extracts of three species of Amaryllidaceae were studied with respect to their acetylcholinesterase and butyrylcholinesterase inhibitory activity and alkaloid patterns. Eleven alkaloids were identified by GC/MS. Significant cholinesterase inhibitory activity was demonstrated by the alkaloid extract of N. undulata (IC50,HuAChE = 14.3 ± 1.2 μg/mL; IC50,HuBuChE = 33.9 ± 1.9 μg/mL).
Aqueous Extract from Vitis vinifera Tendrils is Able to Enrich Keratinocyte Antioxidant Defences
Authors: Fraternale Daniele , De Bellis Roberta , Calcabrini Cinzia , Potenza Lucia , Cucchiarini Luigi , Mancini Umberto , Dachà Marina , Ricci Donata
Published: March 2019

An aqueous extract of V. vinifera L. tendrils was evaluated for its ability to enrich the antioxidant capacity of cultured cells. The long-time antioxidant capability of the extract was measured by in vitro chemical methods, and its influence on reduced glutathione levels and plasma membrane oxido reductase activity was determined in cultured human keratinocytes (NCTC 2544). Keratinocytes are cells normally exposed to oxidative stress, and for this reason adequately equipped with antioxidant defences. However, it has long been suggested that exogenous antioxidants may play an important role in minimizing the adverse effects of oxidative stress on skin. We demonstrated that V. vinifera tendril aqueous extract was able to increase, in a time- and dose-dependent manner, the reduced glutathione concentration and activity of trans plasma membrane oxido reductase as an indirect evaluation of the intracellular redox status of the cells demonstrating a relevant antioxidant activity of this phytocomplex.
A New Acylated Neohesperidoside from Geranium purpureum
Authors: Şöhretoğrlu Didem , Liptaj Tibor , Sakar M. Koray , Sterner Olov
Published: March 2019

A new acylated neohesperoside derivative, 1-octyl-4′-isovaleroyl-neohesperoside (1), was isolated from Geranium purpureum Vili. (Geraniaceae) together with the known compounds quercetin-3-rutinoside and gallic acid. The identification of the isolated compounds was carried out by spectroscopic analysis including 1D- and 2D- NMR (1H, 13C, COSY, HSQC and HMBC) spectroscopy and ESI-TOF-MS.
Synthesis and Field Test of Three Candidates for Soybean Pod Borer's Sex Pheromone
Authors: Zhang Tao , Feng Juntao , Cai Chonglin , Zhang Xing
Published: March 2019

Three candidates for the soybean pod borer's sex pheromone, dodec-10-en-1-yl acetate ( E:Z = 95:5) (9a), ( E, E)-dodeca-8, 10-dien-1-yl acetate (9b) and ( E)-dodec-8-en-1-yl acetate (9c), were synthesized through the coupling reaction between Grignard reagents and acetates catalyzed by Li2CuCl4. Furthermore, the compounds 9a, 9b, and 9c, when tested in the field, showed that dodec-10-en-1-yl acetate ( E:Z = 95:5) (9a) has promise as a lure for male soybean pod borer.
Monitoring the Emission of Volatile Organic Compounds from Flowers of Jasminum sambac Using Solid-Phase Micro-extraction Fibers and Gas Chromatography with Mass Spectrometry Detection
Authors: Pragadheesh Vppalayam Shanmugam , Yadav Anju , Chanotiya Chandan Singh , Rout Prasanta Kumar , Uniyal Girish Chandra
Published: March 2019

Solid-phase microextraction (SPME) was studied as a solvent free alternative method for the extraction and characterization of volatile compounds in intact and plucked flowers of Jasminum sambac at different day time intervals using gas chromatography (GC-FID) and gas chromatography-quadrupole mass spectrometry. The analytes identified included alcohols, esters, phenolic compounds, and terpenoids. The main constituents identified in the flower aroma using different fibers were cis-3-hexenyl acetate, ( E)-β-ocimene, linalool, benzyl acetate, and ( E,E)-α-farnesene. The benzyl acetate proportion decreased from morning to afternoon and then increased in evening collections. PDMS fiber showed a high proportion of ( E,E)-α-farnesene in jasmine floral aroma. Among other constituents identified, cis-3-hexenyl acetate, linalool, and benzyl acetate were major aroma contributors in plucked and living flowers extracts using PDMS/DVB, Carboxen/PDMS, and DVB/Carboxen/PDMS fibers. PDMS/DVB recorded the highest emission for benzyl acetate while the ( E)-β-ocimene proportion was highest in DVB/Carboxen/PDMS when compared with the rest. The highest linalool content, with increasing proportion from morning to noon, was found using mixed coating fibers. Almost negligible volatile adsorption was recorded for the polyacrylate fiber for intact flower aroma, whereas it was most effective for benzyl acetate, followed by indole under plucked conditions. Moreover, the highest amounts extracted, evaluated from the sum of peak areas, were achieved using Carboxen/PDMS, and DVB/Carboxen/PDMS. Introduction of a rapid, and solvent free SPME method for the analysis of multicomponent volatiles can be successfully employed to monitor the extraction and characterization of flower aroma constituents.
Composition of Satureja kitaibelii Essential Oil and its Antimicrobial Activity
Authors: Kundaković Tatjana , Milenković Marina , Zlatković Saša , Kovačević Nada , Goran Nikolić
Published: March 2019

The composition of the essential oil obtained by hydrodistillation from the aerial parts of Satureja kitaibelii from Rtanj mountain (Serbia), collected during three years, was studied. Thirty-nine components were identified in each sample of S. kitaibelii essential oil, representing about 87% of the oils. p-Cymene was the most dominant compound in all three oils (27.9%, 14.7% and 24.4%, respectively). The simple formulation of a lozenge with 0.2% of S. kitaibelii essential oil was prepared and the antimicrobial activity of the essential oil and the lozenge with essential oil was tested using a broth microdilution assay. Both essential oil and lozenge possessed strong antimicrobial activity with MIC values of 0.10-25 μg/mL, and 0.97-15.6 mg/mL, respectively.
Composition and Antifungal Activities of the Leaf Essential Oil of Neolitsea parvigemma from Taiwan
Authors: Ho Chen-Lung , Liao Pei-Chun , Wang Eugene I-Chen , Su Yu-Chang
Published: March 2019

The hydrodistillated leaf essential oil of Neolitsea parvigemma was analyzed to determine its composition and yield. Sixty-two compounds were identified, the main components being β-caryophyllene (14.2%), β-eudesmol (12.9%), α-cadinol (10.2%) and τ-cadinol (8.8%). Oxygenated sesquiterpenes (48.9%) and sesquiterpene hydrocarbons (48.8%) were the predominant groups of compounds. The antifungal indexes of the leaf oil against the 7 fungi, Aspergillus clavatus, A. niger, Chaetomium globosum, Cladosporium cladosporioides, Myrothecium verrucaria, Penicillium citrinum and Trichoderma viride, were 100.0, 72.3, 100.0, 100.0, 100.0, 75.8 and 88.6% at a 1 mg/mL concentration, respectively. The oil also exhibited anti-wood-decay-fungi activity against Trametes versicolor, Phaneochaete chrysosporium, Phaeolus schweintizii, and Lenzites sulphureu with MIC values of 50, 50, 25 and 25 μg/mL, respectively. For the antifungal and anti-wood-decay fungal activities of the oil, the active source compounds were determined to be α-cadinol, β-eudesmol and τ-cadinol.
Evaluation of Clausena anisata Essential Oil from Cameroon for Controlling Food Spoilage Fungi and its Potential Use as an Antiradical Agent
Authors: Yaouba Aoudou , Tatsadjieu Léopold Ngoune , Dongmo Pierre Michel Jazet , Etoa François Xavier , Mbofung Carl Moses Fontum , Zollo Paul Henri Amvam , Menut Chantal
Published: March 2019

Investigations were conducted to determine the chemical composition, antifungal and antiradical activities of the essential oil extracted from the fresh leaves of Clausena anisata (Willd.) Hook. F. ex Benth (from Cameroon) against Aspergillus flavus, A. niger, A. parasiticus and Fusarium moniliforme. The essential oil obtained by hydrodistillation was analysed by GC and GC/MS. The disc diffusion method was used to evaluate the fungal growth inhibition at various concentrations of the oil while the antiradical activity of the essential oil was studied by the DPPH (diphenyl picryl hydrazyl) method. The main components obtained were E-ocimenone (15.1%), Z-ocimenone (11.5%), γ-terpinene (11.4%) and germacrene D (10.9%). After 10 days of incubation on essential oil supplemented medium, the growth of A. flavus, A. niger, A. parasiticus and F. moniliforme were totally inhibited by 4, 5, 5 and 5 mg/mL of C. anisata essential oil, respectively. The antiradical activity of C. anisata essential oil (SC50 = 5.1 g/L) was less than that of butylated hydroxyl toluene (BHT), which was used as the reference compound (SC50 = 0.007 g/L). Results obtained in the present study indicate the possibility of exploiting C. anisata essential oil to fight strains of A. flavus, A. niger, A. parasiticus and F. moniliforme responsible for biodeterioration of stored food products.