bluuebunny/crossref_metadata_2025 huggingface dataset:
Determination of Oxygen Radical Absorbance Capacity of Black Cumin (Nigella sativa) Seed Quinone Compounds
Authors: Tesarova Hana , Svobodova Blanka , Kokoska Ladislav , Marsik Petr , Pribylova Marie , Landa Premysl , Vadlejch Jaroslav
Published: March 2019

In this study, the antioxidant capacities of main quinone constituents of Nigella sativa seeds, namely dithymoquinone (1), thymohydroquinone (2) and thymoquinone (3), were compared using DPPH and ORAC methods. The best scavenging activity was produced by 2, which showed a remarkable activity of 2.60 Trolox equivalents (TE) in a concentration range between 1.6 and 6.4 μg/mL and IC50 value of 2.4 μg/mL in ORAC and DPPH assays, respectively. Contrastingly, 3 possessed only weak DPPH scavenging efficacy (IC50 = 170 μg/mL) but significant antioxidative action of 1.91 TE in ORAC assay. No effect has been observed for 1. Additionally, modified protocol for synthesis of 2 has been developed with aim to enhance its availability for further studies as well as for its future potential use. Based on the results of this study, we conclude that 2 could be considered as a compound with prospective antioxidative properties.
Generation of two New Macrolactones through Sequential Biotransformation of Dihydroresorcylide
Authors: Zeng Jia , Valiente Jonathan , Zhan Jixun
Published: March 2019

Biotransformation is an effective method to generate new derivatives from natural products. Combination of various enzymes or whole-cell biocatalysts creates new opportunities for natural product biosynthesis. Dihydroresorcylide (1) is a phytotoxic macrolactone from Acremonium aeae. It was first chlorinated at C-11 by an engineered Escherichia coli BL21-CodonPlus (DE3)-RIL/pJZ54 strain that overexpresses a fungal flavin-dependent halogenase, and subsequently glycosylated at 12-OH by Beauveria bassiana ATCC 7159, giving rise to a novel derivative, 11-chloro-4′- O-methyl-12- O-β-D-glucosyl-dihydroresorcylide (3). Although 1 can be converted into a new 4′- O-methyl-glucosylated derivative 4 by B. bassiana, this product cannot be further chlorinated by E. coli BL21-CodonPlus (DE3)-RIL/pJZ54 to afford 3. The sequence of these two biotransformation steps was thus restricted and not interchangeable. This sequential biotransformation approach can be applied to other structurally similar natural products to create novel derivatives.
Amides from the Stem of Capsicum annuum
Authors: Chen Chung-Yi , Yeh Yu-Ting , Yang Woei-Ling
Published: March 2019

7′-(4′-hydroxyphenyl)- N-[(4-methoxyphenyl)ethyl]propenamide (1), 7′-(3′,4′-dihydroxyphenyl)- N-[(4-methoxyphenyl)ethyl]propenamide (2), N-p-trans-coumaroyltyramine (3), N-trans-caffeoyltyramine (4), β-sitostenone (5), ferulic acid (6), hydroferulic acid (7), 5-hydroxy-3,4-dimethoxycinnamic acid (8), veratic acid (9), vanillic acid (10), isovanillic acid (11), syringic acid (12), (+)-syringaresinol (13), and pheophorbide a (14) were isolated from the stems of Capsicum annuum (Solanaceae). Among them, 1 is a new amide compound. The structures of these compounds were characterized and identified by spectral analyses.
Leishmanicidal and Cytotoxic Activities of Extracts and Naturally-Occurring Compounds from two Lauraceae Species
Authors: Sánchez-Suárez Jeysson , Coy-Barrera Ericsson , Cuca Luis Enrique , Delgado Gabriela
Published: March 2019

The in vitro leishmanicidal effects of ethanolic extracts and fifteen naturally-occurring compounds (five lignans, eight neolignans, a diterpene and a dihydrochalcone), obtained from Pleurothyrium cinereum and Ocotea macrophylla, were evaluated on promastigotes of Leishmania panamensis and L. braziliensis. In addition, in order to determine the selective action on Leishmania species as a safety principle, in vitro cytotoxicity on J774 cells was also evaluated for test compounds and extracts. One extract and seven compounds showed activity against Leishmania parasites at different levels. Dihydroflavokawin B (8) was found to be the most potent antileishmanial compound on both parasites, whilst (+)-otobaphenol (14), was found to be the most selective compound on L. panamensis.
Micromorphology of Glandular hairs, Biological Activity and Composition of the Essential Oil of Tanacetum fisherae (Asteraceae-Anthemideae) from Iran
Authors: Rajaei Peyman , Nejadsattari Taher , Maassoumi Ali Asghar , Mozaffarian Valiollah , Sonboli Ali
Published: March 2019

The essential oil was obtained from the aerial flowering parts of Tanacetum fisherae, a new record from Iran, by hydrodistillation and analyzed by GC and GC-MS. Eleven components representing 99.9% of the total oil were identified. 1,8-Cineole (79.9%) was characterized as the principal compound. The essential oil and its main component were tested against nine microbial strains. The result of the bioassays revealed that the oil possess potent antimicrobial property. This may be associated due to the presence of 1,8-cineole in the oil which tested individually and its high activity was observed. Micromorphological studies of hairs by scanning electron microscopy (SEM) exhibited the presence of abundant sessile capitate glandular and medifixed T-shaped eglandular trichomes on the leaves, flowers and achene, giving useful diagnostic characters for identification of this medicinal plant.
Antimicrobial Activity and Chemical Constituents of the Essential Oils from Flower, Leaf and Stem of Gypsophila bicolor from Iran
Authors: Shafaghat Ali , Shafaghatlonbar Masoud
Published: March 2019

The volatile constituents from flower, leaf and stem of Gypsophila bicolor growing in Iran were obtained by hydrodistillation and analyzed by GC and GC/MS. The flower oil was characterized by high amounts of germacrene-D (21.2%), p-cymene (20.6%), bicyclogermacrene (17.6%), γ-dodecadienolactone (13.7%) and terpinolene (9.4%). Twenty-four constituents representing 97.4% of the leaf oil were identified of which germacrene-D (23.4%), terpinolene (14.5%), bicyclogermacrene (7.5%), γ-dodecadienolactone (6.8%), p-cymene (6.7%) and cis-β-ocimene (6.3%) were major components. The main components of the stem oil were γ-dodecadienolactone (28.5%), bicyclogermacrene (14.8%), germacrene-D (12.6%), p-cymene (12.5%), terpinolene (11.6%) and trans-β-ocimene (4.2%). The antimicrobial effects of flower, leaf and stem essential oils from Gypsophila bicolor were studied according to the agar diffusion cup method. The essential oils had a moderate effect on the Gram-positive and Gram-negative bacteria, but had a substantial effect on the fungi studied.
Antimicrobial Activity of the Essential Oil of Greek Endemic Stachys spruneri and its Main Component, Isoabienol
Authors: Koutsaviti Aikaterini , Milenković Marina , Tzakou Olga
Published: March 2019

The essential oils of Stachys spruneri Boiss. (sample A and sample B) were analyzed by GC and GC-MS. (+)-Isoabienol was the dominant component (49.5 and 48.2%, respectively of the total oils) among seventy-two identified constituents. Isoabienol was separated, purified by preparative thin-layer chromatography, and further identified by means of physicochemical and spectrometric analysis. The microbial growth inhibitory properties of the essential oil and its main metabolite, the labdane diterpene isoabienol, were determined using the broth microdilution method against eight laboratory strains of bacteria (Gram- positive: Staphylococcus aureus, S. epidermidis, Micrococcus luteus, Enterococcus faecalis, Bacillus subtilis, and Gram- negative: Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, and two strains of the yeast Candida albicans. Both essential oil and isoabienol showed considerable activity against all the microorganisms tested, with the isolated compound being most active.
Pharmacological Developments Obtained from Marine Natural Products and Current Pipeline Perspective
Authors: Elkin Galeano J. , Rojas Jhon J. , Martínez Alejandro
Published: March 2019

Marine organisms represent a new extensive source for bioactive molecules. They have the potential to provide new therapeutic alternatives to treat human diseases. In this paper, we describe and discuss a variety of isolated and semisynthetic molecules obtained from marine sources. These compounds are in phase II, phase III and at the commercialization stage of new drug development. A description of the mechanism of action, dosage used and side effects are also reported. The positive results obtained from these studies have triggered the development of new studies to evaluate the prospects for utilization of marine organisms.
Total Synthesis of the Bicyclic Marine Sesquiterpenoid Drechslerine B
Authors: Hagiwara Hisahiro , Fukushima Masakazu , Kinugawa Kimihiko , Matsui Takuya , Hoshi Takashi , Suzuki Toshio
Published: March 2019

The total synthesis of the recently isolated bicyclic sesquiterpenoid drechslerine B (2), isolated from the algicolous fungus Drechslera dematioidearare in the marine red alga Liagora viscida, has been achieved, starting from ( S)-carvone (8), via an intramolecular aldol reaction and palladium-catalyzed carbon monoxide insertion as key reactions.
The Quaternary Indole Alkaloids from Two Sumatran Lerchea species
Authors: Arbain Dayar , Syafni Nova , Friardi  , Putra Deddi Prima , Komala Ismiarni , Yamaguchi Kentaro , Asakawa Yoshinori
Published: March 2019

The Sumatran forest plants Lerchea cf. bracteata and L. parviflora were found to contain alkaloids and their extract showed siginificant activity toward some testing pathogenic microbes. Isolation work on L.cf. bracteata yielded known quaternary alkaloid N(b)-methylantirhine (2) while L. parviflora gave 5,6-dihydroflavopereirine (3).
New Acrylamide and Oxazolidin Derivatives from a Termite-Associated Streptomyces sp
Authors: Bi Shu Feng , Li Fang , Song Yong Chun , Tan Ren Xiang , Ge Hui Ming
Published: March 2019

Two new compounds, named 2-formylpyrrole-4-acrylamide (1) and dihydrostreptazolin (2) were isolated from the fermentation broth of BY-4, an actinomycetes residing in the gut of Odontotermes formosanus. The structures of 1 and 2 were elucidated by extensive spectral analysis (1H, 13C, 2D NMR, and HRESIMS). The isolated compounds were assayed for cytotoxic and antimicrobial activities.
Characteristic Volatile Components of Kabosu (Citrus sphaerocarpa Hort. ex Tanaka)
Authors: Tomiyama Kenichi , Aoki Hirokazu , Oikawa Takeshi , Sakurai Kazutoshi , Kasahara Yoko , Kawakami Yukihiro
Published: March 2019

The volatile components of both peel and juice of Japanese citrus, Kabosu ( Citrus sphaerocarpa Hort. ex Tanaka) were investigated using SAFE (Solvent Assisted Flavor Evaporation) technique after solvent extraction. In this study, wine lactone, rose oxide, (2 E)-4,5-epoxy-2-decenal, mintsulfide, and indole were newly identified from Kabosu. AEDA (Aroma Extract Dilution Analysis) of the oxygenated fraction of the peel extract showed high FD (Flavor Dilution) factors for linalool, (2 E)-4,5-epoxy-2-decenal, octanal, (4 Z)-decenal, β-citronellol, geraniol, and wine lactone, while wine lactone, linalool, eugenol, geraniol, and (2 E)-4,5-epoxy-2-decenal from the juice extract. The enantiomeric distribution of linalool, cis-rose oxide, β-citronellol, and wine lactone were also determined using a multidimensional chiral GC/MS.
Essential Oil of Plectranthus tenuicaulis Leaves from Gabon, Source of (R),(E)-6,7-Epoxyocimene. An Unusual Chemical Composition within the Genus Plectranthus
Authors: Agnaniet Huguette , Agrebi Abdelhamid , Bikanga Raphaël , Makani Thomas , Lebibi Jacques , Casabianca Hervé , Morère Alain , Menut Chantal
Published: March 2019

Water distilled essential oils from leaves of Plectranthus tenuicaulis (Hook. f.) J. K. Morton collected in Gabon were analyzed using GC-FID and GC-MS. The main constituent, unusual within the genus Plectranthus, was isolated and formally identified as being the (+)-( R)-enantiomer of ( E)-6,7-epoxyocimene [( E)-myroxide]. This enantiomer, which represents about 75% of the essential oil, has been previously identified as a pheromone emitted by the male fruit-spotting bug Amblypelta nitida; this insect is responsible of destruction of most fruit crops in tropical and subtropical areas. The potential application of P. tenuicaulis essential oil in crop protection programs is discussed and the atypical chemical profile of the gabonese essential oil is compared with those previously reported in the genus Plectranthus (or Coleus).
Botcinolide/Botcinin: Asymmetric Synthesis of the Key Fragments
Authors: Ramírez-Fernández Jacinto , Botubol José Manuel , Bustillo Antonio J. , Aleu Josefina , Collado Isidro G. , Hernández-Galán Rosario
Published: March 2019

The asymmetric synthesis of key fragments of the phytotoxic toxins botcinolide/botcinin is reported. The synthesis of 1 and 1a are based on a convergent route via esterification and alkene metathesis of fragments A, B or C, B, which were obtained by Evans aldol condensation and stereoselective crotylation, respectively.
Aconitum lipo-alkaloids – Semisynthetic Products of the Traditional Medicine
Authors: Borcsa Botond , Csupor Dezső , Forgo Peter , Widowitz Ute , Bauer Rudolf , Hohmann Judit
Published: March 2019

The term lipo-alkaloid is used for C19 aconitane alkaloids containing one or two long-chain fatty acid residues. Lipo-alkaloids are transesterified derivatives of the most toxic and highly effective diester-type diterpene alkaloids, such as aconitine, hypaconitine, mesaconitine. Lipo-alkaloids are native minor compounds of aconite drugs, but their amount significantly increases after traditional processing, which is a general method in the Far Eastern traditional medicinal systems. Analytical works demonstrated that cautious processing (usually boiling) of crude aconite roots decreases the amount of normal diterpene alkaloids and increases the concentration of lipo-alkaloids resulting in the reduction of toxicity of the drugs. Many papers reported that lipo-alkaloids occur as a complex mixture in the drugs, and the isolation of the individual components is extremely difficult. These compounds have been identified using highly sensitive analytical methods (HPLC-MS, NMR), and semisynthetic approaches have been developed to ensure lipo-alkaloids in pure form for pharmacological studies.

This review summarizes the structure, chemistry, semisynthesis, analytics and bioactivities of lipo-alkaloids. On the basis of 32 references this is the first comprehensive study on this topic, covering the data of 173 compounds.
Bioactivity-guided Study of Antiproliferative Activities of Salvia Extracts
Authors: Janicsák Gábor , Zupkó István , Nikolova Milena T. , Forgo Peter , Vasas Andrea , Máthé Imre , Blunden Gerald , Hohmann Judit
Published: March 2019

The cytotoxic activities of the n-hexane, chloroform and aqueous methanolic fractions prepared from the methanolic extract of the leaves of 23 Salvia taxa were studied for their cell growth-inhibitory activity against human cervix adenocarcinoma (HeLa), skin carcinoma (A431) and breast adenocarcinoma (MCF7) cells using the MTT assay. The n-hexane fractions of six Salvia taxa (S. hispanica, S. nemorosa, S. nemorosa l. albiflora, S. pratensis, S. recognita and S. ringens) and the chloroform fraction of S. officinalis l. albiflora produced over 50% growth inhibition of the skin carcinoma cell line. None of the tested extracts showed substantial (above 50%) antiproliferative effects against HeLa and MCF7 cells. S. ringens was the most powerful among the studied Salvia species with a 61.8% cell growth inhibitory activity on A431 cells. In the case of S. ringens, other plant parts were also tested for antiproliferative effect, and the highest activities were recorded for the root extract. This was subjected to bioactivity-guided fractionation, which yielded four abietane diterpenes (royleanone, horminone, 7- O-methyl-horminone and 7-acetyl-horminone), one triterpene (erythrodiol-3-acetate) and β-sitosterol. Horminone, 7-acetyl-horminone and erythrodiol-3-acetate displayed marked concentration-dependent antiproliferative effects, while royleanone and 7 -O-methyl-horminone produced weaker activities.
Radioprotective Properties of Cumaside, a Complex of Triterpene Glycosides from the Sea Cucumber Cucumaria Japonica and Cholesterol
Authors: Aminin Dmitry L. , Zaporozhets Tatiana S. , Adryjashchenko Pelageya V. , Avilov Sergey A. , Kalinin Vladimir I. , Stonik Valentin A.
Published: March 2019

The radioprotective activity has been studied of a new immunomodulatory lead material, Cumaside, which is a complex of monosulfated triterpene glycosides from the edible sea cucumber Cucumaria japonica and cholesterol. Female CD-1 strain mice administered with prophylactic doses of Cumaside were irradiated using a Gamma-therapeutic device with a 60Co source (exposure dose 6.5 Gy, dose rate 1.14 Gy /min) and the average life span of the mice was determined. The animals administrated with Cumaside and irradiated were killed by pervisceral dislocation on days 4 and 9. Peripheral blood cell composition indexes, blood forming function and cell number in blood-forming organs and the number of pluripotent blood-forming stem cells were determined using standard procedures and the results compared with those of non-treated irradiated mice. The survivability percentage and average life span of the irradiated mice that were not treated with Cumaside were decreased in comparison with the Cumaside-treated groups. Especially, the leukocyte and neutrophil numbers in the blood (bone marrow from hip), and the weight and cell number of lymphoid organs were higher in the Cumaside-treated groups compared with the non-treated irradiated mice. It was concluded that at low prophylactic doses Cumaside possesses moderate radioprotective properties.
Analysis of Amaryllidaceae Alkaloids from Chlidanthus Fragrans by GC-MS and their Cholinesterase Activity
Authors: Cahlíková Lucie , Macáková Kateřina , Zavadil Stanislav , Jiroš Pavel , Opletal Lubomír , Urbanová Klára , Jahodář Luděk
Published: March 2019

The underivatized alkaloid mixture extracted from the bulbs of Chlidanthus fragrans Herb. was investigated by capillary GC/MS for the first time. Fifteen known Amaryllidaceae alkaloids of five structure types were identified. The main alkaloids were tazzetine (9, tazettine-type), chlidanthine (2, galanthamine-type), belladine (8, belladine-type) and lycorine (12, lycorine-type). The alkaloid extract from the bulbs showed promising human blood acetylcholinesterase (IC50 = 20.1 ± 2.9 μg/mL) and human plasma butyrylcholinesterase (IC50 = 136.8 ± 6.9 μg/mL) inhibitory activity.
Unusual Compounds from Exudates of Dionysia Diapensifolia and D. gaubae var. megalantha (Primulaceae)
Authors: Bhutia Tshering Doma , Valant-Vetschera Karin M. , Lorbeer Eberhard , Brecker Lothar
Published: March 2019

Exudates of Dionysia diapensifolia yielded ( R)-(+)-3-acetoxy-3-phenyl-propiophenone as a new natural product with a basic dihydrochalcone structure, which was elucidated unequivocally by mass spectrometry and NMR spectroscopy. The sesquiterpenoid carissone was found as the major compound in the exudate of D. gaubae var. megalantha. Sesquiterpenoids have so far not been described as exudate constituents of Primula and Dionysia. Structural identifications are discussed in detail, and the significance of the occurrence of these unusual compounds in exudates of Primulaceae is shortly addressed.
A Novel Biflavonyloxymethane from Pongamia Pinnata and its Radical Quenching Activity
Authors: Ghosh Anindita , Mandal Suvra , Banerji Avijit , Kar Manoj , Hazra Kalyan , Banerji Julie
Published: March 2019

The root bark of Pongamia pinnata Pierre (syn P. glabra Vent.) has afforded a new biflavonyloxymethane, pongabiflavone, along with a known furanoflavone, 3-methoxy-(7, 8, 2″, 3″) furanoflavone. The structure of this new compound was elucidated from extensive spectral studies, including 2D-NMR spectroscopic experiments. The antioxidant, radical quenching activity- superoxide and nitric oxide quenching activities of both pongabiflavone and previously isolated karanjabiflavone have been evaluated which can be a key to cure Psoriasis.
Multiple Beneficial Effects of Resveratrol and their Chemical-Biochemical Basis
Authors: Tyihák Ernő , Király-Véghely Zsuzsa , Móricz Ágnes M.
Published: March 2019

On the basis of in vitro and in vivo investigations trans-resveratrol (RV) is a natural, concentration-dependent formaldehyde (HCHO) mobilizer, scavenger, capture and carrier molecule. The capturing and mobilization of HCHO from a given biological unit (e.g. tissue) with RV (first step) generates a chemopreventive effect. The reaction products between endogenous HCHO and RV (second step) may exert killing/inhibiting effects on pathogens and/or cancer cells. These two steps result in the double effect of RV. From the model reaction mixture of RV and HCHO in diluted formalin solution, different reaction products were detected, separated and identified. Similar reactions can be observed between RV and endogenous HCHO in plant and animal tissues as well. Capturing the HCHO molecules in model experiments with HCHO-capture molecules (in vitro conditions) the antibacterial activity of RV decreased substantially. The in vitro investigations were extended to in vivo conditions. The discovery of a quadruple immune response of plants to pathogens resulting from pretreatment with RV opens new horizons in the confirmation of the diverse beneficial effects of RV.
Antioxidant Activity of Polyphenols from Green and Toasted Mate Tea
Authors: de Abreu Marques Coentrão Patrícia , Teixeira Valéria Laneuville , Pereira Netto Annibal Duarte
Published: March 2019

The production and distribution of toasted mate tea in Brazil has increased, which has resulted in its greater consumption. Mate tea is obtained by roasting non-fermented erva-mate in order to produce toasted erva-mate or toasted mate tea. However, although the product is much appreciated, studies of its chemical composition and the concentration of polyphenols, particularly flavonols present in toasted mate tea, are few and often controversial. This paper elucidates some misunderstandings involving the nomenclature of erva-mate and toasted mate, and mainly provides an overview of the composition of polyphenols and antioxidant capacity of toasted mate tea and its raw material, erva-mate, in comparison with other teas, the compositions of which were found in the literature.
Bioactive Aromatic Derivatives from Endophytic Fungus, Cytospora sp
Authors: Lu Shan , Draeger Siegfried , Schulz Barbara , Krohn Karsten , Ahmed Ishtiaq , Hussain Hidayat , Yi Yanghua , Li Ling , Zhang Wen
Published: March 2019

Two new benzyl γ-butyrolactone analogues, ( R)-5-(( S)-hydroxy(phenyl)-methyl)dihydrofuran-2(3H)-one (1) and its 6-acetate (2), and a new naphthalenone derivative (8), together with eight additional known aromatic derivatives, ( S)-5-(( S)-hydroxy(phenyl)-methyl)dihydrofuran-2(3H)-one (3), ( S)-5-benzyl-dihydrofuran-2(3H)-one (4), 5-phenyl-4-oxopentanoic acid (5), γ-oxo-benzenepentanoic acid methyl ester (6), 3-(2,5-dihydro-4-hydroxy-5-oxo-3-phenyl-2-furyl)propionic acid (7), (3 R)-5-methylmellein (9), integracins A (10) and B (11) were isolated from Cytospora sp., an endophytic fungus isolated from Ilex canariensis from Gomera. The structures of these compounds were elucidated by detailed spectroscopic analysis, comparison with reported data, and chemical interconversion. The absolute configurations of the new compounds (1, 2, 8) were established on the basis of optical rotation or CD spectra analysis. Preliminary studies showed antimicrobial activity of these compounds against the fungi Microbotryum violaceum, Botrytis cinerea and Septoria tritici, the alga Chlorella fusca, and the bacterium Bacillus megaterium.
Antiprotozoal, Antitubercular and Cytotoxic Potential of Cyanobacterial (Blue-Green Algal) Extracts from Ireland
Authors: Broniatowska Barbara , Allmendinger Andrea , Kaiser Marcel , Montamat-Sicotte Damien , Hingley-Wilson Suzie , Lalvani Ajit , Guiry Michael , Blunden Gerald , Tasdemir Deniz
Published: March 2019

Cyanobacteria (= blue-green algae) are prolific producers of structurally distinct and biologically active metabolites. In the continuation of our search for new sources of anti-infective natural products, we have assessed the in vitro antiprotozoal ( Plasmodium falciparum, Trypanosoma brucei rhodesiense, T. cruzi, Leishmania donovani) and antitubercular ( Mycobacterium tuberculosis) potential of samples of two terrestrial cyanobacteria, Nostoc commune (collected when desiccated and wet) and Rivularia biasolettiana. The cytotoxic potential of the extracts was also evaluated against primary L6 cells. Except for T. cruzi and M. tuberculosis, the crude extracts were active against all the organisms tested and showed no toxicity. The crude extracts were then partitioned between n-hexane, chloroform and aqueous methanol and retested against the same panel of pathogens. The chloroform sub-extracts of both N. commune samples showed significant activity against T. b. rhodesiense (IC50 values 2.0 and 3.5 μg/mL) and P. falciparum (IC50S 7.4 and 5.8 μg/mL), with low toxicity. This trend was also true for R. biasolettiana extracts, and its chloroform sub-extract showed notable activity against all parasitic protozoa. There were differences in the biological activity profiles of extracts derived from desiccated and hydrated forms of N. commune. To our knowledge, this is the first study assessing the anti-infective activity of desiccated and hydrated forms of N. commune, as well as R. biasolettiana. Furthermore, the present work reports such biological activity in terrestrial cyanobacteria from Ireland for the first time. These results warrant the further study of Irish terrestrial cyanobacteria as a valuable source of new natural product leads for the treatment of parasitic protozoal infections.
Chemical Diversity of Ziziphora Clinopodioides: Composition of the Essential oil of Z. clinopodioides from Tajikistan
Authors: Sharopov Farukh S. , Setzer William N.
Published: March 2019

The chemical composition of the essential oils of Ziziphora clinopodioides Lam. from the aerial flowering parts, collected during two different years, were obtained by hydrodistillation and analyzed by gas chromatography – mass spectrometry. Forty-five components representing 100% and 94.7% of the total oil were identified. The main constituents of the essential oils were pulegone (72.8 and 35.0%), neomenthol (6.5 and 23.1%), menthone (6.2 and 13.3%), p-menth-3-en-8-ol (1.7 and 3.5%), piperitenone (2.6 and 1.1%) and piperitone (0.7 and 1.2%). A cluster analysis was carried out on the essential oil compositions of Z. clinopodioides.
Essential Oil Composition of Five Collections of Achillea Biebersteinii from Central Turkey and their Antifungal and Insecticidal Activity
Authors: Tabanca Nurhayat , Demirci Betül , Gürbüz İlhan , Demirci Fatih , Becnel James J. , Wedge David E. , Can Başer Kemal Hüsnü
Published: March 2019

The composition of the essential oils hydrodistilled from the aerial parts of five Achillea biebersteinii Afan samples, collected in central Turkey from Konya, Isparta and Ankara, were analyzed both by gas chromatography (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Eighty-four components were identified, representing 87 to 99% of the total oil composition. The identified major components were 1,8-cineole (9-37%), camphor (16-30%) and p-cymene (1-27%). Two samples differed in piperitone (11%) and ascaridol (4%) content. The five A. biebersteinii essential oils were subsequently evaluated for their antifungal activity against the strawberry anthracnose-causing fungal plant pathogens Colletotrichum acutatum, C. fragariae and C. gloeosporioides using the direct overlay bioautography assay. The essential oils showed no antifungal activity at 80 and 160 μg/spot. In addition, A. biebersteinii oils and their major compounds were subsequently investigated against Aedes aegypti first instar larvae in a high throughput bioassay. Among the oils, only one sample from Ankara showed a notable larvacidal effect on Ae. aegypti larvae. The major compounds, 1,8-cineole, camphor and p-cymene, exhibited low mosquito larval activity, and thus the minor compounds are probably responsible for the observed activity against Ae. aegypti larvae. The oils showed weak activity against adult Ae. aegypti.
Overpressured Layer Chromatography (OPLC) – A Flexible Tool of Analysis and Isolation
Authors: Mincsovics Emil , Tyihák Ernő
Published: March 2019

This review briefly summarizes the overpressured layer chromatography (OPLC) technique and its progress from the beginning until today. Some theoretical aspects, important technical and methodological solutions, as well as analytical separations and isolations are demonstrated covering the last 30 years. The infusion and transfusion OPLC operations, as well as their combination, and their off-line and online processes, and off-line and online hyphenations for detection and structure elucidation are presented. The combination of OPLC separation with biological detection by direct bioautography and BioArena as an important solution touches the potential of analysis and isolation based on biological activity.
Iridoid Glucosides from Wendlandia Tinctoria roots
Authors: Dinda Biswanath , Debnath Sudhan , Banik Rajarshi , Sato Noriko , Harigaya Yoshihiro
Published: March 2019

A new iridoid glucoside, 8- O-( E)-caffeoylmussaenosidic acid (1), together with ixoside (2), was isolated from the roots of Wendlandia tinctoria. The structure of the new compound was established on the basis of detailed spectroscopic (2D NMR) and chemical analysis.
Solid State Structure and Absolute Configuration of Filifolinol Acetate
Authors: Muñoz Marcelo A. , Urzúa Alejandro , Echeverría Javier , Modak Brenda , Joseph-Nathan Pedro
Published: March 2019

Careful reevaluation of the 1H and 13C NMR spectroscopic data of filifolinol acetate (4) led to the reassignment of the C-10 and C-11 signals, as well as the gem-dimethyl signals. Single crystal X-ray analysis provided an independent structural confirmation of 4, and comparison of the experimental vibrational circular dichroism spectrum with calculations performed using density functional theory provided the absolute configuration of this 3H-spiro-1-benzofuran-2,1′-cyclohexane and related molecules.
A Novel Sesquiterpene Alcohol from Fimetariella Rabenhorstii, an Endophytic Fungus of Aquilaria sinensis
Authors: Tao Mei-Hua , Yan Jian , Wei Xiao-Yi , Li Dong-Li , Zhang Wei-Min , Tan Jian-Wen
Published: March 2019

A novel sesquiterpene alcohol, named frabenol (1), was isolated from liquid cultures of Fimetariella rabenhorstii A20, an endophytic fungus of the agarwood-forming plant Aquilaria sinensis (Lour.) Gilg. The structure of the new compound was elucidated on the basis of spectroscopic methods. The finding of a sesquiterpenoid compound in F. rabenhorstii A20 implied that endophytic fungi of agarwood-producing plants could also contribute to the generation of fragrant chemicals during the agarwood formation processes.
Chemical Composition of Argentinean Propolis Collected in Extreme Regions and its Relation with Antimicrobial and Antioxidant Activities
Authors: Vera Nancy , Solorzano Eliana , Ordoñez Roxana , Maldonado Luis , Bedascarrasbure Enrique , Isla María I.
Published: March 2019

This paper reveals, for the first time, the functional properties of propolis from an extreme region of Argentine ( El Rincón, Province of Catamarca, Argentina), as well as the isolation and identification of bioactive compounds. The antioxidant activity was determined by the ABTS method and β-carotene bleaching. The antibacterial activity was determined on methicillin resistant Staphylococcus aureus (MRSA) by the microdilution method and bioautographic assays. Twelve compounds were isolated and identified by NMR spectroscopy. The main bioactive compounds were 2′,4′-dihydroxy-3′-methoxychalcone (3), 2′,4′-dihydroxychalcone (9), 2′,4′,4-trihydroxy-6′- methoxychalcone (8), 5-hydroxy-4′,7-dimethoxyflavone (4), 4′,5-dihydroxy-3,7,8-trimethoxyflavone (10) and 7-hydroxy- 5,8-dimethoxyflavone (11). All compounds were active against clinical isolates (MIC50 10 μg/ mL) and displayed antioxidant activity (SC50 values of 20 μg/mL). The MIC and SC50 values of the isolated compounds were lower than those obtained with crude propolis extracts, chloroform sub-extracts and isolated fractions.
A Novel Antinociceptive Sulphated Polysaccharide of the Brown Marine Alga Spatoglossum Schroederi
Authors: Farias Wladimir R. L. , Lima Paula Cristina W. C. , Rodrigues Natália Velloso F. C. , Siqueira Rômmulo Celly L. , Amorim Renata M. F. , Pereira Maria G. , Assreuy Ana Maria S.
Published: March 2019

Sulfated polysaccharides (SP) of brown algae (Phaeophyta) are composed mainly of α- L-fucose, being classified as fucans, with recognized role in inflammation but not in nociception, which was already described for SP obtained from red algae. Here the SP of the brown marine alga S. schroederi (named Ss-SP) was isolated and assayed for the antinociceptive effect. Ss-SP was isolated by DEAE-cellulose, analyzed by agarose gel electrophoresis and evaluated in nociception models (Formalin, Hot plate, Von Frey) using Swiss mice (20-25g). Anion exchange chromatography provided four major fractions being F1 (Ss-SP) that of highest metachromatic activity and sugar content. Ss-SP inhibited both phases of the formalin test. In the first phase the paw licking (55.2±8.07s) was reduced by 45% (30.5±6.51s) and 40% (32.85±8.66s) at 0.1 and 1 μg/kg, respectively. In the second phase, Ss-SP was also inhibitory about 39%, but only at 1 mg/kg (83.0±15.70s) compared to formalin (136.8±10.27s). This inhibitory effect suggests a mixed mechanism similar to morphine, which was not confirmed in the hot plate test, a model of pain associated with central neurotransmission. However, Ss-SP reduced the animal reaction in response to stimulation withVon Frey filament at the 2nd and 3rd h (20.8±6.86% versus carrageenan: 47.9±5.83%; 33.3±7.71% versus carrageenan: 62.5±9.83%). Accordingly, the paw edema induced by carrageenan (0.08±0.01g) was potently reduced in 45.35% by Ss-SP pre-treatment (0.02±0.003g), corroborating the anti-inflammatory activity demonstrated for brown seaweed polysaccharides. In conclusion our data revealed for the first time the antinociceptive effect of Ss-SP which could be used as a new source of analgesic substances.
Hypotensive Effects of the Crotalus Durissus Cascavella Venom: Involvement of NO
Authors: Evangelista Janaina S. A. M , Evangelista João J. F. , Evangelista Inez L. , Nojosa Diva M. B. , Nascimento Nilberto R. F. , Souza Marcellus H.L.P. , Alves Renata S , Martins Alice M C , Moraes Maria Elisabete A. , Monteiro Helena S. A.
Published: March 2019

Crotalus durissus cascavella is a snake native of northeastern Brazil. The aim of the study was to investigate the effects of C. d. cascavella venom on rat mean arterial pressure and vascular reactivity in the mesenteric vascular bed. The venom evoked a dose-dependent decrease in mean arterial pressure, cardiac and respiratory frequency with increased plasma nitrite levels. L-NAME (10 mg/kg) blunted both the hypotension and increased nitrite production observed after the venom administration. To investigate the effects of C. d. cascavella in resistance vessels, the vascular mesenteric bed was studied, and the results suggested that the hypotensive effect of the venom is not dependent on a direct vasodilatory activity. In conclusion, C. d. cascavella venom presented indirect hypotensive effects with the involvement of nitric oxide.
Citrus Essential Oil of Nigeria Part V: Volatile Constituents of Sweet Orange Leaf Oil (Citrus sinensis)
Authors: Kasali Adeleke A. , Lawal Oladipupo A. , Eshilokun Adeolu O. , Olaniyan Abayomi A. , Opoku Andy R. , Setzer William N.
Published: March 2019

The volatile oils extracted from leaves of eight cultivars of Citrus sinensis (L) Osbeck were comprehensively analysed by a combination of GC and GC-MS. Fifty four constituents accounting for 82.3-98.2% were identified. Sabinene (20.9-49.1%), δ-3-carene (0.3-14.3%), ( E)-β-ocimene (4.4-12.6%), linalool (3.7-11.1%) and terpinen-4-ol (1.7-12.5%) were the major constituents that are common to all the volatile oils. In addition, a cluster analysis was carried out and indicated at least four different chemotypes for the C. sinensis cultivars.
A Myristicin-rich Essential Oil from Daucus Sahariensis Growing in Algeria
Authors: Smaili Tahar , Zellagui Amar , Cioni Pier Luigi , Flamini Guido
Published: March 2019

The essential oils obtained by hydrodistillation from leaves and fruits of Daucus sahariensis Murb. were analyzed by GC/MS. The main constituents of the essential oil from the leaves were myristicin (34.3%), α-pinene (5.4%), cis-chrysanthenyl acetate (5.3%) and epi-α-bisabolol (4.8%), and those from the fruits myristicin (43.9%), α-pinene (13.1%), limonene (9.4%), and cis-chrysanthenyl acetate (7.4%). Myristicin, the main constituent of both essential oils, is generally absent in the oils from other Daucus species, permitting the hypothesis that this compound is a chemical marker of this Saharan species.
Activity of Schinus Areira (Anacardiaceae) Essential Oils against the Grain Storage Pest Tribolium castaneum
Authors: Descamps Lilian R. , Chopa Carolina Sánchez , Ferrero Adriana A.
Published: March 2019

Essential oils extracted from leaves and fruits of Schinus areira (Anacardiaceae) were tested for their repellent, toxic and feeding deterrent properties against Tribolium castaneum (Coleoptera: Tenebrionidae) larvae and adults. A topical application assay was employed for the contact toxicity study and filter paper impregnation for the fumigant assay. A treated diet was also used to evaluate the repellent activity and a flour disk bioassay for the feeding deterrent action and nutritional index alteration. The essential oil of the leaves contained mainly monoterpenoids, with α-phellandrene, 3-carene and camphene predominant, whereas that from the fruits contained mainly α-phellandrene, 3-carene and β-myrcene. The leaf essential oil showed repellent effects, whereas that from the fruit was an attractant. Both oils produced mortality against larvae in topical and fumigant bioassays, but fumigant toxicity was not found against adults. Moreover, both essential oils produced some alterations in nutritional index. These results show that the essential oils from S. areira could be applicable to the management of populations of Tribolium castaneum.
Composition, Antioxidant and Antimicrobial Activities of Leaf and Twig Essential Oils of Litsea Akoensis from Taiwan
Authors: Ho Chen-Lung , Lin Chai-Yi , Wang Eugene I-Chen , Su Yu-Chang
Published: March 2019

This study analyzed the hydrodistilled essential oils in the leaves and twigs of Litsea akoensis to determine composition and yield. Seventy-one and 40 compounds were identified in the leaf and twig oils, respectively. The main components of leaf oil were limonene (18.5%), thymol (10.1%), p-cymene (9.6%), β-caryophyllene (8.9%), and carvacrol (8.2%). The main components of twig oil were β-phellandrene (43.7%) and trans-β-ocimene (10.4%). The results demonstrated that leaf oil had excellent antioxidant and antimicrobial activities, superior to those of twig oil.
On the Isomerization of ent-Kaurenic Acid
Authors: Rojas Julio , Aparicio Rosa , Villasmil Thayded , Peña Alexis , Usubillaga Alfredo
Published: March 2019

Kaurenic acid (1a) is a tetracyclic diterpene that has an exocyclic double bond at Δ16. Isokaurenic acid (2a) has an endocyclic Δ15double bond. This compound has been isolated from Espeletia tenore (Espeletinae), a resinous plant from the Venezuelan Andes, but its occurrence is rare. In order to obtain a larger amount of 2a, the isomerization of 1a, which is easily obtained from other Espeletinae, was tried. Kaurenic acid methyl ester (1b) was treated with dil. HCl in CH3Cl/EtOH, after 6 h under reflux a yield of 41.5% isokaurenic acid methyl ester (2b) was obtained but 35.7% 16α-ethoxy-kauran-19-oic acid methyl ester (3b) had formed as a byproduct. Treating 1b with CF3COOH in refluxing CH2Cl2 permitted to obtain a yield of 66.6 % of 2b in 4 h and only traces of 16α-hydroxy-kauran-19-oic acid methyl ester (3a) as a byproduct. Both isomers were separated on a silica gel column impregnated with 20% AgNO3. Treating 2b with KOH in refluxing DMSO yielded pure isokaurenic acid, no back isomerization was observed.
Phenolic Derivatives from the Leaves of Martinella Obovata (Bignoniaceae)
Authors: Arevalo Carolina , Ruiz Ines , Piccinelli Anna Lisa , Campone Luca , Rastrelli Luca
Published: March 2019

A new phenolic derivative, 4-methoxyphenol 1- O-β-D-apiofuranosyl-(1→6)- O-β-D-glucopyranoside (1), has been identified together with uncommon 3,4-dimethoxyphenol 1- O-β-D-apiofuranosyl-(1→6)- O-β-D-glucopyranoside (2) and 3-hydroxy, 4-methoxyphenol 1- O-β-D-apiofuranosyl-(1→6)- O-β-D-glucopyranoside (3) from the leaves of Martinella obovata (Kunth) Bureau & K. Schum., an Honduran species used in folk medicine for the treatment of eyes diseases. Verbascoside, isoverbascoside, leucoceptoside A, vitexin, isovitexin, luteolin 8-C-β-D-glucopiranoside and spireoside were also found. All structures were elucidated on the basis of mass spectrometry and 2D NMR techniques.
Antioxidant Capacity and Phenolic Content of four Myrtaceae Plants of the South of Brazil
Authors: Salvador Marcos José , de Lourenço Caroline C. , Andreazza Nathalia Luiza , Pascoal Aislan C.R.F. , Stefanello Maria Élida Alves
Published: March 2019

Antioxidant compounds can be useful to prevent several degenerative diseases or as preservative in food and toiletries. Species of the Myrtaceae family are able to accumulate phenolic substances and those are closely related to the antioxidant activity due to their capacity to scavenge free radicals, protect against lipid peroxidation and quench reactive oxygen species. These facts prompted us to investigate the antioxidant capacity of the ethanolic extracts of the leaves of four Myrtaceae plants collected of the south of Brazil: Eugenia chlorophylla O. Berg., Eugenia pyriformis Cambess, Myrcia laruotteana Cambess and Myrcia obtecta (Berg) Kiacrsk. The antioxidant potential was performed using the DPPH (a single electron transfer reaction based assay) and ORAC (Oxygen Radical Absorbance Capacity, a hydrogen atom transfer reaction based assay) assays. Moreover, the total soluble phenolic content was also measured using the Folin-Ciocalteu reagent. A preliminary evaluation of the ethanolic extracts of these Myrtaceae plants revealed high levels of phenolic compounds (343.7-429.3 mg GAE) as well as high antioxidant activity according to both methods (1338 a 3785 μmol of TE/g of extract in ORAC and SC50 in the range of 1.70 and 33.7 μg/mL in the DPPH). The highest antioxidant activity obtained by DPPH assay was exhibited by ethanol extract of the leaves of E. pyriformis (1.70 μg/mL), followed by extracts of M. laruotteana (3.38 μg/mL) and M. obtecta (6.66 μg/mL). In comparison with controls, in the DPPH assay, the extract of E. pyriformis was more active than trolox (SC50 = 2.55 μg/mL), while the extracts of M. laruotteana and M. obtecta were more actives than quercetin (SC50 = 7.80 μg/mL). In the ORAC assay, all species also show good antioxidant capacity (>1000 μmol of TE/g). Initial HPLC-UV/DAD and ESIMS confirmed the presence of phenolic acids constituents in the ethanol extracts. The results indicate the presence of compounds possessing promising antioxidant/free-radical scavenging activity in the analyzed extracts of Myrcia and Eugenia plants of the south of Brazil.
Cytotoxicity of Active Ingredients Extracted from Plants of the Brazilian “Cerrado”
Authors: Soares Veronica CG , Bonacorsi Cibele , Andrela Alana LB , Bortoloti Lígia V , de Campos Stepheny C , Fagundes Fábio HR , Piovani Márcio , Cotrim Camila A , Vilegas Wagner , Toyama Marcos H
Published: March 2019

Cytotoxicity assays are needed for the screening of natural products with potential anti-inflammatory. The purpose of this study was to compare the basal cytotoxicity of active ingredients extracted from plants of the Brazilian “cerrado”. The viability was assayed with the neutral red uptake assay in Mac Coy cells after 24h of exposition. The dose evaluated was 50 μg/μL. The test substances were: cinnamic acid, p-coumaric acid, chlorogenic acid, syringic acid, vannilic acid, homogentisic acid, scandenin, palustric acid, diosgenin, cabraleone. Studies of cytotoxicity demonstrated that all active compounds evaluated have low toxicity in vitro. The substances showed cell viability above 60% for the concentration used. However, the cinnamic acid, sacandenin and palustric acid showed highest toxicity with a 50% reduction in cell viability for the dose of 50 μg/μL. Cytotoxic screening results are useful to estimate the best concentrations of those compounds with potential anti-inflammatory without their cause cell death.
Genotoxic Evaluation of a Methanolic Extract of Verbascum Thapsus using Micronucleus Test in Mouse Bone Marrow
Authors: Escobar Franco Matías , Sabini María Carola , Zanon Silvia Matilde , Cariddi Laura Noelia , Tonn Carlos Eugenio , Sabini Liliana Inés
Published: March 2019

Verbascum thapsus L. is a medicinal plant and has been used to treat numerous pulmonary diseases, asthma, inflammatory disease, spasmodic coughs and migraine headaches. Several studies have demonstrated that different extracts of V. thapsus present antimicrobial activity. Thus, the goal of this study was to evaluate the genotoxic and cytotoxic activities of a methanolic extract of Verbascum thapsus, using micronucleus test in mouse bone marrow. No toxicity in bone marrow was detected in the extract-treated groups. The methanolic extract of V. thapsus at doses of 100, 300 and 500 mg / kg, did not produce a significant increase in the frequency of MNPCE in bone marrow and neither altered the relationship PCE / NCE respect to negative control. These cytogenotoxic findings contribute the preclinical knowledge of methanolic extract of V. thapsus and provide security in its use as herbal medicine.
Study of Antiviral and Virucidal Activities of Aqueous Extract of Baccharis Articulata against Herpes suis virus
Authors: Torres Cristina Vanesa , Domínguez María Julia , Carbonari José Luis , Sabini María Carola , Sabini Liliana Inés , Zanon Silvia Matilde
Published: March 2019

Baccharis articulata is native of América and traditionally used for the treatment of digestive disorders and urinary infections. Cytotoxicity of aqueous extracts of B. articulata was investigated in Vero cells. As the maximal non cytotoxic concentration has been established, this concentration has been used to evaluate antiviral and virucidal activities against Herpes suis virus type 1, member of the same subfamily of Herpes simplex virus. Aqueous extracts of B. articulata exhibited more than 95% of virucidal activity. These findings support their potential application as a disinfectant or antiseptic with low toxicity and provide a valuable knowledge to ethnopharmacology properties of Baccharis articulata.
Evaluation of Cytogenotoxic Effects of Cold Aqueous Extract from Achyrocline Satureioides by Allium cepa L test
Authors: Sabini María C. , Cariddi Laura N. , Escobar Franco M. , Bachetti Romina A. , Sutil Sonia B. , Contigiani Marta S. , Zanon Silvia M. , Sabini Liliana I.
Published: March 2019

Achyrocline satureioides (“marcela del campo”) is native to America. Numerous investigations have reported several bioactive properties such as anti-inflammatory, hepatoprotective, immunomodulatory, antimicrobial and antiviral. Nowadays, few medicinal plants have been scientifically evaluated to test its safety, efficacy and potential benefits, despite the great public interest in these herbs. The aim of this work was to evaluate the cytotoxic and genotoxic activities of cold aqueous extract obtained from A. satureioides using Allium cepa L test. The results demonstrated the absence of genotoxicity of the extract. Only higher concentrations induced cytotoxicity but interestingly this effect was reversible and was not associated with mutagenicity. The contribution of this research provides assurance of safety in the application of Achyrocline satureioides in treatment of microbial diseases and other pathologies helping to define selective toxicity.