bluuebunny/crossref_metadata_2025 huggingface dataset:
EAG Responses Increase of Spodoptera littoralis Antennae after a Single Pheromone Pulse
Authors: Quero Carmen , Vidal Berta , Guerrero Angel
Published: March 2019

Increased behavioral sensitivity to the pheromone after brief exposure of the whole insect to the sex pheromone has been documented in antennal lobe neurons of Spodoptera littoralis. We investigated whether a brief stimulus of the major component of the pheromone on naïve antenna separated from the head increased the electroantennographic responses after successive stimulations at different times. The response increase was clear 30 min after the first stimulation, and this effect lasted at least 60 min, the average life time of the antenna. Our results suggest that the olfactory receptor neurons, and not only the neurons in the antennal lobe, may be involved in the increased antennal response after a single pheromone pulse.
Valorization of Essential Oils from Moroccan Aromatic Plants
Authors: Santana Omar , Andrés María Fe , Sanz Jesús , Errahmani Naima , Abdeslam Lamiri , González-Coloma Azucena
Published: March 2019

The chemical composition and biological activity of cultivated and wild medicinal and aromatic plants from Morocco ( Artemisia herba-alba, Lippia citriodora, Mentha pulegium, M. spicata, Myrtus communis, Rosmarinus officinalis, and Thymus satureioides) are described. The essential oils (EOs) of these species have been analyzed by GC-MS. The antifeedant, nematicidal and phytotoxic activities of the EOs were tested on insect pests ( Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi), root-knot nematodes ( Meloydogine javanica) and plants ( Lactuca sativa, Lolium perenne and Lycopersicum esculentum). EOs from A. herba-alba, M. pulegium and R. officinalis were strong antifeedants against S. littoralis, M. persicae and R. padi. EOs from L. citriodora, M. spicata and T. satureioides showed high nematicidal activity. These biological effects are explained by the activity of the major EO components and/or synergistic effects.
New Pseudoguaiane Derivatives from Inula aschersoniana Janka var. aschersoniana
Authors: Trendafilova Antoaneta , Todorova Milka , Genova Viktoriya , Shestakova Pavletta , Dimitrov Dimitar , Jadranin Milka , Milosavljevic Slobodan
Published: March 2019

The aerial parts of Inula aschersoniana Janka var. aschersoniana afforded parthenolide, diepoxycostunolide, inusoniolide, chrysosplenol C and four new pseudoguaiane-type sesquiterpenoids. Their structures were determined using spectral methods and relative stereochemistry by NOESY correlations.
Chemical Composition of Bioactive Alkaloid Extracts from Some Narcissus Species and Varieties and their Biological Activity
Authors: Havlasová Jana , Šafratová Marcela , Siatka Tomáš , Štěpánková Šárka , Novák Zdeněk , Ločárek Miroslav , Opletal Lubomír , Hrabinová Martina , Jun Daniel , Benešová Nina , Kuneš Jiří , Cahlíková Lucie
Published: March 2019

Alkaloid extracts of eight Narcissus (Amaryllidaceae) species and varieties were studied with respect to their acetylcholinesterase (HuAChE) and butyrylcholinesterase (HuBuChE) inhibitory activity and alkaloid patterns. Thirty alkaloids were determined by GC/MS, and twenty-five of them identified from their mass spectra, retention times and retention indexes. Promising HuAChE inhibition activity was demonstrated by six Narcissus taxa and HuBuChE inhibition by N. jonquila cv. Double Campernelle and N. nanus cv. Elka with IC50 values of 24.1 ± 1.9 μg/mL and 25.1 ± 1.8 μg/mL, respectively. Two alkaloids were isolated in pure form using preparative TLC and identified as the galanthamine type alkaloid narwedine and the lycorine type alkaloid incartine. Both compounds were tested for their biological activity. They were considered inactive in HuAChE/HuBuChE assays, but showed promising prolyl oligopeptidase inhibition activities with IC50 values of 0.95 ± 0.12 mM and 0.91 ± 0.09 mM, respectively.
New Phenylpropanoid-Substituted Flavan-3-ols from Pu-er Ripe Tea
Authors: Tao Mu-Ke , Xu Min , Zhu Hong-Tao , Cheng Rong-Rong , Wang Dong , Yang Chong-Ren , Zhang Ying-Jun
Published: March 2019

Pu-er ripe tea is a special microbial post-fermented tea made from Pu-er raw tea, a kind of green tea produced from the leaves of Camellia sinensis var. assamica. It is one of the most consumed teas in the past two decades in China, due to its special flavor, taste, and beneficial effects. This work aimed to obtain diverse catechin structures from Pu-er ripe tea, which led to the isolation of four new phenylpropanoid-substituted flavan-3-ols, puerins C-F (1-4), together with four known flavan-3-ols, (+)-catechin (5), (-)-epicatechin (6), (±)-gallocatechin (7), and (-)-epigallocatechin (8). Their structures were elucidated on the basis of detailed spectroscopic analysis, including 1D and 2D NMR, mass and CD spectra. Compounds 1-4, which could be formed in the post-fermentative process of Pu-er tea, were isolated for the first time from tea and Theaceae plant.
Chemical Analysis of Volatile Oils from West Himalayan Pindrow Fir Abies pindrow
Authors: Padalia Rajendra C. , Verma Ram S. , Chauhan Amit , Goswami Prakash , Chanotiya Chandan S.
Published: March 2019

The essential oil composition of needle and stem oils of Abies pindrow (Royle ex D.Don) Royle, commonly known as Pindrow or West Himalayan Fir, were analyzed by gas chromatography with flame ionization detection (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Fifty-six constituents, accounting for 96.0% of needle and 83.5% of stem oil composition, were identified. The oils were characterized by a high content of monoterpenoids (68.9%–79.9%), mainly comprised by limonene (21.0%–34.4%), camphene (0.5%–19.9%), α-pinene (13.8%–16.8%), myrcene (6.7%–8.3%) and β-pinene (6.5%–8.6%). Monoterpene hydrocarbons were predominant in both oils, but the quantitative and qualitative composition of the volatile constituents was specific for each part of the tree; and considerable variations in their terpenoid production pattern were also noticed. Results were compared with earlier reported fir species from different geographic regions.
Cytotoxicity Studies of Lycorine Alkaloids of the Amaryllidaceae
Authors: Nair Jerald J. , van Staden Johannes
Published: March 2019

The plant family Amaryllidaceae is renowned for its unique alkaloid constituents which possess a significant array of structural diversity. Several of these alkaloids are known for their interesting biological properties, of which galanthamine and pancratistatin have acquired a privileged status due to their relevance in the pharmaceutical arena. In particular, galanthamine represents the first prescription drug emanating from the Amaryllidaceae after its approval by the FDA in 2001 for the treatment of Alzheimer's disease. Following on this commercial success there have been sustained projections for the emergence of an anticancer agent related to pancratistatin due to the potency, selectivity, low toxicity and high tolerability typifying targets of this series of alkaloids. The lycorine series of alkaloids have also garnered widespread interest as cytotoxic agents and were amongst the earliest of the Amaryllidaceae constituents to exhibit such activity. To date over 100 of such naturally-occurring or synthetically-derived alkaloids have been screened for cytotoxic effects against a number of cancer cell lines. This survey examines the cytotoxic properties of lycorine alkaloids, highlights the outcomes of structure-activity relationship orientated studies and affords plausible insights to the mechanistic rationale behind these effects.
Acemannan, an Extracted Polysaccharide from Aloe vera: A Literature Review
Authors: Sierra-García Gerardo Daniel , Castro-Ríos Rocío , González-Horta Azucena , Lara-Arias Jorge , Chávez-Montes Abelardo
Published: March 2019

In this review, the composition, actions, and clinical applications of acemannan in medicine and its effectiveness as an adjunct in the treatment of diseases are presented. An electronic literature search was performed up to January 2014 for studies and research presenting data to validate the efficacy of acemannan. A total of 50 titles, abstracts and full-text studies were selected and reviewed. Acemannan has various medicinal properties like osteogenic, anti-inflammatory, and antibacterial, which accelerate healing of lesions. Also, acemannan is known to have antiviral and antitumor activities in vivo through activation of immune responses. It was concluded that Aloe vera has immense potential as a therapeutic agent. Even though the plant is a promising herb with various clinical applications in medicine and dentistry, more clinical research needs to be undertaken to validate and explain the action of acemannan in healing, so that it can be established in the field of medicine and a more precise understanding of the biological activities of these is required to develop Aloe vera as a pharmaceutical source.
Trichostemonoate, a New Anticancer Tirucallane from the Stem Bark of Walsura trichostemon
Authors: Phontree Kiettipum , Sichaem Jirapast , Khumkratok Suttira , Siripong Pongpun , Tip-pyang Santi
Published: March 2019

Trichostemonoate (1), a new tirucallane, together with four known compounds, 11α,20-dihydroxydammar-24-ene-3-one (2), sapelin E acetate (3), grandifolinolenenone (4) and α-mangostin (5), were isolated from the stem bark of Walsura trichostemon. The structural assignment of the new compound was based on spectroscopic methods. All isolated compounds were evaluated for their cytotoxicity against five cancer cell lines.
A New Cycloartane Glucoside from Rhizophora stylosa
Authors: Huong Phan Thi Thanh , Diep Chau Ngoc , Van Thanh Nguyen , Tu Vu Anh , Hanh Tran Hong , Cuong Nguyen The , Thao Nguyen Phuong , Cuong Nguyen Xuan , Thao Do Thi , Thai Tran Huy , Nam Nguyen Hoai , Ban Ninh Khac , Van Kiem Phan , Van Minh Chau
Published: March 2019

Nine secondary metabolites, including a new cycloartane glucoside, rhizostyloside (1), were isolated from a methanol extract of Rhizophora stylosa leaves through several chromatographic experiments. The structures of the compounds were determined on the basis of NMR spectroscopic (1H and 13C NMR, HSQC, HMBC, 1H-1H COSY, NOESY) and HR-ESI-MS data and by comparison with literature values. Compound 1 exhibited significant cytotoxicity against three human cancer cell lines: KB (epidermoid carcinoma), LU-1 (lung adenocarcinoma), and SK-Mel-2 (melanoma). In addition, 1 strongly activated caspase-3/7 in LU-1 cells.
Kolgaosides A and B, Two New Triterpene Glycosides from the Arctic Deep Water Sea Cucumber Kolga hyalina (Elasipodida: Elpidiidae)
Authors: Silchenko Alexandra S. , Kalinovsky Anatoly I. , Avilov Sergey A. , Andryjashchenko Pelageya V. , Fedorov Sergey N. , Dmitrenok Pavel S. , Yurchenko Ekaterina A. , Kalinin Vladimir I. , Rogacheva Antonina V. , Gebruk Andrey V.
Published: March 2019

Two novel triterpene holostane nonsulfated pentaosides, kolgaosides A (1) and B (2), and one known, holothurinoside B (3), were isolated from the Arctic sea cucumber Kolga hyalina, the second representative of the family Elpidiidae, order Elasipodida, from which triterpene glycosides have been obtained. The structures of 1 and 2 were elucidated using 1H and 13C NMR and 2D NMR procedures (HSQC, HMBC, COSY, ROESY, TOCSY) and HRESI mass-spectrometry. Kolgaosides A (1) and B (2) demonstrate low cytotoxic activity against the cells of the ascite form of mouse Ehrlich carcinoma and moderate hemolytic activity against mouse erythrocytes, despite the presence of hydroxy groups in the side chains of the aglycones. The glycosides of K. hyalina are similar to those of the Antarctic sea cucumber Rhipidothuria racowitzai Hèrouard, 1901 (= Achlionice violaescupidata) (Elasipodida: Elpidiidae); this may have chemotaxonomic significance.
Acaricidal Activity against Panonychus citri and Active Ingredient of the Mangrove Plant Cerbera manghas
Authors: Deng Yecheng , Liao Yongmei , Li Jingjing , Yang Linlin , Zhong Hui , Zhou Qiuyan , Qing Zhen
Published: March 2019

Cerbera manghas is a mangrove plant which possesses comprehensive biological activities. A great deal of research has been undertaken on the chemical constituents and medical functions of C. manghas; insecticidal and antifungal activities have also been reported, but the acaricidal activity has not been studied. In our study, the acaricidal activity and active substances of C. manghas were investigated using a spray method, which showed that the methanol extracts of the fruit, twigs and leaves exhibited contact activity against female adults of Panonychus citri, with LC50 values at 24 h of 3.39 g L−1, 4.09 g L−1 and 4.11 g L−1, respectively. An acaricidal compound was isolated from C. manghas by an activity-guided isolation method, and identified as (-)-17β-neriifolin, which is a cardiac glycoside. (-)-17β-Neriifolin revealed high contact activity against female adults, nymphae, larvae and eggs of P. citri, with LC50 values at 24 h of 0.28 g L−1, 0.29 g L−1, 0.28 g L−1 and 1.45 g L−1, respectively.
Unusual 2(1H)-Pyrazinones Isolated from a Culture of a Brazilian Marine-Derived Streptomyces sp
Authors: Thomasi Sérgio S. , Granato Ana C. , Romano Luis H. , Dhooghe Liene , do Nascimento Eduardo S. P. , Badino Alberto C. , da Silva Maria F. G. F. , Ferreira Antonio G. , Venâncio Tiago
Published: March 2019

Four new secondary metabolites, giovaninones A-D (1–4), were isolated from an ethyl acetate extract of a culture of a marine-derived Streptomyces strain designated SS99BA-2. Chemical analysis was completely conducted in a coupled automated LC-SPE system with the use of a cryogenic NMR probehead and HRMS. The application of this system to identify, purify and elucidate all the structures is described.
New Mechanism of Magnolol and Honokiol from Magnolia officinalis against Staphylococcus aureus
Authors: Liu Tao , Pan Yalin , Lai Renfu
Published: March 2019

Cell division protein, FtsZ, has been identified as a new potential antimicrobial target against multidrug-resistant (MDR) and methicillin-resistant Staphylococcus aureus (MRSA). By using computer-aided simulation, the phenolic compounds magnolol and honokiol from Magnolia officinalis were shown to have high anchor energies to FtsZ of S.aureus. The calculated binding energies of magnolol and honokiol for this FtsZ (PDB Code: 4DXD) were established to be −7.6 kcal/mol and −8.2 kcal/mol, respectively. Both of them showed polymerization inhibition efficacy for this FtsZ at 100 ppm, which confirmed the simulation results. Their antibacterial activity against S. aureus including multidrug-resistant (MDR) and methicillin-resistant S.aureus (MRSA) with minimum inhibitory concentration (MIC) values in the range of 8–16 ppm. These findings support the use of computer-aided simulation to screen natural compounds for this cell division protein, FtsZ, and this method can be a quick and promising approach for the development of antimicrobial agents against multi-drug resistant S. aureus.
Molecular Cloning and Characterization of Tyrosine Aminotransferase and Hydroxyphenylpyruvate Reductase, and Rosmarinic Acid Accumulation in Scutellaria baicalensis
Authors: Kim Yeon Bok , Uddin Md Romij , Kim YeJi , Park Chun Geon , Park Sang Un
Published: March 2019

Rosmarinic acid (α- O-caffeoyl-3,4-dihydroxyphenylacetic acid, RA) is a caffeoyl ester widely distributed in plants. cDNA clones encoding tyrosine aminotransferase (TAT1 and 2) and hydroxyphenylpyruvate reductase (HPPR) have been isolated from Scutellaria baicalensis. The open reading frames (ORFs) of SbTAT1 and 2 were 1230 and 1272 bp long and encoded 409 and 423 amino acid residues, respectively. HPPR corresponded to a 942-bp ORF and 313 amino acid residues of translated protein. To study the molecular mechanisms of TAT and HPPR and investigate RA accumulation in S. baicalensis, we examined the transcript levels of TAT isoforms and HPPR with quantitative real-time PCR and analyzed the RA content in different organs by using high-performance liquid chromatography. The transcript levels of SbTAT1 SbTAT2, and SbHPPR in the flowers were higher than those in other organs. RA was also highly accumulated in the flowers and with a trace amount in the roots. No RA was detected in the leaves and stems of S. baicalensis. The amount of accumulated RA in the flowers was 28.7 times higher than that in the roots. Our results will be helpful in elucidating the mechanisms of RA biosynthesis in S. baicalensis.
Synthesis and Characterization of 4-Aryl-4H-chromenes from H-Cardanol
Authors: Rao Hulluru Surya Prakash , Kamalraj Mani
Published: March 2019

We have synthesized and characterized a variety of fat-soluble, low-melting and medicinally useful 4-aryl-4 H-chromenes from H-cardanol (side-chain perhydrogenated cardanol, 3-pentadecylphenol), a renewable and low-cost product from locally grown cashew nut trees ( Anacardium occidentale L.). We incorporated H-cardanol into the aromatic rings of either 4 H-chromene or phenol, or both. Substitution of C4SMe in N-methyl-4-(methylthio)-3-nitro-4 H-chromene-2-amines with H-cardanol was regio-specific at the C6 position.
Quantitative Analysis Coupled with Toxic Evaluation to Investigate the Influence of Sulfur-Fumigation on the Quality of Chrysanthemum morifolium
Authors: Ding Ke , Cao Gang , Xu Zhiwei , Chen Xiaocheng
Published: March 2019

In the present study, quantitative analysis coupled with toxic evaluation was applied to investigate the influence of sulfur-fumigation on the quality of Chrysanthemum morifolium. The results showed that the average contents of six flavonoids (cynaroside, hyperoside, isoquercitrin, luteolin, apigenin, and diosmetin) in sulfur-fumigated C. morifolium samples decreased by about 6.2%, 3.5%, 22.0%, 33.3%, 26.0%, and 36.9%, respectively, while the average contents of two organic acids (chlorogenic acid and isochlorogenic acid A) in sulfur-fumigated C. morifolium samples increased by about 16.8% and 7.6%, respectively. Furthermore, high dosage sulfur-fumigated C. morifolium could induce hydropic degeneration in epithelial cells of the renal tubule and interstitial edema. This indicates that sulfur-fumigated C. morifolium may lead to renal toxicity.
Cell Cycle Control by Natural Phenols in Cisplatin-Resistant Cell Lines
Authors: Catanzaro Daniela , Vianello Caterina , Ragazzi Eugenio , Caparrotta Laura , Montopoli Monica
Published: March 2019

Fifteen plant polyphenols, including flavonoids, cinnamic acids, coumarins and capsaicin, were investigated for their capacity to suppress cell growth and regulate the cell cycle of in vitro human ovarian carcinoma (2008 cell line) and cervix squamous carcinoma cells (A431), and their cisplatin (CDDP)-resistant subclones (C13 and A431Pt, respectively). Evaluation of the cytotoxic effects of the polyphenols (0.01–100 μM) indicated that especially rhein and quercetin were almost equiactive in wild type and CDDP-resistant cells, indicating lack of cross-resistance with cisplatin. Capsaicin was more potent in CDDP-resistant subclones than in wild type cells. The order of their potencies is flavonoids > anthraquinones > vanilloids > coumarins > phenols, cinnamic acids. The natural phenols which were most cytotoxic (rhein, quercetin and capsaicin) were able to cause the arrest of the cancer cell cycle, suggesting that specific cell cycle regulatory proteins are possibly involved in their intracellular mechanism of action. In particular, the natural compounds were revealed to be more active in CDDP-resistant cells than in wild types, especially inducing apoptotic death.
Chemical Composition and Insecticidal Properties of Essential Oils of Piper septuplinervium and P. subtomentosum (Piperaceae)
Authors: Murillo Mónica Constanza Ávila , Suarez Luis Enrique Cuca , Salamanca Jairo Alonso Cerón
Published: March 2019

Essential oils of Piper subtomentosum (leaves and inflorescences) and Piper septuplinervium (aerial parts) were analyzed by GC-MS; sixty-three compounds were determined, representing 92.0%, 86.9 %, and 91.8 % of the total relative oil composition of the leaves, inflorescences, and aerial parts, respectively. The most abundant component in the aerial parts and inflorescence oils was α-pinene (27.3%, 21.0%, respectively), and δ-cadinene was the main component of the leaf oil. Insecticidal activity of the essential oils were determined on the Spodoptera frugiperda second instar larvae; the essential oil from the aerial parts of P. septuplinervium was the most active against insect pests (LC50= 9.4 μL/L of air). Statistical analysis by direct Pearson correlation showed that the insecticidal activity of the essential oils was primarily due to camphene and α- and β-pinene. The effect of the oils on the insect life cycle was also evaluated, and in some cases, a delay in growth and inhibition of the oviposition in the females were observed.
A New Sesquiterpene Lactone and Other Constituents of Moquiniastrum polymorphum subsp. floccosum (Asteraceae)
Authors: Strapasson Regiane L. B. , Rüdiger André Luis , Burrow Robert A. , Barison Andersson , Stefanello Maria Έlida A.
Published: March 2019

A new guaianolide, 1 S, 3 S, 5 R, 6 S, 7 S, 11 R-1-hydroxy-11α,13-dihydrozaluzanin C (1), was isolated from Moquiniastrum polymorphum subsp. floccosum trunk bark, together with fifteen known compounds, which were identified as 11α,13-dihydroglucozaluzanin C (2), 8α-hydroxy-11α,13-dihydrozaluzanin C (3), zaluzanin C (4), gochnatiolide B (5), ethyl caffeate (6), methyl chlorogenate (7), ethyl chlorogenate (8), methyl 3,5-dicaffeoyl quinate (9), ethyl 3,5-dicaffeoyl quinate (10), methyl 4,5-dicaffeoyl quinate (11), ethyl 4,5-dicaffeoyl quinate (12), ethyl 3,4-dicaffeoyl quinate (13), 3,5-dicaffeoyl quinic acid (14), 4,5-dicaffeoyl quinic acid (15), and 3,4-dicaffeoyl quinic acid (16). With the exception of 5, all known compounds are being reported for the first time in M. polymorphum.
Facile, Protection-Free, One-Pot Synthesis of Aureusidin
Authors: Nguyen Quoc Vuong , Lan Phuong Diep Thi , Thi Hang Pham , Vu Van Chien , Le Tuan Nguyen , Chau Van Minh , Pham Van Cuong
Published: March 2019

A new, reliable, and convenient protection-free one-pot method for the synthesis of aureusidin (1) is described. The present synthetic approach involves the condensation of 4,6-dihydroxybenzofuranone with 3,4-dihydroxybenzaldehyde in the presence of concentrated HCl to afford aureusidin (1) in good yield with high purity. This procedure offers a short and simple route for the preparation of aureusidin (1), a bioactive natural product from several vegetal species, as well as for synthesis of other aurones.
Isolation of Hydroxyoctaprenyl-1′,4′-hydroquinone, a new Octaprenylhydroquinone from the Marine Sponge Sarcotragus spinosulus and Evaluation of its Pharmacological Activity on Acetylcholine and Glutamate Release in the Rat Central Nervous System
Authors: Bisio Angela , Fedele Ernesto , Pittaluga Anna , Olivero Guendalina , Grilli Massimo , Chen Jiayang , Mele Giacomo , Malafronte Nicola , Tommasi Nunziatina De , Ledda Fabio , Manconi Renata , Pronzato Roberto , Marchi Mario
Published: March 2019

Three polyprenyl-1′,4′-hydroquinone derivatives, heptaprenyl-1′,4′-hydroquinone (1), octaprenyl-1′,4′-hydroquinone (2), and hydroxyoctaprenyl-1′,4′-hydroquinone (3) were isolated from the marine sponge Sarcotragus spinosulus collected at Baia di Porto Conte, Alghero (Italy). Our findings indicate that the compounds isolated from S. spinosulus can significantly modulate the release of glutamate and acetylcholine in the rat hippocampus and cortex and might, therefore, represent the prototype of a new class of drugs regulating glutamatergic and cholinergic transmission in the mammalian central nervous system.
Constituents of Essential Oils from the Leaf and Flower of Plumeria alba Grown in Nigeria
Authors: Lawal Oladipupo A. , Ogunwande Isiaka A. , Opoku Andy R.
Published: March 2019

This paper reports on the compounds identified in the leaf and flower essential oils obtained by hydrodistillation of Plumeria alba L. (Apocynaceae) grown in Nigeria. The chemical analysis of the essential oils was achieved by means of gas chromatography (GC) and gas chromatography coupled with mass spectrometry (GC-MS). Linalool (13.2%), n-nonanal (9.6%), phenyl acetaldehyde (8.5%), neryl acetone (5.3%) and n-decanal (5.1%) were the main constituents of the leaf oil. On the other hand, the flower oil comprised mainly of limonene (9.1%), linalool (7.9%), α-cedrene (8.0%), caryophyllene oxide (7.9%) and ( E, E)-α-farnesene (6.6%). This is the first report on the essential oil constituents of P. alba.
Activity against Microorganisms Affecting Cellulosic Objects of the Volatile Constituents of Leonotis nepetaefolia from Nicaragua
Authors: Casiglia Simona , Bruno Maurizio , Senatore Felice
Published: March 2019

The chemical composition of the essential oil from aerial parts of L. nepetaefolia (L.) R. Br. collected in Nicaragua was evaluated by GC and GC-MS. The main components were ( Z)-phytol (22.8%), caryophyllene oxide (18.9%) and hexahydrofarnesylacetone (9.0%). The antibacterial activity against several Gram + and Gram - bacteria, including Bacillus cereus and B. subtilis, both infesting historical cellulosic material, was also determined. B. cereus, B. subtilis and Staphylococcus epidermis were the most affected by the action of the oil.
Nortriterpene Saponins from Akebia trifoliata
Authors: Matsuzaki Keiichi , Murano Kayo , Endo Yurika , Kitanaka Susumu
Published: March 2019

Three new nortriterpene saponins, 2α,3β,20α-trihydroxy-30-norolean-12-en-28-oic acid O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (3), 2α,3β,20α-trihydroxy-30-norolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (4), and 2α,3β,23-trihydroxy-30-noroleana-12,19-dien-28-oic acid O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (6), were isolated from the methanol extract of the pericarps of Akebia trifoliata Koidzumi (Lardizabalaceae), together with five known nortriterpene saponins and three phenolic glycosides. Their structures were elucidated by spectroscopic analyses and acid hydrolysis.
New Unusual Alkaloids from the Ascidian Eudistoma vannamei
Authors: Pimenta Antônia Torres Ávila , Jimenez Paula Christine , Costa-Lotufo Letícia Veras , Braz-Filho Raimundo , Lima Mary Anne Sousa
Published: March 2019

The MeOH extract of the ascidian Eudistoma vannamei was found to contain three novel compounds, the adenine alkaloid derivatives 9-[ N-(leucyl)-isoleucyl]-adenine (1) and 8-hydroxy-8-isopentyl-7,8-dihydroadenine (2), and the phenylalanine peptide derivative N-[ N-(leucyl)-isoleucyl]phenethylamine (3). Other previously related compounds isolated from this extract include thymidine, 2′-deoxyuridine and phenylalanine. The structures of the new compounds were elucidated through the use of NMR and mass spectrometry.
Isoprenylated Xanthone and Benzophenone Constituents of the Pericarp of Garcinia planchonii
Authors: Trinh Duong Hoang , Ha Ly Dieu , Tran Phuong Thu , Nguyen Lien-Hoa Dieu
Published: March 2019

A new xanthone, planchoxanthone (1), together with six known compounds, garcinianone A (2), cowanin (3), rubraxanthone (4), β-mangostin (5), dulcisxanthone B (6), and guttiferone Q (7), were isolated from an n-hexane extract of the pericap of Garcinia planchonii. Their structures were elucidated using spectroscopic methods. Antioxidant activity of the isolated compounds was tested using the DPPH free radical scavenging assay.
Stemofurans X-Y from the Roots of Stemona Species from Laos
Authors: Quang Dang Ngoc , Khamko Vong Anatha , Trang Nguyen Thi , Yen Lam Thi Hai , Dien Pham Huu
Published: March 2019

Two new phenylbenzofuran-type stilbenoids named stemofurans X and Y (1, 2) were isolated from the roots of Stemona pierrei and S. tuberosa, respectively, together with ten known compounds. These compounds were stemanthrenes B-C (3, 4), (+)-syringaresinol (5), maistemonine (6), isomaistemonine (7) and sesamin (8) from S. pierrei, and stemophenanthrenes A-C (9–11) and isopinosylvin A (12) from S. tuberosa. Stemofurans X-Y (1, 2) showed moderate cytotoxicity against the four cancer cell lines KB (human epidermal carcinoma), MCF7 (human breast carcinoma), SK-LU-1 (human lung carcinoma), and Hep-G2 (hepatocellular carcinoma).
Development and Validation of a High-Performance Liquid Chromatographic Method for the Simultaneous Quantification of Marker Constituents in Cheonwangbosimdan
Authors: Seo Chang-Seob , Shin Hyeun-Kyoo
Published: March 2019

A high-performance liquid chromatography–photodiode array detector method was established for the simultaneous determination of 7 components in Cheonwangbosimdan extract. The components were 5-hydroxymethyl-2-furaldehyde (1), coptisine (2), berberine (3), nodakenin (4), harpagoside (5), cinnamic acid (6), and β-asarone (7). All analytes were separated by gradient elution using two mobile phases on a Gemini C18 column and maintained at 40°C. The flow rate was 1.0 mL/min and the injection volume was 10 μL. Calibration curves of the 7 compounds showed good linearity with correlation coefficients ( r2) ≥ 0.9996. The limits of detection and quantification of the 7 analytes were 0.01–0.04 and 0.03–0.12 μg/mL, respectively. The recoveries of the 7 marker constituents were 97.6–104.2% with relative standard deviations (RSD) of less than 2.2%. The RSD values of intra- and interday precision were 0.11–1.78 and 0.19–1.92%, respectively. Among the 7 biomarker compounds, the major compounds of Cheonwangbosimdan were berberine and coptisine, which originated from Coptis japonica. The results indicate that the developed analytical method is suitable for quality control use.
Total Synthesis of Hybocarpone, a Cytotoxic Naphthazarin Derivative from the Lichen Lecanora hybocarpa, and Related Compounds
Authors: Dragan Sergey V. , Pushilin Michael A. , Glazunov Valery P. , Denisenko Vladimir A. , Anufriev Victor Ph.
Published: March 2019

The concise synthesis of the lichen-derived antitumor agent hybocarpone (1) and its analogs is described. A new synthetic approach is based on the direct oxidative dimerization of the available naphthazarin precursors in the formation of the binaphtho[2,3- b; 2,3- d]furantetraone structure. It was shown that the first step to tetrahydrofuran features is the bridging hindered S*, S* and R*, S* carbon-carbon bonds of the molecules, setting the relative configurations of the 5a S*,6a S*,12a S*,12b S* and 5a S*,6a R*,12a R*,12b S* diastereomers.
The Anti-Rheumatoid Arthritis Property of the Folk Medicine Dianbaizhu (Gaultheria leucocarpa var. yunnanensis, Ericaceae)
Authors: Xie Meng , Lu Yi , Yan Cheng , Jiang Rui , Liu Weirui , Liu Zizhen , Xu Guanling , Yang Yue , Zhang Xia , Tian Yuxin , Wang Yan , Lu Jianqiu , She Gaimei
Published: March 2019

The Chinese folk medicine Dianbaizhu, consisting of Gaultheria species, is widely used for the treatment of rheumatoid arthritis by several minority nationalities. The species and plant parts of this genus used as Dianbaizhu in clinical application are confused. In order to elucidate the species and the medicinal parts, as well as to ascertain the effective components and the probable optimal source of Dianbaizhu, the different plant parts and polarity fractions of its mainstream species, G. leucocarpa var. yunnanensis were investigated. The inhibition of nitric oxide and tumor necrosis factor produced in macrophage J774 were used to assess the anti-inflammatory effect of those samples. G. leucocarpa var. yunnanensis may be the preferred species for anti-RA effect. The underground parts of this taxon showed the best anti-inflammatory and anti-RA activities; the n-butanol and water fractions of the underground parts may be the most anti-RA active.
A GC-FID Validated Method for the Quality Control of Eucalyptus globulus Raw Material and its Pharmaceutical Products, and GC-MS Fingerprinting of 12 Eucalyptus Species
Authors: Bueno Paula Carolina Pires , Junior Milton Groppo , Bastos Jairo Kenupp
Published: March 2019

In this work we have validated a method to standardize and control the quality of Eucalyptus globulus raw material and phytomedicines containing either the essential oil or the fluid extract of this plant in the final formulation. Internal standardization provided a simple, fast, and reproducible GC-FID analytical method that accurately quantified 1,8-cineol in different E. globulus sub-products, such as its essential oil, dried leaves, fluid extract, and syrup. In addition, GC-MS identification of the main compounds of E. globulus species afforded fingerprints for the qualitative analysis of different Eucalyptus species.
Chemistry and Leishmanicidal Activity of the Essential Oil from Artemisia absinthium from Cuba
Authors: Monzote Lianet , Piñón Abel , Scull Ramón , Setzer William N.
Published: March 2019

Historically, natural products have been a rich source of lead molecules in drug discovery. In particular, products to treat infectious diseases have been developed and several reports about potentialities of essential oils (EO) against Leishmania could be found. In this study, we report the chemical characterization, anti-leishmanial effects and cytotoxicity of the EO from Artemisia absinthium L. Chemical analysis revealed the EO to be composed of 18 compounds, 11 of which were identified, accounting for 64.1% of the composition. The main component of the EO was trans-sabinyl acetate, which made up 36.7%. In vitro anti-leishmanial screening showed that the A. absinthium EO inhibited the growth of promastigotes (14.4 ± 3.6 μg/mL) and amastigotes (13.4 ± 2.4 μg/mL) of L. amazonensis; while cytotoxicity evaluation caused 6 fold higher values than those for the parasites. In a model of experimental cutaneous leishmaniasis in BALB/c mice, five doses of EO at 30 mg/kg by intralesional route demonstrated control of lesion size and parasite burden ( p< 0.05) compared with animals treated with glucantime and untreated mice. In conclusion, in vitro and in vivo results showed the potential of EO from A. absinthium as a promising source for lead or active compounds against Leishmania, which could be explored.
Identification of Sesquiterpene Lactones in the Bryophyta (Mosses) Takakia: Takakia Species are Closely Related Chemically to the Marchantiophyta (Liverworts)
Authors: Asakawa Yoshinori , Nii Kaeko , Higuchi Masanobu
Published: March 2019

Takakia lepidozioides has been considered to be the most primitive liverwort morphologically and classified initially in the Marchantiophyta (liverworts). However, the Takakia have been reclassified from liverworts to mosses on the basis of the similarity of the male sporophyte of T. ceratophylla to that of some mosses. Reinvestigation of secondary metabolites of fresh T. lepidozioides resulted in identification of eudesmane-type sesquiterpene lactones and hydrocarbon that are significant chemical markers of several liverworts. T. lepidozioides also produces a small amount of hop-22(29)-ene, together with coumarin, which produce the characteristic odor of T. lepidozioides, and 1,4-hydroquinone; these are the predominant volatile components, whereas dihydrocoumarin, 1,4-benzoquinone, dihydrobenzofuran, α-asarone and α-tocopherol are minor components. These chemical results indicated that T. lepidozioides is more closely related to the Marchantiophyta than the Bryophyta. T. lepidozioides is morphologically similar to the liverwort Haplomitrium species. However, both species are totally different chemically.
Secondary Metabolites from a Strain of Alternaria tenuissima Isolated from Northern Manitoba Soil
Authors: Anyanwu Chukwudi S. , Sorensen John L.
Published: March 2019

Deoxyphomalone (1), dimethyl 4-methyl-2,6-pyridinedicarboxylate (2), stemphyperylenol (3), and N-methyl-2-pyrrolidone (4) were isolated from the fermentation broth of a strain of the fungus, Alternaria tenuissima. This fungus was isolated from the soil underlying the lichen, Peltigera didactyla, which had been collected from Wapusk National Park in Northern Manitoba. The structures of the compounds were determined by comprehensive analysis of their spectroscopic data including FT-IR, 1D and 2D NMR spectroscopy and mass spectrometry; and their bioactivities were tested against E.coli cells. The taxonomic identity of the fungus was confirmed by ITS sequencing of its ribosomal DNA.
Mutagenesis of Lysines 156 and 159 in Human Immunodeficiency Virus Type 1 Integrase (IN) Reveals Differential Interactions between these Residues and Different IN Inhibitors
Authors: Crosby David C. , Lei Xiangyang , Gibbs Charles G. , Reinecke Manfred G. , Robinson W. Edward
Published: March 2019

Human immunodeficiency virus (HIV) type 1 integrase (IN) active site, and viral DNA-binding residues K156 and K159 are predicted to interact both with strand transfer-selective IN inhibitors (STI), e.g. L-731,988, Elvitegravir (EVG), and the FDA-approved IN inhibitor, Raltegravir (RGV), and strand transfer non-selective inhibitors, e.g. dicaffeoyltartaric acids (DCTAs), e.g. L-chicoric acid (L-CA). To test posited roles for these two lysine residues in inhibitor action we assayed the potency of L-CA and several STI against a panel of K156 and K159 mutants. Mutagenesis of K156 conferred resistance to L-CA and mutagenesis of either K156 or K159 conferred resistance to STI indicating that the cationic charge at these two viral DNA-binding residues is important for inhibitor potency. IN K156N, a reported polymorphism associated with resistance to RGV, conferred resistance to L-CA and STI as well. To investigate the apparent preference L-CA exhibits for interactions with K156, we assayed the potency of several hybrid inhibitors containing combinations of DCTA and STI pharmacophores against recombinant IN K156A or K159A. Although K156A conferred resistance to diketo acid-branched bis-catechol hybrid inhibitors, neither K156A nor K159A conferred resistance to their monocatechol counterparts, suggesting that bis-catechol moieties direct DCTAs toward K156. In contrast, STI were more promiscuous in their interaction with K156 and K159. Taken together, the results of this study indicate that DCTAs interact with IN in a manner different than that of STI and suggest that DCTAs are an attractive candidate chemotype for development into drugs potent against STI-resistant IN.
Chemical Composition and Antifungal Activity of Aaronsohnia pubescens Essential Oil from Algeria
Authors: Makhloufi Ahmed , Larbi L. Ben , Moussaoui Abdallah , Lazouni Hamadi A. , Romane Abderrahmane , Wanner Jürgen , Schmidt Erich , Jirovetz Leopold , Höferl Martina
Published: March 2019

In the present study, the chemical composition of the essential oil obtained from the aerial parts of Aaronsohnia pubescens (Desf.) K. Bremer & Humphries (Asteraceae), a chamomile-like medicinal plant, was studied. Using both GC-MS and GC-FID methods, 58 volatile compounds could be identified representing 96.6% of the total essential oil composition. The main compounds in the essential oil were monoterpene hydrocarbons such as ( Z)-β-ocimene (53.8%), myrcene (15.2%) and α-pinene (7.7%). Moreover, the essential oil of A. pubescens was tested for its antifungal activity against seven strains of phytopathogenic fungi, i.e. Aspergillus niger, A. flavus, Penicillium purpurogenum, P. jensenii, P. expansum, and Fusarium oxysporum f.sp. albedinis, using the disc diffusion method. With the exception of P. jensenii, A. pubescens essential oil demonstrated a considerable antifungal activity against all tested strains. The present results confirm the traditional use of A. pubescens as a food preservative.
Triterpenoids as Neutrophil Elastase Inhibitors
Authors: Guillaume Dom , Huynh Thi Ngoc Tram , Denhez Clément , Nguyen Kim Phi Phung , Belaaouaj Azzaq
Published: March 2019

Neutrophile elastase has the capacity to degrade elastin, a protein found in the connective tissue of the lungs. Unchecked elastase leads to pulmonary pathologies. Therefore, the development of elastase inhibitors is currently actively pursued in the therapeutic field. Several triterpenoids have been reported as inhibitors against elastase or its release. Such compounds could be valuable for the design of new drugs. This review is aimed at giving a comprehensive insight into the recent work performed in the field of triterpenoid-induced elastase inhibition.
Review of β-carboline Alkaloids from the Genus Aspidosperma
Authors: Layne Tanya H. , Roach Joy S. , Tinto Winston F.
Published: March 2019

Plants belonging to the genus Aspidosperma, a member of the family Apocynaceae, provide a rich source of β-carboline alkaloids, which makes them potentially poisonous. However, some of these alkaloids possess antitumor and antimicrobial activity. The present review is a survey of the β-carboline alkaloids and shows that they comprise of a diverse array of structural modifications.
Protective Effect of Compound K on Diabetic Rats
Authors: Shao Xiaotong , Li Na , Zhan Jinzhuo , Sun Hui , An Liping , Du Peige
Published: March 2019

Purpose Compound K (CK), the metabolic product of protopanaxadiol saponin in vivo, has many pharmacological activities. In this study, we discuss the preparation of CK, and its protective effect on kidneys of diabetic rats. CK was prepared from ginsenoside Rb1 after transformation by β-glucosidase, separation and purification by silica gel column chromatography. In the present study, we established a rat model of diabetes mellitus using high-fat diet and streptozotocin (STZ). After seven weeks of treatment, the levels of fasting blood glucose (FBG), total cholesterol (TC), total glycerin (TG), high-density lipoprotein (HDL-C), low-density lipoprotein (LDL-C), blood urea nitrogen (BUN), uric acid (UA), serum creatinine (Scr), malondialdehyde (MDA), glutathione (GSH), and superoxide dismutase (SOD) activity and glutathione peroxidase (GSH-PX) were evaluated in normal and diabetic rats. Also, renal pathomorphism changes were observed by HE stain, and TGF-β1 protein expression in the renal tissue was measured by Western blot. The yield of CK was 14.55 mg/mL, which was higher than that of other methods. After seven weeks, CK could decrease FBG, TC, TG, LDL-C, BUN, UA, Scr and MDA of diabetic rats, while CK also enhanced HDL-C and GSH, SOD and GSH-PX. Additionally, CK improved the pathological changes and decreased TGF-β1 protein expression in the renal tissue. CK improved the pathological changes in the renal tissue, enhanced the antioxidant capacity, reduced the damage of TGF-β1 to renal tissue, and protected the diabetic rats.
Effect of Puerarin on Expression of Fas/FasL mRNA in Pulmonary Injury induced by Ischemia-Reperfusion in Rabbits
Authors: Zheng Mengxiao , Song Dong , Luo Ziyin , Lu Zhongqiu , Wu Yiming , Wang Wantie
Published: March 2019

The effect of puerarin (Pur) on expressions of Fas/FasL mRNAs in pulmonary ischemia and reperfusion injury (PIRI) in rabbit was investigated. The sole side lung ischemia and reperfusion model was used. Rabbits were randomly divided into three groups, a sham operated group (sham, n = 10), PIR group (IR, n =30) and PIR + Pur group (Pur, n =30). Changes of several parameters including apoptotic index (AI), wet to dry ratio of lung tissue weight (W/D) and index of quantitative assessment of histologic lung injury (IQA) were measured after 60, 180 and 300 minutes of reperfusion. Meanwhile, the location and expression of Fas/FasL mRNA were investigated. Lung tissue was prepared for light microscopic and electron microscopic observation after 60, 180 and 300 minutes of reperfusion. Compared with group IR, Fas/FasL mRNAs were slightly expressed in intima and extima of small pulmonary artery, alveoli, and bronchiole epithelia in group Pur. The values of AI, W/D and IQA were significantly lower than those in group IR after 60, 180, and 300 minutes of reperfusion in lung tissue ( P <0.01 or P <0.05). Meanwhile, the abnormal changes in lung tissue morphology were markedly less in group Pur. Puerarin notably protects lung from PIRI by inhibiting Fas/FasL mRNA expression and decreasing lung cell apoptosis in rabbits.
Antibacterial Triterpenoids from the Bark of Sonneratia alba (Lythraceae)
Authors: Harizon  , Pujiastuti Betry , Kurnia Dikdik , Sumiarsa Dadan , Shiono Yoshihito , Supratman Unang
Published: March 2019

The new lupane-type triterpenoid, 3β-hydroxy-lup-9(11), 12-diene, 28-oic acid (1), along with two known lupane-type triterpenoids, lupeol (2) and lupan-3p-ol (3), were isolated from the bark of Sonnetaria alba. The structure of the new compound was elucidated on the basis of spectroscopic and mass spectrometric data analysis. Using the broth microdilution method, all compounds exhibited antibacterial activity against the Gram-positive bacteria Staphylococcus aureus ATCC 6538 and Streptococcus mutans ATCC 25175, with minimum inhibitory concentrations ranging from 15-33 to 35-55 ng/mL, respectively.
Quantitative Analysis of Bioactive Carbazole Alkaloids in Murraya koenigii
Authors: Joshi Trapti , Mahar Rohit , Singh Sumit K. , Srivastava Piush , Shukla Sanjeev K. , Mishra Dipak K. , Bhatta R.S. , Kanojiya Sanjeev
Published: March 2019

Carbazole alkaloids induce apoptosis in HL-60 cells through activation of the caspase-9/caspase-3 pathway and they are targeted as potential anticancer agents. Thus, the naturally occurring carbazole alkaloids become important as precursors for lead optimization in drug development. A method based on ultra performance liquid chromatography coupled with photodiode-array detection was developed using reverse phase isocratic elution with 85:15 acetonitrile and ammonium acetate buffer (5 mM). Seven samples of Murrya koenigii (L.) Spreng. from north-central India ( Uttar Pradesh) were analyzed. All three targeted analytes, koenimbidine (mk1), koenimbine (mk2) and mahanimbine (mk3), were well separated within 4.0 min with linearity of the calibration curves (r2 > 0.999). The limits of detection and quantification of mk1, mk2 and mk3 were 0.7, 0.4, 0.04 μg/mL and 2.14, 1.21, 0.12 μg/mL, respectively. The natural abundance of mk1, mk2 and mk3 was 0.06 - 0.20, 0.04 - 0.69 and 0.13 - 0.42%, w/w, respectively, in the dried powdered leaves, whereas, the tissue specific distribution of carbazole alkaloids was observed in the order of predominance, mk1 leaf>root>fruit>stem, mk2 fruit>leaf >stem>root, and mk3 fruit>leaf>root>stem. The developed method was validated for limits of detection and quantification, repeatability, accuracy, precision and stability. This is the first report on the natural abundance of the major carbazole alkaloids in M. koenigii and the method developed can be used in HPLC/UPLC systems.
Anthocephaline, a New Indole Alkaloid and Cadambine, a Potent Inhibitor of DNA Topoisomerase IB of Leishmania donovani (LdTOP1LS), Isolated from Anthocephalus cadamba
Authors: Kumar Ashish , Chowdhury Somenath Roy , Jatte Kumar Kalyan , Chakrabarti Tulika , Majumder Hemanta K , Jha Tarun , Mukhopadhyay Sibabrata
Published: March 2019

Chemical investigation of the stem bark of Anthocephalus cadamba has resulted in the isolation of anthocephaline (1), a new indole alkaloid, along with strictosamide (2), vincosamide (3) and cadambine (4). The structures of the isolated alkaloids (1-4) were established by detailed 2D NMR spectral analysis. Cadambine (4) exhibited potent DNA topoisomerase IB inhibitory activity.
Coumarins from Murraya paniculata var. zollingeri Endemic to the Timor Islands
Authors: Teshima Naoko , Yamada Hiromi , Ju-ichi Motoharu , Uji Tahan , Kinoshita Takeshi , Ito Chihiro
Published: March 2019

Four new coumarins, murrangatin-1′-senecioate (1), 5-methoxypanial (2), mexoticin-2′-senecioate (3) and murralongic acid (4), were isolated from the leaves of Murraya paniculata var. zollingeri, together with 23 known coumarins. The structures of the new compounds were elucidated based on spectroscopic data. The taxonomic status of M. paniculata var. zollingeri is briefly discussed, along with its similarity to M. paniculata.