bluuebunny/crossref_metadata_2025 huggingface dataset:
Monoamine Oxidase Inhibitory Activity of Biflavonoids from Branches of Garcinia gardneriana (Clusiaceae)
Authors: Recalde-Gil Maria Angélica , Klein-Júnior Luiz Carlos , dos Santos Passos Carolina , Salton Juliana , de Loreto Bordignon Sérgio Augusto , Monace Franco Delle , Filho Valdir Cechinel , Henriques Amélia Teresinha
Published: March 2019

Garcinia gardneriana is chemically characterized by the presence of biflavonoids. Taking into account that flavonoids are able to inhibit monoamine oxidase (MAO) activity, in the present study, the chemical composition of the branches’ extract of the plant is described for the first time and the MAO inhibitory activity of the isolated biflavonoids was evaluated. Based on spectroscopic and spectrometric data, it was possible to identify volkesiflavone, morelloflavone (1), Gb-2a (2) and Gb-2a-7- O-glucoside (3) in the ethyl acetate fraction from ethanol extract of the branches. Compounds 1-3 were evaluated in vitro and demonstrated the capacity to inhibit MAO-A activity with an IC50 ranging from 5.05 to 10.7 μM, and from 20.7 to 66.2 μM for MAO-B. These inhibitions corroborate with previous IC50 obtained for monomeric flavonoids, with a higher selectivity for MAO-A isoform. The obtained results indicate that biflavonoids might be promising structures for the identification of new MAO inhibitory compounds.
Chemical Composition and Antioxidant Activity of Cirsium vulgare Inflorescences
Authors: Nazaruk Jolanta , Chłędzik Sebastian , Strawa Jakub , Bazydło Katarzyna , Wajs-Bonikowska Anna
Published: March 2019

The chemical composition of Cirsium vulgare flower heads was examined. Petrol and chloroform extracts of this plant material were analyzed by GC-MS for the presence of fatty acids, phytosterols, and triterpenes. Diethyl ether, ethyl acetate, and butanol fractions of the methanolic extract were subjected to multistep chromatographic separations, and as a result, fourteen flavonoids were obtained (1–14). All compounds were isolated from this morphological part for the first time and eleven from the plant. Among the identified components were four aglycones, eight glycosides, and two glycoside esters, derivatives of apigenin, luteolin, kaemferol, and quercetin. One of them was a rarely occurring compound apigenin 7- O-β-(6″-butyl)-glucuronide) (14). Total flavonoid content and antioxidant activity were determined in the various fractions of methanolic extract.
Main Constituents and Antidiabetic Properties of Otholobium mexicanum
Authors: Suárez Alírica I. , Thu Zaw Min , Ramírez Jorge , León Diana , Cartuche Luis , Armijos Chabaco , Vidari Geovanni
Published: March 2019

Two phenols, bakuchiol (1) and 3-hydroxybakuchiol (2), and two isoflavone glycosides, daidzin (3) and genistin (4) were isolated from Otholobium mexicanum J. W. Grimes (Fabaceae). Moreover, the ability of the raw extract and isolated metabolites to inhibit the enzymes α-amylase and α-glucosidase was evaluated in vitro. In the α-amylase assay, the methanolic extract exhibited a moderate inhibitory activity with an IC50 of 470 μg/mL, while inhibition percentages of bakuchiol (1), 3-hydroxybakuchiol (2), and daidzin (3) were less than 25% at the maximum dose tested (1 μM). Genistin (4) exhibited a poor activity with an IC50 of 805 μM. In the α-glucosidase assay, the methanolic extract exhibited a strong inhibitory activity with an IC50 value of 32 μg/mL, while 3-hydroxybakuchiol (2) exhibited a moderate inhibitory activity with an IC50 of 345 μM. Daidzin (3) and genistin (4) exhibited lower inhibitory activity with IC50 values of 564 μM and 913 μM, respectively. Bakuchiol (1) exhibited a poor inhibitory activity with an inhibition percentage less than 10% at the maximum dose tested (1 mM).
Arbutin Content and Tyrosinase Activity of Bergenia Extracts
Authors: Tůmová Lenka , Dolečková Iva , Hendrychová Helena , Kašparová Marie
Published: March 2019

The total arbutin content in the leaves of all the studied Bergenia plants ( B. crassifolia, B. ciliata and B. x ornata) was determined. The highest values of the arbutin content have been established for B. crassifolia (58.9 ± 0.7 mg.g−1 DW) and B. x ornata (51.0 ± 1.21 mg.g−1 DW), and the lowest for B. ciliata (5.9 ± 0.6 mg.g−1 DW). Arbutin concentration in the Bergenia leaves was the lowest in spring, in the autumn, on the contrary it increased. All the tested aqueous extracts caused a dose-dependent increase in diphenolase activity of fungal tyrosinase in a similar way as arbutin. On the other hand, all the ethanol extracts inhibited the diphenolase activity of tyrosinase.
Chemical Investigation on Leaf, Flower and Fruit Oils of Lantana camara from Côte d'Ivoire
Authors: Nea Fatimata , Tanoh Evelyne Amenan , Yapi Thierry Acafou , Garcia Gabriel , Tomi Felix , Tonzibo Zanahi Félix
Published: March 2019

The compositions of essential oil obtained from leaves, flowers and fruits of Lantana camara L. growing in wild at Côte d'Ivoire, were investigated by GC and 13C NMR. Thirty-seven compounds accounting for 88.3-94.5% of the oils have been identified. The leaf, flower and fruits of L. camara produced sesquiterpene-rich essential oils predominated by ( E)-β-caryophyllene and α-humulene, in addition to the important content of sabinene, β-phellandrene and thymol as monoterpenes. It was found the new chemical profiles of L. camara.
Cytotoxic Terphenyl Neolignans from Fungus Terana coerulea: New Natural Corticins D and E, and Revised Structure for Corticin A
Authors: Maisterra Maitane , Castro M Ángeles , Muñoz-Centeno Luz M , Calhelha Ricardo C. , Ferreira Isabel C.F.R. , García Pablo A.
Published: March 2019

The cobalt crust fungus Terana coerulea ( Phanerochaetaceae family) was selected for a bio-guided study after an ethnobotanical survey at the Irati's Forest (Navarra, Spain) for its local use as antibiotic. Six extracts of increasing polarity, from hexane to hot water, were obtained from powdered dry fungi and tested for cytotoxicity against four human tumour cell lines and one non-tumour primary cell culture. From the most cytotoxic, EtOAc extract, we isolated and identified three terphenyl neolignans: two of them new natural products, named corticins D and E, and one previously described as corticin A, whose earlier structure has been revised. Their structural elucidation and biological evaluation as cytotoxic agents are described.
Occurrence and Chemical Synthesis of Apocarotenoids from Mucorales: A Review
Authors: Barrero Alejandro F. , del Pino M. Mar Herrador , Arteaga Jesús F. , González-Delgado José A.
Published: March 2019

Apocarotenoids are metabolites originated by degradation of carotenes through the loss of carbon atoms placed at the side chain of their structure as consequence of oxydative reactions. We present here the first review of apocarotenoids in the fungi mucorales Phycomyces blakesleeanus, Blakeslea trispora and Mucor mucedo. This review is divided into two parts: the first one presents their structures and sources, whereas the second part is dedicated to their chemical synthesis.
Physicochemical Characterization and Biological activities of Sulfated Polysaccharides from Cultivated Solieria filiformis Rhodophyta
Authors: Caamal-Fuentes Edgar , Robledo Daniel , Freile-Pelegrín Yolanda
Published: March 2019

Crude and alkali treated carrageenan from the cultivated marine alga Solieria filiformis (Rhodophyta) were obtained, characterized and evaluated for their cytotoxic and antiprotozoal activities. Yields, molecular weights and chemical composition of carrageenans were determined. Their structures were elucidated through spectroscopic techniques including FT-IR and CP-MAS 13C NMR spectra. Crude and alkali treated carrageenan seems to be chemically similar to the iota-family carrageenan. Crude carrageenan showed antiprotozoal activity against Giardia intestinalis.
Antiviral and Cytotoxic Activities of Polysaccharides Extracted from Four Tropical Seaweed Species
Authors: Bedoux Gilles , Caamal-Fuentes Edgar , Boulho Romain , Marty Christel , Bourgougnon Nathalie , Freile-Pelegrín Yolanda , Robledo Daniel
Published: March 2019

Polysaccharides extracted from Rhodymenia pseudopalmata, Solieria filiformis, Hydropuntia cornea (Rhodophyta) and Sargassum fluitans (Phaeophyceae) were evaluated for its cytotoxic and antiviral activities against Herpes simplex virus (HSV-Type 1). Chemical structures were characterized by FT-IR spectroscopy and 13C-NMR analyses. Polysaccharides from Sargassum fluitans (EC50 = 42.8 μg/ml) and Solieria filiformis (EC50 = 136.0 μg/ml) showed antiviral activity against herpes simplex virus type-I in vitro at a multiplicity of infection (MOI) of 0.01 ID50/cells without cytotoxicity (1–200 μg/mL). The activity observed suggests that sulphation, molecular weight and carbohydrate nature of these polysaccharides may be involved in this activity. To better understand the antiviral activity of the polysaccharides evaluated, it seems important to study the mechanism of action involved. These polysaccharides could be studied further to evaluate their potential use as antiviral drugs.
Mathematical Modeling of Drug Release from Natural Polysaccharides Based Matrices
Authors: Chiarappa Gianluca , Abrami Michela , Dapas Barbara , Farra Rossella , Trebez Fabio , Musiani Francesco , Grassi Gabriele , Grassi Mario
Published: March 2019

The new concept of personalized medicine and the affirmation of Nucleic Acid Based Drugs (NABDs), an emerging class of bio-drugs constituted by short sequences of either DNA or RNA, represent a new challenge for the mathematical modelling in the drug delivery and adsorption field. Indeed, whether patient uniqueness asks for the use of theoretical tools enabling a rational approach adapting to each patient, NABDs delivery brings to our attention new aspects of drug delivery due to the NABDs fragile nature and way of action. This review aims to present and discuss the mathematical modelling of drug release from natural polysaccharides matrices with particular care to the description of the chemical and physical phenomena ruling drug delivery.
Pallidopenillines: Polyketides from the Alga-Derived Fungus Penicillium thomii Maire KMM 4675 as Stimulators of the Initial Stages of Crop Plant Development
Authors: Chaikina Elena L. , Sobolevskaya Maria P. , Afiyatullov Shamil Sh. , Aminin Dmitry L. , Anisimov Mikhail M.
Published: March 2019

The pallidopenilline A (I), 1-acetylpallidopenilline A (II), 1-deacetylpallidopenilline B (III) and pallidopenilline C (IV) isolated from marine fungus Penicillium thomi Maire KMM 467 5 were examined for their ability to stimulate growth of seedling roots of buckwheat ( Fagopyrum esculentum Moench), soy { Glycine max (L.) Merr.}, barley ( Hordeum vulgare) and wheat ( Triticum aestivum L.). The stimulatory effects depend on the chemical structure of the compounds and on the plant species. Compound I was efficient for growth of seedling roots of soy, barley and wheat. Compound II and III were efficient for growth of seedling roots of soy and barley. Compound IV was efficient for growth of seedling roots of buckwheat. These compounds can be recommended for field study as plant growth stimulators.
Withanolides as Potential Immunosuppressive Agents against RAW264.7 Cells from the Pericarps of Datura metel
Authors: Yang Bing-You , Zhou Yong-Qiang , Liu Yan , Lu Zhen-Kun , Kuang Hai-Xue
Published: March 2019

Two new withanolides, daturafoliside V (1) and daturafoliside W (2) with three known ones, daturametelin J (3), daturataturin A (4) and daturataturin B (5) were isolated from the pericarp of Datura metel L.. The structures of these compounds were identified by the analyses of spectroscopic data. And their inhibitory activities were evaluated by acting on RAW264.7 cells. Moreover, their molecular mechanisms are discussed based on the p-ERK, p-JNK, p-p38 and NF-κBp65 expression levels. As a result, the new one, compound 2 (IC50 38.3 μM) exhibited the potential immunosuppressive activity. Our datas indicate that studies on the pericarps of D. metel have great potential to discover new compounds and provide new resource for pharmacology research.
Flavonoids with Hepatoprotective Activity from the Leaves of Cleome chelidonii
Authors: Nguyen Tan Phat , Mai Dinh Tri , Do Thi Hong Tuoi , Phan Nhat Minh
Published: March 2019

One new flavonol glycoside, named cleomeside C (1), together with eight known flavonol glycosides (2–9) were isolated by various chromatography methods from the leaves of Cleome chelidonii. Their structures were elucidated by IR, UV, HR-ESI-MS, NMR (1D & 2D) experiments. Compounds 2–8 were isolated for the first time from the genus Cleome. The cytotoxicity and hepatoprotective activity in HepG2 human hepatoma cell line of compounds (1–3 and 6) were measured by MTT assay. At the concentration of 25 μM and 50 μM, compound 2 as well as compound 3 at 25 μM showed cytotoxic activity (cell viability was decreased 21.7%, 31.8% and 21.8%, respectively, compared to control). Compounds 2 and 6 expressed hepatoprotective effect at the concentration of 100 μM with prevention percentage of 32.3% and 34.3%, respectively, compared to that of 80.3% of quercetin positive control).
Genotoxic and Antigenotoxic Activities of Thai Bee Pollen and Its Extracts in Human Lymphocytes by in Vitro Sister Chromatid Exchange Assay
Authors: Ratanavalachai Treetip , Thitiorul Sumon , Jansom Chalerm , Jenkhetkan Wantha , Itharat Arunporn
Published: March 2019

Bee pollen has been used as a food supplement and as a traditional medicine for thousands of years. Our study demonstrated that by in vitro sister chromatid exchange assay, Mimosa pudica crude bee pollen extract (0.005-5.0 μg/mL CE) from Chiangmai, Northern Thailand, increased genotoxicity in human lymphocytes at concentrations of 0.005 and 0.5 μg/mL by 20% and 24% respectively, compared to the RPMI control. Its defatted extract (DE) at 0.005-5.0 μg/mL increased the activities by 24–32% whereas the lipid extract (LE) at 0.00125 μg/mL but not at 0.0125–1.25 μg/mL increased the activities by 25%. Only CE at 5.0 μg/mL induced cytotoxicity. Pretreatments of CE, DE, and LE at 0.5, 5, and 0.00125 μg/mL induced antigenotoxicities against doxorubicin, a potent genotoxic chemotherapeutic agent by 24%, 28%, and 16%, respectively. Their protective mechanisms are feasibly involved with α-tocopherol and phenolic contents such as gallic acid and ferulic acid.
Catalyst-Free Synthesis of Novel 6-Phenyl-6H-chromeno [4, 3-b] quinoline Derivatives at RT: Their Further Structure Evaluation Leads to Potential Anti-cancer Agents
Authors: Kumar Alleni Suman , Kumar Rathod Aravind , Satyanarayana Vavilapally , Reddy Elala Pravardhan , Reddy Boggu Jagan Mohan , Kumar Duddukuri Nandan , Khurana Amit , Chandraiah Godugu , Yadav Jhillu Singh
Published: March 2019

A variety of novel quinoline derivatives (6-phenyl-6 H-chromeno [4,3- b] quinoline) have been prepared by using 4-chloro-2-phenyl-2 H-chromene-3-carbaldehyde and various substituted of aromatic anilines as starting materials. This is the first example on the preparation of quinolines through this novel method. And the resulting quinoline derivatives further structure evolution is leads to an anti cancer agents. Our preliminary data of model compound (7i) on three cancer cell lines (B16F10, MCF7 and A549) suggested decent anticancer activity on two cell lines (B16F10 and MCF7) with IC50 values of 14.8 and 21.32 μM, respectively. This method is operationally simple and works with a diverse range of substrates.
Chemical Diversity in Ligularia oligonema
Authors: Kuroda Chiaki , Inagaki Kou , Okamoto Yasuko , Tori Motoo , Hanai Ryo , Yamada Hiroka , Nagano Hajime , Gong Xun
Published: March 2019

The chemical composition of a sample of the title species collected in Pianma, Lushui County, Yunnan Province of China, was examined. Two 3,6,10-oxygenated and two 3,6-oxygenated furanoeremophilanes were isolated. Structures of two new compounds were elucidated. The 3,6-oxygenated furanoeremophilanes were not detected in a sample of the same species previously collected in Laojunshan, Jianchuan County, Yunnan, indicating chemical diversity in the species.
A New Diterpenoid and a Lignan from Pinus thunbergii
Authors: Sono Masakazu , Yamaguchi Hitomi , Nakashima Katsuyuki , Tori Motoo
Published: March 2019

Phytochemical analysis of Pinus thunbergii Parl. afforded eleven compounds, two of which were new. One was 8β,12ξ-dihydroxylabd-13( E)-en-19-oic acid and the other was a lignan acetate. The NMR data of all isolated compounds were recorded.
Apowalsogynes A and B, Two Highly Oxidized 3,4-Seco-Apotirucallane Triterpenoids from Walsura chrysogyne
Authors: Nugroho Alfarius Eko , Okuda Maho , Yamamoto Yukari , Chin-Piow Wong , Hirasawa Yusuke , Kaneda Toshio , Shirota Osamu , Hadi A. Hamid A. , Morita Hiroshi
Published: March 2019

Two new 3,4- seco-apotirucallane triterpenoids, Apowalsogynes A and B (1 and 2), were isolated from the barks of Walsura chrysogyne, and their structures were determined on the basis of the NMR and CD spectra, and by using the modified Mosher's method. In addition, the cytotoxic activities of 1 and 2 against various cancer cell lines were evaluated.
Bioactive Compounds Isolated from Indonesian Epiphytic Plant of Sarang Semut and Their Antibacterial Activity against Pathogenic Oral Bacteria
Authors: Kurnia Dikdik , Sumiarsa Dadan , Dharsono Hendra D.A. , Satari Mieke H.
Published: March 2019

A new phenolic compound (1), a steroid (2), a new steroid glycoside (4), two triterpenoids (3 & 6) and a new phloroglucinol-sesquiterpene (5) have been isolated from the ethyl acetate extract of Sarang Semut ( Myrmecodia pendans) and their structures were determined on the basis of the spectral data. The bioactivity evaluation was conducted with the inhibition zone of compounds (mm) using Kirby-Bauer method at concentrations of 1000 and 5000 ppm for compound 1 against pathogenic oral bacteria Enterococcus faecalis, was 8.55 and 8.05 mm, respectively. Compounds 2–3 against Streptococcus mutans were 9.00 and 8.45 mm (2) and 10.24 and 9.35 mm (3), respectively. Compound 5 against Porphyromonas gingivalis was 11.5 and 10.8 mm, respectively.
Potential Secondary Metabolites from Marine Sponge Aaptos aaptos for Atherosclerosis and Vibriosis Treatments
Authors: Mohamad Habsah , Rosmiati  , Muhammad Tengku Sifzizul Tengku , Andriani Yosie , Bakar Kamariah , Ismail Noraznawati , Saidin Jasnizat , Latip Jalifah , Musa Najiah , Parenrengi Andi
Published: March 2019

Natural products play a crucial role in drug discovery. In the last decade, the advent of marine natural product research has produced a remarkable number of compounds, particularly those isolated from marine sponges, with a broad range of activities for the treatment of human and animal diseases. In this study, five known alkaloids namely aaptamine (1), 9-demethylaaptamine (2), 4- N-methylaaptamine (3), 9-methoxyaaptamine (4), 9-demethyloxyaaptamine (5), an uncommon amide in sponge, 4-hydroxybenzamide (6) and 3 β,5α-cholesterol (7) were isolated from the butanol extract of Aaptos aaptos (Schmidt, 1864) by bioactivity-guided isolation. Their structures were determined based on a detailed analysis of their 1D and 2D spectroscopic NMR and EIMS spectral data as well as comparison with literature data. Cytotoxic activity and anti-atherosclerotic property of the compounds were determined based on their ability to increase the transcriptional activity of SRB1 promoter and PPRE in human liver HepG2 cell line. The results showed that compounds 4 and 7 exhibited cytotoxic effects and compounds 1–4 and 7 increased the transcriptional activity of SRB1 promoter and PPRE. This suggests that compounds isolated from A. aaptos may have potential as anti-cancer agents and to reduce the progression of atherosclerosis. In addition, the compounds 1–4 displayed antibacterial activity against shrimp pathogenic bacteria, Vibrio harveyi and Vibrio sp. This suggests that the compounds have potential as vibriosis treatment.
Seasonal Variability of Genistein and 6-Hydroxykynurenic Acid Contents in Ginkgo biloba Leaves from Different Areas of China
Authors: Yao Jian B. , Du Xin , Jin Hui H. , Fang Ling , Min Hui , Qiao Hong X. , Wang Ru W. , Kuchta Kenny
Published: March 2019

Refined extracts of Ginkgo biloba L. leaves can protect brain tissue from diverse types of tissue damage. Preliminary experiments identified 6-hydroxykynurenic acid (6-HKA) as a central contributor to this effect, and thus as a potential active marker for drug quality analysis. In contrast, genistein is a negative quality marker for this drug, as high contents of this compound in G. biloba leaves samples are in most cases caused by adulteration with Sophora flavescens Aiton, which is added to the extract by unlawful producers in order to boost its content in flavones, which serve as a quality marker. Some publications even dispute the natural occurrence of genistein in G. biloba leaves altogether, thus claiming that its presence even in trace amounts would prove adulteration. The present study aims to resolve the influence of harvesting time and location on the contents of genistein and 6-HKA - HPLC: Agilent SB-C18 column (5 μm, 4.6×250 mm); phosphoric acid pH2.5, acetonitrile, methanol, gradient; 1 mL/min; 25°C; UV 350 nm - in G. biloba leaves. The lowest contents of 6-HKA were observed in July and August, whereas the maximum was reached in May and October. In the case of genistein - its natural occurrence in G. biloba leaves could be demonstrated under controlled conditions for the first time - the lowest contents were found in May and June, whereas the highest were detected in September and October. These results show that harvesting of G. biloba leaves for pharmaceutical use should be avoided in July and August because of the reduced 6-HKA content, as well as in September and October, the season of highest genistein production. Due to both favorable 6-HKA production and a relative lack of genistein, May was identified as the ideal harvesting month for G. biloba leaves.
Prenylated Isoflavanones from the Stem Bark of Erythrina poeppigiana (Leguminosae) and its Antimalarial Properties
Authors: Herlina Tati , Aloanis Anderson Arnold , Kurnia Dikdik , Harneti Desi , Maharani Rani , Supratman Unang
Published: March 2019

During the course of our continuous search for novel antimalarial compounds derived from the Indonesian Erythrina plants, the methanol extract of the stem bark of Erythrina poeppigiana demonstrated significant antimalarial activity against Plasmodium falciparum parasites, in vitro. Bioassay-guided fractionation of the ethyl acetate extract resulted in the isolation of three known platyisoflavanone (1), erypogein D (2), and sophoraisoflavanone A (3). Compounds 1–3 showed strong antimalarial activity against 3D7 strain of P. falciparum with IC50 values of 0.52, 0.36, and 3.65μM, respectively. This result indicates that stem bark of E. poeppigiana is a promising source of antimalarial agents, and merits further investigation.
Antioxidant and Antibacterial Constituents from Two Sumatran Ferns, Trichomanes javanicum and Oleandra pistillaris
Authors: Nofrizal  , Putra Deddi P. , Arbain Dayar
Published: March 2019

Mangiferin (1), vitexin (2) and 4- O-β-D-glucopyranosylcaffeic acid (3), by means of classical extraction, fractionation and chromatographic separation, have been isolated for the first time from aerial parts (stems and leaves) of Trichomanes javanicum Blume (Hymenophyllaceae) as well as 3,4-dihydroxybenzoic acid (4) and gallic acid (5) from the rhizome of Oleandra pistillaris (Sw.) C. Chr. (Oleandraceae). These compounds were characterized by spectroscopic methods and then compared to those of data reported in the literature. Compound (1) and (4) showed significant antioxidant activity (IC50 value was 3.89 and 3.83 μM respectively) twice stronger than ascorbic acid as standard (IC50 value 7.86 μM). Compound (4) and (5) significantly inhibited the growth of Salmonella thypimurium and S. thypi while compounds (1), (2) and (3) showed weak inhibition toward Staphylococcus aureus, Bacillus subtilis and Vibrio cholerae. All compounds were not active against Enterococcus faecalis and Streptococcus mutans.
Studies on Extraction Conditions to Increase the Content of Neurotrophic Compounds in the Bangle (Zingiber purpureum) Extract
Authors: Kubo Miwa , Kaga Sho , Harada Kenichi , Okamoto Yasuko , Kato Eishin , Hosoda Shinya , Fukuyama Yoshiyasu
Published: March 2019

To develop the Javanese ginger Bangle ( Zingiber purpureum), which contains neurotrophic phenylbutenoid compounds named banglenes 1 and 2, as a functional food additive for protection of neurodegenerative disease, we investigated conversion method from 3 to 1 and 2 under practical conditions available in food processing steps. After several trials, we found that dimerization of 3 proceeded smoothly under refluxing EtOH/H2O (1/3) in the presence of ubiquinone (0.1 eq) in sealed tube, giving rise to 1 and 2 in 54% yield. When this condition was applied for 70% EtOH extract of bangle, content of 1 and 2 in the extract was increased 2-fold by 2.1%.
Phytochemical, Synthetic and Biological Studies on Stemona and Stichoneuron Plants and Alkaloids: A Personal Perspective
Authors: Pyne Stephen G. , Jatisatienr Araya , Mungkornasawakul Pitchaya , Ung Alison T. , Limtrakul Pornngarm , Sastraruji Thanapat , Sastraruji Kwankamol , Chaiyong Sukanda , Umsumarng Sonthaya , Baird Morwenna C. , Dau Xuan Duc , Ramli Rosdayati Alino
Published: March 2019

This report is an overview of our research on phytochemical, synthetic and biological studies of the Stemona and Stichoneuron species of plants.
Perillyl Alcohol: Antinociceptive Effects and Histopathological Analysis in Rodent Brains
Authors: Benedito Rubens Batista , Alves Mateus Feitosa , Pereira Wendel Batista , de Arruda Torres Paula , Costa Jéssica Pereira , da Rocha Tomé Adriana , de Cássia da Silveira e Sá Rita , de Sousa Damião Pergentino , Ferreira Paulo Michel Pinheiro , de Freitas Rivelilson Mendes , de Fatima F. Melo Diniz Margareth , de Almeida Reinaldo Nóbrega
Published: March 2019

Perillyl alcohol (PA) is a natural compound found in essential oils. In this study, the antinociceptive activity of PA was evaluated using acetic acid and formalin tests. The involvement of the opioid system in its mechanism of action was investigated. Potential histological changes in the hippocampus and striatum were also assessed. In the acetic acid induced writhing tests, the mice pretreated with PA exhibited significant reductions in writhing. PA inhibited formalin injected paw licking response, and naloxone partially reversed the antinociceptive activity of perillyl alcohol during the writhing test. And as for the histopathological evaluation, PA did not cause significant tissue changes. This study suggests that PA possesses antinociceptive effects without significant hippocampus or striatum neurotoxicity, and that its activity involves opioid.
Effects of Paederia foetida and its Bioactive Phytochemical Constituent Lupeol on Hepatic Phase I Drug Metabolism
Authors: Dubey Sourabh , Mitra Kuntal , De Bijoy Kumar , Mondal Arijit , Bishayee Anupam
Published: March 2019

There are many possible complications associated with the concomitant use of herbs and medications, but limited information is available on herb-herb or herb-drug interactions. Paederia foetida Linn. (family: Rubiaceae) is utilized in the Indian traditional medicine. It exhibits various pharmacological properties, such as antidiabetic, analgesic, anti-inflammatory, antimicrobial, hepatoprotective, anthelmintic, antiulcer and antioxidant activities. The purpose of the present work was to investigate the inhibitory potential of the P. foetida ethanolic extract and its bioactive constituent lupeol on hepatic phase I drug metabolizing enzymes. The high performance thin layer chromatography was performed for qualitative analysis of various extracts of P. foetida. The effects of P. foetida extract on rat liver microsomes (RLMs) and individual cytochrome P-450 (CYP) isozymes (CYP3A4 and CYP2D6) were investigated using CYP450-carbon monoxide complex assay and fluorescence microplate assay, respectively. The ethanolic extract and lupeol (both at a concentration of 100 μg/mL) showed 45±3.3 and 44±3.8% inhibition of rat liver microsomes, respectively, which were significantly less than that of known inhibitor ketoconazole (74±5.4% inhibition at 100 μg/mL). The 50% inhibitory concentrations (IC50) of ethanolic extract on CYP3A4 and CYP2D6 were 78±2.3 and 82±3.1 μg/mL, respectively, whereas its major bioactive constituent lupeol has IC50 values of 83±2.0 and 84±2.6 μg/mL for CYP3A4 and CYP2D6, respectively. The results were of lesser magnitude compared to known inhibitors, ketoconazole and quinidine, respectively. The current study revealed that P. foetida has less inhibitory potential in comparison to that of known inhibitors, ketoconazole and quinidine, on two major drug metabolizing isozymes, CYP3A4 and CYP2D6. Thus, the use of P. foetida as a complementary or alternative medicine may be safe in regard to herb-drug interactions.
Fatsia polycarpa Triterpenoids and Acetylated Derivatives Thereof Inhibit Tumor Necrosis Factor-α-Induced Inflammation
Authors: Chou Chang-Hung , Lu Yan-Ting , Cheng Shi-Yie , Cheng Hsueh-Ling
Published: March 2019

Fatsia polycarpa Hayata is an evergreen shrub endemic to Taiwan and used locally to treat several inflammatory disorders. The crude extract of F. polycarpa has been proven to exhibit an anti-inflammatory effect in vitro and in vivo; however, which constituents of the extract confer the anti-inflammatory function remains unclear. Fatsicarpain D (Fat D) and fatsicarpain F (Fat F) are oleanane-type triterpenoids and two of the feature constituents of the F polycarpa extract. Ester substitution on C-3 has been proposed to enhance the activities of triterpenoids. Thus, this study compared and characterized the anti-inflammatory activities of Fat D, Fat F, and the C-3-acetylated derivatives thereof. These compounds were toxic to RAW 264.7 cells, but not to FL83B cells. The compounds dose-dependently inhibited tumor necrosis factor-α (TNF-α)-induced expression of inducible nitric oxide synthase in FL83B cells, with the IC50 values being Fat D 8.5 μM, acetylated Fat D 10.4 μM, acetylated Fat F 10.7 μM, and Fat F 27.4 μM, respectively. Thus, acetylation of C-3 improved the activity of Fat F. Moreover, the compounds suppressed TNF-α-induced expression of nuclear factor-κB (NF-κB) p65 subunit and protein tyrosine phosphatase-1B. Furthermore, they inhibited TNF-α-mediated activation of the inhibitor kappa B kinase (IKK), and that of the mitogen-activated protein kinases (MAPKs) extracellular-signal-regulated kinase (ERK), and c-Jun N-terminal kinase (JNK), but promoted the activation of MAPK p38, which was found to be anti-inflammatory in certain cell types. Thus, Fat D and Fat F exhibited obvious anti-inflammatory activities in vitro and inhibited ERK, JNK, and the IKK/NF-κB pathway.
Lactones and Flavonoids isolated from the Leaves of Globimetula braunii
Authors: Ja'afar Muhammad Kamal , Jamil Shajarahtunnur , Basar Norazah , Bakar Mohd Bakri , Sarker Satyajit D. , Flanagan Keith J. , Senge Mathias O.
Published: March 2019

The dried powdered leaves of Globimetula braunii (Engler) Van Tiegh were effectively extracted by the cold extraction method. Purification of the EtOAc-soluble and MeOH-soluble extracts successfully yielded two lactones namely ( R)-6-[( S)-2-hydroxy-4-(4-hydroxyphenyl)butyl]–5,6-dihydropyran-2-one (dodoneine) 1 and (1 R,5 S,7 S)-[2-(4-hydroxyphenyl)ethyl]-2,6-dioxabicyclo[3.3.1]-nonan-3-one (2), together with five flavonoids namely quercetin 3, (+)-catechin 4, quercitrin 5, rutin 6 and avicularin 7. Their structures were established by spectroscopic means, and the absolute configuration of compound 1 was confirmed by X-ray analysis.
Quantitative and Qualitative Analysis of Eruca sativa and Brassica juncea Seeds by UPLC-DAD and UPLC-ESI-QTOF
Authors: Sharma Arti , Sharma Ritika , Arora Rohit , Arora Saroj , Singh Bikram , Sharma Upendra
Published: March 2019

Eruca sativa and Brassica juncea belong to the Brassicaceae family and have been used traditionally for the treatment of cancer and various cardiovascular ailments. A rapid and simple ultra performance liquid chromatography (UPLC) method has been developed for the simultaneous quantification of erucin, allyl isothiocyanate and benzyl isothiocyanate in E. sativa and B. juncea oil. Eruca sativa oil contains erucin (28.93%), allyl isothiocyanate (0.06%) and benzyl isothiocyanate (0.70%). Identification of other secondary metabolites in E. sativa and B. juncea oil and aqueous methanolic extracts were also carried out using ultra performance liquid chromatography-electro spray ionization-quadrupole time of flight (UPLC-ESI-QTOF). The UPLC-ESI-QTOF based study leads to the identification of ten compounds in B. juncea oil and three compounds in E. sativa oil. The UPLC-ESI-QTOF analysis of aqueous methanolic extracts of E. sativa and B. juncea leads to the identification of eight and nine compounds, respectively.
HPLC Fingerprint Combined with Quantitation of Main Effective Components and Chemometrics as an Efficient Method for Quality Evaluation of Oviductus Ranae
Authors: Wang Shihan , Xu Yang , Wang Yanwei , Lv Zuying , Cui Qingyan , Jin Xiangqun , Wang Yongsheng
Published: March 2019

To ensure the highest quality of Oviductus Ranae products for consumers, an accurate, efficient, scientific and comprehensive evaluation method for assessing the quality of Oviductus Ranae was proposed in this paper. The fingerprint of Oviductus Ranae has been established based on the method of high performance liquid chromatography (HPLC). Oviductus Ranae from different habitats were analyzed by hierarchical cluster analysis (HCA). The HPLC profiles of fourteen batches of Oviductus Ranae showed 33 well-resolved common peaks in each chromatogram. Five of these were assigned to 1-methyl hydantoin, 7-ketocholesterol, 4-cholesten-3-one, cholesterol and stigmasterol. Contents of these five main effective components were determined in the meantime. Based on the HPLC profiles of all the samples, the reference HPLC fingerprint and similarity values were calculated by statistical software (SPSS 19.0). It was found that similarity value of all Oviductus Ranae samples were more than 0.85 and Oviductus Ranae from same habitats had similarity to some degree. In conclusion, the proposed method had good specificity, repeatability, stability and precision, which can provide a reference for the quality evaluation and identification of the medicine origin of Oviductus Ranae. Quantitation of effective components revealed that contents of five effective constituents in Oviductus Ranae obtained from Ji Lin province were the highest, followed by Hei Longjiang province and Liaoning province. The results of HCA showed that samples classified into one group were associated with their habitats. HPLC fingerprint combined with quantitation of main effective compounds and data analysis techniques can be an efficient and useful method for monitoring the quality of Oviductus Ranae.
Effect of Plant Essential Oils against Rophalosiphum padi on Wheat and Barley
Authors: Grul'ová Daniela , Mudrončeková Silvia , Zheljazkov Valtcho D. , Šalamon Ivan , Rondon Silvia I.
Published: March 2019

The aim of the present study was to evaluate the effect of six EOs against Rhopalosiphum padi L. (Homoptera: Aphididae). This aphid is one of the most important cereal pests worldwide. EOs used in this study were from cumin ( Cuminum cyminum L.; Apiaceae), hyssop ( Hyssopus officinalis L.; Lamiaceae), costmary ( Tanacetum balsamita L. syn. Chrysanthemum balsamita L. Baill; Asteraceae), lovage ( Levisticum officinale W.D.J. Koch; Apiaceae), lavander ( Lavandula angustifolia Mill; Lamiaceae) and thyme ( Thymus vulgaris L.; Lamiaceae). Cultivar ORCF-10, a soft white winter wheat ( Triticum aestivum L.) cultivar and barley ( Hordeum vulgare L.) cv. ‘Alba’ were selected for the bioassays. Each EO was diluted with acetone (w/v) at different concentrations ranging from 0.1 % to 1.0 %. Number of R. padi landing on treated or untreated leaves was counted 24 h after the initial aphid transfer. In general, the repellency effect increased as the concentration of EOs increased regardless of treatments with the exception of lovage. Regardless of the substrate and treatment, lower numbers of aphids were observed on treated leaves at higher concentrations compared to the untreated control stressing the repellency effect. This study demonstrated that the EOs of cumin, hyssop, costmary, lavender, and thyme may have potential for aphids control.
Further Guaianolides from Chrysophthalmum montanum
Authors: Gürbüz Perihan , Doğan Şengül D.
Published: March 2019

Five new guaiane type sesquiterpene lactones; 6β-hydroxy-guai-9(10)-en-12,8β-olide-4β- O- 1 -glucopyranoside (1), 6 β-acetoxy-guai-9(10)-en-12,8 1 -olide-4 β- O-β-glucopyranoside (2), 5α,10β-dihydroxy-guai-1(2)-en-12,8β-olide (3), 4β-hydroxy-guai-(2)-en-12,8β-olide-10- O-β-glucopyranoside (4a), 1α,4α,10α-trihydroxy-guaian-12,8β-olide (5) were identified in the repeated examination of the aerial parts of the Chrysophthalmum montanum (DC) Boiss. lie structures of the isolated compounds were elucidated by extensive 1D- and 2D-NMR spectroscopic analyses in combination with HRESIMS experiments.
Metabolomic and Proteomic Analysis of the Response of Angelica acutiloba after Herbivore Attack
Authors: Kato Risa , Morita Yusuke , Ina Atsutoshi , Tatsuo Yoshiaki , Tamura Takayuki , Tezuka Yasuhiro , Tanaka Ken
Published: March 2019

To investigate the effect of insect damage on the biosynthesis of secondary metabolites, we cultivated Angelica acutiloba with and without damage caused by the larvae of Papilio machaon. Compounds from the leaves and roots of A acutiloba were extracted with chloroform and analyzed by GC-MS. We annotated the peaks based on the mass spectral data and retention times. In addition, the effects of insect damage on the plants were investigated by principal component analysis (PCA). As a result, it was clarified that the amounts of ligustilide, γ-terpinene and β-caryophyllene, increased in leaves after being damaged by insects. Polyacetylenes also increased in the roots of damaged plants. In addition, as prompt responses, increases in the proteins relating to hydrogen peroxide synthesis and decreases in the proteins concerned with a non-urgent response to pathogenic attack were clarified by proteomic analysis. These results indicate that cultivation methods using the chemical-ecological response of the plant can contribute to the production of higher-quality crude drugs derived from A. acutiloba.
Cytotoxic Activities of Different Iranian Solanaceae and Lamiaceae Plants and Bioassay-Guided Study of an Active Extract from Salvia lachnocalyx
Authors: Mirzaei Hossein H. , Firuzi Omidreza , Baldwin Ian T. , Jassbi Amir Reza
Published: March 2019

Methanol (MeOH), dichloromethane (DCM) and 80% MeOH extractions of fourteen medicinal plants of the families Solanaceae and Lamiaceae collected from different area of Iran were tested for their cytotoxic potential against MOLT-4 human cancer cell lines. Cytotoxicity of the tested plants indicated that 11 plants had one or two active extracts (IC50 ≤50): MeOH extracts of the shoots of Thymus trautvetteri, Solanum luteum and stems of Lycium shawii; DCM extracts of the shoots of Thymus kotschyanus, Salvia persepolitana, Ballota aucheri, Nepeta glomerulosa, Hyoscyamus tenuicaulis, Salvia lachnocalyx, Salvia sharifii as well as the stems of Salvia verticillata and the roots of Salvia multicaulis and S. lachnocalyx; 80% MeOH extracts of the shoots of T. trautvetteri, S. luteum and the stems of L. shawii. The DCM extract of the aerial parts of S. lachnocalyx as one of the most active species was subjected to the cytotoxic bioassay-guided fractionation and purification using combination of chromatography methods. The bioassay-guided fractionation of DCM extract of the shoots of S. lachnocalyx led to the isolation of two cytotoxic compounds: (2 Z,6 Z,10 Z,14 E)-geranylfarnesol (1), a novel natural product, and spathulenol (2). Both of the isolated compounds, especially 1 (IC50 range: 9.6 −20.2 μg/mL), showed good cytotoxic effects against 3 human cancer cell lines, MOLT-4, MCF-7 and HT-29.
Efficient Bioproduction of Mycosporine-2-glycine, Which Functions as Potential Osmoprotectant, using Escherichia coli Cells
Authors: Patipong Tanutcha , Hibino Takashi , Waditee-Sirisattha Rungaroon , Kageyama Hakuto
Published: March 2019

Mycosporine-2-glycine (M2G) is known to be synthesized in halotolerant cyanobacterium Aphanothece halophytica. Escherichia coli cells in which the M2G synthetic genes of A. halophytica were introduced could synthesize M2G. Here, we report that M2G producing transformed E. coli cells showed salt tolerance compared to control cells. This result suggested that M2G could function as a potential osmoprotectant in E. coli. To our knowledge, this is the first report presenting the evidence that mycosporine-like amino acid confers salt tolerance on E. coli. Intracellular M2G content in the transformed E. coli cells were varied depending on NaCl concentration with maximum level at 0.75 M. Moreover, intracellular M2G level was affected by a supply of glycine with maximum level at 5 mM. In conclusion, we found that transformed E. coli cells could produce 205 μg of M2G/g fresh weight of cells under the best effective growth condition in this study. Thus, the results obtained here offer the potential for the bioproduction of mycosporine-like amino acids using the genetically engineered E. coli cells.
Anti-inflammatory Effect of Discretamine, a Protoberberine Alkaloid Isolated from Duguetia moricandiana
Authors: Lemos Danilo Eduardo Costa Vieira , Cavalcante-Silva Luiz Henrique Agra , de Almeida Lima Éssia , Alves Adriano Francisco , Lúcio Ana Silvia Suassuna Carneiro , Barbosa-Filho José Maria , Mascarenhas Sandra Rodrigues
Published: March 2019

Discretamine is a tetrahydroprotoberberine alkaloid isolated from Duguetia moricandiana (Annonaceae). In the present study, anti-inflammatory ability of discretamine in a lipopolysaccharide (LPS) stimulated macrophages model was investigated. LPS-induced NO production was reduced by discretamine treatment (100 and 200 μg/mL) around 50%. Furthermore, discretamine (50, 100, and 200 μg/mL) treatment down-regulated pivotal inflammatory cytokines levels, such as IL-6 (74.1, 76.6, and 75.1%, respectively), IL1-β (89.4, 87.4, and 71.8%, respectively), and TNF-α (61, 45.2, and 52.6%, respectively) levels. Also, discretamine did not reduce peritoneal macrophage viability. Besides that, in vivo carrageenan-induced paw edema experiments were also carried out. Discretamine treatment (5, 10, and 20 mg/kg) reduced paw edema up to 6h. Taken together, these data demonstrated that discretamine exerted its anti-inflammatory effect by down-regulation the levels of TNF-α, IL-6, and IL1-β, and by inhibition of NO release.
Enzyme-treated Asparagus Extract (ETAS) Enhances Memory in Normal Rats and Induces Neurite-outgrowth in PC12 Cells
Authors: Koda Tomoko , Takanari Jun , Kitadate Kentaro , Imai Hideki
Published: March 2019

Enzyme-treated asparagus extract (ETAS) contains various phytochemicals. It has been reported that ETAS protected early cognitive impairment of SAMP8 mice and Aβ-induced reduction of PC12 cell viability. In addition, ETAS had several functions on healthy people. The purpose of the present study was to investigate the effects of ETAS on normal memory function of rats and neurite-outgrowth of PC12 cells. ETAS significantly accelerated learning acquisition in in vivo and neurite-outgrowth in in vitro study. In conclusion, ETAS affected on memory function in early stage in normal rats. The basis of this effect may induce neurite-outgrowth in neurons.
Antibacterial, Antiviral, Antioxidant and Antiproliferative Activities of Thymus guyonii Essential Oil
Authors: Zeghib Assia , Kabouche Ahmed , Laggoune Souheila , Calliste Claude-Alain , Simon Alain , Bressolier Philippe , Aouni Mahjoub , Duroux Jean-Luc , Kabouche Zahia
Published: March 2019

The aerial parts of Thymus guyonii were hydrodistilled in a Clevenger type apparatus and analyzed by GC and GC-MS. 26 components were identified representing 99.8%, with carvacrol (55.6%), thymol (21.2%), o-cymene (9.7%) and δ-terpinene (5.7%) as the major components. T. guyonii essential oil exhibited a good bactericidal effect (MBC/MIC ratio = 2) against all the tested pathogenic bacteria. The essential oil lacks antiviral activity towards coxsackievirus B3 however it showed a good DPPH radical scavenging at 0.5 and 5 mg/mL test-concentrations (15.5±1.2% and 44.3±1.95%, respectively). The essential oil exhibited a proliferation inhibition of Human colorectal cell line HT-29 (30.4±3.4%) at 50 μg/mL test-concentration.
Chemoinformatic Investigation of Antibiotic Antagonism: The Interference of Thymus glabrescens Essential Oil Components with the Action of Streptomycin
Authors: Ilić Budimir S. , Miladinović Dragoljub L. , Kocić Branislava D. , Spalović Boban R. , Marković Marija S. , Čolović Hristina , Nikolić Dejan M.
Published: March 2019

Given the importance of Thymus glabrescens as a useful antibacterial remedy, we have evaluated the antibacterial and streptomycin-modifying activity of Thymus glabrescens essential oil, geraniol, geranyl acetate and thymol. It was shown that all substance-streptomycin combinations produced predominantly antagonistic interactions. Furthermore, combinations between geraniol and thymol showed dominant additive effect. Chemoinformatics results, combined with experimental data, suggest that antagonistic interactions with streptomycin were not a consequence of the antimicrobial action at the same target, but an outcome of the membrane impairment, followed by the membrane potential/proton motive force dissipation, which decreased the streptomycin uptake. Furthermore, the membrane toxicity of geraniol and thymol was confirmed by their additive antibacterial interactions and parameters of their penetration and accumulation throughout a cell membrane. This study should greatly help in an intelligent and a controlled pharmacomodulation of antibiotics.
Developing a Validated HPLC Method for the Phytochemical Analysis of Antihyperuricemic Phenylethanoid Glycosides and Flavonoids in Lippia nodiflora
Authors: Cheng Lee-Chuen , Murugaiyah Vikneswaran , Chan Kit-Lam
Published: March 2019

The phenylethanoid glycosides and flavonoids of Lippia nodiflora were reported as xanthine oxidase inhibitors that possessed antihyperuricemic effects in chemically-induced hyperuricemic rats. The present study developed a validated high performance liquid chromatography method for the simultaneous phytochemical analysis of five isolated antihyperuricemic constituents in L. nodiflora, comprising two phenylethanoid glycosides, arenarioside (1) and verbascoside (2), and three flavonoids, 6-hydroxyluteolin (3), 6-hydroxyluteolin-7- O-glycoside (4) and nodifloretin (5). These compounds were analysed at 340 nm, using gradient elution of 0.1 % aqueous acetic acid and acetonitrile. The limits of detection were 78.1 ng/mL for 3 and 39.1 ng/mL for the other compounds at a signal-to-noise ratio of 3. The limits of quantification were 312.5 ng/mL for 3 and 156.3 ng/mL for the rest at a signal-to-noise ratio of 12. The intra-day and inter-day accuracy for the five bioactive constituents were between 98.60 % and 100.97 % while their precision values were below 2.11 %. The method was then successfully applied for the quantification of 1-5 in the methanolic extract of L. nodiflora whole plant and its fractions (F1-F4), the methanolic plant part extracts (leaves, stems, roots, and flowers), and water extract of the L. nodiflora whole plant at room temperature.