bluuebunny/crossref_metadata_2025 huggingface dataset:
Angular-type Furocoumarins from the Roots of Angelica atropurpurea and their Inhibitory Activity on the NFAT Signal Transduction Pathway
Authors: Nagasawa Azumi , Sakasai Mitsuyoshi , Sakaguchi Daishi , Moriwaki Shigeru , Nishizawa Yoshinori , Kitahara Takashi
Published: March 2019

One new (1) and two known angular-type (2,3) furocoumarins, isoarchangelicin (1), archangelicin (2), and 2′-angeloyl-3′-isovaleryl vaginate (3), were isolated from the roots of Angelica atropurpurea. The structure of the new compound was established on the basis of one- and two-dimensional NMR spectra and other spectroscopic studies. The inhibitory activity of these three compounds and a deacylated form of archangelicin (4) on the nuclear factor of activated T cells (NFAT) signal transduction pathway was tested by NFAT-responsive luciferase reporter gene assay in cultured cells. Although 4 did not exhibit inhibitory activity on NFAT signaling, 1–3 exhibited dose-dependent inhibition with IC50 values of 16.5 (1), 9.0 (2), and 9.2 (3) μM.
Sawtehtetronenin from Goniothalamus sawtehii and its Cytotoxicity
Authors: Thiplueang Chiarpha , Punyanitya Sittiporn , Banjerdpongchai Ratana , Wudtiwai Benjawan , Udomputtimekakul Phansuang , Buayairaksa Mongkol , Nuntasaen Narong , Pompimon Wilart
Published: March 2019

A new acetogenin has been isolated from the ethyl acetate extract of leaves and twigs of G. sawtehii (Annonaceae). The structure of compound 1 was identified as sawtehtetronenin on the basis of spectral evidence (UV, IR, MS and 1H, and 13C NMR) and by comparison with related compounds. Sawtehtetronenin was found to be cytotoxic to human hepatocellular carcinoma HepG2 and breast cancer MDA-MB231 cells with IC50 values of 79.3+11.9 μM and 108.1+1.5 μM, respectively. Compound 1 was less toxic to both cell lines when compared with camptothecin, a chemotherapeutic drug.
Expedient Access to Enantiopure Cyclopentanic Natural Products: Total Synthesis of (-)-Cyclonerodiol
Authors: Morales Carmen Pérez , Herrador M. Mar , del Moral José F. Quílez , Barrero Alejandro F.
Published: March 2019

Following the principles of collective total synthesis, a number of natural products sharing an optically pure, multifunctional, cyclopentanic core were synthesized from a common precursor: plinol A (1). This intermediate was efficiently obtained in only four steps from (-)-linalool (2) using as the key step a Ti(III)-mediated diastereoselective radical cyclization. The feasibility of this approach was confirmed with the expedient enantiospecific synthesis of cyclonerodiol (3), and the formal synthesis of chocol G (4) and piperitone (5).
neo-Clerodane Diterpenoids from Scutellaria altissima
Authors: Bozov Petko I. , Coll Josep
Published: March 2019

Nine neo-clerodane diterpenoids, scutaltisins B-G, scupolin I, scutecolumnin C and 11- epi-scutecolumnin C have been isolated from the acetone extract of the aerial parts of Scutellaria altissima. Scutaltisins B-G are new compounds, whereas scupolin I, scutecolumnin C and 11- epi-scutecolumnin C are reported in this species for the first time.
Anthocyanins of Hibiscus sabdiffera Calyces from Sudan
Authors: Cahlíková Lucie , Ali Badreldin H. , Havlíková Lucie , Ločárek Mirek , Siatka Tomáš , Opletal Lubomír , Blunden Gerald
Published: March 2019

Extracts of the calyces of Hibiscus sabdariffa are widely used in folk medicine to combat many illnesses. The active constituents of the extracts have been shown on several occasions to be anthocyanins. In our current studies the biological activities of an extract of H. sabdariffa calyces purchased in Oman, but grown in Sudan, are being compared with those of the anthocyanins isolated from them, and, for this, the anthocyanin profile of the extract needed to be ascertained. Although several anthocyanins were detected by UHPLC-ESI-MS/MS, delphinidin-3-sambubioside (major) and cyanidin-3-sambubioside were predominant.
Phytochemical Profile of the Aerial Parts of Sedum sediforme and Anti-inflammatory Activity of Myricitrin
Authors: Winekenstädde Daniel , Angelis Apostolis , Waltenberger Birgit , Schwaiger Stefan , Tchoumtchoua Job , König Stefanie , Werz Oliver , Aligiannis Nektarios , Skaltsounis Alexios-Leandros , Stuppner Hermann
Published: March 2019

The aim of this study was to investigate the phytochemical profile of the methanol extract of the aerial parts of Sedum sediforme and to identify its secondary metabolites. By means of chromatographic separation and enrichment of compounds, HPLC-ESI-MS, HRMS, 1D-, 2D- NMR and/or comparison with reference compounds, three triterpenes, two sterols, ten flavonoids and twelve phenolic compounds were identified, together with two new compounds, i.e. (2 R*, 3 R*)-5,7-dihydroxy-2,3-dimethyl-4-chromanone-7- O-ß-D-glucoside (27) and butan-2- O-rutinoside (28). Out of the 29 identified secondary metabolites, 18 are described as ingredients of S. sediforme herein for the first time. Furthermore, myricitrin, one of the major constituents, was tested for its ability to inhibit different enzymes within the arachidonic acid cascade in order to determine its anti-inflammatory properties. Whereas there was only either weak or no inhibition of the microsomal prostaglandin E2 synthase-1 (mPGES-1) and the soluble epoxide hydrolase (sEH), myricitrin showed strong inhibition of 5-lipoxygenase (5-LO), with an IC50 of 7.8 ± 0.2 μM.
Diarylheptanoids of Curcuma comosa with Inhibitory Effects on Nitric Oxide Production in Macrophage RAW 264.7 Cells
Authors: Sornkaew Nilubon , Lin Yuan , Wang Fei , Zhang Guolin , Chokchaisiri Ratchanaporn , Zhang Ailian , Wongkrajang Kanjana , Suebsakwong Parichat , Piyachaturawat Pawinee , Suksamrarn Apichart
Published: March 2019

Eight new diarylheptanoids, a 1.2:1 mixture of (3S)- and (3 R)-1-(4-hydroxyphenyl)-7-phenyl-(4 E,6 E)-4,6-heptadien-3-ol (1a and 1b), a racemic mixture of (3S)- and (3 R)-1-(4-hydroxyphenyl)-3-methoxy-7-phenyl-(4 E,6 E)-4,6-heptadiene (2a and 2b), a ca. 1:1 mixture of (3S)- and (3 R)-1-(4-hydroxy-3-methoxyphenyl)-3-methoxy-7-phenyl)-(4 E,6 E)-4,6-heptadiene (3a and 3b), 3-acetoxy-1-(3,4-dihydroxyphenyl)-7-phenylheptan-5-ol (4), (3 R)-1-(4,5-dihydroxyphenyl)-7-phenyl-(6 E)-6-hepten-3,2′-epoxide (5), and thirteen known diarylheptanoids, 6-12, a 3:1 mixture of 13a and 13b, and 14-17, were isolated from the rhizomes of Curcuma comosa from Sakon Nakhon, northeastern part of Thailand. The isolated compounds were evaluated for their antiinflammatory activities on the inhibition of lipopolysaccharide-induced nitric oxide production in macrophage RAW 264.7 cells and the diarylheptanoids 1a and 1b mixture and 14 exhibited potent inhibitory activity.
Herbal Medicinal Products versus Botanical-Food Supplements in the European market: State of Art and Perspectives
Authors: Bilia Anna Rita
Published: March 2019

Botanical products marketed in Europe are diverse, classified as herbal medicinal products, dietary supplements, cosmetics, foods and beverages depending on the relevant applicable legislation. Many factors are taken into account in the classification of a botanical product (e.g. intended use, labeling, preparations and dosages) according to how it is placed on the market. Herbal medicinal products (HMPs) can only be sold in pharmacies, under the supervision of a pharmacist, and are marketed after full or simplified registration procedures according to their classification, i.e. as over-the-counter drugs (OTC) available without special restrictions and prescription only medicine (POM), which must be prescribed by a licensed medical practitioner. The dietary supplement segment is also sold in the market in dose form (such as capsules, tablets, ampoules of liquids, drops etc) and represents 15-20% of the botanical market at the European level with high variability among each country (i.e. in Italy it reaches up to 80%). In many cases the distinction between medicinal products and food supplements has generated borderline botanical-sourced products, which generally produce confusion and mislead the consumers. As a consequence, there is an urgent need of consumer education and in addition to collect comprehensive data and make this database systematically available to herbalists, nutritionists and medical specialists for a proper classification and harmonization of the use of botanical ingredients, and, as consequence, a correct use of these products.
Antimicrobial Activity of Nerolidol and its Derivatives against Airborne Microbes and Further Biological Activities
Authors: Krist Sabine , Banovac Daniel , Tabanca Nurhayat , Wedge David E. , Gochev Velizar K. , Wanner Jürgen , Schmidt Erich , Jirovetz Leopold
Published: March 2019

Nerolidol and its derivatives, namely cis-nerolidol, O-methyl-nerolidol, O-ethyl-nerolidol, (-)-α-bisabolol, trans, trans-farn esol and its main natural source cabreuva essential oil, were tested for their antimicrobial activity against airborne microbes and antifungal properties against plant pathogens. Among the tested compounds, α-bisabolol was the most effective antimicrobial agent and trans, trans-farnesol showed the best antifungal activity.
Mechanistic Insights to the Cytotoxicity of Amaryllidaceae Alkaloids
Authors: Nair Jerald J. , Rárová Lucie , Strnad Miroslav , Bastida Jaume , van Staden Johannes
Published: March 2019

With over 500 individual compounds, the Amaryllidaceae alkaloids represent a large and structurally diverse group of phytochemicals. Coupled to this structural diversity is the significant array of biological properties manifested by many of its members, of which their relevance in motor neuron disease and cancer chemotherapy has attracted considerable attention. To this extent, galanthamine has evolved into a successful commercial drug for Alzheimer's disease since its approval by the FDA in 2001. Concurrently, there have been several positive indicators for the emergence of an anticancer drug from the Amaryllidaceae due to the potency of several of its representatives as cell line specific antiproliferative agents. In this regard, the phenanthridones such as pancratistatin and narciclasine have offered most promise since their advancement into clinical trials, following which there has been renewed interest in the cytotoxic properties of these alkaloids. Given this background, this review seeks to highlight the various mechanisms which have been invoked to corroborate the cytotoxic effects of Amaryllidaceae alkaloids.
Sponge Derived Bromotyrosines: Structural Diversity through Natural Combinatorial Chemistry
Authors: Niemann Hendrik , Marmann Andreas , Lin Wenhan , Proksch Peter
Published: March 2019

Sponge derived bromotyrosines are a multifaceted class of marine bioactive compounds that are important for the chemical defense of sponges but also for drug discovery programs as well as for technical applications in the field of antifouling constituents. These compounds, which are mainly accumulated by Verongid sponges, exhibit a diverse range of bioactivities including antibiotic, cytotoxic and antifouling effects. In spite of the simple biogenetic building blocks, which consist only of brominated tyrosine and tyramine units, an impressive diversity of different compounds is obtained through different linkages between these precursors and through structural modifications of the side chains and/or aromatic rings resembling strategies that are known from combinatorial chemistry. As examples for bioactive, structurally divergent bromotyrosines psammaplin A, Aplysina alkaloids featuring aerothionin, aeroplysinin-1 and the dienone, and the bastadins, including the synthetically derived hemibastadin congeners, have been selected for this review. Whereas all of these natural products are believed to be involved in the chemical defense of sponges, some of them may also be of particular relevance to drug discovery due to their interaction with specific molecular targets in eukaryotic cells. These targets involve important enzymes and receptors, such as histone deacetylases (HDAC) and DNA methyltransferases (DNMT), which are inhibited by psammaplin A, as well as ryanodine receptors that are targeted by bastadine type compounds. The hemibastadins such as the synthetically derived dibromohemibastadin are of particular interest due to their antifouling activity. For the latter, a phenoloxidase which catalyzes the bioglue formation needed for firm attachment of fouling organisms to a given substrate was identified as a molecular target. The Aplysina alkaloids finally provide a vivid example for dynamic wound induced bioconversions of natural products that generate highly efficient chemical weapons precisely when and where needed.
Preparation and Characterization of Colon-Targeted Particles of Pulsatilla chinensis Saponins
Authors: Chen Zhenhua , Guan Yongmei , Zhou Leilei , Xu Ying , Yang Ming , Liu Hongning
Published: March 2019

Pulsatilla chinensis (Bunge) Regel is a traditional Chinese medicine used to treat ulcerative colitis. This study prepared and characterized colon-targeted particles of P. chinensis saponins by particle design. Most of the P. chinensis saponins in the composite particles were coated with Eudragit S100, as seen in SEM micrographs; meanwhile, the characteristic diffraction peaks in X-RD, surface wettability, and particle size distribution of the composite particles were basically the same as those of Eudragit S100. These results suggested that the mechanochemical process could be used to prepare colon-targeted particles with core-shell structures with the drug coated by the excipient; the results also showed similar surface characteristics in the coating.
Proanthocyanidin from Grape Seed Extract Inhibits Airway Inflammation and Remodeling in a Murine Model of Chronic Asthma
Authors: Zhou Dan-Yang , Fang Su-Rong , Zou Chun-Fang , Zhang Qian , Gu Wei
Published: March 2019

Asthma is characterized by airway inflammation and airway remodeling. Our previous study revealed that grape seed proanthocyanidin extract (GSPE) could inhibit asthmatic airway inflammation and airway hyper-responsiveness by down-regulation of inducible nitric oxide synthase in a murine model of acute asthma. The present study aimed to evaluate GSPE's effects on airway inflammation and airway remodeling in a chronic asthmatic model. BALB/c mice were sensitized with ovalbumin (OVA) and then were challenged three times a week for 8 weeks. Airway responsiveness was measured at 24 h after the last OVA challenge. HE staining, PAS staining, and Masson staining were used to observe any airway inflammation in the lung tissue, airway mucus secretion, and subepithelial fibrosis, respectively. The cytokines levels in the lavage fluid (BALF) in addition to the total serum immunoglobulin E (IgE) levels were detected by ELISA. Furthermore, lung collagen contents, α-smooth muscle actin (α-SMA), and transforming growth factor-β1 (TGF-β1) expression in the airway were assessed by hydroxyproline assay, immunohistochemistry, andWestern blot analysis, respectively. GSPE administration significantly suppressed airway resistance as well as reduced the amount of inflammatory cells, especially the eosinophil count, in BALF. Additionally, the GSPE treatment markedly decreased interleukin (IL)-4, IL-13, and vascular endothelial growth factor (VEGF) levels in BALF in addition to the total serum IgE levels. A histological examination demonstrated that GSPE significantly ameliorated allergen-induced lung eosinophilic inflammation and decreased PAS-positive epithelial cells in the airway. The elevated hydroxyproline contents, lung α-SMA contents, and TGF-β1 protein expression that were observed in the OVA mice were also inhibited by GSPE. In conclusion, GSPE could inhibit airway inflammation and airway remodeling in a murine model of chronic asthma, thus providing a potential treatment for asthma.
Isolation and Identification of a Polygalacturonase Inhibiting Protein from Isatidis root
Authors: Gao Guanzhen , Wang Qian , Zhou Jianwu , Wang Huiqin , Ke Lijing , Rao Pingfan
Published: March 2019

Isatis indigotica Fort. (Chinese woad) has been widely used as a dye- and medicinal-plant in traditional Chinese medicine. Although I. indigotica has been cultivated in various regions across China in recent years, its innate immunity is little known. In this study, a protein with MW 37.5 kDa was purified from the extract of fresh Isatidis roots by SP-5PW cationic exchange and POROS HP2 hydrophobic interaction chromatography. The N-terminal amino acid sequence of the purified protein was subsequently determined as T-D-L-C-H-K-D-P-K-N-T-L-L by Edman degradation. The N-terminal sequence and PG inhibitory activity identified the purified substance as a polygalacturonase inhibiting protein. This purified Isatidis PGIP with a specific activity of 7.64×104 U/mg showed strong inhibitory activity against 160 U of Aspergillus niger polygalacturonase. Compared with PGIPs from guava and bean pods, Isatidis PGIP showed very poor pH and heat stabilities, which may represent the different need of plant innate immunity between plant underground and aboveground organs.
Synthesis and Antihyperlipidemic Activity of Piperic Acid Derivatives
Authors: Rong A , Bao Narisu , Sun Zhaorigetu , Borjihan Gereltu , Qiao Yanjiang , Jin Zhuang
Published: March 2019

A series of piperic acid derivatives were designed and synthesized from piperine/ piperlonguminine, and their antihyperlipidemic activities evaluated in diet-induced hyperlipidemic rats with respect to simvastatin. Two promising analogues 3 and 10 were discovered and their antihyperlipidemic activities were comparable to or better than those of simvastatin.
A New Benzylisoquinoline Alkaloid from Leontice altaica
Authors: Jenis Janar , Nugroho Alfarius Eko , Hashimoto Akiyo , Deguchi Jun , Hirasawa Yusuke , Wong Chin Piow , Kaneda Toshio , Shirota Osamu , Morita Hiroshi
Published: March 2019

A new benzylisoquinoline alkaloid, lincangenine-4- β -D-glucopyranoside (1), has been isolated from the roots of Leontice altaica, together with 5 known alkaloids. Its structure was elucidated on the basis of D and 2D NMR data, and chemical means.
A New Geranylbenzofuranone from Zanthoxylum armatum
Authors: Bhatt Vinod , Kumar Vishal , Singh Bikram , Kumar Neeraj
Published: March 2019

A new geranylbenzofuranone, zantholide (1), and eight known compounds, dodeca-2 E,4 E-dienoic acid isobutylamide (2), dodeca-2 E,4 E,8 Z,11-tetraenoic acid isobutyl amide (3), zanthoxylin (4), sesamin (5), kobusin (6), asarinin (7), fargesin (8) and armatamide (9), have been isolated from the bark of Zanthoxylum armatum. The structures of the isolated compounds were determined on the basis of spectroscopic (1D, 2D NMR) and HR-ESI-MS data. This is the first report on the isolation of 2 and 3 from the Rutaceae family and 4 from Z. armatum.
Phenolic Compounds from Limonium pruinosum
Authors: Boudermine Sihem , Malafronte Nicola , Mencherini Teresa , Esposito Tiziana , Aquino Rita Patrizia , Beghidja Noureddine , Benayache Samir , D'Ambola Massimiliano , Vassallo Antonio
Published: March 2019

A new phenolic compound, 6′- O-sulfonyl-salidroside (1), together with fifteen known compounds, were isolated from the all parts of Limonium pruinosum. Their structures were elucidated by 1D and 2D NMR experiments including 1D TOCSY, DQF-COSY, HSQC and HMBC spectroscopy, as well as ESIMS analysis. The antioxidant activity of the extracts and all isolated compounds was evaluated by DPPH test.
Comparison of Different Methodologies for Detailed Screening of Taraxacum officinale Honey Volatiles
Authors: Jerković Igor , Marijanović Zvonimir , Kranjac Marina , Radonić Ani
Published: March 2019

Headspace solid-phase microextraction (HS-SPME), ultrasonic solvent extraction (USE) and solid phase extraction (SPE), followed by GC-FID/MS were used for screening of dandelion ( Taraxacum officinale Weber) honey headspace, volatiles and semi-volatiles. The obtained results constitute a breakthrough towards screening of dandelion honey since dominant compounds identified in the extracts were not previously reported for this honey type. Nitriles dominated in the headspace, particularly 3-methylpentanenitrile (up to 29.9%) and phenylacetonitrile (up to 20.9%). Lower methyl branched aliphatic acids and norisoprenoids were relevant minor constituents of the headspace. The extracts contained phenylacetic acid (up to 24.0%) and dehydrovomifoliol (up to 19.3%) as predominant compounds, while 3-methylpentanenitrile and phenylacetonitrile were detected in the extracts in minor abundance. Dehydrovomifoliol can be considered more characteristic for dandelion honey in distinction from phenylacetic acid. Low molecular aliphatic acids, benzene derivatives and an array of higher aliphatic compounds were also found in the extracts. The results of SPE/GC-FID/MS were very similar to USE/GC-FID/MS with the solvent dichloromethane. The use of all applied methodologies was relevant for the comprehensive chemical fingerprinting of dandelion honey volatiles.
Volatile Constituents from the Leaves, Fruits (Berries), Stems and Roots of Solanum xanthocarpum from Nepal
Authors: Satyal Prabodh , Maharjan Samjhana , Setzer William N.
Published: March 2019

The essential oils from the leaves, fruits, roots, and stems of Solanum xanthocarpum, growing wild in Nepal, have been obtained and analyzed by gas chromatography – mass spectrometry. The fruit volatiles were dominated by benzyl benzoate (21.7%) and ( E, E)-geranyl linalool (12.6%); heptacosane (20.0%) was the major component of the leaf oil; the stem oil was dominated by palmitic acid (28.9%), heptacosane (12.8%) and linoleic acid (10.1%); while solavetivone (22.9%), palmitic acid (21.0%), and linoleic acid (8.2%) were the major components of the root essential oil. There do not seem to be any common phytochemical taxonomic markers in the essential oils of Solanum spp; the chemical diversity observed in this genus mirrors the taxonomic diversity.
Flavone C-Glucosides Responsible for Yellow Pigmentation Induced by Low Temperature in Bracts of Zantedeschia aethiopica
Authors: Nakayama Masayoshi , Koshioka Masaji , Kondo Tadao , Imizu Kiyotoshi
Published: March 2019

We aimed to identify the main compounds responsible for low temperature-induced yellow pigmentation of the bracts of Zantedeschia aethiopica ‘Wedding March’. On the basis of the area ratios estimated from absorbance at 400 nm in HPLC analyses, we identified two flavonoids, isoorientin and swertiajaponin, as such compounds. We also identified two additional flavonoids, isovitexin and swertisin, which do not contribute considerably to the yellow pigmentation. Flavonoids of Zantedeschia bracts seem to belong to the class of flavone C-glycosides.
Evaluation of Antioxidant Activity, and Quantitative Estimation of Flavonoids, Saponins and Phenols in Crude Extract and Dry Fractions of Medicago lupulina Aerial Parts
Authors: Kicel Agnieszka , Olszewska Monika Anna
Published: March 2019

This study was designed to evaluate the flavonoid, saponin (TSC) and phenolic (TPC) contents and in vitro antioxidant activity of the crude (CME) and dry extracts and fractions of Medicago lupulina L. aerial parts. A validated RP-HPLC method led to quantitation of flavonols (kaempferol, quercetin and myricetin) and flavones (apigenin and luteolin) in the hydrolyzed extract. TSC and TPC were assayed spectrophotometrically at 560 and 760 nm, respectively. The antioxidant activity of the CME and the dry fractions were followed in vitro by DPPH free radical and ferric reducing antioxidant power (FRAP) methods. The flavonoid content of CME was 1.27 mg/g dw. The prevailing flavonoids were luteolin and myricetin, at concentrations of 0.37 and 0.36 mg/g dw, respectively. TSC and TPC were detected in CME at the level of 90.4 mg ESE/g dw, and 12.9 mg GAE/g dw, respectively. In the DPPH and FRAP tests, the CME exhibited antioxidant capacity with TEAA and FRAP values of 45.4 μmol Trolox®/g dw and 0.2 mmol Fe2+/g dw, respectively. The diethyl ether dry fraction was the most valuable one, showing the highest antioxidant activity (TEAA = 726.1 μmol Trolox®/g dw, FRAP = 2349.4 μmol Fe2+/g dw) that was in accordance with its high TPC (162.4 mg/g dw).
Effects of Ursolic Acid on Contractile Activity of Gastric Smooth Muscles
Authors: Prissadova Natalia , Bozov Petko , Marinkov Kiril , Badakov Hristo , Kristev Atanas
Published: March 2019

Ursolic acid (UA) in concentrations of 1×10−7 mol/L - 5×10−5 mol/L induced relaxation in gastric smooth muscle (SM) tissues, in a concentration-dependent manner. The relaxation did not change membrane potential and slow wave contraction patterns. A significant decrease in amplitude and frequency of spike-potentials was observed. UA-induced reactivity was removed when SM preparations were treated with nifedipine (1×10−6 mol/L). Ca2+- induced contractions of the depolarized SM preparations (42 mmol/L K+; Ca2+- free Krebs solution) were substantially reduced in the presence of UA. It was determined that, in certain concentrations, UA influenced L – type Ca2+ channels, and reduced the Ca2+ influx.
Evaluation of the Anti-inflammatory and Antioxidative Potential of Four Fern Species from China Intended for Use as Food Supplements
Authors: Dion Carine , Haug Christian , Guan Haifeng , Ripoll Christophe , Spiteller Peter , Coussaert Aurelie , Boulet Elodie , Schmidt Daniel , Wei Jianbing , Zhou Yijun , Lamottke Kai
Published: March 2019

Inflammation plays a major role in many diseases, for instance in arteriosclerosis, rheumatoid arthritis, autoimmune disorders and cancer. Since many plants contain compounds with anti-inflammatory activity, their consumption may be able to prevent the development of inflammatory-based diseases. Edible ferns are some of the most important wild vegetables in China and have traditionally been used both for dietary and therapeutic purposes. In this study we investigated the anti-inflammatory and antioxidant potential of fern extracts from Matteucca struthiopteris, Osmunda japonica, Matteuccia oriental and Pteridium aquilinum intended for use as nutraceuticals. Two modes of action were investigated: the inhibition of the pro-inflammatory gene expression of interleukin-1 beta (IL1-β) and interleukin-6 (IL6), and the gene expression of iNOS by LPS-elicited macrophages. The results showed a decrease of IL1-β gene expression for the five fern extracts. This effect was more pronounced for the extracts prepared from the roots of O. japonica (IC50 of 17.8 μg/mL) and the young fronds of M. orientalis (50.0 μg/mL). Regarding the indirect measurement of NO, via iNOS gene expression, an interesting decrease of 50% was obtained with the extract of M. orientalis fronds at a low concentration (20 μg/mL) compared with P. aquilinum fronds (160 μg/mL) and leaves of O. japonica. The latter showed a higher decrease but at a high concentration of extract (160 μg/mL). The five fern extracts were also evaluated for their ability to scavenge 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS). All fern extracts exhibited antioxidant effects but the roots of O. japonica and the fronds of M. orientalis were most efficient. The HPLC-MS analysis of the constituents of the fern extracts confirmed the presence of chlorogenic acid, caffeic acid, p-coumaric acid, ferulic acid, kaempferol and apigenin, molecules known to exhibit antiinflammatory and/or antioxidant properties.
Two Chlorinated Benzofuran Derivatives from the Marine Fungus Pseudallescheria boydii
Authors: Yan Dan-Feng , Lan Wen-Jian , Wang Kun-Teng , Huang Lei , Jiang Cai-Wu , Li Hou-Jin
Published: March 2019

The marine fungus Pseudallescheria boydii was isolated from the inner tissue of the starfish Acanthaster planci. This fungus was cultured in a high salinity glucose-peptone-yeast extract (GPY) medium. Two new chlorinated benzofuran derivatives, 6-chloro-2-(2-hydroxypropan-2-yl)–2,3-dihydro-5-hydroxybenzofuran (1) and 7-chloro-2-(2-hydroxypropan-2-yl)–2,3-dihydro-5-hydroxybenzofuran (2), were obtained from the extract of the culture broth. Their structures were determined by analysis of the NMR and MS data.
Caffeic Acid: Potential Applications in Nanotechnology as a Green Reducing Agent for Sustainable Synthesis of Gold Nanoparticles
Authors: Seo Yu Seon , Cha Song-Hyun , Cho Seonho , Yoon Hye-Ran , Kang Young-Hwa , Park Youmie
Published: March 2019

The sustainable synthesis of gold nanoparticles from gold ions was conducted with caffeic acid as a green reducing agent. The formation of gold nanoparticles was confirmed by spectroscopic and microscopic methods. Spherical nanoparticles with an average diameter of 29.99 ± 7.43 nm were observed in high-resolution transmission electron microscopy and atomic force microscopy images. The newly prepared gold nanoparticles exhibited catalytic activity toward the reduction of 4-nitrophenol to 4-aminophenol in the presence of sodium borohydride. This system enables the preparation of green catalysts using plant natural products as reducing agents, which fulfills the growing need for sustainability initiatives.
Chemical Constituents and Derivatization of Melodorinol from the Roots of Melodorum fruticosum
Authors: Hongnak Siriwat , Jongaramruong Jongkolnee , Khumkratok Suttira , Siriphong Pongpun , Tip-pyang Santi
Published: March 2019

Chemical investigation of the CH2Cl2 and MeOH crude extracts of the roots of Melodorum fruticosum Lour. led to the isolation of 15 known compounds, of which 5, 10, and 12-15 are reported for the first time from this plant. In addition, melodorinol (7) was derivatized to afford six new (7a-7d and 7f-7g) analogues and one known compound (7e). Their structures were identified on the basic of spectroscopic data. Most of them were evaluated for their cytotoxicity against KB, HeLa, MCF-7 and HepG-2 cell lines. Compounds 4 and 7b were the most potent to all cell lines.
Chemical Composition and Antibacterial Activity of the Essential Oil of Ruilopezia bracteosa
Authors: Alarcón Libia , Peña Alexis , Velasco Judith , Baptista José Gregorio , Rojas Luis , Aparicio Rosa , Usubillaga Alfredo
Published: March 2019

The essential oil from the leaves of Ruilopezia bracteosa was obtained by hydrodistillation, and analyzed by GC-MS. Eighteen components, which made up 99.6% of the oil were identified, the most abundant being β-myrcene (34.2%), α-pinene (24.3%), 7-epi-α-selinene (9.1%), β-pinene (8.5%) and 6,9-guaiadiene (4.4%). Antibacterial activity was tested against Gram-positive and Gram-negative bacteria using broth microdilution and disk agar diffusion methods. MIC values found presented significant differences between both methods, which may be due to diffusion factors.
Momilactone Sensitive Proteins in Arabidopsis thaliana
Authors: Kato-Noguchi Hisashi , Kitajima Shinya
Published: March 2019

The labdane-related diterpenoid, momilactone B has potent growth inhibitory activity and was demonstrated to play a particularly critical role in the allelopathy of rice ( Oryza sativa L.). However, there is limited information available about the mode of action of momilactone B on the growth inhibition. The present research describes the effects of momilactone B on protein expression in the early development of Arabidopsis thaliana seedling, which was determined by two-dimensional electrophoresis and MALDI-TOFMS. Momilactone B inhibited the accumulation of subtilisin-like serine protease, amyrin synthase LUP2, β-glucosidase and malate synthase at 1 h after the momilactone application. Those proteins are involved in the metabolic turnover and the production of intermediates needed for cell structures resulting in plant growth and development. Momilactone B also inhibited the breakdown of cruciferin 2, which is essential for seed germination and seedling growth to construct cell structures. Momilactone B induced the accumulation of translationally controlled tumor protein, glutathione S-transferase and 1-cysteine peroxiredoxin 1. These proteins are involved in stress responses and increased stress tolerance. In addition, glutathione S-transferase has the activity of herbicide detoxification and 1-cysteine peroxiredoxin 1 has inhibitory activity for seed germination under unfavorable conditions. The present research suggests that momilactone B may inhibit the seedling growth by the inhibition of the metabolic turnover and the production of intermediates for cell structures. In addition, momilactone induced proteins associated with plant defense responses.
Short Term Effect of Caffeine on Purine, Pyrimidine and Pyridine Metabolism in Rice (Oryza sativa) Seedlings
Authors: Deng Wei-Wei , Katahira Riko , Ashihara Hiroshi
Published: March 2019

As part of our studies on the physiological and ecological function of caffeine, we investigated the effect of exogenously supplied caffeine on purine, pyrimidine and pyridine metabolism in rice seedlings. We examined the effect of 1 mM caffeine on the in situ metabolism of 14C-labelled adenine, guanine, inosine, uridine, uracil, nicotinamide and nicotinic acid. The segments of 4-day-old dark-grown seedlings were incubated with these labelled compounds for 6 h. For purines, the incorporation of radioactivity from [8-14C]adenine and [8-14C]guanine into nucleotides was enhanced by caffeine; in contrast, incorporation into CO2 were reduced. The radioactivity in ureides (allantoin and allantoic acid) from [8-14C]guanine and [8-14C]inosine was increased by caffeine. For pyrimidines, caffeine enhanced the incorporation of radioactivity from [2-14C]uridine into nucleotides, which was accompanied by a decrease in pyrimidine catabolism. Such difference was not found in the metabolism of [2-14C]uracil. Caffeine did not influence the pyridine metabolism of [carbonyl-14C]-nicotinamide and [2-14C]nicotinic acid. The possible control steps of caffeine on nucleotide metabolism in rice are discussed.
Phytotoxic Substance with Allelopathic Activity in Brachiaria decumbens
Authors: Kobayashi Ai , Kato-Noguchi Hisashi
Published: March 2019

The grass Brachiaria decumbens becomes naturalized and quickly dominant in non-native areas. It was hypothesized that phytotoxic substances of plants may contribute to the domination and invasion of the plants. However, no potent phytotoxic substance has been reported in B decumbens. Therefore, we searched for phytotoxic substances with allelopathic activity in this species. An acpeous methanol extract of B. decumbens inhibited the growth of roots and shoots of cress (Lepidium sativum), lettuce (Lactuca sativa), timothy (Phleum pratense) and ryegrass ilolium multiflorum) seedlings. The extract was then purified using chromatographic methods and a phytotoxic substance with allelopathic activity was isolated and identified by spectral analysis as ( 6R,9S)-3-oxo-α-ionol. These results suggest that this compound may contribute to the allelopathic effect caused by the B. decumbens extract and may be in part responsible for the invasion and domination of B. decumbens. Two other Brachiaria species, B. brizantha and a Bractearia hybrid were also confirmed to contain ( 6R,9S)-3-oxo-α-ionol. Therefore, this compound may play an important role in the phytotoxicity of the Brachiaria species.
Angelicin as the Principal Allelochemical in Heracleum sosnowskyi Fruit
Authors: Mishyna Maryia , Laman Nikolai , Prokhorov Valery , Fujii Yoshiharu
Published: March 2019

Distribution patterns of furocoumarins in fruits of the invasive species Heracleum sosnowskyi Manden. (Sosnowskyi's hogweed) during a cold stratification period were investigated. Angelicin, bergapten, methoxalen and imperatorin were mainly localized in the fruit coats and their content varied depending on the fruit source. Cold stratification treatment (90 days, 2–3°C) reduced the content of furocoumarins in the fruit coats by more than two times, compared with those before stratification. The specific activity of the detected furocoumarins and total activity of crude extracts were evaluated using Lactuca sativa, as acceptor plant. Crude extracts obtained from fruit coats and seeds of H. sosnowskyi suppressed 50% of radicle and hypocotyl growth of lettuce seedlings at the concentration range of 1.0–1.7 mg/mL. The inhibitory activity of angelicin was proved to be the highest compared with the other tested furocoumarins, and the inhibitory activity of crude extracts could be explained mainly by the presence of angelicin. Both, monocots ( Lolium multiflorum, Phleum pratensis, Festuca pratesis, Lolium perenne) and dicots ( Tripholium repens, Trifolium pretense) were found to be sensitive to the exudates of whole H. sosnowskyi fruits. Thus, we assume, that high inhibitory potential of furocoumarins, especially angelicin, at high seed productivity of H. sosnowskyi might have an ecological significance in plant-plant interaction.
The Biosynthetic Activities of Primary and Secondary Metabolites in Suspension Cultures of Aquilaria microcarpa
Authors: Ogita Shinjiro , Lee Jung-Bum , Kurosaki Fumiya , Kato Yasuo
Published: March 2019

Two types of suspension-cultured Aquilaria microcarpa cells, friable and aggregated, were selectively generated. The biosynthetic activities of primary and secondary metabolites in target cells were detected using laser scanning microscopy (LSM) imaging with diphenylboric acid 2-amino ethyl ester (DPBA) and 9-diethylamino-5H-benzo[alpha]phenoxazine-5-one (Nile red) staining. Scanned friable cells produced weakly fluorescent images revealing low productivity of metabolites. On the other hand, scanning of aggregated cells produced clear fluorescent images depicting the accumulations of flavonoids and lipids. Furthermore, abundant deposition of an unknown resinous compound in extracellular portion of aggregated cells could be visualized. The resinous compound was white to whitish-gray in color and highly sedimented in the medium. Based on these observations, we focused our investigation of metabolite productivity on aggregated suspension cells. Some prominent extracellular compounds were detected in the used liquid medium, as well as in the resinous residue within the medium. The characteristics of these metabolites were investigated in detail via gas chromatography-mass spectrometry (GC-MS) analysis.
Constituents of Ligularia brassicoides Collected in China: A New Diels-Alder Adduct of Eremophilan-10βol and Methacrylic Acid
Authors: Taniguchi Mizuho , Nakashima Katsuyuki , Okamoto Yasuko , Gong Xun , Kuroda Chiaki , Tori Motoo
Published: March 2019

Chemical study of four samples of Ligularia brassicoides collected in Sichuan Province of China afforded 18 compounds, five of which were new. LC-MS profiles were somehow similar to each other, although the compound ratio was slightly different. One of the new compound was a Diels-Alder adduct between franoeremophilan-10β-ol and methacrylic acid.
Antiproliferative Activity of seco-Oxacassanes from Acacia schaffneri
Authors: Torres-Valencia J. Martín , Motilva Virginia , Manríquez-Torres J. Jesús , García-Mauriño Sofía , López-Lázaro Miguel , Zbakh Hanaa , Calderón-Montaño José M. , Gómez-Hurtado Mario A. , Gayosso-De-Lucio Juan A. , Cerda-García-Rojas Carlos M. , Joseph-Nathan Pedro
Published: March 2019

This work reports the antiproliferative activity of seco-oxacassanes 1–3, isolated from Acacia schaffneri, against human colon (HT-29), lung (A-549), and melanoma (UACC-62) cancer cell lines, as well as against their non-malignant counterparts CCD-841 CoN, MRC-5, and VH-10, respectively, using the sulforhodamine B test. While compounds 1 and 3 were inactive, 2 presented strong activity with IC50 values between 0.12 and 0.92 μg mL–1. The cytotoxicity mechanisms of 2 were investigated by cell cycle analysis and through DNA repair pathways, indicating that the compound is capable of arresting the cell cycle in the G0/G1 phase. This effect might be generated through damage to DNA by alkylation. In addition, compound 2 was able to decrease HT-29 migration.
Chemical Constituents of Lecythis pisonis (Lecythidaceae) – A New Saponin and Complete 1H and 13C Chemical Shift Assignments
Authors: Duarte Rennê C. , Matos Carlos R. R. , Braz-Filho Raimundo , Mathias Leda
Published: March 2019

A novel triterpenoid saponin 3- O-β-D-glucuronopyranosyl-(1→3)-2α,19α-dihydroxyolean-12-en-28-oic acid [3- O-β-D-glucuronopyranosyl-(1′→3)-arjunic acid, 1], ten known compounds [six triterpenoids: α-amyrin (2), β-amyrin (3), germanicol (4), lupeol (5), friedelin (6), friedelanol (7); four steroids -campesterol (8), stigmasterol (9), sitosterol (10), cholesterol (11)], and a long chain alcohol n-eicosan-1-ol (12) were identified in the bark of Lecythis pisonis. The structures were established by 1D and 2D NMR spectroscopy (1H and 13C-NMR, DEPTQ, 1H-1H-COSY, NOESY, HSQC and HMBC), low (CG-MS) and high resolution mass spectrometry (HR-ESI-MS), and infrared (IR) spectral data involving comparison with the literature.
Cucumarioside E from the Far Eastern Sea Cucumber Cucumaria japonica (Cucumariidae, Dendrochirotida), New Minor Monosulfated Holostane Triterpene Pentaoside with Glucose as the Second Monosaccharide Residue
Authors: Silchenko Alexandra S. , Kalinovsky Anatoly I. , Dmitrenok Pavel S. , Kalinin Vladimir I. , Mazeika Andrey N. , Vorobieva Natalia S. , Sanina Nina M. , Kostetsky Edward Y.
Published: March 2019

New minor triterpene glycoside, cucumarioside E (1) has been isolated from the Far Eastern sea cucumber Cucumaria japonica. The structure of the glycoside was elucidated by 2D-NMR specroscopy and mass-spectrometry. The glycoside has glucose instead of quinovose as the second monosaccharide residue and xylose as third monosaccharide residue that is unique structural feature for triterpene glycosides carbohydrate chains from sea cucumbers belonging to the genus Cucumaria.
Two New Secondary Metabolites from Tephrosia purpurea
Authors: Chen Yin-Ning , Peng Yan , Gao Cheng-Hai , Yan Tao , Xu Zhi-Fang , Qiu Samuel X. , Cao Wen-Hao , Deng Ligao , Huang Ri-Ming
Published: March 2019

Further investigation of Tephrosia purpurea led to the isolation of a new prenylated flavone, isoglabratephrin B (1) and a new 1,2-ethanedione benzofuran derivative, purpdione B (2). The structures of the new isolates were elucidated on the basis of extensive spectroscopic analysis.
Anti-austeritic Constituents of the Congolese Medicinal Plant Aframomum melegueta
Authors: Dibwe Dya Fita , Awale Suresh , Morita Hiroyuki , Tezuka Yasuhiro
Published: March 2019

In the course of our search for anticancer agents based on a novel anti-austerity strategy, we found that the CHCl3 extract of the roots of Aflamomum melegueta (Zingiberaceae), collected in the Democratic Republic of Congo, killed PANC-1 human pancreatic cancer cells preferentially in nutrient-deprived medium (NDM). Phytochemical investigation of the CHCl3 extract led to the isolation of seven known compounds [(-)-buplerol (1), (-)-arctigenin (2), ( E)-14-hydroxy-15-norlabda-8(17),12-dien-16-al (3), labda-8(17),12-dien-15,16-dial (4), 16-oxo-8(17),12( E)-labdadien-15-oic acid (5), 5-hydroxy-7-methoxyflavone (6), and apigenin (7)]. In addition to the previously reported preferentially cytotoxic compound, (-)-arctigenin (2, PC50 0.5 μM), (-)-buplerol (1) also displayed potent preferential cytotoxicity with a PC50 value of 8.42 pM and triggered apoptosis-like PANC-1 cell death in NDM.
A New Aromatic Compound from the Stem Bark of Terminalia catappa
Authors: Pertuit David , Mitaine-Offer Anne-Claire , Miyamoto Tomofumi , Tanaka Chiaki , Delemasure Stéphanie , Dutartre Patrick , Lacaille-Dubois Marie-Aleth
Published: March 2019

A new aromatic compound 3,4,5-trimethoxyphenyl-1- O-(4-sulfo)-β-D-glucopyranoside (1), in addition to two triterpenoid saponins (chebuloside II, arjunoglucoside II), two triterpenes (arjunolic acid and 3-betulinic acid) and sitosterol-3- O-β-D-glucopyranoside have been isolated from the barks of Terminalia catappa. Their structures have been established on the basis of spectroscopic techniques (1D/2D NMR) and MS. Their cytotoxicity and anti-inflammatory activity, together with the antioxidant capacity of compound 1 were also evaluated.
Synthesis of ε-Viniferin Glycosides by Glucosyltransferase from Phytolacca americana and their Inhibitory Activity on Histamine Release from Rat Peritoneal Mast Cells
Authors: Hamada Hiroki , Hamada Hatsuyuki , Shimoda Kei
Published: March 2019

Glycosylation of (+)-ε-viniferin was investigated using glucosyltransferase from Phytolacca americana ( PaGT3) as a biocatalyst. (+)-ε-Viniferin was converted by PaGT3 into its 4b- and 13b-β-D-glucosides, the inhibitory activities on histamine release from rat peritoneal mast cells of which were higher than that of (+)-ε-viniferin.
Long-chain Glucosinolates from Arabis turrita: Enzymatic and Non-enzymatic Degradations
Authors: Blažević Ivica , Montaut Sabine , Nicola Gina Rosalinda De , Rollin Patrick
Published: March 2019

C8-C10 methylsulfinylalkyl glucosinolates (GLs), and C8-C10 methylsulfonylalkyl GLs were identified in the seed of Arabis turrita L. by HPLC-MS/ESI analysis of intact GLs. Enzymatic (with myrosinase) and non-enzymatic (thermal at 100°C, and chemical at different pH) hydrolyses were performed and the volatile isolates were analyzed by GC-MS. Only the enzymatic and chemical (pH 10) degradations produced volatiles which are originating from GL degradation. GC-MS analysis showed the presence of long-chain olefinic isothiocyanates (ITCs) along with other the long-chain thiofunctionalized GL breakdown products.
Terpenoids Preserved in Fossils from Miocene-aged Japanese Conifer Wood
Authors: Ludwiczuk Agnieszka , Asakawa Yoshinori
Published: March 2019

The compositions of terpenoids from the solvent extracts of two silicified wood samples were analyzed using a GC/MS method. Chromatographic analysis showed that several biomolecules were preserved unaltered in the Miocene-aged Japanese wood. These were α-terpineol, α-cedrene, thujopsene, widdrol and ferruginol, among others. In addition to the bioterpenoids, the fossil woods contained a series of geoterpenoids that were generated from their biological precursors before and after burial. These were cadalene, daucalene, pseudowiddrene and cuparene. The chemical composition of both analyzed fossil samples suggest that the silicified woods collected in the Noto Peninsula belong to the Cupressaceae family; this was confirmed by morphological analysis. Both samples were identified as Taxodioxylon cunninghamioides, which is the most common Miocene wood in Japan.
Can Ozone Alter the Terpenoid Composition and Membrane Integrity of in vitro Melissa officinalis Shoots?
Authors: D'Angiolillo Francesca , Tonelli Mariagrazia , Pellegrini Elisa , Nali Cristina , Lorenzini Giacomo , Pistelli Luisa , Pistelli Laura
Published: March 2019

Ozone affects volatile organic compounds that protect plants from biotic and abiotic stress. In vitro Melissa officinalis shoots were exposed to ozone (200 ppb, 3 h) in controlled environmental conditions: leaf pigments, membrane integrity and headspace composition were assayed during fumigation and after the recovery period (3 h from the beginning of the exposure, FBE). At the end of the exposure, no injury was observed in untreated and treated shoots, although an evident increase in lipid peroxidation was reported (+38.5 and +37.2% of TBARS levels in comparison with controls, respectively after 1 and 3 h FBE). The levels of total carotenoids significantly rose as a normal response mechanism to oxidative stress. SPME-GS-MS analysis showed that, as a consequence of the fumigation, the trends in non-terpenoid compounds increased after 1 and 3 h FBE. This suggests that the concentration and the duration of the treatment were enough to cause a breakdown of cells (as evidenced by increased TBARS levels) and involves an association between volatile products of the lipoxygenase pathway (LOX products) and membrane degradation.