bluuebunny/crossref_metadata_2025 huggingface dataset:
Trigonelline (N-methylnicotinic acid) Biosynthesis and its Biological Role in Plants
Authors: Ashihara Hiroshi
Published: March 2019

Trigonelline is synthesized from nicotinic acid in many plant species. This compound accumulates in seeds of leguminous plants and Coffea sp. The present article reviews the distribution of nicotinic acid conjugates and biosynthetic pathways of trigonelline, including the pyridine nucleotide cycle and de novo synthesis. The function of trigonelline in plants is also discussed.
A View on the Active Site of Firefly Luciferase
Authors: Leach Franklin R.
Published: March 2019

The bioluminescent enzyme firefly luciferase has been the subject of detailed biochemical studies since the late 1940s. These studies have culminated in the cloning and sequence determination of some 161 different c-DNAs and/or genes for firefly luciferase and the determination of 6 crystallographic structures with and without reactants/products/analogs bound. This paper reviews these studies, searches for which amino acid residues are involved in the enzyme's action using chemical modification experiments, and analyzes the structure/function relationships of the various conserved amino acid residues. There are 71/550 amino acid residues conserved in the 161 different firefly luciferases. In my laboratory K-206, K-529, and R-437 were chemically modified; ATP inhibited these modifications suggesting that they are involved in the reaction. An integrated picture of the active site is postulated.
Study on the Chemical Constituents of Premna Integrifolia L
Authors: Hang Nguyen Thi Bich , Ky Pham Thanh , Van Minh Chau , Cuong Nguyen Xuan , Thao Nguyen Phuong , Van Kiem Phan
Published: March 2019

Phytochemical study on the plant Premna integrifolia L. led to the isolation of twelve compounds. In which, a new acylated iridoid glycoside, 6- O-(3″- O-acetyl-2″- O-trans-p-coumaroyl)-α-L-rhamnopyranosylcatalpol (premnacorymboside A) (1), was isolated from the flowers along with 10- O-trans-p-methoxycinnamoylcatalpol (3) and verbascoside. From the leaves, a new iridoid glycoside, 6- O-(3″- O-trans-p-coumaroyl)-α-L-rhamnopyranosylcatalpol (premnacorymboside B) (2), together with 10- O-trans-p-methoxycinnamoylcatalpol (3), scutellarioside II (4), premnaodoroside A (5), 1- O-trans-p-coumaroyl-α-L-rhamnopyranoside, hexyl glucoside, 4-hydroxy-2-methoxybenzaldehyde, and 4-hydroxybenzaldehyde were obtained. The new compound premnacorymboside A (1) and scutellarioside II (4), were also isolated from the stem bark along with quercetin 3-rutinoside and leonuriside A. The structure determinations were based on physical and spectroscopic evidence.
Bioactive Semisynthetic Derivatives of (S)-(+)-Curcuphenol
Authors: Gaspar Helena , Moiteiro Cristina , Sardinha João , González-Coloma Azucena
Published: March 2019

New semisynthetic sesquiterpene derivatives (3–7, 10), together with two known ones (8–9) were prepared from ( S)-(+)-curcuphenol (1), isolated from the Caribbean sponge Didiscus oxeata. The natural sesquiterpenes 1 and ( S)-(+)-curcudiol (2), as well as semisynthetic derivatives 3–10, were evaluated against the herbivorous insect species Spodoptera littoralis, Leptinotarsa decemlineata and Rhopalosiphum padi. All compounds had an antifeedant effect on L. decemlineata. With R. padi, a structure-dependent antifeedant response was observed, with 1 being the most active, followed by 4 and 5. Furthermore, compounds 1, 4, 5, 7, 8 and 10 reduced S. littoralis larval weight, with 10 also reducing ingestion by S. littoralis larvae. Of the derivatives studied here, none showed stronger effects (either antifeedant or postingestive) than the parent compound 1. It can, therefore, be concluded that the structure of the side chain and the presence of the phenol ring of curcuphenol are important structural requirements for its insect antifeedant and growth regulation effects.
Eco-contribution to the Chemistry of Perezone, a Comparative Study, Using Different Modes of Activation and Solventless Conditions
Authors: Martínez Joel , Velasco-Bejarano Benjamín , Delgado Francisco , Pozas Rocío , Domínguez Héctor M. Torres , Ferrara José G. Trujillo , Arroyo Gabriel A. , Miranda René
Published: March 2019

A comparative study of the reactivity of two sesquiterpene quinones, perezone and isoperezone, with a series of five mercaptans, using three different modes of activation (thermal, infrared and microwave irradiations), and under the presence or absence of solvent was performed.
Fenugreek Extract Rich in 4-Hydroxyisoleucine and Trigonelline Activates PPARα and Inhibits LDL Oxidation: Key Mechanisms in Controlling the Metabolic Syndrome
Authors: Ibarra Alvin , He Kan , Bai Naisheng , Bily Antoine , Roller Marc , Coussaert Aurélie , Provost Nicolas , Ripoll Christophe
Published: March 2019

Fenugreek ( Trigonella foenum-graecum L.) has properties which are hypolipidemic, hypocholesterolemic, hypoglycemic, insulinotropic, and antioxidant. These properties are related to the control of the Metabolic Syndrome, a disorder of carbohydrate and lipid metabolism which increases the risk of diabetes and cardiovascular disease. The purpose of this study was to evaluate the effect of fenugreek extract (Hydroxylean®, Naturex) containing 25% of 4-hydroxyisoleucine (4-OH-Ile, isomer 2 S,3 R,4 S) and 15.7% of trigonelline on peroxisome proliferator-activated receptor alpha (PPARα) transcriptional activity and Cu2+-induced low-density lipoprotein (LDL) oxidation in vitro. The activation of PPARα is linked to controlling lipidemia, cholesterolemia and glycemia, all associated with diabetes and cardiovascular disease. Also, the inhibition of LDL oxidation reduces the risk of stroke. 1,000 μg/mL of fenugreek extract showed a 31.2% activation of PPARα as compared with the positive control, 100 μM of fenofibrate. Fenugreek extract also inhibited LDL oxidation induced by Cu2+ at concentrations higher than 5 μg/mL (P<0.01). To our knowledge, this is the first report on PPARα transcriptional activity and Cu2+-induced LDL oxidation in vitro for fenugreek extract rich in 4-OH-Ile and trigonelline. The findings support the current evidence on fenugreek's capacity to control the Metabolic Syndrome.
Characteristic Flavonoids from Acacia burkittii and A. Acuminata Heartwoods and their Differential Cytotoxicit to Normal and Leukemia Cells
Authors: Grace Mary H. , Wilson George R. , Kandil Fayez E. , Dimitriadis Eugene , Coates Robert M.
Published: March 2019

Bioassay-guided fractionation of extracts from Acacia burkittii and A. acuminata heartwoods against an L1210 (mouse lymphoma) cell line led to the isolation of two flavan-3,4-diols, melacacidin (1) and isomelacacidin (2), and three flavonoids, 3,7,8,3′,4′-pentahydroxyflavone (3), 7,8,3′,4′-tetrahydroxyflavanone (4) and 3,7,8,3′,4′-pentahydroxyflavanone (5). HPLC analyses (280 nm) of the 70% acetone extracts of the two plants showed different profiles in terms of the relative concentration of the five identified compounds. When tested against L1210, compounds 1 and 2 were the most active, giving ID50 values of 2.5 and 4.5 μg/mL, respectively. The lower activity of the other isolated compounds indicated the importance of the 3,4-hydroxyl groups for the cytotoxic activity of these flavonoids. The isolated compounds were either non-toxic or had very low toxicities against the “normal” CV-1 cell line (green monkey kidney cells). The O-methyl and O-acetyl derivatives of these compounds were inactive. Ten commercially available phenolic compounds (6-15) were also tested for their activity against both CV-1 and L1210 cell lines. Flavan-3,4-diols 1 and 2 were more cytotoxic to L1210 cells than all tested compounds, including catechin and epicatechin, the most abundant flavan-3-ols in many fruits and vegetable.
Antifungal and Insecticidal Activity of two Juniperus Essential Oils
Authors: Wedge David E. , Tabanca Nurhayat , Sampson Blair J. , Werle Christopher , Demirci Betul , Baser K. Husnu Can , Nan Peng , Duan Jia , Liu Zhijun
Published: March 2019

Essential oils of two Tibetan Junipers Juniperus saltuaria and J. squamata var. fargesii (Cupressaceae) were obtained by distilling dried leaves and branches using a Clevenger apparatus. Sixty-seven compounds from J. saltuaria and 58 from J. squamata var. fargesii were identified by gas chromatography—mass spectrometry (GC-MS). Both essential oils contained similar ratios of four abundant monoterpenoids: 44 and 35% sabinene, 13 and 9% elemol, 8 and 7% terpinen-4-ol, and 4 and 17% α-pinene, respectively. These oils had antifungal activity based on a direct bioautography assay of Colletotrichum acutatum, C. fragariae, and C. gloeosporioides, and insecticidal activity based on serial-time mortality bioassay of azalea lace bugs, Stephanitis pyrioides. Antifungal activity of Juniperus oils was weak when compared with commercial fungicides such as benomyl and captan. Whole Juniperus oils at quarter the dosage used against Colletotrichum species were more insecticidal than 10 mg/mL malathion, killing ≥70 - 90% adult lace bugs after 4 hours of exposure. Rf values of 0.18 for J. saltuaria oil and 0.19 for J. squamata oil indicated lipophilic monoterpenes which were the putative sources of biological activity.
Formulation Study of Tea Tree Oil Patches
Authors: Minghetti Paola , Casiraghi Antonella , Cilurzo Francesco , Gambaro Veniero , Montanari Luisa
Published: March 2019

The antimicrobial, antifungal and anti-inflammatory properties of tea tree oil (TTO), the essential oil of Melaleuca alternifolia are well documented. In order to optimize its therapeutic activity, TTO patches were designed. The aim of this work was the formulation of monolayer patches containing TTO. Moreover, the performance of oleic acid (OA) as a skin penetration enhancer in patches was evaluated. Terpinen-4-ol (T4OL), the main component of TTO, was the marker used to evaluate TTO skin permeability. The permeation study was performed through human epidermis by using Franz diffusion cells. Patches were prepared by using methacrylic copolymers, Eudragit E100 (EuE100) or Eudragit NE (EuNE), and a silicone resin, BioPSA7-4602 (Bio-PSA). TTO and OA contents were fixed at 10% w/w and 3% w/w, respectively. The patches were prepared by a casting method and characterised in terms of T4OL content and skin permeability.

All the selected polymers were suitable as the main component of the patch matrix. Since the main critical issue in the use of TTO is related to its toxicity after absorption, the local administration of TTO can take advantage of the use of patches based on EuE100 because of the high retained amount and the low permeation of T4OL. In this matrix, OA slightly increased the T4OL retained amount, improving the efficacy and safety of TTO patches.
Protective Role of Myricetin on Markers of Oxidative Stress in Human Erythrocytes Subjected to Oxidative Stress
Authors: Pandey Kanti Bhooshan , Mishra Neetu , Rizvi Syed Ibrahim
Published: March 2019

The protective effect of myricetin against tert-butylhydroperoxide (t-BHP) induced oxidative stress in human erythrocytes was investigated. Incubating erythrocytes with t-BHP (10−5M) caused development of oxidative stress, as evidenced by significant ( p < 0.05) increase in erythrocyte malondialdedyde (MDA) and protein carbonyl content, and decrease in intracellular reduced glutathione (GSH), membrane sulphydryl (-SH) groups. Incubation of erythrocytes with myricetin, simultaneously with t-BHP, protected the erythrocytes from oxidative stress, an effect which was dose-dependent. The results demonstrate that myricetin attenuates t-BHP induced oxidative damage, suggesting that supplementation of diet with myricetin/myricetin rich food may be beneficial in all pathological conditions where the antioxidant system of the body is overwhelmed.
Essential Oil Compositions and Cytotoxic Activities of Dendropanax capillaris, Oreopanax Nubigenus, and Schefflera Rodrigueziana from Monteverde, Costa Rica
Authors: Richmond Justin D. , Agius Brittany R. , Wright Brenda S. , Haber William A. , Moriarity Debra M. , Setzer William N.
Published: March 2019

The leaf essential oils of Dendropanax capillaris, Oreopanax nubigenus and Schefflera rodrigueziana (Araliaceae) were isolated by hydrodistillation and analyzed by GC-MS. The leaf oil of Dendropanax capillaris was composed of only four compounds, β-pinene (25.3%), δ-3-carene (44.7%), daucene (17.1%), and dauca-5,8-diene (12.9%). Oreopanax nubigenus leaf oil was dominated by the sesquiterpene hydrocarbons germacrene D (70.1%) and β-caryophyllene (11.8%), while Schefflera rodrigueziana leaf oil was made up entirely of sesquiterpene hydrocarbons, mostly germacrene D (27.6%), β-cubebene (27.2%), β-caryophyllene (12.2%), α-cubebene (11.1%), and α-copaene (10.8%). Both O. nubigenus and S. rodrigueziana leaf oils showed notable in-vitro cytotoxicity on MDA-MB-231 cells, which may be attributable to the relatively high concentrations of germacrene D and β-caryophyllene in those oils.
Compositional Variations and Anthelmentic Activity of Essential Oils from Rhizomes of Different Wild Populations of Acorus Calamus L. and its Major Component, β-Asarone
Authors: Kumar Ravendra , Prakash Om , Pant Anil K. , Hore Subrata K. , Chanotiya Chandan S. , Mathela Chandra S.
Published: March 2019

Hydro-distilled essential oils from Acorus calamus rhizomes collected from six different geographical zones in the northwest Himalayan region of Uttarakhand have been analyzed by GC and GC/MS. All the oils differed in their qualitative and quantitative make up, although β-asarone was the major constituent of all of them. The essential oils and the isolated β-asarone were screened for anthelmintic activity using contractility of Ascaridia galli. β-Asarone, in particular, showed potent activity with IC50 values of 75.4 ± 61.8 ng/mL.
Composition and Antibacterial Activity of Essential Oils of Artemisia Fragrans Willd. Leaves and Roots from Iran
Authors: Shafaghat Ali , Noormohammadi Yavar , Zaifizadeh Mohammad
Published: March 2019

Hydrodistillation of leaves and roots of Artemisia fragrans Willd. (Asteraceae) yielded 0.9% and 0.1 %(v/w) essential oils, respectively. GC/MS analysis allowed identification of 19 components, which made up 91.1% of the total oil from the leaves, while only 9 compounds (93.8%) were identified in the roots. The main components of the leaf oil were chrysanthenon (23.8%), 1, 8-cineole (23.7%), β-caryophyllene (9.6%), p-cymene (7. 7%), filifolide-A (5.7%) and filifolone (5.7%). In the root oil, the main constituents were camphor (67.0%) and camphene (16.9%). Antibacterial activity was tested against Grampositive and Gram-negative bacteria using the agar diffusion method. Activity was observed against two Gram-positive and one Gram- negative bacteria.
Minor Chemical Constituents of Caesalpinia Bonduc
Authors: Ata Athar , Udenigwe Chibuike C. , Gale Elikana M. , Samarasekera Radhika
Published: March 2019

From the ethanolic extract of Caesalpinia bonduc, one new diterpene, neocaesalpin P (1) and six known diterpenoids, neocaesalpin H (2), cordylane A (3), caesalpinin B (4), bonducellpin E (5), caesalpinolide A (6), and 17-methylvouacapane-8(14),-9(11)-diene (7) were isolated. Structures of these compounds were determined from NMR spectroscopic studies. Compounds 1-7 exhibited modest antibacterial activities. All of these compounds were weakly active in glutathione S-transferase inhibition assays.
Cytotoxic and HLE-Inhibitory Tetramic Acid Derivatives from Marine-Derived Fungi
Authors: Neumann Kerstin , Kehraus Stefan , Gütschow Michael , König Gabriele M.
Published: March 2019

Tetramic acid derivatives are an important class of nitrogen heterocycles with a pyrrolidine-2,4-dione core as a key structural motif. From the sponge-derived fungus Beauveria bassiana, a new equisetin-like tetramic acid derivative, beauversetin (1), was isolated. The sea weed-derived fungus Microdiplodia sp. produced the tetramic acid derivative 2 (Sch210972) which was shown to inhibit human leucocyte elastase (HLE) with an IC50 of 1.04 μg mL−1.
Analysis of Essential Oil from Teucrium maghrebinum Greuter et Burdet Growing Wild in Algeria
Authors: Formisano Carmen , Rigano Daniela , Senatore Felice , Al-Hillo Malik R. Y. , Piozzi Franco , Rosselli Sergio
Published: March 2019

The chemical composition of the essential oil obtained from aerial parts of Teucrium maghrebinum growing wild in Algeria was analyzed by GC and GC-MS. Among the 66 identified compounds, δ-cadinene (12.7%), germacrene D (11.4%), γ-cadinene (9.5%) and 4-vinyl guaiacol (4.0%) were the most abundant. The oil is strongly characterized by the presence of sesquiterpenes (61.5%), particularly hydrocarbon sesquiterpenes (49.6%).
Essential Oil Composition of Three Peperomia Species from the Amazon, Brazil
Authors: de Lira Patrícia Natália B. , da Silva Joyce Kelly R. , Andrade Eloisa Helena A. , Sousa Pergentino José C. , Silva Nayla N. S. , Maia José Guilherme S.
Published: March 2019

The essential oils of three species of Peperomia from the Amazon, Brazil, were hydrodistilled and their 96 volatile constituents identified by GC and GC-MS. The main constituents found in the oil of P. macrostachya were epi-α-bisabolol (15.9%), caryophyllene oxide (12.9%), myristicin (7.6%), an aromatic compound (6.6%) and limonene (5.4%). The oil of P. pellucida was dominated by dillapiole (55.3%), ( E)-caryophyllene (14.3%) and carotol (8.1%). The major volatile found in the oil of P. rotundifolia was decanal (43.3%), probably a fatty acid-derived compound, followed by dihydro-β-santalol (9.0%), ( E)-nerolidol (7.9%) and limonene (7.7%). The aromatic compounds elemicin, myristicin, apiole, dillapiole and safrole identified in these Peperomia species has been found also in Amazon Piper species. The oils and methanol extracts showed high brine shrimp larvicidal activities. The oil of P. rotundifolia (LC50 = 1.9 ± 0.1 μg/mL) was the more toxic, followed by the extract of P. pellucida (LC50 = 2.4 ± 0.5 μg/mL) and the oil of P. macrostachya (LC50 = 9.0 ± 0.4 μg/mL), therefore with important biological properties.
Phenolic Profile and Antioxidant Evaluation of Mentha x Piperita L. (Peppermint) Extracts
Authors: Dorman H.J. Damien , Koşar Müberra , Başer K Hüsnü C , Hiltunen Raimo
Published: March 2019

Seven extracts were prepared from Mentha x piperita (peppermint) leaves in sequence using a Soxhlet apparatus, viz. (40-60°) light petroleum (PE), dichloromethane (CH2Cl2), acetonitrile (ACN), ethyl acetate (EtOAc), methanol (MeOH), n-butanol and water (H2O) extracts. The phenolic and flavonoid content of each extract were estimated using spectrophotometric methods whilst a qualitative-quantitative analysis was made by reverse-phase high performance liquid chromatography coupled with photodiode array detection (HPLC-PDA). Each extract was assessed in a battery of six antioxidant-related assays so as to determine their iron(III) reductive, iron(II) chelating and free radical scavenging abilities. The MeOH-soluble extract contained the greatest content of total phenols and flavonoids based upon the Folin-Ciocalteu and 2-aminoethyl diphenylborate reagent data and HPLC-PDA analysis. Based upon the chromatographic and UV-spectral data, the leaves principally contained the cinnamic acid caffeic acid, the depside rosmarinic acid and flavonoids (flavones and flavanones). Eriocitrin (383.3 ± 2.2 mg/g extract) and rosmarinic acid (381.2 ± 1.9 mg/g extract) were the most abundant components identified within the leaves, whilst naringenin-7- O-glucoside (0.8 ± 0.01 mg/g extract) was the least abundant component identified being found only in the EtOAc-soluble extract. The EtOAc, ACN and H2O-soluble extracts demonstrated the most potent iron(III) reductive and 1,1′-diphenyl-2-picrylhydrayl, 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) and hydroxyl free radical scavenging properties; however, the H2O and CH2Cl2-soluble extracts were the most potent extracts in the β-carotene-linoleic acid bleaching inhibition assay. In terms of iron(II) chelation – an important antioxidant property - the PE, MeOH and H2O extracts demonstrated moderate iron(II) chelating activity.
Antiinflammatory Potential and Fatty Acid Content of Lipophilic Leaf Extracts of Four Staphylea L. Species
Authors: Lacikova Lubica , Pferschy-Wenzig Eva-Maria , Masterova Irena , Grancai Daniel , Bauer Rudolf
Published: March 2019

Staphylea preparations are used in TCM and have been used by native Americans for a number of indications, such as rheumatism. Based on this knowledge, the anti-inflammatory activity of light petroleum extracts of leaves of Staphylea colchica Stev., S. elegans Zab., S. holocarpa Hemsl. and S. pinnata L. has been determined using in vitro assays for inhibition of cyclooxygenase (COX-1 and COX-2) and leukotriene B4 (LTB4) formation by lipoxygenase (5-LOX). All extracts inhibited COX-1 and COX-2, with S. holocarpa and S. elegans performing best. Inhibition of LTB4 formation was less pronounced. As unsaturated fatty acids are known to inhibit arachidonic acid metabolism in vitro, the fatty acid content was determined of the active extracts and set in correlation with their activity. Unsaturated fatty acids were found to contribute to the observed COX-2 and LTB4 formation inhibitory activity to a different extent.
Mutagenesis and Genotypic Characterization of Aspergillus niger FCBP-02 for Improvement in Cellulolytic Potential
Authors: Shafique Shazia , Bajwa Rukhsana , Shafique Sobiya
Published: March 2019

Cellulase is a collective term that encompasses enzymes which catalyze reactions that participate in the degradation of insoluble cellulose to soluble carbohydrates. In the present study, production of extra cellular cellulases by a filamentous fungus, Aspergillus niger FCBP-02, was studied in solid-state fermentation (SSF) as well as in submerged fermentation (SmF). Trials were conducted to evaluate the effect of mutagenesis by UV irradiation (5–40 min) and ethyl methane sulfonate (EMS) treatment (50–300 μg mL−1) to obtain hyper active cellulase enzyme producers among the potential strains. The enzyme activity assays of parental and mutant strains clearly revealed significantly higher cellulase activity of mutant A-Ch-5.5 (96 Units mL−1), followed by A-UV-5.6 (71 Units mL−1) with respect to the wild strain of A. niger FCBP–02 (53.7 Units mL−1). The profile of genetic variability among wild and mutant derivatives was scrutinized through RAPD–PCR. The expression pattern of mutants exhibited that the mutants were isogenic variants of the wild type and the out performance of the mutants could be attributed to the change in genetic make up.
Enantiomeric Composition of (3R)-(-)- and (3S)-(+)-Linalool in Various Essential Oils of Indian Origin by Enantioselective Capillary Gas Chromatography-Flame Ionization and Mass Spectrometry Detection Methods
Authors: Chanotiya Chandan S. , Yadav Anju
Published: March 2019

Enantiomeric ratios of linalool have been determined in various authentic essential oils of Indian origin using 10% heptakis(2,3-di- O-methyl-6- O-tert-butyldimethylsilyl)-β-cyclodextrin as a chiral stationary phase. A complete enantiomeric excess (ee) for (3 S)-(+)-linalool was characteristic of Lippia alba and Cinnamomum tamala leaf oils while less than 90% excess was noticed in Zanthoxylum armatum leaf, Zingiber roseum root/rhizome and Citrus sinensis leaf oils. On the contrary, an enantiomeric excess of (3 R)-(-)-linalool characterizes essential oils of basil (100% for Ocimum basilicum) and bergamot mint (72 to 75% for Mentha citrata). Notably, some essential oils containing both enantiomers in equal ratios or in racemic forms are rose, geranium, lemongrass and Origanum. The enantiomeric composition studies are discussed as indicators of origin authenticity and quality of essential oil of Indian origin.
Bioactivity of Grape Chemicals for Human Health
Authors: Iriti Marcello , Faoro Franco
Published: March 2019

Grapevine ( Vitis vinifera) products, grape and grape juice, represent a valuable source of bioactive phytochemicals, synthesized by three secondary metabolic pathways (phenylpropanoid, isoprenoid and alkaloid biosynthetic routes) and stored in different plant tissues. In the last decades, compelling evidence suggested that regular consumption of these products may contribute to reducing the incidence of chronic illnesses, such as cancer, cardiovascular diseases, ischemic stroke, neurodegenerative disorders and aging, in a context of the Mediterranean dietary tradition. The health benefits arising from grape product intake can be ascribed to the potpourri of biologically active chemicals occurring in grapes. Among them, the recently discovered presence of melatonin adds a new element to the already complex grape chemistry. Melatonin, and its possible synergistic action with the great variety of polyphenols, contributes to further explaining the observed health benefits associated with regular grape product consumption.
Thymol-evoked Ca2+ Mobilization and Ion Currents in Pituitary GH3 Cells
Authors: Shen Ai-Yu , Huang Mei-Han , Wang Trey-Shy , Wu Hui-Ming , Kang Ya-Fei , Chen Chi-Lan
Published: March 2019

In this study, an attempt was made to elucidate the effects of thymol, a monocyclic phenolic compound, on Ca2+ mobilization and ion currents in pituitary GH3 cells with the aid of fura-2 fluorimetry and the whole-cell voltage-clamp technique. Thymol increased intracellular Ca2+ concentrations ([Ca2+]i) in GH3 cells loaded with Ca2+-sensitive dye fura-2. Removing extracellular Ca2+ reduced the thymol-induced [Ca2+]i rise. In Ca2+-free solution, thymol-evoked [Ca2+]i rise was unchanged by depleting the Ca2+ store with thapsigargin (1 μM), while the thapsigargin-induced [Ca2+]i rise was reduced by pretreatment with thymol. These results imply that the Ca2+ stores depleted by thymol comprise thapsigargin-sensitive and thapsigargin-insensitive pools. In addition, after depletion of the internal Ca2+ store with 100 μM thymol in Ca2+-free solution, a subsequent application of Ca2+ greatly induced a [Ca2+]i increase. The results indicate that, similar to thapsigargin, 100 μM thymol may activate the capacitative calcium entry (CCE) channel. However, thymol (100 μM) had a slight depressant action in L-type calcium current ( ICaL). The stimulatory actions of thymol on Ca2+ signaling may partly be responsible for the underlying cellular mechanisms through which it affects neuroendocrine functions.
Iridoids from Spathodea Campanulata P. Beauvais Leaves
Authors: Gouda Yaser G.
Published: March 2019

Three new and four known iridoids have been isolated from the leaves of Spathodea campanulata, the structures of the new compounds were determined as 6- O-trans-caffeoyl-decinnamoyl globularimin, 6- O-trans-caffeoyl-asystasioside E and 6- O-trans-caffeoyl-5,7-bisdeoxycynanchoside and provisionally named as spatheosides A (1), B (2) and C (3) respectively. The known iridoids were identified as verminoside (4), 6′- O-trans-caffeoyl-loganic acid (5), catalpol (6) and ajugol (7). The structures of the isolated compounds were characterized by different spectroscopic methods.
Analysis of Salvia Coccinea from Jamaican Populations
Authors: Martin Glenroy D. A. , Reynolds William F. , Reese Paul B.
Published: March 2019

This is the first report of a phytochemical investigation of Jamaican populations of a local folk medicinal plant Salvia coccinea (Lamiaceae/Labiatae). Apart from the presence of β-sitosterol, phytochemical profiling of the aerial parts yielded compounds other than those previously reported from Indian and Italian populations. The triterpenes betulinic acid and betulin, the phytosterols β-sitosterol and β-sitosterol-3- O-β-D-glucopyranoside, as well as the steroid precursor squalene were isolated. The structures of the compounds were established by comparison of NMR spectroscopic data with those reported in literature.
Globulixanthone F, a New Polyoxygenated Xanthone with an Isoprenoid Group and Two Antimicrobial Biflavonoids from the Stem Bark of Symphonia Globulifera¶
Authors: Mkounga Pierre , Fomum Zacharias T. , Meyer Michèle , Bodo Bernard , Nkengfack Augustin E.
Published: March 2019

Bioassay-guided fractionation of the stem bark of Symphonia globulifera has yielded three known xanthones, ugaxanthone (1), mbarraxanthone (2) and gentisein (3), two biflavonoid derivatives named GB2 (4) and manniflavanone GB3 (5), and one new polyoxygenated xanthone with an isoprenoid group, named globulixanthone F (6). The structures of these compounds were elucidated by means of spectroscopic methods. The spectral data of 1 and 2 are reported here for the first time, as well as the antimicrobial activity of globulixanthone F against a range of microorganisms. We also report the total synthesis of the xanthone skeleton.
Antibacterial Activity and Composition of Essential Oils from Flower, Leaf and Stem of Chaerophyllum Macropodum Boiss. from Iran
Authors: Shafaghat Ali
Published: March 2019

The hydrodistilled essential oils from flower, leaf and stem of Chaerophyllum macropodum Boiss. were analyzed by GC and GC/MS. The flower oil was characterized by high amounts of myristicin (42.5%) and trans-β-ocimene (41.0%). In the leaf oil eighteen constituents, representing 99.3% of the total, were identified of which trans-β-ocimene (24.9%), myristicin (15.7%), terpinolene (14.5%), fenchyl acetate (13.9%), cis-β-ocimene (6.3%) and sabinene (6.1%) were major components. The main components of the stem oil were trans-β-ocimene (54.2%), myristicin (22.4%) and sabinene (8.9%). Antibacterial activities of the flower, leaf and stem oils were evaluated using the microdilution broth method. Inhibitory effects on Escherichia coli and Salmonella typhi were recorded.
Chemical Composition and Antimicrobial Activity of Clausena Indica (Dalz) Oliv. (Rutaceae) Essential Oil from Vietnam
Authors: Diep Pham Thi Minh , Pawlowska Agata Maria , Cioni Pier Luigi , Van Minh Chau , Huong Le Mai , Braca Alessandra
Published: March 2019

The essential oil obtained from the branches and leaves of Clausena indica (Dalz) Oliv. (Rutaceae) has been analyzed by GC/MS. Fifty-three components of the essential oil, representing 96.9% of the total amount, were identified. The main constituents were myristicin (35.3%), terpinolene (16.7%), and δ-3-carene (11.3%). The essential oil was screened for antimicrobial activity, showing positive results against some bacterial strains. Moreover, a comparison between constituents of C. indica essential oil with the ones reported in the literature for other Clausena ssp. is pointed out and some chemotaxonomic considerations have been identified.
Phenolic Glycoside from the Roots of Viburnum Dilatatum
Authors: Lu Dan , Yao Shanjing
Published: March 2019

Chemical investigation of the roots of Viburnum dilatatum Thunb resulted in the isolation and characterization of a new phenolic glycosides 2-(-glucopyranosyloxy)-benzyl 3-(-glucopyranosyloxy)-benzoate (1), together with two known compounds. Their structures were established by spectroscopic means and by comparison with the literature values.
Phytochemical Investigation of the Australian Lichens Ramalina glaucescens and Xanthoria parietina
Authors: Dias Daniel A. , Urban Sylvia
Published: March 2019

Phytochemical investigation of the Australian lichen, Ramalina glaucescens resulted in the isolation of a new halogenated depside, 5-chlorosekikaic acid 5, together with (+)-usnic acid 1, sekikaic acid 2, atranorin 6 and parietin 7, the latter of which was isolated from the associated (co-occurring) lichen, X. parietina. Compound 5 is suspected to be an artifact of the isolation procedure. All structures were assigned using spectroscopic methods and mass spectrometry. In addition to the full characterization of 5, this report represents the first application of 2D NMR spectroscopy to complete the unequivocal chemical shift assignment for compounds 2 and 7. Compounds 1-2 and 5-7 all displayed varying degrees of antitumor activity (ranging from an IC50 of 15 μM to >44 μM) with compounds 1, 2 and 5 also displaying antibacterial properties. Of these, (+)-usnic acid 1 displayed the most significant antitumor and antibacterial activities.
Strain Improvement and Genetic Characterization of Indigenous Aspergillus Flavus for Amylolytic Potential
Authors: Shafique Sobiya , Bajwa Rukhsana , Shafique Shazia
Published: March 2019

Aspergillus flavus FCBP–231, a filamentous fungus, was genetically modified for its ability to reveal extra cellular α-amylase activity. For strain improvement, the selected strains were subjected to UV irradiation (5-40 min exposure) and EMS treatment (50–300 μg mL−1) for hyper activity of an α-amylase enzyme. The mutants were quantitatively compared with the parental strain. UV and chemical mutagenesis brought about a dramatic enhancement in enzymatic activity. The mutant strains Af-UV-5.3 and Af-Ch-5.7 exhibited 79 and 110% more enzyme activity than the native strain A. flavus FCBP-231. This improvement in enzyme activity of the mutants suggests that they are suitable strains to be used in biotechnology. RAPD–PCR analysis revealed different patterns of amplicons of native as well as mutant derivatives, which suggested that the mutation imparted changes in the genetic make up of the mutants probably involved enzyme production control.
Chemical Composition and Antimicrobial Activity of the Essential Oil of Anaphalis nubigena Var. Monocephala
Authors: Joshi Rajesh K. , Pande Chitra , Mujawar Mohammad H. K. , Kholkute Sanjiva D.
Published: March 2019

The essential oil composition of the aerial parts of Anaphalis nubigena DC. var. monocephala (DC.) C. B. Clarke collected from Pindari glacier at a height of 3300 m, was analyzed by using GC and GC/MS. Sixty components were identified, accounting for 95.9% of the total oil. The main constituents were α-guaiene (12.3%), γ-muurolene (10.4%), γ-cadinene (8.3%), α-muurolol (7.4%), α-gurjunene (6.0%) and α-bulnesene (5.8%). The oil was found to be rich in sesquiterpene hydrocarbons (60.1%). The oil was active against Escherichia coli (NCIM 2065) and Klebsiella pneumoniae (NCIM 2957), with MIC values of 125 μg/mL and 500 μg/mL, respectively.
VCD Determination of the Absolute Configuration of Stypotriol
Authors: Muñoz Marcelo A. , Areche Carlos , San-Martín Aurelio , Rovirosa Juana , Joseph-Nathan Pedro
Published: March 2019

The absolute configuration of the pentacyclic ichthyotoxin stypotriol, a constituent of Stypopodium zonale, was deduced to be 3S,5R,8R,9R,10S,13S,14S-(-)-1 by vibrational circular dichroism spectroscopy of the derived triacetate 2 in comparison to DFT B3LYP/DGDZVP calculations. Compound 2, C33H46O7 having 300 electrons, is the largest natural product successfully studied by VCD to date.
Evaluation of the Antioxidant and Antimicrobial Properties of in vitro Cultured Drosera intermedia Extracts
Authors: Grevenstuk Tomás , Gonçalves Sandra , Almeida Sara , Coelho Natacha , Quintas Célia , Gaspar Maria Nelma , Romano Anabela
Published: March 2019

Evaluation of the antioxidant activity of the methanol, water and n-hexane extracts of Drosera intermedia, determined by the Folin-Ciocalteau (F-C), trolox equivalent antioxidant capacity (TEAC) and oxygen radical antioxidant capacity (ORAC) assays showed that the methanol extract had the highest antioxidant activity (F-C: 378.6 ± 31.5 μmolGAE/mgextract; TEAC: 332.2 ± 29.1 μmolTE/mgextract; ORAC: 64.7 ± 7.8 μmolTE/mgextract). Antimicrobial activity was tested against seven bacterial and eight yeast strains using the agar diffusion assay, followed by the determination of minimum inhibitory concentrations (MIC). All tested D. intermedia extracts demonstrated strong antimicrobial properties with a broad spectrum of activity. However, the n-hexane extract exhibited much greater activity than water and methanol extracts. The most susceptible microorganisms to the n-hexane extract were Staphylococcus epidermidis ATCC 12228 and Candida albicans YP0175, for which a MIC value of 13.0 μg/mL was scored.
The Composition of the Essential Oil from Cyperus distans Rhizome
Authors: Lawal Oladipupo A. , Oyedeji Adebola O.
Published: March 2019

The essential oil from the rhizomes of Cyperus distans L.f. obtained by hydrodistillation was analyzed by capillary GC and GC/MS techniques. Eight constituents were identified, representing 99.6% of the total oil. The major components of the oil were cyperene (47.6%), α-pinene (18.8%), 1,8-cineole (14.5%) and caryophyllene oxide (7.3%).
Essential Oil Composition and Enantiomeric Distribution of Fenchone and Camphor of Lavandula cariensis and L. stoechas subsp. stoechas grown in Greece
Authors: Tzakou Olga , Bazos Ioannis , Yannitsaros Artemios
Published: March 2019

The essential oils from leaves and inflorescences of L. cariensis Boiss. and L. stoechas L. subsp. stoechas collected in Greece were analyzed by GC and GC/MS. In the inflorescences and leaves essential oils of L. cariensis the most abundant metabolite was camphor (51.8, 48.8% respectively), whereas in the essential oils of L. stoechas subsp. stoechas, the main constituents were fenchone (39.9, 21.0% respectively) and camphor (24.2, 26.3% respectively). Both enantiomers of camphor were present, whereas only (+) fenchone was detected.
Chemical Composition, Olfactory Evaluation and Antioxidant Effects of Essential Oil from Mentha x piperita
Authors: Schmidt Erich , Bail Stefanie , Buchbauer Gerhard , Stoilova Ivanka , Atanasova Teodora , Stoyanova Albena , Krastanov Albert , Jirovetz Leopold
Published: March 2019

The chemical composition of the essential oil from peppermint ( Mentha x piperita L.) was analyzed by GC/FID and GC-MS. The main constituents were menthol (40.7%) and menthone (23.4%). Further components were (+/-)-menthyl acetate, 1,8-cineole, limonene, β-pinene and β-caryophyllene. Peppermint oil possessed antiradical activity with respect to DPPH (diphenyl picryl hydrazyl) and hydroxyl (OH•) radicals, exercising stronger antioxidant impact on the OH• radical. The concentrations required for 50% inhibition of the respective radical (IC50) were 860 μg/mL for DPPH and 0.26 μg/mL for OH•. Peppermint essential oil demonstrated antioxidant activity in a model linoleic acid emulsion system in terms of inhibiting conjugated dienes formation by 52.4% and linoleic acid secondary oxidized products generation by 76.9% (at 0.1% concentration).
Chemical Constituents of Nauclea latifolia and their Anti-GST and Anti-Fungal Activities
Authors: Ata Athar , Udenigwe Chibuike C. , Matochko Wadim , Holloway Paul , Eze Michael O. , Uzoegwu Peter N.
Published: March 2019

The crude ethanolic extract of Nauclea latifolia yielded five known compounds, strictosamide (1), naucleamides A (2), naucleamide F (3), quinovic acid-3-O-β-rhamnosylpyranoside (4), and quinovic acid 3-O-β-fucosylpyranoside (5). Microbial reactions, using a whole cell culture of Rhizopus circinans on compound (1), yielded three analogues, 10-hydroxystrictosamide (6), 10-4bT-glucosyloxyvincoside lactam (7) and 16,17-dihydro-10-β-glucosyloxyvincoside lactam (8). Compounds 1-8 were identified with the aid of extensive NMR spectral studies. Compound 8 was found to be a new metabolite. Compounds 1-8 exhibited different levels of anti-GST and antifungal activities.
New Compounds from Leaves of Smallanthus sonchifolius
Authors: Zheng Xiang , Kuo Gai , De-Qiang Dou , Ting-Guo Kang , Yu-Yuan Shi , Feng Dong
Published: March 2019

A new octadecatrienoic acid and a new benzyl glycoside, along with a known compound, were isolated from the leaves of Smallanthus sonchifolius. The structures of the two new compounds were elucidated as 13(R)-hydroxy-octadeca-(9E,11E,15Z)-trienoic acid (1) and benzyl alcohol 7-O-α-L-arabinopyranosyl(1″→2′)-β-D-glucopyranoside (2) on the basis of spectroscopic analysis and chemical evidence. The known compound was identified as 13(R)-hydroxy-octadeca-(9Z,11E,15Z)-trienoic acid (3) by comparison of its spectral data with that reported. Compound 3 was isolated for the first time from the title plant.
Composition and Biological Activity of Essential Oils from Protium confusum
Authors: Santana Ana I. , Vila Roser , Espinosa Alex , Olmedo Dionisio , Gupta Mahabir P. , Cañigueral Salvador
Published: March 2019

The composition and biological activity of the essential oils from leaves, fruits, stems and bark of Protium confusum are reported for the first time. Forty-six to sixty-three constituents were identified ranging from 73.8% to 98.5% of the samples. Limonene (60.2%) was the main component in the fruit oil, whereas spathulenol (19.3%), β-caryophyllene oxide (14.1%) and β-caryophyllene (8.0%) reached the highest percentages in the oil from leaves. The volatile oils from bark and stems showed the same major constituents: p-cymen-8-ol (14.4% and 6.1%, respectively), spathulenol (9.5% and 9.0% respectively), and hexadecanoic acid (8.4% and 7.8%, respectively). The composition of the essential oils differed significantly from those of previously investigated Protium species. Three out of the four samples exhibited antibacterial activity against Staphylococcus aureus and Mycobacterium smegmatis, the one from leaves being the most active, with MIC values of 62.5 μg/mL in both cases. No activity against Candida albicans was detected. The bark oil showed the highest larvicidal activity against Aedes aegypti (LC100 = 125 μg/mL).
MS-based Plant Metabolomic Approaches for Biomarker Discovery
Authors: Wolfender Jean-Luc , Glauser Gaetan , Boccard Julien , Rudaz Serge
Published: March 2019

Metabolomics, which aims at the comprehensive and quantitative analysis of wide arrays of metabolites in biological samples, is playing an increasingly important role in plant science. Various biological issues have been successfully studied by this holistic approach that includes global metabolite composition assessment, mutant characterization, taxonomy, developmental processes, stress response, interaction with environment, quality control assessment and mode of action of herbal medicine. This review summarizes the main mass spectrometry methods used for performing these studies and discusses the potential, but also the current limitations of the various approaches. The intention is not to cover exhaustively the field, which has considerably grown over about one decade, but to give a brief insight into the methods commonly employed and discuss some applications that reveal the potential of metabolomics in phytochemistry and systems biology.
Decades of Phytochemical Research on African Biodiversity
Authors: Khalid Sami A.
Published: March 2019

This review provides a panoramic view of Prof. Kurt Hostettmann's contribution to the study of African medicinal plants as documented in over 85 publications with collaborators from about a dozen African countries. Many novel bioactive secondary metabolites were isolated, their structures elucidated by hyphenated HPLC techniques and their biological activity determined.
Chemical Constituents of the Endophytic Fungus Lecythophora sp. Isolated from Alyxia reinwardtii
Authors: Sugijanto Noor Erma , Diesel Arnulf , Ebel Rainer , Indrayanto Gunawan , Zaini Noor Cholies
Published: March 2019

Seven compounds, (2R)-3-(2-hydroxypropyl)-benzene-1,2-diol (1), kojic acid (2), 7-O-acetyl-kojic acid (3), p-hydroxybenzoic acid (4), emodine (5), 7-chloroemodine (6), and ergosterol-5,8-peroxide (7) were isolated from the endophytic fungus Lecythophora sp. (specimen codes 30.1 and 30.5), which were isolated from Alyxia reinwardtii (Apocynaceae).
A New 5-Acyl-2-methylpyrrole from the Endophytic Fungus S20 of Cephalotaxus hainanensis
Authors: Dai Wen-jun , Dai Hao-fu , Wu Jiao , Liu Jian , Mei Wen-li
Published: March 2019

A new 5-acyl-2-methylpyrrole, isolated from the endophytic fungus S20 of Cephalotaxus hainanensis, was elucidated as 1-(5-methyl-1H-pyrrol-2-yl)-2-((2S*,3R*)-3-((E)-prop-1-enyl)oxiran-2-yl)ethanone (1) on the basis of spectroscopic evidence, including 1D- and 2D-NMR (HMQC, 1H-1H COSY, HMBC and ROESY) and MS analysis. Compound 1 showed inhibitory effects on Staphylococcus aureus and methicillin-resistant S. aureus by the filter paper disc agar diffusion method.
Analytical Aspects of Diterpene Alkaloid Poisoning with Monkshood
Authors: Colombo Maria Laura , Bugatti Carlo , Davanzo Franca , Persico Andrea , Ballabio Cinzia , Restani Patrizia
Published: March 2019

A sensitive and specific method for aconitine extraction from biological samples was developed. Aconitine, the main toxic alkaloid from plants belonging to Aconitum species (family Ranunculaceae), was determined in plant material by an external standard method, and by a standard addition calibration method in biological fluids. Described here is one fatal case and five intoxications of accidental aconitine poisoning following the ingestion of aconite mistaken for an edible grass, Aruncus dioicus (Walt.) Fernald, “mountain asparagus”, and Cicerbita alpina (L.) Wallroth. The aconitine content in urine was in the range 2.94 μg/mL (dead patient) – 0.20 μg/mL (surviving patients), which was almost two to four times higher than that in plasma.
Chemical Composition and Antimycobacterial Activity of the Essential Oil from Anemia tomentosa var. anthriscifolia
Authors: Pinto Shaft Corrêa , Leitão Gilda Guimarães , de Oliveira Danilo Ribeiro , Bizzo Humberto Ribeiro , Ramos Daniela Fernandes , Coelho Tatiane Silveira , Silva Pedro Eduardo A. , Lourenço Maria Cristina S. , Leitão Suzana Guimarães
Published: March 2019

The essential oil from Anemia tomentosa var. anthriscifolia showed in vitro activity against Mycobacterium tuberculosis (MIC 100 μg/ml) and therefore was characterized by gas chromatography (GC) and by gas chromatography coupled with mass spectrometry (GC-MS). The major constituents of this essential oil were triquinane sesquiterpenes: silphiperfol-6-ene (14.7%), (–)-epi-presilphiperfolan-1-ol (30.6%), presilphiperfol-7-ene (3.9%), cameroonan-7α-ol (4.4%), prenopsan-8-ol (1.9%) and presilphiperfolan-8-ol (8.3%), suggesting the existence of different chemotypes for this species. The essential oil was fractionated by column chromatography and its major constituent and fractions were assayed against Mycobacterium tuberculosis and M. smegmatis. (–)-epi-Presilphiperfolan-1-ol exhibited an MIC of 120 μg/ml against M. tuberculosis H37Rv.
Constituents of the Polar Extracts from Algerian Pituranthos scoparius
Authors: Dahia Mostefa , Siracusa Laura , Laouer Hocine , Ruberto Giuseppe
Published: March 2019

The methanolic and aqueous extracts of Pituranthos scoparius (Coss. & Dur.) Benth. & Hook. (Apiaceae) have been analyzed and fifteen metabolites were identified: two cinnamic acids (5-O-caffeoyl quinic acid and 5-feruloyl quinic acid), and thirteen known flavonoids (vicenin-2, six quercetin and six isorhamnetin O-glycosylated derivatives). 5-O-caffeoylquinic acid was the main component, while, of the flavonoids, the isorhamnetin derivatives were present to a greater extent.
Verbascoside isolated from Lepechinia speciosa has inhibitory Activity against HSV-1 and HSV-2 in vitro
Authors: Martins Fernanda O. , Esteves Patricia F. , Mendes Gabriella S. , Barbi Nanci S. , Menezes Fabio S. , Romanos Maria T.V.
Published: March 2019

Verbascoside has been isolated form L. speciosa after several different chromatographic methods. After its purification, the structure has been unequivocally established using modern spectroscopic techniques. As for the antiviral activity, the maximum non toxic concentration has been established and this concentration has been used in the anti herpes assay, in vitro. Mechanism of action for this molecule regarding the anti-herpes activity has been studied encompassing the following assays: virucidal activity, cellular receptor assay, penetration assay and intracellular assay, in order to understand the activity for this natural product.