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Ruta graveolens extracts and metabolites against Spodoptera frugiperda

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No. 11 Ruta graveolens Extracts and Metabolites against Spodoptera frugiperda 1955 - 1958

Benjamín A. Ayil-Gutiérrez, Jesús M. Villegas-Mendoza, Zuridai Santes-Hernández, Alma D. Paz-González, Maribel Mireles-Martínez, Ninfa M. Rosas-García and Gildardo Rivera*

Laboratorio de Biotecnología Ambiental, Centro de Biotecnología Genómica, Instituto Politécnico Nacional, Reynosa, 88710, México [email protected]

Received: March 23rd, 2015; Accepted: July 25th, 2015

The biological activity of Ruta graveolens leaf tissue extracts obtained with different solvents (ethyl acetate, ethanol, and water) and metabolites (psoralen, 2- undecanone and rutin) against Spodoptera frugiperda was evaluated. Metabolites levels in extracts were quantified by HPLC and GC. Ethyl acetate and ethanol extracts showed 94% and 78% mortality, respectively. Additionally, psoralen metabolite showed a high mortality as cypermethrin. Metabolite quantification in extracts shows the presence of 2-undecanone (87.9 µmoles mg-1 DW), psoralen (3.6 µmoles mg-1 DW) and rutin (0.001 µmoles mg-1 DW). We suggest that these concentrations of 2-undecanone and psoralen in R. graveolens leaf tissue extracts could be responsible for S. frugiperda mortality.

Keywords: Metabolites, Quantification, Spodoptera frugiperda, Ruta graveolens, Psoralen, 2-Undecanone, Rutin.

The fall armyworm, Spodoptera frugiperda (Lepidoptera: Noctuidae J. E. Smith), is a worldwide pest of economic importance for maize crops. This species can cause 20% of total crop loss from early developmental stages to flowering [1]. The most common method for controlling this pest is the use of synthetic insecticides such as chlorpyrifos, carbaryl, and cypermethrin [2]; however, this has led to environmental harm, increased cost of application, insect resistance, lethal effects on non-target organisms, and direct toxicity to consumers [3]. Therefore, the development of low-cost and environmentally friendly alternatives [4] is important.

Researcher groups have identified different natural compounds extracted from plants [5-7], and microorganisms that act as biological control agents in economically important crops such as maize, sorghum, and rice [7-10].

Ruta graveolens L. (Rutaceae) is a plant that produces metabolites Figure 1: Percentage of S. frugiperda killed by R. graveolens leaf tissue extracts obtained with cytotoxic activity against microorganisms and insects [6, 7, 11, with different solvents (water, ethanol and ethyl acetate). Extracts were integrated and 12]. This species contains alkaloids, flavonoids, coumarins, homogenized at a concentration of 1 mg/mL of diet. Negative controls (diet only and diet + furanocoumarins, tannins, volatile oils, glycosides, sterols and DMSO 1%). Larvae were collected after 7 days of treatment. The words represent the statistical analysis (Tukey test P ≤ 0.05) between the means of each treatment. triterpenes [13-16]. Aqueous extracts of R. graveolens caused a mortality of 44% on S. frugiperda larvae [17], and essential oils of 1 mg/mL. Results show a significant difference among tested at high concentrations produced 100% mortality; the treatments (P ≤ 0.05) (Figure 1). The aqueous extract did not show identified compounds included nonanone (41.07%) and undecanone a significant difference with regard to negative controls (Figure 1); (45.89%) [18]. However, other extracts and metabolites of however, this extract caused a reduction in the weight of the larvae R. graveolens have not been evaluated for toxicity against (0.055 to 0.050 g), indicating a reduction in the growth index of S. frugiperda larvae. The aim of this work was to study the 8.36% in comparison with the control (data not shown). biological activity of R. graveolens extracts and metabolites (psoralen, 2-undecanone, and rutin) against S. frugiperda neonate According to previous reports, psoralen, 2-undecanone, and rutin larvae. have been found as the main metabolites of R. graveolens extracts [13, 15, 20, 21]. Therefore, these metabolites were evaluated on S. Initially, identification of R. graveolens was performed by frugiperda larvae. The bioassays of psoralen, 2-undecanone and amplification of the ITS region, corresponding to 700 bp [19]. The rutin metabolites showed that psoralen is highly toxic, killing 100% sample R. graveolens sequence was aligned with the corresponding of S. frugiperda larvae as cypermethrin insecticide (Figure 2). The sequence reported in GenBank (accession no. JQ230976.1); this second most toxic metabolite was 2-undecanone, which caused 50% sequence had a correspondence of 99% (Supplementary data). mortality. Rutin did not show a significant difference with regard to negative controls (diet only and diet + DMSO 1%) (Figure 2). Some Afterward, acuose, ethanolic and ethyl acetate extracts from R. authors have documented that rutin by itself does not have activity, graveolens were obtained and biologically evaluated on S. but in combination with other flavonoids, its biological activity may frugiperda larvae. We found that ethyl acetate and ethanol extracts increase [22]. caused a mortality of 94% and 78%, respectively, at a concentration 1956 Natural Product Communications Vol. 10 (11) 2015 Ayil-Gutiérrez et al.

Table 1: Metabolite concentration in R. graveolens leaf tissue (µmoles mg-1 DW) a, obtained with three different solvents.

Solvent Psoralen (SE±) b Rutin (SE±) b 2-undecanone (SE ±) b Ethyl acetate 3.6 0.2 0.001 0.000 87.9 6.1 Ethanol 3.0 0.04 0.02 0.003 86.2 9.7 Water 0.2 0.03 0.02 0.001 0.0 0.0 a Concentration of metabolites µmoles mg-1/DW (Dry weight). b Standard error (SE ±).

Also, a correlation between the decrease in metabolite concentration and mortality was observed. Therefore, we suggest that the toxic potential of ethyl acetate, and ethanolic extracts could be caused by high concentrations of psoralen and 2-undecanone. Additionally, our information indicates that low concentrations of psoralen, compared with 2-undecanone, are sufficient to be lethal against S. frugiperda.

Conclusions: In this work, ethyl acetate extract from R. graveolens Figure 2: Percentage of S. frugiperda killed by standard metabolites. Metabolites (psoralen, leaf tissue showed the highest percentage of mortality against S. 2-undecanone and rutin) were integrated and homogenized at a concentration of 1 mg/mL of diet. Negative controls (diet only and diet + DMSO 1%), and positive control (cypermethrin). frugiperda. Psoralen metabolite showed the same toxic effect as Larvae were collected after 7 days of treatment. The words represent the statistical analysis cypermethrin. Additionally, our results suggest that 2-undecanone (Tukey test P ≤ 0.05) between the means of each treatment after 7 days of treatment. could be used in the generation of new botanical insecticides against S. frugiperda. However, studies of its secondary effects and Researchers have reported that psoralen at a low concentration (2 mechanism of action are necessary. µmoles/mL) in celery inhibits the growth of pathogens such as Botrytis cinerea, Alternaria alternata and Sclerotinia sclerotiorum Experimental [23], while high concentrations (587.2 µmoles/mL) cause a mortality of up to 80% of Leptinotarsa decemlineata (Say) larvae Molecular identification of R. graveolens: Extraction of DNA [24]. Additionally, it inhibits microbial activity [25], and is involved from leaves (12 mg) was performed with the Wizard® Genomic in physiological [26] and molecular responses [27, 28]. In humans, DNA Purification Kit, (A1120, Promega Corp., Madison, WI). PCR psoralen has been widely used orally for psoriasis; however, it has was performed using the primers ITS1-Fwd (5’- resulted in adverse effects, including skin cancer after long-term use TCCGTAGGTGAACCTGCGG-3’) and ITS4-Rev (5’- [27, 29, 30] discussing its potential use as a bioinsecticide [31-33]. TCCTCCGCTTATTATTGATATGC-3’). The PCR assay was However, KINGBO® a botanical insecticide containing psoralen, performed with 12.5 μL of GoTaq Green Master Mix (2X) (M7122, has been used in laboratory bioassays against larvae (Tetranychus Promega Corp.), 1 µl of each oligonucleotides (5 µM) and 1 µl of urticae Koch) in a combination (0.2% oxymatrine + psoralen 0.4%) genomic DNA (25 ng) in a final volume of 25 µL. PCR conditions were as follows: 94°C for 5 min, followed by 35 cycles of 95°C for with a LC50= 6.88 µL/L [33, 34]. Taking into account the work and criteria of different authors in the use of psoralen, we cannot discard 30 s, 58°C for 30 s, and 72°C for 1 min, and final step of 72°C for 7 the use of psoralen as a botanical insecticide. min. The product was direct sequenced on the 3130 Genetic Analyzer (Applied Biosystems, HITACHI Tokyo, Japan) with ABI In the case of 2-undecanone, it has a significant role in the glandular PRISM® BigDye® Terminator v3.1 Cycle Sequencing Kits (P/N trichomes of Lycopersicon hirsutum f. glabratum [35]. It acts as a 4336917, Applied Biosystems, Foster City, CA). The sequences defense mechanism against herbivorous insects [36] and as a were assembled using SeqMan software of the LaserGene 8 repellent against various arthropods [37-39]. The use of 2- package (DNASTAR, Madison, WI), and analyzed with Blast from undecanone as an insect repellent against various arthropods is GenBank (www.ncbi.nlm.gov) (see details in Supplementary data). relatively new [38, 39] and it has been shown that these properties occur at high concentrations [37]. Also, it was recently shown that Extraction: Fresh leaf tissue (100 g) was obtained from R. 2-undecanone can act as an olfactory agonist or antagonist, graveolens. Collected material was washed, dried at 25°C for 30 modulating odorant receptor activity [40]. This information min, and ground (Osterizer, 450-10) for 5 min. For each treatment, suggests that in approximately 50% of the larvae of S. frugiperda, 100 mL of extraction solvent was added 3 times (ultrapure water; Milli-Q® ZMQS6V001, ethanol; Reproquifin PQF® 10-333, ethyl 2-undecanone modulates odorant receptor activity, causing larvae ® not to feed, which resulted in a weight loss of 8.6%. acetate; Reproquifin PQF , R-004) every 24 h for 3 days and kept in the dark at 25°C to recover the soluble phase. After the solvent Finally, to establish a correlation between biological activity and the was added, the mixture was stirred for 1 min. The mixture was then presence of metabolites in extracts of R. graveolens, the conditions filtered using Whatman #1 paper and afterwards transferred to a for detection and quantification of 2-undecanone, psoralen and rutin round-bottom flask (250 mL) and placed in a rotary evaporator at by HPLC and GC were established. The retention times for the 55°C and 180 rpm. The extract concentrate was stored at 4°C in metabolites were 24.62, 11.17, and 5.99 min, respectively. In the darkness until use. One mg dry weight (DW) sample was extracts analyzed, 2-undecanone was the metabolite with the resuspended in 1 mL of methanol and passed through a Millipore highest concentration, followed by psoralen and rutin (Table 1). A filter (0.22 µM) for subsequent analysis. comparison of the amount of each metabolite present in the extracts suggested that each compound could be extracted with a specific Metabolite quantification: High-Performance Liquid solvent. The most efficient solvent was ethyl acetate, which Chromatography (HPLC) was used to determine the concentration quantified high levels of 2-undecanone and psoralen. In of psoralen and rutin. The calibration curve for each standard phytochemical analysis, it has been reported that the concentrations metabolite was performed using psoralen (Sigma Aldrich P8399), depend on the polarity of the solvent and the extraction parameters and rutin (Rutin hydrate, Sigma Aldrich R5143). The retention time [41]. of each compound was used to compare the retention time of the compounds present in each extract. The chromatographic system Metabolites against Spodoptera frugiperda Natural Product Communications Vol. 10 (11) 2015 1957

(Agilent Technologies 1100) consisted of a quaternary system of were dissolved in 100 µL of DMSO 1%, and 2-undecanone was pumps (Agilent Technologies G1310A) connected to an automated dissolved directly in the diet. Extracts and standard metabolites sample injector (Agilent Technologies G1313A). Psoralen and rutin were integrated and homogenized in diet at a concentration of 1 were detected using a wavelength of 254 nm. The injected samples mg/mL, and 5 mL of the mixture was dispensed in plastic cups were detected with an ultraviolet detector (Agilent Technologies (p100-100, SOLO). Controls were prepared in the same way. One G1314A), and a reverse phase C18 column (Kromasil 5 μm, 4.6 mm neonate larva was transferred with a camel hair brush to one cup. inner diameter × 250 mm). For detection of psoralen, the mobile Twenty-five cups were placed in a paper bag and incubated for phase was MeOH/H2O (25:75) and for rutin, MeOH/H2O (95:5). 10:14 h; light/dark at 27 ± 1°C and 65 ± 5% RH. Bioassay was The flow rate for all samples was 0.5 mL/min. The column performed in triplicate totaling 75 larvae per treatment; mortality temperature was kept constant at 25°C. Solvents used were was recorded 7 days after treatment. Growth inhibition was previously degassed (ultrapure water; Milli-Q® ZMQS6V001, calculated accordingly [42]. ethanol; Fermont H6122, ethyl acetate; Reproquifin, R-004). Statistical analysis: Data were analyzed and plotted with An Agilent 7890A series Gas Chromatograph (GC) system SAS/STAT® (Statistical Analysis Software) and Origin 9.1 equipped with a hydrogen flame ionization detector was applied for Software (Data Analysis and Graphing Software). An analysis of quantitative analysis of 2-undecanone (Sigma Aldrich W309311). variance (ANOVA) was made and the degree of significance Separation was achieved with an Agilent HP-INNOWAX column between the mean values was determined using the Tukey test with (30 m × 0.530 mm, 1.00 μm), Agilent Technologies. The carrier gas P values ≤ 0.05 being considered significant. was nitrogen with a flow of 2 mL/min. The oven temperature was programmed at 60°C for 5 min, with a rise of 5°C/min up to 210°C Supplementary data: Details on the amplification and aligned ITS and held for 5 min. The temperature of the injector and detector sequences of R. graveolens. were set at 150°C and 250°C. The split less injection volume was 2 μL. A stock solution of 2-undecanone was prepared in ethyl Acknowledgments - This work was supported by the Secretary of acetate at a concentration of 1 mg/mL and stored at 4°C before use. Research and Postgraduate Studies of the Instituto Politécnico Nacional (SIP-IPN; 20151387 to Gildardo Rivera). Gildardo Rivera Bioassays: S. frugiperda neonate larvae were provided by the insect Sánchez and Ninfa M. Rosas García wish to thank the financial rearing area of the CBG-IPN. Bioassays were conducted support received from the Comisión de Operación y Fomento de with neonate larvae on an artificial diet. Nine treatments were Actividades Académicas (COFAA- Instituto Politécnico Nacional), tested: aqueous, ethanolic, and ethyl acetate extracts, negative and the Programa de Estímulos al Desempeño de los Investigadores controls (diet only and diet + DMSO 1%; Sigma Aldrich P-5879), (EDI- Instituto Politécnico Nacional). Benjamin A. Ayil-Gutiérrez positive controls (cypermethrin; IQC, S.A. de C.V.), and standard was supported by a scholarship from the National Council for metabolites: psoralen, 2-undecanone, and rutin. Psoralen and rutin Science and Technology (CONACyT; 290847).

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Natural Product Communications Vol. 10 (11) 2015 Published online (www.naturalproduct.us)

Volatile Constituents from the Flowers of Spathodea campanulata from the Venezuelan Andes

Silvana Villarreal, Deisy Jaimez, Sindy Moreno, Luis B. Rojas, Alfredo Usubillaga and María Rodríguez 1999

Composition and Variability of the Essential Oil of the Flowers of Lavandula stoechas from Various Geographical Sources Salvatore La Bella, Teresa Tuttolomondo, Giacomo Dugo, Giuseppe Ruberto, Claudio Leto, Edoardo M. Napoli, Angela Giorgia Potortì, Maria Rita Fede, Giuseppe Virga, Raffaele Leone, Eleonora D’Anna and Mario Licata 2001

Antioxidant and Anti-inflammatory Activities of Essential Oil and Extracts of Piper miniatum Wan Mohd Nuzul Hakimi Wan Salleh, Mohd Fariz Kammil, Farediah Ahmad and Hasnah Mohd Sirat 2005

Potential Skin Regeneration Activity and Chemical Composition of Absolute from Pueraria thunbergiana Flower Do-Yoon Kim, Kyung-Jong Won, Dae-Il Hwang, Seok Won Yoon, Su Jin Lee, Joo-Hoon Park, Myeong Sik Yoon, Bokyung Kim and Hwan Myung Lee 2009

Composition, in vitro Cytotoxicity, and Anti-mildew Activities of the Leaf Essential Oil of Machilus thunbergii from Taiwan

Yu-Chang Su, Kuan-Ping Hsu, Shu-Ching Li and Chen-Lung Ho 2013 Natural Product Communications Vol. 10 (11) 2015 Published online (www.naturalproduct.us)

Original Paper

Spasmolytic Activity of Carvone and Limonene Enantiomers Damião Pergentino de Sousa, Rafael Ferreira Mesquita, Luciano Augusto de Araújo Ribeiro and Julianeli Tolentino de Lima 1893

New Glycosides and Trypanocidal Metabolites from Vangueria edulis Shaymaa M. M. Mohamed, Khaled M. Elokely, Enaam Y. Bachkeet, Soad A. L. Bayoumi, Vincenzo Carnevale, Michael L. Klein, Stephen J. Cutler and Samir A. Ross 1897

Constituents of the Stem of Nauclea orientalis Phan Thi Anh Dao, Tran Le Quan and Nguyen Thi Thanh Mai 1901

Deodarone Isomers in Cedrus atlantica Essential Oils and Tar Oils Anne Marie Nam, Ange Bighelli, Mohamed Ghanmi, Badr Satrani, Joseph Casanova and Félix Tomi 1905

A New Trinor-guaiane Sesquiterpene from an Indonesian Soft Coral Anthelia sp. Novriyandi Hanif, Anggia Murni, Marie Yamauchi, Masahiro Higashi and Junichi Tanaka 1907

A New Cytotoxic Gymnomitrane Sesquiterpene from Ganoderma lucidum Fruiting Bodies Pham Thanh Binh, Dimitri Descoutures, Nguyen Hai Dang, Nguyen Phuong Dai Nguyen, and Nguyen Tien Dat 1911

A New Isocyanosesquiterpene from the Nudibranch Phyllidiella pustulosa Takahiro Jomori, Takahiro Shibutani, Peni Ahmadi, Toshimasa Suzuka and Junichi Tanaka 1913

Antimicrobial Diterpenes from Azorella Species Against Gram-Positive Bacteria Viviana Donoso, Mitchell Bacho, Solange Núñez, Juana Rovirosa, Aurelio San-Martín and Sergio Leiva 1915

A Novel Norclerodane Diterpenoid from the Roots of Croton crassifolius Zhan-Xin Zhang, Hui-Hong Li, Gai-Xia Fan, Zheng-Yu Li, Le-Le Dong, Hong-Yu Li and Dong-Qing Fei 1917

Production of Triterpenoid Sapogenins in Hairy Root Cultures of Silene vulgaris Yeon Bok Kim, Darwin W. Reed and Patrick S. Covello 1919

Extraction and Isolation of Antineoplastic Pristimerin from Mortonia greggii (Celastraceae) Luis Alberto Mejía-Manzano, Bertha A. Barba-Dávila, Janet A. Gutierrez-Uribe, Edgardo J. Escalante-Vázquez and Sergio O. Serna-Saldívar 1923

Bioassay-guided Isolation of Antiproliferative Triterpenoids from Euonymus alatus Twigs Hee Rae Kang, Hee Jeong Eom, Seoung Rak Lee, Sang Un Choi, Ki Sung Kang, Kang Ro Lee and Ki Hyun Kim 1929

Two New Triterpenoidal Saponins from Roots of Pachystela msolo Roland N. Ache, Turibio K. Tabopda, Samuel O. Yeboah and Bonaventure T. Ngadjui 1933

The Influence on LPS-Induced ROS Formation in Macrophages of Capelloside A, a New Steroid Glycoside from the Starfish Ogmaster capella Natalia V. Ivanchina, Alla A. Kicha, Timofey V. Malyarenko, Anatoly I. Kalinovsky, Ekaterina S. Menchinskaya, Evgeny A. Pislyagin and Pavel S. Dmitrenok 1937

Steroidal Saponins from the Mesocarp of the Fruits of Raphia farinifera (Arecaceae) and their Cytotoxic Activity Léon A. Tapondjou, Kristina J. Siems, Stefan Böttger and Matthias F. Melzig 1941

Bromotyrosine Alkaloids with Acetylcholinesterase Inhibitory Activity from the Thai Sponge Acanthodendrilla sp. Natchanun Sirimangkalakitti, Opeyemi J. Olatunji, Kanokwan Changwichit, Tongchai Saesong, Supakarn Chamni, Pithi Chanvorachote, Kornkanok Ingkaninan, Anuchit Plubrukarn and Khanit Suwanborirux 1945

Ircinal E, a New Manzamine Derivative from the Indonesian Marine Sponge Acanthostrongylophora ingens Mousa AlTarabeen, Georgios Daletos, Weaam Ebrahim, Werner E. G. Müller, Rudolf Hartmann, Wenhan Lin and Peter Proksch 1951

Ruta graveolens Extracts and Metabolites against Spodoptera frugiperda Benjamín A. Ayil-Gutiérrez, Jesús M. Villegas-Mendoza, Zuridai Santes-Hernández, Alma D. Paz-González, Maribel Mireles-Martínez, Ninfa M. Rosas-García and Gildardo Rivera ` 1955

A New Isoflavone Apioglucoside from the Roots of Dalbergia spinosa Raja Radha , Vairathevar Sivasamy Vasantha and Kasi Pitchumani 1959

Antioxidant and α-Glucosidase Inhibitory Properties and Chemical Profiles of Moroccan Propolis Milena Popova, Badiaa Lyoussi, Smail Aazza, Dulce Antunes, Vassya Bankova and Graça Miguel 1961

A Novel Acylated Anthocyanin with a Linear Trisaccharide from Flowers of Convolvulus althaeoides Luis Cabrita 1965

Bioactive Xanthones from Cratoxylum cochinchinense Achara Raksat, Tawanun Sripisut and Wisanu Maneerat 1969

A New 3-Prenyloxypsoralen from the Raw Fruits of Aegle marmelos and its Cytotoxic Activity Widchaya Radchatawedchakoon, Suthep Bamrungsuk, Siriporn Namwijit, Nuttapon Apiratikul, Uthai Sakee and Boon-ek Yingyongnarongkul 1973

New Gallotannin and other Phytochemicals from Sycamore Maple (Acer pseudoplatanus) Leaves Lu Zhang, Zong-cai Tu, Tao Yuan, Hang Ma, Daniel B. Niesen, Hui Wang and Navindra P. Seeram 1977

Three New Chlorinated Cyclopentenols, Palmaenols A and B and Palmaetriol, from the Discomycete Lachnum palmae Yuka Tanabe, Takunori Matsumoto, Tsuyoshi Hosoya, Hiroshi Tomoda, Motoo Shiro and Hideyuki Shigemori 1981

Prebiotic Effects of Agave salmiana Fructans in Lactobacillus acidophilus and Bifidobacterium lactis Cultures Adriana Castro-Zavala, Bertha I. Juárez-Flores, Juan M. Pinos-Rodríguez, Rosa E. Delgado-Portales, Juan R. Aguirre-Rivera and Francisco Alcocer-Gouyonnet 1985

Synergy Effects of Three Plant Extracts on Protection of Gastric Mucosa Caihui Wang, Wen Su, Xingli Su, Guojun Ni, Tao Liu and Yi Kong 1989

Aloe arborescens Extract Protects IMR-32 Cells against Alzheimer Amyloid Beta Peptide via Inhibition of Radical Peroxide Production

Maria Elisabetta Clementi, Giuseppe Tringali, Doriana Triggiani and Bruno Giardina 1993

Volatile Constituents of Three Piper Species from Vietnam Le D. Hieu, Tran M. Hoi, Tran D. Thang and Isiaka A. Ogunwande 1997 Natural Product Communications 2015 Volume 10, Number 11

Contents

Re-Discovery of the Plant Kingdom as a Valuable Source of Novel Drugs (Guest Editor: Francesco Epifano)

Original Paper

Antimicrobial Activity of neo-Clerodane Diterpenoids isolated from Lamiaceae Species against Pathogenic and Food Spoilage Microorganisms Petko Bozov, Tania Girova, Natalia Prisadova, Yana Hristova and Velizar Gochev 1797 Study of an Acid-Free Technique for the Preparation of Glycyrrhetinic Acid from Ammonium Glycyrrhizinate in Subcritical Water Anna V. Lekar, Sergey N. Borisenko, Elena V. Vetrova, Olga V. Filonova, Elena V. Maksimenko, Nikolai I. Borisenko and Vladimir I. Minkin 1801

New Flavonol Glycoside from the Leaves of Ventilago africana Diane Patricia Apie Gossan, Abdulmagid Alabdul Magid, Philomène Akoua Yao-Kouassi, Damien Le Faucheur, Antoine Ahibo Coffy, Dominique Harakat and Laurence Voutquenne-Nazabadioko 1805

Change in the Chemical Profile of Mangifera indica Leaves after their Metabolism in the Tropidacris collaris Grasshopper Rodolfo R. da Silva, Marcílio M. Moraes, Claudio A. G. Camara and Clécio S. Ramos 1809

Complexes of Lapachol and Lawsone with Lanthanides Salvatore Genovese, Vito Alessandro Taddeo, Francesco Epifano and Serena Fiorito 1811

Synthesis of the Furan Nucleus Promoted by Ytterbium Triflate Vito Alessandro Taddeo, Salvatore Genovese, Francesco Epifano and Serena Fiorito 1813

Analysis of Organic Acids, Deacetyl Asperulosidic Acid and Polyphenolic Compounds as a Potential Tool for Characterization of Noni (Morinda citrifolia) Products Miroslava Bittová, Dita Hladůvková, Vendula Roblová, Stanislav Kráčmar, Petr Kubáň and Vlastimil Kubáň 1817

Antioxidant Activity and Polyphenol Content of Some Brazilian Medicinal Plants Exploiting the Formation of the Fe(II)/2,2'-bipyridine Complexes Waila Evelyn Lima Santana, Cecilia Verônica Nunez and Horacio Dorigan Moya 1821

Reactive Nitrogen Species Scavenging Capacity of Aqueous and Ethanolic Extracts from Galinsoga parviflora and G. quadriradiata Herbs Marta Rogowska, Siniša Srečec and Agnieszka Bazylko 1825

Combination of Antioxidants from Different Sources Could Offer Synergistic Benefits: A Case Study of Tea and Ginger Blend Solomon A. Makanjuola, Victor N. Enujiugha, Olufunmilayo S. Omoba and David M. Sanni 1829

Lipid Metabolites from the Mushroom Meripilus giganteus Francesca Cateni, Tiziano Altieri, Marina Zacchigna, Giuseppe Procida, Jelena Zilič, Dušan Žigon and Angelo Cichelli 1833

HPLC Analysis, Antioxidant, Anti-inflammatory and Xanthine Oxidase Inhibitory Activity of Cudrania tricuspidata Shivraj Hariram Nile and Doo Hwan Kim 1839

Renoprotective Effects, Protein Thiols and Liver Glycogen Content of Alloxan-induced Diabetic Rats Treated with Different Fractions of Heartwood of Pterocarpus marsupium Vinutha Bhat and B Shivananda Nayak 1843

Medicinal Plants Used by a Mbyá-Guarani Tribe Against Infections: Activity on KPC-Producing Isolates and Biofilm-Forming Bacteria Clara Lia Costa Brandelli, Vanessa Bley Ribeiro, Karine Rigon Zimmer, Afonso Luís Barth, Tiana Tasca and Alexandre José Macedo 1847

Accounts/Reviews

Chemistry and Pharmacognosy of the Genus Durio Rudiyansyah, Kanda Panthong and Mary J Garson 1853

General Characteristics, Phytochemistry and Pharmacognosy of Lippia sidoides Luiz Gustavo de L. Guimarães, Maria Laura M. da Silva, Paula Campos J. Reis, Maria Tereza R. Costa and Lívia L. Alves 1861

Poplar-type Propolis: Chemical Composition, Botanical Origin and Biological Activity Petar Ristivojević, Jelena Trifković, Filip Andrić and Dušanka Milojković-Opsenica 1869

Activities of Tannins – From In Vitro Studies to Clinical Trials Elwira Sieniawska 1877

Organoselenium Compounds as Phytochemicals from the Natural Kingdom Hanane Achibat, Nohad A AlOmari, Federica Messina, Luca Sancineto, Mostafa Khouili and Claudio Santi 1885

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