bluuebunny/crossref_metadata_2025 huggingface dataset:
Inhibition of Soybean 15-Lipoxygenase by Naturally Occurring Acetophenones and Derricidin
Authors: Taddeo Vito Alessandro , Epifano Francesco , Genovese Salvatore , Fiorito Serena
Published: March 2019

Three selected naturally occurring oxyprenylated secondary metabolites, namely 2-hydroxy4-isopentenyloxyacetophenone (1), 4-geranyloxy-2-hydroxyacetophenone (2), 4-farnesyloxyacetophenone (3), and derricidin (4) were synthesized and their inhibitory potency against soybean 15-lipoxygenase evaluated. Compounds 1 and 4 showed the most potent inhibitory activity with IC50 values of 2.5 μM and 0.6 μM.
Cytotoxic Compounds from Endemic Arnebia purpurea
Authors: Yuzbasioglu Merve , Kuruuzum-Uz Ayse , Guvenalp Zuhal , Simon András , Tóth Gábor , Harput U. Sebnem , Kazaz Cavit , Bilgili Bilgehan , Duman Hayri , Saracoglu Iclal , Demirezer L. Omur
Published: March 2019

Phytochemical studies of the roots and aerial parts of endemic Arnebia purpurea S. Erik & H. Sumbul resulted in the isolation and characterization of four naphthoquinones [isovalerylalkannin (1), α-methyl- n-butanoyl alkannin (2), acetylalkannin (3), and alkannin (4)], a triterpene derivative [3- O-acetyl-oleanolic acid (5)], a steroid [β-sitosterol (6)], three flavonoid glycosides [isorhamnetin-3- O-rutinoside (7), kaempferol-3- O-rutinoside (8), kaempferol 3- O-(5″-acetyl) apiofuranoside 7- O-rhamnopyranoside (9)] and a phenolic acid [rosmarinic acid (10)]. 3- O-Acetyl-oleanolic acid, isorhamnetin-3- O-rutinoside, kaempferol-3- O-rutinoside, and kaempferol 3- O-(5″-acetyl) apiofuranoside 7- O-rhamnopyranoside are reported from an Arnebia species for the first time. Cytotoxic activities on L929 murine fibrosarcoma cell line of the isolated compounds were investigated using MTT assay. Naphthoquinones (1–4) showed intermediate cytotoxic activity in comparison with the standard, doxorubicin.
A New Citrinin Dimer Isolated from Aspergillus terreus StrainZDF21
Authors: Dame Zerihun T. , Suwannarach Nakarin , Lumyong Saisamorn , Laatsch Hartmut
Published: March 2019

Dicitrinin E (1), a new citrinin dimer, together with the known metabolites, dicitrinin A (2), citrinin (3), and fumitremorgin C (4), were isolated from the broth culture of Aspergillus terreus strain ZDF21. The structure of dicitrinin E (1) was elucidated through detailed analysis of 1D and 2D NMR experiments, CD and mass spectra. The cytotoxicity of 1 was tested against larvae of Artemia salina.
New Bicyclo-spartinols from the Marine-derived Fungus Phaeosphaeria spartinae
Authors: Elsebai Mahmoud Fahmi , Maddah Fayrouz El , Kehraus Stefan , König Gabriele M.
Published: March 2019

Investigation of the marine-derived fungus Phaeosphaeria spartinae, an endophyte of the marine alga Ceramium sp., led to the isolation of the unprecedented polyketides 1 and 2. The structures of these compounds were established from extensive spectroscopic analyses.
Comparison of the Chemical Composition of Valeriana parviflora Essential Oils Collected in the Venezuelan Andes in two Different Seasons
Authors: Fernández Sammy , Rondón María , Rojas Janne , Morales Antonio , Rojas-Fermin Luis
Published: March 2019

The essential oils obtained by hydrodistillation of the aerial parts of Valeriana parviflora (Trevir) BM Vadillo, an endemic species of the Venezuelan Andes, collected from the same location in two different seasons (dry and rainy) of the year, were analyzed by GC/MS. The essential oil obtained during the dry season showed linalool (11.9%), eugenol (8.9%), p-menth-1-en-9-al (8.7%) and α-terpineol (7.7%) as main components, while the oil obtained from the rainy season collection showed o-xylol (16.2%), 3-methyl isovaleric acid (10.6%) and geranial (9.5%) as major compounds. Some of the differences in the composition of these oils might be due to the climatic conditions at the time of harvesting.
Antimicrobial Activity and Chemical Composition of the Essential Oils of Portuguese Foeniculum vulgare Fruits
Authors: Mota Ana S. , Martins M. Rosário , Arantes Sílvia , Lopes Violeta R. , Bettencourt Eliseu , Pombal Sofia , Gomes Arlindo C. , Silva Lúcia A.
Published: March 2019

The aim of this study was to investigate the chemical composition and antimicrobial activity of essential oils obtained by hydrodistillation from fruits of six fennel accessions collected from wild populations occurring in the centre and south of Portugal. Composition of essential oils was established by Gas Chromatography-Flame Ionization Detector (GC-FID) and Gas Chromatography-Mass Spectrometry (GC-MS) analysis. The obtained yields of the essential oils were found to vary greatly in the range of 1.1 to 2.9% (v/w) and the chemical composition varied with the region of collection. A total of 16 compounds were identified. The main compounds were fenchone (16.9 – 34.7%), estragole (2.5 – 66.0%) and trans-anethole (7.9 – 77.7%). The percentages of these three main compounds were used to determine the relationship between the different oil samples and to group them into four different chemotypes: anethole/fenchone; anethole; estragole and anethole/estragole. Antifungal activity of essential oils was evaluated against six food spoilage fungi: Aspergillus niger, A. japonicus, A. oryzae, Fusarium oxysporum, Rhizophus oryzae and R. stolonifer. Antibacterial activity was assessed against three Gram-positive strains: Enterococcus faecalis ATCC 29212, Staphylococcus epidermidis ATCC 12228 and S. aureus ATCC 28213; and against six Gram-negative strains: Escherichia coli ATCC 25922; Morganella morganii LFG 08; Proteus mirabilis LFG 04; Salmonella enteritidis LFG 05; S. entiritidis serovar typhimurium LFG 06 and Pseudomonas aeruginosa ATCC 27853 by the disc diffusion agar method; the minimal inhibitory concentration (MIC) was determined using the broth macro-dilution method. The MIC values varied from 62.5 ( E. coli ATCC 25922) to 2000 μg/mL ( P. aeruginosa ATCC 27853).
Larvicidal Activity against Aedes Aegypti of Foeniculum Vulgare Essential Oils from Portugal and Cape Verde
Authors: Rocha Diara Kady , Matos Olivia , Novo Maria Teresa , Figueiredo Ana Cristina , Delgado Manuel , Moiteiro Cristina
Published: March 2019

Dengue is a potentially fatal mosquito-borne infection with 50 million cases per year and 2.5 billion people vulnerable to the disease. This major public health problem has recurrent epidemics in Latin America and occurred recently in Cape Verde and Madeira Island. The lack of anti-viral treatment or vaccine makes the control of mosquito vectors a high option to prevent virus transmission. Essential oil (EO) constituents can affect insect's behaviour, being potentially effective in pest control. The present study evaluated the potential use of Foeniculum vulgare (fennel) EO in the control of the dengue vector Aedes aegypti. EOs isolated from fennel aerial parts collected in Cape Verde and from a commercial fennel EO of Portugal were analysed by NMR, GC and GC-MS. trans-Anethole (32 and 30%, respectively), limonene (28 and 18%, respectively) and fenchone (10% in both cases) were the main compounds identified in the EOs isolated from fennel from Cape Verde and Portugal, respectively. The larvicidal activity of the EOs and its major constituents were evaluated, using WHO procedures, against third instar larvae of Ae. aegypti for 24 h. Pure compounds, such as limonene isomers, were also assayed. The lethal concentrations LC50, LC90 and LC99 were determined by probit analysis using mortality rates of bioassays. A 99% mortality of Ae. aegypti larvae was estimated at 37.1 and 52.4 μL L−1 of fennel EOs from Cape Verde and Portugal, respectively. Bioassays showed that fennel EOs from both countries displayed strong larvicidal effect against Ae. aegypti, the Cape Verde EO being as active as one of its major constituents, (-)-limonene.
Chemical Constituents of the Genus Polygonatum and their Role in Medicinal Treatment
Authors: Zhao Xueying , Li Ji
Published: March 2019

Polygonatum is a famous traditional Chinese medicine that is widely used in China, Korea and Japan. In the last decade, constituents of the genus have been reported including steroidal saponins, flavones, alkaloids, lignins, amino acids and carbohydrates, some of which show biological properties such as antiviral and antitumor activity, variable effects on the immune system and anticoagulant activity. In addition, some findings provide novel evidence that Polygonatum species may contain potential anti-tumor and anti-viral proteins for possible medical application and large-scale pharmaceutical production. In this review, we focus on the updated research of the chemical constituents of Polygonatum including polysaccharides, steroidal saponins, flavonoids and lectins, and their potential therapeutic roles.
Unraveling the Biosynthesis of Pilocarpine in Pilocarpus microphyllus
Authors: Sawaya Alexandra Christine Helena Frankland , Costa Yanna Dias , Mazzafera Paulo
Published: March 2019

Pilocarpine is found exclusively in species of Pilocarpus and the presence of other imidazole alkaloids has been reported in several species of the genus. Pilocarpine has several important pharmaceutical applications. Although several imidazole alkaloids related to pilocarpine have been reported in the previous years, little is still known about its biosynthetic route. At most, histidine has been reported as the precursor of pilocarpine. Based on our own previous reports and in an experiment where pilocarpine and related alkaloids (pilosine, trachyllophiline and anhydropilosine) were supplied to P. microphyllus leaves and the alkaloid profile analyzed by UPLC-MS, we suggest a biosynthesis pathway for pilocarpine. Further experiments using labeled precursors associated with transcriptome data may allow us to understand the whole biosynthesis pathway and its genetic control.
Transcriptomic Evaluation of Plant Growth Inhibitory Activity of Goniothalamin from the Malaysian Medicinal Plant Goniothalamus andersonii
Authors: Wasano Naoya , Takemura Tomoko , Ismil Raihan , Bakar Baki , Fujii Yoshiharu
Published: March 2019

Goniothalamin produced by the Malaysian medicinal plant, Goniothalamus andersonii J. Sinclair, strongly inhibits plant growth. However, its mode of action has not been characterized at the gene expression level. We conducted DNA microarray assay to analyze the changes in early gene responses of Arabidopsis thaliana seedlings. After a 6-h exposure to goniothalamin, we observed an upregulation of genes highly associated with heat response, and 22 heat shock protein ( AtHSP) genes were upregulated more than 50 fold. Together with these genes, we observed upregulation of the genes related to oxidative stress and protein folding. Also, the genes related to cell wall modification and cell growth, expansin ( AtEXPA) genes, were significantly downregulated. The results suggested that goniothalamin induces oxidative stresses and inhibits the expression of cell wall-associated proteins resulting in growth inhibition of Arabidopsis seedlings.
A Protocol for Axenic Liquid Cell Cultures of a Woody Leguminous Mangrove, Caesalpinia crista, and their Amino Acids Profiling
Authors: Inoue Aya , Ogita Shinjiro , Tsuchiya Shinpei , Minagawa Reiko , Sasamoto Hamako
Published: March 2019

Callus induction, maintenance and protoplast cultures were achieved from immature seeds of a woody leguminous mangrove, Caesalpinia crista. Axenic cultures were possible during 1.5 months of pod storage in 0.1% benzalkonium chloride solution. Callus induction was achieved using 1 mL liquid medium in a 10 mL flat-bottomed culture tube. Protoplasts were isolated using Cellulase R10, Hemicellulase, and Driselase 20 in 0.6 M mannitol solution and sub-culturable calluses were obtained in 50 μL liquid medium using a 96-microplate method. The optimal hormonal concentration was 10 μM each of 2,4-dichlorophenoxyacetic acid and benzyladenine in liquid Murashige and Skoog's basal medium for both callus induction and maintenance, and protoplast cultures. Similarities and differences in amino acid profiles and culture conditions are discussed among woody mangrove species and non-mangrove leguminous species. Caesalpinia crista cultures were unique as they secreted a large amount of amino acids, including proline, into the liquid culture medium.
Identification of Octanal as Plant Growth Inhibitory Volatile Compound Released from Heracleum sosnowskyi Fruit
Authors: Mishyna Maryia , Laman Nikolai , Prokhorov Valery , Maninang John Solomon , Fujii Yoshiharu
Published: March 2019

Heracleum sosnowskyi Manden of the Apiaceae family is a malignant invasive plant in Eastern Europe, Belarus and Russia. The species is known for its prolific seed production, which has been linked to the plant's invasive success. The fruit also has a strong aroma, but the contribution of the fruit's volatile constituent to out-compete neighboring plants has not been fully established. In this study, fruit volatiles of H. sosnowskyi and conspecifics (i.e. H. asperum, H. lescovii, H. dissectum, H. hirtum) were identified by headspace gas chromatography-mass spectrometry (HS-GC-MS). Octyl acetate, octanol, octanal, hexyl isobutyrate, and hexyl-2-methyl butyrate were found to be the principal volatiles. Using authentic standards, the growth-inhibitory property of the individual compounds was assayed by the novel Cotton swab method. Assay results with lettuce ( Lactuca sativa) showed that octanal strongly inhibited seed germination and radicle elongation of seedlings. The results suggest that octanal may be the main contributor to the allelopathic activity of H. sosnowksyi fruits. Furthermore, the mixture of fruit volatiles from the invasive H. sosnowskyi more strongly delayed lettuce seedling elongation than the volatiles from fruits of the non-invasive H. asperum, H. lescovii, H. dissectum and H. hirtum. Thus, the present study is the first to demonstrate the possible involvement of fruit volatiles of Heracleum species in plant-plant interaction.
Identification of Safranal as the Main Allelochemical from Saffron (Crocus sativus)
Authors: Mardani Hossein , Sekine Takayuki , Azizi Majid , Mishyna Maryia , Fujii Yoshiharu
Published: March 2019

Dried parts of 75 medicinal plant species collected from different regions in Iran were assayed by the Dish Pack Method for volatile allelopathic activity, using Lactuca sativa (lettuce) as the test plant. The highest (60%) inhibition was observed for saffron (stigma of Crocus sativus), followed by Dracocephalum kotschyi, Solanum nigrum and Artemisia aucheri. Safranal was identified as the main chemical by Headspace Gas Chromatography-Mass Spectrometry (HS-GC-MS) analyses of saffron. Moreover, the EC50 of safranal was evaluated as 1.2 μg/L (ppb). This is the first report on allelopathic activity of safranal as a bioactive compound identified from saffron.
Low Caffeine Content in Novel Grafted Tea with Camellia sinensis as Scions and Camellia oleifera as Stocks
Authors: Deng Wei-Wei , Li Min , Gu Chen-Chen , Li Da-Xiang , Ma Lin-Long , Jin Yang , Wan Xiao-Chun
Published: March 2019

Caffeine, a purine alkaloid, is a major secondary metabolite in tea leaves. The demand for low caffeine tea is increasing in recent years, especially for health reasons. We report a novel grafted tea material with low caffeine content. The grafted tea plant had Camellia sinensis as scions and C. oleifera as stocks. The content of purine alkaloids was determined in the leaves of one-year-old grafted tea plants by HPLC. We also characterized caffeine synthase (CS), a key enzyme involved in caffeine biosynthesis in tea plants, at the expression level. The expression patterns of CS were examined in grafted and control leaves by Western blot, using a self-prepared polyclonal antibody with high specificity and sensitivity. The expression of related genes ( TCS1, tea caffeine synthase gene, GenBank accession No. AB031280; sAMS, SAM synthetase gene, AJ277206; TIDH, IMP dehydrogenase gene, EU106658) in the caffeine biosynthetic pathway was investigated by qRT-PCR. HPLC showed that the caffeine content was only 38% as compared with the non-grafted tea leaves. Immunoblotting analysis showed that CS protein decreased by half in the leaves of grafted tea plants. qRT-PCR revealed no significant changes in the expression of two genes in the upstream pathway ( sAMS and TIDH), while the expression of TCS1 was greatly decreased (50%). Taken together, these data revealed that the low caffeine content in the grafted tea leaves is due to low TCS1 expression and CS protein accumulation.
Involvement of Allelopathy in the Formation of Monospecific Colonies of Ferns
Authors: Kato-Noguchi Hisashi
Published: March 2019

Some fern species often dominate plant communities by forming large monospecific colonies. However, the potential mechanism for this domination of the ferns remains obscure. Many plants secrete a wide range of compounds into the rhizosphere and change the chemical and physical properties of the rhizosphere soil. Through the secretion of compounds, such as allelopathic substances, plants inhibit the germination and growth of neighboring plants to compete more effectively for the resources. Ferns contain a variety of secondary metabolites and some of those compounds are released from the ferns into the rhizosphere soil, either as exudates from living ferns or by decomposition of fern residues in sufficient quantities to affect the germination and growth of neighboring plants as allelopathic substances. Therefore, allelopathic chemical interaction of the ferns with neighboring plants may play an important role in the formation of the monospecific colonies of the ferns.
Plant Cell, Tissue and Organ Culture: The Most Flexible Foundations for Plant Metabolic Engineering Applications
Authors: Ogita Shinjiro
Published: March 2019

Significant advances in plant cell, tissue and organ culture (PCTOC) have been made in the last five decades. PCTOC is now thought to be the underlying technique for understanding general or specific biological functions of the plant kingdom, and it is one of the most flexible foundations for morphological, physiological and molecular biological applications of plants. Furthermore, the recent advances in the field of information technology (IT) have enabled access to a large amount of information regarding all aspects of plant biology. For example, sequencing information is stored in mega repositories such as the National Center for Biotechnology Information (NCBI), which can be easily accessed by researchers worldwide. To date, the PCTOC and IT combination strategy for regulation of target plant metabolism and the utilization of bioactive plant metabolites for commercial purposes is essential. In this review, the advantages and the limitations of these methodologies, especially regarding the production of bioactive plant secondary metabolites and metabolic engineering in target plants are discussed mainly from the phenotypic view point.
Natural Caryophyllane Sesquiterpenoids from Rumphella antipathies
Authors: Chung Hsu-Ming , Wang Wei-Hsien , Hwang Tsong-Long , Wu Yang-Chang , Sung Ping-Jyun
Published: March 2019

Two new natural caryophyllane-type sesquiterpenoids, 1 and 2, were isolated from the gorgonian coral Rumphella antipathies. Standard spectroscopic techniques were used to determine the structures of caryophyllanes 1 and 2.
New Laurene-type Sesquiterpene from Bornean Laurencia nangii
Authors: Kamada Takashi , Vairappan Charles Santhanaraju
Published: March 2019

We report the chemical composition of a population of Bornean Laurencia nangii Masuda. A new compound, neolaurene (1), along with five known metabolites, neolaurallene (2), 2,10-dibromo-3-chloro-α-chamigrene (3), deoxyprepacifenol (4), cycloelatanene B (5) and intricatetraol (6), were isolated and their chemical structures elucidated based on spectroscopic data. In addition, their cytotoxicity and antibacterial activity were evaluated.
Oxygenated Terpenes from Indo-Pacific Nudibranchs: Scalarane Sesterterpenes from Glossodoris hikuerensis and 12-Acetoxy Dendrillolide A from Goniobranchus albonares
Authors: Mudianta I. Wayan , White Andrew M. , Garson Mary J.
Published: March 2019

Two new scalarane sesterterpenes (1, 2) were characterized from an organic extract of a single specimen of the nudibranch Glossodoris hikuerensis collected from Bali. 12-Acetoxy dendrillolide A (10) was identified from specimens of Goniobranchus albonares, while dendrillolide A (11) was isolated both from G. albonares and its sponge diet. The structures and relative configuration of the new metabolites have been elucidated by analysis of their spectroscopic data.
Ergosterol of Cordyceps militaris Attenuates LPS Induced Inflammation in BV2 Microglia Cells
Authors: Nallathamby Neeranjini , Guan-Serm Lee , Vidyadaran Sharmili , Malek Sri Nurestri Abd , Raman Jegadeesh , Sabaratnam Vikineswary
Published: March 2019

Different solvent extracts of Cordyceps militaris stroma powder were tested for cell viability and inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS) triggered BV2 microglia cells. Chemical investigation of the ethyl acetate fraction resulted in an enriched ergosterol sub-fraction CE3. The BV2 cells showed no cytotoxic effects when treated with the ethyl acetate fraction and sub-fraction CE3 at concentrations of 0.1 μg/mL – 100 μg/mL compared with the control. At 10 μg/mL, the ethyl acetate fraction and sub-fraction CE3 had the highest reduction of 48.0% and 44.7% of nitric oxide production, respectively. The major compound in sub-fraction CE3 was ergosterol, identified by GCMS, and the purity was checked by HPLC. Further, the reduction of nitric oxide in LPS triggered BV2 cells was about three fold higher when compared with the control commercial ergosterol.
Synthesis and Antimicrobial Activities of 3-Methyl-β-Carboline Derivatives
Authors: Zhang Jiwen , Li Longbo , Dan Wenjia , Li Jian , Zhang Qianliang , Bai Hongjin , Wang Junru
Published: March 2019

The β-carboline alkaloids possess a diverse range of important biochemical effects and pharmacological properties. Sixteen 3-methyl-β-carboline derivatives were synthesized from indole formaldehyde and nitroethane via the Henry reaction, LAH/THF reduction, the Pictet-Spengler reaction and Pd/C/xylene oxidation, including four 1-substituted and twelve 9-substituted 3-methyl- β-carboline derivatives. The structures of all the derivatives were confirmed by 1H NMR, 13C NMR and ESI-MS. Most of these 3-methyl-β-carboline derivatives showed some antibacterial activity.
A Novel One-step Synthesis of Quinoline-2(1H)-thiones and Selones by Treating 3-Aryl-3-(2-aminophenyl)-1-propyn-3-ols with a Base and Elemental Sulfur or Selenium
Authors: Shimada Kazuaki , Izumi Hironori , Otashiro Koki , Noro Kensuke , Aoyagi Shigenobu , Takikawa Yuji , Korenaga Toshinobu
Published: March 2019

A one-step conversion of 3-aryl-3-(2-aminophenyl)-1-propyn-3-ols into quinoline-2(1 H)-thiones and quinoline-2(1 H)-selones was achieved only by treating the substrates with n-butyllithium and either elemental sulfur or selenium, respectively. The reactions were assumed to proceed through an intramolecular nucleophilic attack of the neighboring amino group to the plausible in situ generated reactive species related to chalcogenoketenes. The subsequent mCPBA oxidation of quinoline-2(1 H)-selones afforded quinolin-2(1 H)-ones in high yields.
Computational and Investigative Study of Flavonoids Active against Trypanosoma cruzi and Leishmania spp
Authors: Ribeiro Frederico F. , Junior Francisco J.B.M. , da Silva Marcelo S. , Scotti Marcus Tullius , Scotti Luciana
Published: March 2019

Flavonoid compounds active against Trypanosoma cruzi and Leishmania species were submitted to several methodologies in silico: docking with the enzymes cruzain and trypanothione reductase (from T. cruzi), and N-myristoyltransferase, dihydroorotate dehydrogenase, and trypanothiona reductase (from Leishmania spp). Molecular maps of the complexes and the ligands were calculated. In order to compare and evaluate the antioxidant activity of the flavonoids with their antiprotozoal activity, quantum parameters were calculated. Considering the energies, interactions, and hydrophobic surfaces calculated, the flavonoids chrysin dimethyl ether against T. cruzi, and ladanein against Leishmania sp. presented the best results. The antioxidant activity did not show any correlation with anti-parasitic activity; only chrysin and its dimethyl ether showed favorable anti-parasitic results. This study hopes to contribute to existing research on these natural products against these tropical parasites.
Regioselective Glycosylation of 3-, 5-, 6-, and 7-Hydroxyflavones by Cultured Plant Cells
Authors: Shimoda Kei , Kubota Naoji , Uesugi Daisuke , Fujitaka Yuuya , Okada Shouta , Tanigawa Masato , Hamada Hiroki
Published: March 2019

Regioselective glycosylation of 3-, 5-, 6-, and 7-hydroxyflavones was investigated using cultured plant cells of Eucalyptus perriniana and Phytolacca americana as biocatalysts. 3- and 7-Hydroxyflavones were practically glycosylated into the corresponding β-D-glucosides by E. perriniana and P. americana.
Water Extract of Mentha × villosa: Phenolic Fingerprint and Effect on Ischemia-Reperfusion Injury
Authors: Fialova Silvia , Veizerova Lucia , Nosalova Viera , Drabikova Katarina , Tekelova Daniela , Grancai Daniel , Sotnikova Ruzena
Published: March 2019

Qualitative analysis of the water extract of Mentha x villosa Huds. leaves was performed by liquid chromatography mass spectrometry (LC-MS/MS) and quantitative analysis was made by reverse-phase liquid chromatography coupled with photodiode array detection (LC-DAD). Sixteen phenolic compounds were identified and quantified consisting of 8 phenolic acids/derivatives and 8 flavonoid glycosides (quinic acid, chlorogenic acid, coumaroyl-hexoside, caffeic acid, coumaroylquinic acid, lithospermic acid, rosmarinic acid, salvianolic acid A, luteolin-7- O-glucuronide, luteolin-7- O-glucoside, luteolin-7- O-rutinoside, eriodictyol-7- O-rutinoside, apigenin-7- O-glucuronide, kaempferol-3- O-glucuronide, chrysoeriol-7- O-rutinoside, and hesperetin-7- O-rutinoside). Luteolin-7- O-rutinoside (25.6 ± 0.7 mg/g dry extract) and rosmarinic acid (17.9 ± 0.4 mg/g dry extract) were the most abundant. High antioxidant activity of this phenolic-rich water extract was confirmed in vitro by DPPH and ABTS tests and ex vivo in the ischemia-reperfusion injured rat superior mesenteric artery. Thus, the water extract of M. x villosa leaves seems to be a promising agent in prevention of tissue injury caused by oxidative stress.
Distribution and Taxonomic Significance of Secondary Metabolites Occurring in the Methanol Extracts of the Stonecrops (Sedum L., Crassulaceae) from the Central Balkan Peninsula
Authors: Stojanović Gordana S. , Jovanović Snežana Č. , Zlatković Bojan K.
Published: March 2019

The present study is engaged in the chemical composition of methanol extracts of Sedum taxa from the central part of the Balkan Peninsula, and representatives from other genera of Crassulaceae ( Crassula, Echeveria and Kalanchoe) considered as out-groups. The chemical composition of extracts was determined by HPLC analysis, according to retention time of standards and characteristic absorption spectra of components. Identified components were considered as original variables with possible chemotaxonomic significance. Relationships of examined plant samples were investigated by agglomerative hierarchical cluster analysis (AHC). The obtained results showed how the distribution of methanol extract components (mostly phenolics) affected grouping of the examined samples. The obtained clustering showed satisfactory grouping of the examined samples, among which some representatives of the Sedum series, Rupestria and Magellensia, are the most remote. The out-group samples were not clearly singled out with regard to Sedum samples as expected; this especially applies to samples of Crassula ovata and Echeveria lilacina, while Kalanchoe daigremontiana was more separated from most of the Sedum samples.
Enzymatic Synthesis of Quercetin Monoglucopyranoside and Maltooligosaccharides
Authors: Yasukawa Ryo , Moriwaki Natsumi , Uesugi Daisuke , Kaneko Fuya , Hamada Hiroki , Ozaki Shin-Ichi
Published: March 2019

Quercetin 3- O-β-monoglucopyranoside and quercetin 3- O-β-maltooligosaccharide were synthesized from quercetin using glucosyltransferase-3 from Phytolacca americana and cyclodextrin glucanotransferase.
Polyurethane Microstructures-a Good or Bad in vitro Partner for the Isoflavone Genistein?
Authors: Danciu Corina , Borcan Florin , Soica Codruta , Zupko Istvan , Csányi Erzsébet , Ambrus Rita , Muntean Delia , Sass Camelia , Antal Diana , Toma Claudia , Dehelean Cristina
Published: March 2019

In recent years polyurethane microstructures (PM) have gained increasing attention in the pharmaceutical field due to the importance of their practical application. Since finding that such a formulation with genistein could improve its applications, we have conducted a preliminary study regarding the in vitro antiproliferative (MCF7, MDA-MB-231 and T47D) and antimicrobial ( Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enteritidis (D), Bacillus subtilis, B. cereus, and Candida albicans) activity in order to test whether polyurethane micro structuresre present a good option for further modulation of genistein's bioavailability. It was concluded that the polyurethane micro structures are a bad in vitro partner for the isoflavone genistein.
Synthesis of Arecatannin A1 from Dimeric Epicatechin Electrophile
Authors: Suda Manato , Takanashi Kohki , Katoh Miyuki , Matsumoto Kiriko , Kawaguchi Koichiro , Kawahara Sei-Ichi , Fujii Hiroshi , Makabe Hidefumi
Published: March 2019

Synthesis of arrecatannin A1 (1) was accomplished from dimeric epicatechin electrophile, which was prepared by Zn(OTf)2 mediated self-condensation, and monomeric catechin nucleophile. The condensation was successfully worked using Yb(OTf)3 as a Lewis acid in good yield.
RP-HPLC-DAD-MSn Analysis and Butyrylcholinesterase Inhibitory Activity of Barbacenia blanchetii Extracts
Authors: Barbosa Jósquia S , Almeida Verônica M , Marçal Rosilene M , Branco Alexsandro
Published: March 2019

High-performance liquid chromatography (HPLC) coupled to a diode-array detector (DAD) and electrospray ionization mass spectrometry (MS) was applied for the separation and identification of phenolic compounds in the n-hexane, ethyl acetate and methanol crude extract of Barbacenia blanchetii. The MS, MSn and UV data together with chemosystematic evidence allowed the structural characterization of five compounds: tricin, chrysoeriol, epi-gallocatechin, kaempferol 3- O-glucoside and caffeoylquinic acid. At the same time, these extracts were evaluated against butyrylcholinesterase using Ellman's method. All extracts inhibited BuChE in a concentration-dependent form; however, the methanol extract showed a better effect that the other extracts. These compounds have been identified previously in the Velloziaceae family, but for the first time as constituents of B. blanchetii.
Anti-inflammatory, Antioxidant and Antimicrobial Activity Characterization and Toxicity Studies of Flowers of “Jarilla”, a Medicinal Shrub from Argentina
Authors: Moreno Alejandra , Nuño Gabriela , Cuello Soledad , Sayago Jorge E. , Alberto María Rosa , Zampini Catiana , Isla María Inés
Published: March 2019

Zuccagnia punctata Cav. (Fabaceae) is an Argentine medicinal aromatic shrub (jarilla pispito, puspus, lata and jarilla macho). The chalcones were identified as pigments responsible for the yellow color of the flowers. Hydroethanolic extracts were obtained both from fresh flowers and from flowers dried by lyophilization. The extracts were standardized by their phenolic and flavonoids content. Their fingerprints by HPLC-DAD indicated the presence of two chalcones as major compounds (2′,4′-dihydroxychalcone and 2′,4′-dihydroxy-3′-methoxychalcone). Both extracts showed the same total phenolic, non-flavonoid phenolic and flavonoid phenolic content and their phenolic profiles were similar. The polyphenolic extracts exhibited antioxidant (free radical scavenging and inhibitory activity on lipoperoxidation) and anti-inflammatory (inhibition of lipoxygenase and cyclooxygenase enzymes) activities. The flower extracts were active against six Candida species with MIC values between 60 and 120 μg GAE.mL−1 and were also active on methicillin-resistant Staphylococcus aureus (MIC: 250 μg GAE.mL−1) and Enterococcus faecalis (MIC: 500 μg GAE.mL−1). The extracts were neither toxic ( Artemia salina test) nor mutagenic (Ames test). Jarilla flowers could be considered as a new dietary supplement that could help to prevent pathologies associated with oxidative stress and the polyphenolic extract obtained from them could be considered as a standardized phytotherapeutic product with antimicrobial, antioxidant and anti-inflammatory activities.
Effect of Non-psychotropic Plant-derived Cannabinoids on Bladder Contractility: Focus on Cannabigerol
Authors: Pagano Ester , Montanaro Vittorino , di Girolamo Antonio , Pistone Antonio , Altieri Vincenzo , Zjawiony Jordan K. , Izzo Angelo A. , Capasso Raffaele
Published: March 2019

There are anecdotal reports that some Cannabis preparations may be useful for bladder dysfunctions. Here, we investigated the effect of a number of non-psychotropic phytocannabinoids, namely cannabidiol (CBD), cannabigerol (CBG), cannabidivarin (CBDV), Δ9-tetrahydrocannabivarin (THCV) and cannabichromene (CBC) on mouse bladder contractility in vitro. CBG, THCV, CBD and CBDV, but not CBC, at concentration ranging from 10−8 M to 10−4 M, decreased (with similar potency), the contractions induced by acetylcholine without significantly modifying the contractions induced by electrical stimulation. The rank order of efficacy was CBG=THCV>CBD>CBDV. In depth studies on CBG showed that the effect of this phytocannabinoid on acetylcholine-induced contractions was not affected by CB1 or CB2 receptor antagonists. Additionally, CBG also reduced acetylcholine-induced contractions in the human bladder.
In Cell Interactome of Oleocanthal, an Extra Virgin Olive Oil Bioactive Component
Authors: Cassiano Chiara , Casapullo Agostino , Tosco Alessandra , Monti Maria Chiara , Riccio Raffaele
Published: March 2019

A copper-(I)-catalyzed variation of the Huisgen 1,3-dipolar cycloaddition has been applied to lead the in living-cell mass-spectrometry based identification of protein targets of oleocanthal, a natural metabolite daily ingested by millions of people. Chemical proteomics revealed heat-shock proteins, HSP70 and HSP90, as main oleocanthal interactors in living systems. These two proteins are involved in cancer development and, thus, our findings could have important outcomes for a deep evaluation of the bio-pharmacological significance of oleocanthal.
Absolute Configuration Assignment of 3′,4′-di-O-acylkhellactones Using Vibrational Circular Dichroism Exciton Chirality
Authors: Buendía-Trujillo Abigail I. , Torrres-Valencia J. Martín , Joseph-Nathan Pedro , Burgueño-Tapia Eleuterio
Published: March 2019

The 3′R,4 ‘R absolute configuration (AC) of the angular-type pyranocoumarins (-)-3′,4′-di- O-acetylkhellactone (2), (-)-4′- O-acetyl-3′- O-angeloylkhellactone (3), (+)-3′- O-acetyl-4- O-isobutyroylkhellactone (4), and (-)-3′- O-angeloyl-4′- O-senecioylkhellactone (5), isolated from the aerial parts of Prionosciadum thapsoides, was assigned by vibrational circular dichroism exciton chirality (VCDEC), and confirmed by comparison of their VCD frequencies with those calculated using DFT at the B3LYP/DGDZVP level. This again reveals that AC assignments based on optical rotation data are not very confident. Evaluation of Flack and Hooft parameters obtained after single-crystal X-ray diffraction analysis of 3, independently confirmed this AC.
Goji Berry: Quality Assessment and Crop Adaptation of Plants Cultivated in Tuscany (Italy) by Combination of Carotenoid and DNA Analyses
Authors: Capecchi Giada , Goti Emanuele , Nicolai Elena , Bergonzi Maria Camilla , Monnanni Roberto , Bilia Anna Rita
Published: March 2019

In this study HPLC analysis for the evaluation of carotenoids and DNA barcoding are reported for three different samples of Lycium cultivated in Tuscany (Italy). These two analytical methods can represent integrative methods for quality control of goji, giving also crucial information on the plant adaptation to different environments. Hence, carotenoids represent the quality markers proposed by the monograph of the European Pharmacopoeia, while DNA barcoding can differentiate between species and populations and is useful for the detection of the homogeneity of the samples.
Activity of Vitis vinifera Tendrils Extract Against Phytopathogenic Fungi
Authors: Fraternale Daniele , Ricci Donata , Verardo Giancarlo , Gorassini Andrea , Stocchi Vilberto , Sestili Piero
Published: March 2019

The in vitro antifungal activity was determined of an ethanolic extract of Vitis vinifera L. tendrils (TVV) against ten plant pathogenic fungi, using the agar dilution method; activity was shown against all tested fungi. Fusarium species were the most sensitive with MIC values ranging from 250 to 300 ppm, while the basidiomycete fungus Rhizoctonia solani was the most resistant, with a MIC value of 500 ppm. Electrospray ionization tandem mass spectrometry (ESI-MSn) was used to obtain qualitative information on the main components of TVV. The high amount of polyphenolic compounds contained in TVV is likely to contribute significantly to its antifungal activity.
Aroma of Turmeric: Dependence on the Combination of Groups of Several Odor Constituents
Authors: Hasegawa Toshio , Nakatani Kenta , Fujihara Takashi , Yamada Hideo
Published: March 2019

Turmeric is a popular material that plays an important role in the flavor and fragrance industries. Although many compounds have been reported as components of turmeric, its aroma profile has not been clarified. Recently we have developed a new approach for evaluating the complex odors of materials based on recent research on the mechanism of odor recognition. Here we report the characteristic aroma properties of turmeric obtained through the investigation of its aroma profile. The hexane extract of turmeric had a turmeric-like odor, whereas the steam distillate of turmeric had a pungent, non-turmeric-like odor. We carried out bulb-to-bulb distillations of the extract and the steam distillate. For the hexane extract, two fractions with completely different odors were obtained. One was a high boiling point fraction (group A) with a turmeric-like odor, which consisted of ar-turmerone and β-turmerone as the main components, and the other was a low boiling point fraction (group B), which consisted of α-curcumene and β-sesquiphellandrene. In contrast, the bulb-to-bulb distillation of the steam distillate gave a fraction (group C) with a very different odor from groups A and B. Group C was composed of several kinds of alcohols that were not present in groups A and B. These results indicate that the group C fraction causes the different, pungent odor of the turmeric oil obtained by steam distillation. The variation in the aroma of turmeric depended on the combination of these three groups of odor constituents.
Composition and Chemical Variability of Ivoirian Xylopia staudtii Leaf Oil
Authors: Yapi Thierry Acafou , Boti Jean Brice , Ahibo Antoine Coffy , Sutour Sylvain , Bighelli Ange , Casanova Joseph , Tomi Félix
Published: March 2019

The chemical composition of a leaf oil sample from Ivoirian Xylopia staudtii Engler & Diels (Annonaceae) has been investigated by a combination of chromatographic [GC(RI)] and spectroscopic (GC-MS, 13C NMR) techniques. Thirty-five components that accounted for 91.8% of the whole composition have been identified. The oil composition was dominated by the furanoguaiadienes furanoguaia-1,4-diene (39.0%) and furanoguaia-1,3-diene (7.5%), and by germacrene D (17.5%). The composition of twelve other leaf oil samples demonstrated qualitative homogeneity, but quantitative variability. Indeed, the contents of the major components varied substantially: furanoguaia-1,4-diene (24.7–51.7%) and germacrene D (5.9–24.8%). The composition of X. staudtii leaf oil is close to that of X. rubescens leaf oil but varied drastically from those of the essential oils isolated from other Xylopia species. 13C NMR spectroscopy appeared as a powerful and complementary tool for analysis of sesquiterpene-rich essential oils.
Chemoinformatics Approach to Antibacterial Studies of Essential Oils
Authors: Miladinović Dragoljub L. , Ilić Budimir S. , Kocić Branislava D.
Published: March 2019

The chemical composition and antibacterial activity of Nepeta nuda (Lamiaceae) essential oil were examined, as well as the association between it and standard antibiotics: tetracycline and streptomycin. The antibacterial activities of 1,8-cineole, the main constituent of N. nuda oil, individually and in combination with standard antibiotics were also determined. The interactions of the essential oil and 1,8-cineole with antibiotics toward five selected strains were evaluated using the microdilution checkerboard assay in combination with chemoinformatics methods. Oxygenated monoterpenes were the most abundant compound class in the oil (57.8%), with 1,8-cineole (46.0%) as the major compound. The essential oil exhibited in vitro antibacterial activity against all tested bacterial strains, but the activities were lower than those of the standard antibiotics. The combinations N. nuda oil-antibiotic and 1,8-cineole-antibiotic produced a predominantly antagonistic interactions. Chemoinformatics survey confirms the antagonistic interactions as a consequence of membrane potential/proton motive force dissipation. These data indicate cytochrome c oxidase as a target for 1.8-cineole toxicity action mechanisms.
Chemical Composition of Nardostachys grandiflora Rhizome Oil from Nepal – A Contribution to the Chemotaxonomy and Bioactivity of Nardostachys
Authors: Satyal Prabodh , Chhetri Bhuwan K. , Dosoky Noura S. , Poudel Ambika , Setzer William N.
Published: March 2019

The essential oil from the dried rhizome of Nardostachys grandiflora, collected from Jaljale, Nepal, was obtained in 1.4% yield, and a total of 72 compounds were identified constituting 93.8% of the essential oil. The rhizome essential oil of N. grandiflora was mostly composed of calarene (9.4%), valerena-4,7(11)-diene (7.1%), nardol A (6.0%), 1(10)-aristolen-9-ol (11.6%), jatamansone (7.9%), valeranal (5.6%), and cis-valerinic acid (5.7%). The chemical composition of N. grandiflora rhizome oil from Nepal is qualitatively very different than those from Indian, Chinese, and Pakistani Nardostachys essential oils. In this study we have evaluated the chemical composition and biological activities of N. grandiflora from Nepal. Additionally, 1(10)-aristolen-9-ol was isolated and the structure determined by NMR, and represents the first report of this compound from N. grandiflora. N. grandiflora rhizome oil showed in-vitro antimicrobial activity against Bacillus cereus, Escherichia coli, and Candida albicans (MIC = 156 μg/mL), as well as in-vitro cytotoxic activity on MCF-7 cells.
Chemical Composition and Biological Activity of Essential Oils from Wild Growing Aromatic Plant Species of Skimmia laureola and Juniperus macropoda from Western Himalaya
Authors: Stappen Iris , Tabanca Nurhayat , Ali Abbas , Wedge David E. , Wanner Jürgen , Kaul Vijay K. , Lal Brij , Jaitak Vikas , Gochev Velizar K. , Schmidt Erich , Jirovetz Leopold
Published: March 2019

The Himalayan region is very rich in a great variety of medicinal plants. In this investigation the essential oils of two selected species are described for their antimicrobial and larvicidal as well as biting deterrent activities. Additionally, the odors are characterized. Analyzed by simultaneous GC-MS and GC-FID, the essential oils’ chemical compositions are given. The main components of Skimmia laureola oil were linalool and linalyl acetate whereas sabinene was found as the main compound for Juniperus macropoda essential oil. Antibacterial testing by agar dilution assay revealed highest activity of S. laureola oil against all tested bacteria, followed by J. macropoda oil. Antifungal activity was evaluated against the strawberry anthracnose causing plant pathogens Colletotrichum acutatum, C. fragariae and C. gloeosporioides. Juniperus macropoda essential oil indicated higher antifungal activity against all three pathogens than S. laureola oil. Both essential oils showed biting deterrent activity above solvent control but low larvicidal activity.
Chemical Components of Four Essential Oils in Aromatherapy Recipe
Authors: Tadtong Sarin , Kamkaen Narisa , Watthanachaiyingcharoen Rith , Ruangrungsi Nijsiri
Published: March 2019

This study focused on characterization of the chemical components of an aromatherapy recipe. The formulation consisted of four blended essential oils; rosemary oil, eucalyptus oil, pine oil and lime oil (volume ratio 6: 2: 1: 1). The single and combination essential oils were identified by gas chromatography-mass spectrometry (GC-MS). The analysis of GC-MS data revealed that several components exist in the mixture. The five most important components of the blended essential oils were 1,8-cineole (35.6 %), α-pinene (11.1 %), limonene (9.6 %), camphor (8.4 %), and camphene (6.6 %). The main components of rosemary oil were 1,8-cineole (37.3 %), α-pinene (19.3 %), camphor (14.7 %), camphene (8.8 %), and β-pinene (5.5 %); of eucalyptus oil 1,8-cineole (82.6 %) followed by limonene (7.4 %), o-cymene (4.3 %), γ-terpinene (2.7 %), and α-pinene (1.5 %); of pine oil terpinolene (26.7 %), α-terpineol (20.50 %), 1-terpineol (10.8 %), α-pinene (6.0 %), and γ-terpineol (5.3 %); and of lime oil limonene (62.9 %), γ-terpinene (11.5 %), α-terpineol (7.6 %), terpinolene (6.0 %), and α-terpinene (2.8 %). The present study provided a theoretical basis for the potential application of blended essential oils to be used as an aromatherapy essential oil recipe. GC-MS serves as a suitable and reliable method for the quality control of the chemical markers.
Recent Advances in the Synthesis of Stemona Alkaloids
Authors: Liu Xiao-Yu , Wang Feng-Peng
Published: March 2019

Stemona alkaloids, featuring polycyclic structures and interesting bioactivities, constitute a distinct class from the Stemonaceae family. In this review, recent advances in the synthesis of these unique alkaloids are briefly discussed, highlighting the application of novel synthetic strategies to access the core structures, as well as creative solutions to the installation of multiple stereogenic centers. The literature reviewed in this article covers the publications from 2010 to November 2014, a period that witnessed the prosperity of the synthesis of Stemona alkaloids.
Phytochemistry and Pharmacology of the Genus Tovomita
Authors: Epifano Francesco , Specchiulli Maria Carmela , Taddeo Vito Alessandro , Fiorito Serena , Genovese Salvatore
Published: March 2019

The genus Tovomita (Fam. Clusiaceae) comprises 45 species mainly found in tropical regions of Central and South America. Most of the species of the title genus have been used for centuries as natural remedies. Phytochemicals isolated from Tovomita spp. include prenylated and unprenylated benzophenones and xanthones. The aim of this review is to examine in detail from a phytochemical and pharmacological point of view what is reported in the past and current literature about the properties of phytopreparations and individual active principles obtained from plants belonging to the Tovomita genus.
Fungal Phytotoxins with Potential Herbicidal Activity to Control Chenopodium album
Authors: Cimmino Alessio , Masi Marco , Evidente Marco , Evidente Antonio
Published: March 2019

This review deals with the isolation and chemical and biological characterization of phytotoxins produced by Ascochyta caulina and Phoma chenopodiicola proposed as mycoherbicides for the biological control of Chenopodium album, a worldwide spread weed which causes serious problems to some agrarian crops, including sugar beet and maize. Studies on the structure activity relationships and on the modes of actions of toxins isolated are also described, as well as the optimization of analytical methods focused on selection of the best fungal toxin producers. The attempts to scale up production of these phytotoxins aimed to obtain sufficient amounts for their application in greenhouse and field trials are also reported.