bluuebunny/crossref_metadata_2025 huggingface dataset:
Determination of Antioxidant Properties of 26 Chilean Honeys and a Mathematical Association Study with their Volatile Profile
Authors: Sánchez Elizabeth , Piovano Marisa , Valdés Erika , Young Manuel E. , Acevedo Cristian A. , Osorio Mauricio
Published: March 2019

Radical scavenging activity (RSA), antioxidant content (TEAC), total phenolic compounds content (TPCC) and volatile profile (VOCs) were measured in 26 honeys obtained from the Valparaíso Region (Chile). Persea americana honey was the most interesting sample according to these evaluated parameters. A Projection to Latent Structures (PLS) based algorithm was used to model the possible relationship between antioxidant activity, total phenolic compounds content and volatile profile. Concerning the volatile profile, only nine volatile compounds, of a total of fifty, showed dependence on antioxidant activity and total phenolic compounds content.
Chemical Constituents and Antioxidant and Biological Activities of the Essential Oil from Leaves of Solanum spirale
Authors: Keawsa-ard Sukanya , Liawruangrath Boonsom , Liawruangrath Saisunee , Teerawutgulrag Aphiwat , Pyne Stephen G.
Published: March 2019

The essential oil of the leaves Solanum spirale Roxb. was isolated by hydrodistillation and analyzed for the first time using GC and GC-MS. Thirty-nine constituents were identified, constituting 73.36% of the total chromatographical oil components. ( E)-Phytol (48.10%), n-hexadecanoic acid (7.34%), β-selinene (3.67%), α-selinene (2.74%), octadecanoic acid (2.12%) and hexahydrofarnesyl acetone (2.00%) were the major components of this oil. The antioxidant activity of the essential oil was evaluated by using the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging assay. The oil exhibited week antioxidant activity with an IC50 of 41.89 mg/mL. The essential oil showed significant antibacterial activity against both Gram-negative Escherichia coli and Gram-positive Staphylococcus aureus with MIC values of 43.0 μg/mL and 21.5 μg/mL, respectively. It also showed significant cytotoxicity against KB (oral cancer), MCF-7 (breast cancer) and NCI-H187 (small cell lung cancer) with the IC50 values of 26.42, 19.69, and 24.02 μg/mL, respectively.
Acetylcholinesterase Inhibition within the Lycorine Series of Amaryllidaceae Alkaloids
Authors: Nair Jerald J. , van Staden Johannes
Published: March 2019

The plant family Amaryllidaceae occupies a privileged status within the botanical hierarchy due to its horticultural and ornamental appeal, as well as its widespread usage in the traditional medicinal practices of indigenous peoples across the globe. Of greater significance are the unique, structurally-diverse alkaloid constituents produced by members of the family, which has spawned several biologically significant molecules. In this regard, the Alzheimer's drug galanthamine has gained much prominence due to its selective and reversible inhibitory interaction with the enzyme acetylcholinesterase (AChE), of significance in the progression of neurodegeneration associated with Alzheimer's disease (AD). The lycorine series of compounds within the family have recently emerged as novel inhibitors of AChE, in some instances with higher levels of activity compared with the commercial drug galanthamine, making them attractive targets for natural product and synthetically-driven structure-activity relationship studies. This brief survey traces the emergence of lycorine compounds over the past decade as promising leads in the therapeutic approach towards AD and their possible future advancement onto the clinical stage.
Alkaloids Produced by Endophytic Fungi: A Review
Authors: Zhang Yanyan , Han Ting , Ming Qianliang , Wu Lingshang , Rahman Khalid , Qin Luping
Published: March 2019

In recent years, a number of alkaloids have been discovered from endophytic fungi in plants, which exhibited excellent biological properties such as antimicrobial, insecticidal, cytotoxic, and anticancer activities. This review mainly deals with the research progress on endophytic fungi for producing bioactive alkaloids such as quinoline and isoquinoline, amines and amides, indole derivatives, pyridines, and quinazolines. The biological activities and action mechanisms of these alkaloids from endophytic fungi are also introduced. Furthermore, the relationships between alkaloid-producing endophytes and their host plants, as well as their potential applications in the future are discussed.
Betulin as an Antitumor Agent Tested in vitro on A431, HeLa and MCF7, and as an Angiogenic Inhibitor in vivo in the CAM Assay
Authors: Dehelean Cristina Adriana , Feflea Stefana , Molnár Judit , Zupko Istvan , Soica Codruta
Published: March 2019

Betulin, an important compound found in birch tree bark, can be converted to betulinic acid, an important pharmacological substance. Betulin has recently been reported as a cytotoxic agent for several tumor cell lines and as an apoptotic inductor. Angiogenesis is a key process involved in tumor metastasis and in developing tumor resistance to cytotoxic therapy. There are little data on betulin as an anti angiogenic agent. This preliminary study aimed to evaluate the cytotoxic effect of betulin on three cancer cell lines: HeLa (cervix adenocarcinoma), MCF7 (breast adenocarcinoma) and A431 (skin epidermoid carcinoma), and the apoptotic mechanism, as well as the implication in the capillary formation of the chicken embryo chorioallantoic membrane. The analysis consisted in the interpretation of the MTT assay and fluorescence double staining with Hoechst dye 33258 and propidium iodide, while the angiogenic effect was evaluated using morphological and immunohistochemical techniques. The antitumor activity is revealed by the double fluorescence staining, indicating that at higher concentrations, the cell membrane permeability is enhanced, while at lower concentrations there is evidence for nuclear fragmentation. In what concerns its effect on the process of blood vessel formation, betulin induced the reduction of newly formed capillaries, especially in the mesenchyme, possible through targeting the normal function of endothelial cells. In vitro results proved the superior specificity of betulin on cervical cancer cells, followed by skin cancer cells.
Chromolithic Method Development, Validation and System Suitability Analysis of Ultra-Sound Assisted Extraction of Glycyrrhizic Acid and Glycyrrhetinic Acid from Glycyrrhiza glabra
Authors: Gupta Suphla , Sharma Rajni , Pandotra Pankaj , Jaglan Sundeep , Gupta Ajai Prakash
Published: March 2019

An ultrasound-assisted extraction and chromolithic LC method was developed for simultaneous determination of glycyrrhizic acid (GA) and glycyrrhetinic acid (GL) from the root extract of Glycyrrhiza glabra using RPLC-PDA. The developed method was validated according to the International Conference on Harmonisation. The method exhibited good linearity (r2 >0.9989) with high precision and achieved good accuracies between 97.5 to 101.3% of quantitative results. The method is more sensitive and faster (resolved within ten minutes) than the earlier developed methods using normal LC columns.
Flavonoids from the Japanese Monotypic Genus, Nipponanthemum
Authors: Uehara Ayumi , Iwashina Tsukasa
Published: March 2019

Foliar flavonoids of Nipponanthemum, which is a monotypic genus and consists of only one Japanese endemic species, N. nipponicum, were isolated for the first time. Fifteen flavonoids, i.e. six glycosides, quercetin 3,7-di- O-glucoside, vicenin-2, quercetin 3- O-glucoside, luteolin 7- O-glucoside, kaempferol 3- O-glucoside and apigenin 7- O-glucoside, and nine aglycones, luteolin, nepetin, quercetin 3-methyl ether, axillarin, apigenin, hispidulin, chrysoeriol, jaceosidin and sudachitin were identified. Of these compounds, the flavonoid aglycones existed on the leaf surface.
Two New Alkylresorcinols from Homalomena wendlandii and Their Cytotoxic Activity
Authors: Sánchez Luis A. , Olmedo Dionisio , López-Pérez José Luis , Williams Todd D. , Gupta Mahabir P.
Published: March 2019

In the course of our search for antineoplasic agents from Panamanian Flora, two new alkylresorcinols: 1-(2,6-dihydroxyphenyl)octan-1-one (1) and (+)-1-(3-(1-(2,6-dihydroxyphenyl)butyl)-2,6-dihydroxyphenyl)octan-1-one (2), together with three known compounds, (1 R, 2 R)-1-(benzo[ d][1,3]dioxol-5-yl)propane-1,2,3-triol (3), (+)-aptosimon (4) and (-)-sesamin (5), were identified from the leaves of Homalomena wendlandii Schott (Araceae). Their structures were established by 1D and 2D NMR and IR spectroscopic, and MS methods. Compound 2 exhibited IC50 values of 3.3, 5.8 and 4.0 μg/mL against MCF-7, SF-268 and H-460 cancer human cell lines, respectively.
Amides and an Alkaloid from Portulaca oleracea
Authors: Kokubun Tetsuo , Kite Geoffrey C. , Veitch Nigel C. , Simmonds Monique S. J.
Published: March 2019

A total of 16 phenolic compounds, including one new and five known N-cinnamoyl phenylethylamides, one new pyrrole alkaloid named portulacaldehyde, five phenylpropanoid acids and amides, and derivatives of benzaldehyde and benzoic acid, were isolated and identified from a polar fraction of an extract of Portulaca oleracea. Their structures were determined through spectroscopic analyses.
Two New p-Terphenyl Derivatives from the Marine Fungal Strain Aspergillus sp. AF119
Authors: Liu Shao-Song , Zhao Bao-Bing , Lu Chun-Hua , Huang Jing-Jing , Shen Yue-Mao
Published: March 2019

Two new p-terphenyl derivatives (1, 2), together with six known ones (3 - 8), have been isolated from the marine fungal strain Aspergillus sp. AF119. The structures for terphyl acid (1) and terphyl diacid (2) were determined on the basis of HR Q-TOF-MS, and 1D- and 2D-NMR spectroscopic data. The in vitro cytotoxic activities of compounds 1 – 8 were tested against human tumor cell lines HeLa, HepG-2 and MDA-MB-435; only compounds 5 – 8 exhibited inhibitory activity against the tested cell lines with IC50 values < 20 μM. Moreover, compound 5 showed a mechanism of inducing cell cycle arrest and apoptosis mediated by the generation of ROS and subsequent DNA double-strand break.
Cytokinin and Auxin Effect on the Terpenoid Profile of the Essential Oil and Morphological Characteristics of Shoot Cultures of Artemisia alba
Authors: Danova Kalina , Todorova Milka , Trendafilova Antoaneta , Evstatieva Ljuba
Published: March 2019

The influence of plant growth regulators (PGR) on the essential oil composition and in vitro development of A. alba shoot cultures was studied. Two types of oils were determined, based on their terpenoid content. Close relations between the morphogenetic effects of PGR and the essential oil profile of the species were observed. Predominance of root over shoot development was connected with a drop in the amounts of sesquiterpenoids and the direction of biosynthesis towards oxygenated monoterpenoids in the PGR-free control medium, as well in those with 1.0 mg L−1 indole-3-butyric acid (IBA) supplementation. On the contrary, lack of root formation and stimulated callusogenesis caused by the addition of 0.2 mg L−1 6-benzyladenine (BA), irrespectively of the presence of IBA (either 0.5 mg L−1 or 1.0 mg L−1), resulted in the strong prevalence of sesquiterpenoids in the oils. These results are indicative that the morphological development of A. alba shoot cultures affects the terpenoid biosynthetic pathway bringing out the hypothesis for a possible root to shoot signaling.
Chemical Composition and Antimicrobial Activity of Essential Oil of Different Parts of Seseli rigidum
Authors: Marčetić Mirjana , Božić Dragana , Milenković Marina , Lakušić Branislava , Kovačević Nada
Published: March 2019

The chemical composition and antimicrobial activity of the essential oil of the Balkan endemic species Seseli rigidum Waldst. & Kit. (Apiaceae) was investigated. The monoterpene α-pinene was predominant in the volatile oil from aerial parts (57.4%) and fruit (23.3%). In the essential oil of the aerial parts limonene (6.7%), camphene (5.8%) and sabinene (5.5%) were also present in high amounts, and in the fruit oil, β-phellandrene (17.4%) and sabinene (12.9%). On the contrary, the root essential oil was composed almost entirely of the polyacetylene falcarinol (88.8%). The antimicrobial activity of the root essential oil was significant against Staphylococcus aureus, S. epidermidis, Micrococcus luteus and Enterococcus faecalis (MICs 6.25–25.00 μg/mL). Volatile constituents from the root strongly inhibited the growth of methicillin-resistant strains of S. aureus (MICs 6.25–50.00 μg/mL). Anti-staphylococcal activity can be attributed to the main volatile constituent of S. rigidum root, falcarinol.
Electrophysiological Responses of the Naupactus bipes Beetle to Essential Oils from Piperaceae Species
Authors: Ramos Clécio S. , Soares Marisi G. , da Silva Adalberto M. , Batista-Pereira Luciane G. , Corrêa Arlene G. , Kato Massuo J.
Published: March 2019

Electrophysiological responses based on electroantennographic detection (GC-EAD) and electroantennography (EAG) analysis of Naupactus bipes beetles (Germar, 1824) (Coleoptera: Curculionidae: Brachycerinae) were used to test volatile oils of Piper gaudichaudianum, P. regnellii and P. hispidum. In the EAG experiments, female and male beetles showed significant EAG response to the three volatile oils of Piper species, with the females’ responses slightly higher than the males’. The experiments with GC-EAD revealed that some terpenoids (namely, α-pinene, β-pinene, myrcene, α-copaene and germacrene) present in the leaf essential oils of the Piper species are perceptible to female and male beetles.
Inhibition of Essential Bacterial Peptidyl-tRNA Hydrolase Activity by Tropical Plant Extracts
Authors: McFeeters Hana , Gilbert Morgan J. , Thompson Rachel M. , Setzer William N. , Cruz-Vera Luis R. , McFeeters Robert L.
Published: March 2019

Peptidyl-tRNA Hydrolase (Pth) is a highly conserved, essential enzyme in bacteria. It removes the peptide portion from peptidyl-tRNA, returning free tRNAs to participate in translation. Build-up of peptidyl-tRNAs is toxic and defects in Pth function result in cell death. Herein we use in vitro activity of recombinant E. coli Pth to screen tropical plant extracts for inhibition. Multiple extracts were found to have inhibitory activity with some exhibiting different inhibitory effects depending on extraction conditions. IC50 values ranged from 0.02 to > 53.8 μg of extract per 1 unit of Pth, holding promise for in vivo screening. The inhibitory components in these extracts may serve as lead compounds for development of novel antibacterials.
Naturally Occurring Limonene to Cinnamyl-type γ-Butyrolactone Substituted Aldol Condensation Derivatives as Antioxidant Compounds
Authors: Kaur Pushpinder , Das Pralay , Chaudhary Abha , Singh Bikram
Published: March 2019

A method has been developed for the synthesis of γ-butyrolactone substituted cinnamyl type Aldol condensation products under milder proline and triethylamine basic conditions. The antioxidant activity of all the synthesized compounds was assessed using three different assays. The cinnamyl type derivatives of γ-butyrolactone bearing an -OH group in the benzene ring exhibited excellent antioxidant activity.
Chemical Fingerprinting by RP-RRLC-DAD and Principal Component Analysis of Ziziphora clinopodioides from Different Locations
Authors: Tian Shuge , Yu Qian , Xin Lude , Zhou Zhaohui Sunny , Upur Halmuart·
Published: March 2019

An efficient and accurate fingerprinting method using reversed-phase rapid-resolution liquid-chromatography coupled with photodiode array detection has been developed and optimized to examine the variance in active compounds among Ziziphora clinopodioides Lam from different locations. Three active components, diosmin, linarin and pulegone, were identified by matching their retention times and UV spectra with the corresponding reference compounds. Our results indicated that chromatographic fingerprints, in combination with principal component analysis (PCA) and hierarchical clustering analysis (HCA), could efficiently identify and distinguish Z. clinopodioides from different sources. Our fingerprinting methods and data will be useful for quality control, and thus, more effective dosing in clinical application of Z. clinopodioides.
Biological Activity of Isoflavonoids from Azorella madreporica
Authors: Quesada Luisa , Areche Carlos , Astudillo Luis , Gutiérrez Margarita , Sepúlveda Beatriz , San-Martín Aurelio
Published: March 2019

Four isoflavones, isolated from the whole plant of Azorella madreporica, were identified as angustone C (1), alpinumisoflavone (2), licoisoflavone A (3) and isolupalbigenin (4) by spectroscopic studies. The compounds were evaluated for antibacterial and gastroprotective activities. This is the first time that isoflavonoids have been reported in this genus.
Analysis of Homoisoflavonoids in Caesalpinia digyna by HPLC-ESI-MS, HPLC and Method Validation
Authors: Roy Somendu K. , Srivastava Amit , Jachak Sanjay M.
Published: March 2019

The roots of Caesalpinia digyna have been reported to contain gallic acid derivatives and minor homoisoflavonoids, but HPLC-ESI-MS and HPLC analyses of the homoisoflavonoids were challenging due to their low concentration in the roots. Separation and identification was accomplished by HPLC-ESI-MS and further elaborated for quantification using a C18 column with detection at 330 nm. A gradient mobile phase consisting of methanol and water (0.1% acetic acid) was used. The developed HPLC method showed good linearity (r2≥0.998), high precision (RSD<5%) and a good recovery (99.3-104.5%) of the compounds. The lowest detection limit was 0.75 ng and the method was found to be robust. All the validation parameters were found to be within the permissible limits and, therefore, the developed method is accurate and reliable for the quality control of C. digyna and other Caesalpinia species. This is the first report of sample preparation on Diaion HP-20 resin and characterization of homoisoflavonoids by HPLC-ESI-MS, extended by extensive quantitative HPLC analysis of homoisoflavonoids in C. digyna roots and method validation.
Furanone Derivatives from Terrestrial Streptomyces spp
Authors: Arfan Muhammad , Shaaban Khaled A. , Schüffler Anja , Laatsch Hartmut
Published: March 2019

Chemical investigation of the terrestrial Streptomyces sp. isolates GT2005/020 and ANK148 led to the isolation of two microbial furanone derivatives, 5-hydroxy-4-methylnaphtho[1,2-b]furan-3-one (1) and 4-hydroxy-5-methyl-furan-3-one (2), respectively, which have some similarity to quorum sensing molecules of the AI-2 type. In addition, the known compounds chalcomycin, ferulic acid, indole-3-acetic acid, uracil, thymine, 2′-deoxy-thymidin, monensin B (3), phencomycin, and 1-acetyl-β-carboline were isolated. The structures of 1 and 2 were deduced from extensive studies of NMR (1D and 2D) and mass spectra. Additionally, the complete NMR shift assignments for monensin B (3) using H-H COSY, HMQC and HMBC experiments are reported here for the first time. We are describing the taxonomy and fermentation of the producing strains, the structure elucidation of the new metabolites and their bioactivity.
Cytotoxicity Analysis of Active Components in Bitter Melon (Momordica charantia) Seed Extracts Using Human Embryonic Kidney and Colon Tumor Cells
Authors: Chipps Elizabeth S. , Jayini Renuka , Ando Shoko , Protzman April D. , Muhi M. Zubayed , Mottaleb M. Abdul , Malkawi Ahmed , Islam M. Rafiq
Published: March 2019

Bitter melon (Momordica charantia) seed extracts (BMSE) have been used as traditional medicine for treating various ailments, although in many cases, the active component(s) are unidentified. In this study, bitter melon seeds were extracted in water, ethanol, or ethanol: water (1:1). The aqueous seed extracts (BMSE-W) exhibited marked cytotoxicity towards human embryonic kidney 293T (HEK293T) and human colon tumor 116 (HCT116) cells. The activity in BMSE-W was unaffected by heat and proteinases treatments, and eluted in the total volume of size-exclusion HPLC, suggesting the small, organic nature of the active component(s). Gas chromatographic-mass spectrometic (GC-MS) analysis of the HPLC fractions identified methoxy-phenyl oxime (MPO) as a major active component. Acetophenone oxime, a commercially available structural homolog of MPO, demonstrated cytotoxicity comparable with that of the BMSE-W. The oxime functional group was found to be critical for activity. Increased poly-(ADP-ribose)-polymerase and β-actin cleavage, and chromatin condensation observed in treated cells suggested apoptosis as a plausible cause for the cytotoxicity. This study, for the first time, identified a cytotoxic oxime in BMSE-W.
Insecticidal Properties of Annonaceous Acetogenins and Their Analogues. Interaction with Lipid Membranes
Authors: Blessing Lilian Di Toto , Ramos Juan , Diaz Sonia , Altabef Aída Ben , Bardón Alicia , Brovetto Margarita , Seoane Gustavo , Neske Adriana
Published: March 2019

The interactions were studied by FTIR and DSC of the terminal lactone of annonaceous acetogenins (ACGs) and synthetic analogues, such as THF, with POPC bilayers, as well as the toxic effect produced by these compounds on Spodoptera frugiperda larvae. The aim of this work was to find a relationship between ACG insecticidal properties and the specific sites of interaction with lipid membranes. ACGs interact to different extents with the phosphate of lipid membranes and differences in the antisymmetric stretching of the phosphate groups were found in the presence of water that indicate water loss and further hydrogen bonding. The ACG tested produced more than 70% larval mortality. Rolliniastatin-1 (3) proved to have the most toxic effects (100%) on early larval instars when incorporated in the larval diet at a dose of 100 μg per g of diet. Additionally, it produced a significant decrease in growth rate (GR) and consumption index (CI), and reduced the efficiency with which larvae converted ingested food into biomass (ECI). The destabilization that occurs in the membrane due to dehydration around the phosphate groups caused by interaction with ACGs and their synthetic analogues would account for ACGs’ insecticidal action.
Optimization of Carbon Source for Hairy Root Growth and Withaferin A and Withanone Production in Withania somnifera
Authors: Sivanandhan Ganeshan , Rajesh Manoharan , Arun Muthukrishnan , Jeyaraj Murugaraj , Dev Gnanajothi Kapil , Manickavasagam Markandan , Selvaraj Natesan , Ganapathi Andy
Published: March 2019

This study optimized carbon sources in half MS liquid medium for maximum biomass accumulation and withanolides production in hairy root culture of Withania somnifera. The highest production of withaferin A and withanone was achieved when sucrose and sucrose+glucose were used individually as carbon sources. The hairy root suspension culture supplemented with a lower level of sucrose (2%) favored hairy root biomass accumulation (1.41 g DW) followed by sucrose+glucose (2+1) when compared with other carbon sources in half MS liquid medium after 40 days of culture. The hairy roots grown on sucrose (4%) enriched half MS liquid medium stimulated higher production of withaferin A (2.21 mg/g DW) and withanone (2.41 mg/g DW) on the 40th day of culture, followed by sucrose+glucose (4+1%) compared with glucose, fructose, maltose and other combinations tested.
Identification of Pavinane Alkaloids in the Genera Argemone and Eschscholzia by GC-MS
Authors: Cahlíková Lucie , Kučera Radim , Hošt’álková Anna , Klimeš Jiří , Opletal Lubomír
Published: March 2019

The genera Eschscholtzia and Argemone(Papaveraceae) represent a rich source of pavinane alkaloids, the identification of which in alkaloid extracts is generally problematic without standards. The alkaloid extracts of three Argemone and four Eschscholtzia species were analyzed using GC-MS. The alkaloids were identified based on comparison of their mass spectra with commercial libraries, with reported data in the literature and with spectra of reference compounds. A total of 23 alkaloids of six structural types (pavinane, protopine, benzylisoquinoline, benzophenanthridine, aporphine and protoberberine) were identified. The fragmentation pathway of pavinane alkaloids was used for their identification. O-Methylneocaryachine has been reported for the first time from a natural sources and the alkaloid pattern of Eschscholzia pulchella has been analyzed and described for the first time.
Profiling Flavonoid Cytotoxicity in Human Breast Cancer Cell Lines: Determination of Structure-Function Relationships
Authors: Yadegarynia Sina , Pham Anh , Ng Alex , Nguyen Duong , Lialiutska Tetiana , Bortolazzo Anthony , Sivryuk Valentin , Bremer Martina , White J. Brandon
Published: March 2019

Flavonoids have been shown to be cytotoxic to cancer cells. However, the mechanism of cytotoxicity has not been clearly defined. It has previously been reported that HER2/ERBB2, the estrogen receptor, progesterone receptor, and p53 were required for flavonoid induced cytotoxicity in breast cancer cell lines. We have used a panel of breast cancer cell lines, known to contain as well as be deficient in these signaling pathways, to screen fourteen different flavonoids. Comparing the cytotoxicity for all flavonoids allows us to determine if a structure-functional relationship exists between cytotoxicity and flavonoid, and if a particular signaling pathway is required for cytotoxicity. We show that several flavonoids are cytotoxic to all cell lines including primary mammary epithelial cells tested. The cytotoxic flavonoids are also able to inhibit Mitochondrial Outer Membrane Permeability while at the same time stimulate ATP levels whereas the non-cytotoxic flavonoids are not able to do this. We also show that both cytotoxic and non-cytotoxic flavonoids can transverse the cell membrane to enter MDA-MB-231 cells at different levels. Finally, all flavonoids regardless of their cytotoxicity were able to induce some form of cell cycle arrest. We conclude that for flavonoids to be strongly cytotoxic, they must possess the 2,3-double bond in the C-ring and we believe the cytotoxicity occurs through mitochondrial poisoning in both cancer and normal cells.
Effect of Seasonality on Chemical Composition and Antibacterial and Anticandida Activities of Argentine Propolis. Design of a Topical Formulation
Authors: Isla María Inés , Dantur Yanina , Salas Ana , Danert Carolina , Zampini Catiana , Arias Myriam , Ordóñez Roxana , Maldonado Luis , Bedascarrasbure Enrique , Moreno María Inés Nieva
Published: March 2019

The effect of seasonality on Argentine propolis collected during one year on its phenolic and flavonoid content and on the growth of Gram-positive and Gram-negative antibiotic resistant bacteria and Candida species was evaluated. Extracts of propolis samples collected in the summer and spring showed higher phenolic and flavonoid contents than the samples collected in other seasons (5.86 to 6.06 mg GAE/mL and 3.77 to 4.23 mg QE/mL, respectively). The propolis collected in summer and autumn showed higher antibacterial activity (30 μg/mL) than the other samples (MIC values between 30 and 120 μg/mL). No antibacterial activity was detected against Gram-negative bacteria. Also, these extracts were able to inhibit the development of five Candida species, with MFC values of 15-120 μg/mL. Pharmaceutical formulations containing the more active propolis extract were prepared. The hydrogel of acrylic acid polymer containing summer propolis extract as an antimicrobial agent showed microbiological, physical and functional stability during storage for 180 days. The pharmaceutical preparation, as well as the propolis extracts, was active against Candida sp. and antibiotic-multi-resistant Gram-positive bacteria. These results reveal that propolis samples collected by scraping in four seasons, especially in summer in Calingasta, San Juan, Argentina, can be used to obtain tinctures and hydrogels with antibacterial and antimycotic potential for topical use.
Phenolic Compounds in Five Epilobium Species Collected from Estonia
Authors: Remmel Indrek , Vares Lauri , Toom Lauri , Matto Vallo , Raal Ain
Published: March 2019

Epilobium species have been traditionally used as medicinal plants to treat benign prostate hyperplasia. The present study investigated the content of polyphenols, tannins, and flavonoids in Epilobium parviflorum Schreb., E. hirsutum L., E. adenocaulon Hausskn., E. montanum L., and E. palustre L. growing in Estonia. The total contents of polyphenols, tannins, and flavonoids were studied using UV spectroscopy with subsequent HPLC quantification of gallic acid, ellagic acid, and quercetin as marker compounds. All roots, stems, leaves, and flowers of the plants investigated contained comparable amounts of polyphenols, tannins, and flavonoids. There was a clear positive correlation between the contents of tannins and flavonoids in various plant parts. The content of these biologically active compounds suggests the use of E. parviflorum, E. hirsutum, E. adenocaulon, E. montanum, and E. palustre collected from Estonia as herbs both individually or as a blend.
Two New Naphthoquinone Derivatives from the Stem Bark of Callicarpa Maingayi
Authors: Asiri Sumayah Mohammed , Shaari Khozirah , Abas Faridah , Al-Mekhlafi Nabil Ali , Lajis Nordin H.
Published: March 2019

Two new naphthoquinones designated as 3α-hydroxy-2-(2-hydroxypropan-2-yl)-9α-methoxy-2,3,3α,9α-tetra-hydronaphtho[2,3-b]furan-4,9-dione (callicarpa-quinone A, 1) and 5-hydroxy-2-(2-hydroxypropan-2-yl)naphtho[2,3-b]furan-4,9-dione (callicarpaquinone B, 2) were isolated from the chloroform fraction of Callicarpa maingayi. Three other known compounds, identified as avicequinone-C (3), wodeshiol (4) and paulownin (5), were reported for the first time from this species. The structure elucidation of compounds was established by comprehensive 1D and 2D NMR spectroscopic analyses as well as EIMS, UV and IR spectral data. Compounds 1 and 2 were tested in vitro for their cytotoxic activity against human breast cancer MCF-7cells. Compound 2 exhibited strong cytotoxic activity with an IC50 value of 1.9 ± 0.2 μM, while 1 showed moderate activity with an IC50 value of 25.0 ± 4.3 μM.
Chemotaxonomical Markers in Essential Oil of Murraya Koenigii
Authors: Nagappan Thilahgavani , Ramasamy Perumal , Vairappan Charles Santhanaraju
Published: March 2019

The composition of the essential oils of Murraya koenigii(L.) Spreng, cultivated at six locations in Peninsula Malaysia and Borneo are presented. The oils were obtained from fresh leaves by hydrodistillation and analyzed by gas chromatography-mass spectrometry (GC-MS); 61 compounds were identified, of which eleven were present in all the specimens analyzed. The two major volatile metabolites were identified as β-caryophyllene (16.6-26.6%) and α-humulene (15.2-26.7%) along with nine minor compounds identified as β-elemene (0.3-1.3%), aromadendrene (0.5-1.5%), β-selinene (3.8-6.5%), spathulenol (0.6-2.7%), caryophyllene oxide (0.7-3.6%), viridiflorol (1.5-5.5%), 2-naphthalenemethanol (0.7-4.8%), trivertal (0.1-1.0%) and juniper camphor (2.6-8.3%). The results suggest that β-caryophyllene and α-humulene could be used as chemotaxonomical markers for Malaysian M. koenigii, hence these specimens could be of the same stock and different from the ones in India, Thailand and China.
Antiproliferative Oleanane Saponins from Dizygotheca Elegantissima
Authors: Vassallo Antonio , Pesca Mariasabina , Ambrosio Letizia , Malafronte Nicola , Melle Nadia Dekdouk , Dal Piaz Fabrizio , Severino Lorella
Published: March 2019

Four new oleanane saponins (1-4), together with three known saponins, were isolated from the aerial parts of Dizygotheca elegantissima R. Vig. & Guillaumin. Their structures were elucidated by 1D and 2D NMR experiments including 1D TOCSY, DQF-COSY, HSQC, and HMBC spectroscopy, as well as ESIMS analysis. The antiproliferative activity of all isolated compounds was evaluated.
Classification Using NMR-based Metabolomics of Sophora Flavescens Grown in Japan and China
Authors: Suzuki Ryuichiro , Ikeda Yuriko , Yamamoto Akari , Saima Toyoe , Fujita Tatsuya , Fukuda Tatsuo , Fukuda Eriko , Baba Masaki , Okada Yoshihito , Shirataki Yoshiaki
Published: March 2019

We demonstrate that NMR-based metabolomics can be used to identify the country of growth (Japan or China) of Sophora flavescens plants. Principle Component Analysis (PCA) conducted on extracts of S. flavescens grown in China provided data distinct from that of extracts of plants grown in Japan. Loading plot analysis showed signals characteristic of Japanese S. flavescens. NMR analyses showed these signals to be due to kurarinol (1) and kushenol H (2). These compounds were confirmed by HPLC analysis to be distinctive markers for Japanese S. flavescens.
Effects of Anhydroicaritin and 2″-Hydroxy-3″-en-Anhydroicaritin on the Proliferation and Differentiation of MC3T3–E1 Osteoblasts
Authors: Li Yanping , Zhang Xuehui , Peng Hui , Li Rongtao , Deng Xuliang
Published: March 2019

Epimedium brevicornu Maxim., one of the most frequently used traditional Chinese medicines for thousands of years, is prescribed as having “bone strengthening” function and the ability to cure bone diseases. The present study evaluated the osteogenic effects of anhydroicaritin (1) and 2″-hydroxy-3″-en-anhydroicaritin (2) isolated from E. brevicornu by activity-guided assay. Treatment with1 and 2 improved the proliferation of murine osteoblastic MC3T3-E1 cells at doses of 10−7-10−5 mol/L and 10−7-10−6 mol/L, respectively, in the 72-hour culture period. Enzyme linked immunosorbent assay and histochemical staining demonstrated that both of these two prenyl-flavonoids significantly promoted the differentiation of MC3T3-E1 cells by enhancing the level of ALP activity in the cells. Alizarin Red staining and mineralized nodule quantification showed that 1 and 2 had the potential of stimulating the formation of mineralization nodules and further speeding up the formation of bone, indicating that both compounds might be potential candidates for bone regenerative medicine.
Chemical and Biological Investigation of Some Secondary Metabolites in Atriplex Halimus Growing in Egypt
Authors: Kabbash Amal , Shoeib Nagwa
Published: March 2019

The n-BuOH-soluble fraction of the MeOH-CH2Cl2 (1:1) extract of the aerial parts of Egyptian Atriplex halimus L. yielded two new flavonol glycosides, designated as atriplexoside A (1) [3′- O-methylquercetin-4′- O-β-apiofuranoside-3- O-(6″- O-α-rhamnopyranosyl-β-glucopyranoside)] and atriplexoside B (2) [3′- O-methylquercetin-4′- O-(5″″- O-β-xylopyranosyl-β-apiofuranoside)-3- O-(6″- O-α-rhamnopyranosyl-β-glucopyranoside)], together with six known compounds: two phenolic glucosides (3, 4), one ecdysteroid (5), one megastigmane (6) and two methoxylated flavonoid glycosides (7, 8). The structures of the compounds were elucidated by detailed spectroscopic analysis, including HR-ESI-MS and 2D-NMR spectroscopic data. DPPH radical scavenging, antileishmanial and anti-multidrug resistance activities were investigated using the n-BuOH-soluble fraction as well as the isolated compounds. Compound 8 (5- O-methylquercetin-3- O-(6″- O-α-rhamnopyranosyl-β-glucopyranoside) presented marked DPPH radical scavenging, weak antileishmanial and anti-multidrug resistance activity while the other tested compounds showed weaker activities.
Rotenoid Derivatives from Derris Trifoliata with Nitric Oxide Production Inhibitory Activity
Authors: Ito Chihiro , Murata Tomiyasu , Tan Hugh T.-W. , Kaneda Norio , Furukawa Hiroshi , Itoigawa Masataka
Published: March 2019

Study of the chemical constituents of the stems of Derris trifoliata Lour. (Leguminosae) collected in Singapore led to the isolation and identification of three known and two new rotenoid derivatives. The new derivatives, named derrisfolin A (1) and B (2), inhibited nitric oxide production in murine macrophage-like RAW 264.7 cells stimulated with interferon-γ and lipopolysaccharide.
Glycoglycerolipids from Stellera Chamaejasme
Authors: Liu Liping , Zhang Junqi , Wang Xiaoyang , Wang Hongbing
Published: March 2019

Two new glycoglycerolipids (1 and 2), along with three known compounds (3-5) were isolated from Stellera chamaejasme. The structure of the new compounds was elucidated by chemical and spectroscopic data analysis. The cytotoxic activity of 1-3 was evaluated and showed no activity against the assayed human cancer cell lines.
Chemical Composition, Antioxidant Properties and Antimicrobial Activity of the Essential Oil of Murraya Paniculata Leaves from the Mountains of Central Cuba
Authors: Rodríguez Elisa Jorge , Ramis-Ramos Guillermo , Heyden Yvan Vander , Simó-Alfonso Ernesto F. , Lerma-García María Jesús , Saucedo-Hernández Yanelis , Monteagudo Urbano , Morales Yeni , Holgado Beatriz , Herrero-Martínez José Manuel
Published: March 2019

The essential oil of Murraya paniculata L leaves from the mountains of the Central Region of Cuba, obtained by hydrodistillation, was analyzed by gas chromatography-mass spectrometry. Eighteen compounds, accounting for 95.1% of the oil were identified. The major component was β-caryophyllene (ca. 30%). The antioxidant activity of essential oil was evaluated against Cucurbita seed oil by peroxide, thiobarbituric acid and p-anisidine methods. The essential oil showed stronger antioxidant activity than that of butylated hydroxyanisole and butylated hydroxytoluene, but lower than that of propyl gallate. Moreover, this antioxidant activity was supported by the complementary antioxidant assay in the linoleic acid system and 2, 2′-diphenyl-1-picrylhydrazyl. The essential oil also showed good to moderate inhibitory effects against Klebsiella pneumoniae and Bacillus subtilis.
Effects of Inhaled Lavender Essential Oil on Stress-Loaded Animals: Changes in Anxiety-Related Behavior and Expression Levels of Selected mRNAs and Proteins
Authors: Takahashi Mizuho , Yoshino Akiharu , Yamanaka Ayako , Asanuma Chihiro , Satou Tadaaki , Hayashi Shinichiro , Masuo Yoshinori , Sadamoto Kiyomi , Koike Kazuo
Published: March 2019

Inhalation of various essential oils elicits behavioral changes as a consequence of a complex centrally coordinated response. To understand the molecular mechanisms of action of aromatic compounds on emotional responses, we evaluated the stress-induced changes in mouse brain and the efficacy of inhaled essential oil from Lavandula officinalis (LvEO) using two approaches: a behavioral test, and examining the expression levels of selected genes {fast nerve growth factor receptor (NGFR) mRNA, activity regulated cytoskeletal-associated protein (Arc) mRNA} and proteins {galactokinase 1 (GLK1) and brain-derived neurotrophic factor (BDNF)}. Animals were randomly divided into 4 groups depending on the treatment given: stress (-)/H2O, stress (-)/LvEO, stress (+)/H2O, and stress (+)/LvEO group. For behavioral testing, using an elevated plus-maze test, significant anxiolytic-like effects were seen in both the stress (-)/LvEO and stress (+)/LvEO groups, indicating that LvEO exerts anxiolytic-like effects regardless of the administration of water immersion stress. On expression analysis, the levels of NGFR and Arc mRNA were significantly lower in animals subjected to stress. Inhalation of LvEO, however, reversed this change, thus suggesting that LvEO negates the impact of stress on gene expression levels. Meanwhile, significant decreases in expression levels were also observed in the stress (-)/LvEO group, which implies that LvEO, when given in a stress-free situation, may act as a stress stimulus. Taken together, our data suggest that inhalation of LvEO exerts bidirectional influences in the central nervous system (CNS) of animals, either attenuating the effects of stress or acting as a stressor, depending on the subject state.
Chemical Constituents of Ligularia Nelumbifolia and L. Subspicata Hybrid Collected in Shangrila County, Yunnan Province of China
Authors: Hanai Ryo , Yamada Hiroka , Suzuki Yurika , Nagano Hajime , Kawahara Takayuki , Yu Jiao-Jun , Gong Xun , Kuroda Chiaki
Published: March 2019

Four Ligularia individuals possessing morphological characters of both L. nelumbifolia and L. subspicata were discovered in Shangrila County, Yunnan Province, China. DNA sequencing showed that the specimens were hybrids of the two species and their maternal parent was L. subspicata. The chemical composition of the root extract was examined for three of them as well as L. nelumbifolia and L. subspicata collected sympatrically. Nelumol was isolated from L. nelumbifolia, and furanoeremophilanes from L. subspicata. While nelumol and furanoeremophilanes were detected in two of the hybrid samples, only furanoeremophilanes were detected in the others.
ACAT Inhibitory Activity of Exudates from Calocedrus Macrolepis Var. Formosana
Authors: Hsieh Yu-Hsin , Chen Kuan-Jung , Chien Shih-Chang , Cheng Wen-Ling , Xiao Jun-Hong , Wang Sheng-Yang
Published: March 2019

Cholesterol acyltransferase (ACAT) is an enzyme controlling cholesterol esterification in cells. Large amounts of cholesterol esters accumulate in macrophages and smooth muscle cells of blood vessel walls resulting in the initial stages of atherosclerosis. Thus, atherosclerosis might be inhibited through inhibition of the activity of ACAT. In the present study, we identified by spectral analysis and chromatographic quantification that ferruginol was the most abundant component of exudates secreted from the wounding site of Calocedrus macrolepis Kurz var. formosana. Results obtained from the cholesterol absorption assay revealed that ferruginol exhibited a significant inhibitory activity on cholesterol absorption in mice macrophages (RAW 264.7 cell). Based on the results from analyzing the ratio of cholesterol esterification, ferruginol dose-dependently suppressed cholesterol esterification and the IC50 value was 2.0 μg/mL. In conclusion, ferruginol revealed strong inhibitory activities that retarded the absorption and esterification of cholesterol in cells. Our finding indicates that ferruginol might possess a potential for development as a pharmaceutical product for preventing arteriosclerosis.
Two Novel Phenethylamine Alkaloids from Streptomyces sp. YIM10049
Authors: Yang Xueqiong , He Guangwei , Zhao Lixing , Yang Yabin , Liu Yun , Xu Lihua , Ding Zhongtao
Published: March 2019

Two novel phenethylamine alkaloids were isolated from Streptomyces sp. YIM 10049. On the basis of spectral data, their structures were determined as (S)-N- (α-phenylethyl)-2-hydroxyl-acrylimine (1) and (S)-N-nitroso-1-amino- p-hydroxy phenylethanol (2). Three known compounds, indole-3-carboxylic acid (3), cyclo(L-Ala-L-Tyr)(4), and bis(2-ethylhexyl) phthalate (5), were also isolated and characterized. Compound 1 is a rare enol tautomer, and compound 2 an unusual phenethylamine alkaloid with a N-NO group.
Flavonoids and Triterpenes from the Leaves of Artocarpus Fulvicortex
Authors: Jamil Shajarahtunnur , Taher Muhammad , Sirat Hasnah M. , Othman Nur Azlin
Published: March 2019

Five flavonoids, 5-hydroxy-(6:7,3′:4′)-di(2,2-dimethylpyrano)flavone 1, carpachromene 2, cycloartocarpesin 3, norartocarpetin 4 and 2′-hydroxy-4,4′,6′- trimethoxychalcone 5, along with three triterpenes, friedelin 6, lupeol 7 and β-sitosterol 8 were isolated for the first time from the leaves of Artocarpus fulvicortex F.M. Jarrett. The structures of these compounds were established by analysis of their spectroscopic (1D and 2D NMR) and spectrometric (MS) data, as well as by comparison of these with those reported in the literature.
Dihydrospinochalcone-A and Epi-Flemistrictin-B, Natural Isocordoin Derivatives from the Root Extract of Lonchocarpus Xuul
Authors: Escalante-Erosa Fabiola , González-Morales Brenda , Quijano-Quiñones Ramiro F. , Miron-López Gumersindo , Peña-Rodríguez Luis M.
Published: March 2019

Purification of the root extract of Lonchocarpus xuul resulted in the isolation and identification of dihydrospinochalcone A (1) and epi-flemistrictin B (2) as additional natural isocordoin derivatives. Identification was based on the analysis of their spectroscopic data and by comparing these with those of previously reported metabolites.
Exploitation of the Antioxidant Potential of Geranium Macrorrhizum (Geraniaceae): Hepatoprotective and Antimicrobial Activities
Authors: Radulović Niko S. , Stojković Milan B. , Mitić Snežana S. , Randjelović Pavle J. , Ilić Ivan R. , Stojanović Nikola M. , Stojanović-Radić Zorica Z.
Published: March 2019

In this study we evaluated in vitro (radical scavenging) and in vivo (hepatoprotective effect) antioxidant activities and antimicrobial properties of the extracts of the above- and underground parts of Geranium macrorrhizum L. (Geraniaceae), an ethnopharmacologically renowned plant species. The antioxidant activity and total phenol and flavonoid contents of four different solvent extracts were evaluated by seven different methods. The methanol extracts, administered i.p. to rats (120-480 mg/kg), were evaluated for hepatoprotective activity in a CCl4-induced hepatotoxicity model. The same extracts were tested for antimicrobial activity against seven bacterial and two fungal species. The administered methanol extracts with the highest antioxidant potential showed a significant dose-dependent hepatoprotective action against CCl4-induced liver damage in both decreasing the levels of liver transaminases and bilirubin and in reducing the extent of morphological malformations of the liver. The leaf methanol extract displayed a very strong antibacterial activity, especially against Staphylococcus aureus, with low minimal inhibitory and bactericidal concentrations. These results justify the frequent use of this plant species in folk medicine. Besides the known astringent effect, one can expect that the observed antimicrobial activity against several human pathogens contributes to the wound healing properties of this plant.
Anti-neutrophilic Inflammatory Secondary Metabolites from the Traditional Chinese Medicine, Tiankuizi
Authors: Lee Chia-Lin , Hwang Tsong-Long , Peng Chieh-Yu , Chen Chao-Jung , Chang Yuan-Shiun , Wu Yang-Chang
Published: March 2019

Through bioassay-guided fractionation, thirteen compounds (1-13) were isolated from the dry root of Semiaquilegia adoxoides, known as Tiankuizi in traditional Chinese medicine (TCM). Among these, four benzoic acid derivatives (1, 2, 4, 5), one 4,6-dimethoxy-5-methyl-2 H-pyran-2-one (10) and one 1,2,3-propanetriol (13) were found for the first time in S. adoxoides. This is the first record of compound 10 from a natural source. 4-Hydroxybenzoic acid (1) and 3,4-dihyroxybenzoic acid (2) showed selective inhibition against elastase release and superoxide anion generation, with IC50 values of 3.20 and 6.21 μg/mL, respectively. Compound 1 had 7-fold better activity than the positive control against elastase release induced by human neutrophils. Overall, our studies demonstrated Tiankuizi (S. adoxoides) as a potential TCM and isolates 1 and 2 as promising lead compounds for neutrophilic inflammatory diseases.
Synthesis, Antifungal Activity and Structure-Activity Relationships of Vanillin Oxime-N-O-Alkanoates
Authors: Ahluwalia Vivek , Garg Nandini , Kumar Birendra , Walia Suresh , Sati Om P.
Published: March 2019

Vanillin oxime- N-O-alkanoates were synthesized following reaction of vanillin with hydroxylamine hydrochloride, followed by reaction of the resultant oxime with acyl chlorides. The structures of the compounds were confirmed by IR, 1H, 13C NMR and mass spectral data. The test compounds were evaluated for their in vitro antifungal activity against three phytopathogenic fungi Macrophomina phaseolina, Rhizoctonia solani and Sclerotium rolfsii by the poisoned food technique. The moderate antifungal activity of vanillin was slightly increased following its conversion to vanillin oxime, but significantly increased after conversion of the oxime to oxime- N-O-alkanoates. While vanillin oxime- N-O-dodecanoate with an EC50 value 73.1 μg/mL was most active against M. phaseolina, vanillin oxime- N-O-nonanoate with EC50 of value 66.7 μg/mL was most active against R. solani. The activity increased with increases in the acyl chain length and was maximal with an acyl chain length of nine carbons.