bluuebunny/crossref_metadata_2025 huggingface dataset:
Antibacterial Activities of Endophytic Fungi Isolated from Mentha cordifolia Leaves and Their Volatile Constituents
Authors: Monggoot Sakon , Burawat Jariya , Pripdeevech Patcharee
Published: March 2019

A total of 17 endophytic fungal isolates were obtained from the leaves of Mentha cordifolia Opiz (Lamiaceae). Seven isolates were identified to the level of genus by using taxonomically relevant morphological traits. Colletotrichum and Phomopsis species were dominant among these strains. All strains were separated from M. cordifolia leaf for the first time. The ethyl acetate extracts of all endophytic fungi were tested for antibacterial activity against Salmonella typhimurium TISTR1166 and Pseudomonas aeruginosa TISTR781. Most endophytes exhibited antibacterial activity. Ustilago sp. MFLUCC15-1024 presented the highest inhibition zone diameter with a MIC of 31.25 μg/mL against the tested pathogens. The chemical composition of the ethyl acetate extract of this strain was investigated using gas chromatography-mass spectrometry. Twenty-one components were identified. 2-Phenylethanol (38.7%), E-ligustilide (12.4%), α-eudesmol (10.2%), β-vetivone (4.6%), β-ylangene (3.7%) and verbanol (3.4%) were the major components of the extract. The strong antibacterial activity of Ustilago sp. MFLUCC15-1024 ethyl acetate extract may be attributed to the presence of a high concentration of bioactive compounds including phenyl ethyl alcohol, E-ligustilide and α-eudesmol. The results indicate that there is high diversity of endophytic fungi in M. cordifolia leaf, and that Ustilago sp. MFLUCC15-1024 strain could be an excellent resource of natural antibacterial compounds.
Chemical Composition and Anti-phytopathogenic Activity of the Essential Oil of Beilschmiedia miersii
Authors: Carvajal Marcela A. , Vergara Alejandra P. , Santander Rocío , Osorio Mauricio E.
Published: March 2019

Beilschmiedia miersii (Gay) Kosterm. (Lauraceae) (“Belloto del Norte”) is a little-studied tree endemic of the Central Zone of Chile. Hydrodistillation of leaves and stem bark of B. miersii yielded 0.2% essential oil. GC-MS analysis allowed identification of 31 components. The most abundant compounds were three phenylpropanoids: Sarisan (45.8%), eugenol methyl ether (27.7%) and safrole (5.8%). The oil of B. miersii showed high antioxidant content (TEAC: 750.8 ± 9.6 μmol/100 g of essential oil). The anti-phytopathogenic activity was evaluated against pathogens of plants: Fungi (Botrytis cinerea, Gibberella fujikuroi and Phytophthora cinnamomi) and bacteria: (Erwinia carotovora, Pseudomonas syringae and Agrobacterium tumefaciens). The oil showed anti-phytopathogenic activity against all tested bacteria and fungi, especially against A tumefaciens (IC50 = 5 μg / mL) and P. cinnamomi (IC50 = 200 μg / mL). This study demonstrates that the essential oil of B. miersii has great potential for applications in food and agricultural industries.
11-Hydroxy-2,4-cycloeudesmane from the Leaf Oil of Juglans regia and Evaluation of its Larvicidal Activity
Authors: Köroğlu Ayşegül , Baldemir Ayşe , Özek Gülmira , Bedir Erdal , Tabanca Nurhayat , Ali Abbas , Khan Ikhlas A. , Başer Kemal Hüsnü Can , Özek Temel
Published: March 2019

Leaves of Juglans regia L. collected from two different locations [Adana (A) and Ankara (B)] from Turkey were subjected to hydrodistillation in a Clevenger type apparatus to yield the essential oils (EOs). GC/MS and GC-FID analyses revealed that the A EO was rich in thymol (23.1%), while caryophyllene oxide (33.8%) was found as the main constituent of B EO. Both contained β-eudesmol (1.4% - 9.5 %), ( E)-geranyl acetone (3.7% - 5.8%) and the eudesmane type constituent juglaterpene A (3.1% - 11.0%). Using a HP Innowax preparative capillary column connected to a preparative fraction collector, an unknown constituent, juglaterpene A (1, 11-hydroxy-2,4-cycloeudesmane), was isolated in a rapid one-step manner with > 94.0% purity. Structure determination was accomplished from 1D- and 2D-NMR spectroscopic data. Oil B demonstrated significant larvicidal activity against 1st instar Aedes aegypti L.
Cytotoxic Effects of Resveratrol, Rutin and Rosmarinic Acid on ARH–77 Human (Multiple Myeloma) Cell Line
Authors: Canturk Zerrin , Dikmen Miris , Artagan Oge , Ozarda Mustafa Guclu , Ozturk Nilgun
Published: March 2019

Multiple myeloma (MM) cancers are 10% of hematological cancers. Leukemia ARH-77 is a malignancy like MM with a worse course of disease and the survival rate from it is very low. Therefore, ARH-77 is a commonly used model for antitumor agent studies. Polyphenolic compounds, such as resveratrol, rutin and rosmarinic acid, have many protective roles, but there is no comparative study about these three polyphenolic compounds on ARH-77. In the present study, we investigated the cytotoxic effects of resveratrol, rutin and rosmarinic acid on ARH-77. Toxic concentration ranges were determined by the brine shrimp lethality test on Artemia salina. In addition, for determination of their cytotoxic effects, MTT and NR methods were used for ARH-77. Resveratrol caused significant reduction in both mitochondrial and lysosomal activities compared with the control group. Maximum inhibition values were detected on mitochondrial and lysosomal activity with 200 μM concentrations after 48 hours. After a 24 hours incubation period, rutin showed cytotoxic effects, particularly with 50, 100 and 200 μM concentrations. Rosmarinic acid also decreased the mitochondrial activity with the same concentrations. Resveratrol showed higher cytotoxic effects than rutin and rosmarinic acid. According to our study, polyphenolic compounds such as rutin, resveratrol and rosmarinic acid may hold promise in multiple myeloma treatment with further investigations.
Enzyme-hydrolyzed Fruit of Jurinea mollis: A Rich Source of (-)-(8R,8′R)-Arctigenin
Authors: Könye Rita , Ress Ágnes Evelin , Sólyomváry Anna , Tóth Gergő , Darcsi András , Komjáti Balázs , Horváth Péter , Noszál Béla , Molnár-Perl Ibolya , Béni Szabolcs , Boldizsár Imre
Published: March 2019

In Jurinea mollis fruit, the dibenzylbutyrolactone-type lignan glycoside arctiin and its aglycone arctigenin were determined for the first time using a combination of optimized enzymatic treatment and complementary spectrometric (HPLC-MS, GC-MS) and spectroscopic (CD and NMR) methods. Analysis of separated fruit parts, i.e., the fruit wall and embryo, demonstrated the specific accumulation of arctiin, since it was exclusively found in the embryo. Arctiin in the embryo samples (71.5 mg/g) was found to be quantitatively converted into arctigenin (50.7 mg/g) by endogenous enzymatic hydrolysis, resulting in one of the highest arctigenin-containing plant tissues reported to date and allowing the selective isolation of arctigenin by our recently reported three-step isolation method. The absolute configuration of the isolated arctigenin was determined to be (-)-(8 R,8′ R). Conformational analysis of arctigenin was also performed, resulting in three major low energy conformations.
Identification and in vitro Evaluation of Lipids from Sclerotia of Lignosus rhinocerotis for Antioxidant and Anti-neuroinflammatory Activities
Authors: Nallathamby Neeranjini , Serm Lee Guan , Raman Jegadeesh , Malek Sri Nurestri Abd , Vidyadaran Sharmili , Naidu Murali , Kuppusamy Umah Rani , Sabaratnam Vikineswary
Published: March 2019

Lignosus rhinocerotis (Cooke) Ryvarden (Tiger milk mushroom) is traditionally used to treat inflammation triggered symptoms and illnesses such as cough, fever and asthma. The present study evaluated the in vitro antioxidant, cytotoxic and anti-neuroinflammatory activities of the extract and fractions of sclerotia powder of L. rhinocerotis on brain microglial (BV2) cells. The ethyl acetate fraction had a total phenolic content of 0.30 ± 0.11 mg GAE/g. This fraction had ferric reducing capacity of 61.8 ± 1.8 mg FSE/g, ABTS•+ scavenging activity of 36.8 ± 1.8 mg TE/g and DPPH free radical scavenging activity of 21.8% ± 0.7. At doses ranging from 0.1 μg/mL – 100 μg/mL, the extract and fractions were not cytotoxic to BV2 cells. At 100 μg/mL, the crude hydroethanolic extract and the ethyl acetate fraction elicited the highest nitric oxide reduction activities of 68.7% and 58.2%, respectively. Linoleic and oleic acids were the major lipid constituents in the ethyl acetate fraction based on FID and GC-MS analysis. Linoleic acid reduced nitric oxide production and down regulated the expression of neuroinflammatory iNOS and COX2 genes in BV2 cells.
Exploitation of Artemisia arborescens as a Renewable Source of Chamazulene: Seasonal Variation and Distillation Conditions
Authors: Michelakis Evangelos C. , Evergetis Epameinondas , Koulocheri Sofia D. , Haroutounian Serkos A.
Published: March 2019

Tree Wormwood ( Artemisia arborescens L.) is a Mediterranean medicinal herb known for its anti-inflammatory properties, mainly because of the high chamazulene content of its essential oil (EO). Herein are presented the results of an investigation concerning the seasonal variation in the chamazulene content of the EOs of three Cretan natural populations of A. arborescens by combined GC-FID and GC-MS analysis. Results highlighted a population containing EO rich in chamazulene at amounts exceeding 50% of its quantitative composition at the full flowering stage, which is the more appropriate vegetative stage for harvesting. Hydro-distillation of the respective plant material in five different pH environments increased, in all cases, the chamazulene yield, with the most efficient pH value being 8.3, when the chamazulene amount increased 1.3 times compared with distillation under neutral conditions, reaching 65.1% of the total content of EO.
Preparative Capillary GC for Characterization of Five Dracocephalum Essential Oils from Mongolia, and their Mosquito Larvicidal Activity
Authors: Özek Gülmira , Tabanca Nurhayat , Radwan Mohammed M. , Shatar Sanduin , Altantsetseg Altaa , Baatar Dumaajav , Başer Kemal H.C. , Becnel James J. , Özek Temel
Published: March 2019

The chemical composition and mosquito larvicidal and adulticidal activity of five essential oils (EOs), Dracocephalum ruyschiana L. (DR), D. foetidum Bunge (DF), D. moldavica L. (DM), D. fruticulosum Steph. ex Willd. (DFr) and D. peregrinum L. (DP) were evaluated. Simultaneous GC-FID and GC-MS analyses revealed in the EOs of DR, DF and DM an unidentified compound (1) ([M+122], 5.4%, 57.9% and 74.0%, respectively). Therefore, we aimed to isolate compound 1 using Preparative Capillary GC (PCGC) connected to a Preparative Fraction Collector (PFC) system. Structure determination of 1 was determined by 1H- and 13C-NMR as p-mentha-1,8-dien-10-al (1, limonen-10-al). Other detected major constituents were thymol (34.0%) and carvacrol (6.1%) in DR; limonene (28.8%) in DF; cis-chrysanthenol acetate (29.1%) and trans-verbenol (5.0%) in DFr; and linalool (17.9%), trans-β-bergamotene (7.9%), (E)-nerolidol (7.7%) and eugenol (5.5%) in DP. The DFr, DP, DR and DM EOs produced 100% mortality to 1st instar larvae of Aedes aegypti L. at 250 ppm and DR and DM EO exhibited the strongest activity and killed 100% 1st instar larvae at 62.5 ppm. No adulticidal activity was observed against female Ae. aegypti. In the scope of the present study, for the first time isolation of limonen-10-al (1) from DR, DM, and DP EOs and larvicidal activity of five Dracocephalum EOs were reported.
Influence of Essential Ginger Oil on Human Psychophysiology after Inhalation and Dermal Application
Authors: Stappen Iris , Hoelzl Anna-Sofie , Randjelovic Olivera , Wanner Juergen
Published: March 2019

The influence of essential ginger oil ( Zingiberis aetheroleum from Zingiber officinale Roscoe) on blood pressure, heart rate and subjective well-being was investigated after inhalation and dermal application on healthy human subjects in two experiments. Additionally a GC-MS analysis of the tested oil is given. The essential oil exhibited a high amount of citral (19.4%). α-Zingiberene (17.4%), camphene (7.8%), trans, trans-α-farnesene (6.8%) and β-bisabolene (5.8%) were also prominent constituents. Compared with the control condition an activating effect was observed for ginger oil in the inhalation experiment.
Synthetic Anthocyanidins from Natural Benzopyrans
Authors: Kraus George A. , Geraskin Ivan M.
Published: March 2019

A hydride abstraction strategy can be used to make anthocyanidins and isoflavylium salts from benzopyrans in good yields.
Anti-inflammatory Effects of Compounds from Polygonum odoratum
Authors: Okonogi Siriporn , Kheawfu Kantaporn , Holzer Wolfgang , Unger Frank M. , Viernstein Helmut , Mueller Monika
Published: March 2019

Polygonum odoratum is an edible plant traditionally used as an antidiabetic, antimicrobial, anti-inflammatory, and antitumor agent in Asia. The aim of the study was to evaluate the anti-inflammatory effect of P. odoratum and the isolation and characterization of its main fractions. Extracts of the aerial parts were tested for anti-inflammatory activity as indicated by a change in the cytokine secretion in lipopolysaccharide-stimulated macrophages. After separation of the extract by reversed-phase high-performance liquid chromatography, the anti-inflammatory activity of the fractions was determined. Furthermore, the two main fractions were identified by nuclear magnetic resonance spectroscopy (1H- and 13C-NMR). The ethanolic extract significantly reduced IL-6 secretion (IC50 25 μg/mL). The two main fractions (5 and 7) significantly decreased IL-6 production with an IC50 of 102 μM (5) and 77 μM (7), respectively, and were identified as scutellarein-7-glucoside (5) and quercitrin (7). Since inflammation plays a major role in various diseases with high prevalence globally, it may be of importance that P. odoratum and its main constituents scutellarein-7-glucoside and quercitrin can be used as either an alternative or complementary treatment. Additionally, both are glycosides and their activity may be enhanced tremendously by deglycosylation by the gut microbiota.
Chemical Composition of Vietnamese Essential Oils of Cinnamomum rigidifolium, Dasymaschalon longiusculum, Fissistigma maclurei and Goniothalamus albiflorus
Authors: Wanner Juergen K.R. , Dai Do N. , Huong Le T. , Hung Nguyen V. , Schmidt Erich , Jirovetz Leopold
Published: March 2019

Cinnamomum rigidifolium, Dasymaschalon longiusculum, Fissistigma maclurei and Goniothalamus albiflorus were collected from different landscapes in Vietnam and hydro distilled to produce essential oils with yields from 0.15 – 0.35%. The oils were analyzed by GC-MS-FID and rechecked by measurements on two different instrumentation configurations. The main components of the studied essential oils were for Cinnamomum rigidifolium linalool (19.4%), α-pinene (13.8%), verbenone (9.9%) and cis-verbenol (8.9%), total identified 90.5%; for Dasymaschalon longiusculum spathulenol (21.4%), caryophyllene oxide (17.6%), α-pinene (5.5%) and β-pinene (5.2%), total identified 70.1%; for Fissistigma maclurei spathulenol (17.8%), guaia-6,10(14)-diene-4β-ol (10.3%), (E)-β-caryophyllene (7.3%) and caryophyllene oxide (7.0%), total identified 75.3% and for Goniothalamus albiflorus 1,8-cineole (13.2%), α-pinene (10.6%), ledol (7.5%) and caryophyllene oxide (7.3%), total identified 78.0%.
Chemical Composition, Antioxidant, Antimicrobial and Insecticidal Activities of Essential Oil from a Moroccan Endemic Plant: Bubonium imbricatum
Authors: Aghraz Abdellah , Wanner Jürgen , Schmidt Erich , Aitdra Loubna , Aitsidibrahim Malika , Tabanca Nurhayat , Abbas Ali , Hassani Lahcen , Markouk Mohammed , Jirovetz Leopold , Larhsini Mustapha
Published: March 2019

The chemical composition, antioxidant, antimicrobial and insecticidal properties of essential oil obtained by hydro-distillation from Bubonium imbricatum Cav. have been investigated. The essential oil of aerial parts was analyzed by GC-FID and GC-MS. A total of 63 compounds were identified representing more than 82% of the oil. The major components were cis-chrysanthenyl acetate (31.2%) and thymol isobutyrate (3.4%). The antioxidant activity was evaluated by the DPPH and reducing power test. The data showed moderate activity compared with the reference compounds. Our results showed strong activity of the investigated oil against all tested microorganisms. The highest antibacterial activity was observed against Bacillus subtilis (inhibition zone= 18 ± 0.21, MIC= 0.18 mg/mL). In general, Gram-positive bacteria were more susceptible than Gram-negative ones. Candida parapsilosis was the most sensitive among the Candida strains tested. LD50 and LD90 values were 33.1 and 53.1 ppm against 1-d-old larvae of Aedes aegypti L.
Mint Flavorings from Candies Inhibit the Infectivity of Chlamydia pneumoniae
Authors: Hanski Leena L. , Kapp Karmen , Tiirola Terttu M. , Orav Anne , Vuorela Heikki J. , Püssa Tõnu , Vuorela Pia M.
Published: March 2019

The impact of solvent extracts from the distillation water (flavoring extracts) isolated from mint flavored candies on the infectivity of the intracellular bacterium Chlamydia pneumoniae was evaluated by an in vitro model of epithelial cell infections. The mint flavoring extracts were isolated from the candies by simultaneous hydrodistillation and their chemical composition, established by GC-MS, demonstrated menthol and limonene as the most abundant components. Results obtained by treating C. pneumoniae elementary bodies (EBs) with the flavoring extracts or pure reference compounds showed a significant decrease in EB infectivity, achieved with most of the extracts. This antichlamydial activity could be related to the relatively high menthol content of the extracts. Overall, the obtained data indicates that the flavorings present in the candies are able to target the metabolically quiet, non-replicating form of the bacterium and to suppress the spread of this respiratory pathogen from one cell to another.
A Guidance Manual for the Toxicity Assessment of Traditional Herbal Medicines
Authors: Aydιn Ahmet , Aktay Göknur , Yesilada Erdem
Published: March 2019

Herbal remedies have been used for thousands of years in worldwide traditional medicines for their potential health benefits. Although they are generally presumed safe unless a significant risk has been identified in humans, increasing number of case reports notify acute or chronic intoxications resulting from their use. This study aims to produce a scientific guide for the evaluation of traditional herbal medicines (THMs) in terms of their toxicity risks based on the published regulatory documents. For this purpose recommended in vitro and in vivo toxicity tests on medicinal products for human use issued by the international regulatory bodies are overviewed and they are then adopted to be used for the toxicity assessment of THMs. Accordingly, based on compilation of these issued regulations, the following tests are recommended for the toxicity assessment of THMs; in vitro cytotoxicity, genotoxicity, acute and repeated dose toxicity, carcinogenicity, reproductive and developmental toxicity, local tolerance tests, toxicokinetic studies, and additional toxicity tests including safety pharmacology, immunotoxicity and antigenicity, endocrine system toxicity, gastro-intestinal toxicity, renal and hepatotoxicity, and drug interaction studies. This study describes and discusses the applicability of these tests for the risk assessment in THMs.
Synthesis and Cytotoxic Evaluation of Artemisinin–triazole Hybrids
Authors: Tien Doan Duy , Giang Le Nhat Thuy , Anh Dang Thi Tuyet , Dung Nguyen Tien , Ha Thanh Nguyen , Ha Nguyen Thi Thu , Phuong Hoang Thi , Chinh Pham The , Van Kiem Phan , Van Tuyen Nguyen
Published: March 2019

Dihydroartemisinin was converted to its corresponding alkyne-functionalized esters, which were subsequently deployed as substrates for a ‘click’ chemistry-mediated coupling with 3′-azido-3′-deoxythydimine (AZT) to furnish novel triazole–artesunate–AZT hybrid compounds. Moreover, various substituted triazole–artemisinin hybrids were synthesized based on ‘click’ chemistry between propargyl-substituted derivatives and artemisinin containing a 2-hydroxypropane unit. Fourteen new hybrids were thus successfully prepared and evaluated as cytotoxic agents, revealing an interesting anticancer activity of four triazole–artemisinin derivative hybrids in KB and HepG2 cancer cell lines.
Mitochondrial Target of Nobiletin's Action
Authors: Sharikadze Nino , Jojua Natia , Sepashvili Maia , Zhuravliova Elene , Mikeladze David G
Published: March 2019

Nobiletin is an O-methylated flavonoid found in citrus peels that have anticancer, antiviral, neuroprotective, anti-inflammatory activities and depending on the cell types exhibits both pro- or anti-apoptotic properties. We have found that nobiletin decreases oxygen consumption by bovine brain isolated mitochondria in the presence of glutamate and malate and increases in the presence of succinate. In parallel, nobiletin increases NADH oxidation, a-ketoglutarate dehydrogenase activities and through matrix substrate-level phosphorylation elevates the a-ketoglutarate-dependent production of ATP. In addition, nobiletin reduces the production of peroxides in the presence of complex I substrates and slightly enhances succinate-driven H2O2 formation. Besides, nobiletin induces transient elevation of membrane potential followed by mild depolarization. Affinity purified nobiletin binding proteins revealed one major anti-NDUFV1 positive protein with 52kD and NADH: ubiquinone oxidoreductase activity. This fraction can produce peroxide that is inhibited by nobiletin. We propose that nobiletin may act as a mild “uncoupler”, which through activation of a-ketoglutarate dehydrogenase (a-KGDH)-complex and acceleration of matrix substrate-level phosphorylation maintains membrane potential at an abnormal level. This switch in mitochondrial metabolism could elevate succinate-driven oxygen consumption that may underlay in both pro- and anti-apoptotic effects of nobiletin.
Inhibition of the MAPK Signaling Pathway by Red Rice Extract in UVB-irradiated Human Skin Fibroblasts
Authors: Limtrakul Pornngarm , Yodkeeree Supachai , Punfa Wanisa , Srisomboon Jatupol
Published: March 2019

Red rice has demonstrated several biological properties including anti-oxidant and anti-inflammation properties. However, the anti-photoaging activity has not yet been investigated. The aim of this study relates to the photo-protective effects of red rice extract (RRE) on UVB-induced skin aging. RRE was prepared and the active compounds and anti-oxidant activity were determined. The cytotoxicity of fibroblasts and secretions of IL-6 and IL-8 were evaluated. The effects of RRE on collagen and hyaluronic acid (HA) synthesis from fibroblasts were evaluated. Then, the collagenase and MMP-2 activity was determined. The effect of RRE on UV-induced MMP-1, nuclear factor kappa B (NF-κB), activator protein-1 (AP-1) and phosphorylation of MAPK protein expression was determined by western blot analysis. The RRE exerted a free radical scavenging property. RRE significantly increased collagen and HA synthesis in UVB-irradiated human fibroblasts. Moreover, RRE significantly inhibited UVB induced MMP-1 expression, MMP-2 and collagenase activity. Upon UVB irradiation, mitogen activated protein kinases (MAPKs) is activated and this pathway stimulates the expression of interleukin-6 and-8 (IL-6 and-8). Our results show that RRE decreases UVB-induced IL-6 and -8 production and the phosphorylation of c-Jun NH2-terminal kinase (JNK) and the p38 MAPK signaling process. In addition, RRE reduced UVB-induced activation of NF-κB and AP-1. RRE could suppress UV-induced inflammation and skin aging via the inhibition of the MAPK signaling pathway leading to the decrease of NF-κB and AP-1 activation resulting in a decrease in ECM degradation and an increase in ECM synthesis.
Composition and Antimicrobial Activity of the Essential Oils of Three Plant Species from the Sabana of Bogota (Colombia): Myrcianthes leucoxyla, Vallea stipularis and Phyllanthus salviifolius
Authors: Ospina Luis Miguel Pombo , Muñoz Paola Borrego , Matulevich Javier , Teherán Aníbal Alfonso , Villamizar Leidy Barajas
Published: March 2019

In recent decades, essential oils (EOs) have become an important alternative source of antimicrobial agents. The objective of this study was to evaluate the antimicrobial activity of EOs obtained from the leaves of Myrcianthes leucoxyla Mc. Vaughn., Vallea stipularis L.f and Phyllanthus salviifolius Kunth for prevalent microbial strains and also to contribute to the knowledge of their chemical composition. EOs were obtained by hydrodistillation and analyzed by GC-MS. The main compounds for V. stipularis EO were α-tujene (6.6%) and cedrene epoxide (12.0%), for M. leucoxila EO 1,8 cineole (6.3%) and caryophyllene oxide (21.7%), and for P. salviifolius aristolene (17.3%) and geranyl tiglate (15.9%). Antimicrobial tests showed that M. leucoxyla EO was the most active, showing zones of inhibition against all strains used, specifically against Pseudomonas aeruginosa and Salmonella typhimurium with percentages of inhibition higher than 50%. Compared with positive controls, this activity may be related to the presence of 1,8 cineole.
Antimutagenic Effects of Polymethoxy Flavonoids of Citrus unshiu
Authors: Matsumoto Takahiro , Nishikawa Taisuke , Furukawa Ayano , Itano Saki , Tamura Yuka , Hasei Tomohiro , Watanabe Tetsushi
Published: March 2019

Citrus fruits have been used as edible fruit and traditional medicine for various diseases such as cancer. In the courses of our study to find antimutagens, we have found that the ethanolic extract of the peel of Citrus unshiu Marc showed antimutagenic effects against several mutagens in the Ames test using Salmonella typhimurium TA98 strain. Three polymethoxy flavonoids, nobiletin, 3,5,6,7,8,3′,4′-heptamethoxyflavone, and tangeretin, were identified in the extract as major constituents. These three polymethoxy flavonoids showed antimutagenic effects in the Ames test in vitro and in the micronucleus test in vivo.
Comparison of the Qualitative Chemical Composition of Extracts from Ageratina havanensis Collected in Two Different Phenological Stages by FIA-ESI-IT-MSn and UPLC/ESI-MSn: Antiviral Activity
Authors: García Trina H. , da Rocha Claudia Quintino , Dias Marcelo J. , Pino Liudis L. , del Barrio Gloria , Roque Annele , Pérez Caridad E. , dos Santos Lourdes Campaner , Spengler Iraida , Vilegas Wagner
Published: March 2019

The flowers and leaves of Ageratina havanensis (Kunth) R. M. King & H. Robinson are traditionally used as a tea to cure several diseases. The production of active secondary metabolites can be affected by several environmental factors such as climate, altitude, rainfall, phenological stage and other conditions that may influence the growth of plants. In this sense, the development of a methodology to compare the chemical composition of plant extracts is needed. The qualitative chemical composition of the ethyl acetate extracts of flowers and leaves, collected in both reproductive and non-reproductive season, was determined by flow injection analysis-electrospray ionization-ion trap tandem mass spectrometry (FIA-ESI-IT-MSn) and ultra-high-performance liquid chromatography coupled to electrospray negative ionization mass spectrometry (UPLC/ESI-MSn). The qualitative chemical composition of the ethyl acetate extracts of flowers and leaves was very similar in all cases. Also the antiviral activity of flowers against human herpes simplex viruses type 1 and 2 (HSV-1, HSV-2) ( Herpesviridae) was analyzed. Three glucoside flavonoids were isolated from the ethyl acetate extract of the leaves of A. havanensis collected in flowering season using chromatographic methods and their structures were elucidated by physical and spectroscopic data measurements, and by comparing the obtained data with previously published values. The compounds were identified as 3- O-β-D-glucosyl-7-methoxyaromadendrin (5), 7- O-β-D-glucosyl-4′-dihydroxy-5-methoxyflavanone (6) and 5- O-β-D-glucosylsakuranetin (7); this is the first report of the isolation of these compounds in the Asteraceae family. Since the qualitative composition of the extracts of A. havanensis was similar in all cases, it can be expected that the ethyl acetate extract of the leaves collected in the non-reproductive season has anti-herpetic activity similar to that obtained in the reproductive season.
Characterization of the Polyphenolic Profiles of Peel, Flesh and Leaves of Malus domestica Cultivars Using UHPLC-DAD-HESI-MSn
Authors: Petkovska Ana , Gjamovski Viktor , Stanoeva Jasmina Petreska , Stefova Marina
Published: March 2019

Qualitative and quantitative analyses of polyphenols extracted from 21 Malus domestica cultivars using ultra high performance liquid chromatography with diode array detection coupled to heated electrospray ionization mass spectrometric detection was performed for separation of 27 phenolic compounds on a reversed phase UHPLC column with an optimized gradient consisting of 1% formic acid in water and 1% formic acid in methanol within 20 minutes. According to retention times, UV maxima and mass spectra of the peaks in the chromatograms obtained from extracts of apple peel, flesh and leaves, the polyphenolic compounds were identified and quantified. Based on fragmentation patterns, 6 phenolic acids, 5 flavan-3-ols, 5 dihydrochalcones, 8 flavonols and 3 flavone derivatives were characterized in the studied samples. The method was then employed for analysis of the polyphenolic pattern of 21 apple cultivars, both commercial and autochthonous for the Macedonian region, as well as for monitoring the influence of long term storage on the polyphenolic content and composition of apple fruits and for comparison of polyphenolic profiles of apple cultivars during two years of harvesting. The obtained results revealed minor differences in the quality and major variation in the content of phenolic compounds in the flesh, peel and leaves in the studied apple cultivars that is attributed mainly to cultivar differences and meteorological factors.
Chemical Composition, Antioxidant and Anticholinesterase Activities of Gentianella azurea from Russian Federation
Authors: Olennikov Daniil N. , Chirikova Nadezhda K. , Vennos Cecile
Published: March 2019

Phytochemical study of Gentianella azurea (Bunge) Holub (Gentianaceae) collected in Buryatia Republic (Russian Federation) resulted in the isolation of twenty-one compounds including bellidifolin, bellidin, isobellidifolin, norswertianolin, isobellidifolin-8- O-β-D-glucopyranoside, orientin, cynaroside, cosmosiin, apigenin, 4′- O-caffeoylswertiamarin, swertiamarin-6′- O-β-D-glucopyranoside and sweroside, firstly detected in this species. The extracts and individual compounds were shown to possess antioxidant and anticholinesterase potential.
Constituents of Fermented Male Flowers of Alnus sieboldiana (Betulaceae)
Authors: Ghani Nurunajah Ab , Ismail Nor Hadiani , Asakawa Yoshinori
Published: March 2019

Fractionation of the ethyl acetate crude extract of the fermented male flowers of Alnus sieboldiana resulted in the isolation of two diarylheptanoids and six flavonoids. Yashabushidiol A, yashabushidiol B and naringenin were known constituents of the male flowers of A. sieboldiana while kaempferol, quercetin, pinocembrin dimethyl ether, 5,7-dimethoxy-3-hydroxyflavanone and 5,7-dimethoxy-3-hydroxyflavone were isolated for first time from the fermented male flowers of A. sieboldiana. The isolated compounds were characterized using NMR and HRMS and compared with available literature.
(±)-Perforison A, A Pair of New Chromone Enantiomers from Harrisonia perforata
Authors: Yuan Wen-Juan , Gao Wen-Fen , Zhang Jia-Hui , Cao Pei , Zhang Yu , Chen Duo-Zhi , Li Shun-Lin , Di Ying-Tong , Hao Xiao-Jiang
Published: March 2019

(+)-Perforison A and (-)-perforison A, a new pair of chromone enantiomers, along with four known compounds, were isolated from the leaves and stems of Harrisonia perforata. Their structures and absolute configurations were determined on the basis of extensive analysis of spectroscopic data and electronic circular dichroism (ECD) calculations. The cytotoxic activities in vitro of these compounds were evaluated, but none showed significant activity.
Ultrasound and Microwave-Assisted Extraction of Elecampane (Inula helenium) Roots
Authors: Petkova Nadezhda , Ivanov Ivan , Vrancheva Radka , Denev Panteley , Pavlov Atanas
Published: March 2019

The aim of the current research was to perform two “green chemistry” extractions (ultrasound and microwave irradiation) with methanol, 70% (v/v) ethanol and water for extraction of biologically active substances from elecampane ( Inula helenium L.) roots and to compare their contents in all extracts. The presence of carbohydrates (sugars, fructooligosaccharides and inulin), total phenols and flavonoids were established. In vitro antioxidant potential was also evaluated by four assays (DPPH, ABTS, FRAP and CUPRAC). Water extracts obtained by ultrasound-assisted extraction (UAE) showed the highest value of inulin (38 g/100 g dry weight plant material). The highest antioxidant activity was possessed by the 70% (v/v) ethanol extracts obtained by UAE: DPPH – 107.2 mM TE/g dw, ABTS – 86.0 mM TE/g dw, FRAP – 67.0 mM TE/g dw and CUPRAC −173.0 mM TE/g dw, respectively. The reason for this probably depended on the highest content of total phenols in the 70% UAE ethanol extract {7.9 mg GAE/g dw, phenolic acids (chlorogenic, caffeic, p-coumaric, sinapic and ferulic acids)}, especially chlorogenic acid (1.84 mg/g) and flavonoids (quercetin, kaempferol and catechin; 26.4 mg QE/g dw). UAE was evaluated as a promising approach for the simultaneous extraction of bioactive compounds (dietary fibers and antioxidants) from elecampane roots in comparison with microwave irradiation.
ADME/Tox Properties and Biochemical Interactions of Silybin Congeners: In silico Study
Authors: Diukendjieva Antonia , Sharif Merilin Al , Alov Petko , Pencheva Tania , Tsakovska Ivanka , Pajeva Ilza
Published: March 2019

Silymarin, the active constituent of Silybum marianum (milk thistle), and its main component, silybin, are products with well-known hepatoprotective, cytoprotective, antioxidant, and chemopreventative properties. Despite substantial in vitro and in vivo investigations of these flavonolignans, their mechanisms of action and potential toxic effects are not fully defined. In this study we explored important ADME/Tox properties and biochemical interactions of selected flavonolignans using in silico methods. A quantitative structure–activity relationship (QSAR) model based on data from a parallel artificial membrane permeability assay (PAMPA) was used to estimate bioavailability after oral administration. Toxic effects and metabolic transformations were predicted using the knowledge-based expert systems Derek Nexus and Meteor Nexus (Lhasa Ltd). Potential estrogenic activity of the studied silybin congeners was outlined. To address further the stereospecificity of this effect the stereoisomeric forms of silybin were docked into the ligand-binding domain of the human estrogen receptor alpha (ERα) (MOE software, CCG). According to our results both stereoisomers can be accommodated into the ERα active site, but different poses and interactions were observed for silybin A and silybin B.
Comparative Study of Naphthoquinone Contents of Selected Greek Endemic Boraginaceae Plants - Antimicrobial Activities
Authors: Tufa Teisa , Damianakos Harilaos , Graikou Konstantia , Chinou Ioanna
Published: March 2019

The cyclohexane (Ch) extracts of the roots of five Greek endemic Boraginaceae plants, Onosma kaheirei Teppner, O. graeca Boiss., O. erecta Sibth. & Sm., Alkanna sfikasiana Kit Tan, Vold and Strid and Cynoglossum columnae Ten, were investigated for the presence of alkannin/shikonin-related compounds. All species, s except C. columnae and O. erecta, were found to contain this type of compounds. Seven compounds were obtained after several chromatographic separations from the Ch extracts of the investigated plants: deoxyalkannin (1), 2″-( S)- α-methylbutyrylalkannin (2), isobutyrylalkannin (3), propionylalkannin (4), acetylalkannin (5), β-hydroxyisovalerylalkannin (6), and β,β-dimethylacrylalkannin (7). All structures were identified by 1D 1H-/13C- and 2D NMR spectroscopy, assisted also by ESI-MS. The extracts and the isolated compounds exhibiting an interesting antimicrobial profile when evaluated for their antimicrobial activity against six Gram-positive and -negative bacteria and three human pathogenic fungi.
Essential Oil Profile, Phenolic Content and Antioxidant Activity of Geranium kikianum
Authors: Zeljković Sanja Ćavar , Tan Kit , Siljak-Yakovlev Sonja , Maksimović Milka
Published: March 2019

This work presents the first phytochemical investigation of Geranium kikianum Kit Tan & G. Vold (Geraniaceae), a species endemic to the southern Peloponnese, Greece. The essential oil from aerial parts of the plant was isolated by hydrodistillation and its chemical composition characterized by GC-MS. A total of 26 compounds were identified, constituting 98.3% of the oil composition. Oxygenated sesquiterpenes were the main group of constituents (75.4%). The major component of the oil was the sesquiterpene ketone germacrone (45.6%). Eleven alcohols represented the most diverse chemical class in the volatile oil (36.3%), and phytol was the most abundant acyclic diterpene alcohol (11.4%). The volatile compounds and residual water remaining after hydrodistillation were screened for their radical-scavenging activity by the DPPH method. IC 50 values ranged from 0.2±0.03 mg/mL for the undiluted decoction to 69.7±0.5 mg/mL for the essential oil. The significant antioxidant activity of the residual water, comparable with that of the widespread synthetic antioxidant BHT (0.2±0.01 mg/mL), and almost tenfold higher than thymol (1.90 ± 0.04 mg/mL), correlates with a high content of total phenolic compounds (100.2±1.7 mg GAE/g), and flavonoids (11.9±1.2 mg GAE/g).
Integrated Analysis of the Bark Oil from Cinnamosma madagascariensis by GC(RI), GC-MS and NMR. 13C NMR data of Cyclocopacamphene and Cyclosativene
Authors: Garcia Gabriel , Rabehaja Delphin , Charmillon Julie-Marie , Ramanoelina Panja , Casanova Joseph , Tomi Félix
Published: March 2019

The composition of leaf and bark oils of Cinnamosma madagascariensis has been investigated by a combination of GC (RI), GC-MS and 13C NMR. The leaf oil contained mainly monoterpenes: myrcene (17.9%), limonene (17.8%), β-phellandrene (15.3%) and linalool (12.2%). The bark oil, investigated for the first time, contained β-pinene (49.9%) and α-pinene (19.5%) as major components. Special attention was paid to the identification of cyclocopacamphene, an epimer of cyclosativene. 13C NMR data of both compounds have been provided.
Composition, in vitro Cytotoxicity, Anti-mildew and Anti-wood-decay Fungal Activities of the Fruit Essential Oil of Liquidambar formosana from Taiwan
Authors: Su Yu-Chang , Ho Chen-Lung
Published: March 2019

This study investigated the chemical composition, in vitro cytotoxicity, anti-mildew, and anti-wood-decay fungal activities of the essential oil isolated from the fruit of Liquidambar formosana from Taiwan. The essential oil from the fresh fruit was isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC-MS. A total of 45 compounds were identified, representing 98.5% of the essential oil. The main components identified were α-pinene (16.8%), β-caryophyllene (10.1%), τ-muurolol (8.3%), τ-cadinol (7.6%), β-pinene (6.7%), and sabinene (5.7%). The essential oil exhibited cytotoxic activity against human oral, liver, and lung cancer cells. The active source compounds were β-caryophyllene, τ-cadinol, and τ-muurolol. The fruit essential oil was shown to have excellent anti-mildew and anti-wood-decay fungal activities, the active compounds being evaluated as τ-cadinol and τ-muurolol.
Antimicrobial Activity of two Semisynthetic Triterpene Derivatives from Euphorbia Officinarum Latex Against Fungal and Bacterial Phytopathogens
Authors: Smaili Amal , Mazoir Noureddine , Rifai Lalla Aicha , Koussa Tayeb , Makroum Kacem , Benharref Ahmed , Faize Lydia , Alburquerque Nuria , Burgos Lorenzo , Belfaiza Malika , Faize Mohamed
Published: March 2019

This study evaluated the in vitro antimicrobial effect of 3β-acetoxy-norlup-20-one (1) and 3-chloro-4α,14α-dimethyl-5α-cholest-8-ene (2), triterpene derivatives from Euphorbia officinarum latex against fungal and bacterial phytopathogens. Results showed that although mycelial growth of several strains of Verticillium dahlia, and Fusarium oxysporum fsp. melonis and Penicillium expansum was affected only moderately, the two compounds were able to reduce highly conidia formation and germination, suggesting that they act as fungistatic compounds. Their antibacterial activity was tested against Pseudomonas syringae pv. syringae (Pss), P. syringae pv. tabacci (Pst), Erwinia amylovora (Ea) and Agrobacterium tumefaciens (At) using disc diffusion method. Results showed that compound 2 was more effective in inhibiting the growth of Pss, Pst and Ea than compound 1.
Alkaloids of Seeds, in Vitro Cultivated, and ex vitro Adapted Plants of the Bulgarian Endemic Species Papaver Degenii (Papaveraceae)
Authors: Doncheva Tsvetelina , Stanilova Marina , Vutov Vassil , Philipov Stefan
Published: March 2019

Papaver degenii (Urum. & Jav.) Kuzmanov is a Bulgarian endemic and glacial relict growing in the alpine zone of Pirin Mountains and it is included in the Red Data Book of Bulgaria. Numerous plants were in vitro multiplied in order to study the alkaloid composition of the species and to test the potential for green biotechnology establishment. Percentages of the crude alkaloid mixture in dried in vitro shoots and ex vitro adapted plants to room phytotron were similar to that in seeds (0.49%) and 5 to 6 times higher than in the aerial parts of wild-growing plants. Amurensine was the only alkaloid detected in the seeds. Four isoquinoline alkaloids were isolated from the regenerated plants, belonging to two alkaloid types: isopavines (amurensine and O-methylthalisopavine) and protopines (allocryptopine and protopine), amurensine being the main alkaloid: 63.4% in in vitro shoots, up to 88.1% in the aerial parts of ex vitro adapted plants. Allocryptopine was in higher amount (30%) in the roots of the ex vitro adapted plants.
A New Benzophenanthridine Alkaloid from Caloncoba Glauca
Authors: Agbo Jabar B.P.A.A. , Mpetga James D.S. , Bikanga Raphael , Tchuenguem Roland T. , Tsafack Rolande B.N. , Awouafack Maurice D. , Dzoyem Jean P. , Ito Takuya , Morita Hiroyuki , Tane Pierre
Published: March 2019

Three alkaloids including a new one, N-formyldihydrochelerythrine (1), together with four other known compounds were isolated from the stem bark of Caloncoba glauca. The structure of the new compound was elucidated from spectroscopic and mass spectrometric evidence. This is the first report of alkaloids from the genus Caloncoba. Sesamin (4) [MIC = 256 μg/mL ( Candida albicans) and dihydrochelerythrine (2) [MIC = 32 ( C. albicans and C. parapsilosis), and 128 μg/mL ( C. krusei)] had moderate to weak antifungal activity.
Ochroborbone, A New Cytotoxic Indole Alkaloid from Ochrosia Borbonica
Authors: Liu Yan-Ping , Chen A-Hong , Li Ruo-Heng , Yang Hui-Wen , Bao Hai-Nan , Lai Liang , Zong Kang , Fu Yan-Hui
Published: March 2019

A new monoterpenoid indole alkaloid, ochroborbone (1), along with five known alkaloids (2–6), were isolated from the stems and leaves of Ochrosia borbonica. Among them, ochroborbone (1) is a rare C17-nor monoterpenoid indole alkaloid, and the known compounds (2-6) were isolated from Ochrosia for the first time. These structures were established on the basis of extensive spectroscopic methods. All isolated compounds were evaluated for their cytotoxicities against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 in vitro. Compounds 1 and 2 exhibited inhibitory effects with IC50 values comparable with those of cisplatin.
Phenolic Isomers from Plantago Catharinea Leaves: Isolation, Identification, Quantification and in Vitro Antioxidant Activity
Authors: De Souza Mesquita Leonardo Mendes , Da Rocha Claudia Quintino , Affonso Luiz Henrique Lima , Cerulli Antonietta , Piacente Sonia , Tangerina Marcelo Marucci Pereira , Martins Maria Bernadete Gonçalves , Vilegas Wagner
Published: March 2019

In this study we isolated two polyphenolic acids of m/z 639, called catharinol A and catharinol B, from Plantago catharinea L. (Plantaginaceae) leaves. Although presenting very similar structures, catharinol A showed higher antioxidant activity when compared with gallic acid and quercetin standards. These compounds are position isomers and present in their chemical structure the rare sugar D-allose. Molecules with similar constitution are known to have important biological activities such as antitumor and immunosuppressive. These compounds were isolated by high-performance liquid chromatography (HPLC) and characterized by mass spectrometry (FIA-ESI-IT-MS/MS) and nuclear magnetic resonance (NMR). This work is the first study on the chemical composition of P. catharinea and encourages the production of Plantago species as a good source of bioactive molecules.
Spasmolytic Action of Preparations and Compounds from Hofmeisteria schaffneri
Authors: Pérez-Vásquez Araceli , Ángeles-López Guadalupe , Cruz Isabel Rivero , Flores-Bocanegra Laura , Linares Edelmira , Bye Robert , Mata Rachel
Published: March 2019

Hofmeisteria schaffneri is used in Mexican folk medicine for treating painful gastric complaints. Therefore, in this paper the smooth muscle relaxant effect of the essential oil, and an infusion of the whole plant were evaluated using the gastrointestinal transit test in mice. The results revealed that both preparations at 316 mg/kg inhibited gastrointestinal transit by 47.5 and 52.1%, respectively. The common component of the infusion and essential oil was 8,9-epoxy-10-acetoxythymol angelate (2), which inhibited the gastrointestinal transit by 53.4% at a dose of 31.6 mg/kg. An HPLC-UV method was developed and validated to quantify 2. The chromatographic conditions were: A LiChrospher® 100 RP-18 column (250 × 4 mm i.d., 5 μm) with a mobile phase composed of CH3CN-H2O, in a gradient run at a flow rate of 0.6 mL/min, using a wavelength of 215 nm. The method was linear, precise, accurate, and showed excellent recovery. According to the results, compound 2 can be used as a marker for the quality control procedures of the crude drug of H. schaffneri.
A New Ajmaline-type Alkaloid from the Roots of Rauvolfia serpentina
Authors: Rukachaisirikul Thitima , Chokchaisiri Suwadee , Suebsakwong Parichat , Suksamrarn Apichart , Tocharus Chainarong
Published: March 2019

A new ajmaline-type alkaloid, 21- O-methylisoajmaline (1), together with twenty-one known compounds, a mixture ofβ-sitosterol (2) and stigmasterol (3), reserpinine (4), tetrahydroalstonine (5), reserpine (6), venoterpine (7), yohimbine (8), 6'- O-(3,4,5-trimethoxybenzoyl)glomeratose A (9), isoajmaline (10), 3- epi-α-yohimbine (11), methyl 3,4,5-trimethoxy- trans-cinnamate (12), a mixture of β-sitosterol 3- O-β-D-glucopyranoside (13) and stigmasterol 3- O-β-D-glucopyranoside (14), rescidine (15), 7-deoxyloganic acid (16), ajmaline (17), suaveoline (18), (+)-tetraphyllicine (19), loganic acid (20), 3-hydroxysarpagine (21), and sarpagine (22), were isolated from the roots of Rauvolfia serpentina. Their structures were elucidated by spectroscopic data analysis and comparison with literature data. Compounds 11, 12 and 15 were for the first time identified from the genus Rauvolfia and 5, 7, 11, 12, 15, 18 and 22 were found from R. serpentina for the first time. Compound 11 showed moderate anticholinesterase activity with IC50 value of 15.58 μM, whereas 6 exhibited strong vasorelaxant activity with the EC50 value of 0.05 μM.
Constituents of Flourensia blakeana (Asteraceae)
Authors: Arjona Mila , Alarcón Alejandro A. , Pacciaroni Adriana , Alarcón Rosana
Published: March 2019

Chemical study of the aerial parts of Flourensia blakeana Dillon allowed the isolation and identification of two novel compounds, 3, 5, 5'-trihydroxy-7, 3'-dimethoxyflavanone (1), and 2α-angeloyloxycostic acid (2) together with several known compounds. The structures were elucidated using spectroscopic data from 1D, 2D NMR and HRDEIMS experiments.