bluuebunny/crossref_metadata_2025 huggingface dataset:
Preferentially Cytotoxic Constituents of Andrographis paniculata and their Preferential Cytotoxicity against Human Pancreatic Cancer Cell Lines
Authors: Lee Sullim , Morita Hiroyuki , Tezuka Yasuhiro
Published: March 2019

In the course of our search for anticancer agents based on a novel anti-austerity strategy, we found that the 70% EtOH extract of the crude drug Andrographis Herba (aerial parts of Andrographis paniculata), used in Japanese Kampo medicines, killed PANC-1 human pancreatic cancer cells preferentially in nutrient-deprived medium (NDM). Phytochemical investigation of the 70% EtOH extract led to the isolation of 21 known compounds consisting of six labdane-type diterpenes (11, 15, 17-19, 21), six flavones (5, 7, 10, 12, 14, 20), three flavanones (2, 6, 16), two sterols (3, 8), a fatty acid (1), a phthalate (4), a triterpene (9), and a monoterpene (13). Among them, 14-deoxy-11,12-didehydroandrographolide (17) displayed the most potent preferential cytotoxicity against PANC-1 and PSN-1 cells with PC50 values of 10.0 μM and 9.27 μM, respectively. Microscopical observation, double staining with ethidium bromide (EB) and acridine orange (AO), and flow cytometry with propidium iodide/annexin V double staining indicated that 14-deoxy-11,12-didehydroandrographolide (17) triggered apoptosis-like cell death in NDM with an amino acids and/or serum-sensitive mode.
The Assignment of the Absolute Configuration of C-22 Chiral Center in the Aglycones of Triterpene Glycosides from the Sea Cucumber Cladolabes schmeltzii and Chemical Transformations of Cladoloside C
Authors: Kalinovsky Anatoly I. , Silchenko Alexandra S. , Avilov Sergey A. , Kalinin Vladimir I.
Published: March 2019

The absolute R-configuration of the C-22 chiral center in cladoloside C (1) and therefore in all related glycosides isolated from the sea cucumber Cladolabes schmeltzii has been assigned by Mosher‘s method. Some chemical transformations of the native glycoside 1 were carried out to apply this method. This resulted in the isolation and elucidation of chemical structures of progenin 2 and artefact aglycones 3 and 4, obtained from 1 and assignment of the absolute R-configuration of C-22 in the progenin 2. The coincidence of C-22 configurations in the studied compounds with those of the earlier known lanostane-type aglycone of frondoside C and holostane-type aglycone of cladoloside C (1) confirms the generic biosynthetic pathways to different types of sea cucumber glycoside aglycones. It suggests the same R-configuration of C-22 chiral centers in all the sea cucumber glycosides having C-22 functionalities.
New Derivatives of Natural Acyclic Guanidine Alkaloids with TRPV Receptor-Regulating Properties
Authors: Ogurtsova Ekaterina K. , Makarieva Tatyana N. , Korolkova Yuliya V. , Andreev Yaroslav A. , Mosharova Irina V. , Denisenko Vladimir A. , Dmitrenok Pavel S. , Lee Yeon-Ju , Grishin Eugene V. , Stonik Valentin A.
Published: March 2019

The guanidine alkaloids, dihydropulchranin A (2), prepared from pulchranin A from the sponge Monanchora pulchra, and hexadecylguanidine (3), a synthetic analog of pulchranins, were studied for their TRPV channel-regulating activities. Compound 2 was active as an inhibitor of rTRPV1 and hTRPV3 receptors with EC50 values of 24.3 and 59.1 μM, respectively. Hexadecylguanidine (3) was not active against these receptors.
Pyrrolizidine Alkaloids in Adenostyles alliariae and A. glabra from the Austrian Alps
Authors: Chizzola Remigius
Published: March 2019

The alkaloid content of Adenostyles alliariae and A. glabra (Asteraceae) has been evaluated. Both species contain toxic macrocyclic unsaturated pyrrolizidine alkaloids with seneciphylline as the main compound accounting for more than 90% of the alkaloid fraction in all above ground plant parts. Further alkaloids were spartioidine, acetyl-senciphylline and senecionine. Inflorescences showed the highest alkaloid contents with 21.1 and 13.4 mg/g in A. alliariae and A. glabra, respectively. Stems and leaves had 2–3 times lower contents. Therefore, these Adenostyles species must be considered as highly toxic plants.
6-Methoxyflavonoids and Other Constituents from Microliabum polymnioides (Asteraceae)
Authors: Díaz Oscar , Alarcón Rosana , Gutiérrez Diego , Pacciaroni Adriana , Cayo Fany , Sosa Virginia
Published: March 2019

The flower heads of Microliabum polymnioides afforded scopoletin, 5,4′-dihydroxy-3,6,7-trimethoxyflavone, 3,5,4′-trihydroxy-6,7-dimethoxyflavone and 3,5,7,4′-tetrahydroxy-6-methoxyflavone. The leaves contained hexadecanoic acid, phytol and docosane. This is the first report on the presence of 6-methoxy-flavonoids in Microliabum genus.
Phytochemical and Antimicrobial Screening of Flavanones and Chalcones from Galenia africana and Dicerothamnus rhinocerotis
Authors: Ticha Lawrence A. , Klaasen Jeremy A. , Green Ivan R. , Naidoo Sivapregasen , Baker Bienyameen , Pietersen Ray-Dean
Published: March 2019

This study focused on an 80% ethanol:water extract of Galenia africana and Dicerothamnus rhinocerotis in which a phytochemical study revealed the presence of flavonoids as the major secondary plant metabolites. Eleven pure flavonoids viz., ( E)-2′,4′-dihydroxychalcone 1, ( S)-7-hydroxyflavanone 2, ( E)-2′,4′-dihydroxy-2,3-dihydrochalcone 3, ( S)-5,7-dihydroxyflavanone 4, ( S)-2′,5,7,-trihydroxyflavanone 5, ( S)-5,7-dihydroxy-2′-methoxyflavanone 6, 5,7-dihydroxy-4H-chromen-4-one 7, ( S)-5-hydroxy-7-methoxyflavanone 8 and ( E)-2-hydroxy-3′,6′-dimethoxychalcone 9 were isolated from G. africana, while [sakuranetin] ( S)-4′,5-dihydroxy-7-methoxyflavanone 10 and [eriodictyol-3′,7-dimethyl ether] ( S)-4′,5-dihydroxy-3′,7-dimethoxyflavanone 11 were isolated from D. rhinocerotis. Compounds 6 and 9 are new while this is the first reported isolation of 1, 2, 3, 4, 5, 7, 8, 10 and 11 from these plants. All isolated compounds were tested for their antimycobacterial activity against the reference strain Mtb H37Rv. The most active compound, 9, demonstrated a MIC 99 of 5 μM against Mtb H37Rv American Type Culture (ATCC) and (ATCC27294), which were also sensitive to Isoniazid (INH) and Rifampicin. The antibacterial activity of 9 might be ascribed to the presence of features such as the α,β-unsaturated ketone and the substitution patterns on the A and B rings.
Chemical Constituents of Pyrrosia calvata
Authors: Chen Yu-Jie , Xie Guo-Yong , Xu Guang-Kai , Dai Yi-Qun , Shi Lu , Qin Min-Jian
Published: March 2019

A novel flavanone glycoside, 3′,5′,5,7-tetrahydroxy-6- C- β-D-glucopyranosyl-flavanone (1), along with 16 known compounds, ( R/ S)-eriodictyol-8- C- β-D-glucopyranoside (2), quercetin-3- O- α-D-rhamnosyl (1′”→3′”)- β-D-glucopyranoside (3), hemipholin (4), 4 β-carboxymethyl-(-)-epicatechin methyl ester (5), kaempferol (6), quercetin (7), mangiferin (8), chlorogenic acid (9), 1,5- O-dicaffeoylquinic acid (10), 3,5- O-dicaffeoylquinic acid (11), 3- O-caffeoylquinic acid methyl ester (12), 1- O-caffeoyl glycoside (13), 4- O- β-D-glucopyranosyl-caffeic acid (14), 3′- O-methyleplcatechin-7- O- β-D-glucopyranoside (15), hop-22(29)-en-30-ol (16) and diploptene (17), were isolated from the whole plant of Pyrrosia calvata (Backer) Ching. Among them, compounds 2, 3, 4, 10, 11, 13 and 14 were isolated from the family Polypodiaceae for the first time, and compound 5 has not been recorded previously from the genus Pyrrosia.
In vitro Toxicity and in vivo Immunomodulatory Effects of Flavokawain A and Flavokawain B in Balb/C Mice
Authors: Abu Nadiah , Mohamed Nurul Elyani , Tangarajoo Nirosha , Yeap Swee Keong , Akhtar M Nadeem , Abdullah Mohd Puad , Omar Abdul Rahman , Alitheen Noorjahan Banu
Published: March 2019

Flavokawains are chalcones that can be found in the root extracts of the kava-kava ( Piper methysticum) plant. Flavokawain A and flavokawain B are known to possess potential anti-inflammation and anti-cancer activities. Nevertheless, the effects of both these compounds on the normal function of the host have not been studied. There is a need to find agents that can enhance the functionality of the immune system without disturbing the homeostatic balance. This study aimed to determine the toxicity and immunomodulatory effects of flavokawain A and flavokawain B on Balb/c mice. Several assays were conducted, the MTT viability assay, cytokine detection (IL-2 and TNF-α), immunophenotyping of important immune markers, serum biochemical analysis and detection of nitric oxide levels. Based on our results, flavokawain A and B did not cause mortality and all mice were observed normal after the treatment period. Both flavokawains stimulated splenocyte proliferation, the secretion of IL-2 and TNF-α and raised the population of T cell subsets without significantly altering the level of several serum biochemical parameters. Overall, flavokawain A and B could serve as potential immune-modulator drugs without causing any toxicity, however further in vivo evidence is needed.
Antileishmanial Activity of Compounds Isolated from Sassafras albidum
Authors: Pulivarthi Divya , Steinberg Kelly Marie , Monzote Lianet , Piñón Abel , Setzer William N.
Published: March 2019

Leishmaniasis is a neglected tropical disease caused by Leishmania parasitic protozoa, which currently lacks efficient treatment. Natural products have shown promise as a potential source for antiprotozoal drugs. This work focuses on the antileishmanial potential of Sassafras albidum (Lauraceae) bark extract. The crude bark extract of S. albidum showed excellent antileishmanial activity with an IC50 value less than 12.5 μg/mL against promastigotes of L. amazonensis. The chloroform stem bark extract of S. albidum was subjected to preparative column chromatography. Five compounds were isolated, purified by recrystallization, and identified as sesamin, spinescin, β-sitosterol, hexatriacontanal, and 1-triacontanol. Antileishmanial and cytotoxic screening were performed on these compounds. Sesamin exhibited the best activity against L. amazonensis with an IC50 of 15.8 μg/mL and was not cytotoxic to mouse macrophage cells ( CC50 > 100 μg/mL).
Determination of the Juglone Content of Juglans regia Leaves by GC/MS
Authors: Matławska Irena , Bylka Wiesława , Widy-Tyszkiewicz Ewa , Stanisz Beata
Published: March 2019

The constituents of walnut (Juglans regia L.) leaves are represented by tannins, phenolics, and naphthoquinones, the characteristic compound being juglone. The content of juglone in the methanolic extract of the leaves determined by the GC/MS method was 9.9±0.2 mg/100 g; small amounts (1.3±0.02 mg/100 g) were recorded in the infusion, whereas in the decoction it was not detected. As some studies indicate toxicity of juglone, only decoctions should be recommended for therapeutic use.
Synthesis, Cytotoxic and Contraceptive Activity of 6,8,9-Trihydroxy-2-methyl-2H-naphtho[2,3-b]pyran-5,10-dione, a Pigment of Echinothrix diadema, and its Analogs
Authors: Pokhilo Natalia D. , Melman Galina I. , Kiseleva Marina I. , Denisenko Vladimir A. , Anufriev Victor Ph.
Published: March 2019

6,8,9-Trihydroxy-2-methyl-2 H-naphtho[2,3- b]pyran-5,10-dion, a pigment of the sea urchin Echinothrix diadema, and six analogs were synthesized. The cytotoxic activity and contraceptive properties of the synthesized pyranonaphthazarins have been investigated using the sperm and eggs of the sea urchin Strongylocentrotus intermedius.
A New Phenyl Ethyl Glycoside from the Twigs of Acer tegmentosum
Authors: Park SeonJu , Lee Hwa Young , Nhiem Nguyen Xuan , Lee Taek Hwan , Kim Nanyoung , Cho Seung Hun , Kim Seung Hyun
Published: March 2019

One new phenyl ethyl glycoside, 2-(4-hydroxyphenyl)ethyl- O-α-L-arabinofuranosyl-(1→6)- O-β-D-glucopyranoside (1) and 11 known compounds (2-12) were isolated from the twigs of Acer tegmentum. Compound 6 showed potent anti-neuroinflammatory activity against the LPS-stimulated BV-2 microglial cells with tNO production of 25.0±2.5 μM and TNF-α concentration of 617.6±47.1 pg/mL at 30 μM.
Synthesis of Stilbene Derivatives: A Comparative Study of their Antioxidant Activities
Authors: Romero Miguel A. , González-Delgado José A. , Arteaga Jesús F.
Published: March 2019

A series of structurally simple compounds belonging to thestilbene family were synthesized by means of a Ti(III)-mediated methodology that allows access, in an efficient manner, to derivatives of dihydrostilbene, E-stilbene, and stilbene oxide, with high yields. The antioxidant activity of these compounds has been evaluated by means of two electrochemical assays, which provide complementary information, showing that the majority of these stilbene analogs exhibit significant antioxidant activity dependent on the electronic structure and functionalization of the molecule in each case.
Soluble Phenolic Compounds in Different Cultivars of Red Clover and Alfalfa, and their Implication for Protection against Proteolysis and Ammonia Production in Ruminants
Authors: Kagan Isabelle A. , Goff Ben M. , Flythe Michael D.
Published: March 2019

Red clover ( Trifolium pratense) contains soluble phenolic compounds with roles in inhibiting proteolysis and ammonia production. Alfalfa ( Medicago sativa) has been found to have a low phenolic content, but few alfalfa and red clover cultivars have been compared for phenolic content. Total soluble phenolics were quantified by a Folin-Ciocalteu colorimetric assay in nine red clover and 27 alfalfa cultivars. Mean total phenolic contents of red clover and alfalfa were 36.5 ± 4.3 mg/gdw and 15.8 ± 1.4 mg/gdw, respectively, with the greater standard deviation of red clover possibly indicating more diversity in phenolic content. Because different phenolic standards had different response factors in the colorimetric assay, the red clover and 11 alfalfa cultivars were analyzed by HPLC to determine if the differences in total soluble phenolics between genera reflected differences in the amounts of phenolics or in the classes of phenolics responding to the colorimetric assay. Two red clover cultivars differed in total phenolics and phaselic acid. Alfalfa produced different phenolic compounds from red clover, at lower concentrations. Extracts of two red clover cultivars were separated by thin-layer chromatography (TLC), and the bands were assayed for activity against Clostridium sticklandii, a bovine ruminal hyper ammonia-producing bacterium (HAB). Only biochanin A had anti-HAB activity. Inhibitory amounts indicated that five red clover cultivars could be suitable sources of anti-HAB activity.
Bergenin Content and Free Radical Scavenging Activity of Bergenia Extracts
Authors: Hendrychová Helena , Martin Jan , Tůmová Lenka , Kočevar-Glavač Nina
Published: March 2019

Our research was focused on the evaluation of bergenin content and free radical scavenging activity of extracts prepared from three different species of Bergenia - B. crassifolia (L.) Fritsch., B. ciliata (Haw.) Sternb. and B. x ornata Stein. collected during different seasons. Using an HPLC method, the highest total amount of bergenin was revealed in the leaves of B. x ornata and B. crassifolia (4.9 - 5.1 mg.g−1). Free radical scavenging power was determined by two methods - FRAP and NADH. The best free radical scavengers were B. crassifolia (FRAP: 6.7 - 15.9 mg GAE.100g−1; NADH: 20.3 - 50.9%) and B. ornata (FRAP: 13.7 - 15.2 mg GAE.100g−1; NADH: 29.3 - 31.1%). The lowest content of bergenin and the weakest radical scavenger was B. ciliata (bergenin: 3.1 mg.g−1; FRAP: 5.5 - 11.0 mg GAE.100g−1; NADH: 23.2 - 25.6%). The presence of a large percentage of bergenin is responsible for the radical scavenging activity, as shown by the results from the FRAP and NADH assays. Significant, positive correlation was found between bergenin content and radical scavenging activity in both methods.
Biotransformation of (-)-(10E,15S)-10,11-Dehydrocurvularin
Authors: Deng Zhangshuang , Deng Aiping , Luo Dan , Gong Dachun , Zou Kun , Peng Yan , Guo Zhiyong
Published: March 2019

(-)-(10 E,15 S)-10,11-Dehydrocurvularin (1), produced from an associated-fungus of Scolopendra subspinipes mutilans on a gram scale, was microbiologically converted to curvularin (2) and 5-methoxycurvularin (3) by Antrodiella semisupina in 61% totally isolated yield. The structures of these compounds were elucidated on the basis of spectroscopic and mass spectrometric analysis. The undescribed assignments of 1H and 13C NMR spectral data for 5-methoxycurvularin (2) has now been explicitly provided. The cytotoxic activities of compounds 1-3 against four human cancer cell lines were evaluated. Dehydrocurvularin (1) showed moderate cytotoxicity against Caski and Hep-G2, and curvularin (2) was selectively cytotoxic against MDA-MB-231.
Screening of Microbial Extracts for Anticancer Compounds Using Streptomyces Kinase Inhibitor Assay
Authors: Shanbhag Prashant , Bhave Sarita , Vartak Ashwini , Kulkarni-Almeida Asha , Mahajan Girish , Villanueva Ivan , Davies Julian
Published: March 2019

Eukaryotic kinases are known to play an important role in signal transduction pathways by phosphorylating their respective substrates. Abnormal phosphorylations by these kinases have resulted in diseases. Hence inhibitors of kinases are of considerable pharmaceutical interest for a wide variety of disease targets, especially cancers. A number of reports have been published which indicate that eukaryotic-like kinases may complement two-component kinase systems in several bacteria. In Streptomyces sp. such kinases have been found to have a role in formation of aerial hyphae, spores, pigmentation & even in antibiotic production in some strains. Eukaryotic kinase inhibitors are seen to inhibit formation of aerial mycelia in Streptomyces without inhibiting vegetative mycelia. This property has been used to design an assay to screen for eukaryotic kinase inhibitors. The assay involves testing of compounds against Streptomyces 85E ATCC 55824 using agar well diffusion method. Inhibitors of kinases give rise to “bald” colonies where aerial mycelia and sporulation inhibition is seen. The assay has been standardized using known eukaryotic protein kinase inhibiting anticancer agents like AG-490, AG-1295, AG-1478, Flavopiridol and Imatinib as positive controls, at a concentration ranging from 10 μg/well to 100 μg/well. Anti-infective compounds which are not reported to inhibit eukaryotic protein kinases were used as negative controls. A number of microbial cultures have been screened for novel eukaryotic protein kinase inhibitors. Further these microbial extracts were tested in various cancer cell lines like Panc1, HCT116, Calu1, ACHN and H460 at a concentration of 10 μg/mL/ well. The anticancer data was seen correlating well with the Streptomyces kinase assay thus validating the assay.
Composition, in vitro Cytotoxic, and Antimicrobial Activities of the Flower Essential Oil of Diospyros discolor from Taiwan
Authors: Su Yu-Chang , Hsu Kuan-Ping , Wang Eugene I-Chen , Ho Chen-Lung
Published: March 2019

This study investigated the chemical composition, in vitro cytotoxic, and antimicrobial activities of the essential oil isolated from the flower of Diospyros discolor from Taiwan. The essential oil was isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC-MS. Twenty-eight compounds were identified, representing 100% of the oil. The main components identified were (2 Z,6 E)-farnesol (35.0%), α-cadinol (10.9%), ( E)-nerolidol (6.9%), α-humulene (6.0%), τ-cadinol (5.6%), β-caryophyllene (5.3%), and τ-muurolol (5.3%). The oil exhibited cytotoxic activity against human colon, liver, and lung cancer cells. The active compounds were β-caryophyllene, α-humulene, τ-cadinol, τ-muurolol, α-cadinol, and (2 Z,6 E)-farnesol. The antimicrobial activity of the oil was tested by the disc diffusion and micro-broth dilution methods against ten microbial species. The oil exhibited moderate to strong growth suppression against Bacillus cereus, Staphylococcus aureus, S. epidermidis, Escherichia coli, Enterobacter aerogenes, and Candida albicans, with inhibition zones of 40 to 52 mm and MIC values of 31.25–62.5 μg/mL, respectively. For the antimicrobial activities of the oil, the active compounds were determined to be α-cadinol, τ-cadinol, τ-muurolol and (2 Z,6 E)-farnesol.
Volatile Constituents of the Leaves of Aniba hostmanniana (Lauraceae) and their Antibacterial Activities
Authors: Lima Wilberto De , Rojas-Fermín Luis B. , Koteich-Khatib Sonia , Lucena María Eugenia , Arzola Juan Carmona
Published: March 2019

The essential oil of Aniba hostmanniana (Nees) Mez, family Lauraceae, was obtained from fresh leaves by hydrodistillation. The chemical composition of the oil was assessed using gas chromatography with mass spectrometric detection (GC-MS). The antimicrobial activity of the essential oil was tested against Gram-negative bacteria ( Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia) and the Gram-positive bacterium Staphylococcus aureus. GC-MS analysis revealed the presence of 35 compounds in the essential oil, the predominant ones being benzyl benzoate (29.3%), δ-cadinene (12%), β-caryophyllene (10.5%), bicyclogermacrene (5.9%), and α-copaene (3.9%). The oil showed activity against most of the bacterial strains studied.
Eriosema (Fabaceae) Species Represent a Rich Source of Flavonoids with Interesting Pharmacological Activities
Authors: Awouafack Maurice Ducret , Tane Pierre , Spiteller Michael , Eloff Jacobus Nicolaas
Published: March 2019

Many flavonoids have so far been isolated as main secondary metabolites in plant species of the genus Eriosema (Fabaceae), which contains approximately 160 species. A total of 52 flavonoids including isoflavones, dihydroflavonols, flavonols, flavanones, dihydrochalcones, isoflavanone and their pyrano or glucoside derivatives were isolated and characterized from the five species of this genus investigated to date. Total synthesis and semi-synthesis (acetylation, methylation, hydrogenation, and cyclization) of some isolated flavonoids were reported. Due to several significant pharmacological properties (antimicrobial, cytotoxicity, anti-mycobacterial, antioxidant, antiviral, erectile-dysfunction, vasodilatory and hypoglycemic) of the isolated flavonoids and derivatives, more scientists should be interested in investigating Eriosema species. The present review is the first to document all flavonoids that have been reported from the genus Eriosema to date together with their synthetic and semi-synthetic derivatives, and their pharmacological properties. Dihydrochalcones, which are precursors of other classes of flavonoids, are very rare in natural sources and their isolation from Eriosema species may explain the large number of flavonoids found in this genus. It appears that isoflavone could be a marker for species in this genus. The 83 flavonoids (1–83) documented include 52 isolates, 31 semi-synthetic and 3 totally synthetic derivatives. Data were obtained from Google scholar, Pubmed, Scifinder, Sciencedirect, and Scopus. With 52 different flavonoids isolated from only 5 of the approximately 160 species it shows the remarkable chemical diversity of this genus. This compilation of the biological activities and chemical composition may renew the interest of pharmacologists and phytochemists in this genus.
Stereoselective Synthesis of 2,15-Dihydroxycalamenene and 2-Methoxycalamenene. Determination of the Configuration of Natural 2,15-Dihydroxycalamenene
Authors: Serra Stefano
Published: March 2019

The enantioselective preparation of the two diastereoisomeric forms of 2,15-dihydroxycalamele‘ne and 2-methoxycalamenene is here described. The (7 S,10 R) and (7 R,10 R) isomers of these natural products were synthesized starting from (5 R,8 S)-methyl-4-hydroxy-8-isopropyl-5-methyl-5,6,7,8-tetrahydronaphthalene-2-carboxylate and (5 R,8 R)-methyl-4-hydroxy-8-isopropyl-5-methyl-5,6,7,8-tetrahydronaphthalene-2-carboxylate, respectively, in turn preparable from (-)-menthone and (+)-isomenthone. The NMR analysis of the obtained sesquiterpenes allow assigning (7 R,10 S) absolute configuration to the natural occurring 2,15-dihydroxycalamelene.
Sesquiterpenes from the Vietnamese Marine Sponge Dysidea Fragilis
Authors: Cuc Nguyen Thi , Anh Hoang Le Tuan , Hang Dan Thi Thuy , Nhiem Nguyen Xuan , Dang Nguyen Hai , Nam Nguyen Hoai , Yen Pham Hai , Thung Do Cong , Thu Vu Kim , Van Minh Chau , Van Kiem Phan
Published: March 2019

Two new sesquiterpenes, named dysinidins A-B (3, 4) along with two known sesquiterpenes, furodysinin lactone (1) and O-methyl furodysinin lactone (2), were isolated from the Vietnamese marine sponge Dysidea fragilis. Their structures were determined by 1D- and 2D-NMR spectroscopies and HR ESI MS, as well as by comparison with reported literature data. None of compounds showed inhibitory growth of human lung cancer cell lines, A-549 and H-1975 (IC50 > 30μM).
Vibrational Circular Dichroism Absolute Configuration of 9,12-Cyclomulin-13-ol, a Diterpene from Azorella and Laretia Species
Authors: Muñoz Marcelo A. , San-Martín Aurelio , Joseph-Nathan Pedro
Published: March 2019

The absolute configuration of the diterpenoid 9,12-cyclomulin-13-ol (1), a constituent of Azorella and Laretia species, has been established by vibrational circular dichroism spectroscopy in combination with density functional theory calculations. The obtained normal diterpene absolute configuration confirms that of azorellanol (2), which was determined by single crystal X-ray diffraction.
Ultrafine Betulin Formulation with Biocompatible Carriers Exhibiting Improved Dissolution Rate
Authors: Myz Svetlana A. , Shakhtshneider Tatyana P. , Mikhailenko Mikhail A. , Ogienko Andrey G. , Bogdanova Ekaterina G. , Ogienko Anna A. , Kuznetsova Svetlana A. , Boldyreva Elena V. , Boldyrev Vladimir V.
Published: March 2019

The purpose of this research was to develop new methods of increasing dissolution rate and solubility of betulin extracted from birch bark. The ultrafine formulation of betulin with polyethylene glycol and β-glycine was obtained by freeze-drying. The rate of release of betulin from the formulation into water was significantly higher in comparison with the initial betulin sample and its composite with polyethylene glycol obtained by ball-milling.
Bio-assay Guided Isolation of Anti-cancer Compounds from Anthocephalus Cadamba Bark
Authors: Kumar Deepak , Tejaswi Chilukuri , Rasamalla Saiprasanna , Mallick Sumana , Pal Bikas C
Published: March 2019

Anthocephalus cadamba, an important plant in the traditional system of medicine in India, is reported to possess anticancer activity. Guided by bio-assay tests using human colorectal (HCT116) and hepatocellular carcinoma (HepG2) cell lines, it has been shown to contain three active constituents, the triterpenoid saponins 3- O-[α-L-rhamnopyranosyl]-quinovic acid (1) and 3- O-[α-L-rhamnopyranosyl]-quinovic acid 28- O-[β-D-glucopyranosyl] ester (2), and the alkaloid cadambine (3). The structures of the isolated compounds were established using spectroscopic techniques. The isolated compounds demonstrated concentration dependent inhibition of both the cell lines, where compound 3 proved to be the most potent inhibitor of cell line HCT116 (IC50 45 ± 4 μg/mL) and compound 2 demonstrated maximum inhibitory activity against HepG2 cell line with an IC50 value of 89 ± 7 μg/mL.
(-)-Pentylsedinine, a New Alkaloid from the Leaves of Lobelia Tupa with Agonist Activity at Nicotinic Acetylcholine Receptor
Authors: Paz Cristian , Becerra José , Silva Mario , Burgos Viviana , Heydenreich Matthias , Schmidt Bernd , Tran Thu , Vetter Irina
Published: March 2019

Lobelia tupa, also called devil's tobacco, is a native plant from the center-south of Chile which has been used by the native people of Chile as a hallucinogenic and anesthetic plant. A new piperidine alkaloid, called pentylsedinine, which comprises five carbons in the side chain, was isolated from the aerial part of L. tupa, along with lobeline and lobelanidine. The structure was established on the basis of 1D and 2D NMR spectroscopy. While lobeline is a neutral antagonist at α3β2/α3β4 nAChR and α7 nAChR, both lobelanidine and pentylsedinine act as partial agonists at nAChR.
Furoquinoline Alkaloids from the Leaves of Evodia Lepta as Potential Cholinesterase Inhibitors and their Molecular Docking
Authors: Sichaem Jirapast , Rojpitikul Thanawan , Sawasdee Pattara , Lugsanangarm Kiattisak , Tip-Pyang Santi
Published: March 2019

Nine furoquinoline alkaloids (1–9) were isolated from the leaves of Evodia lepta based on bioassay-guided fractionation and chromatographic techniques. All isolates were evaluated for their cholinesterase (ChEs) inhibitory activities, in which kokusaginine (7) and melineurine (5) exhibited the highest activity toward AChE and BChE, respectively. Lineweaver- Burk plots indicated that 5 and 7 were mixed mode inhibitors of both ChE enzymes. Molecular docking studies on the binding sites of AChE and BChE were performed in order to afford a molecular insight into the mode of action of these active compounds. From this study these compounds have emerged as promising molecules for Alzheimer's disease therapy.
HPLC Plasma Assay of a Novel Anti-MRSA Compound, Kaempferol-3-O-Alpha-L-(2″,3″-di-p-coumaroyl)rhamnoside, from Sycamore Leaves
Authors: Zhang Yiguan , Valeriote Frederick , Swartz Kenneth , Chen Ben , Hamann Mark T. , Rodenburg Douglas L. , McChesney James D. , Shaw Jiajiu
Published: March 2019

Methicillin-resistant Staphylococcus aureus (MRSA) is a serious pathogen that is resistant to current antibiotic therapy. Thus, there is an urgent need for novel antimicrobial agents that can effectively combat these new strains of drug-resistant “superbugs”. Recently, fractionation of an extract from Platanus occidentalis (American sycamore) leaves produced an active kaempferol molecule, 3- O-alpha-L-(2″,3″-di- p-coumaroyl)rhamnoside (KCR), in four isomeric forms; all four isomers exhibit potent anti-MRSA activity. In order to further the preclinical development of KCR as a new antibiotic class, we developed and validated a simple analytical method for assaying KCR plasma concentration. Because KCR will be developed as a new drug, although comprising four stereoisomers, the analytical method was devised to assay the total amount of all four isomers. In the present work, both a plasma processing procedure and an HPLC method have been developed and validated. Mouse plasma containing KCR was first treated with ethanol and then centrifuged. The supernatant was dried, suspended in ethanol, centrifuged, and the supernatant was injected into an HPLC system comprising a Waters C18, a mobile phase composing methanol, acetonitrile, and trifluoroacetic acid and monitored at 313 nm. The method was validated by parameters including a good linear correlation, a limit of quantification of 0.27 μg/mL, and high accuracy. In summary, this method allows a rapid analysis of KCR in the plasma samples for pharmacokinetics studies.
Prenylhydroquinone-Derived Secondary Metabolites from Cultures of the Basidiomycete Lentinus Similis BCC 52578
Authors: Isaka Masahiko , Palasarn Somporn , Sappan Malipan , Srichomthong Kitlada , Karunarathna Samantha C. , Hyde Kevin D.
Published: March 2019

Two new prenylhydroquinone-derived compounds, lentinospirol (1) and 1-(2,5-dihydroxyphenyl)-4-hydroxy-3-methyl-1-butanone (2), were isolated from cultures of the basidiomycete Lentinus similis BCC 52578, together with the known compounds panepoxydone (3), panepoxydione (4), isopanepoxydone (5), 2,2-dimethyl-6-hydroxy-2 H-chromene (6), and (3 R,4 S)-3,4-dihydroxy-2,2-dimethyl-6-methoxychroman (7). Compounds 3 and 4 exhibited cytotoxicity against all cell-lines tested, while the other compounds were inactive.
In Vitro Safety/Protection Assessment of Resveratrol and Pterostilbene in a Human Hepatoma Cell Line (HepG2)
Authors: Lombardi Germana , Vannini Samuele , Blasi Francesca , Marcotullio Maria Carla , Dominici Luca , Villarini Milena , Cossignani Lina , Moretti Massimo
Published: March 2019

The aim of this work was to evaluate in vitro the genotoxic and/or antigenotoxic effects of resveratrol (RESV) and pterostilbene (PTER) on HepG2 cells. Moreover, additional tests were performed to evaluate early and late apoptosis events induced by the tested stilbenes. RESV and PTER did not show any genotoxic activity. As regards antigenotoxicity testing, RESV and PTER showed a typical, U-shaped hormetic dose-response relationship characterized by a biphasic trend with small quantities having opposite effects to large ones. HepG2 cells treated with PTER exhibited a marked increase in early apoptosis (40.1 %) at 250 μM; whereas, the highest concentration tested for both RESV and PTER significantly increased the proportion of HepG2 cells undergoing late apoptosis (32.5 and 51.2 %, respectively). The observed pro-apoptotic activity could, at least in part, explain the hormetic response observed when the compounds were tested for antigenotoxicity ( i.e., in the presence of induced DNA damage).
Red Maple (Acer Rubrum) Aerial Parts as a Source of Bioactive Phenolics
Authors: Zhang Yan , Ma Hang , Yuan Tao , Seeram Navindra P.
Published: March 2019

The bark and stems of red maple ( Acer rubrum) are reported to contain bioactive phenolics but its aerial parts, namely, flowers and leaves, remain largely unexplored. This is unfortunate considering that various parts of the red maple were used for traditional medicinal purposes by the indigenous peoples of eastern North America, where this species is found. Herein, we report the identification of twenty-five (1–25) phenolics, including two new galloyl derivatives (1 and 2), from red maple flowers and leaves. Of these, ten compounds (1–10), including the new compounds, were isolated and identified by NMR and HRESIMS data while the remaining fifteen compounds (11–25) were identified by HPLC-DAD analyses (by comparison with chemical standards). The isolates (1–10), along with the clinical drug, acarbose, were evaluated for their α-glucosidase enzyme inhibitory activities.
Biocompounds Attenuating the Development of Obesity and Insulin Resistance Produced by a High-fat Sucrose Diet
Authors: Etxeberria Usune , De La Garza Ana Laura , Martínez J. Alfredo , Milagro Fermín I.
Published: March 2019

The use of biocompounds as agents with potential anti-obesity effects might be a feasible alternative to the prescription of traditional drugs in the near future. The goal of the present study was to screen five different compounds in relation to their ability to prevent body weight gain and ameliorate obesity-associated metabolic impairments, namely insulin resistance. For this purpose, seventy Wistar rats were randomly assigned into seven experimental groups. A standard diet-fed control group (control, n=10); a high-fat, high-sucrose diet-fed group (HFS, n=10) and five experimental groups which were fed the HFS diet supplemented with one of the following biocompounds; curcumin (100 mg/kg bw, n=10), chlorogenic acid (50 mg/kg bw, n=10), coumaric acid (100 mg/kg bw, n=10), naringin (100 mg/kg bw, n=10) and leucine (1 % of diet, n=10). These results confirm the effectiveness of all the compounds to reduce significantly food efficiency, despite the significant higher food intake. Moreover, visceral fat mass percentage was significantly decreased after naringin and coumaric acid supplementation. In fact, this finding might be related to the considerable amelioration of HOMA-IR index detected in naringin-treated animals. A significant reduction in serum insulin levels and an improvement in the intraperitoneal glucose tolerance test and AUC were found in leucine- and coumaric acid-treated rats, respectively. In summary, the tested biocompounds, particularly naringin, coumaric acid and leucine, showed potential benefits in the prevention of obesity-related complications in rats, at least at the proved doses.
Release of Antioxidant Peptides from the Body Wall Proteins of the Sea Cucumber Isostichopus Fuscus
Authors: Hernández-Sámano Arisaí C. , Hernández-Ledesma Blanca
Published: March 2019

Proteases from the tentacles of the sea cucumber Isostichopus fuscus were partially purified and used to produce antioxidant peptides from body wall proteins of this marine species. Three proteins (105, 68, and 39 kDa) were identified by SDS-PAGE in the proteolytic extract of the tentacles. Protein hydrolyzates were generated with gelatin and crude protein substrates from body wall, and peptidic fractions lower and higher than 3 kDa were obtained to evaluate their oxygen radical scavenging capacity (ORAC). The 3 kDa-fraction obtained from the crude protein hydrolyzate showed the highest ORAC value (0.92 ± 0.04 μmol Trolox equivalent/mg protein). This fraction was selected to purify peptides potentially responsible for the activity that might be used as ingredients for development of functional foods.
Chemical Composition of the Essential Oil from Chaerophyllum Temulum (Apiaceae)
Authors: Stamenković Jelena G. , Stojanović Gordana S. , Radojković Ivana R. , Petrović Goran M. , Zlatković Bojan K
Published: March 2019

The present study reports the chemical composition on the essential oil obtained from fresh roots, stems, inflorescences and fruits of Chaerophyllum temulum. In all samples, except the roots, the most dominant components were sesquiterpene hydrocarbons. ( Z)-Falcarinol was the principal constituent of the root essential oils (61.7% at the flowering stage and 62.3% at the fruiting stage). The blossom oil was dominated by ( Z,E)-α-farnesene (23.4%), ( E)-β-farnesene (9.0%) and germacrene D-4-ol (9%), whereas the oil from the fruit had germacrene D-4-ol (27.6%) as its main compound, accompanied by ( Z,E)-α-farnesene (13.4%). Germacrene D was the most abundant component of the stem essential oil (38.4% at the flowering stage and 32.5% at the fruiting stage). The obtained results show that the qualitative composition of the oil depends on the part of the plant which is analyzed, while the quantitative composition of the main components depends on the growing stage of the plant.
Comparison of Essential Oils Obtained from Different Extraction Techniques as an Aid in Identifying Aroma Significant Compounds of Nutmeg (Myristica Fragrans)
Authors: Chatterjee Suchandra , Gupta Sumit , Variyar Prasad. S.
Published: March 2019

Distribution of volatile constituents in the essential oil of nutmeg obtained by simultaneous distillation extraction (SDE), high vacuum distillation (HVD) and super critical fluid extraction (SFE) was compared with reduced pressure distillation (RPD) and head space (HS) analysis. HS and RPD volatiles were characterized by a high content of sabinene, followed by α-pinene and β-pinene. Interestingly, unlike the SDE, HVD and SFE oils, distillates from HS and RPD were marked by the absence of phenolic ethers namely myristicin, elemicin and safrole. The HS and RPD volatiles possessed a pleasant nutmeg aroma indicating a significant role of terpenic constituents in contributing to the top aroma note. GC-olfactometry (GC-O) of the oils aided in establishing the role of sabinene, α-pinene and β-pinene in contributing to the distinctive note of the spice. A high odor activity value (OAV) of sabinene and α-pinene established the role of these two constituents in imparting the characteristic nutmeg odor.
Chemical Variability of the Essential Oil Isolated from Aerial Parts of Tetraclinis Articulata from North-Western Algeria
Authors: Boussaïd Maghnia , Bekhechi Chahrazed , Beddou Fawzia , Sari Daoudi Chabane , Bighelli Ange , Casanova Joseph , Tomi Félix
Published: March 2019

The objective was to investigate the yield and chemical composition of 50 essential oil samples isolated from leaves and flowers of Tetraclinis articulata harvested in eight locations (coastal township and highlands) of Tlemcen Province (North-Western Algeria). Essential oil yields varied drastically from sample to sample (0.03 to 0.86%, w/w). No direct correlation was observed between the yield and the altitude of the harvest areas. The oils consisted mainly of monoterpenes: α-pinene (9.2–56.5%), bornyl acetate (1.2–45.1%), camphor (0.5–40.3%), borneol (0.2–12.9%), limonene (3.6–12.5%), and myrcene (1.6–9.7%). Sesquiterpenes were represented by germacrene D (up to 14.2%) and (E)-β-caryophyllene (up to 13.3%). PCA analysis of the data allowed the distinction of two groups within the samples. The composition of group I (9 samples) was dominated by camphor, (Mean = 30.9%) followed by α-pinene (M = 19.1%) and bornyl acetate (M = 11.4%). Group II was divided into two sub-groups. Samples of sub-group IIA (8 samples) contained mainly α-pinene (M = 45.4%). Samples of the largest group IIB (33 samples) were characterized by similar contents of α-pinene (M = 28.2%) and bornyl acetate (M = 24.5%) and the occurrence of camphor to a lesser extent (M = 10.0%).
Chemical Composition of the Essential Oil from Croton Oblongifolius and its Antibacterial Activity Against Propionibacterium Acnes
Authors: Athikomkulchai Sirivan , Tadtong Sarin , Ruangrungsi Nijsiri , Hongratanaworakit Tapanee
Published: March 2019

The essential oil of C. oblongifolius Roxb. stem bark was obtained by hydrodistillation. Chemical analysis by GC-MS identified 29 compounds. Terpinen-4-ol (17.8%) was a major component, together with α-guaiene (7.9%), E-caryophyllene (7.0%), myrcene (6.7%), (+)-cyclosativene (5.1%), sabinene (4.8%), aciphyllene (4.7%), pogostol (4.6%), γ-terpinene (3.4%), α-muurolol (3.2%) and germecrene D (3.2%). The essential oil exhibited antibacterial activity against Propionibacterium acnes ATCC 6919 with an MIC of 0.125%, v/v.
Composition, in Vitro Anti-inflammatory, Antioxidant and Antimicrobial Activities of Essential Oils from Leaf and Twig Parts of Cupressus Cashmeriana
Authors: Su Yu-Chang , Hsu Kuan-Ping , Hua Kuo-Feng , Ho Chen-Lung
Published: March 2019

The chemical composition and in vitro anti-inflammatory, antioxidant and antimicrobial activities of the essential oils isolated from the leaf and twig of Cupressus cashmeriana have been investigated. The essential oils were isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC–FID and GC–MS, respectively. The leaf oil mainly consisted of α-pinene (21.8%), epizonarene (8.0%), sabinene (7.9%), limonene (7.6%), γ-terpinene (7.0%), and allo-aromadendrene (7.0%); the twig oil was mostly carvacrol methyl ether (35.4%), manool (16.1%), carvacrol (14.2%), and (2 Z,6 E)-farnesol (6.9%). Twig oil, but not leaf oil, was able to reduce nitric oxide production by lipopolysaccharide-activated murine macrophages RAW 264.7 without reducing the cell viability. In addition, twig oil showed better antioxidant and antimicrobial activities than leaf oil. The major ingredient of the twig oil that was responsible for the anti-inflammatory, antioxidant and antimicrobial activities was carvacrol.
Antioxidant and Anticholinesterase Activities of Essential Oils of Cinnamomum Griffithii and C. Macrocarpum
Authors: Salleh Wan Mohd Nuzul Hakimi Wan , Ahmad Farediah , Yen Khong Heng
Published: March 2019

The essential oils of Cinnamomum griffithii and C. macrocarpum were analyzed by GC and GC–MS and evaluated for their antioxidant and anticholinesterase activities. The essential oils of leaf and bark of C. griffithii were characterized by the presence of 30 components, with methyl eugenol (38.5–43.8%) as the major component. A total of 11 components were characterized in the leaf and bark of C. macrocarpum essential oil with the most abundant component was safrole (54.5–59.5%). The bark oil of C. griffithii demonstrated significant activity on DPPH (IC50 73.4 μg/mL) and a high phenolic content (192.0%), while the leaf oil inhibited oxidation of β-carotene/linoleic acid with an inhibition value of 65.5 μg/mL. Acetylcholinesterase and butyrylcholinesterase inhibition were assessed and the results showed that C. macrocarpum bark oil exhibited significant activity with inhibition values of 55.8% and 66.1%, respectively at a concentration of 1 mg/mL.
Essential Oil Composition and Antigermination Activity of Artemisia Dracunculus (Tarragon)
Authors: Fraternale Daniele , Flamini Guido , Ricci Donata
Published: March 2019

The chemical composition of an Italian oil of tarragon ( Artemisia dracunculus L.) was analyzed by GC/EIMS. The major compound of the oil was estragole (73.3%), followed by limonene (5.4%), ( E)-β-ocimene (5.3%), β-pinene (3.4%) and ( Z)-β-ocimene (3.0%). The essential oil was tested “ in vitro” for its antigermination activity against Raphanus sativus L., Lepidium sativum L, Papaver rhoeas L. and Avena fatua L. seeds and demonstrating a good inhibitory activity in a dose-dependent way.
Alarm Pheromone Activity of Nymph-specific Geraniol in Chrysanthemum Lace Bug Corythucha marmorata against Adults and Nymphs
Authors: Watanabe Kisaki , Shimizu Nobuhiro
Published: March 2019

The exotic insect pest Corythucha marmorata (Uhler) is increasingly spreading in Japan using the weed Solidago canadensis L. as a major host plant. The nymphs form colonies on the backs of leaves where they crowd together; however, aggregation does not occur in the adults. When an individual nymph is crushed using a needle tip and further the needle tip covered with the nymph's bodily fluids is moved slowly toward the center of the crowd, the surrounding nymphs display an escape behavior and their aggregation is disrupted. We detected geraniol as a nymph-specific volatile component. Bioassay results indicated that geraniol was effective as an alarm pheromone on second to fifth instar nymphs. Furthermore, we found that male and female adults responded sensitively to the alarm pheromone produced by nymphs. These results suggest that although the adult insects do not secrete geraniol, they can detect it produced by nymphs, thereby retaining the ability to escape from danger while suppressing the cost of geraniol production. The present study is the first to demonstrate that an alarm pheromone secreted by nymphs is also effective in adults among Tingidae.
One New Conjugate of a Secoiridoid Glucoside with a Sesquiterpene Glucoside from the Flower Buds of Lonicera japonica
Authors: Yang Biao , Meng Zhaoqing , Ma Yimin , Wang Zhenzhong , Ding Gang , Huang Wenzhe , Sun Lin , Hu Yumei , Liu Wenjun , Zhang Chunxiao , Cao Zeyu , Li Jiachun , Zhong Yan , Xiao Wei
Published: March 2019

Secosesquside (1), a new secoiridoid glucoside-sesquiterpene conjugate, together with three known secoiridoid derivatives, were isolated from flower buds of Lonicera japonica. The isolated compounds were elucidated by extensive spectroscopic analyses, especially 2D NMR experiments. The anti-inflammatory activities of the new compound were also evaluated by enzyme-linked immunosorbent assay.
Chemical Originalities of New Caledonian Liverworts from Lejeuneaceae Family
Authors: Coulerie Paul , Thouvenot Louis , Nour Mohammed , Asakawa Yoshinori
Published: March 2019

Lejeuneaceae is the largest family of liverworts in the world. Through the analyses of the chemical composition of some species, it has been demonstrated that they may represent an important source of original and bioactive molecules. None of the 146 species that occur in New Caledonia has been studied yet. Here we describe the terpenoid content of twelve New Caledonian species, including two endemics. We describe here, for the first time, the presence of frullanolide in the Lejeuneaceae, occurring as a major compound in the extract from Colura leratii, and a rarely observed santalene derivative from Acrolejeunea securifolia subsp. caledonica. These analyses also highlight species that probably contain original structures, such as Schiffneriolejeunea tumida var. hasskarliana, Cheilolejeunea spp and Thysananthus retusus. The results obtained here also confirm several previous hypotheses about the chemosystematics of the Lejeuneaceae. For example, lepidozene can be considered as a chemosystematic marker of the Ptychantoideae subfamily, considering its abundance in many Ptychantoideae. On the other hand, some results are different from those described previously. For example, we detected no fusicoccane derivatives in any of the Lejeuneaceae species analyzed here, whereas they were previously described as a marker of the Ptychantoideae. This suggests that the available data toward the chemistry of the Lejeuneaceae are not sufficient to be confident with some of the previous chemosystematic conclusions.