bluuebunny/crossref_metadata_2025 huggingface dataset:
Repellent and Anti-quorum Sensing Activity of Six Aromatic Plants Occurring in Colombia
Authors: Cervantes-Ceballos Leonor , Caballero-Gallardo Karina , Olivero-Verbel Jesus
Published: March 2019

Essential oils (EOs) are widely used as biopesticides and to control bacterial infections. This study describes the ability of six EOs isolated from plants cultivated in Colombia to perform as repellents against Ulomoides dermestoides and as quorum sensing (QS) inhibitors. EOs from Aloysia triphylla, Cymbopogon nardus, Lippia origanoides, Hyptis suaveolens, Swinglea glutinosa ami Eucalyptus globulus were repellents classified as Class IV, IV, IV, III, II, and II, respectively, whereas the commercial repellent IR3535 only reached Class II after 2 h exposure. All EOs presented small, but significant inhibitory properties against the QS system in Escherichia coli (pJBA132) at 25 μg/mL after 4 h exposure. These data suggest evaluated EOs from Colombia are sustainable, promising new sources of natural repellents and could be important as anti-quorum sensing molecules.
Chemical Composition Variability of the Herb Essential Oil in the Ontogenesis of Artemisia campestris subsp. campestris
Authors: Lis Anna , Kowal Martyna , Kończak Joanna
Published: March 2019

The essential oil from the herb of Artemisia campestris L. subsp. campestris harvested at five ontogenesis phases was analyzed by GC, GC/MS and 1H NMR spectroscopy. More than 130 compounds were identified. Terpene hydrocarbons dominated in the oil. Germacrene D (20.3-30.1%), β-pinene (3.7-15.4%) and γ-humulene (6.6-9.8%) were the main constituents. The contents of germacrene D and γ-humulene decreased from the phase before bud formation to the beginning of flowering, then increased until the post-flowering phase. The content of β-pinene at the same periods firstly increased, and then was reduced.
The Interaction of Alpha-synuclein with Membranes and its Implication in Parkinson's Disease: A Literature Review
Authors: Gonzalez-Horta Azucena
Published: March 2019

Alpha-synuclein belongs to the class of intrinsically disordered proteins lacking a well-folded structure under physiological conditions. The conversion of alpha-synuclein from a soluble monomer to an insoluble fibril may underlie the neurodegeneration associated with Parkinson's disease (PD). Although the exact mechanism of alpha-synuclein toxicity is still unknown, it has been proposed that alpha-synuclein disturbs membrane structure, leading to increased membrane permeability and eventual cell death. This review highlights the significant role played by fluorescence techniques in unraveling the nature of interactions between alpha-synuclein and membranes and its implications in PD.
Vibrational Circular Dichroism: Recent Advances for the Assignment of the Absolute Configuration of Natural Products
Authors: Burgueño-Tapia Eleuterio , Joseph-Nathan Pedro
Published: March 2019

Vibrational circular dichroism (VCD) emerged during the last decade as a reliable tool for the absolute configuration (AC) determination of organic compounds. The principles, instrumentation, and methodology applied prior to early 2013 were recently reviewed by us. Since VCD is a very dynamic field, the aim of this review is to update VCD advances for the AC assignment of terpenoids, aromatic compounds, alkaloids, and other natural products for the 2013-2014 period, when VCD was applied to the AC assignment of some 70 natural products. In addition, although discovered in 2012, a brief introduction to the VCD exciton coupling approach and its applications in natural products AC assignment is presented.
Study of an Acid-Free Technique for the Preparation of Glycyrrhetinic Acid from Ammonium Glycyrrhizinate in Subcritical Water
Authors: Lekar Anna V. , Borisenko Sergey N. , Vetrova Elena V. , Filonova Olga V. , Maksimenko Elena V. , Borisenko Nikolai I. , Minkin Vladimir I.
Published: March 2019

The aim of this work was to study an application of a previously developed expedient acid-free technique for the preparation of glycyrrhetinic acid from ammonium glycyrrhizinate that requires no use of acids and toxic organic solvents. Subcritical water that serves as a reactant and a solvent was used in order to obtain glycyrrhetinic acid in good yields starting from ammonium glycyrrhizinate. It has been shown that variation of only one parameter of the process (temperature) allows alteration to thecomposition of the hydrolysis products. A new method was used for the synthesis of glycyrrhetinic acid (glycyrrhizic acid aglycone) and its monoglycoside. HPLC combined with mass spectrometry and NMR spectroscopy were used to determine the quantitative and qualitative compositions of the obtained products. The method developed for the production of glycyrrhetinic acid in subcritical water is environmentally friendly and faster than conventional hydrolysis methods that use acids and expensive and toxic organic solvents. The proposed technique has a potential for the future development of inexpensive and environmentally friendly technologies for production of new pharmaceutical plant-based substances.
Complexes of Lapachol and Lawsone with Lanthanides
Authors: Genovese Salvatore , Taddeo Vito Alessandro , Epifano Francesco , Fiorito Serena
Published: March 2019

Naturally occurring 2-hydroxy-1,4-naphthoquinones are well known to form readily stable complexes with transition metals. In this short communication we describe for the first time the synthesis and preliminary data about structural characterization of complexes between two naturally widespread 2-hydroxy-1,4-naphthoquinones, namely lapachol (1) and lawsone (2), with selected lanthanides like lanthanum, gadolinium, and ytterbium. When tested as cytotoxic compounds, such complexes exhibited an activity that was either higher or equal to that of the parent naphthoquinone.
Antioxidant Activity and Polyphenol Content of Some Brazilian Medicinal Plants Exploiting the Formation of the Fe(II)/2,2′-bipyridine Complexes
Authors: Santana Waila Evelyn Lima , Nunez Cecilia Verônica , Moya Horacio Dorigan
Published: March 2019

Aqueous plant extracts contain polyphenols that reduce Fe3+ to Fe2+, which in the presence of excess 2,2′-bipyridine (bipy) yield the Fe( bipy)32+ complex (max = 521 nm). This reaction was used to quantify the total polyphenol content (TPC) of nineteen Brazilian medicinal species using pyrogallic acid (PA) as a standard. A calibration curve of absorbance values at 521 nm values vs. PA was linear from 0.378 to 3.03 mg L-1 (r = 0.998; n = 8) with a limit of detection 0.16 mg L-1. The TPC quantification using the proposed reaction was compared with values obtained with the Folin-Ciocalteu reagent, yielding good agreement (r = 0.965). For the same species the TPC obtained with the proposed method also resulted in good correlation (r = 0.773) with the antioxidant capacity values quantified using the 2,2-diphenyl-1-picrylhydrazyl method. It was also found that Fe( bipy)32+ complexes can be used to calculate the reducing capability of polyphenols. The polyphenol structure, and the number and position of the hydroxyl group attached to the benzene ring modify this reductive capacity.
HPLC Analysis, Antioxidant, Anti-inflammatory and Xanthine Oxidase Inhibitory Activity of Cudrania tricuspidata
Authors: Nile Shivraj Hariram , Kim Doo Hwan
Published: March 2019

Cudrania tricuspidata is a plant used in folk medicine in Korea for treatment of diseases related to oxidative stress and inflammation. In this study the leaf and shoot extract was studied for its antioxidant, anti-inflammatory, and xanthine oxidase (XO) inhibitory activities. The extract with predominant phenolics was quantified using HPLC-DAD. Antioxidant activity was measured using ABTS [2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) and FRAP (ferric ion reducing antioxidant power), and anti-inflammatory activity by diene-conjugate and β-glucuronidase assays. The average antioxidant effects of C. tricuspidata extracts (1–2 mg/mL) revealed significant activity of 32.5% to 50.2% (ABTS) and 24.2 to 40.5% (FRAP) compared with Trolox, having 55.1% (ABTS) and 42.6% (FRAP) activity, respectively. The anti-inflammatory activities showed as 26.5% to 40.5% (DC) and 40.2% to 70.2% (βG) inhibition compared with the control {phenylbutazone; 42.1% (DC) and 80.2% (βG) inhibition, respectively}. The XO inhibitory activity of the plant extract revealed 90.5% inhibition of that of the control (allopurinol) (97% inhibition at 100 μg/mL concentration). The kinetic parameters of XO inhibition revealed a noncompetitive type of inhibition, where, K m and V max of C. tricuspidata extracts (25 to 100 μg/mL) were 0.25 mM/mL and 0.040, 0.036, 0.032, and 0.030 (μg/min), while for the positive control K m and V max the values were 0.30 mM/mL and 0.045 (μg/min), respectively. Results suggest that C. tricuspidata can be exploited against diseases associated with free radical formation and xanthine oxidase activity.
Chemistry and Pharmacognosy of the Genus Durio
Authors: Rudiyansyah  , Panthong Kanda , Garson Mary J
Published: March 2019

Durio is well known as one of the sources of seasonal fruit production in Southeast Asia with its center of diversity in Borneo. Thailand, Indonesia, and Malaysia are the main Durio producers in the world. Besides having much information about the utilization and benefit from its timber and fruits as a food substance, traditionally some parts of this plant, such as leaves, bark and root, can also be used for medical purposes. This review deals with chemical constituents and the biological activities of Durio plants.
Organoselenium Compounds as Phytochemicals from the Natural Kingdom
Authors: Achibat Hanane , AlOmari Nohad A , Messina Federica , Sancineto Luca , Khouili Mostafa , Santi Claudio
Published: March 2019

Selenium is naturally present in soils but it is also produced by pollution from human activities into the environment. Its incorporation into plants affords organoselenium metabolites that, depending on the nature of the molecules and the plant species, can be incorporated into proteins, stored or eliminated by volatilization. The possibility to use the selenium metabolism of some plants as a method for bioremediation and, at the main time, as a source of selenated phytochemicals is here discussed taking into consideration the growing interest in organic selenium derivatives as new potential therapeutic agents.
Steroidal Saponins from the Mesocarp of the Fruits of Raphia farinifera (Arecaceae) and their Cytotoxic Activity
Authors: Tapondjou Léon A. , Siems Kristina J. , Böttger Stefan , Melzig Matthias F.
Published: March 2019

Eight steroidal saponins (1–8), including one previously unreported derivative (1), have been isolated from the mesocarp of Raphia farinifera fruits by combined column chromatography and RP-HPLC methods. They were characterized by spectroscopic (1D and 2D NMR experiments) and spectrometric (ESIMS) methods, as well as by comparison of their spectral data with those of reported compounds in the literature. All the isolated compounds were tested for cytotoxicity against urinary bladder carcinoma cells (ECV-304). Our results revealed that, for a high cytotoxicity, a sugar chain of at least three sugar moieties attached to C-3 of the steroidal saponin is necessary.
Ruta graveolens Extracts and Metabolites against Spodoptera frugiperda
Authors: Ayil-Gutiérrez Benjamín A. , Villegas-Mendoza Jesús M. , Santes-Hernández Zuridai , Paz-González Alma D. , Mireles-Martínez Maribel , Rosas-García Ninfa M. , Rivera Gildardo
Published: March 2019

The biological activity of Ruta graveolens leaf tissue extracts obtained with different solvents (ethyl acetate, ethanol, and water) and metabolites (psoralen, 2-undecanone and rutin) against Spodoptera frugiperda was evaluated. Metabolites levels in extracts were quantified by HPLC and GC. Ethyl acetate and ethanol extracts showed 94% and 78% mortality, respectively. Additionally, psoralen metabolite showed a high mortality as cypermethrin. Metabolite quantification in extracts shows the presence of 2-undecanone (87.9 μmoles mg−1 DW), psoralen (3.6 μmoles mg−1 DW) and rutin (0.001 μmoles mg−1 DW). We suggest that these concentrations of 2-undecanone and psoralen in R. graveolens leaf tissue extracts could be responsible for S. frugiperda mortality.
A Novel Acylated Anthocyanin with a Linear Trisaccharide from Flowers of Convolvulus althaeoides
Authors: Cabrita Luis
Published: March 2019

An acylated anthocyanin trioside was isolated from pink flowers of Convolvulus althaeoides using a combination of chromatographic techniques. On the basis of MS (MALDI-TOF) and NMR (1H NMR, 1H-1H COSY, 1D TOCSY, HSQC, HMBC, 13C CAPT) its structure was determined as cyanidin 3- O-[6- O-(4- O-(6- O-( E-caffeoyl)-β-D-glucopyranosyl)-α-L-rhamnopyranosyl)-β-D-glucopyranoside]-5- O-β-D-glucopyranoside. The absolute configuration of the aldose enantiomer moieties was determined from the separation of the corresponding thiazolidine diastereoisomer derivatives by HPLC-DAD. This is a novel trisaccharide within the flavonoids, and the first complete characterization of a linear glucosyl-rhamnosyl-glucoside (4′-glucosylrutinoside) within the anthocyanins. Whilst acylation of rhamnose moieties in position 4 is quite common, the occurrence in anthocyanins of a glycosylated rhamnose is a unique trait. Although many complex anthocyanins have been found amongst the Convolvulaceae, the genus Convolvulus had not yet been surveyed for anthocyanins and thus this account could be of significance within the current chemotaxonomy of this family.
Synergy Effects of Three Plant Extracts on Protection of Gastric Mucosa
Authors: Wang Caihui , Su Wen , Su Xingli , Ni Guojun , Liu Tao , Kong Yi
Published: March 2019

The gastric mucosa protection effect of three natural plant extracts, Hericium erinaceus (HE), Centella asiatica (CA) and Amomum villosum (AV), were evaluated using the indomethacin damage model. Compared with a single extract, a combination of HE/CA/AV, especially with the ratios of 80:10:10, 45:45:10 and 45:10:45, showed significant synergistic effects for protection of the gastric mucosa with gastric ulcer inhibition rates of 97.8 ± 0.7%, 86.5 ± 2.8% and 86.1 ± 3.6%, respectively. Microscopic appearances of the gastric mucosa were carried out to help confirm the results.
Aloe arborescens Extract Protects IMR-32 Cells against Alzheimer Amyloid Beta Peptide via Inhibition of Radical Peroxide Production
Authors: Clementi Maria Elisabetta , Tringali Giuseppe , Triggiani Doriana , Giardina Bruno
Published: March 2019

Aloe arborescens is commonly used as a pharmaceutical ingredient for its effect in burn treatment and ability to increase skin wound healing properties. Besides, it is well known to have beneficial phytotherapeutic, anticancer, and radio-protective properties. In this study, we first provided evidence that A. arborescens extract protects IMR32, a neuroblastoma human cellular line, from toxicity induced by beta amyloid, the peptide responsible for Alzheimer's disease. In particular, pretreatment with A. arborescens maintains an elevated cell viability and exerts a protective effect on mitochondrial functionality, as evidenced by oxygen consumption experiments. The protective mechanism exerted by A. arborescens seems be related to lowering of oxidative potential of the cells, as demonstrated by the ROS measurement compared with the results obtained in the presence of amyloid beta (1–42) peptide alone. Based on these preliminary observations we suggest that use of A. arborescens extract could be developed as agents for the management of AD.
Megastigmane Glycosides from the Leaves of Tripterygium wilfordii
Authors: Ni Lin , Zhang Xiao-mei , Zhou Xing , Ma Jie , Li Chuang-jun , Li Li , Zhang Tian-tai , Zhang Dong-Ming
Published: March 2019

Two new megastigmane glycosides, named wilfordonisides A and B (1 and 2), and four known compounds (3–6) were isolated from the leaves of Tripterygium wilfordii, and one new aglycon, named wilfordoninol A (2a), was acquired by enzymatic hydrolysis of 2. The absolute stereostructures of the compounds were determined by Mosher's method and by CD. At a concentration of 10 μM, compounds 1, 3, and 5 inhibited STAT1 translocation by 38.1 ± 0.9%, 55.8 ± 0.8%, and 53.9 ± 1.0%, respectively.
Macrocyclic Diterpenoids from the Latex of Euphorbia helioscopia
Authors: Hua Juan , Liu Yan-Chun , Jing Shu-Xi , Luo Shi-Hong , Li Sheng-Hong
Published: March 2019

One new jatrophane diterpenoid, 7α,9β,15β-triacetoxy-3β-benzoyloxy-14β-hydroxyjatropha-5 E,11 E-diene (3), together with four known macrocyclic diterpenoids, euphoheliosnoid A (1), epieuphoscopin B (2), euphohelioscopin A (4) and euphoscopin C (5), were isolated from the stem latex of Euphorbia helioscopia. Their structures were established by spectroscopic analyses. In the anti-inflammatory assay, euphohelioscopin A (4) exhibited moderate inhibitory activity on the release of cytokine TNF-α (IC50 = 23.7 ± 1.7 μM), IL-6 (IC50 = 46.1 ± 1.1 μM) and chemokine MCP-1 (IC50 = 33.7 ± 3.8 μM) in lipopolysaccharide (LPS) induced RAW 264.7 macrophages without notable cytotoxicity (IC50 > 80 μM).
Diterpenoid Alkaloids from Aconitum soongaricum var. pubescens
Authors: Chen Lin , Shan Lianhai , Zhang Jifa , Xu Wenliang , Wu Mingyu , Huang Shuai , Zhou Xianli
Published: March 2019

One new diterpenoid alkaloid, pubescensine (1), along with nine known diterpenoid alkaloids (2–10) were isolated from the roots of Aconitum soongaricum var. pubescens. Their structures were elucidated by spectroscopic analyses and comparison with previously reported data. All the compounds were evaluated for their antifeedant activities. The aconitine-type diterpenoid alkaloids (1–6) showed considerably potent antifeedant activity (EC50 < 1 mg/cm2), while the activities of napelline-type diterpenoid alkaloids (compds. 7, 9 and 10) were not significant (EC50 > 50 mg/cm2).
Further Studies on Structure-Cardiac Activity Relationships of Diterpenoid Alkaloids
Authors: Zhang Zhong-Tang , Jian Xi-Xian , Ding Jia-Yu , Deng Hong-Ying , Chao Ruo-Bing , Chen Qiao-Hong , Chen Dong-Lin , Wang Feng-Peng
Published: March 2019

The cardiac effect of thirty-eight diterpenoid alkaloids was evaluated on the isolated bullfrog heart model. Among them, twelve compounds exhibited appreciable cardiac activity, with compounds 3 and 35 being more active than the reference drug lanatoside. The structure-cardiac activity relationships of the diterpenoid alkaloids were summarized based on our present and previous studies [2]: i) 1α-OMe or 1α-OH, 8-OH, 14-OH, and NH (or NMe) are key structural features important for the cardiac effect of the aconitine-type C19-diterpenoid alkaloids without any esters. C18-diterpenoid alkaloids, lycoctonine-type C19-diterpenoid alkaloids, and the veatchine- and denudatine-type C20-diterpenoid alkaloids did not show any cardiac activity; ii) the presence of 3α-OH is beneficial to the cardiac activity; iii) the effect on the cardiac action of 6α-OMe, 13-OH, 15α-OH, and 16-demethoxy or a double bond between C-15 and C-16 depends on the substituent pattern on the nitrogen atom.
Synthesis and Anti-Proliferative Effects of Quercetin Derivatives
Authors: Al-Jabban Sami M.R. , Zhang Xiaojie , Chen Guanglin , Mekuria Ermias Addo , Rakotondraibe Liva Harinantenaina , Chen Qiao-Hong
Published: March 2019

Prostate cancer is the most common diagnosed invasive cancer in American men and is the second leading cause of cancer-related deaths. Although there are several therapies successful in treating early, localized stage prostate cancer, current treatment of advanced metastatic castration-resistant prostate cancer remains ineffective due to inevitable progression of resistance to first-line treatment with docetaxel. The natural product quercetin (3,3′,4′,5,7-pentahydroxyflavone), a flavonoid compound ubiquitous in dietary plants, possesses evidenced potential in treating advanced metastatic castration-resistant prostate cancer. However, its poor bioavailability and moderate potency hinder its advancement into clinical therapy. In order to engineer quercetin derivatives with improved potency and pharmacokinetic profiles for the treatment of advanced metastatic prostate cancer, we started this study with creating a small library of alkylated derivatives of quercetin for in vitro evaluation. The biological data and chemical reactivity of quercetin and its derivatives reported in literature directed us to design 3,4′,7- O-trialkylquercetins as our first batch of targets. Consequently, nine 3,4′,7- O-trialkylquercetins, together with four 3,7- O-dialkylquercetins, four 3,3′,4′,7-tetraalkylquercetins, and one 3,3′,4′- O-trialkylquercetin, were prepared by one step O-alkylation of commercially available quercetin mediated by potassium carbonate. Their structures were determined by 1D and 2D NMR data, and HRMS. Their anti-proliferative activities towards both androgen-refractory and androgen-sensitive prostate cancer cells were evaluated using WST-1 cell proliferation assay. The acquired structure-activity relationships indicate that 3,7- O-dialkylquercetins rather than 3,4′,7- O-trialkylquercetins were much more potent than quercetin towards prostate cancer cells.
12-Membered Resorcylic Acid Lactones Isolated from Saccharicola bicolor, an Endophytic Fungi from Bergenia purpurascens
Authors: Guo Da-Le , Zhao Min , Xiao Shi-Ji , Xia Bing , Wan Bo , Gu Yu-Cheng , Ding Li-Sheng , Zhou Yan
Published: March 2019

Two new resorcylic acid lactones, 13-hydroxyhidroresorcylide (1) and 12-hydroxyhidroresorcylide (2), along with four known congeners (3–6) were isolated from Saccharicola bicolor, an endophytic fungus from Bergenia purpurascens. Their structures were elucidated by interpretation of the spectroscopic evidence.
A New Bithiophene from the Root of Echinops grijsii
Authors: Chang Fang-Pin , Chen Chien-Chih , Huang Hui-Chi , Wang Sheng-Yang , Chen Jih-Jung , Yang Chang-Syun , Ou Chung-Yi , Wu Jin-Bin , Huang Guan-Jhong , Kuo Yueh-Hsiung
Published: March 2019

A new bithiophene, 5-(4-hydroxy-3-methoxy-1-butyny)-2,2′-bithiophene (1), and sixteen known thiophenes: 2-(3,4-dihydroxybut-1-ynyl)-5-(penta-1,3-diynyl)thiophene (2), α-terthienyl (3), 5-(3,4-dihydroxybut-1-ynyl)-2,2′-bithiophene (4), 5-acetyl-2,2′-bithiophene (5), 5-formyl-2,2′-bithiophene (6), methyl 2,2′-bithiophene-5-carboxylate (7), 5-(but-3-en-1-ynyl)-2,2′-bithiophene (8), 5-(4-isovaleroyloxybut-1-ynyl)-2,2′-bithiophene (9), cardopatine (10), isocardopatine (11), 5-(3-hydroxy-4-isovaleroyloxybut-1-ynyl)-2,2′-bithiophene (12), 5-(3-hydroxymethyl-3-isovaleroyloxyprop-1-ynyl)-2,2′-bithiophene (13), 5-(4-hydroxy-1-butynyl)-2,2′-bithiophene (14), 5-(4-acetoxy-1-butynl)-2,2′-bithiophene (15), 2,2′-bithiophene-5-carboxylic acid (16) and 2-(4-hydroxybut-1-ynyl)-5-(penta-1,3-diynyl)thiophene (17) were isolated from the roots of Echinops grijisii Hance. Among them, compounds 6, 7 and 16 were isolated from a natural source for the first time. Compounds 2, 4 and 14 exhibited significant anti-inflammatory activity against nitrite of LPS-stimulated production in the RAW 264.7 cell line.
Cyclic Lipopeptides with Herbicidal and Insecticidal Activities Produced by Bacillus clausii DTM1
Authors: Guo Da-Le , Wan Bo , Xiao Shi-Ji , Allen Sarah , Gu Yu-Cheng , Ding Li-Sheng , Zhou Yan
Published: March 2019

Seven cyclic lipopeptide biosurfactants (1–7) were isolated for the first time from the fermentation broth of endophytic Bacillus clausii DTM1 and were identified as anteisoC13[Val7] surfactin-(L-Glu)-O-methyl-ester (1), anteisoC12[Val7] surfactin (2), anteisoC15[Val7] surfactin (3), isoC14[Leu7] surfactin (4), anteisoC12[Leu7] surfactin (5), nC13[Leu7] surfactin (6), and anteisoC14[Leu7] surfactin-(L-Glu)-O-methyl-ester (7); 1 has not been isolated before as a natural product from any source. Plate-based herbicide and insecticide bioassays showed that all compounds exhibited interesting insecticidal and herbicidal activities.
Serum Metabolomic Profiling of Rats by Intervention of Aconitum soongaricum
Authors: Zhang Fan , Liu Jiao , Lei Jun , He Wenjing , Sun Yun
Published: March 2019

To understand the toxic mechanism and to find the changes in the endogenous metabolites of Aconitum soongaricum Stapf for clinical detection, a combination of 1H NMR spectroscopy and multivariate statistical analysis was applied to examine the metabolic profiles of the blood serum samples collected from the rat model. In total, thirteen biomarkers of A. soongaricum were found and identified. It turned out that A. soongaricum treatment may partially disorder the metabolism. The study has shown the potential application of NMR-based metabolomic analysis in providing further insights into the toxicity caused by A. soongaricum.
Chemical Synthesis of the Echinopine Sesquiterpenoids
Authors: Liu Xiao-Yu , Qin Yong
Published: March 2019

As new members of the sesquiterpenoid family, echinopines A and B were found to possess an unprecedented [3/5/5/7] carbon framework, which has stimulated considerable interest among the chemistry community since their isolation. This review article documents chronologically the steps towards chemical synthesis of the echinopine sesquiterpenoids, showcasing different strategies by resorting to the toolkit of organic chemistry.
Isolation and Characterization of Sclerienone C from Scleria Striatinux
Authors: Nyongbela Kennedy D. , Makolo Felix L. , Hoye Thomas R. , Efange Simon MN
Published: March 2019

Herein, we report the isolation and characterization of sclerienone C, a novel sesquiterpene isolated from the methylene chloride/methanol (1:1) extract of Scleria striatinux that we have deduced to have structure 1. This medicinal spice of Cameroon has been shown to display antimicrobial and antiplasmodial activities. The isolation and purification involved a combination of methods including silica gel column chromatography, Sephadex LH-20, and semi-prep HPLC separations. Structure elucidation was carried-out by means of spectroscopic analysis and comparison with previously isolated sesquiterpene derivatives from the plant.
Cytotoxic and Pro-apoptotic Activities of Sesquiterpene Lactones from Inula Britannica
Authors: Xiang Ping , Guo Xin , Han Yang-Yang , Gao Jin-Ming , Tang Jiang-Jiang
Published: March 2019

In this study, five known sesquiterpene lactones (STL) with an α-methylene-γ-lactone motif, including two eudesmanolides, 1β-hydroxyalantolactone (1) and ivangustin (2), and three 1,10-seco-eudesmanolides, 1- O-acetylbritannilactone (3), 1,6- O, O-diacetylbritannilactone (4), and 6α- O(2-methylbutyryl)britannilactone (5) were isolated from the flower heads of the medicinal plant Inula britannica. Their structures were characterized by spectroscopic methods. X-ray data of 2 is reported for the first time. Among them, eudesmanolides 1 and 2 exhibited remarkable cytotoxicity against HEp2, SGC-7901 and HCT116 human cancer cell lines, comparable with etoposide (Vp-16) used as reference drug. Furthermore, treatment of HEp2 cells with 1 induced apoptosis associated with cleaved procaspase-3 and PARP. The biological assays carried out with normal cells (CHO) revealed that all sesquiterpenes were weakly selective against the cancer cell lines tested.
Influence of Merosesquiterpenoids from Marine Sponges on Seedling Root Growth of Agricultural Plants
Authors: Chaikina Elena L. , Utkina Natalia K. , Anisimov Mikhail M.
Published: March 2019

The impact of the merosesquiterpenoids avarol (1), avarone (2), 18-methylaminoavarone (3), melemeleone A (4), isospongiaquinone (5), ilimaquinone (6), and smenoquinone (7), isolated from marine sponges of the Dictyoceratida order, was studied on the root growth of seedlings of buckwheat ( Fagopyrumesculentum Moench), wheat ( Triticumaestivum L.), soy ( Glycine max (L.) Merr.), and barley ( Hordeumvulgare L.). Compounds 2 and 6 were effective for the root growth of wheat seedlings, compound 3 stimulated the root growth of seedlings of buckwheat and soy, compound 4 affected the roots of barley seedlings, and compound 5 stimulated the root growth of seedlings of buckwheat and barley. Compounds 1 and 7 showed no activity on the root growth of the seedlings of any of the studied plants. The stimulatory effect depends on the chemical structure of the compounds and the type of crop plant.
A New Taraxastane-type Triterpenoid from Cleistocalyx Operculatus
Authors: Giang Phan Minh , Phuong Vu Thi Thu , Chinh Truong Thi To
Published: March 2019

Ten known compounds including a chalcone, a long-chain alcohol, two flavonols, and six triterpenoids/steroids together with a new taraxastane-type triterpenoid, named cleistocalyxin, were isolated from the leaves of Cleistocalyx operculatus. The structure of cleistocalyxin was determined on the basis of IR, MS and NMR spectroscopic methods.
Steroidal Glucosides from the Rhizomes of Tacca Chantrieri and Their Inhibitory Activities of NO Production in BV2 Cells
Authors: Yen Pham Hai , Chi Vu Thi Quynh , Kim Dong-Cheol , Ko Wonmin , Oh Hyuncheol , Kim Youn-Chul , Dung Duong Thi , Thanh Nguyen Thi Viet , Quang Tran Hong , Ngan Nguyen Thi Thanh , Nhiem Nguyen Xuan , Anh Hoang Le Tuan , Van Minh Chau , Van Kiem Phan
Published: March 2019

Two new steroidal glucosides, chantriolides D and E (1 and 2), along with four known compounds, chantriolide A (3), chantriolide B (4), chantriolide C (5), and (25 S)-spirost-5-en-3-ol 3- O-α-L-rhamnopyranosyl-(1→2)- O-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (6) were isolated from the rhizomes of Tacca chantrieri. Their structures were determined by 1D and 2D NMR spectroscopic and HR-ESI-MS data, as well as by comparison with reported data. Compounds 1 and 2 were found to show strong inhibitory NO effect in BV2 cells, with IC50 values of 12.45 and 59.03 μM, respectively.
Absolute Stereochemistry of the β-Hydroxy Acid Unit in Hantupeptins and Trungapeptins
Authors: Gupta Deepak Kumar , Ding Gary Chi Ying , Teo Yong Chua , Tan Lik Tong
Published: March 2019

The β-hydroxy/amino acid unit is a common structural feature of many bioactive marine cyanobacterial depsipeptides. In this study, the absolute stereochemistry of the β-hydroxy acid moieties in hantupeptins and trungapeptins were determined through their synthesis and HPLC analysis of the Mosher ester derivatives. Synthesis of two3-hydroxy-2-methyloctanoic acid (Hmoa) stereoisomers, (2 S,3 R)-Hmoa and (2 S,3 S)-Hmoa, were achieved using diastereoselective asymmetric method and the retention times of all four Hmoa isomers were established indirectly by RPLC-MS analysis of their Mosher ester derivative standards. Based on the retention times of the standards, the absolute configuration of the Hmoa unit in hantupeptin C (3) and trungapeptin C (6) was assigned as (2 R,3 S)- and (2 S,3 R)-Hmoa, respectively. The use of the Mosher's reagents, coupled with HPLC analysis, provided a viable alternative to the absolute stereochemical determination of β-hydroxy acid units in depsipeptides.
Acetophenones Isolated from Acronychia Pedunculata and their Anti-proliferative Activities
Authors: Ito Chihiro , Matsui Takuya , Ban Yoshiaki , Wu Tian-Shung , Itoigawa Masataka
Published: March 2019

Study of the chemical constituents of Acronychia pedunculata (L.) Miq. (Rutaceae) stems collected in Taiwan led to the isolation and identification of eight known and three new acetophenones, named acrophenone A (1), B (2), and C (3). Of them, acrovestone (5), acropyrone (6) and acrovestenol (7), which are dimer compounds, strikingly inhibited the proliferation of human leukemia cell lines.
Three New Oxidation Products Produced from Epigallocatechin-3-O-gallate and Epicatechin-3-O-gallate
Authors: Li Yan , Matsuo Yosuke , Saito Yoshinori , Tanaka Takashi
Published: March 2019

During chemical studies on uncharacterized black tea polyphenols, the enzymatic oxidation of a mixture of epigallocatechin-3- O-gallate (1) and epicatechin-3- O-gallate (2) was examined, and three new dimeric products together with six known catechin dimers were isolated. Two of the new compounds have tricyclo[5.2.2.02,6]undecane and tricyclo[5.2.1.02,6]decane carboxyl structures generated by oxidative coupling between two pyrogallol-B-rings of 1. Another new product was a dimer connected by a C-C bond between the B-ring of 1 and a galloyl group of 2.
Discovery of a Novel Diterpene in Brown Propolis from the State of Parana, Brazil
Authors: Tazawa Shigemi , Arai Yasuko , Hotta Sho , Mitsui Taichi , Nozaki Hiroshi , Ichihara Kenji
Published: March 2019

Propolis is a resinous substance collected by honeybees from certain plant sources. The components of propolis depend on the vegetation of the area in which apiculture is practiced. In Brazil, there are several types of propolis including ‘green,’ ‘red’ and ‘brown'. Brazilian brown propolis from the state of Parana characteristically includes diterpenes, and we discovered a novel clerodane diterpene, rel-(5 S,6 S,8 R,9 R,10 S,18 R,19 S)-18,19-epoxy-2-oxocleroda-3,12( E),14-triene-6,18,19-triol 18,19-diacetate 6-benzoate (3) and five known diterpenes (1, 2, 4, 5 and 6). The chemical structure of the novel diterpene 3 was determined using 1D- and 2D-NMR spectroscopic analyses. Furthermore, the activities of the isolated diterpenes on growth inhibition of several human cancer cell lines (LNCaP, MCF-7, DLD-1 and A549) were evaluated in vitro; diterpene 3 exhibited a potent inhibition of cell growth, and its activity was approximately 15 times higher than that of the other diterpenes.
Synthesis and Larvicidal Activity of Phrymarolin Derivatives against Culex Pipiens Pallens
Authors: Tan Fangfang , Zheng Shaojun , Gao Peng , Li Shengkun , Hu Zhaonong , Wu Wenjun , Zhang Jiwen
Published: March 2019

Twenty-eight new phrymarolin derivatives, including twenty-one ethers, six esters and a dehydroxy phrymarolin, were prepared from phrymarolin I and the structures of all the derivatives were confirmed by 1H NMR and 13C NMR spectroscopic and MS data analyses. Larvicidal activities of these phrymarolin analogues were assayed against 4th instar larvae of Culex pipiens pallens. The ester derivatives of phrymarolin showed lower larvicidal activity than phrymarolin I, but some of the ether derivatives and dehydroxy phrymarolin showed much higher activity. Two ether derivatives, 1–18 and 1–19, showed significant larvicidal activity with LC50 values of 1.89 and 7.78 mg/L, respectively.
An Unprecedented High Content of the Bioactive Flavone Tricin in Huperzia Medicinal Species Used by the Saraguro in Ecuador
Authors: Armijos Chabaco , Ponce Jorge , Ramírez Jorge , Gozzini Davide , Finzi Paola Vita , Vidari Giovanni
Published: March 2019

The flavone tricin (5,7,4′-trihydroxy-3′,5′-dimethoxyflavone) is considered to be a selective potent inhibitor of different cancer cell lines and a potential colorectal cancer chemopreventive agent. In this paper we describe a reliable UHPLC-UV-ESIMS method for the determination of tricin in Huperzia plants used in the traditional medicine of the Saraguro community living in Southern Ecuador. An unusually high amount of tricin was found in H. brevifolia and H. compacta, which exceeded the content of this flavone determined so far in other plants.
Effect of Three Centaurea Species Collected from Central Anatolia Region of Turkey on Human Melanoma Cells
Authors: Russo Alessandra , Cardile Venera , Graziano Adriana C.E. , Rigano Daniela , Aktumsek Abdurrahman , Zengin Gokhan , Senatore Felice
Published: March 2019

Centaurea is the largest genus within the Asteraceae family. Many members of this genus are used in traditional folk medicine, such as Centaurea pulchella used to treat skin problems such as to resolve the abscess. Although biological activities of many Centaurea species have been investigated in different countries and Turkey, cytotoxic effect of C. patula, C. pulchella and C. tchihatcheffii has not been studied yet. Melanoma is one of the most invasive and deadly forms of skin cancer. Therefore, in an ongoing effort to identify new natural anticancer products for the treatment and/or prevention of melanoma cancer, the present study was undertaken to investigate the effect of these Centaurea species, collected from Central Anatolia region of Turkey on cell growth and death in human melanoma cell line, A375. The results revealed that all extracts were able to inhibit, after 48 h of treatment, the growth of cancer cells, that could be related to an overall action of the phenolic compounds present. In fact, C. pulchella, with the highest level of phenolics, showed a major activity followed by C. patula and C. tchihatcheffii. Our data also demonstrate that these natural products induce apoptotic cell death. In conclusion, the study of plant extracts for their cytotoxic and apoptotic properties has shown that medicinal herbs from Centaurea species might have also importance in the prevention and treatment of melanoma.
Phenolic Compounds from the Fruits of Medemia argun, a Food and Medicinal Plant of Ancient Egypt
Authors: Masullo Milena , Hamed Arafa I. , Mahalel Usama A. , Pizza Cosimo , Piacente Sonia
Published: March 2019

Medemia argun is a mysterious and little known monotypic fan palm from the Nubian Desert Oases of southern Egypt and northern Sudan. Its fruits have been found in the tombs from the 5th Dynasty (ca. 2500 BC) to Roman times (6–7th century AD), including the celebrated tomb of Tutankhamun. In ancient Egypt, the fruits of this palm were widely distributed and were highly valued, as confirmed by their frequent occurrence in offerings in the tombs. İn order to elucidate the chemical composition of the phenolic fraction, phytochemical investigation of the BuOH extract of fruits was carried out to afford eight compounds (1–8), among which was the new 2,4-dihydroxy-6-methylacetophenone 2- O-β-D-glucopyranoside (1). With the aim to investigate if the high shelf life of M. argun fruits could be related to the occurrence of antioxidant principles that were able to prevent oxidative reactions, the evaluation was carried out of the in vitro antioxidant activity by Trolox equivalent antioxidant capacity (TEAC) assay of the extract and isolated compounds.
A Novel Alkaloid Isolated from Spiranthera Atlantica (Rutaceae)
Authors: Rocha Michelle Rodrigues e , Da Cunha Carolina Passos , Filho Raimundo Braz , Vieira Ivo J. Curcino
Published: March 2019

A novel alkaloid 3-hydroxy-4-(2-hydroxyethyl)-4′-methoxy-7′ H-quinolino[2,1- b]quinazolin-7′-one, named atlanticol (1), was isolated from Spiranthera atlantica (Rutaceae), along with five known compounds: lupeol (3), γ-fagarine (4), skimmianine (5), 7-methoxy-1-methyl-2-phenyl-4-quinolone (6) and 8-methoxy-1-methyl-2-phenyl-4-quinolone (7). Compound 6 was isolated from the Spiranthera genus for the first time. These compounds were characterized based on their spectral data, mainly through one and two-dimensional NMR and mass spectra, but also involving comparison with literature data.
A Novel Tirucallane-type Triterpene and Sesquiterpene from Trichilia maynasiana
Authors: D'Ambola Massimiliano , Malafronte Nicola , Gualtieri Maria , Hernández Vanessa , Vassallo Antonio , Severino Lorella
Published: March 2019

One new tirucallane-type triterpene {3β, 24-dihydroxytirucallan-7,25-diene, 24-sulfate (1)}, one new sesquiterpene {7- epi-10-hydroxychabrol-1(2)-en-4,5-dione A (2)}, together with three known tirucallanes, and four aromadendranes were isolated from the leaves of Trichlia maynasiana C. DC. Their structures were determined by means of NMR spectroscopy, mass spectrometric analysis, and chemical methods.
Effectiveness of 5-Pyrrolidone-2-carboxylic Acid and Copper Sulfate Pentahydrate Association against Drug Resistant Staphylococcus Strains
Authors: Governa Paolo , Miraldi Elisabetta , De Fina Gianna , Biagi Marco
Published: March 2019

Bacterial resistance is an ongoing challenge for pharmacotherapy and pharmaceutical chemistry. Staphylococcus aureus is the bacterial species which makes it most difficult to treat skin and soft tissue infections and it is seen in thousands of hospitalization cases each year. Severe but often underrated infectious diseases, such as complicated nasal infections, are primarily caused by MRSA and S. epidermidis too. With the aim of studying new drugs with antimicrobial activity and effectiveness on drug resistant Staphylococcus strains, our attention in this study was drawn on the activity of a new association between two natural products: 5-pyrrolidone-2-carboxylic acid (PCA), naturally produced by certain Lactobacillus species, and copper sulfate pentahydrate (CS). The antimicrobial susceptibility test was conducted taking into account 12 different Staphylococcus strains, comprising 6 clinical isolates and 6 resistant strains. PCA 4%, w/w, and CS 0.002%, w/w, association in distilled water solution was found to have bactericidal activity against all tested strains. Antimicrobial kinetics highlighted that PCA 4%, w/w, and CS 0.002% association could reduce by 5 log10 viable bacterial counts of MRSA and oxacillin resistant S. epidermidis in less than 5 and 3 minutes respectively. Microscopic investigations suggest a cell wall targeting mechanism of action. Being very safe and highly tolerated, the natural product PCA and CS association proved to be a promising antimicrobial agent to treat Staphylococcus related infections.
Effect of Selected Pyrazine Derivatives on the Production of Phenolics and Rutin in Urtica dioica and Fagopyrum esculentum
Authors: Moravcová Šárka , Fiedlerová Vendula , Tůma Jiří , Musil Karel , Tůmová Lenka
Published: March 2019

The effect of four pyrazine derivatives on the content of phenolic compounds in Urtica dioica L. and rutin in Fagopyrum esculentum Moench was studied. Pyrazine derivatives H1 and H2 were used on U. dioica, and derivatives S1 and S2 on F. esculentum, both separately and in combination with urea. The content of phenolic compounds in the stems of U. dioica after treatment with H2 at a concentration of 10−3 M significantly increased compared with the control and to a lower concentration of the same pyrazine derivative. In the case of S1 and S2 for F. esculentum, rutin content also increased in stems, mainly after treatment together with urea. By contrast, rutin and phenolics contents in the leaves did not change in comparison with controls after application of H1, H2, S1 and S2. Treatment with H1 and H2 in two chosen concentrations resulted in a significant increase in the net photosynthetic rate, transpiration rate and stomatal conductance. A slight increase in the rate of photosynthesis was observed also after application of variants of S1 and S1 with urea. Pyrazine derivatives did not show any effect on either the relative content of chlorophyll or chlorophyll fluorescence. A slight weight reduction of above ground biomass was shown only after application of S1 and S2. Dark necrosis on the edges and center of the leaves was observed in all treated plants after pyrazine application. The results suggest that all the pyrazine derivatives possess herbicidal effects.
HPLC-Guided Isolation, Purification and Characterization of Phenylpropanoid and Phenolic Constituents of Nutmeg Kernel (Myristica fragrans)
Authors: Chiu Sharon , Wang Thomas , Belski Martin , Abourashed Ehab A.
Published: March 2019

Many studies on the biological activities of nutmeg continue to appear in the literature. The most common targets include GIT, CNS, oxidative stress and inflammation. However, results obtained from most studies are often inconsistent due to the variability of utilized samples, lack of standardized nutmeg products or insufficient amounts of pure compounds for comprehensive follow-up investigation. To address the consistency and supply issue we utilized available technology to develop a reproducible procedure for preparation of specific extracts and isolation of the major phenolic constituents present in nutmeg kernel. A well-defined and reproducible sequence of extraction, fractionation and chromatographic purification was adopted and was guided by HPLC fingerprinting. Spectroscopic methods, mainly NMR, and mass spectrometry were utilized to identify each compound. Thirteen compounds were isolated in a pure form and identified as: elemicin (1), isoelemicin (2), myristicin (4), surinamensin (5), malabaricone C (6), 2-(3′-allyl-2′,6′-dimethoxy-phenyloxy)-1-acetoxy-(3,4-dimethoxyphenyl)-propyl ester (7), methoxylicarin A (8), licarin A (9), malabaricone B (10), licarin C (11), 5′-methoxylicarin B (12), licarin B (13), and 2-(3′-allyl-2′,6′-dimethoxy-phenyloxy)-1-methyl-5-methoxy-1,2-dihydrobenzofuran (3, a new compound). With repeated isolation runs, these pure compounds can be prepared in quantities sufficient for biological evaluation as needed. The availability of purified compounds will also allow the development of specific, accurate, and sensitive analytical procedures for pharmacokinetic studies and for quality control of nutmeg products. Both aspects are essential for nutmeg-focused drug discovery. The same approach can also be adapted to other medicinal plants of potential interest.
In Vitro and In Vivo Antiangiogenic Activity of Crowberry (Empetrum nigrum var. japonicum)
Authors: Bae Hong-Sook , Kim Hyun Ju , Jeong Da Hye , Hosoya Takahiro , Kumazawa Shigenori , Jun Mira , Kim Oh-Yoen , Kim Sun Wook , Ahn Mok-Ryeon
Published: March 2019

Crowberry, Empetrum nigrum var. japonicum, is widely used in folk medicine and grows naturally in Korea. Although some constituents and biological activity of Korean crowberry have been examined, there is little detailed information available. In this study, we investigated the effects of ethanol extracts of crowberry (EECB) on the inhibition of angiogenesis, both in vitro and in vivo. The effects of EECB were tested on in vitro models of angiogenesis, that is, tube formation and proliferation of human umbilical vein endothelial cells (HUVECs). EECB exhibited significant inhibitory effects on tube formation of HUVECs in a concentration-dependent manner. In addition, crowberry significantly suppressed the proliferation of HUVECs in a concentration-dependent manner. Furthermore, strong antiangiogenic activity of EECB samples was observed in the in vivo assay using chick embryo chorioallantoic membrane (CAM). These results indicate that crowberry may have potential applications in the prevention and treatment of angiogenesis-dependent human diseases.
Antimicrobial Activity and Chemical Analysis of the Essential Oil of Algerian Juniperus phoenicea
Authors: Bouyahyaoui Ahmed , Bahri Fouad , Romane Abderrahmane , Höferl Martina , Wanner Juergen , Schmidt Erich , Jirovetz Leopold
Published: March 2019

The essential oils of Juniperus phoenicea L. from Algeria were obtained by hydrodistillation and analyzed by GC-FID and GC-MS. Concerning their chemical composition, 74, 61 and 72 volatile compounds were identified from fresh leaves, dried leaves and berries, representing 88.8%, 91.3% and 94.7% of the total composition, respectively. The main monoterpene in the oils of fresh leaves, dried leaves and berries was α-pinene (29.6% / 55.9% / 56.6%), accompanied by lesser amounts of the sesquiterpenes β-caryophyllene (2.6% / 1.6% /1.2%) and germacrene D (2.01% / 1.7% / 1.5%), respectively. Antibacterial activity of J. phoenicea essential oils was tested against one Gram-negative and four Gram-positive bacterial strains and the yeast Candida albicans, responsible for nosocomial infections. As references, 14 antibiotics and 5 antifungal agents were evaluated. The berry essential oil was ineffective against all but two of the strains tested, whereas the essential oil of dried leaves significantly inhibited all strains but Pseudomonas aeruginosa, which turned out to be the most resistant strain overall. However, Escherichia coli was the most susceptible to the essential oils tested. The essential oil of dry leaves was highly active against Candida albicans, outclassing even the standard antifungal substances. These promising results could substantiate the use of essential oils in the treatment of hospital-acquired infections.