Salaterpene E, a eudesmane-type sesquiterpene from Salacia longipes var. camerunensis

2016 ◽  
Vol 71 (2) ◽  
pp. 87-93 ◽  
Author(s):  
Brice Mittérant Mba’ning ◽  
Bruno Lenta Ndjakou ◽  
Ferdinand Mouafo Talontsi ◽  
Alain Meli Lannang ◽  
Birger Dittrich ◽  
...  
Keyword(s):  
Plasmodium Falciparum ◽  
Absolute Configuration ◽  
Previous Investigation ◽  
Spectroscopic Analysis ◽  
Inhibitory Concentration ◽  
Anomalous Scattering ◽  
X Ray Diffraction ◽  
Meoh Extract ◽  
X Ray

AbstractA mixture of two compounds with potent antiplasmodial activity in vitro against the W2 strain of Plasmodium falciparum (half maximal inhibitory concentration, 1.12 μg/mL) was obtained in a previous investigation of the CH2Cl2-MeOH extract of the seeds of Salacia longipes var. camerunensis. Separation by column chromatography led now to the isolation of salaterpene E (1) and (1R,2R,4S,5S,6R,7R,9S,10R)-2-acetoxy-1,6,9-tribenzoyloxy-4-hydroxy-dihydro-β-agarofuran (2). The structure of 1 was elucidated by spectroscopic analysis, and its absolute configuration was established unambiguously by means of single-crystal X-ray diffraction. Also the absolute configurations of the recently described salaterpenes A (2a) and D (2b) were determined by this method using the anomalous scattering of the oxygen atoms only.

scholarly journals Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

2019 ◽  
Vol 15 ◽  
pp. 2631-2643 ◽  
Author(s):  
Heather J Lacey ◽  
Cameron L M Gilchrist ◽  
Andrew Crombie ◽  
John A Kalaitzis ◽  
Daniel Vuong ◽  
...  
Keyword(s):  
Mammalian Cells ◽  
Biosynthetic Pathway ◽  
Spectroscopic Analysis ◽  
Bioinformatics Analysis ◽  
Biosynthetic Gene Cluster ◽  
In Vitro Activity ◽  
X Ray Diffraction ◽  
X Ray ◽  
Drimane Sesquiterpenoids

Chemical investigation of an undescribed Australian fungus, Aspergillus nanangensis, led to the identification of the nanangenines – a family of seven new and three previously reported drimane sesquiterpenoids. The structures of the nanangenines were elucidated by detailed spectroscopic analysis supported by single crystal X-ray diffraction studies. The compounds were assayed for in vitro activity against bacteria, fungi, mammalian cells and plants. Bioinformatics analysis, including comparative analysis with other acyl drimenol-producing Aspergilli, led to the identification of a putative nanangenine biosynthetic gene cluster that corresponds to the proposed biosynthetic pathway for nanangenines.

scholarly journals Anti-inflammatory Anthraquinones from the Crinoid Himerometra magnipinna

2015 ◽  
Vol 10 (2) ◽  
pp. 1934578X1501000
Author(s):  
Yen-You Lin ◽  
Su-June Tsai ◽  
Michael Y. Chiang ◽  
Zhi-Hong Wen ◽  
Jui-Hsin Su
Keyword(s):  
Single Crystal ◽  
Diffraction Analysis ◽  
Absolute Configuration ◽  
Spectroscopic Data ◽  
Test Compound ◽  
X Ray Diffraction ◽  
X Ray ◽  
Anti Inflammatory ◽  
Raw264.7 Macrophage

Chemical investigation of a crinoid Himerometra magnipinna has afforded three anthraquinones (1–3), including one new metabolite, (+)-rhodoptilometrin (1). The structures of these compounds were elucidated on the basis of their spectroscopic data and the absolute configuration of 1 was further confirmed by single-crystal X-ray diffraction analysis. In the in vitro anti-inflammatory effects test, compound 2 was found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein of the LPS-stimulated RAW264.7 macrophage cells.

scholarly journals Synthesis, In Vitro Screening and Docking Studies of New Thiosemicarbazide Derivatives as Antitubercular Agents

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 251 ◽  
Author(s):  
Monika Pitucha ◽  
Zbigniew Karczmarzyk ◽  
Marta Swatko-Ossor ◽  
Waldemar Wysocki ◽  
Maciej Wos ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Inhibitory Concentration ◽  
Acid Hydrazide ◽  
Docking Studies ◽  
Molecular Structures ◽  
Conformational Preference ◽  
X Ray ◽  
Carboxylic Acid Hydrazide ◽  
Thiosemicarbazide Derivatives

A series of thiosemicarbazide derivatives was designed and synthesized by reaction of carboxylic acid hydrazide with isothiocyanates. The molecular structures of the investigated thiosemicarbazides were confirmed and characterized by spectroscopic analysis. The conformational preference of carbonylthiosemicarbazide chain and intra- and intermolecular interactions in the crystalline state were characterized using X-ray analysis. The antituberculosis activity of the target compounds were tested in vitro against four Mycobacterium strains: M. H37Ra, M. phlei, M. smegmatis, M. timereck. The most active compounds were those with 2-pyridine ring. They exhibited lower minimal inhibitory concentration (MIC) values in the range 7.81–31.25 μg/mL in comparison to the other isomers. Compound 5 had activity against M. smegmatis at a concentration of 7.81 μg/mL whereas compound 2 had activity against all tested strains at a concentration of 15.625 μg/mL. The molecular docking studies were performed for investigated compounds using the Mycobacterium tuberculosis glutamine synthetase MtGS as their molecular target.

scholarly journals Host-guest interaction and properties of cucurbit[8]uril with chloramphenicol

2021 ◽  
Author(s):  
Lin Zhang ◽  
Jun Zheng ◽  
Guangyan Luo ◽  
Xiaoyue Li ◽  
Yunqian Zhang ◽  
...  
Keyword(s):  
Inhibitory Concentration ◽  
Slow Release ◽  
In Vitro Release ◽  
Titration Calorimetry ◽  
X Ray Diffraction ◽  
X Ray ◽  
E Coli ◽  
The Stability ◽  
Vitro Release

The interaction between cucurbit[8]uril (Q[8]) and chloramphenicol (CPE) was investigated using single-crystal X-ray diffraction, spectroscopy, isothermal titration calorimetry (ITC) and UV-Vis, NMR and IR spectroscopy. The effects of Q[8] on the stability, in vitro release performance and antibacterial activity of CPE were also studied. The results showed that CPE and Q[8] formed a 1:1 inclusion complex (CPE@Q[8]) with an inclusion constant of 5.4736 × 105 L/mol. The intervention of Q[8] did not affect the stability of CPE, but obviously reduced the release rate of CPE in artificial gastric and intestinal juice; Q[8] has a slow-release effect on CPE. The antibacterial results showed that the minimum inhibitory concentration (MIC) of CPE and CPE@Q[8] toward Escherichia coli (E. coli) was 1.5 × 10–3 and 1.0 × 10–3 mol/L, respectively, and toward Staphylococcus aureus (SA), the MIC was 2.0 × 10–3 mol/L for both CPE and CPE@Q[8]. Therefore, Q[8] enhanced the inhibitory activity of CPE against E. coli.

scholarly journals Biosynthesis of Silver Nanoparticles by Aspergillus terreus: Characterization, Optimization, and Biological Activities

2021 ◽  
Vol 9 ◽  
Author(s):  
Walid A. Lotfy ◽  
Basma M. Alkersh ◽  
Soraya A. Sabry ◽  
Hanan A. Ghozlan
Keyword(s):  
Silver Nanoparticles ◽  
Aspergillus Terreus ◽  
Inhibitory Concentration ◽  
Biological Activities ◽  
Antagonistic Activity ◽  
Metallic Silver ◽  
X Ray Diffraction ◽  
X Ray ◽  
Transmission Electron

In this study, mycelial filtrate of Aspergillus terreus BA6 was used to reduce AgNO3 to form silver nanoparticles (AgNPs). The effect of seven independent variables on the diameter of AgNPs was studied by applying design of experiments (DOE). At optimal conditions, the diameter of AgNPs was reduced by approximately 26.7% compared to the basal culture condition and AgNO3 concentration was found to be the most significant factor affecting the diameter of AgNPs. A. terreus nano-Ag was characterized using UV-visible spectroscopy, transmission electron microscopy, energy dispersive X-ray (EDX), X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), and Zeta potential. The maximum UV absorption was obtained at 420 nm and the microscopic results showed particles with narrow size distribution ranging from 7 to 23 nm. XRD pattern of AgNPs revealed four diffraction peaks of metallic silver and the EDX spectrum showed a strong signal attributed to Ag nano-crystals. AgNPs mycofabricated by A. terreus showed potent minimum inhibitory concentration (MIC) and broad minimum bactericidal/fungicidal concentration (MBC/MFC) against 12 reference microorganisms. The MIC and MBC/MFC values of AgNPs were 0.312 to 1.25 μg/ml and 0.625 to 10 μg/ml, respectively. Nevertheless, AgNPs did not demonstrate any antagonistic activity against Coxsackie B virus. The in vitro cytotoxicity of the mycosynthesized AgNPs showed significant antitumor activity against adenocarcinoma epithelial cells from human breast cancer (Mcf-7) cell line with an inhibitory concentration (IC50) of 87.5 μg/ml.

scholarly journals New 18(4→3)-Abeo-Abietanoids from Tripterygium wilfordii

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2467
Author(s):  
Lin Ni ◽  
Ying-da Zang ◽  
Jing-zhi Yang ◽  
Chuang-jun Li ◽  
Jie Ma ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Crystallographic Analysis ◽  
No Production ◽  
Anomalous Scattering ◽  
Tripterygium Wilfordii ◽  
Raw 264.7 Macrophages ◽  
X Ray ◽  
Inhibitory Activities ◽  
New Compounds

Three 18(4→3)-abeo-abietanoids, a new natural product and two new compounds, named tripordolides A–C (1–3), were isolated from the leaves of Tripterygium wilfordii. Their structures were elucidated on the basis of their spectroscopic analysis, and the absolute configuration of compounds was confirmed by CD and X-ray crystallographic analysis using anomalous scattering of Cu Kα radiation. Compounds 1 and 3 showed moderate inhibitory activities against NO production in lipopolysaccharide-induced (LPS) RAW 264.7 macrophages in vitro.

scholarly journals Host–guest interaction and properties of cucurbit[8]uril with chloramphenicol

2021 ◽  
Vol 17 ◽  
pp. 2832-2839
Author(s):  
Lin Zhang ◽  
Jun Zheng ◽  
Guangyan Luo ◽  
Xiaoyue Li ◽  
Yunqian Zhang ◽  
...  
Keyword(s):  
Inhibitory Concentration ◽  
Slow Release ◽  
In Vitro Release ◽  
Titration Calorimetry ◽  
X Ray Diffraction ◽  
X Ray ◽  
E Coli ◽  
The Stability ◽  
Vitro Release

The interaction between cucurbit[8]uril (Q[8]) and chloramphenicol (CPE) was investigated using single-crystal X-ray diffraction spectroscopy, isothermal titration calorimetry (ITC) and UV–vis, NMR and IR spectroscopy. The effects of Q[8] on the stability, in vitro release performance and antibacterial activity of CPE were also studied. The results showed that CPE and Q[8] formed a 1:1 inclusion complex (CPE@Q[8]) with an inclusion constant of 5.474 × 105 L/mol. The intervention of Q[8] did not affect the stability of CPE, but obviously reduced the release rate of CPE in artificial gastric and intestinal juice; Q[8] has a slow-release effect on CPE. The antibacterial results showed that the minimum inhibitory concentration (MIC) of CPE and CPE@Q[8] toward Escherichia coli (E. coli) was 1.5 × 10–3 and 1.0 × 10–3 mol/L, respectively, and toward Staphylococcus aureus (S. aureus), the MIC was 2.0 × 10–3 mol/L for both CPE and CPE@Q[8]. Therefore, Q[8] enhanced the inhibitory activity of CPE against E. coli.

scholarly journals Antidiarrheal Thymol Derivatives from Ageratina glabrata. Structure and Absolute Configuration of 10-Benzoyloxy-8,9-epoxy-6-hydroxythymol Isobutyrate

2016 ◽  
Author(s):  
Celia Bustos-Brito ◽  
Valeria J. Vázquez-Heredia ◽  
Fernando Calzada ◽  
Lilian Yépez-Mulia ◽  
José S. Calderón ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
13C Nmr ◽  
X Ray Diffraction ◽  
1H And 13C Nmr ◽  
X Ray ◽  
Thymol Derivatives ◽  
Nmr Data ◽  
Antiamoebic Activity ◽  
Positive Controls

Abstract: Chemical investigation of the leaves from Ageratina glabrata yielded four new thymol derivatives, namely: 10-Benzoyloxy-8,9-dehydro-6-hydroxythymol isobutyrate (4), 10-benzoyloxy-8,9-dehydro thymol (5), 10-benzoyloxythymol (6) and 10-benzoyloxy-6,8-dihydroxy-9-isobutyryloxythymol (7). In addition, (8S)-10-benzoyloxy-8,9-epoxy-6-hydroxythymol isobutyrate (1), together with other two already known thymol derivatives identified as: 10-benzoyloxy-8,9-epoxy-6-methoxythymol isobutyrate (2) and 10-benzoyloxy-8,9-epoxythymol isobutyrate (3). In this paper, we wish to publish the structures and complete assignments of 1H and 13C NMR data of compounds 1 – 7, and the absolute configuration for compound 1, unambiguously established by single crystal X-ray diffraction, and evaluation of the Flack parameter. The in vitro antiprotozoal assay showed that compound 1 and its derivative 1a were the most potent antiamoebic and antigiardial compounds. Both compounds showed selectivity and good antiamoebic activity like emetine and metronidazole, respectively, two antiprotozoal drugs used as positive controls. In relation of anti-propulsive effect, compound 1 and 1a showed moderate inhibitory activity, their activities were comparable to quercetin and compound 9, respectively, two natural antipropulsive compounds used as positive controls. These data suggest that compound 1 may play an important role in antidiarrheal properties of Ageratina glabrata.

A New Purine Derivative from the Roots of Phyllanthus flexuosus

2018 ◽  
Vol 13 (1) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Guanlin Zhu ◽  
Hongying Wang ◽  
Kunrong Gan ◽  
Heng Gao ◽  
Wei Li
Keyword(s):  
Spectroscopic Analysis ◽  
Carcinoma Cell ◽  
Inhibitory Effect ◽  
X Ray Diffraction ◽  
Purine Derivative ◽  
X Ray ◽  
Carcinoma Cell Lines ◽  
Human Hepatocellular Carcinoma Cell ◽  
Different Levels

A new purine derivative, 1-methyl-3-isopentenylisoguanine (1), together with six known compounds (2-7), was isolated from the roots of Phyllanthus flexuosus. The newly isolated structure was established by means of extensive spectroscopic analysis and single-crystal X-ray diffraction experiment. All isolates were evaluated for their in vitro cytotoxicities against two human hepatocellular carcinoma cell lines (HepG2 and SMMC-7721) by CCK-8 assays. Among them, three cleistanthane diterpenes (2–4) exhibited different levels of cytotoxicities against these cells with IC50 values ranging from 27.34 to 53.28 μM. Furthermore, acetylcholinesterase inhibitory effect for the new purine derivative was also assessed.

scholarly journals 8-Hydroxybriaranes from Octocoral Briareum stechei (Briareidae) (Kükenthal, 1908)

Marine Drugs ◽  
2021 ◽  
Vol 19 (3) ◽  
pp. 136
Author(s):  
Thanh-Hao Huynh ◽  
Su-Ying Chien ◽  
Junichi Tanaka ◽  
Zhi-Hong Wen ◽  
Yang-Chang Wu ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Nitric Oxide Synthase ◽  
Diffraction Analysis ◽  
Inducible Nitric Oxide Synthase ◽  
Absolute Configuration ◽  
Spectroscopic Analysis ◽  
X Ray Diffraction ◽  
X Ray ◽  
Oxide Synthase ◽  
Inducible Nitric Oxide

Chemical investigation of the octocoral Briareum stechei, collected in the Ie Island, Okinawa, Japan, resulted in the isolation of a new briarane-type diterpenoid, briastecholide A (1), as well as the previously reported metabolites, solenolide C (2) and briarenolide S (3). The structures of briaranes 1–3 were characterized through spectroscopic analysis, and the absolute configuration of 2 was corroborated by a single-crystal X-ray diffraction analysis. Briarane 3 exhibited bioactivity against the protein expression of inducible nitric oxide synthase (iNOS).

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