Antiprotozoal Diterpenes from Perovskia abrotanoides

Planta Medica ◽  
2018 ◽  
Vol 84 (12/13) ◽  
pp. 913-919 ◽  
Author(s):  
Marzieh Tabefam ◽  
Mahdi Farimani ◽  
Ombeline Danton ◽  
Justine Ramseyer ◽  
Marcel Kaiser ◽  
...  
Keyword(s):  
High Performance ◽  
Leishmania Donovani ◽  
Ionization Mass ◽  
Trypanosoma Brucei Rhodesiense ◽  
Selective Toxicity ◽  
L6 Cells ◽  
Aerial Parts ◽  
New Compounds ◽  
Perovskia Abrotanoides ◽  
Ethyl Acetate Extracts

AbstractAs part of a screening for new antiparasitic natural products from Iranian plants, n-hexane and ethyl acetate extracts from the aerial parts of Perovskia abrotanoides were found to exhibit strong inhibitory activity against Trypanosoma brucei rhodesiense and Leishmania donovani. The activity was tracked by high-performance liquid chromatography (HPLC)-based activity profiling. Preparative isolation by a combination of silica gel column chromatography and HPLC afforded 17 diterpenoids (1–17), including 14 abietane-, two icetexane-, and one isopimarane-type derivatives. Among these, (5R,10S)-11-hydroxy-12-methoxy-20-norabieta-8,11,13-triene (2), 12-hydroxy-norabieta-1(10),8,11,13-tetraene-1,11-furan (6), and 12-methoxybarbatusol (9) were new compounds, the structure of which was established by comprehensive spectroscopic data analysis (one- and two-dimensional nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, electronic circular dichroism). The antiprotozoal activity of the isolated compounds was evaluated against T. b. rhodesiense, Trypanosoma cruzi, L. donovani, and Plasmodium falciparum. Selectivity indexes (SI) were calculated in comparison to cytotoxicity on rat myoblast (L6) cells. Particularly active were 7α-ethoxyrosmanol (4) with an IC50 of 0.8 µM against T. b. rhodesiense (SI 14.9) and an IC50 of 1.8 µM (SI 6.9) against L. donovani, ferruginol (8) with an IC50 of 2.9 µM (SI 19.2) against P. falciparum, and miltiodiol (10) with an IC50 of 0.5 µM (SI 10.5) against T. b. rhodesiense. None of the compounds exhibited selective toxicity against T. cruzi (SI ≤ 1.6).

scholarly journals Unusual derivatives from Hypericum scabrum

2020 ◽  
Vol 10 (1) ◽  
Author(s):  
Sara Soroury ◽  
Mostafa Alilou ◽  
Thomas Gelbrich ◽  
Marzieh Tabefam ◽  
Ombeline Danton ◽  
...  
Keyword(s):  
Trypanosoma Brucei ◽  
2D Nmr ◽  
Moderate Activity ◽  
Trypanosoma Brucei Rhodesiense ◽  
L6 Cells ◽  
Aerial Parts ◽  
Hypericum Scabrum ◽  
New Compounds ◽  
Absolute Structure

AbstractThree new compounds (1–3) with unusual skeletons were isolated from the n-hexane extract of the air-dried aerial parts of Hypericum scabrum. Compound 1 represents the first example of an esterified polycyclic polyprenylated acylphloroglucinol that features a unique tricyclo-[4.3.1.11,4]-undecane skeleton. Compound 2 is a fairly simple MPAP, but with an unexpected cycloheptane ring decorated with prenyl substituents, and compound 3 has an unusual 5,5-spiroketal lactone core. Their structures were determined by extensive spectroscopic and spectrometric techniques (1D and 2D NMR, HRESI-TOFMS). Absolute configurations were established by ECD calculations, and the absolute structure of 2 was confirmed by a single crystal determination. Plausible biogenetic pathways of compounds 1–3 were also proposed. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and Plasmodium falciparum and cytotoxicity against rat myoblast (L6) cells were determined. Compound 1 showed a moderate activity against T. brucei and P. falciparum, with IC50 values of 3.07 and 2.25 μM, respectively.

scholarly journals In vitro Antiprotozoal Activity of Extracts of five Turkish Lamiaceae Species

2011 ◽  
Vol 6 (11) ◽  
pp. 1934578X1100601 ◽  
Author(s):  
Hasan Kirmizibekmez ◽  
Irem Atay ◽  
Marcel Kaiser ◽  
Erdem Yesilada ◽  
Deniz Tasdemir
Keyword(s):  
Trypanosoma Brucei ◽  
Leishmania Donovani ◽  
Hexane Extract ◽  
Significant Activity ◽  
Trypanosoma Brucei Rhodesiense ◽  
L6 Cells ◽  
Methanolic Extracts ◽  
Aerial Parts ◽  
Organic Extracts

The in vitro antiprotozoal activities of crude methanolic extracts from the aerial parts of five Lamiaceae plants ( Salvia tomentosa, S. sclarea, S. dichroantha, Nepeta nuda subsp. nuda and Marrubium astracanicum subsp. macrodon) were evaluated against four parasitic protozoa, i.e. Trypanosoma brucei rhodesiense, T. cruzi, Leishmania donovani and Plasmodium falciparum. The cytotoxic potentials of the extracts on L6 cells were also evaluated. Melarsoprol, benznidazole, miltefosine, chloroquine and podophyllotoxin were used as reference drugs. All crude MeOH extracts showed antiprotozoal potential against at least three parasites, so they were dispersed in water and partitioned against n-hexane and chloroform to yield three subextracts that were screened in the same test systems. The n-hexane extract of N. nuda was the most active against T. brucei rhodesiense while the CHCl3 extracts of S. tomentosa and S. dichroantha showed significant activity against L. donovani. All organic extracts displayed in vitro antimalarial and moderate trypanocidal activities against T. cruzi with the n-hexane extract of S. sclarea being the most active against the latter. The extracts displayed low or no cytotoxicity towards mammalian L6 cells.

scholarly journals Comparison of the Qualitative Chemical Composition of Extracts from Ageratina havanensis Collected in Two Different Phenological Stages by FIA-ESI-IT-MSn and UPLC/ESI-MSn: Antiviral Activity

2017 ◽  
Vol 12 (1) ◽  
pp. 1934578X1701200 ◽  
Author(s):  
Trina H. García ◽  
Claudia Quintino da Rocha ◽  
Marcelo J. Dias ◽  
Liudis L. Pino ◽  
Gloria del Barrio ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Chemical Composition ◽  
Antiviral Activity ◽  
Ethyl Acetate ◽  
High Performance ◽  
Ethyl Acetate Extract ◽  
Reproductive Season ◽  
Ionization Mass ◽  
Herpes Simplex Viruses ◽  
Ethyl Acetate Extracts

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

scholarly journals Antiprotozoal Germacranolide Sesquiterpene Lactones from Tanacetum sonbolii

Planta Medica ◽  
2019 ◽  
Vol 85 (05) ◽  
pp. 424-430 ◽  
Author(s):  
Sahar Mofidi Tabatabaei ◽  
Samad Nejad Ebrahimi ◽  
Peyman Salehi ◽  
Ali Sonboli ◽  
Marzieh Tabefam ◽  
...  
Keyword(s):  
Trypanosoma Brucei ◽  
High Resolution Mass Spectrometry ◽  
Sesquiterpene Lactones ◽  
Resonance Spectroscopy ◽  
Trypanosoma Brucei Rhodesiense ◽  
L6 Cells ◽  
Aerial Parts ◽  
Phytochemical Investigation ◽  
Ic50 Values

AbstractA phytochemical investigation of extracts from flowers and aerial parts of Tanacetum sonbolii afforded 7 new germacranolide sesquiterpene lactones. The structures were established by a combination of 1- and 2-dimensional nuclear magnetic resonance spectroscopy, high-resolution mass spectrometry, and electronic circular dichroism. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and cytotoxicity against rat myoblast (L6) cells were determined. Compounds 4 and 5 showed IC50 values of 5.1 and 10.2 µM and selectivity indices of 3.9 and 4.0, respectively.

scholarly journals ELECTROSPRAY IONIZATION MASS SPECTROMETRY FRAGMENTATION PATHWAYS OF SALTS OF SOME 1,2,4-TRIAZOLYLTHIOACETATE ACIDS, THE ACTIVE PHARMACEUTICAL INGREDIENTS

2018 ◽  
Vol 11 (10) ◽  
pp. 303
Author(s):  
Varynskyi Borys ◽  
Kaplaushenko Andriy ◽  
Parchenko Vladymyr
Keyword(s):  
Electrospray Ionization ◽  
High Performance ◽  
Pharmaceutical Formulations ◽  
Ionization Mass ◽  
Active Pharmaceutical Ingredients ◽  
Ionization Source ◽  
Fragmentation Pathways ◽  
Pharmaceutical Ingredients ◽  
Fragmentation Patterns ◽  
New Compounds

Objective: The goal of this research was to study fragmentation pathways of series salts of 1,2,4-triazolylthioacetate acids. Methods: The study was done in the Electrospray ionization source with single quadrupole mass spectrometer Agilent 6120 after elution through column Zorbax SB-C18, 30 mm × 4.6 mm, 1.8 μm at Agilent 1260 infinity high-performance liquid chromatography system. The series salts of 1,2,4-triazolylthioacetate acids were studied. These salts are active pharmaceutical ingredients of potential or registered pharmaceutical formulations. Results: The mass spectra of corresponding compounds have analyzed. The fragmentation patterns of these compounds decay have proposed. Conclusions: Studying the fragmentation of the indicated substances can be used for detecting the mentioned substances, as well as for confirming the structure of new compounds with the mass spectrum based on the patterns described above.

scholarly journals Antileishmanial Activity of Flavones-Rich Fraction From Arrabidaea chica Verlot (Bignoniaceae)

2021 ◽  
Vol 12 ◽  
Author(s):  
João Victor Silva-Silva ◽  
Carla Junqueira Moragas-Tellis ◽  
Maria do Socorro dos Santos Chagas ◽  
Paulo Victor Ramos de Souza ◽  
Celeste da Silva Freitas de Souza ◽  
...  
Keyword(s):  
High Performance ◽  
Peritoneal Macrophages ◽  
Ultrastructural Changes ◽  
Ionization Mass ◽  
Griess Reagent ◽  
Transmission Electron ◽  
Arrabidaea Chica ◽  
New Compounds ◽  
Hydroethanolic Extract

Acknowledging the need of identifying new compounds for the treatment of leishmaniasis, this study aimed to evaluate, from in vitro trials, the activity of flavones from Arrabidaea chica against L. amazonensis. The chromatographic profiles of the hydroethanolic extract and a flavone-rich fraction (ACFF) from A. chica were determined by high-performance liquid chromatography coupled with a diode-array UV-Vis detector (HPLC-DAD-UV) and electrospray ionization mass spectrometry in tandem (LC-ESI-MS-MS). The flavones luteolin (1) and apigenin (2), isolated from chromatographic techniques and identified by Nuclear Magnetic Resonance of 1H and 13C, were also quantified in ACFF, showing 190.7 mg/g and apigenin 12.4 mg/g, respectively. The other flavones were identified by comparing their spectroscopic data with those of the literature. The in vitro activity was assayed against promastigotes and intramacrophagic amastigote forms of L. amazonensis. Cytotoxicity tests were performed with peritoneal macrophages of BALB/c mice. Nitrite quantification was performed with Griess reagent. Ultrastructural investigations were obtained by transmission electron microscopy. Anti-Leishmania assays indicated that the IC50 values for ACFF, apigenin, and luteolin were obtained at 40.42 ± 0.10 and 31.51 ± 1.13 μg/mL against promastigotes, respectively. ACFF and luteolin have concentration-dependent cytotoxicity. ACFF and luteolin also inhibited the intra-macrophagic parasite (IC50 3.575 ± 1.13 and 11.78 ± 1.24 μg/mL, respectively), with a selectivity index of 11.44 for ACFF. Promastigotes exposed to ACFF and luteolin exhibited ultrastructural changes, such as intense cytoplasm vacuolization and mitochondrial swelling. These findings data evidence the antileishmanial action of flavone-rich fractions of A. chica against L. amazonensis, encouraging further studies.

scholarly journals Cinnamoylphenethyl Amides from Polygonum hyrcanicum Possess Anti-Trypanosomal Activity

2012 ◽  
Vol 7 (6) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Fahimeh Moradi-Afrapoli ◽  
Nargues Yassa ◽  
Stefanie Zimmermann ◽  
Soodabeh Saeidnia ◽  
Abbas Hadjiakhoondi ◽  
...  
Keyword(s):  
Ferulic Acid ◽  
Trypanosoma Brucei ◽  
Methanolic Extract ◽  
Coumaric Acid ◽  
Trypanosoma Brucei Rhodesiense ◽  
Active Compounds ◽  
Active Constituents ◽  
L6 Cells ◽  
Aerial Parts ◽  
Bioassay Guided Fractionation

A methanolic extract from aerial parts of Polygonum hyrcanicum (Polygonaceae) showed high activity against Trypanosoma brucei rhodesiense (IC50=3.7 μg/mL). Bioassay-guided fractionation of the extract resulted in isolation of cinnamoylphenethyl amides, including N-trans-caffeoyltyramine (1), N-trans-p-coumaroyltyramine (7), and N-trans-feruloyltyramine (8) as the main active constituents (IC50s ranging from 2.2 to 13.3 μM). Some structurally related, but less active compounds, such as cannabisin B (2), tyrosol (3), p-coumaric acid (4), ferulic acid (5), and N-cis-feruloyltyramine (6) were also identified, along with N-trans-3,4-dimethoxycinnamoyldopamine (9). Cytotoxicity of the active compounds in L6 cells was determined, and selectivity indices (SI) of 7.9 to 33.4 were calculated.

scholarly journals New Antifungal Metabolites from the Mariana Trench Sediment-Associated Actinomycete Streptomyces sp. SY1965

Marine Drugs ◽  
2020 ◽  
Vol 18 (8) ◽  
pp. 385 ◽  
Author(s):  
Wenwen Yi ◽  
Le Qin ◽  
Xiao-Yuan Lian ◽  
Zhizhen Zhang
Keyword(s):  
High Performance ◽  
Nuclear Overhauser Effect ◽  
Ionization Mass ◽  
Mariana Trench ◽  
Streptomyces Sp ◽  
Antifungal Metabolites ◽  
Ionization Mass Spectroscopy ◽  
Noesy Experiment ◽  
Nuclear Overhauser ◽  
New Compounds

New streptothiazolidine A (1), streptodiketopiperazines A (2) and B (3), and (S)-1-(3-ethylphenyl)-1,2-ethanediol (4), together with eight known compounds (5–12), were isolated from the Mariana Trench sediment-associated actinomycete Streptomyces sp. SY1965. The racemic mixtures of (±)-streptodiketopiperazine (2 and 3) and (±)-1-(3-ethylphenyl)-1,2-ethanediol (4 and 5) were separated on a chiral high-performance liquid chromatography (HPLC) column. Structures of the new compounds were elucidated by their high-resolution electrospray ionization mass spectroscopy (HRESIMS) data and extensive nuclear magnetic resonance (NMR) spectroscopic analyses. Streptothiazolidine A is a novel salicylamide analogue with a unique thiazolidine-contained side chain and its absolute configuration was established by a combination of nuclear Overhauser effect spectroscopy (NOESY) experiment, electronic circular dichroism (ECD) and 13C NMR calculations. New streptothiazolidine A (1) and streptodiketopiperazines A (2) and B (3) showed antifungal activity against Candida albicans with MIC values of 47, 42, and 42 g/mL, respectively.

scholarly journals Metabolomics and DNA-Based Authentication of Two Traditional Asian Medicinal and Aromatic Species of Salvia subg. Perovskia

Cells ◽  
2021 ◽  
Vol 10 (1) ◽  
pp. 112
Author(s):  
Monika Bielecka ◽  
Bartosz Pencakowski ◽  
Marta Stafiniak ◽  
Klemens Jakubowski ◽  
Mehdi Rahimmalek ◽  
...  
Keyword(s):  
Dna Barcoding ◽  
High Performance ◽  
Carnosic Acid ◽  
Limited Information ◽  
Metabolomic Analysis ◽  
Separate Species ◽  
Flight Mass Spectrometry ◽  
Aerial Parts ◽  
Central Asian ◽  
Aromatic Species

Subgenus Perovskia of the extended genus of Salvia comprises several Central Asian medicinal and aromatic species, of which S. yangii and S. abrotanoides are the most widespread. These plants are cultivated in Europe as robust ornamentals, and several cultivars are available. However, their medicinal potential remains underutilized because of limited information about their phytochemical and genetic diversity. Thus, we combined an ultra-high performance liquid chromatography quadrupole time of flight mass spectrometry (UHPLC-QTOF-MS) based metabolomics with DNA barcoding approach based on trnH-psbA and ITS2 barcodes to clarify the relationships between these two taxa. Metabolomic analysis demonstrated that aerial parts are more similar than roots and none of the major compounds stand out as distinct. Sugiol in S. yangii leaves and carnosic acid quinone in S. abrotanoides were mostly responsible for their chemical differentiation, whereas in roots the distinction was supported by the presence of five norditerpenoids in S. yangii and two flavonoids and one norditerpenoid in S. abrotanoides. To verify the metabolomics-based differentiation, we performed DNA authentication that revealed S. yangii and S. abrotanoides to be very closely related but separate species. We demonstrated that DNA barcoding coupled with parallel LC-MS profiling constitutes a powerful tool in identification of taxonomically close Salvia species.

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