scholarly journals The Alkaloid-Enriched Fraction of Pachysandra terminalis (Buxaceae) Shows Prominent Activity against Trypanosoma brucei rhodesiense

Molecules ◽  
2021 ◽  
Vol 26 (3) ◽  
pp. 591
Author(s):  
Dagmar Flittner ◽  
Marcel Kaiser ◽  
Pascal Mäser ◽  
Norberto P. Lopes ◽  
Thomas J. Schmidt
Keyword(s):  
Trypanosoma Brucei ◽  
Trypanosoma Brucei Rhodesiense ◽  
Acid Base ◽  
Mass Spectral Fragmentation ◽  
Mass Spectral ◽  
Regression Modelling ◽  
Aerial Parts ◽  
Buxus Sempervirens ◽  
Alkaloid Fraction

In the course of our studies on antiprotozoal natural products and following our recent discovery that certain aminosteroids and aminocycloartanoid compounds from Holarrhena africana A. DC. (Apocynaceae) and Buxus sempervirens L. (Buxaceae), respectively, are strong and selective antitrypanosomal agents, we have extended these studies to another plant, related to the latter—namely, Pachysandra terminalis Sieb. and Zucc. (Buxaceae). This species is known to contain aminosteroids similar to those of Holarrhena and structurally related to the aminocycloartanoids of Buxus. The dicholoromethane extract obtained from aerial parts of P. terminalis and, in particular, its alkaloid fraction obtained by acid–base partitioning showed prominent activity against Trypanosoma brucei rhodesiense (Tbr). Activity-guided fractionation along with extended UHPLC-(+)ESI QTOF MS analyses coupled with partial least squares (PLS) regression modelling relating the analytical profiles of various fractions with their bioactivity against Tbr highlighted eighteen constituents likely responsible for the antitrypanosomal activity. Detailed analysis of their (+)ESI mass spectral fragmentation allowed identification of four known constituents of P. terminalis as well as structural characterization of ten further amino-/amidosteroids not previously reported from this plant.

Alkaloids from Buxus sempervirens L. III. Mass spectral fragmentation

1965 ◽  
Vol 30 (8) ◽  
pp. 2869-2874 ◽  
Author(s):  
L. Dolejš ◽  
V. Hanuš ◽  
Z. Votický ◽  
J. Tomko
Keyword(s):  
Mass Spectral Fragmentation ◽  
Mass Spectral ◽  
Buxus Sempervirens

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.

Über die Darstellung von P-Chlor-substituierten Ν,N′-Dimethylharnstoff-verbrückten Diphosphorverbindungen, deren Enthalogenierung mit Oxalsäurebis(trimethylsilylester) und anschließende Oxidation mit Tetrachlororthobenzochinon / Preparation of P-Chloro-Substituted N′,N′-Dimethylurea-Bridged Diphosphorus Compounds, their Dehalogenation with Oxalic Acid Bis(trimethylsilyl) Ester and Subsequent Oxidation with Tetrachloroobenzoquinone

1989 ◽  
Vol 44 (6) ◽  
pp. 690-698 ◽  
Author(s):  
Roland Vogt ◽  
Reinhard Schmutzler
Keyword(s):  
Oxalic Acid ◽  
Nmr Spectra ◽  
Quantitative Yield ◽  
Fragmentation Pattern ◽  
Analogous Reaction ◽  
Trimethylsilyl Ester ◽  
Mass Spectral Fragmentation ◽  
Mass Spectral ◽  
Mass Spectral Fragmentation Pattern

Reaction of N,N′-dimethyl-N,N′-bis(trimethylsilyl)urea (1) with dichlorophosphines. RPCl2 (R = Et: 14; R = Pr: 15) has furnished the P-chloro-substituted acyclic diphosphorus compounds, 16 and 17. In the analogous reaction of 1 with Ph2PCl the corresponding bis(diphenylphosphino)-substituted derivative, 21 was formed. Dehalogenation of 11, 16 and 17 with oxalic acid bis(trimethylsilyl) ester, 22 has produced the mixed-valent cyclic λ3P,λ4P-diphosphorus compounds, 23-25 in almost quantitative yield. Oxidation of the λ3P atom in 23-25 with tetrachloroorthobenzoquinone, 26 has given rise to partial cleavage of the P-P bond, and only moderate yields of the products, 29, 31 and 32, have been obtained. The characterization of the various compounds obtained rests, especially, on their 1H and 31P NMR spectra, and on a study of their mass spectral fragmentation pattern

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.

Unambiguous structural and nuclear magnetic resonance spectral characterization of two triterpenoids of Maprouneaguianensis by two-dimensional nuclear magnetic resonance spectroscopy

1987 ◽  
Vol 65 (11) ◽  
pp. 2519-2525 ◽  
Author(s):  
Stewart McLean ◽  
Marion Perpick-Dumont ◽  
William F. Reynolds ◽  
Helen Jacobs ◽  
Sagar Singh Lachmansing
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Resonance Spectroscopy ◽  
Two Dimensional ◽  
Mass Spectral Fragmentation ◽  
Mass Spectral ◽  
Alternative Approaches ◽  
Fragmentation Patterns ◽  
Nuclear Magnetic

It is shown that 1H–13C shift-correlated two-dimensional spectra obtained for polarization transfer via two-bond and three-bond 13C–1H coupling can, in conjunction with related experiments, be used to assign unambiguously the molecular skeletons of two of the less common triterpenes, moretenone and 3-acetylaleuritolic acid. It is concluded that this is a technique of considerable generality for assigning structures of triterpenes and is more reliable than alternative approaches such as mass spectral fragmentation patterns. It has the additional benefit of simultaneously providing reliable 13C and 1H spectral assignments for these compounds.

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 Characterization of the genes specifying two metacyclic variable antigen types in Trypanosoma brucei rhodesiense.

1984 ◽  
Vol 81 (21) ◽  
pp. 6642-6646 ◽  
Author(s):  
M. J. Lenardo ◽  
A. C. Rice-Ficht ◽  
G. Kelly ◽  
K. M. Esser ◽  
J. E. Donelson
Keyword(s):  
Trypanosoma Brucei ◽  
Trypanosoma Brucei Rhodesiense ◽  
Variable Antigen
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