scholarly journals Synthesis, NMR Characterization, and Antileukemic Activity of N-Nonanoylpiperazinyl-5α-Androstane-3α,17β-Diol A-Ring Derivatives

2020 ◽  
Vol 7 (1) ◽  
pp. 3
Author(s):  
Donald Poirier ◽  
Imad Raad ◽  
Jenny Roy ◽  
René Maltais
Keyword(s):  
Multiple Bond ◽  
Correlation Spectroscopy ◽  
Heteronuclear Multiple Bond Correlation ◽  
Steroid Nucleus ◽  
New Family ◽  
Overhauser Effect ◽  
Nmr Characterization ◽  
Crucial Information ◽  
Heteronuclear Single Quantum Correlation ◽  
The Impact

The combination of an androstane-3,17-diol nucleus and a 2β-N-alkylamidopiperazino sidechain is important for the anticancer activity of a new family of steroid derivatives. As the structure-activity relationship studies have so far been limited to the beta orientation of the substituent at position 2 of the steroid nucleus, a series of analogs (compounds 1–4) were synthesized to investigate the impact on biological activity of A-ring substitution. Nuclear magnetic resonance (NMR) analysis, especially using a series of 2D experiments, such as correlation spectroscopy (COSY), homonuclear Overhauser effect spectroscopy (NOESY), heteronuclear single-quantum correlation (HSQC), and heteronuclear multiple-bond correlation (HMBC) provided crucial information that was found essential in confirming the sidechain position and orientation of compounds 1–4. Assessment of their antiproliferative activity on leukemia HL-60 cells confirmed the best efficiency of the 2β-sidechain/3α-OH orientation (compound 1) compared to the other configurations tested (compounds 2–4).

scholarly journals CARACTERIZACIÓN DE UNA ESPIROLACTONA SESQUITERPÉNICA á-METILÉNICA OBTENIDA DE Ambrosia arborescens Miller Y EVALUACIÓN DE SU ACTIVIDAD BIOLÓGICA EN Tripanosoma cruzi

2014 ◽  
Vol 80 (2) ◽  
pp. 124-135
Author(s):  
Teresa Cano de Terrones
Keyword(s):  
Quantum Correlation ◽  
Multiple Bond ◽  
Correlation Spectroscopy ◽  
Single Quantum ◽  
Heteronuclear Multiple Bond Correlation ◽  
Heteronuclear Single Quantum Correlation ◽  
América Del Sur

Ambrosia arborescens Miller, denominada comúnmente "marco"; es una planta aromática, medicinal que se encuentra en América del Sur, mayormente en los Andes del Perú, en el Departamento de Arequipa. El estudio de los constituyentes químicos de la parte aérea de Ambrosia arborescens permitió obtener una espirolactona sesquiterpénica. Para su separación y aislamiento se utilizó métodos cromatográficos de columna, capa fina y cromatografía líquida de alta eficacia. La elucidación estructural se realizó a través de métodos espectroscópicos: resonancia magnética nuclear protónica (RMN-1H), del carbono-13 (RMN-13C), espectroscopía infrarroja (IR) y espectrometría de masas (EM). En la determinación de la estereoquímica y las conformaciones se empleó experimentos bidimensionales de espectroscopía: COSY (Correlation Spectroscopy), HSQC (Heteronuclear Single Quantum Correlation), HMBC (Heteronuclear Multiple Bond Correlation) y ROESY(Rotational nuclear Overhouser Effect Spectroscopy). Desde un punto de vista teórico, el análisis conformacional fue realizado a través de Mecánica Molecular empleando el programa MM2 de Hyperchem. La evaluación de la actividad antiparasitaria, in vitro, sobre Tripanosoma cruzi, mostró que a muy bajas concentraciones, el producto obtenido presenta actividad tripanocida.

scholarly journals Chemical Constituents of Tagetes patula and Their Neuroprotecting Action

2020 ◽  
Vol 15 (11) ◽  
pp. 1934578X2097450
Author(s):  
Linlin Liu ◽  
Simin Luo ◽  
Miao Yu ◽  
Ahmed M. Metwaly ◽  
Xiaoku Ran ◽  
...  
Keyword(s):  
High Performance ◽  
Chemical Constituents ◽  
Multiple Bond ◽  
Tagetes Patula ◽  
Chemical Methods ◽  
Heteronuclear Multiple Bond Correlation ◽  
Flight Mass Spectrometry ◽  
Whole Plant ◽  
Heteronuclear Single Quantum Correlation ◽  
Neuroprotective Action

Two novel flavonoids (1, 2) and 3 known compounds (3-5) were isolated from the flowers and whole plant of Tagetes patula L., and their structures were elucidated by means of ultra-high performance liquid chromatography with electrospray ionization, coupled to quadrupole-time-of-flight/mass spectrometry, 1H and 13C-nuclear magnetic resonance (NMR), as well as 2-dimensional-NMR (heteronuclear single quantum correlation and heteronuclear multiple bond correlation) and chemical methods. In addition, all the compounds were examined for their neuroprotective action on the injury of SH-SY5Y cells induced by glutamate, indicating that the protective effect of these compounds on glutamate-induced SH-SY5Y cell was marigold biflavone > patuletin > quercetin > kaempferol-3- O-β-d-glucoside > patuletin-3- O-α-l-arabinopyranoside. Thus, it could be concluded that flavonoids played a key role in the neuroprotective action of T. patula.

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