Identificación de la capsaicina y la deshidrocapsaicina en el extracto de oleorresina obtenido a partir del ají panca (Capsicum chinense)

Oleoresin is a liquid extract which is obtained from chili and peppers of genus Capsicum, to be used in the food industry very often. This paper describes the oleoresin extraction from aji panca chili pepper by the Soxhlet method. The yield of oleoresin was 22,77 % using ethanol as extraction solvent. The capsaicinoids ―capsaicin and dihydrocapsaicin― present in the oleoresin were identified in ethanol at a maximum 281 nm wavelength.La oleorresina es un extracto líquido que se obtiene a partir de ají y pimientos del género Capsicum, para ser usada  frecuentemente en la industria alimentaria. En este trabajo se ha descrito la extracción de la oleorresina a partir del ají panca, por el método Soxhlet. El rendimiento de la oleorresina fue de 22,77 %, con el empleo de etanol como solvente extractante. Los capsaicinoides capsaicina y deshidrocapsaicina, presentes en el extracto oleorresina, fueron identificados en etanol a una longitud de onda máxima de 281 nm

Novel Thiosemicarbazone Derivatives from Furan-2-Carbaldehyde: Synthesis, Characterization, Crystal Structures, and Antibacterial, Antifungal, Antioxidant, and Antitumor Activities

Ten new thiosemicarbazone derivatives, furan-2-carbaldehyde thiosemicarbazone (1), 3-methyl-furan-2-carbaldehyde thiosemicarbazone (2), 5-hydroxymethyl-furan-2-carbaldehyde thiosemicarbazone (3), 5-trifluoromethyl-furan-2-carbaldehyde thiosemicarbazone (4), 5-nitro-furan-2-carbaldehyde thiosemicarbazone (5), 5-phenyl-furan-2-carbaldehyde thiosemicarbazone (6), 5-(2-fluorophenyl)-furan-2-carbaldehyde thiosemicarbazone (7), 5-(4-methoxyphenyl)-furan-2-carbaldehyde thiosemicarbazone (8), 5-(1-naphthyl)-furan-2-carbaldehyde thiosemicarbazone (9), and 5-(1H-Pyrazol-5-yl)-furan-2-carbaldehyde thiosemicarbazone (10) were synthesized by condensing thiosemicarbazide with the respective furan-2-carbaldehyde in methanol. The prepared compounds were characterized by spectroscopic studies (FT-IR and NMR) and electrospray mass spectrometry. The molecular structures of 2, 6, 7, and 8 have also been determined by X-ray crystallography. Compounds 2, 6, and 7 crystallize in the E conformation about the N1-C6, N1-C11, and N1-C11 bonds, respectively, while 8 adopts the Z conformation about the N1-C12 bond with the presence of an intramolecular N2-H.O2 hydrogen bond. All prepared thiosemicarbazone derivatives were evaluated for their in vitro antibacterial, antifungal, and antitumor activities against Staphylococcus aureus strains, Candida albicans/Candida tropicalis fungi, and seven human tumor cell lines (HuTu80, H460, DU145, M-14, HT-29, MCF-7, and LNCaP), respectively. The antioxidant activity was also studied by the DPPH assay. Compound 5 exhibited significant antibacterial activity against Staphylococcus aureus ATCC700699 (MIC = 1 µg/mL) compared to the nitrofurantoin and gentamicin reference drugs (MIC = 1-25 and 10->100 µg/mL, respectively). Compound 4 was ten times less active than amphotericin B (MIC = 5 µg/mL) against Candida albicans (ATCC90028 and ATCC10231), while 1 exhibited a moderate effect of scavenging of DPPH radical (IC50 = 40.9 µg/mL) in comparison to ascorbic acid reference compound (IC50 = 22.0 µg/mL). Among all the studied thiosemicarbazones, 5 showed a higher cytotoxic activity (IC50 = 13.36-27.73 µ¿) in relation to the other tested compounds (IC50 = 34.84 - >372.34 µ¿) against all tested cell lines, except the LNCaP cell line, exhibiting its highest antiproliferative activity (IC50 = 13.36 µ¿) on the HuTu80 cell line. Besides, 8 and 9 exhibited high antitumor activity (IC50 = 13.31 and 7.69 µ¿, respectively) against the LNCaP cells.Revisión por pare

Synthesis, characterization, and in vitro cytotoxic activities of benzaldehyde thiosemicarbazone derivatives and their palladium(II) and platinum(II) complexes against various human tumor cell lines

The palladium (II) bis-chelate Pd (L 1 - 3) 2 and platinum (II) tetranuclear Pt 4 (L 4) 4 complexes of benzaldehyde thiosemicarbazone derivatives have been synthesized, and characterized by elemental analysis and IR, FAB (+) -mass and NMR (1 H, 13 C) spectroscopy. The complex Pd (L 2) 2 [H L 2 = m -CN-benzaldehyde thiosemicarbazone] shows a square-planar geometry with two deprotonated ligands (L) coordinated to Pd II through the nitrogen and sulphur atoms in a transarrangement, while the complex Pt 4 (L 4) 4 [H L 4 = 4 -phenyl-1-benzaldehyde thiosemicarbazone] has a tetranuclear geometry with four tridentate ligands coordinated to four Pt II ions through the carbon (aromatic ring), nitrogen, and sulphur atoms where the ligands are deprotonated at the NH group. The in vitro antitumor activity of the ligands and their complexes was determined against different human tumor cell lines, which revealed that the palladium (II) and platinum (II) complexes are more cytotoxic than their ligands with IC 50 values at the range of 0.07-3.67 µM. The tetranuclear complex Pt 4 (L 4) 4, with the phenyl group in the terminal amine of the ligand, showed higher antiproliferative activity (CI 50 = 0.07-0.12 µM) than the other tested palladium (II) complexes

Synthesis and Characterization of New Palladium(II) Complexes with Ligands Derived from Furan-2-carbaldehyde and Benzaldehyde Thiosemicarbazone and their in vitro Cytotoxic Activities against Various Human Tumor Cell Lines

With the ligands 4-phenyl-1-(furan-2-carbaldehyde)thiosemicarbazone, HTSC1, (1), 4-phenyl-1- (5 -phenyl-furan-2-carbaldehyde)thiosemicarbazone, HTSC2 (2), o-methoxy-benzaldehydethiosemicarbazone, HTSC3 (3), and o-cyano-benzaldehydethiosemicarbazone, HTSC4 (4), the corresponding palladium(II) complexes, Pd(TSC1)2 (5), Pd(TSC2)2 (6), Pd(TSC3)2 (7), and Pd(TSC4)2 (8) were synthesized and characterized by elemental analysis and spectroscopic techniques. The crystal structure of Pd(TSC3)2 (7) was determined by single-crystal X-ray diffraction. Complex 7 shows a squareplanar geometry, where two deprotonated ligands are coordinated to the PdII center through the nitrogen and sulfur atoms in a trans arrangement. In vitro antitumor studies against different human tumor cell lines have revealed that the palladium(II) complexes 5– 8 are more cytotoxic (IC50 values in the range of 0.21 – 3.79 µM) than their corresponding ligands (1 – 4) (> 60 µM). These results indicate that the antiproliferative activity is enhanced when thiosemicarbazone ligands are coordinated to the metal. Among the studied palladium(II) complexes, 8 exhibits high antitumor activity on K562 chronic myelogenous leukemia cells with a low value of the inhibitory concentration (IC50 = 0.21 µM)

Synthesis, Spectroscopic Characterization, Structural Studies, and in Vitro Antitumor Activities of Pyridine-3-carbaldehyde Thiosemicarbazone Derivatives

Eight new thiosemicarbazone derivatives, 6-(1-trifluoroethoxy)pyridine-3-carbaldehyde thiosemicarbazone (1), 6-(4'-fluorophenyl)pyridine-3-carbaldehyde thiosemicarbazone (2), 5-chloro-pyridine-3-carbaldehyde thiosemicarbazone (3), 2-chloro-5-bromo-pyridine-3-carbaldehyde thiosemicarbazone (4), 6-(3',4'-dimethoxyphenyl)pyridine-3-carbaldehyde thiosemicarbazone (5), 2-chloro-5-fluor-pyridine-3-carbaldehyde thiosemicarbazone, (6), 5-iodo-pyridine-3-carbaldehyde thiosemicarbazone (7), and 6-(3',5'-dichlorophenyl)pyridine-3-carbaldehyde thiosemicarbazone (8) were synthesized, from the reaction of the corresponding pyridine-3-carbaldehyde with thiosemicarbazide. The synthesized compounds were characterized by ESI-Mass, UV-Vis, IR, and NMR (1H, 13C, 19F) spectroscopic techniques. Molar mass values and spectroscopic data are consistent with the proposed structural formulas. The molecular structure of 7 has been also confirmed by single crystal X-ray diffraction. In the solid state 7 exists in the E conformation about the N2-N3 bond; 7 also presents the E conformation in solution, as evidenced by 1H NMR spectroscopy. The in vitro antitumor activity of the synthesized compounds was studied on six human tumor cell lines: H460 (lung large cell carcinoma), HuTu80 (duodenum adenocarcinoma), DU145 (prostate carcinoma), MCF-7 (breast adenocarcinoma), M-14 (amelanotic melanoma), and HT-29 (colon adenocarcinoma). Furthermore, toxicity studies in 3T3 normal cells were carried out for the prepared compounds. The results were expressed as IC50 and the selectivity index (SI) was calculated. Biological studies revealed that 1 (IC50 = 3.36 to 21.35 µM) displayed the highest antiproliferative activity, as compared to the other tested thiosemicarbazones (IC50 = 40.00 to >582.26 µM) against different types of human tumor cell lines. 1 was found to be about twice as cytotoxic (SI = 1.82) than 5-fluorouracile (5-FU) against the M14 cell line, indicating its efficiency in inhibiting the cell growth even at low concentrations. A slightly less efficient activity was shown by 1 towards the HuTu80 and MCF7 tumor cell lines, as compared to that of 5-FU. Therefore, 1 can be considered as a promising candidate to be used as a pharmacological agent, since it presents significant activity and was found to be more innocuous than the 5-FU anticancer drug against the 3T3 mouse embryo fibroblast cells

Synthesis and Characterization of New Palladium(II) Thiosemicarbazone Complexes and Their Cytotoxic Activity against Various Human Tumor Cell Lines

The palladium(II) bis-chelate complexes of the type [Pd(TSC1-5)2] (6–10), with their corresponding ligands 4-phenyl-1-(acetone)-thiosemicarbazone, HTSC1 (1), 4-phenyl-1-(2'-chloro-benzaldehyde)-thiosemicarbazone, HTSC2 (2), 4-phenyl-1-(3'-hydroxy-benzaldehyde)-thiosemicarbazone, HTSC3 (3), 4-phenyl-1-(2'-naphthaldehyde)-thiosemicarbazone, HTSC4 (4), and 4-phenyl-1-(1'-nitro-2'-naphthaldehyde)-thiosemicarbazone, HTSC5 (5), were synthesized and characterized by elemental analysis and spectroscopic techniques (IR and 1H- and 13C-NMR). The molecular structure of HTSC3, HTSC4, and [Pd(TSC1)2] (6) have been determined by single crystal X-ray crystallography. Complex 6 shows a square planar geometry with two deprotonated ligands coordinated to through the azomethine nitrogen and thione sulfur atoms in a cis arrangement. The in vitro cytotoxic activity measurements indicate that the palladium(II) complexes (–9.87¿M) exhibited higher antiproliferative activity than their free ligands (–70.86 and >250¿M) against different types of human tumor cell lines. Among all the studied palladium(II) complexes, the [Pd(TSC3)2] (8) complex exhibited high antitumor activity on the DU145 prostate carcinoma and K562 chronic myelogenous leukemia cells, with low values of the inhibitory concentration (0.01 and 0.02¿M, resp.)

Nuevos materiales bioorgánicos de actividad antitumoral

El presente trabajo describe la síntesis, caracterización y evaluación de la actividad antitumoral in vitro de nuevos compuestos orgánicos derivados del 4-R-fenil-1-(X-tiazol-2/5-carbaldehído) tiosemicarbazona (R=H, fenilo; X=fenilo, o-/m-/p-OCH3-fenilo, p-Cl/F-fenilo, morfolinilo, Cl, N(CH3)2, metilo) y Xtriazol- 5-carbaldehído tiosemicarbazona (X=H, fenilo, p-Cl-fenilo). La preparación de estos compuestos se realizó mediante la reacción de condensación entre la tiosemicarbazida o 4-feniltiosemicarbazida y los derivados tiazol-2/5-carbaldehído o triazol-5-carbaldehído, para lo cual se empleó como solvente el metanol. La caracterización química se realizó mediante análisis elemental, espectrometría de masas, técnicas espectroscópicas de infrarrojo (FT-IR) y resonancia magnética nuclear (1H, 13C), y difracción de rayos X.El presente trabajo describe la síntesis, caracterización y evaluación de la actividad antitumoral in vitro de nuevos compuestos orgánicos derivados del 4-R-fenil-1-(X-tiazol-2/5-carbaldehído) tiosemicarbazona (R=H, fenilo; X=fenilo, o-/m-/p-OCH3-fenilo, p-Cl/F-fenilo, morfolinilo, Cl, N(CH3)2, metilo) y Xtriazol- 5-carbaldehído tiosemicarbazona (X=H, fenilo, p-Cl-fenilo). La preparación de estos compuestos se realizó mediante la reacción de condensación entre la tiosemicarbazida o 4-feniltiosemicarbazida y los derivados tiazol-2/5-carbaldehído o triazol-5-carbaldehído, para lo cual se empleó como solvente el metanol. La caracterización química se realizó mediante análisis elemental, espectrometría de masas, técnicas espectroscópicas de infrarrojo (FT-IR) y resonancia magnética nuclear (1H, 13C), y difracción de rayos X

Nuevos complejos de platino (II) con ligandos derivados del benzofurano carbaldehído/ acetil tiosemicarbazona de actividad antitumoral

Los cánceres de estómago, de mama y de pulmón son los de mayor incidencia en el Perú; se les considera un problema de salud pública. El presente trabajo tiene como objetivo sintetizar, caracterizar y evaluar la actividad antitumoral de nuevos complejos de platino (II) con ligandos derivados del benzofurano 2-/3-/5-carbaldehído tiosemicarbazona.Los cánceres de estómago, de mama y de pulmón son los de mayor incidencia en el Perú; se les considera un problema de salud pública. El presente trabajo tiene como objetivo sintetizar, caracterizar y evaluar la actividad antitumoral de nuevos complejos de platino (II) con ligandos derivados del benzofurano 2-/3-/5-carbaldehído tiosemicarbazona

Identificación de la capsaicina y la deshidrocapsaicina en el extracto de oleorresina obtenido a partir del ají panca (Capsicum chinense)

La oleorresina es un extracto líquido que se obtiene a partir de ají y pimientos del género Capsicum, para ser usada frecuentemente en la industria alimentaria. En este trabajo se ha descrito la extracción de la oleorresina a partir del ají panca, por el método Soxhlet. El rendimiento de la oleorresina fue de 22,77 %, con el empleo de etanol como solvente extractante. Los capsaicinoides capsaicina y deshidrocapsaicina, presentes en el extracto oleorresina, fueron identificados en etanol a una longitud de onda máxima de 281 nm.Oleoresin is a liquid extract which is obtained from chili and peppers of genus Capsicum, to be used in the food industry very often. This paper describes the oleoresin extraction from aji panca chili pepper by the Soxhlet method. The yield of oleoresin was 22,77 % using ethanol as extraction solvent. The capsaicinoids ¿capsaicin and dihydrocapsaicin¿ present in the oleoresin were identified in ethanol at a maximum 281 nm wavelength

Complejos de cobre(II) y cobalto (II) con derivados de la piridina2/3-carbaldehído tiosemicarbazona como agentes antitumorales

Con la finalidad de usar menores concentraciones de fármacos en el rango micromolar y de disminuir los efectos secundarios en tratamientos anticancerígenos, este estudio describirá la preparación y evaluará la actividad antitumoral in vitro de los complejos de cobre(II) y cobalto(II) con ligandos derivados de la piridina-2/3-carbaldehído tiosemicarbazona. El efecto antiproliferante que se espera alcanzar de los compuestos se evidenciará por los bajos valores CI50 (concentración micromolar requerida para inhibir el 50 % de crecimiento celular) frente a las diferentes líneas de células tumorales de humano y los elevados valores CI50 ante una línea de células normales.Con la finalidad de usar menores concentraciones de fármacos en el rango micromolar y de disminuir los efectos secundarios en tratamientos anticancerígenos, este estudio describirá la preparación y evaluará la actividad antitumoral in vitro de los complejos de cobre(II) y cobalto(II) con ligandos derivados de la piridina-2/3-carbaldehído tiosemicarbazona. El efecto antiproliferante que se espera alcanzar de los compuestos se evidenciará por los bajos valores CI50 (concentración micromolar requerida para inhibir el 50 % de crecimiento celular) frente a las diferentes líneas de células tumorales de humano y los elevados valores CI50 ante una línea de células normales