Synthesis, Photophysical Properties, Theoretical Studies, and Living Cancer Cell Imaging Applications of New 7-(Diethylamino)quinolone Chalcones.

In this article, three unsymmetrical 7-(diethylamino)quinolone chalcones with D-π-A-D and D-π-A-π-D type push-pull molecular arrangements were synthesized via a Claisen-Schmidt reaction. Using 7-(diethylamino)quinolone and vanillin as electron donor (D) moieties, these were linked together through the α,ß-unsaturated carbonyl system acting as a linker and an electron acceptor (A). The photophysical properties were studied, revealing significant Stokes shifts and strong solvatofluorochromism caused by the ICT and TICT behavior produced by the push-pull effect. Moreover, quenching caused by the population of the TICT state in THF-H2O mixtures was observed, and the emission in the solid state evidenced a red shift compared to the emission in solution. These findings were corroborated by density functional theory (DFT) calculations employing the wb97xd/6-311G(d,p) method. The cytotoxic activity of the synthesized compounds was assessed on BHK-21, PC3, and LNCaP cell lines, revealing moderate activity across all compounds. Notably, compound 5b exhibited the highest activity against LNCaP cells, with an LC50 value of 10.89 µM. Furthermore, the compounds were evaluated for their potential as imaging agents in living prostate cells. The results demonstrated their favorable cell permeability and strong emission at 488 nm, positioning them as promising candidates for cancer cell imaging applications.

Volatile Metabolites of Piper eriopodon (Miq.) C.DC. from Northern Region of Colombia and Assessment of In Vitro Bioactivities of the Leaf Essential Oil.

Piper eriopodon is one of the Piper species found in the Sierra Nevada de Santa Marta, and the species has been reported with different compositions of their essential oils (EO). In this study, the volatile fractions/essential oil (by HS-SPME/SDE/MWHD-GC-MS/1H-NMR) of different parts from the plant were characterized, and assessments of the in vitro bio-properties of the leaf EO were conducted. The results indicated the following: (i) in the volatile fractions were ß-caryophyllene (~23%)/myrcene (~20%) (inflorescences) and ß-caryophyllene (~43%)/ß-selinene (~20%) (leaves) using HS-SPME; myrcene (~31%)/ß-pinene (~23%) (inflorescences), gibbilimbol B (~60%) (fruits) and gibbilimbol B (~46%)/ß-caryophyllene (~11%) (leaves) through SDE; (ii) leaf EO contained gibbilimbol B (~72%), confirmed with 1H-NMR; (iii) the cytotoxic values (µg/mL) in erythrocytes/lymphocytes/Hep-2 were HC50: 115 ± 3 (eryth.), LC50: 71 ± 4 (lymph.) and LC50: 33 ± 2 (cell-line); (iv) the antibacterial susceptibilities (ϕ inh. zone, mm; 4-16 µg EO) were 22.5 ± 0.4-97 ± 4 (Staphylococcus aureus), 23 ± 2-77 ± 4 (Escherichia coli) and 17 ± 1-48 ± 3 (Listeria monocytogenes); (v) the TAA value was 2249 ± 130 mmol Trolox®/kg; (vi) the IC50 value was 13±1 µg/mL (AChE) with 20 ± 0-37 ± 6% repellency (2-4 h, Sitophilus zeamais). Thus, the EO of P. eriopodon leaves from northern Colombia could be a promising species for sustainable exploitation in the future due to its outstanding bioactivities.

Soybean meal substitution by dehulled lupine (Lupinus angustifolius) with enzymes in broiler diets.

OBJECTIVE: Evaluate the effects of i) dehulling of lupine seed on chemical composition and apparent metabolizable energy (AME) and ii) soybean meal substitution by dehulled lupine seed in broiler diets with enzymes on productive performance, size of digestive organs and welfare-related variables. METHODS: Experiment 1, chemical composition and AME were determined in whole and dehulled lupine seed. Experiment 2, two hundred eighty-eight one-day-old male Ross 308 broilers were used. The experimental diets were maize-soybean meal (MS), MS with enzymes (MSE) and maize-dehulled lupine seed with enzymes (MLE). Diets were assigned to the experimental units under a completely randomized design (eight replicates per diet). The body weight (BW) gain, feed intake, feed conversion, digestive organ weights, gait score, latency to lie down and valgus/varus angulation were evaluated. RESULTS: The dehulling process increased protein (25.0% to 31.1%), AME (5.9 to 8.8 MJ/kg) and amino acid contents. The BW gain of broilers fed the MLE diet was similar (p>0.05) to that of those fed the MS diet, but lower than that of those fed the MSE diet. Feed intake of broilers fed the MLE diet was higher (p<0.05) than that of those fed the MS diet and similar (p>0.05) to those fed the MSE diet. Feed conversion of broilers fed the MLE diet was 8.0% and 8.7% higher (p<0.05) than that of those fed the MS and MSE diets, respectively. Broilers fed the MLE diet had the highest (p<0.05) relative proventriculus and gizzard weights, but had poor welfare-related variables. CONCLUSION: It is possible to substitute soybean meal by dehulled lupine seed with enzymes in broiler diets, obtaining similar BW gains in broilers fed the MLE and MS diets; however, a higher feed intake is required. Additionally, the MLE diet reduced welfare-related variables.

Citotoxicidad/capacidad antiradicalaria in-vitro y caracterización estructural por GC-MS/1H-13C-RMN de los aceites esenciales de hojas de árboles joven/adulto de annona purpurea Moc. & Sessé ex Dunal de Repelón (Atlántico, Colombia) / [in-vitro Cytotoxicity/Anti-Radical Capability and structural characterization by GC-MS/1H13C-NMR of theleaves essential oils of young/old trees of Annona purpurea Moc. & Sessé ex Dunal from Repelón (Atlántico,Colombia]

Annona purpurea es una planta empleada en etnomedicina, en la región norte de Colombia, que no tiene reportes científicos relacionados con la composición de su AE y sus actividades biológicas. En este trabajo, los AE de hojas de árboles joven/adulto se caracterizaron por GC-MS y RMN y se evaluaron sus propiedades antiradicalarias/citotóxicas. Los AE de hojas de árboles joven/adulto estuvieron representados por beta-eudesmol (68.9 por ciento) y alfa-eudesmol (16.8 por ciento), y germacreno D (55.6 por ciento) y biciclogermacreno (20.3 por ciento), respectivamente. El análisis por RMN mostró las señales distintivas de los constituyentes mayoritarios identificados. Los valores de TAA (mmol Trolox®/kg SE) obtenidos por los AE de árboles joven/adulto fueron 165 +/- 8 y 602 +/- 38. Los AE de árboles joven/adulto evaluados sobre linfocitos humanos fueron “moderadamente tóxicos” con valores de CL50 (ug/mL) de 145.5 +/- 0.7 y 346 +/- 8. Finalmente, la citotoxicidad en eritrocitos humanos reveló que el AE de árbol adulto no fue hemolítico (CL50 > 1000 μg/mL, 4.3 +/- 0.6 por ciento); mientras que, el AE de árbol joven fue hemolítico (CL50 490 +/- 48 ug/mL).

Annona purpurea is a plant used in ethnomedicine in the northern region of Colombia, which has no scientific reports on the composition of their essential oil (EO) and biological activities. In this work, the leaves EO of young/old trees were characterized by GC- MS and NMR, and their antiradical/cytotoxic properties were evaluated. beta-Eudesmol (68.9 percent) and alpha-eudesmol (16.8 percent), and germacrene D (55.6 percent) and bicyclogermacrene (20.3 percent), were the representative compounds of the leaves EO of young/old trees, respectively. The NMR analysis showed the distinctive signals of the main constituents identified. The TAA values (mmol Trolox®/kg ES) obtained from the EO of young/old trees were 165 +/- 8 and 602 +/- 38. The EO of young/old trees evaluated on human lymphocytes were “moderately toxic” with LC50 (μg/mL) of 145.5 +/- 0.7 and 346 +/- 8. Finally, the cytotoxicity in human erythrocytes revealed that the old tree EO was not haemolytic (LC50 > 1000 ug/mL, 4.3 +/- 0.6 percent); while the young tree EO was hemolytic (LC50 490 +/- 48 ug/mL).

Estudio químico-biológico de los aceites esenciales de Croton malambo H. Karst y su componente mayoritario, metileugenol / Chemical-biological study of the essential oils from Croton malambo H. Karst.and their major component, methyleugenol

Croton malambo is a plant used in traditional medicine, in Colombia. The aim of this research was to characterize the essential oils (EO) from leaves and branches by GC-MS, NMR and determine the antiradical capacities and the in vitro and in vivo cytotoxic properties of the EO, methyleugenol (ME) and eugenol (EU). The EO of leaves and branches of C. malambo presented to ME as the main constituent (68.5 percent and 85.1 percent, respectively) and their structure was confirmed by NMR. On the other hands, the antiradical capacities (ABTS+. method) of the EO and ME were very low, obtaining only inhibition values at a fixed concentration: to 2045 ug/mL – 50 +/- 2 percent (leaves EO) and 28 +/- 1 percent (branches EO); and, 2218 ug/mL - 2.0 +/- 0.2 percent (ME). While EU had the highest value of TAA (14003 +/- 719 mmol Trolox®/kg SE). According to lymphocytes citotoxicity test, all tested substances were classified as “moderately toxic”, with values of LC50 between 310 +/- 17 – 897 +/- 11 ug/mL, being the EO the most toxic. The assessment of the toxicity in Zebra fish embryos indicated that LC50 of the branches EO, ME and EU were between 16 +/- 9 – 43 +/- 9 ug/mL, being the EU the most toxic.

Croton malambo es una planta empleada en medicina tradicional, en Colombia. El objetivo de esta investigación fue caracterizar los aceites esenciales (AE) de hojas y ramas por GC-MS, RMN y determinar las capacidades antiradicalarias y las propiedades citotóxicas in vitro e in vivo de los AE, metileugenol (ME) y eugenol (EU). Los AE de hojas y ramas de Croton malambo presentaron a ME como el constituyente principal (68.5 por ciento y 85.1 por ciento, respectivamente) y su estructura fue confirmada por RMN. Por otro lado, las capacidades antiradicalarias (método ABTS+.) de los AE y ME fueron muy bajas, obteniéndose sólo valores de inhibición a una concentración fija: a 2045 ug/mL – 50 +/- 2 por ciento (AE de hojas) y 28 +/- 1 por ciento (AE de ramas); y, 2218 ug/mL - 2.0 +/- 0.2 por ciento (ME). Mientras que, EU tuvo el mayor valor de TAA (14003 +/- 719 mmol Trolox®/kg SE). Según el ensayo de citotoxicidad en linfocitos, todas las sustancias evaluadas se catalogaron como “moderadamente tóxicas”, con valores de CL50 entre 310 +/- 17 – 897 +/- 11 ug/mL, siendo los AE los más tóxicos. La estimación de la toxicidad en embriones del pez Cebra indicó que las CL50 del AE ramas, ME y EU estuvieron entre 16 +/- 9 – 43 +/- 9 ug/mL, siendo el EU el más tóxico.