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1. Formulation and optimization of polymeric nanoparticles loaded with riolozatrione: a promising nanoformulation with potential antiherpetic activity

Author

Solís-Cruz Guadalupe Y., Alvarez-Roman Rocío, Rivas-Galindo Verónica M., Galindo-Rodríguez Sergio Arturo, Silva-Mares David A., Marino-Martínez Iván A., Escobar-Saucedo Magdalena, and Pérez-López Luis A.

Subjects
riolozatrione, polymeric nanoparticles, herpes simplex virus, antiviral, Pharmaceutical industry, HD9665-9675
Abstract

Riolozatrione (RZ) is a diterpenoid compound isolated from a dichloromethane extract of the Jatropha dioica root. This compound has been shown to possess moderate antiherpetic activity in vitro. However, because of the poor solubility of this compound in aqueous vehicles, generating a stable formulation for potential use in the treatment of infection is challenging. The aim of this work was to optimize and physio-chemically characterize Eudragit® L100-55-based polymeric nanoparticles (NPs) loaded with RZ (NPR) for in vitro antiherpetic application. The NPs formulation was initially optimized using the dichloromethane extract of J. dioica, the major component of which was RZ. The optimized NPR formulation was stable, with a size of 263 nm, polydispersity index < 0.2, the zeta potential of –37 mV, and RZ encapsulation efficiency of 89 %. The NPR showed sustained release of RZ for 48 h with release percentages of 95 and 97 % at neutral and slightly acidic pH, respectively. Regarding in vitro antiherpetic activity, the optimized NPR showed a selectivity index for HSV-1 of ≈16 and for HSV-2 of 13.

Published
2023
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11. Formulation and optimization of polymeric nanoparticles loaded with riolozatrione: a promising nanoformulation with potential anti-herpetic activity

Author

SOLÍS-CRUZ, GUADALUPE Y., ALVAREZ-ROMAN, ROCÍO, RIVAS-GALINDO, VERÓNICA M., GALINDO-RODRÍGUEZ, SERGIO ARTURO, SILVA-MARES, DAVID A., MARINO-MARTÍNEZ, IVÁN A., ESCOBAR-SAUCEDO, MAGDALENA, PÉREZ-LÓPEZ, LUIS A., SOLÍS-CRUZ, GUADALUPE Y., ALVAREZ-ROMAN, ROCÍO, RIVAS-GALINDO, VERÓNICA M., GALINDO-RODRÍGUEZ, SERGIO ARTURO, SILVA-MARES, DAVID A., MARINO-MARTÍNEZ, IVÁN A., ESCOBAR-SAUCEDO, MAGDALENA, and PÉREZ-LÓPEZ, LUIS A.

Abstract

Riolozatrione (RZ) is a diterpenoid compound isolated from a dichloromethane extract of the Jatropha dioica root. This compound has been shown to possess moderate anti-herpetic activity in vitro. However, because of the poor solubility of this compound in aqueous vehicles, generating a stable formulation for potential use in the treatment of infection is challenging. The aim of this work was to optimize and physiochemically characterize Eudragit® L100-55-based polymeric nanoparticles (NPs) loaded with RZ (NPR) for in vitro anti-herpetic application. The NPs formulation was initially optimized using the dichloromethane extract of J. dioica, the major component of which was RZ. The optimized NPR formulation was stable, with a size of 263 nm, polydispersity index < 0.2, the zeta potential of –37 mV, and RZ encapsulation efficiency of 89 %. The NPR showed sustained release of RZ for 48 h with release percentages of 95 and 97 % at neutral and slightly acidic pH, respectively. Regarding in vitro anti-herpetic activity, the optimized NPR showed a selectivity index for HSV-1 of ≈16 and for HSV-2 of 13.

Published
2023

12. Towards an Eco-Friendly Coffee Rust Control: Compilation of Natural Alternatives from a Nutritional and Antifungal Perspective

Author

Castillo, Nora E. Torres, primary, Acosta, Yovanina Aguilera, additional, Parra-Arroyo, Lizeth, additional, Martínez-Prado, María Adriana, additional, Rivas-Galindo, Verónica M., additional, Iqbal, Hafiz M. N., additional, Bonaccorso, A. Damiano, additional, Melchor-Martínez, Elda M., additional, and Parra-Saldívar, Roberto, additional

Published
2022
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13. Amino ether analogues of 4,4′-dihydroxy-3-methoxy-6,7′-cyclolignan and their activity against drug-resistant bacteria

Author

Núñez-Mojica, Guillermo, primary, Hernández-Carrillo, Martha L., additional, Avalos-Alanís, Francisco G., additional, Garza-González, Elvira, additional, Rivas-Galindo, Verónica M., additional, Silva-Mares, David A., additional, Bazin, Marc-Antoine, additional, Marchand, Pascal, additional, and Camacho-Corona, María del Rayo, additional

Published
2022
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17. Effect of the nO → π*C═O Interaction on the Conformational Preference of 1,3-Diketones: A Case Study of Riolozatrione Derivatives

Author

Tamez-Fernández, Juan F., primary, Soto-Suárez, Fátima M., additional, Estrada-Chavarría, Yolanda D., additional, Quijano-Quiñones, Ramiro F., additional, Toscano, Rubén A., additional, Cuétara-Guadarrama, Fabián, additional, Duarte-Alaniz, Víctor, additional, Ibarra-Rivera, Tannya R., additional, Quiroz-García, Beatriz, additional, Martínez-Otero, Diego, additional, Ramírez-Gualito, Karla, additional, Barquera-Lozada, José Enrique, additional, Rivas-Galindo, Verónica M., additional, and Cuevas, Gabriel, additional

Published
2021
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19. Antibacterial and cytotoxic activities of new sphingolipids and other constituents isolated from Cissus incisa leaves

Author

Química orgánica II, Kimika organikoa II, Nocedo Mena, Deyani, Rivas Galindo, Verónica M., Navarro Villaverde, Patricia, Garza González, Elvira, González Maya, Leticia, Ríos, María Yolanda, García, Abraham, Ávalos Alanís, Francisco G., Rodríguez Rodríguez, José, Camacho Corona, María del Rayo, Química orgánica II, Kimika organikoa II, Nocedo Mena, Deyani, Rivas Galindo, Verónica M., Navarro Villaverde, Patricia, Garza González, Elvira, González Maya, Leticia, Ríos, María Yolanda, García, Abraham, Ávalos Alanís, Francisco G., Rodríguez Rodríguez, José, and Camacho Corona, María del Rayo

Abstract

Cissus incisa is used in traditional Mexican medicine to treat certain ailments, infectious or cancerous diseases. Excepting for our previous research, this species had no scientific reports validating its traditional use. In this study, we evaluated the antibacterial and cytotoxic properties of the sphingolipids and others phytocompounds isolated from C. incisa leaves to increase the scientific knowledge of the Mexican flora. The antibacterial activity was evaluated against Gram-positive and Gram-negative bacteria by the Microdilution method. Meanwhile, the cytotoxic potential was determined on six human cancer cells: PC3, Hep3B, HepG2, MCF7, A549, and HeLa; using an aqueous solution cell proliferation assay kit. A cell line of immortalized human hepatocytes (IHH) was included as a control of non-cancerous cells. Selectivity index (SI) was determined only against the hepatocellular carcinoma cell lines. The phytochemical investigation of C. incisa leaves resulted in the isolation and characterization of five compounds: 2-(2'-hydroxydecanoyl amino)-1,3,4- hexadecanotriol-8-ene (1), 2,3-dihydroxypropyl tetracosanoate (2), beta-sitosterol-D-glucopyranoside (3), alpha-amyrin-3-O-beta-D-glucopyranoside (4), and a mixture of cerebrosides (5). Until now, this is the first report of the sphingolipids (1), (5-IV) and (5-V). Only the compound (4) and cerebrosides (5) exhibited antibacterial activity reaching a MIC value of 100 mu g/mL against Pseudomonas aeruginosa resistant to carbapenems. While, the acetylated derivate of (3), compound (3Ac) showed the best cytotoxic result against PC3 (IC50 = 43 +/- 4 mu g/mL) and Hep3B (IC50 = 49.0 +/- 4 mu g/mL) cancer cell lines. Likewise, (3Ac) achieved better SI values on HepG2 and Hep3B cell lines. This research reveals the importance of study medicinal plants, to identify bioactive molecules as sources of potential drugs. The presence of these compounds allows us to justify the use of this plant in traditional Mexican medicine.

Published
2020

20. Antimicrobial and antileishmanial activities of extracts and some constituents from the leaves of Solanum chrysotrichum Schldl

Author

Núñez-Mojica, Guillermo, primary, Rivas-Galindo, Verónica M., additional, Garza-González, Elvira, additional, Miranda, Luis D., additional, Romo-Pérez, Adriana, additional, Pagniez, Fabrice, additional, Picot, Carine, additional, Le Pape, Patrice, additional, Bazin, Marc-Antoine, additional, Marchand, Pascal, additional, and Camacho-Corona, María del Rayo, additional

Published
2020
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21. Synthesis and in vitro evaluation of antimycobacterial and cytotoxic activity of new α,β-unsaturated amide, oxazoline and oxazole derivatives from -serine

Author

Aguirre-Rentería, Saúl A., primary, Carrizales-Castillo, Juan J.J., additional, del Rayo Camacho Corona, María, additional, Hernández-Fernández, Eugenio, additional, Garza-González, Elvira, additional, Rivas-Galindo, Verónica M., additional, Arredondo-Espinoza, Eder, additional, and Avalos-Alanís, Francisco G., additional

Published
2020
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24. Chemical composition of Acacia farnesiana (L) wild fruits and its activity against Mycobacterium tuberculosis and dysentery bacteria

Author

Hernández-García, Erika, primary, García, Abraham, additional, Garza-González, Elvira, additional, Avalos-Alanís, Francisco G., additional, Rivas-Galindo, Verónica M., additional, Rodríguez-Rodríguez, José, additional, Alcantar-Rosales, Victor M., additional, Delgadillo-Puga, Claudia, additional, and del Rayo Camacho-Corona, María, additional

Published
2019
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26. Effect of the nO→ π*C═OInteraction on the Conformational Preference of 1,3-Diketones: A Case Study of Riolozatrione Derivatives

Author

Tamez-Fernández, Juan F., Soto-Suárez, Fátima M., Estrada-Chavarría, Yolanda D., Quijano-Quiñones, Ramiro F., Toscano, Rubén A., Cuétara-Guadarrama, Fabián, Duarte-Alaniz, Víctor, Ibarra-Rivera, Tannya R., Quiroz-García, Beatriz, Martínez-Otero, Diego, Ramírez-Gualito, Karla, Barquera-Lozada, José Enrique, Rivas-Galindo, Verónica M., and Cuevas, Gabriel

Abstract

The cyclopropane ring-opening reaction of riolozatrione, a natural product obtained from Jatropha dioica, afforded a 2,2-disubstituted 1,3-cyclohexandione displaying an alkyl methyl ether group at position 5. The conformational analysis of this product showed a high preference for the trans-diaxial conformation in both solution and solid state. Such conformation was possible from the noncovalent intramolecular nX→ π*C═Ointeractions (X = an element having an unshared electron pair), allowing the determination of the interaction energies. Since the nX→ π*C═Ointeractions can be regarded as additive, the energy values ranged from 4.52 to 6.51 kcal mol–1for each carbonyl group with a strong dependency on the interatomic distances. The rigorous analysis of the electron density in the topological theory of atoms in molecules framework clearly shows that the origin of O–C═O interactions are through the nO→ π*C═Oelectron transfer mechanism. Such interactions are slightly weaker than a canonical hydrogen bond but seemingly stronger than a van der Waals interaction. This interaction must be considered as a stereoelectronic effect due the electronic transfer between the interacting groups, which are limited by their relative stereochemistry and can be represented by a bond–no bond interaction, causing the pyramidalization of the carbonyl, which is the charge acceptor group.

Published
2021
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27. Evaluation of the hepatoprotective effect of an hydroalcoholic extract of Jatropha dioicaagainst the damage induced by valproic acid in Wistar rats

Author

Tijerina-Márquez, Ramiro, Mendoza-Hernández, Oscar H., Espinosa-Cantú, César B., Rivas-Galindo, Verónica M, Moreno-Peña, Diana, Torres-González, Liliana, Muñoz-Espinosa, Linda E., Pérez-Rodríguez, Edelmiro, Cura-Esquivel, Idalia A., and Cordero-Pérez, Paula

Abstract

Liver diseases have gained importance due to their prevalence, incidence and because most chronic liver diseases have no cure, except for hepatitis C. Liver damage induced by drugs such as valproic acid (VPA) has been used to study therapeutic alternatives. Jatropha dioicamay be one of these alternatives as it has metabolites with potential antioxidant activity. The objetive of this study was to evaluate the hepatoprotective effect of a hydroalcoholic extract of J. dioicaagainst VPA-induced damage in Wistar rats.

Published
2024
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28. Synthesis of Novel Tetrahydroindeno[1,2-b]pyrrolidines via Ugi MCR and Palladium-Catalyzed Aerobic Oxidative Cyclization

Author

Tannya R. Ibarra-Rivera, Rentería-Gómez, Manuel Alejandro, Nieto-Sepúlveda, Eduardo, Gámez-Montaño, Rocío, Rivas-Galindo, Verónica M., and Hernandez-Fernandez, Eugenio

Abstract

Novel tetrahydroindeno[1,2-b]pyrrolidineswereconveniently prepared in moderate to good yields via a sequential Ugi multicomponent reaction or Staudinger/aza-Wittig/Ugi combination, followed by the palladium-catalyzed aerobic oxidative cyclization of the resulting Ugi adducts.

Published
2016
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29. Stereochemistry of a Second Riolozane and Other Diterpenoids from Jatropha dioica

Author

Melchor-Martínez, Elda M., primary, Silva-Mares, David A., additional, Torres-López, Ernesto, additional, Waksman-Minsky, Noemí, additional, Pauli, Guido F., additional, Chen, Shao-Nong, additional, Niemitz, Matthias, additional, Sánchez-Castellanos, Mariano, additional, Toscano, Alfredo, additional, Cuevas, Gabriel, additional, and Rivas-Galindo, Verónica M., additional

Published
2017
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30. Stereochemistry of a Second Riolozane and Other Diterpenoids from Jatropha dioica

Author

Melchor-Martínez, Elda M., Silva-Mares, David A., Torres-López, Ernesto, Waksman-Minsky, Noemí, Pauli, Guido F., Chen, Shao-Nong, Niemitz, Matthias, Sánchez-Castellanos, Mariano, Toscano, Alfredo, Cuevas, Gabriel, and Rivas-Galindo, Verónica M.

Abstract

The dichloromethane extract of the roots of Jatropha dioicaafforded riolozatrione (1) and a C-6 epimer of riolozatrione, 6-epi-riolozatrione (2), as a new structure and only the second reported riolozane diterpenoid. The two known diterpenoids jatrophatrione (3) and citlalitrione (4) were also isolated and characterized. Both epimers 1and 2are genuine plant constituents, with 2likely being the biosynthesis precursor of 1due to the tendency for the quantitative transformation of 2into 1under base catalysis. The structural characterization and distinction of the stereoisomers utilized 1H iterative full-spin analysis, yielding complete J-correlation maps that were represented as quantum interaction and linkage tables. The absolute configuration of compounds 1–4was established by means of vibrational circular dichroism and via X-ray diffraction analysis for 1, 2, and 4. Additionally, the cytotoxic and antiherpetic in vitro activities of the isolates were evaluated.

Published
2024
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33. Synthesis of novel tetrahydroindeno[1,2- b ]pyrrolidines via Ugi multicomponent and palladium-catalyzed aerobic oxidative cyclization.

Author

Ibarra-Rivera, Tannya R., Rentería-Gómez, Manuel Alejandro, Nieto-Sepúlveda, Eduardo, Gámez-Montaño, Rocío, Rivas Galindo, Verónica M., and Hernandez-Fernandez, Eugenio

Subjects
PYRROLIDINE, CHEMICAL synthesis, RING formation (Chemistry), PALLADIUM, CHEMICAL adducts
Abstract

Novel tetrahydroindeno[1,2-b]pyrrolidines were conveniently prepared in moderate to good yields via a sequential Ugi multicomponent reaction or Staudinger/aza-Wittig/Ugi combination, followed by the palladium-catalyzed aerobic oxidative cyclization of the resulting Ugi adducts. [ABSTRACT FROM AUTHOR]

Published
2016
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36. Microwave-Assisted Hydrolysis of Ethyl Azolylacetates and Cinnamates with K 2 CO 3 : Synthesis of Potassium Carboxylates.

Author

Hernández-Fernández J, Tiempos-Flores N, Ordóñez M, Rivas-Galindo VM, López-Cortina S, García-Alvarez KG, and Hernández-Fernández E

Abstract

In this study, the hydrolysis of ethyl azolylacetates and ethyl cinnamates using K 2 CO 3 /ethanol under microwave irradiation was developed. For this purpose, ethyl azolylacetates were first synthesized by nucleophilic substitution between the corresponding azole and ethyl bromoacetate under sonication at 50 °C for 3 h, yielding derivatives with 10-92% chemical yields, while ethyl cinnamates were obtained by a microwave-assisted Horner-Wadsworth-Emmons (HWE) reaction of triethyl phosphonoacetate with a variety of aryl aldehydes at 140 °C for 20 min, yielding derivatives with moderate to high yields (67-98%). Initially, the optimization of the hydrolysis reaction was performed using ethyl pyrazolylacetate as a model starting material while varying the temperature, time, and base equivalents; the best results were achieved by carrying out the reaction at 180 °C for 20 min with 3.0 eq of K 2 CO 3 . This simple and greener method facilitated the synthesis of potassium carboxylates in moderate to high yields, 80-98% for azolyl derivatives and 73-98% for cinnamate derivatives. The structures of all potassium carboxylates were confirmed by FTIR, 1 H, 13 C NMR, and HRMS., Competing Interests: The authors declare no competing financial interest., (© 2024 The Authors. Published by American Chemical Society.)

Published
2024
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37. Effect of the n O → π* C═O Interaction on the Conformational Preference of 1,3-Diketones: A Case Study of Riolozatrione Derivatives.

Author

Tamez-Fernández JF, Soto-Suárez FM, Estrada-Chavarría YD, Quijano-Quiñones RF, Toscano RA, Cuétara-Guadarrama F, Duarte-Alaniz V, Ibarra-Rivera TR, Quiroz-García B, Martínez-Otero D, Ramírez-Gualito K, Barquera-Lozada JE, Rivas-Galindo VM, and Cuevas G

Abstract

The cyclopropane ring-opening reaction of riolozatrione, a natural product obtained from Jatropha dioica , afforded a 2,2-disubstituted 1,3-cyclohexandione displaying an alkyl methyl ether group at position 5. The conformational analysis of this product showed a high preference for the trans -diaxial conformation in both solution and solid state. Such conformation was possible from the noncovalent intramolecular n X → π* C═O interactions (X = an element having an unshared electron pair), allowing the determination of the interaction energies. Since the n X → π* C═O interactions can be regarded as additive, the energy values ranged from 4.52 to 6.51 kcal mol -1 for each carbonyl group with a strong dependency on the interatomic distances. The rigorous analysis of the electron density in the topological theory of atoms in molecules framework clearly shows that the origin of O-C═O interactions are through the n O → π* C═O electron transfer mechanism. Such interactions are slightly weaker than a canonical hydrogen bond but seemingly stronger than a van der Waals interaction. This interaction must be considered as a stereoelectronic effect due the electronic transfer between the interacting groups, which are limited by their relative stereochemistry and can be represented by a bond-no bond interaction, causing the pyramidalization of the carbonyl, which is the charge acceptor group.

Published
2021
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38. Nuclear magnetic resonance spectroscopy data of isolated compounds from Acacia farnesiana (L) Willd fruits and two esterified derivatives.

Author

Hernández-García E, García A, Avalos-Alanís FG, Rivas-Galindo VM, Delgadillo-Puga C, and Camacho-Corona MDR

Abstract

In the present article we describe the spectroscopic data of 1 H and 13 C Nuclear Magnetic Resonance of 11 compounds including: Nine natural products from the hexanic-chloroformic and methanolic extracts of Acacia farnesiana fruit and two esterified derivatives (22E-stimasta-5,22-dien- 3β-acetyl and methyl 3,4,5-triacetyloxybenzoate). Data linked to the research work entitled "Chemical composition of fruits of Acacia farnesiana (L) Willd and its activity against Mycobacterium tuberculosis and dysentery bacteria" (Hernández et al., 2019) [1].

Published
2018
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