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Article

α,β-Pipitzols and α,β-Isopipitzols from Natural Quinone Perezone: Quantum Chemistry, Docking, Chemoinformatic, and Pharmacological Studies

by
Adriana Lizbeth Rivera Espejel
1,
Joel Martínez
1,
Cristopher Williams Fuentes Cid
1,
Martha E. Macías Pérez
2,
Maricarmen Hernández Rodríguez
3,
Alejandro Fajardo De La Rosa
4,
René Miranda Ruvalcaba
1,* and
María Inés Nicolás-Vázquez
1,*
1
Departamento de Ciencias Químicas, Facultad de Estudios Superiores Cuautitlán Campo 1, Universidad Nacional Autónoma de México, Avenida 1° de Mayo s/n, Colonia Santa María las Torres, Cuautitlán Izcalli 54740, Mexico
2
Unidad de Investigación Biomédica de Zacatecas (UIBMZ) del Instituto Mexicano del Seguro Social (IMSS), Alameda Trinidad García de La Cadena 438_2436A436, Zacatecas Centro, Zacatecas 98000, Mexico
3
Laboratorio de Cultivo Celular, Escuela Superior de Medicina, Instituto Politécnico Nacional (IPN), Salvador Díaz Mirón esq. Plan de San Luis s/n, Casco de Santo Tomás, Miguel Hidalgo, Ciudad de México 11340, Mexico
4
Laboratorio de Ingeniería Química, Facultad de Química, Circuito Escolar S/N, Coyoacán, Cd. Universitaria, Ciudad de México 04510, Mexico
*
Authors to whom correspondence should be addressed.
Molecules 2026, 31(3), 469; https://doi.org/10.3390/molecules31030469
Submission received: 11 December 2025 / Revised: 8 January 2026 / Accepted: 20 January 2026 / Published: 29 January 2026
(This article belongs to the Special Issue Molecular Docking in Drug Discovery, 2nd Edition)
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Abstract

PARP-1 and COX-2 have played important roles in several carcinomas, representing potential therapeutic targets; natural products have constituted interesting alternatives in cancer research, and complementary computational methods are relevant tools for the proposal of new molecules. Therefore, in this work, a theoretical study of a set of four derivatives of perezone and isoperezone, i.e., α-pipitzol, β-pipitzol, α-isopipitzol, and β-isopipitzol, employing quantum chemistry, bioinformatics, and docking, was performed. Conformational studies were accomplished to obtain minimum energy structures. Subsequently, they were optimized by the B3LYP hybrid method and the 6-311++G(d,p) basis set. With this same level of theory, the geometrical, electronic, and spectroscopic properties and the reactivity parameters were determined; moreover, a molecular docking evaluation was performed to determine their activity towards COX-2 and PARP-1. Additionally, a cytotoxicity activity assay was performed against various cancer cell lines; thus, α-pipitzol and β-pipitzol showed the greatest affinity for COX-2, and the α-isopipitzol exhibited two relevant interactions. Regarding α-pipitzol, it exhibited both affinity and an important interaction with PARP-1. Regarding β-pipitzol, it displayed the lowest inhibitory concentration in A549 (64.49 µM); nevertheless, α-isopipitzol presented the lowest inhibitory concentrations, 83.59 µM and 87.85 µM for U37 and MCF-7 cell lines, respectively.
Keywords: pipitzols; isopipitzols; in silico; DFT; molecular docking; COX-2; PARP-1; cytotoxicity pipitzols; isopipitzols; in silico; DFT; molecular docking; COX-2; PARP-1; cytotoxicity
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MDPI and ACS Style

Rivera Espejel, A.L.; Martínez, J.; Fuentes Cid, C.W.; Macías Pérez, M.E.; Hernández Rodríguez, M.; Fajardo De La Rosa, A.; Miranda Ruvalcaba, R.; Nicolás-Vázquez, M.I. α,β-Pipitzols and α,β-Isopipitzols from Natural Quinone Perezone: Quantum Chemistry, Docking, Chemoinformatic, and Pharmacological Studies. Molecules 2026, 31, 469. https://doi.org/10.3390/molecules31030469

AMA Style

Rivera Espejel AL, Martínez J, Fuentes Cid CW, Macías Pérez ME, Hernández Rodríguez M, Fajardo De La Rosa A, Miranda Ruvalcaba R, Nicolás-Vázquez MI. α,β-Pipitzols and α,β-Isopipitzols from Natural Quinone Perezone: Quantum Chemistry, Docking, Chemoinformatic, and Pharmacological Studies. Molecules. 2026; 31(3):469. https://doi.org/10.3390/molecules31030469

Chicago/Turabian Style

Rivera Espejel, Adriana Lizbeth, Joel Martínez, Cristopher Williams Fuentes Cid, Martha E. Macías Pérez, Maricarmen Hernández Rodríguez, Alejandro Fajardo De La Rosa, René Miranda Ruvalcaba, and María Inés Nicolás-Vázquez. 2026. "α,β-Pipitzols and α,β-Isopipitzols from Natural Quinone Perezone: Quantum Chemistry, Docking, Chemoinformatic, and Pharmacological Studies" Molecules 31, no. 3: 469. https://doi.org/10.3390/molecules31030469

APA Style

Rivera Espejel, A. L., Martínez, J., Fuentes Cid, C. W., Macías Pérez, M. E., Hernández Rodríguez, M., Fajardo De La Rosa, A., Miranda Ruvalcaba, R., & Nicolás-Vázquez, M. I. (2026). α,β-Pipitzols and α,β-Isopipitzols from Natural Quinone Perezone: Quantum Chemistry, Docking, Chemoinformatic, and Pharmacological Studies. Molecules, 31(3), 469. https://doi.org/10.3390/molecules31030469

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