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Article

Green Contributions to the Chemistry of Perezone and Oxidation of the Double Bond of the Side Chain: A Theoretical Study and Cytotoxic Evaluation in MDA-MB231 Cells

by
René Gerardo Escobedo-González
1,*,
Joel Martínez
2,
Adriana L. Rivera-Espejel
2,
Claudia L. Vargas-Requena
3,
María Inés Nicolás-Vázquez
2 and
René Miranda Ruvalcaba
2,*
1
Department of Industrial Maintenance and Nanotechnology, Technological University of Juarez City, City of Juarez 32695, Chihuahua State, Mexico
2
Departamento de Ciencias Químicas, Facultad de Estudios Superiores Cuautitlán Campo 1, Universidad Nacional Autónoma de México, Cuautitlán Izcalli 54740, State of Mexico, Mexico
3
Institute of Biomedical Science, Autonomous University of the City of Juarez (UACJ), City of Juarez 32315, Chihuahua State, Mexico
*
Authors to whom correspondence should be addressed.
Molecules 2025, 30(23), 4603; https://doi.org/10.3390/molecules30234603
Submission received: 13 October 2025 / Revised: 28 November 2025 / Accepted: 28 November 2025 / Published: 30 November 2025
(This article belongs to the Special Issue Synthesis, Bioactivity and Structure–Activity Relationship of Natural Products and Their Derivatives)
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Abstract

Perezone, a sesquiterpene quinone, was the first natural product isolated in crystalline form on the American continent in 1852. It is commonly found in the roots of herbs from the Acourtia species (formerly Perezia). This molecule, along with its synthetic isomer isoperezone, exhibits antineoplastic effects, among others. In this study, an enzymatic reaction (green chemistry) was employed to oxidize the C12−C13 double bond of perezone and isoperezone. This method proved to be more effective than traditional toxic chemical oxidants. As result, epoxides were obtained, followed by acetonides, diols, and esters. All compounds were successfully synthesized and characterized using standard spectroscopic techniques. In breast cancer cell tests, the isoperezone acetonide showed the highest cytotoxicity, with an IC50 of 8.44 µM. Additionally, a computational study was performed at the DFT (B3LYP) level of theory, indicating that the geometrical and energy differences between 6-R and 6-S stereoisomers are 0.5 kcal/mol, and the spectroscopic and electronic properties aligned with the experimental data. Finally, molecular docking revealed binding energies of −8.14 kcal/mol for 6-R and −8.04 kcal/mol for 6-S, with a hydrogen bond of 2.9 Å involving the His121 residue. A chemoinformatic prediction was also conducted to compare cytotoxicity results.
Keywords: green approach; perezone-isoperezone; DFT study; antineoplastic compounds; molecular docking; chemoinformatic study green approach; perezone-isoperezone; DFT study; antineoplastic compounds; molecular docking; chemoinformatic study

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MDPI and ACS Style

Escobedo-González, R.G.; Martínez, J.; Rivera-Espejel, A.L.; Vargas-Requena, C.L.; Nicolás-Vázquez, M.I.; Miranda Ruvalcaba, R. Green Contributions to the Chemistry of Perezone and Oxidation of the Double Bond of the Side Chain: A Theoretical Study and Cytotoxic Evaluation in MDA-MB231 Cells. Molecules 2025, 30, 4603. https://doi.org/10.3390/molecules30234603

AMA Style

Escobedo-González RG, Martínez J, Rivera-Espejel AL, Vargas-Requena CL, Nicolás-Vázquez MI, Miranda Ruvalcaba R. Green Contributions to the Chemistry of Perezone and Oxidation of the Double Bond of the Side Chain: A Theoretical Study and Cytotoxic Evaluation in MDA-MB231 Cells. Molecules. 2025; 30(23):4603. https://doi.org/10.3390/molecules30234603

Chicago/Turabian Style

Escobedo-González, René Gerardo, Joel Martínez, Adriana L. Rivera-Espejel, Claudia L. Vargas-Requena, María Inés Nicolás-Vázquez, and René Miranda Ruvalcaba. 2025. "Green Contributions to the Chemistry of Perezone and Oxidation of the Double Bond of the Side Chain: A Theoretical Study and Cytotoxic Evaluation in MDA-MB231 Cells" Molecules 30, no. 23: 4603. https://doi.org/10.3390/molecules30234603

APA Style

Escobedo-González, R. G., Martínez, J., Rivera-Espejel, A. L., Vargas-Requena, C. L., Nicolás-Vázquez, M. I., & Miranda Ruvalcaba, R. (2025). Green Contributions to the Chemistry of Perezone and Oxidation of the Double Bond of the Side Chain: A Theoretical Study and Cytotoxic Evaluation in MDA-MB231 Cells. Molecules, 30(23), 4603. https://doi.org/10.3390/molecules30234603

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