Resumen Histórico sobre la perezona, 1852-2022
Historical summary related to perezone, 1852-2022
Resumen
En este informe, se presenta una versión resumida sobre la historia de la perezona, molécula considerada como el primer metabolito secundario aislado en estado cristalino en el Nuevo-Mundo (hoy Continente Américano); es importante resaltar, que el manuscrito aquí exhibido es una adaptación resumida y actualizada, al año 2022, de un capítulo divulgado por nuestro grupo académico Laboratorio de Estudios sobre Química Verde, en el libro Progress in the Chemistry of Organic Natural Products (2021), en el cual se cubrió toda la información referente a la perezona para el periodo 1852-2020.
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Enríquez, R.G., Fernández-G, J.M., Gnecco, D., Pénicaud, A. & Reynolds, W.F. (1998). The crystal and molecular structure of isoperezone, aminoperezone, and isoaminoperezone: a comparative study of their crystal packing. Journal of Chemical Crystallography 28: 529-537. https://doi.org/10.1023/A:1023292005612
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Escobedo-González, R., Mendoza, P., Nicolás-Vázquez, M.I., Hernández-Rodríguez, M., Martínez, J. & Miranda Ruvalcaba, R. (2021). A timeline of perezone, the first isolated secondary metabolite in the New World, covering the period from 1852 to 2020. In Progress in the Chemistry of Organic Natural Products116: 67-133 Springer, Switerland. https://doi.org/10.1007/978-3-030-80560-9_3
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Escobedo-González, R.G., Vargas-Requena, C.L., Moyers-Montoya, E., Aceves-Hernández, J.M., Nicolás-Vázquez, M.I. & Miranda-Ruvalcaba, R. (2017). In silico study of the pharmacologic properties and cytotoxicity pathways in cancer cells of various indolylquinone analogues of perezone. Molecules 22(7): 1060. https://doi.org/10.3390/molecules22071060
Escobedo-González, R., Vázquez-Cabañas, A., Martínez-González, A., Mendoza-Sánchez, P., Saavedra-Leos, Z., Cruz-Olivares, J., Nava Serrano, J., Martínez, J. & Miranda Ruvalcaba, R. (2019). Green approach extraction of perezone from the roots of Acourtia platyphilla (A. Grey): a comparison of four activating modes and supercritical carbon dioxide. Molecules 24(17): 3035. https://doi.org/10.3390/molecules24173035
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a) Frontana, C. & González, I. (2007). Structural factors affecting the reactivity of natural α-hydroxyquinones. An electrochemical and ESR study. ECS Transactions 3(29): 13-23. https://doi.org/10.1149/1.2753287
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Hernández-Rodríguez, M., Mendoza-Sánchez, P., Macías-Perez, M.E., Rosales-Cruz, E., Mera-Jiménez, E., Nicolás-Vázquez, M.I. & Miranda-Ruvalcaba, R. (2019). In vitro and computational studies showed that perezone inhibits PARP-1 and induces changes in the redox state of K562 cells. Archives of Biochemistry and Biophysics 671: 225-234. https://doi.org/10.1016/j.abb.2019.05.002
Hernández-Rodríguez, M., Mendoza-Sánchez, P., Macías-Perez, M.E., Rosales-Cruz, E., Mera-Jiménez, E., Aceves-Hernández, J.M., Nicolás-Vázquez, M.I. & Miranda-Ruvalcaba, R. (2020). In vitro and computational studies of natural products related to perezone as anti-neoplastic agents. Biochimie 171-172: 158-169. https://doi.org/10.1016/j.biochi.2020.03.003
Hernández-Rodríguez, M., Mendoza-Sánchez, P., Macías-Perez, M.E., Rosales-Cruz, E., Mera-Jiménez, E., Żołek, T., Maciejewska, D., Nicolás-Vázquez, M.I. & Miranda-Ruvalcaba, R. (2022). Search of perezone chemically related compounds as possible anti-neoplasic agents. Medicinal Chemistry Research submitted.
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Joseph-Nathan, P., Garibay, M.E. & Santillan, R.L. (1987). BF3-catalyzed cycloadditions of naturally occurring sesquiterpene p-benzoquinones. The Journal of Organic Chemistry 52(5): 759-763. https://doi.org/10.1021/jo00381a010
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a) Joseph-Nathan, P., Hernández, J.D., Román, L.U., García, G.E. & Mendoza, V. (1982). Sesquiterpenes from Perezia carpholepis. Phytochemistry 21(3): 669-672. https://doi.org/10.1016/0031-9422(82)83162-2
b) Joseph-Nathan, P., Hernández, J.D., Román, L.U., García, E., Mendoza, V. & Mendoza, S. (1982). Coumarin and terpenoids from Perezia alamani var. oolepis. Phytochemistry 21(5): 1129-1132. https://doi.org/10.1016/S0031-9422(00)82430-9
Joseph-Nathan, P., Martínez, E., Rojas, M. & Santillan, R.L. (1987). The solid-state versus the solutions structure of 6-hydroxyperezone. Journal of Natural Products 50(5): 860-865. https://doi.org/10.1021/np50053a014
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