title: Retro-Curcuminoids as Mimics of Dehydrozingerone and Curcumin: Synthesis, NMR, X-ray, and Cytotoxic Activity.
abstract: Curcumin and its derivatives have been extensively studied for their remarkable medicinal properties, and their chemical synthesis has been an important step in the optimization of well-controlled laboratory production. A family of new compounds that mimic the structure of curcumin and curcuminoids, here namedretro-curcuminoids (7-14), was synthesized and characterized using 1D ¹H- and13C-NMR, IR, and mass spectrometry; the X-ray structure of7,8,9,10,12,13, and14are reported here for the first time. The main structural feature of these compounds is the reverse linkage of the two aromatic moieties, where the acid chloride moiety is linked to the phenolic group while preserving α, β-unsaturated ketone functionality. The cytotoxic screening of7,8,9, and10at 50 and 10 µg/mL was carried out with human cancer cell lines K562, MCF-7, and SKLU-1. Lipid peroxidation on rat brain was also tested for compounds7and10. Compounds7,8, and10showed relevant cytotoxic activity against these cancer cell lines, and10showed a protective effect against lipid peroxidation. The molecular resemblance to curcuminoids and analogs withorthosubstituents suggests a potential source of useful bioactive compounds.
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, D.F. C.P. 04510, Mexico. obregonmendoza@yahoo.com.mx.
authors.forename: Marco A
authors.initials: MA
authors.lastname: Obregón-Mendoza
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, D.F. C.P. 04510, Mexico. mirianestevezc@gmail.com.
authors.forename: María Mirian
authors.initials: MM
authors.lastname: Estévez-Carmona
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, D.F. C.P. 04510, Mexico. shernandezortega@gmail.com.
authors.forename: Simón
authors.initials: S
authors.lastname: Hernández-Ortega
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, D.F. C.P. 04510, Mexico. soriano@unam.mx.
authors.forename: Manuel
authors.initials: M
authors.lastname: Soriano-García
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, D.F. C.P. 04510, Mexico. mtrapan@yahoo.com.mx.
authors.forename: María Teresa
authors.initials: MT
authors.lastname: Ramírez-Apan
authors.affiliation: Centro de Química, Benemérita Universidad Autónoma de Puebla, Puebla C.P. 72570, Mexico. maria.orea@correo.buap.mx.
authors.forename: Laura
authors.initials: L
authors.lastname: Orea
authors.affiliation: Centro de Química, Benemérita Universidad Autónoma de Puebla, Puebla C.P. 72570, Mexico. iken18@hotmail.com.
authors.forename: Hugo
authors.initials: H
authors.lastname: Pilotzi
authors.affiliation: Centro de Química, Benemérita Universidad Autónoma de Puebla, Puebla C.P. 72570, Mexico. gneccod@yahoo.com.mx.
authors.forename: Dino
authors.initials: D
authors.lastname: Gnecco
authors.affiliation: Departamento de Sistemas Biológicos, Universidad Autónoma Metropolitana, Unidad Xochimilco, México, D.F. C.P. 04960, Mexico. cassani@correo.xoc.uam.mx.
authors.forename: Julia
authors.initials: J
authors.lastname: Cassani
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, D.F. C.P. 04510, Mexico. enriquezhabib@gmail.com.
authors.forename: Raúl G
authors.initials: RG
authors.lastname: Enríquez
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D003373:Coumaric Acids / Q000737:chemistry; D018360:Crystallography, X-Ray; D003474:Curcumin / Q000031:analogs & derivatives*; D006801:Humans; D061986:MCF-7 Cells; D008297:Male; D019906:Nuclear Magnetic Resonance, Biomolecular; D051381:Rats; D017208:Rats, Wistar; D013343:Styrenes / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D003373:Coumaric Acids; D013343:Styrenes; C052933:methyl-3-methoxy-4-hydroxystyryl ketone; C004999:ferulic acid; D003474:Curcumin
keywords: curcumin; curcuminoid; dehydrozingerone; retro-curcuminoids; α,β-unsaturated-ketone