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Advances in the Synthesis of Lignan Natural Products
Article

Lignans from Bursera fagaroides Affect In Vivo Cell Behavior by Disturbing the Tubulin Cytoskeleton in Zebrafish Embryos

1
CONACYT-Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Cuernavaca 62209, Morelos, Mexico
2
Facultad de Ciencias, Universidad Antonio Nariño, Armenia Quindío 63003, Colombia
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Departamento de Genética del Desarrollo y Fisiología Molecular, Instituto de Biotecnología, Universidad Nacional Autónoma de México, Cuernavaca 62210, Morelos, Mexico
4
Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Cuernavaca 62209, Morelos, Mexico
5
Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Cuernavaca 62209, Morelos, Mexico
*
Authors to whom correspondence should be addressed.
Academic Editor: David Barker
Molecules 2019, 24(1), 8; https://doi.org/10.3390/molecules24010008
Received: 27 November 2018 / Revised: 13 December 2018 / Accepted: 17 December 2018 / Published: 20 December 2018
(This article belongs to the Special Issue Lignans)
By using a zebrafish embryo model to guide the chromatographic fractionation of antimitotic secondary metabolites, seven podophyllotoxin-type lignans were isolated from a hydroalcoholic extract obtained from the steam bark of Bursera fagaroides. The compounds were identified as podophyllotoxin (1), β-peltatin-A-methylether (2), 5′-desmethoxy-β-peltatin-A-methylether (3), desmethoxy-yatein (4), desoxypodophyllotoxin (5), burseranin (6), and acetyl podophyllotoxin (7). The biological effects on mitosis, cell migration, and microtubule cytoskeleton remodeling of lignans 17 were further evaluated in zebrafish embryos by whole-mount immunolocalization of the mitotic marker phospho-histone H3 and by a tubulin antibody. We found that lignans 1, 2, 4, and 7 induced mitotic arrest, delayed cell migration, and disrupted the microtubule cytoskeleton in zebrafish embryos. Furthermore, microtubule cytoskeleton destabilization was observed also in PC3 cells, except for 7. Therefore, these results demonstrate that the cytotoxic activity of 1, 2, and 4 is mediated by their microtubule-destabilizing activity. In general, the in vivo and in vitro models here used displayed equivalent mitotic effects, which allows us to conclude that the zebrafish model can be a fast and cheap in vivo model that can be used to identify antimitotic natural products through bioassay-guided fractionation. View Full-Text
Keywords: Bursera fagaroides; podophyllotoxin-type lignans; cell cycle; cell migration; epiboly; microtubules; F-actin; cancer; lignans Bursera fagaroides; podophyllotoxin-type lignans; cell cycle; cell migration; epiboly; microtubules; F-actin; cancer; lignans
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MDPI and ACS Style

Antúnez-Mojica, M.; Rojas-Sepúlveda, A.M.; Mendieta-Serrano, M.A.; Gonzalez-Maya, L.; Marquina, S.; Salas-Vidal, E.; Alvarez, L. Lignans from Bursera fagaroides Affect In Vivo Cell Behavior by Disturbing the Tubulin Cytoskeleton in Zebrafish Embryos. Molecules 2019, 24, 8. https://doi.org/10.3390/molecules24010008

AMA Style

Antúnez-Mojica M, Rojas-Sepúlveda AM, Mendieta-Serrano MA, Gonzalez-Maya L, Marquina S, Salas-Vidal E, Alvarez L. Lignans from Bursera fagaroides Affect In Vivo Cell Behavior by Disturbing the Tubulin Cytoskeleton in Zebrafish Embryos. Molecules. 2019; 24(1):8. https://doi.org/10.3390/molecules24010008

Chicago/Turabian Style

Antúnez-Mojica, Mayra, Andrés M. Rojas-Sepúlveda, Mario A. Mendieta-Serrano, Leticia Gonzalez-Maya, Silvia Marquina, Enrique Salas-Vidal, and Laura Alvarez. 2019. "Lignans from Bursera fagaroides Affect In Vivo Cell Behavior by Disturbing the Tubulin Cytoskeleton in Zebrafish Embryos" Molecules 24, no. 1: 8. https://doi.org/10.3390/molecules24010008

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