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Planta Med 2024; 90(12): 938-948
DOI: 10.1055/a-2381-5060
Biological and Pharmacological Activity
Original Papers

Withaphysalin Derivatives from Iochroma arborescens Induce Antiproliferative and Antimigratory Activities in vitro

Rodrigo Elísio de Sá
1   Laboratório de Cultura de Células do Delta, LCCDelta, Universidade Federal do Delta do Parnaíba, UFDPar, Parnaíba, PI, Brazil
,
Gisele Santos de Araújo
1   Laboratório de Cultura de Células do Delta, LCCDelta, Universidade Federal do Delta do Parnaíba, UFDPar, Parnaíba, PI, Brazil
,
Fabrício dos Santos Machado
1   Laboratório de Cultura de Células do Delta, LCCDelta, Universidade Federal do Delta do Parnaíba, UFDPar, Parnaíba, PI, Brazil
,
Jessica Maria Teles Souza
1   Laboratório de Cultura de Células do Delta, LCCDelta, Universidade Federal do Delta do Parnaíba, UFDPar, Parnaíba, PI, Brazil
,
Ayslan Batista Barros
1   Laboratório de Cultura de Células do Delta, LCCDelta, Universidade Federal do Delta do Parnaíba, UFDPar, Parnaíba, PI, Brazil
,
Francisco das Chagas Lima Pinto
2   Laboratório de Fitoquímica de Plantas Medicinais, Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará (UFC), Fortaleza, CE, Brazil
,
Joana Deyse Lima Agostinho
2   Laboratório de Fitoquímica de Plantas Medicinais, Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará (UFC), Fortaleza, CE, Brazil
,
Alejandro Pedro Ayala
3   Departamento de Física, Centro de Ciências, Universidade Federal do Ceará, Fortaleza, CE, Brazil
,
José Delano Barreto Marinho Filho
1   Laboratório de Cultura de Células do Delta, LCCDelta, Universidade Federal do Delta do Parnaíba, UFDPar, Parnaíba, PI, Brazil
,
Otília Deusdênia Loiola Pessoa 
2   Laboratório de Fitoquímica de Plantas Medicinais, Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará (UFC), Fortaleza, CE, Brazil
,
Ana Jérsia Araújo 
1   Laboratório de Cultura de Células do Delta, LCCDelta, Universidade Federal do Delta do Parnaíba, UFDPar, Parnaíba, PI, Brazil
› InstitutsangabenThe authors are grateful to the National Institute of Science and Technology – INCT BioNat, the National Council for Scientific and Technological Development (CNPQ), the Coordination for the Improvement of Higher Education Personnel (CAPES), and the Piauí State Research Foundation (FAPEPI).
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Erratum zu diesem Artikel:

Correction: Withaphysalin Derivatives from Iochroma arborescens Induce Antiproliferative and Antimigratory Activities in vitroPlanta Med eFirst
DOI: 10.1055/a-2407-3066

Abstract

Withanolides are steroidal lactones commonly found in plants of the Solanaceae family that have significant medicinal value. In this study, three withanolides extracted from Iochroma arborescens leaves were isolated and characterized. These included withaphysalin F (3) and two newly identified epimeric compounds: 18R- and 18S-O-methyl-withaphysalin F (1 and 2). Their structures were elucidated by NMR, IR, MS, CD, and X-ray diffraction analysis, and their potential against cell proliferation and migration was investigated. The cytotoxic assay revealed activity against different tumor and non-tumor cell lines. (18S)-O-methyl-withaphysalin F (2) presented cell death effects after at least 6 hours of exposure. MDA-MB-231 cells were exposed to 0.06 and 0.6 µM of (18S)-O-methyl-withaphysalin F (2), and reductions in cell adhesion, migration, and clonogenicity were observed. Morphological analysis revealed negative regulation in filopodia, salience, and roughness, as well as alterations in cellular microarchitecture. These results provide clues as to the effects of (18S)-O-methyl-withaphysalin F (2), allowing new molecular modifications to improve potency and selectivity and increase our antineoplastic arsenal.

Keywords

Iochroma arborescens - Solanaceae - breast cancer - cytotoxicity - withaphysalins

Supporting Information

    IR, MS, and 1D and 2D NMR spectra of compounds 1 and 2 are available as Supporting Information.

  • Ergänzendes Material


Publikationsverlauf

Eingereicht: 29. Februar 2024

Angenommen nach Revision: 01. August 2024

Artikel online veröffentlicht:
19. August 2024

© 2024. Thieme. All rights reserved.

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