Rotenoids from the Roots of Vicia faba L. (Fabaceae): Structural Characterization, Cytotoxic Effects, and Molecular Docking

Author(s)

Sipoloni, Victor Menezes ; Silva-Silva, Joao Victor ; Ferreira, Elthon G. ; Lee, Eric Yoshitaka ; Batista Junior, Joao Marcos ; Uemi, Miriam ; de Medeiros, Livia Soman ; Jimenez, Paula C. ; Veiga, Thiago A. M.

• Document type: Journal article
• Source: CHEMISTRY & BIODIVERSITY; v. N/A, p. 15-pg., 2025-05-26.

Abstract

The chemical study of the ethanolic extract from the roots of Vicia faba led to the isolation of two isoflavonoids, alfalone and 8-O-methylretusine, as well as a mixture of rotenoids, including clitoriacetal and clitoriacetal B, the latter of which is reported for the first time. These compounds were characterized through nuclear magnetic resonance and vibrational circular dichroism spectroscopies, and density functional theory calculations. The rotenoid mixture exhibited cytotoxic activity against HCT-116, MCF-7, and 501Mel cell lines, while showing no significant toxicity to NIH/3T3 cells. The predictive analysis identified several shared therapeutic targets across colorectal cancer, breast cancer, and melanoma. Key sites, including hypoxia-inducible factor 1-alpha (HIF1A), estrogen receptor, heat shock protein HSP 90-beta, and heat shock protein HSP 90-alpha, were highlighted for their critical roles in tumor progression and therapeutic resistance. Notably, clitoriacetal demonstrated an affinity for HIF1A, suggesting its involvement in the observed antitumor effects, likely through modulation of the HIF1A pathway. These findings underscore the potential of V. faba root-derived compounds as promising candidates for targeted cancer therapies. (AU)

• FAPESP's process: 24/17686-7 - Stereochemistry of furofuran lignans from optical rotatory dispersion: interplay between theory and experiment
• Grantee: Eric Yoshitaka Lee
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• FAPESP's process: 23/00242-6 - Pharmacokinetic and Biological Properties Evaluation of Drug Candidates
• Grantee: João Victor da Silva e Silva
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 23/12475-5 - Systematizing chiroptical properties of lignans: implications for correct absolute configuration assignments
• Grantee: João Marcos Batista Junior
• Support Opportunities: Regular Research Grants
• FAPESP's process: 22/12654-4 - Marine myxobacteria from the state of São Paulo as a source of protease inhibitors
• Grantee: Paula Christine Jimenez
• Support Opportunities: BIOTA-FAPESP Program - Regular Research Grants
• FAPESP's process: 18/04095-0 - Analytical Approaches for Discovering Unknown Cytotoxic Compounds from Plants
• Grantee: Thiago André Moura Veiga
• Support Opportunities: Regular Research Grants