UHPLC-DAD-HRMS² Characterization of Novel Dihydrochalcone Conjugates From the Antiviral Mansoa hirsuta Extracts: Diagnostic Fragmentation Pathways and Dereplication of Oligomeric Polyphenols.
5 affiliations
- 1Programa de Pós-graduação em Ciências Farmacêuticas, Escola de Farmácia, Universidade Federal de Ouro Preto, Ouro Preto, Minas Gerais, Brazil.
- 2Departamento de Ciências Biológicas, ICEB, Universidade Federal de Ouro Preto, Ouro Preto, Minas Gerais, Brazil.
- 3Instituto de Ciências Biológicos, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais, Brazil.
- 4Divisão de Química Orgânica, Instituto de Química, Universidade de Brasília, Brasília, Distrito Federal, Brazil.
- 5Laboratório de Química de Produtos Naturais Bioativos, Instituto René Rachou, Fundação Oswaldo Cruz, Belo Horizonte, Minas Gerais, Brazil.
Abstract
High-resolution mass spectrometry (HRMS) coupled with ultra-high-performance liquid chromatography (UHPLC) enables rapid characterization of complex polyphenolic constituents in medicinal plants. Mansoa hirsuta (Bignoniaceae), a neotropical liana traditionally used to treat infectious diseases, remains poorly characterized chemically. This study reports the comprehensive UHPLC-DAD-HRMS/MS profiling of ethanolic extracts from leaves, stems, and fruits, leading to the identification of 57 phenolic compounds, including 40 previously unreported flavonoid conjugates. Accurate mass measurements and diagnostic MS/MS fragmentation patterns enabled the structural characterization of five classes of dihydrochalcone-derived metabolites: dihydrochalcone-tyramine, -flavanone (mansoin-type), -flavan-3-ol, and -flavonol conjugates. Characteristic fragment ions, particularly those corresponding to the dihydrochalcone core and tyramine moiety, supported the annotation of novel oligomeric flavonoids. Organ-specific metabolite distribution revealed leaves enriched in Mansoin A-type heterotrimers, stems containing phenylethanoid glycosides and cinnamoyl-mangiferins, and fruits predominated by simpler dihydrochalcone-tyramine conjugates. All extracts exhibited low cytotoxicity (CC₅₀ > 400 μg mL⁻¹) and selective antiviral activity against Zika (ZIKV), chikungunya (CHIKV), Mayaro (MAYV), and dengue virus serotype 2 (DENV-2). The stem extract showed the highest selectivity against ZIKV (SI > 25.5), whereas the fruit extract displayed the greatest potency against DENV-2 (EC₅₀ = 25.4 ± 1.2 μg mL⁻¹; SI > 19.7). These findings expand the phytochemical knowledge of M. hirsuta, demonstrate the utility of HRMS-based metabolite profiling for dereplication of complex flavonoids, and provide diagnostic MS/MS fragmentation patterns applicable to the characterization of related oligomeric flavonoids in other plant species.
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BibTeX
@article{reis2026uhplcdadhrms²,
title = {{UHPLC-DAD-HRMS² Characterization of Novel Dihydrochalcone Conjugates From the Antiviral Mansoa hirsuta Extracts: Diagnostic Fragmentation Pathways and Dereplication of Oligomeric Polyphenols.}},
author = {Adriana Cotta Cardoso Reis and Breno de Mello Silva and Cíntia Lopes de Brito Magalhães and Erna G Kroon and Douglas da Costa Gontijo and Markus Kohlhoff and Geraldo Célio Brandão},
journal = {Journal of mass spectrometry : JMS},
year = {2026},
month = nov,
doi = {10.1002/jms.70128},
url = {https://europepmc.org/article/MED/42968445},
note = {CC BY},
}
RIS
TY - JOUR
TI - UHPLC-DAD-HRMS² Characterization of Novel Dihydrochalcone Conjugates From the Antiviral Mansoa hirsuta Extracts: Diagnostic Fragmentation Pathways and Dereplication of Oligomeric Polyphenols.
AU - Adriana Cotta Cardoso Reis
AU - Breno de Mello Silva
AU - Cíntia Lopes de Brito Magalhães
AU - Erna G Kroon
AU - Douglas da Costa Gontijo
AU - Markus Kohlhoff
AU - Geraldo Célio Brandão
PY - 2026
DA - 2026/11/01
JO - Journal of mass spectrometry : JMS
DO - 10.1002/jms.70128
UR - https://europepmc.org/article/MED/42968445
AB - High-resolution mass spectrometry (HRMS) coupled with ultra-high-performance liquid chromatography (UHPLC) enables rapid characterization of complex polyphenolic constituents in medicinal plants. Mansoa hirsuta (Bignoniaceae), a neotropical liana traditionally used to treat infectious diseases, remains poorly characterized chemically. This study reports the comprehensive UHPLC-DAD-HRMS/MS profiling of ethanolic extracts from leaves, stems, and fruits, leading to the identification of 57 phenolic compounds, including 40 previously unreported flavonoid conjugates. Accurate mass measurements and diagnostic MS/MS fragmentation patterns enabled the structural characterization of five classes of dihydrochalcone-derived metabolites: dihydrochalcone-tyramine, -flavanone (mansoin-type), -flavan-3-ol, and -flavonol conjugates. Characteristic fragment ions, particularly those corresponding to the dihydrochalcone core and tyramine moiety, supported the annotation of novel oligomeric flavonoids. Organ-specific metabolite distribution revealed leaves enriched in Mansoin A-type heterotrimers, stems containing phenylethanoid glycosides and cinnamoyl-mangiferins, and fruits predominated by simpler dihydrochalcone-tyramine conjugates. All extracts exhibited low cytotoxicity (CC₅₀ > 400 μg mL⁻¹) and selective antiviral activity against Zika (ZIKV), chikungunya (CHIKV), Mayaro (MAYV), and dengue virus serotype 2 (DENV-2). The stem extract showed the highest selectivity against ZIKV (SI > 25.5), whereas the fruit extract displayed the greatest potency against DENV-2 (EC₅₀ = 25.4 ± 1.2 μg mL⁻¹; SI > 19.7). These findings expand the phytochemical knowledge of M. hirsuta, demonstrate the utility of HRMS-based metabolite profiling for dereplication of complex flavonoids, and provide diagnostic MS/MS fragmentation patterns applicable to the characterization of related oligomeric flavonoids in other plant species.
SN - 1076-5174
SN - 1096-9888
ER -