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This is an early access version, the complete PDF, HTML, and XML versions will be available soon.
Article

Organ-Specific Distribution of Antimycobacterial Neolignans in Piper rivinoides and UHPLC-HRMS/MS Analysis of Its Extracts

by
Jéssica Sales Felisberto
1,2,
Thayssa Ferreira Fagundes
2,3,
Lorraynne Oliveira-Souza
1,2,
Bruno Henrique Gomes de Souza
1,
Daniel Machado de Brito
1,2,
Jeferson Adriano Assunção
2,3,
Samik Lourenço Massau
2,
Marlon H. de Araújo
4,
Michelle Frazão Muzitano
4,
Sanderson Dias Calixto
3,
Thatiana Lopes Biá Ventura Simão
3,
Andre Mesquita Marques
5,
Ygor Jessé Ramos
1,6,* and
Davyson de Lima Moreira
1,2,7,*
1
Postgraduate Program in Plant Biology, Institute of Biology Roberto Alcantara Gomes, State University of Rio de Janeiro, São Francisco Xavier, Rio de Janeiro 20950-000, RJ, Brazil
2
Botanical Garden Research Institute of Rio de Janeiro, Rua Pacheco Leão, 915, Jardim Botânico, Rio de Janeiro 22460-030, RJ, Brazil
3
Recenor Biology Laboratory, Center of Biosciences and Biotechnology, State University of North Fluminense Darcy Ribeiro, Rua Alberto Lamego, 2000, Campos dos Goytacazes 28013-602, RJ, Brazil
4
Laboratory of Bioatives Products, Institute of Pharmaceutical Sciences, Federal University of Rio de Janeiro, Rua Alcides da Conceição, 159, Macaé 27933-378, RJ, Brazil
5
Laboratory of Technology for Biodiversity in Health/TecBio, Farmanguinhos, Oswaldo Cruz Foundation, Rua Sizenando Nabuco, 100, Manguinhos, Rio de Janeiro 21041-250, RJ, Brazil
6
Farmácia da Terra Laboratory, Faculty of Pharmacy, Federal University of Bahia, Rua Barão de Jeremoabo, 147, Ondina, Salvador 40170-115, BA, Brazil
7
Postgraduate Program in Translational Research in Drugs and Medicines, Pharmaceutical Technology Institute, Farmanguinhos, Fiocruz, Rua Sizenando Nabuco, 100, Manguinhos, Rio de Janeiro 21041-250, RJ, Brazil
*
Authors to whom correspondence should be addressed.
Molecules 2025, 30(24), 4682; https://doi.org/10.3390/molecules30244682 (registering DOI)
Submission received: 30 September 2025 / Revised: 26 November 2025 / Accepted: 4 December 2025 / Published: 6 December 2025
(This article belongs to the Section Natural Products Chemistry)
Versions Notes

Abstract

This multidisciplinary study investigates Piper rivinoides, a Brazilian medicinal species, focusing on its chemical composition and antimycobacterial potential. UHPLC-HRMS/MS of leaves, stems, branches, and roots revealed 58 compounds, including neolignans, lignanamides, triterpenes, flavonoids, and carotenoids. Fourteen metabolites, notably benzofuran neolignans and pentacyclic triterpenes are annotated here for the first time. Quantitative analyses by HPLC-DAD-UV showed that eupomatenoid-5, eupomatenoid-6, and conocarpan were most abundant in leaves, reaching amounts approximately twice those found in branches and stems and about ten times higher than in roots, supporting the optimal defense theory and organ-specific accumulation of bioactive metabolites. Biological assays against Mycobacterium tuberculosis strains H37Rv and M299 revealed strong inhibitory activity for the leaf extract and isolated neolignans. Eupomatenoid-5 and eupomatenoid-6 achieved inhibition comparable to rifampicin, with low MIC50 values, while conocarpan exhibited moderate activity. Antimycobacterial effects were more pronounced against the H37Rv strain, although relevant inhibition was also observed for the hypervirulent M299 strain. These findings highlight P. rivinoides as a rich source of benzofuran neolignans and promising antimycobacterial properties. The integration of advanced mass spectrometric analyses with bioassays demonstrates the value of combining chemical and biological approaches to uncover novel natural products. The putative identification of new neolignans and triterpenes, along with the confirmation of potent antimycobacterial activity, provides a robust foundation for further studies on biosynthesis, structure–activity relationships, and potential biotechnological applications.
Keywords: Piperaceae; antimycobacterials; LC-MS/MS; LC-DAD-UV; atlantic forest Piperaceae; antimycobacterials; LC-MS/MS; LC-DAD-UV; atlantic forest

Share and Cite

MDPI and ACS Style

Felisberto, J.S.; Fagundes, T.F.; Oliveira-Souza, L.; Souza, B.H.G.d.; Brito, D.M.d.; Assunção, J.A.; Massau, S.L.; Araújo, M.H.d.; Muzitano, M.F.; Calixto, S.D.; et al. Organ-Specific Distribution of Antimycobacterial Neolignans in Piper rivinoides and UHPLC-HRMS/MS Analysis of Its Extracts. Molecules 2025, 30, 4682. https://doi.org/10.3390/molecules30244682

AMA Style

Felisberto JS, Fagundes TF, Oliveira-Souza L, Souza BHGd, Brito DMd, Assunção JA, Massau SL, Araújo MHd, Muzitano MF, Calixto SD, et al. Organ-Specific Distribution of Antimycobacterial Neolignans in Piper rivinoides and UHPLC-HRMS/MS Analysis of Its Extracts. Molecules. 2025; 30(24):4682. https://doi.org/10.3390/molecules30244682

Chicago/Turabian Style

Felisberto, Jéssica Sales, Thayssa Ferreira Fagundes, Lorraynne Oliveira-Souza, Bruno Henrique Gomes de Souza, Daniel Machado de Brito, Jeferson Adriano Assunção, Samik Lourenço Massau, Marlon H. de Araújo, Michelle Frazão Muzitano, Sanderson Dias Calixto, and et al. 2025. "Organ-Specific Distribution of Antimycobacterial Neolignans in Piper rivinoides and UHPLC-HRMS/MS Analysis of Its Extracts" Molecules 30, no. 24: 4682. https://doi.org/10.3390/molecules30244682

APA Style

Felisberto, J. S., Fagundes, T. F., Oliveira-Souza, L., Souza, B. H. G. d., Brito, D. M. d., Assunção, J. A., Massau, S. L., Araújo, M. H. d., Muzitano, M. F., Calixto, S. D., Simão, T. L. B. V., Marques, A. M., Ramos, Y. J., & Moreira, D. d. L. (2025). Organ-Specific Distribution of Antimycobacterial Neolignans in Piper rivinoides and UHPLC-HRMS/MS Analysis of Its Extracts. Molecules, 30(24), 4682. https://doi.org/10.3390/molecules30244682

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