Piper anisum as a promising new source of bioactive metabolites

  • Danilo Batista
  • Patrícia Campos
  • Valdenizia R. Silva
  • Luciano de S. Santos
  • Daniel P. Bezerra
  • Milena B. P. Soares
  • Pio Colepicolo
  • Leonardo Zambotti-Villela
  • Ernani Pinto
  • Floricea M. Araújo
  • Dirceu Martins
  • Luzimar G. Fernandez
  • Wilco Ligterink
  • Gisele A. B. Canuto
  • Martins Dias de Cerqueira
  • Paulo R. RibeiroEmail author
Original Paper


Piper species are commonly used by indigenous communities to treat several gastrointestinal diseases. In China, they are also used as an active ingredient in formulae to treat cancer. The objective of the study was to perform a large-scale metabolite profiling analysis to identify bioactive compounds in Piper anisum. Antioxidant capacity was assessed by the DPPH assay and total phenolics were assessed by Folin–Ciocalteu’s method. Antimicrobial activity was assessed against several Gram-positive and Gram-negative bacteria, whereas cytotoxicity was assessed against tumor cell lines MCF-7, HCT116, HepG2 and HL-60, and non-tumor cell line MRC-5. The multiplatform metabolite profiling approach encompassed NMR, GC–MS and LC–MS analyses. P. anisum root extract showed the greatest antioxidant capacity and total phenolic content, followed by the stem and leaf extracts. P. anisum extracts showed a highly selective antimicrobial profile, being specifically active against C. albicans (MIC of 500 μg mL−1). Additionally, the root extract (50 μg mL−1) showed the highest cell inhibition percentages against tumor cell lines MCF-7 (59.5%), HCT116 (49.2%), and HepG2 (61.0%). Forty-eight metabolites were annotated by GC–MS and 27 by LC–MS. These included alkaloids, carbohydrates, fatty acids, hydrocarbons, organic acids, phenolic compounds, and terpenes. Taken together, these results showed that P. anisum root extract is a promising source of bioactive compounds.


Antioxidant capacity Antimicrobial compounds Antitumor activity Bioactive metabolites Ethnopharmacology Metabolomics 



Funding was provided by Federal University of Bahia (Project no: 11301), FAPESB, CNPq and CAPES.

Author contributions

PRR designed and supervised all experiments. The extraction, antioxidant activity assay, total phenolic quantification, and antimicrobial activity were performed by DB and PRR. Plant collection and voucher production were performed by PRR, PC, DB, WL and LGF. Cytotoxicity assays were performed by VRS, LSS, DPB, and MBPS. Nuclear magnetic resonance (NMR) analysis was performed by PRR, DB, and MDC. GC–MS and LC–MS analysis were performed by PRR, DB, GABC, PC, LZV, and EP. Data processing and metabolite identification were performed by PRR, and GABC. Statistical analysis was performed by PRR and DB. PRR and DB wrote the manuscript, whereas WL, LGF, DPB, and GABC provided suggestions to the manuscript draft.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

11696_2019_1004_MOESM1_ESM.docx (365 kb)
Supplementary material 1 (DOCX 365 KB)


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Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2019

Authors and Affiliations

  • Danilo Batista
    • 1
  • Patrícia Campos
    • 2
  • Valdenizia R. Silva
    • 3
  • Luciano de S. Santos
    • 3
  • Daniel P. Bezerra
    • 3
  • Milena B. P. Soares
    • 3
  • Pio Colepicolo
    • 4
  • Leonardo Zambotti-Villela
    • 4
  • Ernani Pinto
    • 5
  • Floricea M. Araújo
    • 1
  • Dirceu Martins
    • 1
  • Luzimar G. Fernandez
    • 2
  • Wilco Ligterink
    • 6
  • Gisele A. B. Canuto
    • 1
  • Martins Dias de Cerqueira
    • 1
  • Paulo R. Ribeiro
    • 1
    • 2
    Email author
  1. 1.Metabolomics Research Group, Departamento de Química Orgânica, Instituto de QuímicaUniversidade Federal da BahiaSalvadorBrazil
  2. 2.Laboratório de Bioquímica, Biotecnologia e Bioprodutos, Departamento de Bioquímica e BiofísicaUniversidade Federal da BahiaSalvadorBrazil
  3. 3.Instituto Gonçalo MonizFundação Oswaldo CruzSalvadorBrazil
  4. 4.Departamento de Bioquímica, Instituto de QuímicaUniversidade de São PauloSão PauloBrazil
  5. 5.Faculdade de Ciências FarmacêuticasUniversidade de São PauloSão PauloBrazil
  6. 6.Wageningen Seed Lab, Laboratory of Plant PhysiologyWageningen University (WU)WageningenThe Netherlands

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