Piper anisum as a promising new source of bioactive metabolites
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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.
KeywordsAntioxidant capacity Antimicrobial compounds Antitumor activity Bioactive metabolites Ethnopharmacology Metabolomics
Funding was provided by Federal University of Bahia (Project no: 11301), FAPESB, CNPq and CAPES.
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.
- Cüce M, Bekircan T, Laghari AH, Sökmen M, Sökmen A, Önay Uçar E, Kılıç AO (2017) Antioxidant phenolic constituents, antimicrobial and cytotoxic properties of Stachys annua L. From both natural resources and micropropagated plantlets. Indian J Tradit Knowl 16:407–416Google Scholar
- D’Sousa Costa C, Ribeiro P, Loureiro M, Simoes R, de Castro R, Fernandez L (2015) Phytochemical screening, antioxidant and antibacterial activities of extracts prepared from different tissues of Schinus terebinthifolius Raddi that occurs in the coast of Bahia, Brazil. Pharmacogn Mag 11:607–614CrossRefGoogle Scholar
- De Lima EJSP, Alves RG, D’Elia GMA, Da Anunciação TA, Silva VR, Santos LDS, Soares MBP, Cardozo NMD, Costa EV, Da Silva FMA, Koolen HHF, Bezerra DP (2018) Antitumor effect of the essential oil from the leaves of Croton matourensis Aubl. (Euphorbiaceae). Molecules 23:1–12Google Scholar
- Deborde C, Fontaine JX, Jacob D, Botana A, Nicaise V, Richard-Forget F, Lecomte S, Decourtil C, Hamade K, Mesnard F, Moing A, Molinié R (2019) Optimizing 1D 1H-NMR profiling of plant samples for high throughput analysis: extract preparation, standardization, automation and spectra processing. Metabolomics 15:28PubMedPubMedCentralCrossRefGoogle Scholar
- Đurđević S, Šavikin K, Živković J, Böhm V, Stanojković T, Damjanović A, Petrović S (2018) Antioxidant and cytotoxic activity of fatty oil isolated by supercritical fluid extraction from microwave pretreated seeds of wild growing Punica granatum L. J Supercrit Fluids 133:225–232CrossRefGoogle Scholar
- Ee GCL, Lim SK, Lim CM, Dzulkefly K (2008) Alkaloids and carboxylic acids from Piper nigrum. Asian J Chem 20:5931–5940Google Scholar
- Fajriah S, Megawati Hudiyono S, Kosela S, Hanafi M (2017) Chemical constituents and potential cytotoxic activity of n- hexane fraction from Myristica fatua Houtt leaves C3—AIP Conference Proceedings. 1862Google Scholar
- Islam MT, Ali ES, Uddin SJ, Shaw S, Islam MA, Ahmed MI, Chandra Shill M, Karmakar UK, Yarla NS, Khan IN, Billah MM, Pieczynska MD, Zengin G, Malainer C, Nicoletti F, Gulei D, Berindan-Neagoe I, Apostolov A, Banach M, Yeung AWK, El-Demerdash A, Xiao J, Dey P, Yele S, Jóźwik A, Strzałkowska N, Marchewka J, Rengasamy KRR, Horbańczuk J, Kamal MA, Mubarak MS, Mishra SK, Shilpi JA, Atanasov AG (2018) Phytol: a review of biomedical activities. Food Chem Toxicol 121:82–94PubMedCrossRefGoogle Scholar
- Lang G, Mayhudin NA, Mitova MI, Sun L, Van Der Sar S, Blunt JW, Cole ALJ, Ellis G, Laatsch H, Munro MHG (2008) Evolving trends in the dereplication of natural product extracts: new methodology for rapid, small-scale investigation of natural product extracts. J Nat Prod 71:1595–1599PubMedCrossRefGoogle Scholar
- Lim SM, Loh SP (2016) In vitro antioxidant capacities and antidiabetic properties of phenolic extracts from selected citrus peels. Int Food Res J 23:211–219Google Scholar
- Limmongkon A, Nopprang P, Chaikeandee P, Somboon T, Wongshaya P, Pilaisangsuree V (2018) LC-MS/MS profiles and interrelationships between the anti-inflammatory activity, total phenolic content and antioxidant potential of Kalasin 2 cultivar peanut sprout crude extract. Food Chem 239:569–578PubMedCrossRefGoogle Scholar
- Pereira EPL, Ribeiro PR, Loureiro MB, de Castro RD, Fernandez LG (2014) Effect of water restriction on total phenolics and antioxidant properties of Amburana cearensis (Fr. Allem) A.C. Smith cotyledons during seed imbibition. Acta Physiol Plant 36:1293–1297Google Scholar
- Ribeiro PR, Willems LAJ, Mutimawurugo MC, Fernandez LG, de Castro RD, Ligterink W, Hilhorst HWM (2015b) Metabolite profiling of Ricinus communis germination at different temperatures provides new insights into thermo-mediated requirements for successful seedling establishment. Plant Sci 239:180–191PubMedCrossRefGoogle Scholar
- Saleem M, Nazir M, Hussain H, Tousif MI, Elsebai MF, Riaz N, Akhtar N (2018) Natural phenolics as inhibitors of the human neutrophil elastase (HNE) release: an overview of natural anti-inflammatory discoveries during recent years. AntiInflamm Antiallerg Agents Med Chem 17:70–94CrossRefGoogle Scholar
- Santos PM, Batista DLJ, Ribeiro LAF, Boffo EF, de Cerqueira MD, Martins D, de Castro RD, de Souza-Neta LC, Pinto E, Zambotti-Villela L, Colepicolo P, Fernandez LG, Canuto GAB, Ribeiro PR (2018) Identification of antioxidant and antimicrobial compounds from the oilseed crop Ricinus communis using a multiplatform metabolite profiling approach. Ind Crops Prod 124:834–844CrossRefGoogle Scholar
- Setzer WN, Park G, Agius BR, Stokes SL, Walker TM, Haber WA (2008) Chemical compositions and biological activities of leaf essential oils of twelve species of Piper from Monteverde, Costa Rica. Nat Product Commun 3:1367–1374Google Scholar