Abstract
In the current study, the chemical composition of Baccharis spicata (Lam.) Baill. and B. punctulata DC., Asteraceae, aerial parts’ volatile oils were analysed. A higher proportion of monoterpenes than sesquiterpenes was detected in oils of inflorescence of both species. In contrast, a dominance of sesquiterpene components above the monoterpenes was found in the vegetative organs. β-Pinene, limonene, spathulenol and caryophyllene oxide were among the most abundant components along with (−)-alismol, only detected in B. punctulata and described for the first time in Baccharis oils. Storage at room temperature produced considerable changes in both oils’ composition, due to chemical transformation of terpenoids. Cytotoxic and trypanocidal activity of B. spicata and B. punctulata inflorescence volatile oils were evaluated. Bioactivity-guided fractionation yielded five active fractions for each species which effectively inhibited Trypanosoma cruzi epimastigote growth in a concentration-dependent manner (IC50 between 2.15 and 12.49 μg/ml). In order to compare the trypanocidal activity and the cytotoxicity of volatile oils for HepG2/C3A cells, the selectivity index was estimated. All samples showed to be more effective against parasites than human cells, with the selectivity index above 2.0. Among the fractions tested, samples enriched in alismol, spathulenol and caryophyllene oxide were the most active and selective against epimastigote forms.
Graphical abstract
References
Adams RP (2007) Identification of essential oil components by gas chromatography/mass spectrometry. Allured Publishing Corporation, 4th Ed. ISBN 978-1-932633-21-4.
Besten MA, Jasinski VCG, Costa AL, Nunes C, Sens DS, Wisniewski SL, Simionatto E, Riva D, Dalmarco JB, Granato D (2012) Chemical composition similarity between the essential oils isolated from male and female specimens of each five Baccharis species. J Braz Chem Soc 23:1041–1047. https://doi.org/10.1590/S0103-50532012000600007
Budel JM, Wang M, Raman V, Zhao J, Khan SI, Rehman JU, Techen N, Tekwani B, Monteiro LM, Heiden G, Takeda IJM, Farago PV, Khan IA (2018) Essential oils of five Baccharis species: investigations on the chemical composition and biological activities. Molecules 23:2620. https://doi.org/10.3390/molecules23102620
Bulhões Portapilla G, Pereira LM, Soldi RA, Gama Abreu P, Lage Gallo I, Clososki G, de Albuquerque S (2020) Activity of β-caryophyllene oxide derivatives against Trypanosoma cruzi, mammalian cells, and horseradish peroxidase. Rev Bras Farmacogn 30:824–831. https://doi.org/10.1007/s43450-020-00118-1
Castro de Morais M, de Souza J, da Silva C, Bezerra Filho M, Santana Dolabella S, de Sousa D (2020) Trypanocidal essential oils: a review. Molecules 25:4568. https://doi.org/10.3390/molecules25194568
da Silva TB, Alencar Menezes LR, Chaves Sampaio MF, Santana Meira C, Teixeira Guimarães E, Pereira Soares MB, do Nascimento Prata AP, de Lima Nogueira PC, Vilaça Costa E (2013) Chemical composition and anti-Trypanosoma cruzi activity of essential oils obtained from leaves of Xylopia frutescens and X. laevigata (Annonaceae). Nat Prod Commun 8:403–406. https://doi.org/10.1177/1934578X1300800332
Ferretti AC, Tonucci FM, Hidalgo F, Almada E, Larocca MC, Favre C (2016) AMPK and PKA interaction in the regulation of survival of liver cancer cells subjected to glucose starvation. Oncotarget 7:17815-17828. https://doi.org/10.18632/oncotarget.7404
Gonzalez MD (2019) Chemical composition of the leaf oil from Baccharis punctulata DC. at two phenological stages. J Essent Oil Res 31:573–581. https://doi.org/10.1080/10412905.2019.1612472
Konig WA, Bolow N, Fricke C, Melching S, Rieck A, Mijhle H (1996) The sesquiterpene constituents of the liverwort Preissia quadrata. Phytochemistry 43:629–633. https://doi.org/10.1016/0031-9422(96)00354-8
Lidani KCF, Andrade FA, Bavia L, Damasceno FS, Beltrame MH, Messias-Reason IJ, Sandri TL (2019) Chagas disease: from discovery to a worldwide health problem. Front Public Health 7:166. https://doi.org/10.3389/fpubh.2019.00166
Martins A, Hajdú Z, Vasas A, Csupor-Löffler B, Molnár J, Hohmann J (2010) Spathulenol inhibit the human ABCB1 efflux pump. Planta Med 76:P608. https://doi.org/10.1055/s-0030-1264906
Miller DR (2006) Ethanol and α-pinene: attractant kairomones for some large wood-boring beetles in southeastern USA. J Chem Ecol 32:779–794. https://doi.org/10.1007/s10886-006-9037-8
Minteguiaga M, Gonzalez A, Cassel E, Umpierrez N, Farina L, Dellacassa E (2018) Volatile constituents from Baccharis spp. L. (Asteraceae): chemical support for the conservation of threatened species in Uruguay. Chem Biodivers 15:e1800017. https://doi.org/10.1002/cbdv.201800017
Nocito I, Castelli MV, Zacchino Z, Serra E (2007) Activity of 8.O.4′-neolignans against Trypanosoma cruzi. Parasitol Res 101:1453–1457. https://doi.org/10.1007/s00436-007-0657-x
Ramos Campos F, Bressan J, Godoy Jasinski VC, Zuccolotto T, da Silva LE, Bonancio Cerqueira L (2016)Baccharis (Asteraceae): chemical constituents and biological activities. Chem Biodivers 13:1–17. https://doi.org/10.1002/cbdv.201400363
Saad N, Muller CD, Lobstein A (2013) Major bioactivities and mechanism of action of essential oils and their components. Flavour Fragr J 28:269–279. https://doi.org/10.1002/ffj.3165
Saeidnia S, Gohari A, Haddadi A (2013) Biogenic trypanocidal sesquiterpenes: lead compounds to design future trypanocidal drugs - a mini review. DARU J Pharm Sci 21:35. https://doi.org/10.1186/2008-2231-21-35
Schossler P, Schneider GL, Wunsch D, Soares G L G, Zini CA (2009) Volatile compounds of Baccharis punctulata, Baccharis dracunculifolia and Eupatorium laevigatum obtained using solid phase microextraction and hydrodistillation. J Braz Chem Soc 20:277–287. https://doi.org/10.1590/S0103-50532009000200012
Acknowledgements
The authors would like to thank Andres Gauna for his significant technical help.
Funding
This work was supported by funds from Agencia Nacional de Promoción Cientifica y Tecnológica [grant number PICT 2018-0197] and Universidad Nacional de Rosario [grants number 80020180300046UR and 80020190300135UR].
Author information
Authors and Affiliations
Contributions
MDF contributed to the plant material collection, extraction and chemical assays. AF, IN, MSS and GRB participated in the experimental biological assays. ELL and MLM conceived, designed and contributed to the formal analysis of the study. MVR participated in the analyses and interpretation of the data. The first draft of the manuscript was written by ELL and MLM, and all authors commented on this version. All authors have read the final manuscript and approved the submission.
Corresponding author
Ethics declarations
Conflict of Interest
The authors declare no competing interests.
Supplementary Material
ESM 1
Chemical compositions of VOs, trypanocidal and cytotoxic activities, spectroscopic data of alismol (1H and 13C NMR spectra), MS and micrograph of treated and untreated parasite (at epimastigote stage) are available as Supplementary material. (PDF 438 kb)
Rights and permissions
About this article
Cite this article
Ferretti, M.D., Rodriguez, M.V., Ferretti, A. et al. Antiprotozoal Effect of Baccharis spicata and B. punctulata Volatile Oils and Their Active Components Against Trypanosoma cruzi. Rev. Bras. Farmacogn. 32, 133–138 (2022). https://doi.org/10.1007/s43450-021-00226-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s43450-021-00226-6