Abstract
Coumarins from Pterocaulon balansae Chodat, Asteraceae, have received increasing attention due to their biological activities, especially for the treatment of skin disorders. This study aimed to develop and validate high-performance and ultra-fast liquid chromatography methods for the analytical determination of coumarins in extracts, in topical formulations, as well as in porcine skin after in vitro permeation/retention studies. The chromatographic conditions consisted of a mobile phase with 0.1% formic acid (A) and acetonitrile (B) using a gradient elution; the flow rate and a column oven temperature: HPLC-UV, 1 ml min−1; 30 °C and UFLC-DAD, 0.55 ml min−1; 55 °C for 45 min and 8 min, respectively. The chemical marker 5-methoxy-6,7-methylenedioxycoumarin was used for the construction of the linearity curve in a concentration range from 0.1 to 7.5 μg ml−1. A low matrix effect was observed. The method robustness was confirmed using the Plackett-Burman experimental design. These methodologies proved to be linear, precise, and accurate for the determination of seven coumarins in analytical and bioanalytical samples in both approaches. However, UFLC analysis time was shortened to about one-fourth the time and consumes significantly less eluent, being more eco-friendly in comparison with HPLC.
Graphical abstract
Similar content being viewed by others
References
Bidone J, Argenta DF, Kratz J, Pettenuzzo LF, Horn AP, Koester LS, Bassani VL, Simões CMO, Teixeira HF (2015) Antiherpes activity and skin/mucosa distribution of flavonoids from Achyrocline satureioides extract incorporated into topical nanoemulsions. Biomed Res Int 2015:1–7. https://doi.org/10.1155/2015/238010
Bucar F, Wube A, Schmid M (2013) Natural product isolation – how to get from biological material to pure compounds. Nat Prod Rep 30:525–545. https://doi.org/10.1039/c3np20106f
EMA (2012) EMEA/CHMP/EWP/192217/2009, Guideline on bioanalytical method validation, European Medicines Agency Guideline, 1–22
Fasolo D, Bassani VL, Teixeira HF (2009) Development of topical nanoemulsions containing quercetin and 3-O-methylquercetin. Pharmazie 64:726–730
FDA (2018) Bioanalytical method validation guidance. Food and Drug Administration 1043:25
Fekete S, Kohler I, Rudaz S, Guillarme D (2014) Importance of instrumentation for fast liquid chromatography in pharmaceutical analysis. J Pharm Biomed Anal 87:105–119. https://doi.org/10.1016/j.jpba.2013.03.012
Gaikwad PV, Sawant SD, Ghante MR, Munot NM (2010) Ultra performance liquid chromatography : a recent novel development in HPLC. Pharm Glob (IJCP) 01:1–3
Goleniowski ME, Bongiovanni GA, Palacio L, Nuñez CO, Cantero JJ (2006) Medicinal plants from the “Sierra de Comechingones”, Argentina. J Ethnopharmacol 107:324–341. https://doi.org/10.1016/j.jep.2006.07.026
Heyden YV, Nijhuis A, Smeyers-Verbeke J, Vandeginste BGM, Massart DL (2001) Guidance for robustness/ruggedness tests in method validation. J Pharm Biomed Anal 24:723–753. https://doi.org/10.1016/S0731-7085(00)00529-X
Högner C, Sturm S, Seger C, Stuppner H (2013) Development and validation of a rapid ultra-high performance liquid chromatography diode array detector method for Vitex agnus-castus. J Chromatogr B 927:181–190. https://doi.org/10.1016/j.jchromb.2013.02.037
ICH (2005) Technical requirements for the registration of pharmaceutical for human use, Validation of analytical procedures: text and methodology Q2(R1), International Conference on Harmonization p. 1–13
Li X, Wang Y, Sun Q, Xu B, Yu Y, Wang X (2016) Molecularly imprinted solid phase extraction in a syringe filter for determination of triazine herbicides in Radix Paeoniae Alba by ultra-fast liquid chromatography. Talanta 148:539–547. https://doi.org/10.1016/j.talanta.2015.11.027
Medeiros-Neves B, Corrêa De Barros FM, Von Poser GL, Teixeira HF (2015) Quantification of coumarins in aqueous extract of Pterocaulon balansae (Asteraceae) and characterization of a new compound. Molecules 20:18083–18094. https://doi.org/10.3390/molecules201018083
Medeiros-Neves B, Teixeira HF, von Poser GL (2018) The genus Pterocaulon (Asteraceae): a review on traditional medicinal uses, chemical constituents and biological properties. J Ethnopharmacol 224:451–464. https://doi.org/10.1016/j.jep.2018.06.012
Meira A d S, Battistel AP, Teixeira HF, Volpato NM (2020) Evaluation of porcine skin layers separation methods, freezing storage and anatomical site in in vitro percutaneous absorption studies using penciclovir formulations. J Drug Deliv Sci Technol 60:101926. https://doi.org/10.1016/j.jddst.2020.101926
Nemitz MC, Yatsu FKJ, Bidone J, Koester LS, Bassani VL, Garcia CV, Mendez ASL, von Poser GL, Teixeira HF (2015) A versatile, stability-indicating and high-throughput ultra-fast liquid chromatography method for the determination of isoflavone aglycones in soybeans, topical formulations, and permeation assays. Talanta 134:183–193. https://doi.org/10.1016/j.talanta.2014.10.062
Panatieri LF, Brazil NT, Faber K, Medeiros-Neves B, von Poser GL, Rott MB, Zorzi GK, Teixeira HF (2017) Nanoemulsions containing a coumarin-rich extract from Pterocaulon balansae (Asteraceae) for the treatment of ocular Acanthamoeba keratitis. AAPS PharmSciTech 18:721–728. https://doi.org/10.1208/s12249-016-0550-y
Riveiro ME, Shayo C, Monczor F, Fernández N, Baldi A, De Kimpe N, Rossi J, Debenedetti S, Davio C (2004) Induction of cell differentiation in human leukemia U-937 cells by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon polystachyum. Cancer Lett 210:179–188. https://doi.org/10.1016/j.canlet.2004.03.015
Silva CL, Pereira J, Wouter VG, Giró C, Câmara JS (2011) A fast method using a new hydrophilic-lipophilic balanced sorbent in combination with ultra-high performance liquid chromatography for quantification of significant bioactive metabolites in wines. Talanta 86:82–90. https://doi.org/10.1016/j.talanta.2011.08.007
Stein AC, Sortino M, Avancini C, Zacchino S, von Poser G (2005) Ethnoveterinary medicine in the search for antimicrobial agents: antifungal activity of some species of Pterocaulon (Asteraceae). J Ethnopharmacol 99:211–214. https://doi.org/10.1016/j.jep.2005.02.011
Stein AC, Álvarez S, Avancini C, Zacchino S, von Poser G (2006) Antifungal activity of some coumarins obtained from species of Pterocaulon (Asteraceae). J Ethnopharmacol 107:95–98. https://doi.org/10.1016/j.jep.2006.02.009
Stopiglia CDO, da Rocha VD, de Carvalho Meirelles G, Teixeira H, von Poser GL, Scroferneker ML (2011) Antifungal activity of Pterocaulon species (Asteraceae) against Sporothrix schenckii. J Mycol Med 21:169–172. https://doi.org/10.1016/j.mycmed.2011.07.002
Torres FC, Medeiros-Neves B, Ferreira Teixeira H, Kawanoa D, Eifler-Lima VL, Cassel E, Vargas, RMF, von Poser GL (2017) Supercritical CO2 extraction as a selective method for the obtainment of coumarins from Pterocaulon balansae (Asteraceae). J CO2 Util 18:303–308. https://doi.org/10.1016/j.jcou.2017.02.008
Vera N, Popich S, Luna L, Cravero R, Sierra MG, Bardón A (2006) Toxicity and synergism in the feeding deterrence of some coumarins on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae). Chem Biodivers 3:21–26. https://doi.org/10.1002/cbdv.200690002
Vianna DR, Hamerski L, Figueiró F, Bernardi A, Visentin LC, Pires ENS, Teixeira HF, Salbego CG, Eifler-Lima VL, Battastini AMO, von Poser GL, Pinto AC (2012) Selective cytotoxicity and apoptosis induction in glioma cell lines by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon species. Eur J Med Chem 57:268–274. https://doi.org/10.1016/j.ejmech.2012.09.007
Acknowledgments
BMN would like to thank the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES, Brazil) for a scholarship (finance code 001). HT and GVP are recipients of research fellowship from The Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq).
Funding
Financial support was received from the Brazilian agencies Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (FAPERGS).
Author information
Authors and Affiliations
Contributions
BMN contributed to plant collection and identification, confection of herbarium, running the laboratory work, analysis of the data, and drafting the paper. MCN and NTB contributed to the laboratory work and analysis of the data. RSS and MS contributed to critical reading of the manuscript. HT and GVP designed the study, supervised the laboratory work, and contributed to critical reading of the manuscript. All authors have read the final manuscript and approved the submission.
Corresponding author
Ethics declarations
Conflict of Interest
The authors declare that they have no conflict of interest.
Supplementary Information
ESM 1
(PDF 135 kb).
Rights and permissions
About this article
Cite this article
Medeiros-Neves, B., Nemitz, M.C., Brazil, N.T. et al. Determination of Coumarins from Pterocaulon balansae by an Ultra-Fast Liquid Chromatography Method in Topical Applications. Rev. Bras. Farmacogn. 30, 765–773 (2020). https://doi.org/10.1007/s43450-020-00115-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s43450-020-00115-4