Chemical compounds from species of Croton native to South Brazil
DOI:
https://doi.org/10.22456/2527-2616.149268Keywords:
Croton, Euphorbiaceae, essential oil, hydrodistillation, supercritical CO2Abstract
Five species of Croton were investigated for the essential oil obtained by hydrodistillation from aerial parts of the plants and analyzed by gas chromatography/mass spectrometry. The essential oil yields from fresh weight ranged from 0.01% to 1%. The essential oil of C. hilarii Baill. exhibited the lowest yield (0.01%). Following this, C. pycnocephalus Müll.Arg. oil yielded 0.1%, while C. gnaphalii Baill. achieved 0.2%. Conversely, C. calycireduplicatus Allem and C. cuchillae-nigrae Croizat afforded the highest yields, both reaching 1%. The essential oils from the latter two species were rich in monoterpenes (52.5% and 59.9%, respectively), being β-pinene the prevalent compound (32.8% and 40.1%, respectively). In contrast, the essential oils from C. pycnocephalus and C. gnaphalii were characterized by a substantial content of sesquiterpenes (85.7% and 79.1%, respectively), being bicyclogermacrene (26.4% and 31%) the predominant component. The C. hilarii essential oil presented only sesquiterpene in its composition, among which sesquicineole (19.90%) and epi-α-bisabolol (16.4%) were the most abundant. The species with high amount of essential oil (C. calycireduplicatus and C. cuchillae-nigrae) were subjected to supercritical fluid extraction (SFE) at a temperature of 40 °C and different pressions. The fractions were analyzed by GC-MS. The SFE demonstrated pressure-dependent selectivity for compound classes. At 80 bar, sesquiterpenes were predominantly obtained. Increasing pressure led to the progressive disappearance of lower molecular weight terpenes and extraction of triterpenes (e.g., amyrins), and hydrocarbons at higher pressures. Nevertheless, SFE yields were generally low, indicating the conditions used were not optimal for the plants in study.
Downloads
References
Sodré R, Sales MF, Berry PE, Silva MJ. Taxonomic synopsis of Croton section Geiseleria (Euphorbiaceae) in Brazil, including description of a new species. Phytotaxa 2019; 417: 1-105. DOI: https://doi.org/10.11646/phytotaxa.417.1.1
Althobaiti AT. Taxonomic studies on family Euphorbiaceae based on some morphological, biochemical and molecular characteristics. J Adv Zool. 2023; 44: 1801-1823. DOI: https://doi.org/10.17762/jaz.v44iS6.2621
Rudall, PJ. Laticifers in Euphorbiaceae - A conspectus. Bot J Linn Soc. 1987; 94:143-163. DOI: https://doi.org/10.1111/j.1095-8339.1987.tb01043.x
Benjamaa R, Moujanni A, Kaushik N, Choi EH, Essamadi AK, Kaushik NK. Euphorbia species latex: A comprehensive review on phytochemistry and biological activities. Front Plant Sci. 2022;13:1008881. DOI: https://doi.org/10.3389/fpls.2022.1008881
Mwine JT, Van Damme P. Why do Euphorbiaceae tick as medicinal plants? A review of Euphorbiaceae family and its medicinal features. J Med Plants Res. 2011; 5:652-662.
POWO, 2025. Plants of the World Online. Facilitated by the Royal Botanic Gardens, Kew. https://powo.science.kew.org/ (accessed 26 June 2025).
Salatino A, Salatino MLF, Negri G. Traditional uses, chemistry and pharmacology of Croton species (Euphorbiaceae). J Braz Chem Soc. 2007; 1811-33. DOI: https://doi.org/10.1590/S0103-50532007000100002
Vunda SLL, Sauter IP, Cibulski SP, Roehe PM, Bordignon SAL, Rott MB, et al. Chemical composition and amoebicidal activity of Croton pallidulus, Croton ericoides and Croton isabelli (Euphorbiaceae) essential oils. Parasitol Res. 2012; 111, 961-966. DOI: https://doi.org/10.1007/s00436-012-2918-6
Palmeira Júnior SF, Conserva LM. Barbosa Filho JM. Clerodane Diterpenes from Croton Species: Distribution and a Compilation of their 13C NMR Spectral Data. Nat Prod Commun. 2019.
Moremi MP, Makolo F, Viljoen AM, Kamatou GP. A review of biological activities and phytochemistry of six ethnomedicinally important South African Croton species. J Ethnopharmacol. 2021; 280: 14416. DOI: https://doi.org/10.1016/j.jep.2021.114416
Liu C, Zhang RR, Wang YM, Zhang J, Wang Q, Cheng AW, et al. Supercritical CO2 fluid extraction of Croton crassifolius Geisel root: Chemical composition and anti-proliferative, autophagic, apoptosis-inducing, and related molecular effects on A549 tumour cells. Phytomedicine 2019; 61:152846. DOI: https://doi.org/10.1016/j.phymed.2019.152846
Niu QL, Sun H, Liu C, Li J, Liang CX, Zhang RR, et al. Croton tiglium essential oil compounds have anti-proliferative and pro-apoptotic effects in A549 lung cancer cell lines. PLoS One. 2020; 15:e0231437. DOI: https://doi.org/10.1371/journal.pone.0231437
Wang JJ, Chung HY, Zhang YB, Li GQ, Li YL, Huang WH, et al. Diterpenoids from the roots of Croton crassifolius and their anti-angiogenic activity. Phytochemistry 2016; 122:270-275. DOI: https://doi.org/10.1016/j.phytochem.2015.12.011
Bezerra FWF, Salazar MAR, Freitas LC, de Oliveira MS, dos Santos IRC, Dias MNC, et al. Chemical composition, antioxidant activity, anti-inflammatory and neuroprotective effect of Croton matourensis Aubl. leaves extracts obtained by supercritical CO2. J Supercrit Fluids 2020; 165:104992. DOI: https://doi.org/10.1016/j.supflu.2020.104992
Liu C, Zhang RR, Niu QL, Zhang J, Wang MX, Meng NN, et al. Two new diterpenoids with their antiproliferative activities from the supercritical fluid extraction of Croton crassifolius root. Nat Prod Res. 2021; 35:4479-4485. DOI: https://doi.org/10.1080/14786419.2020.1731739
Klein EJ, Santos KA, Palú F, Vieira MGA, da Silva EA. Use of supercritical CO2 and ultrasound-assisted extractions to obtain α/β-amyrin-rich extracts from uvaia leaves (Eugenia pyriformis Cambess.). J Supercrit Fluids 2018; 1-8. DOI: https://doi.org/10.1016/j.supflu.2018.02.019
Adams RP. Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy. Carol Stream (IL): Allured Publishing; 2017.
Scopel R, Góes Neto R, Falcão MA, Cassel E, Vargas RMF. Supercritical CO2 extraction of Schinus molle L. with co-solvents: mathematical modeling and antimicrobial applications. Braz Arch Biol Technol. 2013; 56:513–519. DOI: https://doi.org/10.1590/S1516-89132013000300020
Cargnin ST, Nunes JM, Haas JS, Baladão LF, Cassel E, Vargas RF, et al. Supercritical fluid extraction and high-performance liquid chromatographic determination of benzopyrans and phloroglucinol derivative in Hypericum polyanthemum. J Chromatogr B 2010; 878:83–87. DOI: https://doi.org/10.1016/j.jchromb.2009.11.012
Barros FMC, Silva FC, Nunes JM, Vargas RMF, Cassel E, von Poser GL. Supercritical extraction of phloroglucinol and benzophenone derivatives from Hypericum carinatum: Quantification and mathematical modeling. J Sep Sci. 2011; 34: 3107–3113. DOI: https://doi.org/10.1002/jssc.201100455
Klein EJ, Náthia-Neves G, Vardanega R, Meireles MAA, da Silva EA, Vieira MGA. Supercritical CO2 extraction of α-/β-amyrin from uvaia (Eugenia pyriformis Cambess.): Effects of pressure and co-solvent addition. J Supercrit Fluids 2019; 153: 104595. DOI: https://doi.org/10.1016/j.supflu.2019.104595
Downloads
Published
Versions
- 30-03-2026 (2)
- 19-12-2025 (1)
How to Cite
Issue
Section
License
Copyright (c) 2025 Drug Analytical Research
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.
The Copyright holder of manuscripts published is Drug Analytical Research. Authors who publish with this journal are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
Licensing:
Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License
Users are allowed to read, download, copy, distribute, print, search, or link to the full texts of the articles, or use them for any other lawful purpose, without asking prior permission from the publisher or the author.
