Abstract
This study reported a new application of CuFe2O4 spinel as an efficient heterogeneous catalyst for the selective oxidation of isoeugenol to licarin A under mild conditions. The CuFe2O4 was prepared via a simple method and characterized by various modern techniques such as X-ray diffraction (XRD), scanning electron microscopy (SEM) with energy dispersive X-ray analysis (EDX), and high-resolution transmission electron microscopy (HR-TEM). The XRD and HR-TEM results confirmed the structure and morphology of spinel materials, while the SEM–EDX provided valuable information on the material component. CuFe2O4 catalyst showed excellent catalytic activity in the selective oxidation of isoeugenol to give a high yield of licarin A under mild conditions. In addition, the catalyst was stable and able to reuse at least four times without the loss of catalytic activity.
Graphical Abstract
Similar content being viewed by others
Availability of data and materials
All of the material is owned by the authors and/or no permissions are required.
References
Alvarenga DJ, de Figueiredo PE, Marques MJ et al (2021) Natural and semi-synthetic licarins: neolignans with multi-functional biological properties. Rev Bras 31:257–271. https://doi.org/10.1007/S43450-021-00144-7/FIGURES/3
Bassanini I, Gavezzotti P, Monti D et al (2016) Laccase-catalyzed dimerization of glycosylated lignols. J Mol Catal B Enzym 134:295–301. https://doi.org/10.1016/J.MOLCATB.2016.10.019
Bernal FA, Gerhards M, Kaiser M et al (2020) (±)-trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents: synthesis, in vitro evaluation and SAR analysis. Eur J Med Chem 205:112493. https://doi.org/10.1016/J.EJMECH.2020.112493
Cezar Rodrigues L, Maria Barbosa-Filho J, Delany Gomes Marques S et al (2017) Formation of bioactive benzofuran via oxidative coupling, using coconut water (Cocos nucifera L.) as biocatalyst. Org Commun 10:72–78. https://doi.org/10.25135/acg.oc.10.16.11.449
Chen PY, Wu YH, Hsu MH et al (2013) Cerium ammonium nitrate-mediated the oxidative dimerization of p-alkenylphenols: a new synthesis of substituted (±)-trans-dihydrobenzofurans. Tetrahedron 69:653–657. https://doi.org/10.1016/J.TET.2012.11.006
Dias HJ, Rodrigues ML, Crotti AEM (2021) Optimization of the reaction conditions for the synthesis of dihydrobenzofuran neolignans. Article J Braz Chem Soc 32:20–28. https://doi.org/10.21577/0103-5053.20200149
El-Alfy AT, Abourashed EA, Patel C et al (2019) Phenolic compounds from nutmeg (Myristica fragrans Houtt.) inhibit the endocannabinoid-modulating enzyme fatty acid amide hydrolase. J Pharm Pharmacol 71:1879–1889. https://doi.org/10.1111/JPHP.13174
Feringa B, Wynberg H (1978) Biomimetic asymmetric oxidative coupling of phenols. Bioorg Chem 7:397–408. https://doi.org/10.1016/0045-2068(78)90031-7
Francis SK, James B, Varughese S, Nair MS (2018) Phytochemical investigation on Myristica fragrans stem bark. Nat Prod Res 33:1204–1208. https://doi.org/10.1080/14786419.2018.1457670
Gómez-Cansino R, Guzmán-Gutiérrez SL, Campos-Lara MG et al (2017) Natural compounds from Mexican medicinal plants as potential drug leads for anti-tuberculosis drugs. An Acad Bras Ciênc 89:31–43. https://doi.org/10.1590/0001-3765201720160298
Kantam ML, Yadav J, Laha S et al (2009) Asymmetric hydrosilylation of ketones catalyzed by magnetically recoverable and reusable copper ferrite nanoparticles. J Org Chem 74:4608–4611. https://doi.org/10.1021/JO9002823/SUPPL_FILE/JO9002823_SI_001.PDF
Liu SY, Wang GQ, Liang ZY, Wang QA (2013) Synthesis of dihydrobenzofuran neoligans licarin a and dihydrocarinatin as well as related triazolylglycosides. Chem Res Chin Univ 6:1119–1124. https://doi.org/10.1007/S40242-013-3131-6
Macedo AL, dos Santos TCC, Valverde AL et al (2016) An overview of neolignans of the genus Piper L.: isolation methods and biological activities. Mini-Rev Med Chem 17:693–720. https://doi.org/10.2174/1389557516666161130094826
Matsui T, Ito C, Masubuchi S, Itoigawa M (2015) Licarin A is a candidate compound for the treatment of immediate hypersensitivity via inhibition of rat mast cell line RBL-2H3 cells. J Pharm Pharmacol 67:1723–1732. https://doi.org/10.1111/JPHP.12475
Mengarda AC, Silva MP, Cirino ME et al (2021) Licarin A, a neolignan isolated from Nectandra oppositifolia Nees & Mart. (Lauraceae), exhibited moderate preclinical efficacy against Schistosoma mansoni infection. Phytother Res 35:5154–5162. https://doi.org/10.1002/PTR.7184
Morita N, Ikeda K, Chiaki H et al (2021) Gold-catalyzed formal [3+2] cycloaddition of p-quinones and 1-phenylpropenes in ionic liquid: environmentally friendly and stereoselective synthesis of 2,3-dihydrobenzofuran neolignans. Heterocycles 103:714–722. https://doi.org/10.3987/COM-20-S(K)71
Nascimento IR, Lopes LMX, Davin LB, Lewis NG (2000) Stereoselective synthesis of 8,9-licarinediols. Tetrahedron 56:9181–9193. https://doi.org/10.1016/S0040-4020(00)00873-5
Nishiyama A, Yamamura S, Terada Y, Iguchi M (1983) Anodic oxidation of some propenylphenols : synthesis of physiologically active neolignans. Chem Pharm Bull 31:2834–2844. https://doi.org/10.1248/CPB.31.2834
Pereira AC, Magalhães LG, Januário AH et al (2011) Enantiomeric resolution of (±)-licarin A by high-performance liquid-chromatography using a chiral stationary phase. J Chromatogr A 1218:7051–7054. https://doi.org/10.1016/J.CHROMA.2011.07.093
Selvan RK, Augustin CO, Berchmans LJ, Saraswathi R (2003) Combustion synthesis of CuFe2O4. Mater Res Bull 38:41–54. https://doi.org/10.1016/S0025-5408(02)01004-8
Susannah LS (2018) A Matter of Life(time) and death. ACS Catal 8(9):8597–8599. https://doi.org/10.1021/acscatal.8b03199
Tao S, Gao F, Liu X, Sørensen OT (2000) Preparation and gas-sensing properties of CuFe2O4 at reduced temperature. Mater Sci Eng B 77:172–176. https://doi.org/10.1016/S0921-5107(00)00473-6
Vasudevan S, Bhat SV (2011) Biotransformation of isoeugenol catalyzed by growing cells of Pseudomonas putida. Biocatal Biotransform 29:147–150. https://doi.org/10.3109/10242422.2011.589898
Zhu M, Meng D, Wang C, Diao G (2013) Facile fabrication of hierarchically porous CuFe2O4 nanospheres with enhanced capacitance property. ACS Appl Mater Interfaces 5:6030–6037. https://doi.org/10.1021/AM4007353
Acknowledgements
This research has been done under the research project QG.21.05, “Research on the transformation of eugenol in basil (Ocimum gratissimum L.) essential oil to bioactive compounds using heterogeneous catalysts” of Vietnam National University, Hanoi.
Funding
This research has been done under the research project QG.21.05, “Research on the transformation of eugenol in basil (Ocimum gratissimum L.) essential oil to bioactive compounds using heterogeneous catalysts” of Vietnam National University, Hanoi.
Author information
Authors and Affiliations
Contributions
DVD and TTMN desired the idea and wrote the main manuscript text; OKN and TDV performed experiments and drafted the manuscript; LVD, BTN, STL characterized physical technique and prepared figures, tables, and supporting information. All authors reviewed the manuscript.
Corresponding authors
Ethics declarations
Conflict of interest
No, I declare that the authors have no competing interests as defined by Springer, or other interests that might be perceived to influence the results and/or discussion reported in this paper.
Ethical approval
The results/data/figures in this manuscript have not been published elsewhere, nor are they under consideration (from you or one of your Contributing Authors) by another publisher. I have read the Springer journal policies on author responsibilities and submitted this manuscript in accordance with those policies.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Nguyen, O.K., Dang, L.V., Le, S.T. et al. Selective oxidation of isoeugenol to licarin A using CuFe2O4 catalysts under mild conditions. Chem. Pap. 77, 1583–1591 (2023). https://doi.org/10.1007/s11696-022-02575-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-022-02575-5