Study of Pentacyclic Triterpenes from Lyophilised Aguaje: Anti-Inflammatory and Antioxidant Properties

Overview

Journal Int J Mol Sci

Publisher MDPI

Specialties Biochemistry
Chemistry
Molecular Biology

Date 2024 Sep 14

PMID 39273562

Authors

Luis Apaza Ticona

Javier Sanchez Sanchez-Corral

Natalia Montoto Lozano

Pablo Prieto Ramos

Angel Rumbero Sanchez

Affiliations

Soon will be listed here.

Abstract

, commonly known as Aguaje or Moriche palm, is traditionally recognised in South America for its medicinal properties, particularly for its anti-inflammatory and antioxidant effects. However, the bioactive compounds responsible for these effects have not been thoroughly investigated. This study aims to isolate and characterise pentacyclic triterpenoid compounds from and to evaluate their therapeutic potential. Using various chromatographic and spectroscopic techniques including Nuclear Magnetic Resonance (NMR) and Mass Spectrometry (MS), three pentacyclic triterpenoid compounds were successfully isolated. Among them, compound (3,11-dioxours-12-en-28-oic acid) exhibited notable bioactivity, significantly inhibiting the activation of Nuclear Factor kappa-light-chain-enhancer of activated B cells (NF-κB) (IC = 7.39-8.11 μM) and of Nitric Oxide (NO) (IC = 4.75-6.59 μM), both of which are key processes in inflammation. Additionally, compound demonstrated potent antioxidant properties by activating the antioxidant enzyme Superoxide Dismutase (SOD) (EC = 1.87 μM) and the transcription factor Nuclear factor erythroid 2-related factor 2 (Nrf2) (EC = 243-547.59 nM), thus showing its potential in combating oxidative stress. This study is the first to isolate and characterise the three compounds from , suggesting that compound could be a promising candidate for the development of safer and more effective therapies for inflammatory and oxidative stress-related diseases.

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References

Benitez Mora M, Kosior M, Damiano S, Longobardi V, Presicce G, Di Vuolo G . Dietary supplementation with green tea extract improves the antioxidant status and oocyte developmental competence in Italian Mediterranean buffaloes. Theriogenology. 2023; 215:50-57. DOI: 10.1016/j.theriogenology.2023.11.022. View

Baer-Dubowska W, Narozna M, Krajka-Kuzniak V . Anti-Cancer Potential of Synthetic Oleanolic Acid Derivatives and Their Conjugates with NSAIDs. Molecules. 2021; 26(16). PMC: 8398353. DOI: 10.3390/molecules26164957. View

Patil K, Mohapatra P, Patel H, Goyal S, Ojha S, Kundu C . Pentacyclic Triterpenoids Inhibit IKKβ Mediated Activation of NF-κB Pathway: In Silico and In Vitro Evidences. PLoS One. 2015; 10(5):e0125709. PMC: 4418667. DOI: 10.1371/journal.pone.0125709. View

Apaza Ticona L, Rumbero Sanchez A, Sanchez Sanchez-Corral J, Iglesias Moreno P, Ortega Domenech M . Anti-inflammatory, pro-proliferative and antimicrobial potential of the compounds isolated from Daemonorops draco (Willd.) Blume. J Ethnopharmacol. 2020; 268:113668. DOI: 10.1016/j.jep.2020.113668. View

Saha S, Buttari B, Panieri E, Profumo E, Saso L . An Overview of Nrf2 Signaling Pathway and Its Role in Inflammation. Molecules. 2020; 25(22). PMC: 7700122. DOI: 10.3390/molecules25225474. View

Kamble S, Patel H, Goyal S, Noolvi M, Mahajan U, Ojha S . In silico Evidence for Binding of Pentacyclic Triterpenoids to Keap1-Nrf2 Protein-Protein Binding Site. Comb Chem High Throughput Screen. 2016; 20(3):215-234. DOI: 10.2174/1386207319666161214111822. View

Minhas R, Bansal Y, Bansal G . Inducible nitric oxide synthase inhibitors: A comprehensive update. Med Res Rev. 2019; 40(3):823-855. DOI: 10.1002/med.21636. View

Zhang D, Lo S, Sun Z, Habib G, Lieberman M, Hannink M . Ubiquitination of Keap1, a BTB-Kelch substrate adaptor protein for Cul3, targets Keap1 for degradation by a proteasome-independent pathway. J Biol Chem. 2005; 280(34):30091-9. DOI: 10.1074/jbc.M501279200. View

Barboza N, Cruz J, Correa R, Lamarao C, Lima A, Inada N . Buriti (Mauritia flexuosa L. f.): An Amazonian fruit with potential health benefits. Food Res Int. 2022; 159:111654. DOI: 10.1016/j.foodres.2022.111654. View

10.

Roberti A, Chaffey L, Greaves D . NF-κB Signaling and Inflammation-Drug Repurposing to Treat Inflammatory Disorders?. Biology (Basel). 2022; 11(3). PMC: 8945680. DOI: 10.3390/biology11030372. View

11.

Na H, Surh Y . Modulation of Nrf2-mediated antioxidant and detoxifying enzyme induction by the green tea polyphenol EGCG. Food Chem Toxicol. 2007; 46(4):1271-8. DOI: 10.1016/j.fct.2007.10.006. View

12.

Cinelli M, Do H, Miley G, Silverman R . Inducible nitric oxide synthase: Regulation, structure, and inhibition. Med Res Rev. 2019; 40(1):158-189. PMC: 6908786. DOI: 10.1002/med.21599. View

13.

Chun J, Lee C, Hwang S, Im J, Kim J . Ursolic acid inhibits nuclear factor-κB signaling in intestinal epithelial cells and macrophages, and attenuates experimental colitis in mice. Life Sci. 2014; 110(1):23-34. DOI: 10.1016/j.lfs.2014.06.018. View

14.

Leal A, Wang R, Salvador J, Jing Y . Synthesis of novel ursolic acid heterocyclic derivatives with improved abilities of antiproliferation and induction of p53, p21waf1 and NOXA in pancreatic cancer cells. Bioorg Med Chem. 2012; 20(19):5774-86. DOI: 10.1016/j.bmc.2012.08.010. View

15.

Perez M, Fourcade L, Mateescu M, Paquin J . Neutral Red versus MTT assay of cell viability in the presence of copper compounds. Anal Biochem. 2017; 535:43-46. DOI: 10.1016/j.ab.2017.07.027. View

16.

Houghton C, Fassett R, Coombes J . Sulforaphane and Other Nutrigenomic Nrf2 Activators: Can the Clinician's Expectation Be Matched by the Reality?. Oxid Med Cell Longev. 2016; 2016:7857186. PMC: 4736808. DOI: 10.1155/2016/7857186. View

17.

Suh N, Honda T, Finlay H, Barchowsky A, Williams C, Benoit N . Novel triterpenoids suppress inducible nitric oxide synthase (iNOS) and inducible cyclooxygenase (COX-2) in mouse macrophages. Cancer Res. 1998; 58(4):717-23. View

18.

Harun N, Septama A, Ahmad W, Suppian R . Immunomodulatory effects and structure-activity relationship of botanical pentacyclic triterpenes: A review. Chin Herb Med. 2022; 12(2):118-124. PMC: 9476727. DOI: 10.1016/j.chmed.2019.11.007. View

19.

Chen H, Gao Y, Wang A, Zhou X, Zheng Y, Zhou J . Evolution in medicinal chemistry of ursolic acid derivatives as anticancer agents. Eur J Med Chem. 2015; 92:648-55. PMC: 4336574. DOI: 10.1016/j.ejmech.2015.01.031. View

20.

Ozenver N, Efferth T . Small molecule inhibitors and stimulators of inducible nitric oxide synthase in cancer cells from natural origin (phytochemicals, marine compounds, antibiotics). Biochem Pharmacol. 2020; 176:113792. DOI: 10.1016/j.bcp.2020.113792. View