Development and Evaluation of Oleanolic Acid Dosage Forms and Its Derivatives

Overview

Journal Biomed Res Int

Publisher Wiley

Specialties Biomedical Engineering
Biotechnology
General Medicine

Date 2020 Dec 10

PMID 33299854

Citations 15

Authors

Anjie Feng

Shanjing Yang

Yue Sun

Li Zhang

Fumin Bo

Lingjun Li

Affiliations

Soon will be listed here.

Abstract

Oleanolic acid is a pentacyclic triterpenoid compound that exists widely in medicinal herbs and other plants. Because of the extensive pharmacological activity, oleanolic acid has attracted more and more attention. However, the structural characteristics of oleanolic acid prevent it from being directly made into new drugs, which limits the application of oleanolic acid. Through the application of modern preparation techniques and methods, different oleanolic acid dosage forms and derivatives have been designed and synthesized. These techniques can improve the water solubility and bioavailability of oleanolic acid and lay a foundation for the new drug development. In this review, the recent progress in understanding the oleanolic acid dosage forms and its derivatives are discussed. Furthermore, these products were evaluated comprehensively from the perspective of characterization and pharmacokinetics, and this work may provide ideas and references for the development of oleanolic acid preparations.

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References

Jeong D, Kim Y, Kim H, Ji H, Yoo S, Choi W . Dose-linear pharmacokinetics of oleanolic acid after intravenous and oral administration in rats. Biopharm Drug Dispos. 2006; 28(2):51-7. DOI: 10.1002/bdd.530. View

de Melo C, Queiroz M, Fonseca S, Bizerra A, Lemos T, Melo T . Oleanolic acid, a natural triterpenoid improves blood glucose tolerance in normal mice and ameliorates visceral obesity in mice fed a high-fat diet. Chem Biol Interact. 2010; 185(1):59-65. DOI: 10.1016/j.cbi.2010.02.028. View

Yu Z, Sun W, Peng W, Yu R, Li G, Jiang T . Pharmacokinetics in Vitro and in Vivo of Two Novel Prodrugs of Oleanolic Acid in Rats and Its Hepatoprotective Effects against Liver Injury Induced by CCl4. Mol Pharm. 2016; 13(5):1699-710. DOI: 10.1021/acs.molpharmaceut.6b00129. View

Laszczyk M . Pentacyclic triterpenes of the lupane, oleanane and ursane group as tools in cancer therapy. Planta Med. 2009; 75(15):1549-60. DOI: 10.1055/s-0029-1186102. View

Alvarado H, Abrego G, Garduno-Ramirez M, Clares B, Calpena A, Garcia M . Design and optimization of oleanolic/ursolic acid-loaded nanoplatforms for ocular anti-inflammatory applications. Nanomedicine. 2015; 11(3):521-30. DOI: 10.1016/j.nano.2015.01.004. View

Peng F, Li G, Xie Y, Yin H, Li X, Yang Y . Compositional characterization of Pyrus ussuriensis Maxim and their antioxidant activities and induction of apoptosis in Bel-7402 cell. J Food Biochem. 2020; 44(6):e13222. DOI: 10.1111/jfbc.13222. View

Jeong H . Inhibition of cytochrome P450 2E1 expression by oleanolic acid: hepatoprotective effects against carbon tetrachloride-induced hepatic injury. Toxicol Lett. 1999; 105(3):215-22. DOI: 10.1016/s0378-4274(99)00004-1. View

Su Y, Meng L, Sun J, Li W, Shao L, Chen K . Design, synthesis of oleanolic acid-saccharide conjugates using click chemistry methodology and study of their anti-influenza activity. Eur J Med Chem. 2019; 182:111622. DOI: 10.1016/j.ejmech.2019.111622. View

Chen F, Wang J, Zhang L, Xing S, Wang Y, Wang K . Oleanolic acid derivative DKS26 exerts antidiabetic and hepatoprotective effects in diabetic mice and promotes glucagon-like peptide-1 secretion and expression in intestinal cells. Br J Pharmacol. 2017; 174(17):2912-2928. PMC: 5554319. DOI: 10.1111/bph.13921. View

10.

Li D, Cui R, Xu S, Liu Y . Synergism of cisplatin-oleanolic acid co-loaded hybrid nanoparticles on gastric carcinoma cells for enhanced apoptosis and reversed multidrug resistance. Drug Deliv. 2020; 27(1):191-199. PMC: 7006694. DOI: 10.1080/10717544.2019.1710622. View

11.

Yim T, Wu W, Pak W, Ko K . Hepatoprotective action of an oleanolic acid-enriched extract of Ligustrum lucidum fruits is mediated through an enhancement on hepatic glutathione regeneration capacity in mice. Phytother Res. 2001; 15(7):589-92. DOI: 10.1002/ptr.878. View

12.

Spivak A, Khalitova R, Nedopekina D, Dzhemileva L, Yunusbaeva M, Odinokov V . Synthesis and Evaluation of Anticancer Activities of Novel C-28 Guanidine-Functionalized Triterpene Acid Derivatives. Molecules. 2018; 23(11). PMC: 6278366. DOI: 10.3390/molecules23113000. View

13.

Phull A, Eo S, Kim S . Oleanolic acid (OA) regulates inflammation and cellular dedifferentiation of chondrocytes via MAPK signaling pathways. Cell Mol Biol (Noisy-le-grand). 2017; 63(3):12-17. DOI: 10.14715/cmb/2017.63.3.3. View

14.

Kim H, Han S, Sung H, Park S, Kang M, Han S . Blockade of visfatin induction by oleanolic acid via disturbing IL-6-TRAF6-NF-κB signaling of adipocytes. Exp Biol Med (Maywood). 2014; 239(3):284-92. DOI: 10.1177/1535370213514511. View

15.

Wang R, Yang W, Fan Y, Dehaen W, Li Y, Li H . Design and synthesis of the novel oleanolic acid-cinnamic acid ester derivatives and glycyrrhetinic acid-cinnamic acid ester derivatives with cytotoxic properties. Bioorg Chem. 2019; 88:102951. DOI: 10.1016/j.bioorg.2019.102951. View

16.

Ayeleso T, Matumba M, Mukwevho E . Oleanolic Acid and Its Derivatives: Biological Activities and Therapeutic Potential in Chronic Diseases. Molecules. 2017; 22(11). PMC: 6150249. DOI: 10.3390/molecules22111915. View

17.

Yao N, Zeng C, Zhan T, He F, Liu M, Liu F . Oleanolic Acid and Ursolic Acid Induce UGT1A1 Expression in HepG2 Cells by Activating PXR Rather Than CAR. Front Pharmacol. 2019; 10:1111. PMC: 6777376. DOI: 10.3389/fphar.2019.01111. View

18.

Man D, Casettari L, Cespi M, Bonacucina G, Palmieri G, Sze S . Oleanolic Acid Loaded PEGylated PLA and PLGA Nanoparticles with Enhanced Cytotoxic Activity against Cancer Cells. Mol Pharm. 2015; 12(6):2112-25. DOI: 10.1021/acs.molpharmaceut.5b00085. View

19.

Sommerwerk S, Heller L, Kuhfs J, Csuk R . Urea derivates of ursolic, oleanolic and maslinic acid induce apoptosis and are selective cytotoxic for several human tumor cell lines. Eur J Med Chem. 2016; 119:1-16. DOI: 10.1016/j.ejmech.2016.04.051. View

20.

Cao F, Gao Y, Wang M, Fang L, Ping Q . Propylene glycol-linked amino acid/dipeptide diester prodrugs of oleanolic acid for PepT1-mediated transport: synthesis, intestinal permeability, and pharmacokinetics. Mol Pharm. 2013; 10(4):1378-87. DOI: 10.1021/mp300647m. View