Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2024 Jun 28;29(13):3091.
doi: 10.3390/molecules29133091.

Biological Activities of Novel Oleanolic Acid Derivatives from Bioconversion and Semi-Synthesis

Nahla Triaa  1   2 , Mansour Znati  1 , Hichem Ben Jannet  1 , Jalloul Bouajila  2
Affiliations
Review

Biological Activities of Novel Oleanolic Acid Derivatives from Bioconversion and Semi-Synthesis

Nahla Triaa et al. Molecules. .

Abstract

Oleanolic acid (OA) is a vegetable chemical that is present naturally in a number of edible and medicinal botanicals. It has been extensively studied by medicinal chemists and scientific researchers due to its biological activity against a wide range of diseases. A significant number of researchers have synthesized a variety of analogues of OA by modifying its structure with the intention of creating more potent biological agents and improving its pharmaceutical properties. In recent years, chemical and enzymatic techniques have been employed extensively to investigate and modify the chemical structure of OA. This review presents recent advancements in medical chemistry for the structural modification of OA, with a special focus on the biotransformation, semi-synthesis and relationship between the modified structures and their biopharmaceutical properties.

Keywords: anticancer activity; biological activities; biotransformation; medicinal chemistry; oleanolic acid; pharmaceutical properties; triterpenoids.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structure of oleanolic acid.
Figure 2
Figure 2
OA analogues.
Scheme 1
Scheme 1
Synthesis of derivatives of methyl 3-octanoyloxyiminoolean-12-en-28-oate [92].
Scheme 2
Scheme 2
Synthesis of indole derivatives of OA [93].
Scheme 3
Scheme 3
Synthesis of Maslinic acid and 3-epi-maslinic acid [94].
Scheme 4
Scheme 4
Synthesis of new analogues of OA derivatives [95].
Scheme 5
Scheme 5
New derivatives of OA–isoxazole and OA–triazole [65,66].
Scheme 6
Scheme 6
Synthesis of OA–oxime derivatives [96].
Scheme 7
Scheme 7
Synthesis of new derivatives of OA–oxime conjugates [97].
Scheme 8
Scheme 8
Synthesis of saponin derivatives as agents with anti-inflammatory activity [98].
Scheme 9
Scheme 9
Synthesis of 11 oxo-OA derivatives as agents with anti-inflammatory activity [99].
Scheme 10
Scheme 10
Synthesis of new arylidene derivatives of OA [100].
Scheme 11
Scheme 11
Synthesis of amide analogues with a principal modification at C-28 of OA [103].
Scheme 12
Scheme 12
Synthesis of OA–phthalimidine compounds [106].
Scheme 13
Scheme 13
Synthesis of saponin analogue as anti-influenza agent [112].
Scheme 14
Scheme 14
Synthesis of novel sugar-conjugated derivatives of OA [113].
Scheme 15
Scheme 15
Synthesis of amino derivatives of OA [114].
Scheme 16
Scheme 16
Synthesis of amino derivatives as anti- influenza agents [115].
Scheme 17
Scheme 17
Synthesis of several acid derivatives with potential efficacy against influenza [116].
Scheme 18
Scheme 18
Synthesis of OA derivatives as anti-influenza agents [116].
Scheme 19
Scheme 19
Synthesis of OA derivatives as anti-hepatitis agents [119].
Scheme 20
Scheme 20
Synthesis of OA derivatives for the treatment of osteoporosis [120].
Scheme 21
Scheme 21
Synthesis of heterocyclic compounds [121].
Scheme 22
Scheme 22
Synthesis of pyrazole compounds [122].
Scheme 23
Scheme 23
Synthesis of isoxazole compounds [122].
Scheme 24
Scheme 24
OA compounds as potential osteoclastogenesis inhibitors and anti-osteoporotic agents [123].
See this image and copyright information in PMC

Similar articles

See all similar articles

References

    1. Che C.T., Zhang H. Plant Natural Products for Human Health. Int. J. Mol. Sci. 2019;20:830. doi: 10.3390/ijms20040830. - DOI - PMC - PubMed
    1. Namdeo P., Gidwani B., Tiwari S., Jain V., Joshi V., Shukla S.S., Pandey R.K., Vyas A. Therapeutic Potential and Novel Formulations of Ursolic Acid and Its Derivatives: An Updated Review. J. Sci. Food Agric. 2023;103:4275–4292. doi: 10.1002/jsfa.12423. - DOI - PubMed
    1. Yang Y., Chen K., Wang G., Liu H., Shao L., Zhou X., Liu L., Yang S. Discovery of Novel Pentacyclic Triterpene Acid Amide Derivatives as Excellent Antimicrobial Agents Dependent on Generation of Reactive Oxygen Species. Int. J. Mol. Sci. 2023;24:10566. doi: 10.3390/ijms241310566. - DOI - PMC - PubMed
    1. Sinda P.V.K., Tchuenguem R.T., Ponou B.K., Kühlborn J., Kianfé B.Y., Dzoyem J.P., Teponno R.B., Opatz T., Barboni L., Tapondjou L.A. Antimicrobial Activities of Extract, Fractions and Compounds from the Medicinal Plant Helichrysum odoratissimun (L.) Sweet (Asteraceae) S. Afr. J. Bot. 2022;147:937–941. doi: 10.1016/j.sajb.2022.03.049. - DOI
    1. Martial D.E., Dimitry M.Y., Selestin S.D., Nicolas N.Y. Hypolipidemic and Antioxidant Activity of Aqueous Extract of Clerodendrum thomsoniae Linn. (Verbenaceae) Leaves in Albino Rats, Rattus norvegicus (Muridae) J. Pharmacogn. Phytochem. 2020;9:595–602.

Grants and funding

Campus France PHC-UTIQUE PROJECT, E-mail: gestion.phcmaghreb@campusfrance.org, Tel.: +33-01-40-40-58-58.

LinkOut - more resources