Synthesis and in vitro cytotoxicity of novel ursolic acid derivatives
- PMID: 20657424
- PMCID: PMC6264753
- DOI: 10.3390/molecules15064033
Synthesis and in vitro cytotoxicity of novel ursolic acid derivatives
Abstract
In an effort to improve potential hepatoprotective and anti-tumor activities, eight novel ursolic acid (UA) derivatives were designed and synthesized with substitution at positions of C-3, C-11 and C-28 of UA. Their structures were confirmed using IR, MS and (1)H-NMR and elemental analysis. Their in vitro cytotoxicity against various cancer cell lines (HeLa, SKOV3 and BGC-823) was evaluated by the standard MTT assay. Among them, compound 13 exhibited more potent cytotoxicity than ursolic acid.
Figures
Similar articles
-
Evolution in medicinal chemistry of ursolic acid derivatives as anticancer agents.Eur J Med Chem. 2015 Mar 6;92:648-55. doi: 10.1016/j.ejmech.2015.01.031. Epub 2015 Jan 16. Eur J Med Chem. 2015. PMID: 25617694 Free PMC article. Review.
-
Synthesis and antitumor activity evaluation of novel ursolic acid derivatives.J Asian Nat Prod Res. 2016;18(3):280-8. doi: 10.1080/10286020.2015.1070830. Epub 2015 Nov 3. J Asian Nat Prod Res. 2016. PMID: 26524942
-
[Synthesis and anti-tumor activity of ursolic acid derivatives].Yao Xue Xue Bao. 2011 May;46(5):556-60. Yao Xue Xue Bao. 2011. PMID: 21800543 Chinese.
-
Synthesis and Biological Evaluation of Novel Ursolic acid Derivatives as Potential Anticancer Prodrugs.Chem Biol Drug Des. 2015 Dec;86(6):1397-404. doi: 10.1111/cbdd.12608. Epub 2015 Jul 14. Chem Biol Drug Des. 2015. PMID: 26077799
-
Ursolic acid derivatives for pharmaceutical use: a patent review (2012-2016).Expert Opin Ther Pat. 2017 Sep;27(9):1061-1072. doi: 10.1080/13543776.2017.1344219. Epub 2017 Jun 30. Expert Opin Ther Pat. 2017. PMID: 28637397 Review.
Cited by
-
Ursolic Acid Analogs as Potential Therapeutics for Cancer.Molecules. 2022 Dec 16;27(24):8981. doi: 10.3390/molecules27248981. Molecules. 2022. PMID: 36558113 Free PMC article. Review.
-
Anti-cancer natural products isolated from chinese medicinal herbs.Chin Med. 2011 Jul 22;6(1):27. doi: 10.1186/1749-8546-6-27. Chin Med. 2011. PMID: 21777476 Free PMC article.
-
Self-assembled micelles composed of doxorubicin conjugated Y-shaped PEG-poly(glutamic acid)2 copolymers via hydrazone linkers.Molecules. 2014 Aug 11;19(8):11915-32. doi: 10.3390/molecules190811915. Molecules. 2014. PMID: 25116804 Free PMC article.
-
Beneficial Effects of Ursolic Acid and Its Derivatives-Focus on Potential Biochemical Mechanisms in Cardiovascular Conditions.Nutrients. 2021 Oct 30;13(11):3900. doi: 10.3390/nu13113900. Nutrients. 2021. PMID: 34836155 Free PMC article. Review.
-
Evolution in medicinal chemistry of ursolic acid derivatives as anticancer agents.Eur J Med Chem. 2015 Mar 6;92:648-55. doi: 10.1016/j.ejmech.2015.01.031. Epub 2015 Jan 16. Eur J Med Chem. 2015. PMID: 25617694 Free PMC article. Review.
References
-
- Li K.-Q., Chen W., Xiong X.-J. Chemistry, pharmacology and clinical application of Ursolic Acid. J. Chinese Med. 2002;24:709–711.
-
- Muto Y., Ninomiya M., Fujiki H.J. Present Status of Research on Cancer Chemoprevention in Japan. Jpn. J. Clin. Oncol. 1990;20:219–224. - PubMed
-
- Honda T., Finlay H.J., Gribble G.W. New enone derivatives of oleanolic acid and ursolic acid as inhibitors of nitric oxide production in mouse macrophages. Bioorg. Med. Chem. Lett. 1997;7:1623–1628. doi: 10.1016/S0960-894X(97)00279-5. - DOI
-
- Honda T., Rounds B.V., Gribble G.W., Suh N., Wang Y., Sporn M.B. Design and synthesis of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, a novel and highly active inhibitor of nitric oxide production in mouse macrophages. Bioorg. Med. Chem. Lett. 1998;8:2711–2714. doi: 10.1016/S0960-894X(98)00479-X. - DOI - PubMed
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
Miscellaneous