Synthesis and anticancer activity of novel oleanolic acid derivatives

Ye Ding, Zhen Zhen Zhang, Zhang Jian Huang, Yi Mou, Hui Ji, Yi Sheng Lai, Yi Hua Zhang

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Starting from oleanolic acid (OA), the target compounds (10a-10i) were synthesized via introducting α,β-unsaturated ketone moiety to OA by 7-step successive reactions including benzylation, acetylation, oxidization, bromine substitution-elimination, etc., followed by coupling of C28-carboxyl with substituted furoxans via a glycine linker. All the target compounds were identified by IR, MS and 1H NMR. MTT assay results showed that compounds 10a-10i displayed much stronger inhibitory effects than OA on the proliferation of four human tumor cell lines. The anti-proliferative activity of 10a-10e and 10i against human hepatoma HepG2 cell was comparable to that of the positive control 2-cyano-3, 12-dioxooleana-1,9(11)-dien-28-oic acid methyl ester (CDDO-Me).

Original languageEnglish (US)
Pages (from-to)385-391
Number of pages7
JournalJournal of China Pharmaceutical University
Volume42
Issue number5
StatePublished - Oct 2011
Externally publishedYes

Fingerprint

Oleanolic Acid
Bromine
Hep G2 Cells
Acetylation
Tumor Cell Line
Ketones
Glycine
Hepatocellular Carcinoma
Esters
Acids

Keywords

  • α,β-unsaturated ketone
  • Anticancer activity
  • Furoxan
  • NO donor
  • Oleanolic acid

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Pharmacology

Cite this

Ding, Y., Zhang, Z. Z., Huang, Z. J., Mou, Y., Ji, H., Lai, Y. S., & Zhang, Y. H. (2011). Synthesis and anticancer activity of novel oleanolic acid derivatives. Journal of China Pharmaceutical University, 42(5), 385-391.

Synthesis and anticancer activity of novel oleanolic acid derivatives. / Ding, Ye; Zhang, Zhen Zhen; Huang, Zhang Jian; Mou, Yi; Ji, Hui; Lai, Yi Sheng; Zhang, Yi Hua.

In: Journal of China Pharmaceutical University, Vol. 42, No. 5, 10.2011, p. 385-391.

Research output: Contribution to journalArticle

Ding, Y, Zhang, ZZ, Huang, ZJ, Mou, Y, Ji, H, Lai, YS & Zhang, YH 2011, 'Synthesis and anticancer activity of novel oleanolic acid derivatives', Journal of China Pharmaceutical University, vol. 42, no. 5, pp. 385-391.
Ding Y, Zhang ZZ, Huang ZJ, Mou Y, Ji H, Lai YS et al. Synthesis and anticancer activity of novel oleanolic acid derivatives. Journal of China Pharmaceutical University. 2011 Oct;42(5):385-391.
Ding, Ye ; Zhang, Zhen Zhen ; Huang, Zhang Jian ; Mou, Yi ; Ji, Hui ; Lai, Yi Sheng ; Zhang, Yi Hua. / Synthesis and anticancer activity of novel oleanolic acid derivatives. In: Journal of China Pharmaceutical University. 2011 ; Vol. 42, No. 5. pp. 385-391.
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