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Cat. No. Name Size Price Add Cart
KI3215Oleanolic acidQuoteQuote

Chemical Characteristic

Product NameOleanolic acid
CAS No.508-02-1
Molecular Weight 456.71
FormulaC30H48O3
Chemical Name3?-?hydroxy-?olean-?12-?en-?28-?oic acid
Smiles[C@@H]1(CC[C@]2(C(C1(C)C)CC[C@@]1(C)[C@]3(C)CC[C@@]4(C(=O)O)CCC(C)(C)C[C@@H]4C3=CC[C@H]21)C)O
Chemical Structure

Biological activities

Oleanolic acid is a kind of natural pentacyclic triterpenoids that is found in several plants such as Phytolacca Americana and Syzygium spp. Oleanolic acid shows anti-inflammatory, anti-hyperlipidemic, anti-diabetes, antitumor and antiviral activity, it also possesses hepatoprotective and cardioprotective properties.In anti-inflammation, in vitro tests show that oleanolic acid interacts with secretory phospholipase A2 (sPLA (2)), which is a key enzyme in inflammatory reaction. Oleanolic acid and sPLA (2) form sPLA (2)-oleanolic acid complex that irreversibly inhibits the function of sPLA (2). In LPS-induced inflammation, oleanolic acid shows anti-inflammatory activities by inhibiting hyperpermeability, the expression of cell-surface proteins, and the adhesion and migration of leukocytes. In anti-hyperlipidemia, the elevated level of blood cholesterol and lipoprotein decreases by more than 40% in hyperlipidemic rats treated with oleanolic acid in in vivo tests. In anti-diabetes, oleanolic acid shows inhibition activity to protein tyrosine phosphatase 1B. In anti-tumor activity, oleanolic acid shows its cytotoxicity to target tumor cells through activation of caspases and cleavage of Poly (ADP-ribose) polymerase.[1] In anti-viral activity, oleanolic acid inhibits the HIV-1 replication in infected PBMC in vitro by inhibiting the HIV-1 protease activity. Oleanolic acid also show anti-HCV activity by suppressing HCV NS5B RdRp activity.[2] In hepatoprotection, oleanolic acid protect against the hepatotoxicity produced by several chemicals. The hepatoprotective activity of oleanolic acid attributes to suppression of hepatic cytochrome P-450 enzymes.[3] In cardioprotection, oleanolic acid induces prostaglandin I2, which is an effective vasodilator by upregulation of Cox-2 in in vitro tests.

Protocols

Oleanolic acid is dissolved in 2%w/v dimethyl sulfoxide (DMSO) and then diluted with PBS for each experiment (the ?nal concentration of DMSO is 0.2%,w/v) in vitro.

References

[1] Pengxia ZHANG, Hongmei LI, Dong CHEN, Juhua NI, Yuming KANG, and Shuqiu WANG. Oleanolic Acid Induces Apoptosis in Human Leukemia Cells through Caspase Activation and Poly (ADP-ribose) Polymerase Cleavage. Acta Biochim Biophys Sin 2007, 39: 803 -809.
[2] Kong L, Li S, Liao Q, Zhang Y, Sun R, Zhu X, Zhang Q, Wang J, Wu X, Fang X, Zhu Y. Oleanolic acid and ursolic acid: novel hepatitis C virus antivirals that inhibit NS5B activity. Antiviral Res. 2013,98(1): 44-53.
[3] Jie Liu. Pharmacology of oleanolic acid and ursolic acid. Journal of Ethnopharmacology. 1995, 49: 57-68
[4] Martín R, Carvalho-Tavares J, Hernández M, Arnés M, Ruiz-Gutiérrez V, Nieto ML. Beneficial actions of oleanolic acid in an experimental model of multiple sclerosis: a potential therapeutic role. Biochem Pharmacol. 2010,79(2):198- 208.

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