Oleanolic acid

Pentacyclic triterpene (triterpensapogenin) with a carboxyl group, which is almost insoluble in water but highly soluble in methanol.

Oleanolic acid is contained as a natural substance in a variety of plants so in: sage (Salvia officinalis), taiga root (Eleuterococcus erthraea), common ivy (Hedera helix), sugar beet (Beta vulgaris), ginseng (Panax ginseng), plantain (Plantago major), Syzygium cumini, pistachios (Pistazia vera), olive leaves (Olea europaea) and others.

Oleanolic acid is weakly cytotoxic, has an antioxidative, antiproliferative potential. Inhibition of TNF-alpha and IL-1beta was experimentally proven. Clinical applications prove successful in the treatment of atopic eczema. Various derivatives of oleanolic acid (e.g. bardoxolone) have a significantly stronger antiproliferative and proapoptotic effect (various derivatives are under clinical investigation).

Perorally applied oleanolic acid is used in China and Japan for liver diseases. It is also used for hyperlipidemia and non-lymphocytic leukemia.

External: Creams containing oleanolic acid are commercially available to protect against skin cancer. Experimental: Atopic eczema.

1. Bhandari P et al (2014) Oleanolic acid analogues as NO, TNF-α and IL-1β inhibitors: synthesis, biological evaluation and docking studies. Bioorg Med Chem Lett 24:4114-4119.
2. Choi JK et al (2013) Oleanolic acid acetate inhibits atopic dermatitis and allergic contact dermatitis in a murine model. ToxicolAppl Pharmacol 269:72-80.
3. George VC et al (2012) Apoptosis-induced cell death due to oleanolic acid in HaCaT keratinocyte cells--a proof-of-principle approach for chemopreventive drug development. Asian Pac J Cancer Prev 13:2015-2020.
4. Ghosh S et al (2014) Oleanolic acid isolated from ethanolic extract of Phytolacca decandra induces apoptosis in A375 skin melanoma cells: drug-DNA interaction and signaling cascade. J Integr Med 12:102-114.
5. Mabandla MV et al (2015) Early use of oleanolic acid provides protection against 6-hydroxydopamine induced dopamine neurodegeneration. Brain Res 1622:64-71.
6. Mu DW et al. (2015) Oleanolic acid suppresses the proliferation of human bladder cancer by Akt/mTOR/S6K and ERK1/2 signaling. Int J Clin Exp Pathol 8:13864-13870.
7. Rui LX et al (2016) The dual induction of apoptosis and autophagy by SZC014, a synthetic oleanolic acid derivative, in gastric cancer cells via NF-κB pathway. Tumour Biol 37:5133-5144.
8. Zhu YY et al (2015) Anticancer and apoptotic activities of oleanolic acid are mediated through cell cycle arrest and disruption of mitochondrial membrane potential in HepG2 human hepatocellular carcinoma cells. Mol Med Rep 12:5012-5018.