Oleanolic acid

• (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-4a-carbonsäure (IUPAC)

Crystalline solid

306-308 ° C

Insoluble in water, soluble in methanol

Attention

> 2000 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Oleanolic acid is a pentacyclic triterpene, which is composed of five cyclohexane. The saponin of oleanolic acid is a natural component of a number of plants.

Occurrence

Oleanolic acid is contained as a natural product in a variety of plants. For example, they may consist of sage (Salvia officinalis), vulgar ivy (Hedera helix), sugar beet (Beta vulgaris), ginseng (Panax ginseng), plantain ( Plantago major), Syzygium cumini, pistachios ( Pistazia vera), olive leaves ( Olea europaea) and Weißbeerigen mistletoe (Viscum album ) are obtained.

Pharmacological properties

Oleanolic acid is weak cytotoxic and has only a low anti- oxidative potential. Since the pharmacologically interesting properties are relatively weak, various derivatives of oleanolic acid were prepared which have a much higher potency. A derivative having a much higher potential Bardoxolon (2- cyano-3 ,12- dioxo- l ,9-dien -28- oleanolic acid, CDDO ), or its methyl ester ( methyl - Bardoxolon ). Bardoxolon is a promising chemopreventive and cytostatic substance, which has an anti -proliferative and pro- apoptotic. The compound is currently in clinical trials ( Phase I / II). For the treatment of chronic renal failure Bardoxolon -methyl is in phase III clinical trials.

Since 1977, oleanolic acid in China and Japan is used in liver disease as an oral therapeutic. Since for hyperlipidemia and nichtlymphatische leukemia in 1986. In Japan, a oleanolhaltige cream to protect against skin cancer in the trade since 1990.