Betulinic acid

• Mairin
• 3α -hydroxymethyl- 1- isopropenyl - 5α, 5β, 8,8,11 α - pentamethyl- icosahydro -cyclopenta [ a] chrysene -9- acid

Colorless crystals

Fixed

276 ° C

Template: Infobox chemical / molecular formula search available

Betulinic acid is a pentacyclic triterpene carboxylic acid, which is mainly found as secondary plant compound ( phytoalexin ) in the bark of many different plant species.

Occurrence and production

Betulinic acid found in many plant species, especially the bark of trees from the families of plane trees plants, the Birch family and Ebony plants, eg with about 2.5 percent in bark of plane trees ( Platanus acerifolia ) and a small percentage in the dried beef juice of birch ( Betula Latin, hence the name). It can be both produced by oxidation of betulin from the other by extraction and repeated crystallization from plane bark. Particular advantages of the recovery from plane are missing contamination with other terpenes and a relatively small amount of energy. In the production process the Biosolutions Halle has a patent. The patent of the extraction process has now been bought by the pharmaceutical company Boehringer Ingelheim.

Use

Betulinic acid acts in a laboratory experiment inhibitory against melanoma cells ( by initiating the cell death program ), and HIV viruses ( by inhibiting the reverse transcriptase). It forms the starting material for advanced AIDS drugs as bevirimat (PA -457 ), which is clinically tested. The effectiveness of betulinic acid against dermatophytes and plasmodia indicated on the original benefits of the substance against fungal and Plasmodienbefall the plant. For medical use against malaria, the dosage required and their side effects are too high.