Ursolic acid

• Urson
• Prunol
• Malol
• (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-Hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picen-4a-carbonsäure (IUPAC)

Colorless crystalline needles

Fixed

~ 278 ° C

Insoluble in water

Template: Infobox chemical / molecular formula search available

The ursolic acid, which is also known under other common names Urson, Prunol or Malol, belongs to the class of triterpenoids.

Occurrence

Ursolic acid comes as a natural substance, among other things in apples (Malus ), summer savory ( Satureja hortensis ), thyme (Thymus vulgaris ), True guava ( Psidium guajava ), basil ( genus ) ( Ocimum ), True Catnip ( Nepeta cataria ), Small Braunelle ( Prunella vulgaris), holly (Ilex ), and rose family ( Rosaceae ) ago. This list emphasizes the prevalence of this natural substance and is far from complete.

Features and Construction

Ursolic acid is a pentacyclic triterpenoid having the common characteristic among the sapogenins Picenstruktur. It is structurally related to the alpha -and beta- amyrin and oleanolic the.

1H - and 13C -NMR spectra are described in the literature.

Use

Ursolic acid is used as auxiliaries in the food industry and in the production of cosmetics.

Biological Significance

The pharmacological properties of ursolic acid are detected long and continue to find interest in the research community. Great interest is their effect as inhibitors of cyclooxygenase and their cytotoxicity and thus possibly their specific use as anti-inflammatory drugs and cancer agent.

In the model organism Farbmaus ursolic acid causes a reduced muscle atrophy ( muscle wasting). The connection engages in the signaling cascade of insulin/IGF-1 and reduces the expression of atrophieassoziierter mRNA in skeletal muscle. In addition, a reduction of glucose, cholesterol and triglyceride levels could be measured in the blood in the test animals.