Prunol, Malol, beta-Ursolic acid, NSC4060, CCRIS 7123, TOS-BB-0966, 3-beta-hydroxyurs-12-en-28-oic acid
|Molar mass||456.70 g·mol−1|
|Melting point||285 to 288 °C (545 to 550 °F; 558 to 561 K)|
|Boiling point||556.89 °C (1,034.40 °F; 830.04 K)|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
Ursolic acid (sometimes referred to as urson, prunol, malol, or 3-beta-3-hydroxy-urs-12-ene-28-oic-acid), is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme. It has been used in cosmetics and is also capable of inhibiting various cancer cell types by inhibiting the STAT3 activation pathway, and may also decrease proliferation of cancer cells and induce apoptosis. Ursolic acid has also been shown to inhibit JNK expression and IL-2 activation of JURKAT leukemic T Cells leading to the reduction in proliferation and T cell activation.
Ursolic acid can serve as a starting material for synthesis of more potent bioactive derivatives, such as antitumor agents. It has been found to reduce muscle atrophy and to stimulate muscular growth in mice, also showing a potential for therapeutic use as a cardioprotective compound.
Ursolic acid was found to be a weak aromatase inhibitor (IC50 = 32 μM) and has been shown to increase the amount of muscle and brown fat and decrease white fat obesity and associated conditions when added to diets fed to mice. Under physiological concentrations, ursolic acid also induces eryptosis (the apoptosis-like suicidal cell death in defective red blood cells).
Ursolic acid is present in many plants, such as Mirabilis jalapa, as well as in many frutis and herbs used in daily life (e.g. apples, basil, bilberries, cranberries, elder flower, peppermint, rosemary, lavender, oregano, thyme, hawthorn, and prunes). Apple peels contain large quantities of ursolic acid and related compounds.
- PubChem 64945
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- PMID 21923134
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