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Amyrin
β: (3β)-Olean-12-en-3-ol δ: (3β)-Olean-13(18)-en-3-ol β: β-Amyrenol; β-Amirin; β-Amyrine; Olean-12-en-3β-ol; 3β-Hydroxyolean-12-ene
β: 197-187.5 °C
The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton), β-amyrin (oleanane skeleton), and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C30H50O. They are widely distributed in nature and have been isolated from a variety of plant sources such as epicuticular wax. In plant biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid. All three amyrins occur in the surface wax of tomato fruit.{{cite journal |journal=European Food Research and Technology |date=2004 |volume=219 |pages=487–491 |first1=Stefan |last1=Bauer |first2=Erhard |last2=Schulte | first3=Hans-Peter |last3=Thier | title=Composition of the surface wax from tomatoes II. Quantification of the components at the ripe red stage and during ripening |doi=10.1007/s00217-004-0944-z|s2cid=90472894 }} α-Amyrin is found in dandelion coffee.
A study demonstrated that α,β-amyrin exhibits long-lasting antinociceptive and anti-inflammatory properties in 2 models of persistent nociception via activation of the cannabinoid receptors CB1 and CB2 and by inhibiting the production of cytokines and expression of NF-κB, CREB, and cyclooxygenase 2.
References
References
- ''[[Merck Index]]'', 11th Edition, '''653'''
- ''[[Merck Index]]'', 11th Edition, '''654'''
- (2007). "Production of triterpene acids by cell suspension cultures of Olea europaea". Chemical and Pharmaceutical Bulletin.
- (2006). "Dammarenediol-II synthase, the first dedicated enzyme for ginsenoside biosynthesis, in Panax ginseng". FEBS Letters.
- (2013). "Ubiquitous Ursolic Acid: A Potential Pentacyclic Triterpene Natural Product". Journal of Pharmacognosy and Phytochemistry.
- (2017). "Functional Characterization of CYP716 Family P450 Enzymes in Triterpenoid Biosynthesis in Tomato". Frontiers in Plant Science.
- (August 2011). "Activation of cannabinoid receptors by the pentacyclic triterpene α,β-amyrin inhibits inflammatory and neuropathic persistent pain in mice". Pain.
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