Beta amyrin
Compound Structure: |
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Synonyms: | beta-Amyrin;559-70-6;Amyrin;beta-Amyrenol;Olean-12-en-3beta-ol;UNII-KM8353IPSO;3beta-hydroxyolean-12-ene;KM8353IPSO;CHEBI:10352;AMYRIN, BETA-;EINECS 209-204-6 | ||||||||||||||||||||||||||||||||||||||
Compound ID: | NMPC-652 | ||||||||||||||||||||||||||||||||||||||
PubChem ID: | |||||||||||||||||||||||||||||||||||||||
Molecular Formula: | C30H50O | ||||||||||||||||||||||||||||||||||||||
Canonical SMILES: | CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)C)C | ||||||||||||||||||||||||||||||||||||||
InChIKey: | JFSHUTJDVKUMTJ-QHPUVITPSA-N | ||||||||||||||||||||||||||||||||||||||
About the compound: | Beta-amyrin is a naturally occurring pentacyclic triterpenoid, characterized by its oleanane structure with a specific hydroxy group substitution at the 3beta-position and a double bond between positions 12 and 13. It is widely recognized as one of the most common triterpenoids found in higher plants. Functionally, beta-amyrin serves as a plant metabolite and also as a metabolite in the fungus Aspergillus. It belongs to the class of secondary alcohols and is derived from a hydride of an oleanane. The amyrins, as a group, consist of three closely related natural chemical compounds belonging to the triterpene class. These are alpha-amyrin, which has an ursane skeleton, beta-amyrin with an oleanane skeleton, and delta-amyrin. Each of these compounds is a pentacyclic triterpenol with the chemical formula C30H50O. They are ubiquitously distributed in nature and have been isolated from a wide array of plant sources, often found in epicuticular wax. In terms of plant biosynthesis, alpha-amyrin is a precursor to ursolic acid, while beta-amyrin leads to the formation of oleanolic acid. Notably, all three amyrins are present in the surface wax of tomato fruits, and alpha-amyrin is found in dandelion coffee. From a pharmacological perspective, a study has highlighted that the combination of alpha and beta-amyrin exhibits potent and long-lasting antinociceptive (pain-relieving) and anti-inflammatory effects. These effects were observed in models of persistent nociception and are attributed to the activation of cannabinoid receptors CB1 and CB2. Additionally, the study suggested that these compounds work by inhibiting the production of cytokines and the expression of NF-κB, CREB, and cyclooxygenase 2, which are key players in inflammatory responses. This discovery underlines the potential therapeutic applications of amyrins in treating pain and inflammation. GHS Hazard Statements H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
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Properties: |
Chemical and Physical Properties
Source: PubChem |
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Source Species: |
Borreria verticillata. Chrysophyllum albidum Ehretia cymosa Euphorbia hirta Phaseolus vulgaris Maesobotrya barteri |