Β-amyrin

Amyrin

Amyrin

Chemical compound

The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton),[3] β-amyrin (oleanane skeleton) [4] 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.[5] All three amyrins occur in the surface wax of tomato fruit.[6][7] α-Amyrin is found in dandelion coffee.[citation needed]

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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.[8]

References

  1. [1]
    Merck Index, 11th Edition, 653
  2. [2]
    Merck Index, 11th Edition, 654
  3. [3]
    Saimaru, H; Orihara, Y; Tansakul, P; Kang, YH; Shibuya, M; Ebizuka, Y (2007). "Production of triterpene acids by cell suspension cultures of Olea europaea". Chem Pharm Bull. 55 (5): 784–8. doi:10.1248/cpb.55.784. PMID 17473469.
  4. [4]
    Tansakul, P; Shibuya, M; Kushiro, T; Ebizuka, Y (2006). "Dammarenediol-II synthase, the first dedicated enzyme for ginsenoside biosynthesis, in Panax ginseng". FEBS Lett. 580 (22): 5143–9. doi:10.1016/j.febslet.2006.08.044. PMID 16962103. S2CID 20731479.
  5. [5]
    Babalola, Ibrahim T; Shode, Francis O (2013). "Ubiquitous Ursolic Acid: A Potential Pentacyclic Triterpene Natural Product" (PDF). Journal of Pharmacognosy and Phytochemistry. 2 (2): 214–222. ISSN 2278-4136. Retrieved 31 October 2022.
  6. [6]
    Yasumoto, S; Seki, H; Shimizu, Y; Fukushima, EO; Muranaka, T (2017). "Functional Characterization of CYP716 Family P450 Enzymes in Triterpenoid Biosynthesis in Tomato". Front Plant Sci. 8: 21. doi:10.3389/fpls.2017.00021. PMC 5278499. PMID 28194155.
  7. [7]
    Bauer, Stefan; Schulte, Erhard; Thier, Hans-Peter (2004). "Composition of the surface wax from tomatoes II. Quantification of the components at the ripe red stage and during ripening". European Food Research and Technology. 219: 487–491. doi:10.1007/s00217-004-0944-z. S2CID 90472894.
  8. [8]
    Simão da Silva, Kathryn A.B.; Paszcuk, Ana F.; Passos, Giselle F.; Silva, Eduardo S.; Bento, Allisson Freire; Meotti, Flavia C.; Calixto, João B. (August 2011). "Activation of cannabinoid receptors by the pentacyclic triterpene α,β-amyrin inhibits inflammatory and neuropathic persistent pain in mice". Pain. 152 (8): 1872–1887. doi:10.1016/j.pain.2011.04.005. ISSN 0304-3959. PMID 21620566. S2CID 23484784.
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