Amyrin

Amyrins

α-Amyrin

β-Amyrin
Names
IUPAC names
α: (3β)-Urs-12-en-3-ol
β: (3β)-Olean-12-en-3-ol
δ: (3β)-Olean-13(18)-en-3-ol
Other names
α: α-Amyrenol; α-Amirin; α-Amyrine; Urs-12-en-3β-ol; Viminalol
β: β-Amyrenol; β-Amirin; β-Amyrine; Olean-12-en-3β-ol; 3β-Hydroxyolean-12-ene
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C30H50O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h9,19-20,22-25,31H,10-18H2,1-8H3/t19-,20+,22+,23-,24+,25+,27-,28+,29-,30-/m1/s1
    Key: FSLPMRQHCOLESF-SFMCKYFRSA-N
  • (β): InChI=1S/C30H50O/c1-25(2)15-16-27(5)17-18-29(7)20(21(27)19-25)9-10-23-28(6)13-12-24(31)26(3,4)22(28)11-14-30(23,29)8/h9,21-24,31H,10-19H2,1-8H3/t21-,22-,23+,24-,27+,28-,29+,30+/m0/s1
    Key: JFSHUTJDVKUMTJ-QHPUVITPSA-N
  • (α): O[C@H]2CC[C@@]1([C@@H]3[C@](CC[C@H]1C2(C)C)(C)[C@]5(C(=C/C3)\[C@@H]4[C@@H](C)[C@H](C)CC[C@]4(C)CC5)C)C
  • (β): C[C@@]12CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]1CC(CC2)(C)C)C
Properties
C30H50O
Molar mass 426.729 g·mol−1
Melting point α: 186 °C[1]
β: 197-187.5 °C[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

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]

  1. ^ Merck Index, 11th Edition, 653
  2. ^ Merck Index, 11th Edition, 654
  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". Chemical and Pharmaceutical Bulletin. 55 (5): 784–8. doi:10.1248/cpb.55.784. PMID 17473469.
  4. ^ Tansakul, P; Shibuya, M; Kushiro, T; Ebizuka, Y (2006). "Dammarenediol-II synthase, the first dedicated enzyme for ginsenoside biosynthesis, in Panax ginseng". FEBS Letters. 580 (22): 5143–9. doi:10.1016/j.febslet.2006.08.044. PMID 16962103. S2CID 20731479.
  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. ^ Yasumoto, S; Seki, H; Shimizu, Y; Fukushima, EO; Muranaka, T (2017). "Functional Characterization of CYP716 Family P450 Enzymes in Triterpenoid Biosynthesis in Tomato". Frontiers in Plant Science. 8: 21. doi:10.3389/fpls.2017.00021. PMC 5278499. PMID 28194155.
  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. ^ 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.