Cannabaceae

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]

References[edit]

  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". Chem Pharm Bull. 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 Lett. 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". Front Plant Sci. 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.

One thought on “Cannabaceae

  1. Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
    View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction

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