Amyrin: Difference between revisions
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| Name = Amyrins |
| Name = Amyrins |
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| ImageFile = alpha-amyrin.svg |
| ImageFile = alpha-amyrin.svg |
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| ImageSize = 200px |
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| ImageCaption = α-Amyrin |
| ImageCaption = α-Amyrin |
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| ImageFile1 = beta-amyrin.svg |
| ImageFile1 = beta-amyrin.svg |
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| ImageSize1 = 200px |
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| ImageCaption1 = β-Amyrin |
| ImageCaption1 = β-Amyrin |
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| IUPACName = α: (3β)-Urs-12-en-3-ol<br>β: (3β)-Olean-12-en-3-ol |
| IUPACName = α: (3β)-Urs-12-en-3-ol<br />β: (3β)-Olean-12-en-3-ol<br />δ: (3β)-Olean-13(18)-en-3-ol |
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| OtherNames = α: α-Amyrenol; α-Amirin; α-Amyrine; Urs-12-en-3β-ol; Viminalol<br>β: β-Amyrenol; β-Amirin; β-Amyrine; Olean-12-en-3β-ol; 3β-Hydroxyolean-12-ene |
| OtherNames = α: α-Amyrenol; α-Amirin; α-Amyrine; Urs-12-en-3β-ol; Viminalol<br />β: β-Amyrenol; β-Amirin; β-Amyrine; Olean-12-en-3β-ol; 3β-Hydroxyolean-12-ene |
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|Section1={{Chembox Identifiers |
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| CASNo = 638-95-9 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Comment = (α) |
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| CASNo1 = 559-70-6 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| CASNo1_Comment = (β) |
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| CASNo2 = 508-04-3 |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASNo2_Comment = (δ) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 30ZAG40J8N |
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| UNII_Comment = (α) |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = KM8353IPSO |
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| UNII1_Comment = (β) |
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| PubChem = 73170 |
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| PubChem1 = 73145 |
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| InChI_Comment = (α) |
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| PubChem2 = 12358447 |
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| InChIKey_Comment = (α) |
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| PubChem2_Comment = (δ) |
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| ChemSpiderID_Comment = (α) |
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| StdInChIKey = FSLPMRQHCOLESF-SFMCKYFRSA-N |
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| StdInChIKey_Comment = (α) |
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| ChemSpiderID2 = 26333109 |
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| SMILES1_Comment = (β) |
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| ChemSpiderID2_Comment = (δ) |
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| InChI1 = 1/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 |
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| InChI1_Comment = (β) |
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| InChIKey1_Comment = (β) |
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| StdInChI1 = 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 |
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| StdInChI1_Comment = (β) |
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| StdInChIKey1 = JFSHUTJDVKUMTJ-QHPUVITPSA-N |
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| SMILES1_Comment = (β) |
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| InChI3_Comment = (β) |
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}} |
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|Section2={{Chembox Properties |
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| C=30 | H=50 | O=1 |
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| Appearance = |
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| Density = |
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| MeltingPt = α: 186 °C<ref>''[[Merck Index]], 11th Edition, '''653'''</ref><br />β: 197-187.5 °C<ref>''[[Merck Index]], 11th Edition, '''654'''</ref> |
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| BoilingPt = |
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| Solubility = |
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}} |
}} |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = |
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The '''amyrins''' are three closely related natural chemical compounds of the [[triterpene]] class. They are designated α-amyrin (ursane skeleton),<ref>{{cite journal | pmid = 17473469 | volume=55 | issue=5 | title=Production of triterpene acids by cell suspension cultures of Olea europaea | journal=Chem Pharm Bull | pages=784–8 | last1 = Saimaru | first1 = H | last2 = Orihara | first2 = Y | last3 = Tansakul | first3 = P | last4 = Kang | first4 = YH | last5 = Shibuya | first5 = M | last6 = Ebizuka | first6 = Y | doi=10.1248/cpb.55.784| year=2007 | doi-access = free }}</ref> [[amyrin|β-amyrin]] (oleanane skeleton) <ref>{{cite journal | pmid = 16962103 | doi=10.1016/j.febslet.2006.08.044 | volume=580 | issue=22 | title=Dammarenediol-II synthase, the first dedicated enzyme for ginsenoside biosynthesis, in Panax ginseng | journal=FEBS Lett | pages=5143–9 | last1 = Tansakul | first1 = P | last2 = Shibuya | first2 = M | last3 = Kushiro | first3 = T | last4 = Ebizuka | first4 = Y| year=2006 | s2cid=20731479 | doi-access = free }}</ref> and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C<sub>30</sub>H<sub>50</sub>O. 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.<ref>{{cite journal |last1=Babalola |first1=Ibrahim T |last2=Shode |first2=Francis O |title=Ubiquitous Ursolic Acid: A Potential Pentacyclic Triterpene Natural Product |journal=Journal of Pharmacognosy and Phytochemistry |date=2013 |volume=2 |issue=2 |pages=214–222 |url=https://www.phytojournal.com/vol2Issue2/Issue_july_2013/37.1.pdf |access-date=31 October 2022 |language=en |issn=2278-4136}}</ref> All three amyrins occur in the surface wax of tomato fruit.<ref>{{cite journal|pmc=5278499 | pmid=28194155 | doi=10.3389/fpls.2017.00021 | volume=8 | title=Functional Characterization of CYP716 Family P450 Enzymes in Triterpenoid Biosynthesis in Tomato | journal=Front Plant Sci | page=21 | last1 = Yasumoto | first1 = S | last2 = Seki | first2 = H | last3 = Shimizu | first3 = Y | last4 = Fukushima | first4 = EO | last5 = Muranaka | first5 = T| year=2017 | doi-access=free }}</ref><ref name=Bauer>{{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 | |
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The '''amyrins''' are a pair of closely related natural chemical compounds of the [[triterpene]] class. They are designated α-amyrin and β-amyrin. Each has the chemical formula C<sub>30</sub>H<sub>50</sub>O. They are widely distributed in nature and have been isolated from a variety of plant sources. Alpha-amyrin is also found in [[dandelion coffee]]. |
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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 }}</ref> α-Amyrin is found in [[dandelion coffee]].{{citation needed|date=November 2016}} |
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A study demonstrated that α,β-amyrin exhibits long-lasting [[Nociception|antinociceptive]] and [[anti-inflammatory]] properties in 2 models of persistent nociception via activation of the [[cannabinoid receptor]]s [[Cannabinoid receptor type 1|CB1]] and [[Cannabinoid receptor type 2|CB2]] and by inhibiting the production of [[cytokine]]s and expression of [[NF-κB]], [[CREB]] and [[Prostaglandin-endoperoxide synthase 2|cyclooxygenase 2]].<ref>{{Cite journal|last1=Simão da Silva|first1=Kathryn A.B.|last2=Paszcuk|first2=Ana F.|last3=Passos|first3=Giselle F.|last4=Silva|first4=Eduardo S.|last5=Bento|first5=Allisson Freire|last6=Meotti|first6=Flavia C.|last7=Calixto|first7=João B.|date=August 2011|title=Activation of cannabinoid receptors by the pentacyclic triterpene α,β-amyrin inhibits inflammatory and neuropathic persistent pain in mice|journal=Pain|language=ENGLISH|volume=152|issue=8|pages=1872–1887|doi=10.1016/j.pain.2011.04.005|pmid=21620566|s2cid=23484784|issn=0304-3959}}</ref> |
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== References == |
== References == |
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{{reflist}} |
{{reflist}} |
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[[Category: |
[[Category:Secondary alcohols]] |
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[[Category:Triterpenes]] |
[[Category:Triterpenes]] |
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[[Category:Chemical compounds found in dandelion coffee]] |
Latest revision as of 11:29, 12 November 2023
α-Amyrin
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β-Amyrin
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Names | |
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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)
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ChemSpider | |
PubChem CID
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UNII |
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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).
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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]
- ^ Merck Index, 11th Edition, 653
- ^ Merck Index, 11th Edition, 654
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.