Amyrin: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
m →‎top: Journal cites, Added 1 doi to a journal cite using AWB (12158)
Fixed typo
Line 56: Line 56:
}}
}}


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 | title=Production of triterpene acids by cell suspension cultures of Olea europaea | journal=Chem Pharm Bull (Tokyo) | 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}}</ref> β-amyrin (oleanane skeleton) <ref>{{cite journal | pmid = 16962103 | doi=10.1016/j.febslet.2006.08.044 | volume=580 | 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}}</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>http://www.phytojournal.com/vol2Issue2/Issue_july_2013/37.1.pdf</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}}</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 |
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 | title=Production of triterpene acids by cell suspension cultures of Olea europaea | journal=Chem Pharm Bull (Tokyo) | 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}}</ref> β-amyrin (oleanane skeleton) <ref>{{cite journal | pmid = 16962103 | doi=10.1016/j.febslet.2006.08.044 | volume=580 | 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}}</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>http://www.phytojournal.com/vol2Issue2/Issue_july_2013/37.1.pdf</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}}</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 |
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}}</ref> α-Amyrin is found in [[dandelion coffee]].{{citation needed|date=November 2016}}
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}}</ref> α-Amyrin is found in [[dandelion coffee]].{{citation needed|date=November 2016}}


Revision as of 09:58, 30 August 2017

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
  • 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]

References

  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. "Production of triterpene acids by cell suspension cultures of Olea europaea". Chem Pharm Bull (Tokyo). 55: 784–8. PMID 17473469.
  4. ^ Tansakul, P; Shibuya, M; Kushiro, T; Ebizuka, Y. "Dammarenediol-II synthase, the first dedicated enzyme for ginsenoside biosynthesis, in Panax ginseng". FEBS Lett. 580: 5143–9. doi:10.1016/j.febslet.2006.08.044. PMID 16962103.
  5. ^ http://www.phytojournal.com/vol2Issue2/Issue_july_2013/37.1.pdf
  6. ^ Yasumoto, S; Seki, H; Shimizu, Y; Fukushima, EO; Muranaka, T. "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.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  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.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Amyrin&oldid=797990150"