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Structure Database (LMSD)

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Common Name

beta-Amyrin

Systematic Name

Olean-12-en-3β-ol

Synonyms

LM ID

LMPR0106150015

Formula

C₃₀H₅₀O

Exact Mass

Calculate m/z

426.386165

Status

Curated

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Classification

Biological Context

β-Amyrin is a natural pentacyclic triterpenoid commonly found in plants. It is a member of the oleanane group of secondary metabolites biosynthesized from squalene in the triterpenoid pathway. β-Amyrin inhibits collagen-induced platelet aggregation (IC50 = 10.5 µM), inhibits acetylcholinesterase (IC50 = 165 µM), and has antifungal and hepatoprotective effects.^1,2,3,4 Extracts of certain plants, used in herbal medicine to treat inflammation, have been shown to contain β-amyrin, suggesting that this compound contributes to anti-inflammatory actions.⁵

This information has been provided by Cayman Chemical

References

1. Ching, J., Chua, T.K., Chin, L.C., et al. Beta-amyrin from Ardisia elliptica Thunb. is more potent than aspirin in inhibiting collagen-induced platelet aggregation. Indian J. Exp. Biol. 48(3), 275-279 (2010).

2. Ferraz-Filha, Z.S., de Paula Michel Araújo, M.C., Ferrari, F.C., et al. Tabebuia roseoalba: In vivo hypouricemic and anti-inflammatory effects of its ethanolic extract and constituents. Planta Med. 82(16), 1395-1402 (2016).

3. Jabeen, K., Javid, A., Ahmad, E., et al. Antifungal compounds from Melia azedarach leaves for management of Ascochyta rabiei, the cause of chickpea blight. Nat. Prod. Res. 25(3), 264-276 (2011).

4. Oliveira, F.A., Chaves, M.H., Almeida, F.R., et al. Protective effect of alpha- and beta-amyrin, a triterpene mixture from Protium heptaphyllum (Aubl.) March. trunk wood resin, against acetaminophen-induced liver injury in mice. J. Ethnopharmacol. 98(1-2), 103-108 (2005).

5. Park, S.J., Ahn, Y.J., Oh, S.R., et al. Amyrin attenuates scopolamine-induced cognitive impairment in mice. Biol. Pharm. Bull. 37(7), 1207-1213 (2014).

String Representations

InChiKey (Click to copy)

JFSHUTJDVKUMTJ-QHPUVITPSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

[C@@]12(C)CC[C@@]3([H])C(C)(C)[C@H](CC[C@]3(C)[C@@]1([H])CC=C1[C@]3([H])CC(CC[C@@]3(CC[C@@]21C)C)(C)C)O