LIPID MAPS

Structure Database (LMSD)

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Common Name

oleanolic acid

Systematic Name

3β-hydroxyolean-12-en-28-oic acid

Synonyms

Astrantiagenin C
Caryophyllin
Giganteumgenin C
Oleanic acid
Virgaureagenin B

LM ID

LMPR0106150004

Formula

C₃₀H₄₈O₃

Exact Mass

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456.360345

Status

Curated

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Classification

Biological Context

Oleanolic acid is a pentacyclic triterpenoid that has been found in O. europaea and has diverse biological activities.^1,2,3,4,5 It is active against S. aureus, B. thuringiensis, E. coli, S. enterica, and S. dysenteriae (MICs = 1.9, 1.9, 7.8, 3.9, and 1.9 µg/ml, respectively) and scavenges hydroxyl and superoxide radicals in cell-free assays when used at a concentration of 1 mg/ml. Oleanolic acid is cytotoxic to DU145 prostate and MCF-7 breast cancer cells, as well as U87 glioblastoma cells, with IC50 values of 112.57, 132.29, and 163.6 µg/ml.³ It reduces LPS-induced adherence of THP-1 monocytes to human umbilical vein endothelial cells (HUVECs) in a co-culture model of monocyte-endothelial cell adhesion when used at concentrations ranging from 10 to 50 µM.⁴ Oleanolic acid (200 µmol/kg) decreases liver necrosis in several mouse models of liver injury, including those induced by acetaminophen , carbon tetrachloride (CCl4), or LPS/D-galactosamine.⁵

This information has been provided by Cayman Chemical

References

1. Liu, J., Liu, Y., and Klaassen, C.D. Protective effect of oleanolic acid against chemical-induced acute necrotic liver injury in mice. Zhongguo Yao Li Xue Bao 16(2), 97-102 (1995).

2. Lee, W., Yang, E.-J., Ku, S.-K., et al. Anti-inflammatory effects of oleanolic acid on LPS-induced inflammation in vitro and in vivo. Inflammation 36(1), 94-102 (2013).

3. Kim, G.-J., Jo, H.-J., Lee, K.-J., et al. Oleanolic acid induces p53-dependent apoptosis via the ERK/JNK/AKT pathway in cancer cell lines in prostatic cancer xenografts in mice. Oncotarget 9(41), 26370-26386 (2018).

4. Wang, J., Ren, H., Xu, Q.-L., et al. Antibacterial oleanane-type triterpenoids from pericarps of Akebia trifoliata. Food Chem. 168, 623-629 (2015).

5. Wang, X., Ye, X.-l., Liu, R., et al. Antioxidant activities of oleanolic acid in vitro: Possible role of Nrf2 and MAP kinases. Chem. Biol. Interact. 184(3), 328-337 (2010).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Olea europaea (#4146)

Magnoliopsida (#3398)

Triterpenes in husks of Olea europaea,
Phytochemistry, 1974

DOI: 10.1016/0031-9422(74)80325-0

String Representations

InChiKey (Click to copy)

MIJYXULNPSFWEK-GTOFXWBISA-N

InChi (Click to copy)

InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1

SMILES (Click to copy)

[C@@]12([C@]3(C)CC[C@]4(C(=O)O)[C@@]([H])(CC(C)(C)CC4)C3=CC[C@]1([H])[C@]1(C)[C@]([H])(C(C)(C)[C@@H](O)CC1)CC2)C