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Oleanolic acid

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Oleanolic acid
Oleanolic acid
Names
IUPAC name (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Other names Oleanic acid
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.347 Edit this at Wikidata
EC Number
  • 208-081-6
PubChem CID
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: MIJYXULNPSFWEK-GTOFXWBISA-N
  • Key: MIJYXULNPSFWEK-GTOFXWBIBS
  • Key: MIJYXULNPSFWEK-GTOFXWBISA-N
SMILES
  • O=C(O)54(/C3=C/C1(CC21(C)CC(O)C2(C)C)(C)3(C)CC4)CC(C)(C)CC5
Properties
Chemical formula C30H48O3
Molar mass 456.711 g·mol
Appearance light yellow
Melting point >300 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Oleanolic acid or oleanic acid is a naturally occurring triterpenoid, widely distributed in food and medicinal plants, related to betulinic acid. It can be found in Phytolacca americana (American pokeweed), and Syzygium spp, garlic, etc. It is relatively non-toxic, antitumor, and hepatoprotective, as well as exhibiting antiviral properties.

Oleanolic acid was found to exhibit strong anti-HIV activity, the related compound betulinic acid was used to create the first commercial maturation inhibitor drug. It was first studied and isolated from several plants, including Rosa woodsii (leaves), Prosopis glandulosa (leaves and twigs), Phordendron juniperinum (whole plant), Syzygium claviflorum (leaves), Hyptis capitata (whole plant), and Ternstromia gymnanthera (aerial part). Other Syzygium species including java apple (Syzygium samarangense) and rose apples contain it.

An extremely potent synthetic triterpenoid analogue of oleanolic acid was found in 2005, that is a powerful inhibitor of cellular inflammatory processes. They work by the induction by IFN- of inducible nitric oxide synthase (iNOS) and of cyclooxygenase 2 in mouse macrophages. They are extremely potent inducers of the phase 2 response (e.g., elevation of NADH-quinone oxidoreductase and heme oxygenase 1), which is a major protector of cells against oxidative and electrophile stress.

See also

References

  1. Oleanolic acid at Sigma-Aldrich
  2. Liu J (1995). "Pharmacology of oleanolic acid and ursolic acid". Journal of ethnopharmacology. 49 (2): 57–68. doi:10.1016/0378-8741(95)90032-2. PMID 8847885.
  3. Kishiwada, 1998
  4. Albena T. Dinkova-Kostova, Karen T. Liby, Katherine K. Stephenson, W. David Holtzclaw, Xiangqun Gao, Nanjoo Suh, Charlotte Williams, Renee Risingsong, Tadashi Honda, Gordon W. Gribble, Michael B. Sporn, and Paul Talalay (2005). "Extremely potent triterpenoid inducers of the phase 2 response: Correlations of protection against oxidant and inflammatory stress". Proceedings of the National Academy of Sciences of the United States of America. 102 (12): 4584–9. doi:10.1073/pnas.0500815102. PMC 555528. PMID 15767573.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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