Oleanolic acid

From Wikipedia, the free encyclopedia
Oleanolic acid[1]
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 508-02-1 YesY
PubChem 10494
ChemSpider 10062 YesY
EC number 208-081-6
ChEBI CHEBI:37659 N
ChEMBL CHEMBL168 YesY
Jmol-3D images {{#if:O=C(O)[C@@]54[C@H](/C3=C/C[C@H]1[C@](CC[C@@H]2[C@]1(C)CC[C@H](O)C2(C)C)(C)[C@]3(C)CC4)CC(C)(C)CC5|Image 1
Properties
Molecular formula C30H48O3
Molar mass 456.70 g mol−1
Appearance White
Melting point >300 °C
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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, hepatoprotective, and exhibits antitumor and antiviral properties.[2]

Oleanolic acid was found to exhibit weak anti-HIV[3] and weak anti-HCV activities, but more potent synthetic analogs are being investigated as potential drugs.[4]

An extremely potent synthetic triterpenoid analog 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.[5]

Natural occurrences

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), Mirabilis jalapa[6] and Ternstromia gymnanthera (aerial part). Other Syzygium species including java apple (Syzygium samarangense) and rose apples contain it.

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. ↑ Mengoni, F; Lichtner, M; Battinelli, L; Marzi, M; Mastroianni, CM; Vullo, V; Mazzanti, G (2002). "In vitro anti-HIV activity of oleanolic acid on infected human mononuclear cells". Planta medica 68 (2): 111–4. doi:10.1055/s-2002-20256. PMID 11859458. 
  4. ↑ Yu, Fei; Wang, Qi; Zhang, Zhen; Peng, Yi-yun; Qiu, Yun-yan; Shi, Yong-Ying; Zheng, Yong-Xiang; Xiao, Su-Long; Wang, Han; Huang, Xiaoxi; Zhu, Linyi; Chen, Kunbo; Zhao, Chuanke; Zhang, Chuanling; Yu, Maorong; Sun, Dian; Zhang, Lihe; Zhou, Demin (2013). "Development of Oleanane-Type Triterpenes as a New Class of HCV Entry Inhibitors". Journal of Medicinal Chemistry 56 (11): 130510090711006. doi:10.1021/jm301910a. 
  5. ↑ 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. 
  6. ↑ Constituents of Mirabilis jalapa. Siddiqui S., Siddiqui B.S., Adil Q. and Begum S., Fitoterapia, 1990, Volume 61, No. 5, page 471 (abstract)
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