Oleanolic acid

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Oleanolic acid[1]
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.347
EC Number 208-081-6
Properties
C30H48O3
Molar mass 456.71 g·mol−1
Appearance White
Melting point > 300 °C (572 °F; 573 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins.[2]

Natural occurrence[edit]

Oleanolic acid can be found in olive oil, Phytolacca americana (American pokeweed), and Syzygium spp, garlic, etc. It was first studied and isolated from several plants, including Olea europaea[3] (leaves, fruit), Rosa woodsii (leaves), Prosopis glandulosa (leaves and twigs), Phoradendron juniperinum (whole plant), Syzygium claviflorum (leaves), Hyptis capitata (whole plant), Mirabilis jalapa[4] and Ternstroemia gymnanthera (aerial part). Other Syzygium species including java apple (Syzygium samarangense) and rose apples contain it.

Pharmacological research[edit]

Oleanolic acid is relatively non-toxic, hepatoprotective, and exhibits antitumor and antiviral properties.[5]

Oleanolic acid was found to exhibit weak anti-HIV[6] and weak anti-HCV activities in vitro, but more potent synthetic analogs are being investigated as potential drugs.[7]

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-γ 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.[8]

A 2002 study in Wistar rats found that oleanolic acid reduced sperm quality and motility, causing infertility. After withdrawing exposure, mice regained fertility and successfully impregnated female mice.[9]

See also[edit]

References[edit]

  1. ^ Oleanolic acid at Sigma-Aldrich
  2. ^ Pollier, J., Goossens, A. (2012). "Oleanolic acid". Phytochemistry. 77: 10–15. PMID 22377690. doi:10.1016/j.phytochem.2011.12.022. 
  3. ^ HMDB entry for Oleanolic acid
  4. ^ Constituents of Mirabilis jalapa. Siddiqui S., Siddiqui B.S., Adil Q. and Begum S., Fitoterapia, 1990, Volume 61, No. 5, page 471 (abstract)
  5. ^ Liu J (1995). "Pharmacology of oleanolic acid and ursolic acid". Journal of Ethnopharmacology. 49 (2): 57–68. PMID 8847885. doi:10.1016/0378-8741(95)90032-2. 
  6. ^ 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. PMID 11859458. doi:10.1055/s-2002-20256. 
  7. ^ 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. PMID 23662817. doi:10.1021/jm301910a. 
  8. ^ 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 & 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. PMC 555528Freely accessible. PMID 15767573. doi:10.1073/pnas.0500815102. 
  9. ^ Mdhluli, M.C.; G. van der Horst (2002). "The effect of oleanolic acid on sperm motion characteristics and fertility of male Wistar rats".