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
ChEMBL
ChemSpider
ECHA InfoCard 100.007.347
EC Number 208-081-6
Properties
C30H48O3
Molar mass 456.711 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, male rats regained fertility and successfully impregnated female rats.[9]

See also[edit]

References[edit]

  1. ^ "Oleanolic acid". Sigma-Aldrich. Merck. Retrieved November 29, 2018.
  2. ^ Pollier J, Goossens A (May 2012). "Oleanolic acid". Phytochemistry. 77: 10–15. doi:10.1016/j.phytochem.2011.12.022. PMID 22377690.
  3. ^ "Oleanolic acid (HMDB0002364)". HMDB. Canadian Institutes of Health Research. Retrieved November 29, 2018.
  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 (December 1995). "Pharmacology of oleanolic acid and ursolic acid". J Ethnopharmacol. 49 (2): 57–68. doi:10.1016/0378-8741(95)90032-2. PMID 8847885.
  6. ^ Mengoni F, Lichtner M, Battinelli L, Marzi M, Mastroianni CM, Vullo V, Mazzanti G (February 2002). "In vitro anti-HIV activity of oleanolic acid on infected human mononuclear cells". Planta Med. 68 (2): 111–4. doi:10.1055/s-2002-20256. PMID 11859458.
  7. ^ Yu F, Wang Q, Zhang Z, Peng Y, Qiu Y, Shi Y, et al. (June 2013). "Development of oleanane-type triterpenes as a new class of HCV entry inhibitors". J. Med. Chem. 56 (11): 4300–19. doi:10.1021/jm301910a. PMID 23662817.
  8. ^ Dinkova-Kostova AT, Liby KT, Stephenson KK, Holtzclaw WD, Gao X, Suh N, et al. (March 2005). "Extremely potent triterpenoid inducers of the phase 2 response: correlations of protection against oxidant and inflammatory stress". Proc. Natl. Acad. Sci. U.S.A. 102 (12): 4584–9. doi:10.1073/pnas.0500815102. PMC 555528. PMID 15767573.
  9. ^ Mdhluli MC, van der Horst G (October 2002). "The effect of oleanolic acid on sperm motion characteristics and fertility of male Wistar rats". Lab. Anim. 36 (4): 432–7. doi:10.1258/002367702320389107. PMID 12396287.