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 | |
508-02-1  | |
| ChEBI | CHEBI:37659  |
| ChEMBL | ChEMBL168 |
| ChemSpider | 10062 |
| EC number | 208-081-6 |
| |
| Jmol-3D images | Image |
| PubChem | 10494 |
| |
| Properties | |
| Molecular formula |
C30H48O3 |
| Molar mass | 456.70 g·mol−1 |
| Appearance | White |
| Melting point | > 300 °C (572 °F; 573 K) |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| Infobox references | |
Oleanolic acid or oleanic acid is a naturally occurring triterpenoid, widely distributed in food, medicinal plants, and nutritional supplements[2] related to betulinic acid. It can be found in Olive oil, Phytolacca americana (American pokeweed), and Syzygium spp, garlic, etc. It is relatively non-toxic, hepatoprotective, and exhibits antitumor and antiviral properties.[3]
Oleanolic acid was found to exhibit weak anti-HIV[4] and weak anti-HCV activities, but more potent synthetic analogs are being investigated as potential drugs.[5]
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.[6]
Natural occurrences
It was first studied and isolated from several plants, including Olea europaea[7] (leaves, fruit), Rosa woodsii (leaves), Prosopis glandulosa (leaves and twigs), Phordendron juniperinum (whole plant), Syzygium claviflorum (leaves), Hyptis capitata (whole plant), Mirabilis jalapa[8] and Ternstromia gymnanthera (aerial part). Other Syzygium species including java apple (Syzygium samarangense) and rose apples contain it.
Use as Male Contraceptive
A 2002 study in Wistar mice found that oleanolic acid reversibly induced infertility in mice due to reduced sperm quality and motility, at a dose of 16 mg/kg for 30 days. After withdrawing this treatment, mice regained fertility and successfully impregnated female mice.[9]
See also
- Ursolic acid
- Moronic acid
- Momordin (saponin), a glycoside of oleanolic acid
- List of phytochemicals in food
References
- ↑ Oleanolic acid at Sigma-Aldrich
- ↑ http://soleaus.com
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ HMDB entry for Oleanolic acid
- ↑ Constituents of Mirabilis jalapa. Siddiqui S., Siddiqui B.S., Adil Q. and Begum S., Fitoterapia, 1990, Volume 61, No. 5, page 471 (abstract)
- ↑ Mdhluli, M.C.; G. van der Horst (2002). "The effect of oleanolic acid on sperm motion characteristics and fertility of male Wistar rats".