Oleanolic acid
Encyclopedia
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.
Triterpenoid
Triterpenoids are terpenoid derviatives of triterpene molecules.They may have useful anti-cancer properties.Notable examples*Betulinic acid, possible anti-cancer drug*Bardoxolone methyl, inflammation modulator*Triterpenoid saponins...
, widely distributed in food and medicinal plants, related to betulinic acid
Betulinic acid
Betulinic acid is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase...
. It can be found in Phytolacca americana
Phytolacca americana
American Pokeweed is a large semi-succulent herbaceous perennial plant growing up to 10 feet in height. It is native to eastern North America, the Midwest, and the Gulf Coast, with more scattered populations in the far West...
(American pokeweed), and Syzygium
Syzygium
Syzygium is a genus of flowering plants that belongs to the myrtle family, Myrtaceae. The genus comprises about 1100 species, and has a native range that extends from Africa and Madagascar through southern Asia east through the Pacific...
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
HIV
Human immunodeficiency virus is a lentivirus that causes acquired immunodeficiency syndrome , a condition in humans in which progressive failure of the immune system allows life-threatening opportunistic infections and cancers to thrive...
activity, the related compound betulinic acid was used to create the first commercial maturation inhibitor
Maturation inhibitor
The maturation inhibitors are a class of antiviral drugs for the treatment of infection with HIV. They act by interfering with the maturation of the virus. Specifically, drugs in this class disrupt the final step in the processing of the HIV-1 Gag protein, leading to the formation of...
drug. It was first studied and isolated from several plants, including Rosa woodsii
Rosa woodsii
Rosa woodsii is a species of rose known by the common name Woods' rose. It is native to North America including much of Canada and Alaska and the western and central United States. It grows in a variety of habitat types, including disturbed areas....
(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
Syzygium samarangense
Syzygium samarangense is a plant species in the Myrtaceae, native to India, Indonesia, Malaysia, Philippines, Samoa, Sri Lanka and Thailand, and widely cultivated in the tropics...
) 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
Electrophile
In general electrophiles are positively charged species that are attracted to an electron rich centre. In chemistry, an electrophile is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to bond to a nucleophile...
stress.
See also
- Ursolic acidUrsolic acidUrsolic acid is a pentacyclic triterpene acid, used in cosmetics, that is also capable of inhibiting various types of cancer cells by inhibiting the STAT3 activation pathway and human fibrosarcoma cells by reducing the expression of matrix metalloproteinase-9 by acting through the glucocorticoid...
- Moronic acidMoronic acidMoronic acid is a natural triterpene. Moronic acid can be extracted from Rhus javanica, a sumac plant traditionally believed to hold medicinal applications...
- Momordin (saponin)Momordin (saponin)Momordin is one of several saponins derived from oleanolic acid, a triterpenoid. These chemical compounds are found in some plants of the Momordica genus, which includes the bitter melon and the balsam apple Momordin is one of several saponins derived from oleanolic acid, a triterpenoid. These...
, a glycosideGlycosideIn chemistry, a glycoside is a molecule in which a sugar is bound to a non-carbohydrate moiety, usually a small organic molecule. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme...
of oleanolic acid. - List of phytochemicals and foods in which they are prominent