Oleanolic acid: Difference between revisions

Latest revision as of 05:54, 16 February 2025

Oleanolic Acid[edit]

Oleanolic acid is a naturally occurring triterpenoid found in various plants, including olives, grapes, and jasmine. It is known for its potential therapeutic properties, including anti-inflammatory, antioxidant, and hepatoprotective effects.

Structure and Properties[edit]

Oleanolic acid is a pentacyclic triterpenoid with the chemical formula C₃₀H₄₈O₃. It is a white, crystalline substance that is insoluble in water but soluble in organic solvents such as ethanol and chloroform. The structure of oleanolic acid consists of a five-ring backbone typical of triterpenoids, with a carboxylic acid group at the C-28 position.

Biosynthesis[edit]

The biosynthesis of oleanolic acid involves the cyclization of squalene to form the triterpenoid skeleton. This process is catalyzed by the enzyme oxidosqualene cyclase, which converts 2,3-oxidosqualene into the oleanane-type triterpenoid structure. Subsequent enzymatic modifications, including oxidation and glycosylation, lead to the formation of oleanolic acid.

Biological Activities[edit]

Oleanolic acid exhibits a wide range of biological activities:

Anti-inflammatory: It inhibits the production of pro-inflammatory cytokines and mediators, making it a potential therapeutic agent for inflammatory diseases.
Antioxidant: Oleanolic acid scavenges free radicals and enhances the activity of antioxidant enzymes, protecting cells from oxidative stress.
Hepatoprotective: It protects the liver from damage caused by toxins and oxidative stress, and is used in traditional medicine for liver disorders.
Anticancer: Studies suggest that oleanolic acid can induce apoptosis and inhibit the proliferation of cancer cells.

Applications[edit]

Oleanolic acid is used in various applications due to its beneficial properties:

In cosmetics, it is used for its anti-aging and skin-protective effects.
In pharmaceuticals, it is explored as a potential therapeutic agent for liver diseases, cancer, and inflammatory conditions.
In food, it is present in small amounts in edible plants and contributes to their health benefits.

Related Pages[edit]

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-'''Oleanolic acid''' is a naturally occurring [[triterpenoid]], widely distributed in food and medicinal plants, related to [[betulinic acid]]. It can be found in a large variety of plants, including [[Olea europaea]] (olive), [[Garcinia indica]] (kokum), [[Eucalyptus]] spp., and [[Phyllanthus amarus]] (stonebreaker).
+{{DISPLAYTITLE:Oleanolic Acid}}
-==Chemistry==
+== Oleanolic Acid ==
-Oleanolic acid is a pentacyclic triterpenoid compound with a formula of C30H48O3. It is related to [[betulinic acid]] and has a similar molecular structure. The compound is one of the [[triterpenes]], a class of chemical compounds composed of three [[terpene]] units with the molecular formula C30H48; the structure of triterpenes is considered to be derived from the 30-carbon skeleton of [[squalene]].
+[[File:Oleanolic_Acid_Biosynthesis.gif|thumb|right|Oleanolic acid biosynthesis]]
+'''Oleanolic acid''' is a naturally occurring [[triterpenoid]] found in various plants, including [[olive]]s, [[grape]]s, and [[jasmine]]. It is known for its potential therapeutic properties, including anti-inflammatory, antioxidant, and hepatoprotective effects.
-==Sources==
+== Structure and Properties ==
-Oleanolic acid is found in a wide variety of plants worldwide. It is present in significant quantities in the olive tree ([[Olea europaea]]), and is also found in a variety of other food plants and medicinal herbs. These include the kokum tree ([[Garcinia indica]]), various species of eucalyptus ([[Eucalyptus]] spp.), and the stonebreaker plant ([[Phyllanthus amarus]]).
+Oleanolic acid is a pentacyclic triterpenoid with the chemical formula C<sub>30</sub>H<sub>48</sub>O<sub>3</sub>. It is a white, crystalline substance that is insoluble in water but soluble in organic solvents such as ethanol and chloroform. The structure of oleanolic acid consists of a five-ring backbone typical of triterpenoids, with a carboxylic acid group at the C-28 position.
-==Health Benefits==
+== Biosynthesis ==
-Oleanolic acid has been studied for its potential health benefits. It has been found to have [[hepatoprotective]] properties, meaning it can protect the liver from damage. It also has [[anti-inflammatory]], [[antioxidant]], and [[antitumor]] properties. Some studies have suggested that oleanolic acid may have potential as a treatment for [[cancer]], [[diabetes]], and [[heart disease]].
+The biosynthesis of oleanolic acid involves the cyclization of [[squalene]] to form the triterpenoid skeleton. This process is catalyzed by the enzyme [[oxidosqualene cyclase]], which converts 2,3-oxidosqualene into the oleanane-type triterpenoid structure. Subsequent enzymatic modifications, including oxidation and glycosylation, lead to the formation of oleanolic acid.
-==Safety and Toxicity==
+== Biological Activities ==
-While oleanolic acid is generally considered safe, it can be toxic in large amounts. It is important to consult with a healthcare provider before starting any new supplement regimen.
+Oleanolic acid exhibits a wide range of biological activities:
-==See Also==
+* '''Anti-inflammatory''': It inhibits the production of pro-inflammatory cytokines and mediators, making it a potential therapeutic agent for inflammatory diseases.
+* '''Antioxidant''': Oleanolic acid scavenges free radicals and enhances the activity of antioxidant enzymes, protecting cells from oxidative stress.
+* '''Hepatoprotective''': It protects the liver from damage caused by toxins and oxidative stress, and is used in traditional medicine for liver disorders.
+* '''Anticancer''': Studies suggest that oleanolic acid can induce apoptosis and inhibit the proliferation of cancer cells.
+== Applications ==
+Oleanolic acid is used in various applications due to its beneficial properties:
+* In [[cosmetics]], it is used for its anti-aging and skin-protective effects.
+* In [[pharmaceuticals]], it is explored as a potential therapeutic agent for liver diseases, cancer, and inflammatory conditions.
+* In [[food]], it is present in small amounts in edible plants and contributes to their health benefits.
+== Related Pages ==
 * [[Triterpenoid]]
-* [[Betulinic acid]]
+* [[Squalene]]
-* [[Olea europaea]]
+* [[Oxidosqualene cyclase]]
-* [[Garcinia indica]]
+* [[Antioxidant]]
-* [[Eucalyptus]]
+* [[Hepatoprotective agent]]
-* [[Phyllanthus amarus]]
-[[Category:Chemical compounds]]
+[[Category:Triterpenoids]]
-[[Category:Natural compounds]]
+[[Category:Phytochemicals]]
-[[Category:Medicinal plants]]
+[[Category:Antioxidants]]
-[[Category:Food ingredients]]
-{{Chemistry-stub}}
-{{Medicine-stub}}