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Acido Ursolico y Oleanolico. Datos de Interes

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Antiguo 03-07-2012, 20:47
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Predeterminado Acido Ursolico y Oleanolico. Datos de Interes


Ursolic acid (3-β-hydroxy-urs-12-en-28-oic acid) and oleanolic acid (3β-Hydroxy-5α-olean-12-en-28-oic acid) are pentacyclic triterpenes found in food, herbs and other plants. Oleanolic acid differs from ursolic acid only in the position of the C-29 methyl group, and the two are virtually always found together in nature. On paper, they appear to be among most active natural molecules known to man, as researchers have observed them elicit potent antioxidant, enzyme inhibitory, hypoglycemic, hypolipidemic, anti-viral/bacterial/fungal, and, particularly in Ursolic acid's case, anabolic/anti-catabolic effects.

Biosynthetic pathway:

squalene --> alpha-amyrin --> UA.
squalene --> beta-amyrin --> OA

Documented activity:

Hepatoprotective antioxidant:

Oleanolic acid tablets are widely marketed as an OTC treatment for liver diseases in China.

...Yet ursolic acid has been observed to be generally more potent at reducing toxin-induced liver injury in mice. In another recent study utilizing rats with alcohol-induced liver injury, ursolic acid reduced hepatic lipid peroxidation and increased levels of circulatory antioxidants such as glutathione, ascorbic acid and α-tocopherol. Body weight and feeding parameters of treated mice showed marked improvement. In closing the abstract, the researchers noted that "the activity of ursolic acid (20 mg/kg) compares well with silymarin, a known hepatoprotective drug, and seems to be better in certain parameters."

Ursolic acid also induces the hepatotoxin-clearing antioxidant peptide metallotheonein.

There are dozens of studies which concern the hepatoprotective properties of oleanolic acid. Like UA, it seems to work primarily via metallothionein induction and stimulation of glutathione turnover. Interestingly, OA was recently shown to interact with the farnesoid X receptor, (bile acid receptor,) where it modulates the expression of important genes involved in bile acid transport. Whether UA also interacts with the FXR is unknown.

Aromatase inhibitor:

Oleanolic and Ursolic acids are very weak inhibitors of aromatase. So weak, in fact, that this property is almost entirely irrelevant. (A Ki of 32microM is pushing it for relevance even in compounds which have good bioavailability.)

Interestingly, in a very strange Chinese study which lies somewhere between modern medicine and TCM, oral administration of oleanolic/ursolic acid (from fructus ligustri lucidi) increased hypothalamic androgen receptor mRNA expression and decreased estrogen receptor mRNA expression. These changes were primarily observed in male animals.

TGF-Beta inhibitor:

Ursolic acid has been shown to be a potent antagonist of TGF-beta1. This may have something to do with its anabolic/anti-catabolic properties, as TGF-beta1 is expressed in skeletal muscle where it is a potent inhibitor of differentiation, growth, and regenerative capacity. People with Marfan Syndrome, who have increased TGF-beta1 signaling activity due to fibrillin-1 deficiency, often report an inability to gain muscle size after exercise. This same effect has been observed in fibrillin-1-deficient mice.

... I've seen some claims that ursolic acid can inhibit myostatin, and I wonder if this TGF-β1 inhibition is what's behind them. Myostatin is indeed a member of theTGF-β superfamily... But myostatin is not TGF-beta1: They are two different proteins which bind to different receptors and are very differently expressed. (TGF-beta1-null mice are nothing like myostatin-null mice.) I have seen no evidence which might suggest that myostatin itself is inhibited by oleanolic acid or ursolic acid, and no evidence which might suggest that follistatin is somehow upregulated by 'em.

The study which described ursolic acid-induced TGF-beta1 inhibition was performed in vitro, and although UA appears to be rather potent based on the inhibitor constant it was assigned, this effect has not yet been observed in vivo.


In a study which used rats with streptozotocin-induced diabetes, treatment with oleanolic acid increased serum insulin levels, lowered total cholesterol, improved the ratio of LDL to HDL, and promoted weight gain. The researchers speculated that OA might induce insulin release. A few in vitro studies strongly support this assumption -- one came to the conclusion that treatment with OA directly induces insulin secretion & increases insulin mRNA expression in rat islets after prolonged exposure, another observed that OA stimulates insulin secretion in INS-1 cells.

In a study which used streptozotocin-nicotinamide diabetic mice, treatment with ursolic acid also improved blood glucose, insulin tolerance, etc. Interestingly, perhaps predictably, it sharply increased plasma and pancreatic insulin levels; metformin, the positive control, increased pancreatic insulin levels but did not increase plasma insulin.

So the mechanism of action, common to both OA and UA, seems to involve the stimulation of insulin secretion. There is also some evidence to suggest that increased insulin receptor phosphorylation may be involved.

Oleanolic acid glycosides -- possibly present in commercially-available OA/UA extracts -- have also been shown to have antidiabetic properties. The mechanism of action is different here and involves the inhibition of gastric emptying and glucose-uptake in the small intestine. SAR experiments were carried out where it was determined that the 3-O-glycoside moiety is essential to this activity. Delayed gastric emptying can reduce appetite, which is an effect that people using UA/OA-bearing extracts seem to have noticed.

Corosolic acid, a pentacyclic triterpene found in Lagerstroemia speciosa, is very well known for its anti-diabetic properties & has been a popular nutritional supplement for many years. Despite a striking structural similarity to ursolic acid, its mechanism of action appears to be rather different , and diabetic mice treated with CA have significantly reduced insulin levels when compared to controls.

Anti-fertility agent:

A number of studies have been published with regards to the anti-fertility properties of oleanolic acid. It appears that the oral administration of moderate doses of oleanolic acid to rats leads to temporary and reversible infertility, without a reduction in libido, without affecting bodyweight, and without reducing sperm count. The mechanism of action here has not been fully established, but it looks like oleanolic acid sensitizes sperm cells to calcium ions. Calcium exchange is important to cellular motion, and so these over-sensitized sperm cells become hypermobile and whip around in erratic circles instead of in a forward trajectory.

...It must be said that this effect has never been observed in humans, and is completely temporary in rats. Within 14 days of their last dose, all OA-treated rats were able to impregnate females & their 'sperm motility characteristics' returned to normal.


The anabolic/anti-catabolic effects of ursolic acid were the subject of a study which was thoroughly summarized by Patrick Arnold. So I'll go over the main points only very briefly:
--Ursolic acid increases skeletal muscle IGF-1 expression both in vitro and in live rats who were treated with it.

--Exposure to ursolic acid decreases the expression of mRNA associated with catabolic processes.
--Ursolic acid was fed to mice, orally, and induced skeletal muscle hypertrophy. In a separate experiment, it also delayed muscle atrophy in denervated muscle fibers.

Other activity

Ursolic acid and oleanolic acid have many more biological properties. This activity has been well-summarized elsewhere. They are antinociceptive , anti-inflammatory , anti-microbial , they induce apoptosis in various cancer cell lines , and they appear to have some cardioprotective ability.
The links provided are just the tip of the iceberg. Were I to go into all of these effects in detail, I believe I would have enough material to write a book. These triterpenes are extraordinarily biologically-active.

Useful information:


The solubility of a 19% oleanolic acid and 79% ursolic acid extract was tested in various solvents. The results were roughly as follows:

Acetone: 8.2mg/ml
Ethanol: 16.8mg/ml
Isopropanol: 16.9mg/ml
n-Butanol: 31.9mg/ml
THF: 48.8mg/ml

Ursolic acid and oleanolic acid are extremely hydrophobic and are completely insoluble in water. Their very poor solubilities in ethanol, isopropanol, and oils make transdermal formulations and injectable solutions virtually impossible without extensive (read: costly and difficult) pre-treatment.
Pure oleanolic acid seems to be roughly 10-20% more soluble than pure ursolic acid.


Oleanolic acid: 0.7% (oral administration to rats.)
Ursolic acid: Undocumented. Presumably similar.

Half-life: Oleanolic acid:: 8.7 hours (oral administration of a 40mg capsule to human male volunteers.)
Peak plasma concentration (Cmax) was 12.1 ng/ml. The time to reach Cmax (Tmax) was 5.2 hours -- a fact which indicates that OA is slowly absorbed.

Ursolic acid: I am unaware of any human oral data.
...In rats, orally-administered ursolic acid seems to have a half-life of 4.3 hours. In rats, orally-administered oleanolic acid, at a slightly reduced dose, has a half-life of 65 minutes. Rat half-lives are often much shorter than human half-lives. It stands to reason that, in humans, the half-life of orally-administered ursolic acid may be 9-10 hours or longer.


Oleanolic acid: LD50 = >2000mg/kg. (Oral administration to mice.)
Ursolic acid: LD50 = >2000mg/kg. (Oral administration to mice.)

Both UA and OA are essentially non-toxic. OA, in particular, is widely used in China -- both in tablets and in fructus ligustri lucidi (nu zhen zhi) preparations -- where, to the best of my knowledge, no adverse effects have ever been reported.

Structure-Activity Relationship

A SAR was attempted, but focused mostly on the anti-viral, anti-cancer, and anti-inflammatory traits of these compounds. Even so, it is largely incomplete and much is still unknown. Where the other diverse functions of these molecules are concerned, we don't have nearly enough information to attempt any sort of SAR analysis.


Ursolic and oleanolic acid appear to be very useful supplements, limited only by very poor bioavailability and solubility. This problem will likely be worked out in the future. In the meantime, I think that UA products are certainly worth trying... if you don't mind swallowing lots of capsules, that is.

Pd: Si teneis mucho interes en que incluya las referencias me lo comentais, porque tendria que prepararlas para incluirlas y me llevaria un rato.

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Antiguo 03-07-2012, 22:53
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Mira, al menos se que con el ursobolic no me saldrán teticas
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Antiguo 03-07-2012, 23:03
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Iniciado por darkhugo Ver Mensaje
Mira, al menos se que con el ursobolic no me saldrán teticas

yo me noto la zona abdominal mas prieta
y los antebrazos
como mas duro
no se, es una sensacion mia

18 pirulas al dia, esta pegando el bote un bajon!
con la pasta del ursobolico
me daba para un mes de 11-keto

tambien tengo menos apetito
pero eso mas bien,se lo,achaco a la 7-keto
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Antiguo 04-07-2012, 00:34
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me daba para un mes de 11-keto
11-Keto Rules!!!
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