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CAS NUMBER: 77-52-1
EC NUMBER: 201-034-0
MOLECULAR FORMULA: C30H48O3
MOLECULAR WEIGHT: 456.7
Ursolic Acid is a lipophilic pentacyclic triterpenoid, especially abundant in apple peel, with anti-inflammatory and antihyperlipidemic properties.
Ursolic Acid is a pentacyclic triterpene acid present in many plants, including apples, bilberries, cranberries, elder flower, peppermint, lavender, oregano, thyme, hawthorn, prunes.
Ursolic Acid has many pharmacological effects including the antioxidant, antiinflammatory, antibacterial, and antifungal properties.
Ursolic Acid is a pentacyclic triterpenoid identified in the epicuticular waxes of apples and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.
Ursolic Acid is present in many plants, such as Mirabilis jalapa, as well as in many fruits and herbs used in daily life.
Ursolic Acid is a weak aromatase inhibitor.
Under physiological concentrations, Ursolic Acid also induces eryptosis.
Ursolic acid (sometimes referred to as urson, prunol, malol, or 3β-hydroxyurs-12-en-28-oic acid), is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.
Ursolic acid is present in many plants, such as Mirabilis jalapa,as well as in many fruits and herbs used in daily life
-Apples
-Basil and holy basil
-Bilberries
-Cranberries
-Elder flower
-Peppermint
-Rosemary
-Lavender
-Oregano
-Thyme
-Hawthorn
-Prunes
Apple peels contain large quantities of ursolic acid and related compounds
Ursolic Acid helped reduce excess damage to neurons, according to animal studies.
In addition, Ursolic Acid helped rebuild the protective sheaths that cover neurons by suppressing immune cells and activating precursors that mature into myelin-forming cells (called oligodendrocytes). Ursolic Acid ameliorates domoic acid-induced cognitive deficits in some animals. Ursolic acid ameliorates cognitive deficits and reduces oxidative damage in the brain of some aging animals induced by D-galactose. Ursolic acid improves cellular immune system and pancreatic beta cell function in some streptozotocin-induced diabetic organisms fed a high-fat diet.
Ursolic Acid also increased skeletal muscle mass, grip strength and exercise capacity in some animals.
Ursolic Acid can be found in plants used for cosmetic additives.
In other words, this plant-derived substance (Ursolic Acid) is used in cosmetic-derived products.
Ursolic Acid can be used as a starting material for the synthesis of more potent bioactive derivatives such as experimental antitumor agents.
Ursolic Acid is a substance found in a variety of fruits, vegetables, and herbs and has a variety of potential pharmacological activities, including anti-inflammatory, antioxidative, antiviral, serum lipid-lowering, and antineoplastic activities.
Ursolic Acid can promote apoptosis and inhibit cancer cell proliferation through multiple mechanisms.
POTENTIEL BIOCHEMICAL EFFECTS:
A number of potential biochemical effects of ursolic acid have been investigated, but there has been no clinical study demonstrating benefits to human health.
In vitro, ursolic acid inhibits the proliferation of various cancer cell types by inhibiting the STAT3 activation pathway,and may also decrease proliferation of cancer cells and induce apoptosis.
Ursolic acid has also been shown to inhibit JNK expression and IL-2 activation of JURKAT leukemic T Cells leading to the reduction in proliferation and T cell activation.
Ursolic acid is a weak aromatase inhibitor (IC50 = 32 μM), and has been shown to increase the amount of muscle and brown fat and decrease white fat obesity and associated conditions when added to diets fed to mice.
Under physiological concentrations, ursolic acid also induces eryptosis (the apoptosis-like suicidal cell death in defective red blood cells).
Ursolic acid can be found in plants that are used for cosmetics additives.
Ursolic acid can serve as a starting material for synthesis of more potent bioactive derivatives, such as experimental antitumor agents
Ursolic Acid can also regulate mitochondrial function through various pathways.
Ursolic Acid is a pentacyclic triterpenoid substituted with a beta-hydroxy group. Ursolic Acid has a role as a plant metabolite and a geroprotector. Ursolic Acid is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid.
Ursolic Acid is derived from the hydride of an ursa.
Ursolic Acid (UA) is a natural triterpene compound found in a variety of fruits and vegetables.
Ursolic Acid has beneficial effects including Anti-inflammatory, antioxidant, anti-apoptotic and anti-carcinogenic effects.
Ursolic Acid shows these beneficial effects in various tissues and organs.
Ursolic Acid increases the expression levels of adenosine monophosphate-activated protein kinase and irisin in skeletal muscle.
Also, Ursolic Acid can be used as an alternative medicine for the treatment and prevention of cancer, obesity/diabetes, cardiovascular disease, brain disease, liver disease and muscle wasting (sarcopenia).
Ursolic Acid is a pentacyclic triterpenoid found in various fruits,
-vegetables and medicinal herbs
-with a variety of potential pharmacologic activities including anti-inflammatory
-antioxidative
-antiviral
-serum lipid-lowering
-antineoplastic activities.
Upon administration, ursolic acid may promote apoptosis and inhibit cancer cell proliferation through multiple mechanisms.
This may include the regulation of mitochondrial function through various pathways including the ROCK/PTEN and p53 pathways, the suppression of the nuclear factor-kappa B (NF-kB) pathways, and the increase in caspase-3, caspase-8 and caspase-9 activities.
Ursolic acid is a pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3.
Ursolic Acid has a role as a plant metabolite and a geroprotector.
Ursolic Acid is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid.
Ursolic Acid derives from a hydride of an ursane.
Ursolic Acid mediates certain pharmacological processes.
In addition, Ursolic Acid modulates various signaling pathways to prevent the development of chronic diseases.
Ursolic Acid is known as a promising substance as it is seen as a means of reorganizing the body.
Ursolic Acid can increase muscle mass and decrease fat mass and is therefore used in many studies.
PHARMACOLOGY AND BIOCHEMISTRY
Antineoplastic Agents, Phytogenic:
Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.
Cyclooxygenase Inhibitors:
Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.
Anti-Infective Agents:
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection
Mechanism of Action:
Ursolic acid, a pentacyclic triterpene acid, inhibited the invasion of HT1080 human fibrosarcoma cells by reducing the expression of matrix metalloproteinase-9.
Since the chemical structure of ursolic acid is very similar to that of dexamethasone, a synthetic glucocorticoid, whether ursolic acid acts through the glucocorticoid receptor /was investigated/.
The expression of matrix metalloproteinase-9 is thought to be regulated similarly with matrix metalloproteinase-1 and matrix metalloproteinase-3 as containing common 2-O-tetradecanoylphorbol-acetate responsible region, where AP-1 proteins can bind.
Ursolic Acid is a phytochemical found in a wide variety of plants but most commonly known to be in apple peels.
In other words, Ursolic Acid is used in pharmaceutical production as well as in cosmetic products.
Ursolic Acid can reduce fat accumulation and increase muscle mass gain while full.
Ursolic Acid can promote fat burning and preserve muscle mass while fasting.
Ursolic Acid is safe when taken with the diet.
Ursolic Acid is a natural pentacyclic triterpene derived from fruit, herbs and other plants.
Ursolic Acid can act on molecular targets of various signaling pathways.
Ursolic Acid can inhibit the growth of cancer cells and induce cycle stagnation.
Dexamethasone has been studied to repress the 2-O-tetradecanoylphorbol-acetate-induced expression of matrix metalloproteinase-1 and matrix metalloproteinase-3 through a glucocorticoid receptor-mediated manner.
In Northern blot analysis, we found that ursolic acid reduced the expression of matrix metalloproteinase-1 and matrix metalloproteinase-3 induced by 2-O-tetradecanoylphorbol-acetate.
Similarly, ursolic acid down-regulated 2-O-tetradecanoylphorbol-acetate-induction of matrix metalloproteinase-9 gene in the same manner of dexamethasone.
RU486, a potent glucocorticoid receptor antagonist, was used for identifying that ursolic acid-induced down-regulation of matrix metalloproteinase-9 expression is mediated by its binding to glucocorticoid receptor.
The effect of ursolic acid on the matrix metalloproteinase-9 expression was blocked by RU486, suggesting that ursolic acid acts via a glucocorticoid receptor in the regulation of matrix metalloproteinase-9.
Western blot analysis and immunocytochemistry showed that ursolic acid increased glucocorticoid receptor fraction in the nucleus, although it decreased the synthesis of glucocorticoid receptor mRNA.
In addition, ursolic acid did not decrease the expression of c-jun and DNA-binding activity of AP-1 to its cognate sequences.
Taken together ursolic acid may induce the repression of matrix metalloproteinase-9 by stimulating the nuclear translocation of glucocorticoid receptor, and the translocated glucocorticoid receptor probably down-modulating the trans-activating function of AP-1 to 2-O-tetradecanoylphorbol-acetate responsible element of matrix metalloproteinase-9 promoter region.
Ursolic acid is a compound present in many fruits and herbs, such as apple peels, cranberry juices, grape skins, holy basil, rosemary, thyme, oregano, sage, and other herbs.
While preclinical studies suggest it has anti-oxidant and anti-inflammatory actions, no studies in humans have evaluated whether ursolic acid improves cognitive function or brain health.
Ursolic acid is also not absorbed very well by the body.
Ursolic acid ingested through the diet is safe, but long-term safety of ursolic acid supplements has not been tested.
Ursolic Acid can exert anticancer activity.
Nanotechnology has been applied to the pharmacological study of Ursolic Acid.
Ursolic Acid can improve hemoglobin and plasma leptin levels.
In addition, Ursolic Acid inhibits the growth cycle of some foreign cells.
Ursolic Acid has an anabolic effect on muscle mass in humans.
Ursolic Acid has some effects on muscle strength and mass in physically active men consuming a high protein diet
Ursolic Acid is triterpenoid compounds which exist widely in natural plants in the form of free acid or aglycones for triterpenoid saponins.
Ursolic Acid helps preserve the look and feel of the skin.
Ursolic Acid acts as a perfume.
Ursolic Acid can also act as a mask of bad odors.
Ursolic Acid has therapeutic benefits in Skin care.
Ursolic Acid contains anti-inflammatory activity.
Ursolic Acid is also used in cosmetics and some cleaning products, as it has an anti-microbial, anti-bacterial effect.
POTENTIAL BENEFIT:
No clinical studies have tested whether ursolic acid can prevent cognitive decline or dementia.
In various preclinical models of cognitive impairment, ursolic acid treatment improved cognitive functions while reducing oxidative stress, brain inflammation, and cellular stress.
However, these promising preclinical findings have not been confirmed in humans
FOR DEMENTIA PATIENTS:
No human research has examined whether ursolic acid can benefit patients with dementia.
Although some preclinical studies have shown benefits in models carrying biological markers of Alzheimer’s disease, these benefits have not been extended to dementia patients.
SAFETY:
Ursolic acid consumed in the diet is safe.
No large, long-term, randomized controlled clinical trials have tested ursolic acid supplements, and therefore, long-term safety for supplements is unknown.
Drug interactions with ursolic acid are also not known.
Because ursolic acid is not absorbed very well by the body, clinical studies in cancer patients have used a drug delivery vehicle called liposomes, which are spherical lipid vesicles, wherein ursolic acid was packaged.
This special form of ursolic acid has caused some adverse events such as elevated liver enzymes, fever, and abdominal distension
HOW TO USE:
Ursolic acid is available over the counter as a supplement.
Ursolic Acid is also present in food,
-such as apple peel
-cranberry juice
-grape skin
-holy basil
-rosemary
-thyme
-oregano
-sage
-other herbs
Rosemary and sage have the highest content of ursolic acid, 3.0% and 1.8%, respectively.
Apple skin contains 1.4% ursolic acid.
The appropriate dose of ursolic acid has not been determined.
In people with metabolic syndrome, a daily dose of 150 mg was tested in a clinical trial
Ursolic acid is a phytochemical found in a wide variety of plants but most well known for being in apple peels.
Although the science is preliminary, it seems to be able to reduce fat accumulation and increase muscle mass gain when in a fed state, and to induce fat burning and preserve muscle mass when in a fasted state
Ursolic acid found in various fruits, vegetables and medicinal herbs, with a variety of potential pharmacologic activities including anti-inflammatory, antioxidative, antiviral, serum lipid-lowering, and antineoplastic activities.
Upon administration, ursolic acid may promote apoptosis and inhibit cancer cell proliferation through multiple mechanisms.
This may include the regulation of mitochondrial function through various pathways including the ROCK/PTEN and p53 pathways, the suppression of the nuclear factor-kappa B (NF-kB) pathways, and the increase in caspase-3, caspase-8 and caspase-9 activities.
USES OF URSOLIC ACID:
Since Ursolic Acid is a plant-derived substance, it can be used in the manufacture of many products.
Ursolic Acid is used in the production of some cosmetic derivatives.
Ursolic Acid is used for research purposes in laboratories where therapeutic drugs are developed.
Ursolic Acid can be used as a starting material for the synthesis of more potent bioactive derivatives such as experimental antitumor agents.
Ursolic Acid can increase muscle mass and decrease fat mass and is therefore used in many studies.
Ursolic Acid is used in some creams as it helps to preserve the look and feel of the skin.
Ursolic Acid is used in perfumes because it is effective on odor.
Ursolic Acid is also used in the manufacture of odor masking sprays.
Ursolic Acid is also used in the production of skin care products, as it has therapeutic benefits in skin care.
Since Ursolic Acid contains anti-inflammatory activity, it has important areas of use in many areas.
Ursolic Acid is also used in cosmetics and some cleaning products, as it has antimicrobial and antibacterial effects.
Ursolic Acid can be used as a natural fragrance ingredient.
Ursolic Acid is widely used in pharmacological studies.
Ursolic Acid is used as an emulsifying agent in foods.
Since Ursolic Acid is a plant-derived substance, Ursolic Acid can be used in the production of products containing natural fragrance.
In other words, Ursolic Acid is used in pharmaceutical production as well as in cosmetic products.
Ursolic Acid is also widely used in the medical field.
In addition, Ursolic Acid is used in the production of some drugs as it inhibits the growth of harmful cells in the body.
Also, Ursolic Acid can be used as an alternative medicine for the treatment and prevention of cancer, obesity/diabetes, cardiovascular disease, brain disease, liver disease and muscle wasting (sarcopenia)
Ursolic Acid can be used as a starting material for the synthesis of more potent bioactive derivatives such as experimental antitumor agents
APPLICATIONS OF URSOLIC ACID:
-Production of cosmetics
-Production of plant-derived creams
-Synthesis of experimental antitumor agents
-Bioactive substance production
-Fragrance-spray industry
-Diet pills
-Making muscle drugs
-Fat burning ingredients
-Dermatological studies
-Perfumery
-Production of skin care products
-Products containing anti-inflammatory activity.
-Production of antibacterial cleaning products
-Food industry
-In emulsifying agents
-Research laboratories
Ursolic acid (UA) is a natural pentacyclic triterpene derived from fruit, herb, and other plants.
Ursolic Acid can act on molecular targets of various signaling pathways, inhibit the growth of cancer cells, promote cycle stagnation, and induce apoptosis, thereby exerting anticancer activity.
However, its poor water-solubility, low intestinal mucosal absorption, and low bioavailability restrict its clinical application.
In order to overcome these deficiencies, nanotechnology, has been applied to the pharmacological study of UA.
The improvement of the antitumor ability of the UA nanoformulations is mainly due to the improvement of the bioavailability and the enhancement of the targeting ability of the UA molecules.
Ursolic Acid nanoformulations can even be combined with computational imaging technology for monitoring or diagnosis.
Currently, a variety of Ursolic Acid nanoformulations, such as micelles, liposomes, and nanoparticles, which can increase the solubility and bioactivity of UA, while promoting the accumulation of UA in tumor tissues, have been prepared.
Although the research of Ursolic Acid in the nanofield has made great progress, there is still a long way to go before the clinical application of UA nanoformulations.
Ursolic acid is a plant‑derived pentacyclic triterpenoid found in various medicinal herbs and fruits.
Ursolic Acid has generated clinical interest due to its anti‑inflammatory, antioxidative, antiapoptotic and anticarcinogenic effects.
An increasing amount of evidence supports the anticancer effect of ursolic acid in various cancer cells.
PHYSICAL PROPERTIES OF URSOLIC ACID:
Molecular Weight: 456.7
Exact Mass: 456.36034539
Physical Description: Solid
Color/Form: Platelets from alcohol
Melting Point: 284 °C
Solubility: 1.02X10-4 mg/L in water
Vapor Pressure: 3.49X10-14 mmHg
Density: 304.7 g/mL
Storage Temperature: 2-8°C
Form: Crystalline Powder or Needles
Color: White to off-white
CHEMICAL PROPERTIES OF URSOLIC ACID:
XLogP3-AA: 7.3
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 1
Topological Polar Surface Area: 57.5 Ų
Heavy Atom Count: 33
Formal Charge: 0
Complexity: 874
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 10
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
LogP: log Kow = 7.92
Henrys Law Constant: 9.66X10-10 atm-cu m/mol
Optical Rotation: +67.5 deg
Flash Point: 304.7 °C
One of the hallmarks of malignant transformation is metabolic reprogramming that sustains macromolecule synthesis, bioenergetic demand and tumor cell survival.
Mitochondria are important regulators of tumorigenes is as well as a major site of the metabolic reactions that facilitate this reprogramming and adaption to cellular and environmental changes.
The current review explored the close association between the anticancer effect of ursolic acid and the activation of mitochondrial‑dependent signaling pathways
Ursolic acid (UA) is a pentacyclic triterpene which is found in common herbs and medicinal plants that are reputed for a variety of pharmacological effects.
Both as an active principle of these plants and as a nutraceutical ingredient, the pharmacology of UA in the CNS and other organs and systems has been extensively reported in recent years.
In this communication, the antioxidant and anti-inflammatory axis of UA’s pharmacology is appraised for its therapeutic potential in some common CNS disorders.
Classic examples include the traumatic brain injury (TBI), cerebral ischemia, cognition deficit, anxiety, and depression.
STORAGE OF URSOLIC ACID:
Ursolic Acid can be stored for long periods at low temperatures.
Ursolic Acid should normally be stored at +2°C between +8°C.
Ursolic Acid should be stored without exposure to UV rays.
The aqueous solution of Ursolic Acid can be stored and stored for more than one day.
Ursolic Acid does not have very specific bad states, so it has little storage condition.
Ursolic Acid should be stored in a hygienic environment.
Ursolic Acid should be stored away from foodstuffs.
The Ursolic Acid bottle must be tightly closed.
Ursolic Acid should be stored separately from incompatible chemicals.
Ursolic Acid should be stored in a place with a simple ventilation system.
Ursolic Acid should be stored in glass bottles.
Ursolic Acid should be stored in an environment where the temperature level is not too high.
Ursolic Acid should be stored before it reaches its flash point.
SYNONYMS:
Prunol
Malol
Urson
3beta-Hydroxyurs-12-en-28-oic acid
(3beta)-3-Hydroxyurs-12-en-28-oic acid
3beta-Hydroxy-12-ursen-28-ic acid
ursolic-acid
beta.-Ursolic acid
(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Urs-12-en-28-oic acid, 3-hydroxy-, (3beta)-
N-Ethylhydroxylaminehydrochloride
3beta-Hydroxyurs-12-en-28-oate
(1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
3beta-hydroxy-Urs-12-en-28-oate
Hydroxy-12-ursen-28-ic acid
3beta-Hydroxy-12-ursen-28-oic Acid
(3beta)-3-Hydroxyurs-12-en-28-oate
3beta-hydroxy-Urs-12-en-28-oic acid
(3beta)-3-hydroxy-Urs-12-en-28-oate
3.beta.-hydroxy-Urs-12-en-28-oic acid
(3beta)-3-hydroxy-Urs-12-en-28-oic acid
(2S,5S,9S,10S,18S,1R,8R,14R,15R,20R)-18-hydroxy-1,2,8,9,15,19,19-heptamethylpe ntacyclo[12.8.0.0<2,11>.0<5,10>.0<15,20>]docos-11-ene-5-carboxylic acid
