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Ursolic Acid — Food Sources, Benefits, Side Effects and Supplement

Article author photo Ani Harutyunyan Ani Harutyunyan | Обновлено: Июль 29, 2024
Проверено Elen Khachatrian Article author photo Elen Khachatrian

Ursolic Acid Food Sources,
 

Summary

Ursolic acid, a pentacyclic triterpenoid, consists of five interconnected six-membered carbon rings featuring a hydroxyl group at C-3 and a carboxylic acid group at C-17. It is metabolized in the liver, undergoing phase I and II processes, leading to its excretion via bile or urine

Supplements of ursolic acid are available in various forms, with doses typically ranging from 150 mg to 450 mg daily, though consulting a healthcare provider is recommended. Rich natural sources include apple peels, rosemary, and holy basil

Ursolic acid offers numerous health benefits, such as anticancer, antidiabetic, cardiovascular, brain health, muscle health, and allergy-modulating effects. However, it can interact with medications metabolized by liver enzymes, potentially altering their effects.

Introduction

Ursolic acid is a naturally occurring compound found in a variety of plants, most notably in the peels of apples, as well as in rosemarythyme, and other herbs. The several possible health benefits of this pentacyclic triterpenoid have attracted a lot of interest in recent years. Studies reveal that ursolic acid is an intriguing option for medicinal purposes due to its antioxidantanti-inflammatory, and anti-tumor characteristics. Its potential to support muscular growthprevent fat from accumulating, and improve general metabolic health has also been researched. Due to its status as a bioactive phytochemical, ursolic acid is still being thoroughly studied by scientists, who see it as a possible natural treatment for a number of health issues.

Ursolic Acid Structure and Metabolism 

Ursolic acid's structure, a pentacyclic triterpenoid molecule, is characterized by five interconnected six-membered carbon rings. This compound, with the chemical formula C30H48O3, features a hydroxyl group at position C-3 and a carboxylic acid group at position C-17. These functional groups, along with their rigid, multi-ringed structure, which is typical for triterpenoids, play a crucial role in their biological activity (1). The exact atomic configuration of ursolic acid creates a durable scaffold that interacts with a range of biological targets, influencing cellular functions such as metabolism, apoptosis, and inflammation. 

The metabolism of ursolic acid in the human body involves several phases, primarily occurring in the liverCytochrome P450 enzymes metabolize ursolic acid through phase I metabolic processes, which include oxidationreduction, and hydrolysis. Ursolic acid undergoes reactions to produce more polar metabolites, which make digestion easier. These metabolites then go through conjugation processes, like glucuronidation and conjugation with glutathione, in phase II metabolism, which improve their solubility and encourage excretion (2). Following that, these conjugated metabolites are either sent to the bile for excretion in the stools or to the kidneys for elimination in the urine (3). The metabolic changes that ursolic acid undergoes can affect its bioavailability and biological effects because they alter the compound's stability, activity, and interactions with different molecular targets in the body.

Ursolic Acid Supplements and Recommended Intake

Ursolic acid supplements are available in various forms to accommodate different preferences and needs. 

Capsules and tablets are the most common, offering convenient and measured doses that can be easily taken with water. Powders provide flexibility in dosage adjustment and can be mixed into beverages or food. Liquid extracts offer another option, potentially enhancing absorption for quicker effects. Additionally, natural sources like apple peelsrosemary, and holy basil can provide ursolic acid through dietary means. 

The recommended intake of ursolic acid is not firmly established due to the lack of standardized guidelines and varying results from different studies. However, typical supplemental doses range from 150 mg to 450 mg per day (4). It's essential to start with a lower dose to assess individual tolerance and gradually increase it if needed. Given the potential for interactions with medications and the risk of adverse effects, it is highly recommended to consult with a healthcare provider before starting ursolic acid supplements. 

Foods Sources of Ursolic Acid

Apples, particularly their peels, are one of the richest sources of ursolic acid. Other significant sources include medicinal herbs such as rosemary, thyme, and basil, berries like cranberries and blueberries, and certain fruits, such as plums and prunes, which also contain ursolic acid. Additionally, the peels of pears and cherries are known to contain appreciable amounts (5) (6) (7) (8).

FoodUrsolic Acid Content /mg per 100g/Recommended Serving Size
Raisin791 oz /28.35g/
Cranberry661 cup /110g/
Apple 40-60 1 cup /125g/
Basil36-725 leaves /2.5g/
Rosemary7.31 tbsp /1.7g/
Green Tea0.47-0.551 cup /260g/
Thyme0.43-0.540.5 tsp /0.4g/

Health Benefits

Anticancer Effects

Numerous fruits and herbs naturally contain ursolic acid, a triterpenoid shown to have strong anti-cancer effects by various pathways. One of the main mechanisms is the induction of apoptosis, in which ursolic acid causes cancer cells to undergo programmed cell death by activating both intrinsic and extrinsic pathways (9). Furthermore, it prevents cancer cell proliferation by influencing important signaling pathways that are essential for cell development and survival, like PI3K/Akt and MAPK (10). Additionally, ursolic acid has anti-angiogenic qualities that limit the growth and metastasis of tumors by preventing the development of new blood vessels (11). Moreover, it has been demonstrated to inhibit the function of matrix metalloproteinases (MMPs), which are enzymes that promote the invasion and metastasis of cancer cells (12). 

The effectiveness of ursolic acid as an anticancer drug has been demonstrated across a range of cancer types. Studies show that it works especially well against breast cancer, where it causes apoptosis and suppresses cell growth (13). Because ursolic acid promotes an anti-inflammatory response and has anti-angiogenic characteristics, it inhibits the growth of tumors and decreases metastasis in colorectal cancer (14). In addition, it significantly reduces the risk of prostate cancer by causing cell cycle arrest and modifying androgen receptor signaling (15). Additionally, research has demonstrated that by promoting apoptosis and preventing angiogenesis, ursolic acid can effectively stop the growth of liver cancer cells. Its ability to block cell migration and invasion in lung cancer highlights its potential to stop metastasis (16). 

Antidiabetic Effects

A major mechanism via which ursolic acid reduces diabetes is by improving insulin sensitivity and lowering glucose tolerance(17). It increases the absorption of blood glucose by muscles and decreases the production of gluconeogenesis in the liver by activating AMP-activated protein kinase (AMPK), an essential energy sensor (18). Furthermore, ursolic acid increases the amount of glucose that cells absorb by modulating the expression of glucose transporters, especially GLUT4 (19). 

Cardiovascular Health 

Studies show that ursolic acid protects the cardiovascular system in a number of ways. It exhibits antioxidant and anti-inflammatory qualities that help reduce the oxidative stress and inflammation that are frequently linked to heart disease.

 By raising HDL cholesterol and lowering LDL and triglyceride levels, ursolic acid also helps to enhance lipid profiles (20). Furthermore, studies have demonstrated that it can improve endothelial function and suppress platelet aggregation, which can improve vascular health and lower the risk of thrombosis and atherosclerosis (21). 

Brain Health

According to research, ursolic acid has neuroprotective qualities that may lessen the impacts of neurodegenerative diseases, including Parkinson's and Alzheimer's. It has antioxidant and anti-inflammatory properties that lessen inflammation and oxidative stress in the brain, two important processes in the development of many illnesses (22). Furthermore, it has been demonstrated that ursolic acid stimulates the development and differentiation of brain cells, improving memory and cognitive abilities (23). Its capacity to pass through the blood-brain barrier increases its therapeutic potential and positions it as a strong contender for the development of drugs meant to maintain brain function and stave off cognitive decline.

Muscle Health and Exercise Performance

Ursolic acid has shown promising effects in combating sarcopenia - age-related muscle atrophy and loss of strength of skeletal muscles. Studies show that ursolic acid can promote the growth of muscle mass and performance in a number of ways. It promotes the synthesis of muscle proteins in part via triggering the mTOR signaling pathway, which is essential for the development and maintenance of muscle cells (24). Furthermore, ursolic acid has anti-inflammatory qualities that lessen chronic inflammation, which in turn helps older people's muscles deteriorate. Additionally, it aids in enhancing mitochondrial function via stabilizing the mitochondrial membrane, which lessens tiredness and increases muscle endurance (25). Because of these combined benefits, ursolic acid may be used as a medicinal medication to prevent or lessen the symptoms of sarcopenia, encouraging older people to age more healthfully and live better.

Studies suggest that ursolic acid may improve muscle strength and endurance by promoting muscle growth (26). It works by increasing the activity of insulin-like growth factor-1 (IGF-1) and muscle-specific proteins, which are crucial for muscle repair and growth.

Allergy

Ursolic acid has shown promise in modulating allergic responses, owing to its anti-inflammatory and immunomodulatory properties. Research suggests that ursolic acid can inhibit the release of histamine, a key mediator in allergic reactions, from mast cells and basophils (27). By suppressing the activity of these cells, ursolic acid may reduce symptoms such as itchingswelling, and redness associated with allergic reactions. Additionally, its ability to downregulate pro-inflammatory cytokines and oxidative stress further contributes to alleviating allergic responses. These effects make ursolic acid a potential natural compound for managing allergies, particularly those related to seasonal changes or chronic inflammatory conditions (28). However, while preliminary findings in mice are encouraging, more extensive clinical trials are needed to confirm the efficacy and safety of ursolic acid in allergy management.

Ursolic Acid Side Effects

Drug Interactions

Ursolic acid can potentially interact with various medications, leading to altered effects or increased risk of side effects. Its effects on liver enzymes may have an impact on the metabolism of pharmaceuticals that are metabolized by the liver, including anti-seizure drugsstatins, and some antidepressants (29).

 This could result in an increase in their toxicity or a decrease in their effectiveness. Moreover, the potential impact of its antioxidant properties on the activity of chemotherapy medicines may improve their efficacy (30). 

References

  1. https://pubchem.ncbi.nlm.nih.gov/compound/Ursolic-Acid 
  2. https://pubs.rsc.org/en/content/articlelanding/2018/ra/c7ra11856b 
  3. https://www.frontiersin.org/journals/pharmacology/articles/10.3389/fphar.2021.706121/full 
  4. https://examine.com/supplements/ursolic-acid/#research-breakdown 
  5. https://www.researchgate.net/figure/Changes-in-amount-of-ursolic-acid-in-the-whole-apple-samples-before-and-after-storage-in_fig3_352404034 
  6. https://www.mdpi.com/1420-3049/13/10/2482 
  7. https://www.researchgate.net/publication/270066124_Oleanolic_Acid_and_Ursolic_Acid_in_Commercial_Dried_Fruits 
  8. https://dergipark.org.tr/en/download/article-file/1746507 
  9. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6506288/ 
  10. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7460570/ 
  11. https://link.springer.com/article/10.1007/s00253-016-7360-8 
  12. https://www.sciencedirect.com/science/article/abs/pii/S0009279719317739 
  13. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8457520/ 
  14. https://www.mdpi.com/1661-3821/4/3/22 
  15. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10138876/ 
  16. https://www.sciencedirect.com/science/article/abs/pii/S1043661822002511 
  17. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8561770/ 
  18. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8621142/ 
  19. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4203820/ 
  20. https://www.mdpi.com/1420-3049/25/6/1392 
  21. https://www.phytojournal.com/vol1Issue6/Issue_march_2013/14.pd 
  22. https://pubmed.ncbi.nlm.nih.gov/29098660/ 
  23. https://www.sciencedirect.com/science/article/abs/pii/S1567576923005799 
  24. https://www.mdpi.com/2073-4409/12/19/2422 
  25. https://www.mdpi.com/2072-6643/15/4/1049 
  26. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379974/ 
  27. https://pubmed.ncbi.nlm.nih.gov/34435583/ 
  28. https://pubmed.ncbi.nlm.nih.gov/32208746/ 
  29. https://pubmed.ncbi.nlm.nih.gov/15043991/
  30. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8714329/ 
Article author photo Ani Harutyunyan
Специальность: General Medicine at YSMU
Обновлено: Июль 29, 2024
Проверено Elen Khachatrian
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