Characteristics, Biological Properties and Analytical Methods of Ursolic Acid: A Review

Pironi, Andressa Maria; Araújo, Patricia Rocha de; Fernandes, Mariza Aires; Salgado, Hérida Regina Nunes; Chorilli, Marlus

doi:10.1080/10408347.2017.1390425

Cited by 37 publications

(35 citation statements)

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“…Ursolic acid (3 β-hydroxy-urs-12-en-28-oic acid) is a pentacyclic triterpenoid composed of a C-30 chemical structure built from isoprenoid units with A, B, C, D and E rings ( Figure 1) [51]. UA may occur as an aglycone or free acid of saponins [52,53].…”

Section: Chemistry Of Uamentioning

confidence: 99%

“…The biosynthesis of UA found in plant cells originates from the cyclical (3S)-oxidosqualene cycling. The predominant (3S)-oxidosqualene predecessor is converted into a cationic dammarenyl structure undergoing chain growth and other cyclic changes in order to form this third distinct ring, which is present in the α-amyrin skeleton, a nucleus in the UA [51]. It is well known that low aqueous solubility of a drug may seriously affect its medication effectiveness.…”

Section: Chemistry Of Uamentioning

confidence: 99%

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Ursolic Acid and Its Derivatives as Bioactive Agents

et al. 2019

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Non-communicable diseases (NCDs) such as cancer, diabetes, and chronic respiratory and cardiovascular diseases continue to be threatening and deadly to human kind. Resistance to and side effects of known drugs for treatment further increase the threat, while at the same time leaving scientists to search for alternative sources from nature, especially from plants. Pentacyclic triterpenoids (PT) from medicinal plants have been identified as one class of secondary metabolites that could play a critical role in the treatment and management of several NCDs. One of such PT is ursolic acid (UA, 3 β-hydroxy-urs-12-en-28-oic acid), which possesses important biological effects, including anti-inflammatory, anticancer, antidiabetic, antioxidant and antibacterial effects, but its bioavailability and solubility limits its clinical application. Mimusops caffra, Ilex paraguarieni, and Glechoma hederacea, have been reported as major sources of UA. The chemistry of UA has been studied extensively based on the literature, with modifications mostly having been made at positions C-3 (hydroxyl), C12-C13 (double bonds) and C-28 (carboxylic acid), leading to several UA derivatives (esters, amides, oxadiazole quinolone, etc.) with enhanced potency, bioavailability and water solubility. This article comprehensively reviews the information that has become available over the last decade with respect to the sources, chemistry, biological potency and clinical trials of UA and its derivatives as potential therapeutic agents, with a focus on addressing NCDs.

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Section: Chemistry Of Uamentioning

confidence: 99%

Section: Chemistry Of Uamentioning

confidence: 99%

Ursolic Acid and Its Derivatives as Bioactive Agents

et al. 2019

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“…Because it is one of the most common biologically active ingredients in plants, it has received wide attention. UA has a wide range of biological activities including anti‐microbial, anti‐inflammatory and anti‐allergic reactions, anti‐tumor, promote hair growth, melanocyte proliferation and melanin biosynthesis, protect heart, anti‐diabetes, improving blood lipids, anti‐obesity, anti‐atherosclerosis, anti‐hepatic steatosis and fibrosis, analgesic, anti‐anxiety, anti‐depression, improve learning and memory and other neuroprotective effects, anti‐muscle atrophy, anti‐fatigue and anti‐osteoporosis and other pharmacological effects . However, UA is almost insoluble in water and its bioavailability is poor.…”

Section: Introductionmentioning

confidence: 99%

Ursolic acid: Pharmacokinetics process in vitro and in vivo, a mini review

Wen

2019

Archiv der Pharmazie

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Ursolic acid (UA) is a natural triterpene compound found in various fruits and vegetables. UA has a widespread pharmacologic effect, including antitumor, anti‐inflammatory, anti‐oxidant, anti‐apoptotic, anti‐allergy, and anti‐carcinogenic effects. UA can be used as an alternative medicine for the treatment and prevention of many diseases. However, the bioavailability of UA by oral administration is low since it is absorbed by the intestine through passive diffusion. Therefore, some novel technologies are used to produce UA preparations that can change the pharmacokinetics process and increase its solubility and bioavailability. At present, pharmacokinetic studies on UA are few. In this paper, we will review the pharmacokinetics features of free UA and some novel UA preparations in vitro and in vivo, in order to provide a reference for rational utilization and drug design of UA.

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“…UA is derived from diverse plants and fruits, such as rosemary (Rosmarinus officinalis), apple (Malus domestica), makino, cranberries (Vaccinium macrocarpon), pears (Pyrus pyrifolia), prunes (Prunus domestica), bearberries (Arctostaphylos alpina), loquat (Eriobotrya japonica), scotch heather (Calluna vulgaris), basil (Ocimum sanctum), and jamun (Eugenia jambolana) [9,11]. UA posed different activity against BrC via several molecular mechanisms [7,11,[33][34][35], and UA is relatively nontoxic to normal cells [11]. Administration of UA demonstrates inhibitory efficacy against cell proliferation rate and induces apoptosis via both the mitochondrial death pathway (cleavage of caspase-9, caspase-3, and PARP, Bax upregulation and Bcl-2 downregulation, release of cytochrome c to the cytosol, decreased mitochondrial membrane potential) and extrinsic death receptordependent pathway (Fas receptor) in MDA-MB-231 cells [9,11].…”

Section: Ursolic Acidmentioning

confidence: 99%

“…The treatment of BrC cells with UA induced changes in glycolytic pathway leading to cytotoxic autophagy, also at low doses (5-20 μm) caused a G0/G1 cell cycle arrest, increased p21 levels, oxidative stress, and DNA damage [36]. UA has been demonstrated to exhibit strong anti-BrC potential by inducing cell cycle arrest and inhibition of proliferation, angiogenesis, and metastasis in both in vitro and in vivo models [7,11,[33][34][35]. Finally, UA inhibited BrC growth by inducing cell death via the inhibition of inflammatory responses through the NF-κB, PI3K/AKT signaling pathways [9,33].…”

Section: Ursolic Acidmentioning

confidence: 99%

Cytotoxic Effect and Mechanisms from Some Plant-Derived Compounds in Breast Cancer

Pérez-Soto¹,

Estanislao-Gómez²,

Pérez-Ishiwara³

et al. 2019

Cytotoxicity - Definition, Identification, and Cytotoxic Compounds

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Breast cancer (BrC) is a major health problem in women all around the world. A growing knowledge about these alterations and their associated molecular signaling pathways offers opportunities for therapeutic strategies; chemotherapy is one of the most utilized treatments; however, because of the adverse side effects and multidrug resistance that patients may present, there has been great advancement in search of new alternatives as the use of plant-derived natural compounds. This review describes information on the progress and development of cytotoxic compounds against BrC belonging to the families of flavonoids, terpenes, and alkaloids that through in vitro and in vivo studies have demonstrated to induce cellular death mainly through apoptosis, activating the intrinsic pathway. The in vitro IC 50 and the in vivo EC 50 dose-response relationship can vary depending on various factors, including the choice of cell line and/or the model used. Also, the association of some of these compounds with nanoparticles or paclitaxel with antibodies has clearly shown a potential improvement in its effect. The clinical studies that are being conducted with some of them show promising results; however, it is necessary to continue with the effort to develop new and more effective drugs against different types of BrC.Cytotoxic Effect and Mechanisms from Some In vivo models for studying plant-derived compounds in breast cancerWide varieties of animal model systems are now available to investigate plantderived compounds in different stages, such as cancer initiation, promotion progression, invasion, and metastasis. These models are also used to comprehend therapeutic response, which represents an essential step between in vitro systems and clinical studies [8,13]. The in vivo models are also used to investigate the capability of plant formulation to induce an anti-BrC effect where it is sought to optimize dose, bioavailability, administration routes, and selective delivery and reduce toxic effects, among others [8,14]. The two animal species that will be mentioned in this review are those involving mice and rats [14]; however, BrC mouse models are used in a variety of preclinical studies [13].There are different types of in vivo models of BrC, such as cell line-derived xenografts (MDA-MB-231 line) that are implanted into immunocompromised animals (cell-derived xenografts, CDX). CDX models represent a relatively homogenous mass of transformed breast epithelial cells, and depending on where the cells are inoculated, they are classified as ectopic CDX (models advanced disease only, subcutaneous injection of human tumor cells), orthotopic CDX (in mammary gland/fat pad), metastatic CDX (following tail vein or intra-cardiac injection in specific sites, i.e., bone or lung), syngeneic (mouse tissue implanted to strainmatched host) or metastasis with syngeneic model (usually fast-growing tumors and microenvironment derive from the same species, i.e., 4T1 cells), and genetically engineered mouse models (GEMMs) to address early events of tu...

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Characteristics, Biological Properties and Analytical Methods of Ursolic Acid: A Review

Cited by 37 publications

References 73 publications

Ursolic Acid and Its Derivatives as Bioactive Agents

Ursolic Acid and Its Derivatives as Bioactive Agents

Ursolic acid: Pharmacokinetics process in vitro and in vivo, a mini review

Cytotoxic Effect and Mechanisms from Some Plant-Derived Compounds in Breast Cancer

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