Synthesis of novel oleanolic acid and ursolic acid in C-28 position derivatives as potential anticancer agents

Tian, Tian; Liu, Xinyu; Lee, Eung-Seok; Sun, Jingyang; Feng, Zhonghua; Zhao, Longxuan; Zhao, Chunhui

doi:10.1007/s12272-016-0868-8

Cited by 37 publications

(27 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…They further dissolved the intermediate in dichloromethane to give a series of amino compounds including aminobenzene, p-fluoroaniline, p-chloroaniline, p-bromobenzenamine, p-methoxylaniline o-fluoroaniline, o-chloroaniline and o-bromobenzenamine through condensation in the presence of triethylamine. After this, saponification analogues (62-69) were produced, which were later hydrolysed to give more derivatives (70)(71)(72)(73)(74)(75)(76)(77). Lastly, the 3-oxo anlogue (78) was developed through oxidation with pyridinium chlorochromate.…”

Section: Chemistry Of Uamentioning

confidence: 99%

“…Many researchers, in search of more bioactive compounds, have reported different UA derivatives. Herewith are some of UA analogues with interesting mechanisms related to currently existing non-communicable diseases utilizing positions C-2, C-3, C-20 and C-28 ( Figure 11) [69][70][71][72][73]. One UA derivative compound, 118 (2α,3β,7β,23-tetrahydroxyurs-12-ene-28-oic acid) ( Figure 11), is a naturally occurring compound isolated from Castanea crenata Sieb.…”

Section: Chemistry Of Uamentioning

confidence: 99%

“…Therefore, it is necessary to construct its derivatives through semi-synthetic modifications in order to improve its antitumor activity. Mostly, the modifications of ursolic acid occur at sites C-3, C12-C13, and at position C-28 [59,63,64,72]. Jiménez-Arellanes and colleagues (2013) reported antimicrobial activity of pentacyclic triterpenoid compounds, namely, UA against Mycobacterium tuberculosis H37Rv [85].…”

Section: Sources Of Ua and Its Biological Potencymentioning

confidence: 99%

See 2 more Smart Citations

Ursolic Acid and Its Derivatives as Bioactive Agents

et al. 2019

View full text Add to dashboard Cite

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.

show abstract

Section: Chemistry Of Uamentioning

confidence: 99%

Section: Chemistry Of Uamentioning

confidence: 99%

Section: Sources Of Ua and Its Biological Potencymentioning

confidence: 99%

See 1 more Smart Citation

Ursolic Acid and Its Derivatives as Bioactive Agents

et al. 2019

View full text Add to dashboard Cite

show abstract

“…One of these semi-synthetic products, 3β-acetoxyursolic acid [1-(2-aminoethylamino)-1-oxo] ethyl ester (14) (▶ Fig. 3), was found to exhibit discernible cytotoxicity, showing an IC 50 value in the range 8-10 µM, while, the IC 50 values of (+)-ursolic acid (11) were greater than 100 µM for all these 3 cancer cell lines used [58].…”

Section: Ursane-type Triterpenoidsmentioning

confidence: 99%

Natural Product Triterpenoids and Their Semi-Synthetic Derivatives with Potential Anticancer Activity

Ren

Kinghorn

2019

Planta Med

View full text Add to dashboard Cite

Triterpenoids are distributed widely in higher plants and are of interest because of their structural diversity and broad range of bioactivities. In particular, there is a very large literature on the propensity of a variety of triterpenoids to act as potential anticancer agents. In the present review, the anticancer potential is summarized for naturally occurring triterpenoids and their semi-synthetic derivatives, including examples of lupane-, oleanane-, ursane-, and cucurbitane-type pentacyclic triterpenoids, along with dammarane-type tetracyclic triterpenes including ginsenosides and their sapogenins and dichapetalins, which have been characterized as antitumor leads from higher plants. Preliminary structure-activity relationships and reported mechanisms of the antineoplastic-related activity are included. Prior studies for triterpenoids of plant origin are supportive of additional work being conducted on the more detailed biological and mechanistic evaluation for the progression of this type of natural products as possible cancer chemotherapeutic agents.

show abstract

“…Ursolic acid (UA) is a pentacyclic triterpene, which is widely distributed throughout the whole plant kingdom, and is a major component of some traditional medicinal plants [13]. It has been found to have anti-cancer and anti-hyperlipidemia effects [14][15][16]. In our previous study, we reported the synergistic effects of artesunate and ursolic acid on lipid reduction and anti-atherosclerosis [17].…”

Section: Introductionmentioning

confidence: 99%

The Metabolic Changes of Artesunate and Ursolic Acid on Syrian Golden Hamsters Fed with the High-Fat Diet

Liu

Shan

et al. 2020

Molecules

View full text Add to dashboard Cite

Artesunate was well known as an antimalarial drug. Our previous research found that it has hypolipidemia effects in rabbits fed with a high-fat diet, especially combined with ursolic acid. In this study, we reconfirmed the lipid-lowering effect of artesunate and ursolic acid in hamsters and analyzed the metabolic changes using gas chromatography time-of-flight mass spectrometry (GC/TOF MS). Compared with the model group, a variety of different metabolites of artesunate and ursolic acid, alone or in combination, were found and confirmed. These differential metabolites, including fatty acids, lipids, and amino acids, were involved in lipid metabolism, energy metabolism, and amino acid metabolism. It indicated that two agents of artesunate and ursolic acid could attenuate or normalize the metabolic transformation on these metabolic pathways.

show abstract

Synthesis of novel oleanolic acid and ursolic acid in C-28 position derivatives as potential anticancer agents

Cited by 37 publications

References 25 publications

Ursolic Acid and Its Derivatives as Bioactive Agents

Ursolic Acid and Its Derivatives as Bioactive Agents

Natural Product Triterpenoids and Their Semi-Synthetic Derivatives with Potential Anticancer Activity

The Metabolic Changes of Artesunate and Ursolic Acid on Syrian Golden Hamsters Fed with the High-Fat Diet

Contact Info

Product

Resources

About