scholarly journals Synthesis and antitumor activity of fluorouracil – oleanolic acid/ursolic acid/glycyrrhetinic acid conjugates

MedChemComm ◽  
2019 ◽  
Vol 10 (8) ◽  
pp. 1370-1378 ◽  
Author(s):  
Chun-Mei Liu ◽  
Jia-Yan Huang ◽  
Li-Xin Sheng ◽  
Xiao-An Wen ◽  
Ke-Guang Cheng
Keyword(s):  
Antitumor Activity ◽  
Adverse Effects ◽  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Biological Activities ◽  
Glycyrrhetinic Acid ◽  
Antitumor Activities ◽  
Pentacyclic Triterpene ◽  
Pentacyclic Triterpenes

Due to the obvious adverse effects of 5-fluorouracil and considering the diverse biological activities of pentacyclic triterpenes, twelve pentacyclic triterpene-5-fluorouracil conjugates were synthesized and their antitumor activities were evaluated.

Synthesis of oleanolic acid/ursolic acid/glycyrrhetinic acid-hydrogen sulfide donor hybrids and their antitumor activity

2019 ◽  
Vol 28 (8) ◽  
pp. 1212-1222 ◽  
Author(s):  
Li-xin Sheng ◽  
Jia-yan Huang ◽  
Chun-mei Liu ◽  
Ju-zheng Zhang ◽  
Ke-guang Cheng
Keyword(s):  
Hydrogen Sulfide ◽  
Antitumor Activity ◽  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Glycyrrhetinic Acid

scholarly journals Synthesis of Lapachol-Based Glycosides and Glycosyl Triazoles with Antiproliferative Activity Against Several Cancer Cell Lines

2021 ◽  
Author(s):  
Flaviano Melo Ottoni ◽  
Lucas Bonfim Marques ◽  
Juliana Martins Ribeiro ◽  
Lucas Lopardi Franco ◽  
José Dias Souza Filho ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Adverse Effects ◽  
Dna Fragmentation ◽  
Cell Lines ◽  
Cancer Cell ◽  
Antiproliferative Activity ◽  
Biological Activities ◽  
Cancer Cell Lines ◽  
Tumor Cell Lines

Abstract Lapachol (1), a natural naphthoquinone, presents several biological activities including antitumor activity, used as anticancer coadjuvant whose use was abandoned because of adverse effects. Herein, we reported the synthesis and cytotoxicity evaluation against cancer cell lines of a series of Oglycosides and glycosyl triazoles derived from lapachol. In addition to the determination of IC50, the DNA fragmentation and clonogenicity were also evaluated. The glycoside derived from D-glucose (5) was far more active than lapachol (1) and more active in tumor cell lines HL60, Jurkat, THP-1 and MDA-MB-231 than to the non-tumoral PBMC cell line, indicating an improvement in activity and selectivity as compared with lapachol (1). Compound 5 and the glycosides derived from D-galactose (14), D-N-acetylglucosamine (15) and L-fucose (16) showed good results in the DNA fragmentation and clonogenicity assays in the studies of subdiploid DNA content, indicating a pro-apoptotic potential and a good antiproliferative activity of these glycosides.

scholarly journals Preparative separation of structural isomeric pentacyclic triterpene oleanolic acid and ursolic acid from natural products by pH-zone-refining countercurrent chromatography

RSC Advances ◽  
2019 ◽  
Vol 9 (66) ◽  
pp. 38860-38866
Author(s):  
Chaoyue Wang ◽  
Xiang Wang ◽  
Shanshan Zhao ◽  
Wenyu Sun ◽  
Shengqiang Tong
Keyword(s):  
Natural Products ◽  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Eriobotrya Japonica ◽  
Countercurrent Chromatography ◽  
Zone Refining ◽  
Preparative Separation ◽  
Pentacyclic Triterpene ◽  
Apple Peels

pH-zone-refining countercurrent chromatography was investigated in preparative separation of oleanolic acid and ursolic acid from three different natural products, Aralia chinensis, apple peels and Eriobotrya japonica Thunb.

scholarly journals Anti-Planktonic and Anti-Biofilm Properties of Pentacyclic Triterpenes—Asiatic Acid and Ursolic Acid as Promising Antibacterial Future Pharmaceuticals

Biomolecules ◽  
2022 ◽  
Vol 12 (1) ◽  
pp. 98
Author(s):  
Zuzanna Sycz ◽  
Dorota Tichaczek-Goska ◽  
Dorota Wojnicz
Keyword(s):  
Ursolic Acid ◽  
Pathogenic Bacteria ◽  
Biological Activities ◽  
Multidrug Resistant ◽  
Resistant Bacteria ◽  
Asiatic Acid ◽  
Pentacyclic Triterpenes ◽  
Planktonic Form ◽  
Medicinal Properties ◽  
Biofilm Structure

Due to the ever-increasing number of multidrug-resistant bacteria, research concerning plant-derived compounds with antimicrobial mechanisms of action has been conducted. Pentacyclic triterpenes, which have a broad spectrum of medicinal properties, are one of such groups. Asiatic acid (AA) and ursolic acid (UA), which belong to this group, exhibit diverse biological activities that include antioxidant, anti-inflammatory, diuretic, and immunostimulatory. Some of these articles usually contain only a short section describing the antibacterial effects of AA or UA. Therefore, our review article aims to provide the reader with a broader understanding of the activity of these acids against pathogenic bacteria. The bacteria in the human body can live in the planktonic form and create a biofilm structure. Therefore, we found it valuable to present the action of AA and UA on both planktonic and biofilm cultures. The article also presents mechanisms of the biological activity of these substances against microorganisms.

scholarly journals Oleanolic Acid, Ursolic Acid and Apigenin from Ocimum basilicum as Potential Inhibitors of the SARS-CoV-2 Main Protease: A Molecular Docking Study

2021 ◽  
pp. 1-16
Author(s):  
Aristote Matondo ◽  
Jason T. Kilembe ◽  
Etienne M. Ngoyi ◽  
Carlos N. Kabengele ◽  
Giresse N. Kasiama ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Biological Activities ◽  
Ocimum Basilicum ◽  
In Vivo Studies ◽  
Molecular Docking Study ◽  
Docking Score ◽  
Main Protease ◽  
Potential Inhibitors

Aim: The present study aims at identifying potential inhibitors from a set of ten compounds from Ocimum basilicum against the SARS-CoV-2 main protease, the chymotrypsin-like protease (3CLpro). Materials and Methods: Computational studies by molecular docking (Autodock tool) were used to obtain the scoring function of ten phytochemicals in interaction with the SARS-CoV-2 main protease. The pharmacokinetic behavior of the high-docking score compounds was addressed by using SwissADME and pkCSM webservers. Results: Three high-docking score ligands were identified as hit compounds mainly the oleanolic acid (-8.55 kcal/mol), the ursolic acid (-8.21 kcal/mol) and apigenin (-7.52 kcal/mol). Their pharmacokinetic profile revealed that they have good therapeutic profile of druggability and safe. The biological activities of the three compounds especially their anti-inflammatory properties in relation with the excessive production of proinflammatory cytokines in the most severe form of the COVID-19 were also highlighted.  Conclusion: COVID-19 outbreak is a serious public health threat that requires immediate action. In order to combat this pandemic, several strategies are used and the identification of potential inhibitors of the main protease of the virus is one of the widely used strategies. Here, three potential inhibitors from Ocimum basilicum plant (leaves) were pinpointed. Further in-vitro and in-vivo studies are needed that will clarify the role of Ocimum basilicum for the management of COVID-19 disease.

scholarly journals A REVIEW ON URSOLIC ACID: A NATURALLY OBTAINED PENTACYCLIC TRITERPENE

2021 ◽  
pp. 1-5
Author(s):  
NARGEES SHAIKH ◽  
GAURANG SAWANT ◽  
NIKHIL DIXIT
Keyword(s):  
Natural Products ◽  
Traditional Medicine ◽  
Ursolic Acid ◽  
Pentacyclic Triterpene ◽  
Treatment Approaches ◽  
Pentacyclic Triterpenes ◽  
Novel Treatment

Natural products derived from plants have been used for decades in traditional medicine. Many classes of compounds exist in plants such as saponins, alkaloids, anti-oxidants, etc. Pentacyclic triterpenes are also one of the compounds occurring in plants. In this class Ursolic acid is a well-recognized compound that is available from various sources like seeds as well as fruits and possess many types of activities and is a bright contender for developing novel treatment approaches for treating diseases.

scholarly journals Triterpenoid profile of fruit and leaf cuticular waxes of edible honeysuckle Lonicera caerulea var. kamtschatica

2017 ◽  
Vol 86 (1) ◽  
Author(s):  
Rafał Becker ◽  
Cezary Pączkowski ◽  
Anna Szakiel
Keyword(s):  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Fruit Ripening ◽  
Cuticular Waxes ◽  
Lonicera Caerulea ◽  
Pentacyclic Triterpenes ◽  
Pests And Diseases ◽  
Leaf Waxes ◽  
Compositional Study

Edible honeysuckle (honeyberry) <em>Lonicera caerulea</em> is becoming popular as a novel berry crop with several useful features such as early fruit ripening and exceptional hardiness, particularly resistance to pests and diseases as well as severe frosts in winter and droughts in summer. The triterpenoid profile of fruit and leaf cuticular waxes of edible honeysuckle (a Russian cultivar Chernichka) was analyzed by GC-MS. The major compounds identified were the tetracyclic triterpenoids campesterol, cholesterol, cycloartanol, cycloart-23-ene-3,25-diol, 24-methylenecycloartanol (only in leaves), sitosterol, stigmasta-3,5-dien-7-one, and stigmasterol; and the pentacyclic triterpenes: <em>α</em>-amyrin, <em>β</em>-amyrin, hop-22(29)-en-3-one, oleanolic acid, and ursolic acid. Several remarkable features of the analyzed triterpenoid contents were revealed, including the relatively low abundance of triterpenoids in fruit waxes (6.5% of wax extract) compared to leaf waxes (22%), and a particularly high proportion of tetracyclic triterpenoids (tetracyclic to pentacyclic compound ratios of 4:1 in fruits and almost 7:1 in leaves). These rare features distinguish the triterpenoid profile of the cuticular waxes of <em>L. caerulea</em> var. <em>kamtschatica</em> from the majority of triterpenoid profiles in plant cuticular waxes investigated to date. To our knowledge, this is the first quantitative compositional study on triterpenoid compounds in the cuticular waxes of edible honeysuckle, supplementing the knowledge of cuticular triterpenoid diversity and distribution.

Sterols and Triterpenes in Cell Culture of Hyssopus officinalis L.

2003 ◽  
Vol 58 (5-6) ◽  
pp. 308-312 ◽  
Author(s):  
Zuzanna Skrzypek ◽  
Halina Wysokińska
Keyword(s):  
Cell Culture ◽  
Cell Suspension ◽  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Cell Suspension Cultures ◽  
Suspension Cultures ◽  
Pentacyclic Triterpenes ◽  
Hyssopus Officinalis

Abstract Cell suspension cultures from hypocotyl-derived callus of Hyssopus officinalis were found to produce two sterols i. e. β-sitosterol (1) and stigmasterol (2), as well as several known pentacyclic triterpenes with an oleanene and ursene skeleton. The triterpenes were identified as oleanolic acid (3), ursolic acid (4), 2α, 3β-dihydroxyolean-12-en-28-oic acid (5), 2α, 3β- dihydroxyurs-12-en-28-oic acid (6), 2α, 3β, 24-trihydroxyolean-12-en-28-oic acid (7), and 2α,3β, 24-trihydroxyurs-12-en-28-oic acid (8). Compounds 5-8 were isolated as their acetates (6, 8) or bromolactone acetates(5, 7)

Synthesis and Antitumor Activity of Ring A-modified Glycyrrhetinic Acid Derivatives

2011 ◽  
Vol 66 (5) ◽  
pp. 521-532
Author(s):  
René Csuk ◽  
Stefan Schwarz ◽  
Bianka Siewert ◽  
Ralph Kluge ◽  
Dieter Ströhl
Keyword(s):  
Biological Activities ◽  
Human Tumor ◽  
Glycyrrhetinic Acid ◽  
Tumor Cell Lines ◽  
Human Tumor Cell ◽  
Pentacyclic Triterpene ◽  
Human Tumor Cell Lines ◽  
Sulforhodamine B ◽  
Sulforhodamine B Assay ◽  
Apoptotic Activity

The pentacyclic triterpene glycyrrhetinic acid is an interesting natural product exhibiting various biological activities. Especially its ability to induce apoptosis in tumor cells is of high scientific interest. In this study we altered the lipophilicity in ring A by derivatization at positions C-2 and C-3. The consequences of these variations on the cytotoxicity were investigated applying a colorimetric sulforhodamine B assay using 8 different human tumor cell lines. An acridine orange/ethidium bromide (AO/EB) test and a trypan blue test were used to determine the extent of apoptotic activity of some of these compounds

Synthesis of Some New Tetracyclic Pyrimidine Derivatives Using Exocyclic α,β-Unsaturated Ketone and Evaluation of Their Antitumor Activities

2016 ◽  
Vol 12 (8) ◽  
pp. 311-317
Author(s):  
Kamelia El-Mahdy
Keyword(s):  
Antitumor Activity ◽  
Spectroscopic Data ◽  
Acid Hydrazide ◽  
Chloroacetic Acid ◽  
Equimolar Amount ◽  
Unsaturated Ketone ◽  
Cyanoacetic Acid ◽  
Antitumor Activities ◽  
Pyrimidine Derivatives ◽  
Cyanoacetic Acid Hydrazide

Thiazolopyrimidine 2 was obtained from the reaction of dihydropyrimidinone with chloroacetic acid and benzaldehyde. Thiazolopyrimidine 2 containing an α,β-unsaturated ketonic function [-CH=CH-CO-] has been used as a component of Michael addition with an equimolar amount of dinucleophiles to give a series of novel tetracyclic pyrimidine derivatives. Treatment of thiazolopyrimidine 2 with uracil, aminotriazole, cyanoacetic acid hydrazide, o-phenylenediamine or diaminopyridine afforded the corresponding pyridopyrimidine, triazolopyrimidine, pyrazolone, benzodiazepine and triazepine derivative, respectively. The detailed synthesis, spectroscopic data, and antitumor activity for synthesized compounds were reported.

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