scholarly journals Chemical Strategies towards the Synthesis of Betulinic Acid and Its More Potent Antiprotozoal Analogues

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1081 ◽  
Author(s):  
André Barreto Cunha ◽  
Ronan Batista ◽  
María Ángeles Castro ◽  
Jorge Mauricio David
Keyword(s):  
Betulinic Acid ◽  
Wide Spectrum ◽  
Antimicrobial Activities ◽  
Pentacyclic Triterpene ◽  
Triterpene Acid ◽  
Amide Derivatives ◽  
Plant Families ◽  
Antileishmanial Activities ◽  
Chemical Strategies ◽  
Natural Precursor

Betulinic acid (BA, 3β-hydroxy-lup-20(29)-en-28-oic acid) is a pentacyclic triterpene acid present predominantly in Betula ssp. (Betulaceae) and is also widely spread in many species belonging to different plant families. BA presents a wide spectrum of remarkable pharmacological properties, such as cytotoxic, anti-HIV, anti-inflammatory, antidiabetic and antimicrobial activities, including antiprotozoal effects. The present review first describes the sources of BA and discusses the chemical strategies to produce this molecule starting from betulin, its natural precursor. Next, the antiprotozoal properties of BA are briefly discussed and the chemical strategies for the synthesis of analogues displaying antiplasmodial, antileishmanial and antitrypanosomal activities are systematically presented. The antiplasmodial activity described for BA was moderate, nevertheless, some C-3 position acylated analogues showed an improvement of this activity and the hybrid models—with artesunic acid—showed the most interesting properties. Some analogues also presented more intense antileishmanial activities compared with BA, and, in addition to these, heterocycles fused to C-2/C-3 positions and amide derivatives were the most promising analogues. Regarding the antitrypanosomal activity, some interesting antitrypanosomal derivatives were prepared by amide formation at the C-28 carboxylic group of the lupane skeleton. Considering that BA can be produced either by isolation of different plant extracts or by chemical transformation of betulin, easily obtained from Betula ssp., it could be said that BA is a molecule of great interest as a starting material for the synthesis of novel antiprotozoal agents.

scholarly journals A Review on Preparation of Betulinic Acid and Its Biological Activities

Molecules ◽  
2021 ◽  
Vol 26 (18) ◽  
pp. 5583
Author(s):  
Hanghang Lou ◽  
Hao Li ◽  
Shengliang Zhang ◽  
Hongyun Lu ◽  
Qihe Chen
Keyword(s):  
Betulinic Acid ◽  
Biological Activities ◽  
Wide Spectrum ◽  
Pharmacological Properties ◽  
Biosynthetic Pathways ◽  
Antitumor Effects ◽  
Pharmacological Activities ◽  
Pentacyclic Triterpene ◽  
Plane Trees ◽  
Anti Hiv

Betulinic acid, a pentacyclic triterpene, is distributed in a variety of plants, such as birch, eucalyptus and plane trees. It shows a wide spectrum of biological and pharmacological properties, such as anti-inflammatory, antibacterial, antiviral, antidiabetic, antimalarial, anti-HIV and antitumor effects. Among them, the antitumor activity of betulinic acid has been extensively studied. However, obtaining betulinic acid from natural resources can no longer meet the needs of medicine and nutrition, so methods such as chemical synthesis and microbial biotransformation have also been used to prepare betulinic acid. At the same time, with the development of synthetic biology and genetic engineering, and the elucidation of the biosynthetic pathways of terpenoid, the biosynthesis of betulinic acid has also been extensively researched. This article reviews the preparation of betulinic acid and its pharmacological activities, in order to provide a reference for the research and utilization of betulinic acid.

Synthesis and Biological Activity of 28-Amide Derivatives of 23-Hydroxy Betulinic Acid as Antitumor Agent Candidates

2013 ◽  
Vol 9 (7) ◽  
pp. 920-925 ◽  
Author(s):  
Yi Bi ◽  
Jinyi Xu ◽  
Fei Sun ◽  
Xiaoming Wu ◽  
Wencai Ye ◽  
...  
Keyword(s):  
Biological Activity ◽  
Betulinic Acid ◽  
Antitumor Agent ◽  
Amide Derivatives ◽  
Derivatives Of

scholarly journals A Brief Insight into Microbial Corrosion and its Mitigation with Eco-friendly Inhibitors

2021 ◽  
Vol 7 (3) ◽  
Author(s):  
M. Lavanya
Keyword(s):  
Electrochemical Impedance ◽  
Wide Spectrum ◽  
Present Review ◽  
Electrochemical Reactions ◽  
Microbial Corrosion ◽  
Engineering Applications ◽  
Microbially Influenced Corrosion ◽  
Catastrophic Failures ◽  
Chemical Strategies ◽  
Insight Into

AbstractCorrosion results from the electrochemical reactions between the metal and its existing environment. Corrosion results in severe and expensive damage to a wide spectrum of industries. When microbes are involved in corrosion it is seldom possible to economically evaluate its impact. Microbially influenced corrosion is recognized to cause catastrophic failures contributing to approximately 20% of the annual losses. In many engineering applications, microbially influenced corrosion control is of prime importance. Expensive, toxicity and sometimes, even ineffectiveness of the current chemical strategies to mitigate microbially influenced corrosion have shifted the interest towards eco-friendly inhibitors. The present review discusses microbial induced corrosion in various metals and its inhibition through eco-friendly inhibitors. In addition, the study also reviews the morphological and electrochemical impedance results.

A New Pentacyclic Triterpene Acid from Lantana indica

1991 ◽  
Vol 54 (3) ◽  
pp. 755-758 ◽  
Author(s):  
S. K. Singh ◽  
V. J. Tripathi ◽  
R. H. Singh
Keyword(s):  
Pentacyclic Triterpene ◽  
Triterpene Acid

scholarly journals Hydroxy Pentacyclic Triterpene Acid, Kaempferol, Inhibits the Human 5-Hydroxytryptamine Type 3A Receptor Activity

2022 ◽  
Vol 23 (1) ◽  
pp. 544
Author(s):  
Shinhui Lee ◽  
Hee-Soo Seol ◽  
Sanung Eom ◽  
Jaeeun Lee ◽  
Chaelin Kim ◽  
...  
Keyword(s):  
Nervous System ◽  
Binding Sites ◽  
Molecular Level ◽  
Neuroprotective Effect ◽  
Site Directed Mutagenesis ◽  
Pentacyclic Triterpene ◽  
Independent Manner ◽  
Triterpene Acid ◽  
Cudrania Tricuspidata ◽  
Wide Range

Monoamine serotonin is a major neurotransmitter that acts on a wide range of central nervous system and peripheral nervous system functions and is known to have a role in various processes. Recently, it has been found that 5-HT is involved in cognitive and memory functions through interaction with cholinergic pathways. The natural flavonoid kaempferol (KAE) extracted from Cudrania tricuspidata is a secondary metabolite of the plant. Recently studies have confirmed that KAE possesses a neuroprotective effect because of its strong antioxidant activity. It has been confirmed that KAE is involved in the serotonergic pathway through an in vivo test. However, these results need to be confirmed at the molecular level, because the exact mechanism that is involved in such effects of KAE has not yet been elucidated. Therefore, the objective of this study is to confirm the interaction of KAE with 5-HT3A through electrophysiological studies at the molecular level using KAE extracted from Cudrania tricuspidata. This study confirmed the interaction between 5-HT3A and KAE at the molecular level. KAE inhibited 5-HT3A receptors in a concentration-dependent and voltage-independent manner. Site-directed mutagenesis and molecular-docking studies confirmed that the binding sites D177 and F199 are the major binding sites of human 5-HT3A receptors of KAE.

scholarly journals Phytochemical characterization, and antioxidant and antimicrobial activities of white cabbage extract on the quality and shelf life of raw beef during refrigerated storage

RSC Advances ◽  
2020 ◽  
Vol 10 (68) ◽  
pp. 41430-41442
Author(s):  
Momna Rubab ◽  
Ramachandran Chelliah ◽  
Kandasamy Saravanakumar ◽  
Jong-Rae Kim ◽  
Daesang Yoo ◽  
...  
Keyword(s):  
Phenolic Compounds ◽  
Biological Activities ◽  
Wide Spectrum ◽  
Antimicrobial Activities ◽  
Refrigerated Storage ◽  
White Cabbage ◽  
Brassica Vegetables ◽  
Cabbage Extract ◽  
Antioxidant And Antimicrobial Activities ◽  
Quality And Shelf Life

Brassica vegetables are well-characterized, containing a wide-spectrum of phenolic compounds that are responsible for their diverse biological activities like antioxidant and antimicrobial activities.

scholarly journals Bioassay-directed fractionation of a blood coagulation factor Xa inhibitor, betulinic acid from Lycopus lucidus

2018 ◽  
Vol 16 (1) ◽  
pp. 170-175 ◽  
Author(s):  
Yin-Feng Tan ◽  
Qiong Wang ◽  
Jing-Wen Gong ◽  
Xu-Guang Zhang ◽  
Yong-Hui Li ◽  
...  
Keyword(s):  
Blood Coagulation ◽  
Betulinic Acid ◽  
Blood Circulation ◽  
Arterial Occlusion ◽  
Factor Xa ◽  
Coagulation Factor ◽  
Pentacyclic Triterpene ◽  
Coronary Syndrome ◽  
Fxa Inhibitor ◽  
Lycopus Lucidus

AbstractThrombosis is a major cause of morbidity and mortality worldwide and plays a pivotal role in the pathogenesis of several cardiovascular disorders, including acute coronary syndrome, unstable angina, myocardial infarction, sudden cardiac death, peripheral arterial occlusion, ischemic stroke, deep-vein thrombosis, and pulmonary embolism. Anticoagulants, antiplatelet agents, and fibrinolytics can reduce the risks of these clinical events. Especially, the blood coagulation factor Xa (FXa) inhibitor is a proven anticoagulant. Promoting blood circulation, using traditional Chinese medicine (TCM), for the treatment of these diseases has been safely used for thousands of years in clinical practice. Therefore, highly safe and effective anticoagulant ingredients, including FXa inhibitors, could be found in TCM for activating the blood circulation. One FXa inhibitor, a pentacyclic triterpene (compound 1, betulinic acid) characterized by IR, MS and NMR analyses, was isolated from the ethyl acetate fraction of Lycopus lucidus by bioassay-directed fractionation. Compound 1 exhibited an inhibitory effect on FXa with IC50 25.05 μmol/L and reduced the thrombus weight in an animal model at 25-100 mg/kg. These results indicate that betulinic acid could be the potential for anticoagulant therapy.

Synthesis and Antimicrobial Evaluation of Chiral 3, 5-Diaryl-5, 6-dihydrothiazolo[ 2, 3-c][1, 2, 4]triazoles

2019 ◽  
Vol 16 (12) ◽  
pp. 978-982
Author(s):  
Pawankumar R. Tiwari ◽  
Marina E. John ◽  
Anil V. Karnik
Keyword(s):  
Wide Spectrum ◽  
Antimicrobial Activities ◽  
Dilution Method ◽  
Chiral Hplc ◽  
E Coli ◽  
Synthetic Strategy ◽  
Fused Heterocycles ◽  
Spectrum Activity ◽  
Antimicrobial Evaluation ◽  
Hplc Analyses

: Disclosed herein is a general approach for the synthesis of chiral thiazolo triazoles 5a-e. An efficient 3-step synthetic strategy has been developed to obtain the fused heterocycles in good yields. The key step involves formation of a secondary carbocation under acidic condition and intramolecular attack of the nitrogen of the 1,2,4-triazolo part leads to the formation of fused bicyclic compound in a regioselective manner. A new chiral center was created during the reaction and Chiral HPLC analyses confirmed the presence of the same and the racemic nature of the synthesized compounds. Their antimicrobial activities were evaluated by broth micro-dilution method and expressed as the minimum inhibitory concentration. The preliminary bioassay results demonstrate that most of the target compounds exhibit a significantly wide spectrum activity against S. aureus and E. coli comparable to ampicillin. The efficacies of compounds against C. albicans are either more or similar compared to Griseofulvin.

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