New acetylenic derivatives of betulin and betulone, synthesis and cytotoxic activity

Bębenek, Ewa; Kadela-Tomanek, Monika; Chrobak, Elwira; Wietrzyk, Joanna; Sadowska, Joanna; Boryczka, Stanisław

doi:10.1007/s00044-016-1713-9

Cited by 37 publications

(46 citation statements)

References 23 publications

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“…Tang JJ et al, identified a small-molecule inhibitor of SREBP, betulin, by compound screening, where SREBP is a major transcription factor that controls the biosynthesis of cholesterol, fatty acid, and triglyceride [114]. Betulin inhibits SREBP by binding SCAP and making the interaction between SCAP and Insig easier, which leads to the ER-retention of SREBP.…”

Section: Anti-hyperlipidaemic Activitymentioning

confidence: 99%

Betulin, a Pentacyclic Tri-Terpenoid: An Hour to Rethink the Compound

Singh¹

2017

OAJTMR

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Betulin, a pentacyclic triterpenoid member of lupane family occurs widely in numerous plants. Betulin, unlike most other constituents is easily isolated that it can be utilized for various pharmacological actions. It is interesting to know that betulin can be easily extracted from bark, stem, leaves, flower, roots etc. of the plant. This review summarizes plethora of reliable pharmacological activities like antiinflammatory, anti-ulcer, anti-diabetic, anti-bacterial, anti-microbial, anti-malarial, anti-viral, anti hyperlipidaemic, anti-cancer and anti HIV exhibited by betulin and its derivatives. For this it can be utilized in herbal as well as synthetic pharmaceutical industries because of its promising efficacy and low levels of toxicity. Although betulin possess a wide range of pharmacological activities, there is still lack of awareness of its proper utilization in the field of medicine. So, need of the hour is to refocus on naturally occurring betulin and its derivatives to avoid side effects caused by synthetic compounds utilized in treating various ailments. Therefore, the aim of the present review is to re-explore the potential of betulin, as an alternative to the compounds possessing higher side effects. Keywords: Table1:Represents the physical properties of betulin [1,30,31] Occurrence of Betulin in NatureBetulin has long been explored by research scientist because of the fact that it has anticancer properties [35,36] and its derivative Betulinic acid is favored due to its anti-HIV activity [12,6,37]. As mentioned in Figure 1: betulin has three most prominent positions where chemical modifications can be easily accomplished, namely primary hydroxyl group at position C-28, secondary hydroxyl group at position C-3, and alkene moiety at position C-20.The bio-chemical modifications at positions C-28 of the parent structure of betulin produces betulinic acid [12,27,[38][39][40][41]. The chief source of Betulin is bark of Birch trees, belonging to family Betulaceae the family of flowering plants. Mostly placed in order Fagales, it can also be placed in order Betulales. The subfamilies include Betuloideae genera Betula (birch), Alnus (alder) and Coryloideaegenera Carpinus (hornbeam), Corylus (hazel), Ostrya and Ostryopsis [42][43][44]. Betulin, a pentacyclictriterpenoid is derived from linear hydrocarbon squalene [31]. Triterpenes have three main classes oleane, ursane and lupane triterpenes. Lupane class comprises betulin, betulinic acid, lupeol [6,45]. Triterpenes are used as traditional herbal medicine and the esters of betulin and fatty acids are used in the production of cosmetics and as plasticizers for PVC [31,46] (Table 2). Pharmacological StudiesBetulin, as we all known till now possess vast pharmacological properties including choleritic, antihelmintic, powerful prophylactic, anti-HIV, antimutagene agent, antiviral, antifungal, anti-leukemia, anti-leishmanial, anti-inflammatory, immunomodulator activities. The latest research suggests some of the major pharmacological properties as discu...

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Section: Anti-hyperlipidaemic Activitymentioning

confidence: 99%

Betulin, a Pentacyclic Tri-Terpenoid: An Hour to Rethink the Compound

Singh¹

2017

OAJTMR

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“…The 3-oxo derivative of betulin betulone and its derivatives, exhibiting antitumor, antiinflammatory, aniparasitic, and anti-HIV properties, also demonstrate in vitro cytotoxic activity against different cancer cell lines. [10][11][12][13][14][15][16][17][18][19][20][21][22] Recent studies indicate a clear demand for betulone as a building block for creating effective anticancer agents with minimal side effects. [20][21][22] Currently, the main method of synthesis of betulin oxoderivatives is its oxidation.…”

Section: Introductionmentioning

confidence: 99%

Oxidation of a wood extractive betulin to biologically active oxo-derivatives using supported gold catalysts

et al. 2019

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“…[10-14] Pyrazole derivatives have been reported as antimicrobial agents in a number of publications,[15-17] but as anti- Acinetobacter, they are unknown. In our efforts to get potent antimicrobial agents,[18] we have synthesized several pyrazole-derived terphenyl like novel molecules. We have found pyrazole-derived N-aryl amines as anti-methicillin resistant Staphylococcus aureus (anti-MRSA) agents.…”

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confidence: 99%

“…[18] Aromatic amine derivatives are an integral part of many potent antimicrobial agents. [19] All these novel molecules are characterized by 1 H and 13 C NMR spectroscopy.…”

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confidence: 99%

“…We reported several N-aryl derivatives of the pyrazole as anti-MRSA agents up to 16 μM concentration. [18] To get the N-aryl pyrazole derivatives as potent antimicrobial agents, we synthesized several novel molecules (Scheme 1) to test against Gram-positive and Gram-negative bacteria. Nearly all of the test compounds showed moderate activity against Gram-positive bacteria in zone of inhibition studies.…”

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Synthesis and antimicrobial studies of novel derivatives of 4-(4-formyl-3-phenyl-1H-pyrazol-1-yl)benzoic acid as potent anti-Acinetobacter baumannii agents

Allison

Delancey

Ramey

et al. 2017

Bioorganic & Medicinal Chemistry Letters

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Microbial resistance to antibiotics is a global concern. The World Health Organization (WHO) has identified antimicrobial resistance as one the three greatest threats for human beings in the 21st century. Without urgent and coordinated action, the world is moving toward a post-antibiotic era, in which normal infections or minor injuries may become fatal. In an effort to find new agents, we report the synthesis and antimicrobial activities of 40 novel 1,3-diphenyl pyrazole derivatives. These compounds have shown zones of growth inhibition up to 85 mm against Acinetobacter baumannii. We tested the active compounds against this Gram-negative bacterium in minimum inhibitory concentration (MIC) tests and found activity with concentration as low as 4 μg/mL.

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New acetylenic derivatives of betulin and betulone, synthesis and cytotoxic activity

Cited by 37 publications

References 23 publications

Betulin, a Pentacyclic Tri-Terpenoid: An Hour to Rethink the Compound

Betulin, a Pentacyclic Tri-Terpenoid: An Hour to Rethink the Compound

Oxidation of a wood extractive betulin to biologically active oxo-derivatives using supported gold catalysts

Synthesis and antimicrobial studies of novel derivatives of 4-(4-formyl-3-phenyl-1H-pyrazol-1-yl)benzoic acid as potent anti-Acinetobacter baumannii agents

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