Piperlongumine (piplartine) as a lead compound for anticancer agents – Synthesis and properties of analogues: A mini-review

Piska, Kamil; Gunia‐Krzyżak, Agnieszka; Koczurkiewicz, Paulina; Wójcik-Pszczoła, Katarzyna; Pękala, Elżbieta

doi:10.1016/j.ejmech.2018.06.057

Cited by 103 publications

(66 citation statements)

References 43 publications

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“…Alkaloids are defined by the presence of a heterocyclic nitrogen atom, and have been increasingly attracting pharmaceutical researchers to develop therapeutic agents as lead compounds [1][2][3]. Indole alkaloids are characterized by the presence of a structural moiety of indole, and have been extensively studied as they possess important biological properties such as antihypertension [4], antihistamine [5], anticonvulsant [6], anti-leishmanial [7], antidiabetic [8], anti-HIV-1, anti-inflammatory [9], anticancer [10], and antibacterial activities [11].…”

Section: Introductionmentioning

confidence: 99%

Novel Deep Eutectic Solvent Based on Levulinic Acid and 1,4-Butanediol as an Extraction Media for Bioactive Alkaloid Rutaecarpine

Sun

Liu

et al. 2019

Processes

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Deep eutectic solvents (DESs) are increasingly receiving interest as a new type of green and sustainable alternative to hazardous organic solvents. In this work, a novel DES based on levulinic acid (La) and 1,4-butanediol (Buta) as an extraction media was developed for extracting the bioactive alkaloid rutaecarpine from the unripe fruits of Tetradium ruticarpum. 24 different DESs consisting of choline chloride, betaine, sugar alcohols, organic acids, amides, and sugars were prepared and tailored to test their extraction efficiency. After initial screening, a hydrophilic DES composed of La and Buta with 1:0.5 molar ratio containing 25% water was tailored for the highest extraction efficiency, followed by the optimizations of molar ratio and water content. The interaction between the molecules of La-Buta DES was investigated by nuclear magnetic resonance spectroscopy in order to confirm its deep eutectic supermolecular structure feature. The extraction conditions were optimized by single-factor experiments, including extraction temperature, extraction time, and solid-liquid ratio. The developed La-Buta DES extraction procedure was successfully applied for the analysis of rutaecarpine in Chinese patent medicines containing the unripe fruits of T. ruticarpum. The excellent property of La-Buta DES indicated its potential as a promising green solvent instead of conventional organic solvent for the extraction of rutaecarpine from the unripe fruits of T. ruticarpum, and that it can used as a sustainable and safe extraction media for other applications.

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Section: Introductionmentioning

confidence: 99%

Novel Deep Eutectic Solvent Based on Levulinic Acid and 1,4-Butanediol as an Extraction Media for Bioactive Alkaloid Rutaecarpine

Sun

Liu

et al. 2019

Processes

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“…Recently, the evidences from experimental studies have shown that piperlongumine (PL), a natural compound isolated from long pepper piper longum L, possess multiple anti-tumor effects for a wide range of human malignancies, including lung [13], liver [14], prostate [15], breast [16], and colorectal [17] cancer. Suppression of kinase activity, regulation of the expression of the transcription factor, and dysfunction of signaling transduction were identified to be the underlying mechanisms [18]. However, there has been no study regarding the mechanisms of PL on the regulation of glycolysis in human NSCLC.…”

Section: Ivyspringmentioning

confidence: 99%

Repression of Hexokinases II-Mediated Glycolysis Contributes to Piperlongumine-Induced Tumor Suppression in Non-Small Cell Lung Cancer Cells

Zhou

Yu³

et al. 2019

Int. J. Biol. Sci.

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Deregulation of glycolysis is a common phenomenon in human non-small cell lung cancer (NSCLC). In the present study, we reported the natural compound, piperlongumine, has a profound anti-tumor effect on NSCLC via regulation of glycolysis. Piperlongumine suppressed the proliferation, colony formation and HK2-mediated glycolysis in NSCLC cells. We demonstrated that exposure to piperlongumine disrupted the interaction between HK2 and VDAC1, induced the activation of the intrinsic apoptosis signaling pathway. Moreover, our results revealed that piperlongumine down-regulated the Akt signaling, exogenous overexpression of constitutively activated Akt1 in HCC827 and H1975 cells significantly rescued piperlongumine-induced glycolysis suppression and apoptosis. The xenograft mouse model data demonstrated the pivotal role of suppression of Akt activation and HK2-mediated glycolysis in mediating the in vivo antitumor effects of piperlongumine. The expression of HK2 was higher in malignant NSCLC tissues than that of the paired adjacent tissues, and was positively correlated with poor survival time. Our results suggest that HK2 could be used as a potential predictor of survival and targeting HK2 appears to be a new approach for clinical NSCLC prevention or treatment.

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“…A couple of years ago, piperlongumine (isolated from Piper longum) [29][30][31] has been found to exhibit superior cytotoxic properties. Recently, we were able to access several dimers of piperlongumine [32][33] , and to show them of even higher cytotoxicity than the parent compound.…”

Section: Introductionmentioning

confidence: 99%

“…[40][41] because some interesting biological activities have been reported for this hybrid composed from (E) 4-hydroxy-3,5dimethoxycinnamic acid and choline. Among other activities, this molecule holds anti-inflammatoric [42][43] , anti-oxidative 44 and anti-angiogenic [29][30] properties, as well as some potential as an inhibitor for the enzyme acetylcholinesterase 45 . Shown as early in 1852 46 , it can be extracted from plant material, and there is also one lengthy synthesis reported by E. Späth in 1920 47 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of sinapine and its unprecedented ruthenium-catalyzed [2+2] photodimerization

et al. 2019

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Piperlongumine (piplartine) as a lead compound for anticancer agents – Synthesis and properties of analogues: A mini-review

Cited by 103 publications

References 43 publications

Novel Deep Eutectic Solvent Based on Levulinic Acid and 1,4-Butanediol as an Extraction Media for Bioactive Alkaloid Rutaecarpine

Novel Deep Eutectic Solvent Based on Levulinic Acid and 1,4-Butanediol as an Extraction Media for Bioactive Alkaloid Rutaecarpine

Repression of Hexokinases II-Mediated Glycolysis Contributes to Piperlongumine-Induced Tumor Suppression in Non-Small Cell Lung Cancer Cells

Synthesis of sinapine and its unprecedented ruthenium-catalyzed [2+2] photodimerization

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