Synthesis and antiplasmodial activity of lycorine derivatives

Cedrón, Juan Carlos; Gutiérrez, David; Flores, Ninoska; Ravelo, Ángel G.; Estévez‐Braun, Ana

doi:10.1016/j.bmc.2010.05.023

Cited by 56 publications

(59 citation statements)

References 25 publications

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“…The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl 3 -MeOH, 20:1) to yield 8 [18,19] (70 mg, 0.245 mmol).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and biological evaluation of lycorine derivatives as dual inhibitors of humanacetylcholinesterase and butyrylcholinesterase

Wang

Wan

et al. 2012

Chemistry Central Journal

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BackgroundAlzheimer’s disease (AD) is a neurologically degenerative disorder that affects more than 20 million people worldwide. The selective butyrylcholinesterase (BChE) inhibitors and bivalent cholinesterase (ChE) inhibitors represent new treatments for AD.FindingsA series of lycorine derivatives (1–10) were synthesized and evaluated for anti-cholinesterase activity. Result showed that the novel compound 2-O-tert-butyldimethylsilyl-1-O-(methylthio)methyllycorine (7) was a dual inhibitor of human acetylcholinesterase (hAChE) and butyrylcholinesterase (hBChE) with IC50 values of 11.40 ± 0.66 μM and 4.17 ± 0.29 μM, respectively. The structure-activity relationships indicated that (i) the 1-O-(methylthio)methyl substituent in lycorine was better than the 1-O-acetyl group for the inhibition of cholinesterase; (ii) the acylated or etherified derivatives of lycorine and lycorin-2-one were more potent against hBChE than hAChE; and (iii) the oxidation of lycorine at C-2 decreases the activity.ConclusionAcylated or etherified derivatives of lycorine are potential dual inhibitors of hBChE and hAChE. Hence, further study on the modification of lycorine for ChE inhibition is necessary.

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“…The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl 3 -MeOH, 20:1) to yield 8 [18,19] (70 mg, 0.245 mmol).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and biological evaluation of lycorine derivatives as dual inhibitors of humanacetylcholinesterase and butyrylcholinesterase

Wang

Wan

et al. 2012

Chemistry Central Journal

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“…Among the Amaryllidaceae alkaloids, galanthamine, is used for the treatment of mild and moderate cases of Alzheimer's disease (AD) (Howes, Perry, 2011). Lycorine, a major alkaloid found in many Amaryllidaceae species, has been shown to have a wide variety of biological activities such as antitumoral , antimalarial (Cedron et al, 2010), hepatoprotective (Ilavenil, Kaleeswaran, Ravikumar, 2012), antiviral (He et al, 2013), antifungal (Shen et al, 2014) and antiparasitic (Giordani et al, 2012) activities. Due to its diverse biological properties, it has been to the interest of phytochemists to determine the content of this alkaloid using various analytical techniques in Amaryllidaceous plants (Abou-Donia et al, 2007;Petruczynik et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Application of HPLC-DAD for the quantification of Lycorine in Galanthus elwesii Hook

Emir

Bozkurt

et al. 2017

Braz. J. Pharm. Sci.

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In the present study, a reversed-phase high-performance liquid chromatographic method has been used for the quantitative determination of lycorine in the aerial parts and bulbs of G. elwesii Hook. A simple method for the extraction of lycorine in low mass plant samples was employed utilizing pre-packed columns with diatomaceous earth (Extrelut®). The chromatographic separation was performed using an isocratic system with a mobile phase of trifluoroacetic acid-water-acetonitrile (0.01:92.5:7.5, v/v/v) applied at a flow rate 1 mL min -1 using diode array detector. The content of lycorine in the bulbs and aerial parts of G. elwesii collected from Demirci (Manisa) was found as 0.130 and 0.162 %, respectively. Additionally, in the bulbs of the specimens collected from Sogucak (Balikesir), lycorine was quantified as 0.055 %, whereas in the aerial parts, it was determined as 0.006 %. The method was validated partially with respect to system specificity, linearity, accuracy, precision, limits of detection (LOD) and quantitation (LOQ). Validation procedures displayed that the method was specific, accurate and precise.Uniterms: Alkaloids. Amaryllidaceae. Plant extracts. High Performance Liquid Chromatography/method validation. High Perfomance Liquid Chromatography/quantitative analysis.

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“…In 1956, scientists determined the three-dimensional structure of lycorine by single crystal. Modern pharmacological research shows that lycorine has anti-inflammatory, inhibiting acetylcholinesterase, alkali resistant malaria, cardiovascular protection and a variety of tumor cell apoptosis induced by alkali, lycorine also has broad antiviral activity, such as SARS virus, herpes simplex virus, vaccinia virus, Punta Toro virus and Rift Valley fever virus [2][3][4] . On the other hand, the study of lycorine and its derivatives have also greatly promoted the progress in the treatment of diseases such as cancer, Alzheimer's disease, viral infection and other serious harm to human health [5][6][7] .…”

Section: Introductionmentioning

confidence: 99%