Isolation of Three Lycorine Type Alkaloids from Rhodolirium speciosum (Herb.) Ravenna Using pH-Zone-Refinement Centrifugal Partition Chromatography and Their Acetylcholinesterase Inhibitory Activities

Correa, Diana; Pastene, Edgar; Bustamante, Luis; Baeza, Marcelo; Alarcón‐Enos, Julio

doi:10.3390/metabo10080309

Cited by 7 publications

(8 citation statements)

References 38 publications

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“…The alkaloids were extracted using classical liquid‐liquid partition methodology [27] . Initially, 5 g of bulbs were degreased with hexane (40 mL) for 1 hour in an ultrasonic bath.…”

Section: Methodsmentioning

confidence: 99%

Molecular Docking and GC/MS‐Based Approach for Identification of Anxiolytic Alkaloids from Griffinia (Amaryllidaceae) Species in a Zebrafish Model

Leite,

Sheila de Queiroz Souza,

Riceli Vasconcelos Ribeiro

et al. 2024

Chemistry & Biodiversity

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Griffinia gardneriana Ravenna, Griffinia liboniana Morren and Griffinia nocturna Ravenna (Amarillydaceae) are bulbous plants found in tropical regions of Brazil. Our work aimed to determine the alkaloid profiles of Griffinia spp. and evaluate their anxiolytic potential through in vivo and in silico assays. The plants grown in greenhouses were dried and their ground bulbs were subjected to liquid‐liquid partitions, resulting in alkaloid fractions that were analyzed by gas chromatography coupled to mass spectrometry (GC‐MS). Anxiolytic activity was evaluated in zebrafish (Danio rerio) through intraperitoneal injection at doses of 40, 100 and 200 mg/kg in light‐dark box test. GC‐MS analyses revealed 23 alkaloids belonging to different skeleton types: lycorine, homolychorine, galanthamine, crinine, haemanthamine, montanine and narcisclasine. The chemical profiles were relatively similar, presenting 8 alkaloids common to the three species. The major component for G. gardneriana and G. liboniana was lycorine, while G. nocturna consisted mainly of anhydrolycorine. All three alkaloid fractions demonstrated anxiolytic effect. Furthermore, pre‐treatment with diazepam and pizotifen drugs was able to reverse the anxiolytic action, indicating involving the GABAergic and serotonergic receptors. Molecular docking showed that the compounds vittatine, lycorine and 11,12‐dehydro‐2‐methoxyassoanine had high affinity with both receptors, suggesting them to be responsible for the anxiolytic effect.

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“…The alkaloids were extracted using classical liquid‐liquid partition methodology [27] . Initially, 5 g of bulbs were degreased with hexane (40 mL) for 1 hour in an ultrasonic bath.…”

Section: Methodsmentioning

confidence: 99%

Molecular Docking and GC/MS‐Based Approach for Identification of Anxiolytic Alkaloids from Griffinia (Amaryllidaceae) Species in a Zebrafish Model

Leite,

Sheila de Queiroz Souza,

Riceli Vasconcelos Ribeiro

et al. 2024

Chemistry & Biodiversity

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“…90 Clivia miniata (Figure 19). 91,92 Lycorine (80) has broad biological activities including antivirus, antitumor antileukemia, anti-inflammatory, anti-angiogenesis, antibacterial, and antimalarial activities, 93 and it is considered as a lead compound for a new generation of anticancer drug design. 94 Recently, lycorine (80) was found to have antiviral activity against coronaviruses, MERS-CoV, SARS-CoV, and SARS-CoV-2, with IC50 values of 2.123, 1.021, and 0.878 μM, respectively, which was comparable to antiviral drug remdesivir.…”

Section: Antiviral Alkaloids and Alkaloid-like Compounds Against Covi...mentioning

confidence: 99%

“…Figure 21. Structures of noscapine(89), chloroquine(90), ribavirin(91), favipiravir(92), rocaglamide(93), aglaroxin C (94), and zotatifin(95) …”

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confidence: 99%

Alkaloids and Alkaloid-Like Compounds are Potential Scaffolds of Antiviral Agents against SARS-CoV-2 (COVID-19) Virus

Kittakoop¹,

Darshana²,

Sangsuwan³

et al. 2022

HETEROCYCLES

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COVID-19 pandemic has an enormous impact on humans, and it has disrupted daily life of people. Moreover, COVID-19 pandemic has significant negative effects on the world economics. To prevent the viral infection, vaccines are rapidly developed and available for certain strains of SARS-CoV-2 virus.However, the emerging of new variants has caused the problems for COVID-19 vaccines due to immune escape ability, challenging the vaccine development process which usually takes years. In this regard, there is a critical need of new antiviral compounds that can be used to combat SARS-CoV-2 virus safely and effectively. This review provides an overview on alkaloids and alkaloid-like compounds, which have antiviral activity against SARS-CoV-2 virus and related coronaviruses. Drug repurposing has played a crucial role for the drug discovery of COVID-19, and many effective antiviral agents against SARS-CoV-2 virus are from commonly used drugs or antiviral leads. Antiviral natural alkaloids and derivatives, which have the activity toward SARS-CoV-2 virus and related coronaviruses, are also discussed in this review.

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“…The method provides many advantages over the conventional CPC, including a high sample loading capacity, and high purity and high concentration of the collected fractions [15]. pHzone-refining CPC has been successfully applied to the separation of alkaloids [16,17]. Previous studies have demonstrated the preparative separation of protopine and tetrahydropalmatine from C. decumbens and other medicinal plants by pH-zone-refining CCC [18][19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Large‐scale separation of alkaloids from Corydalis decumbens by pH‐zone‐refining centrifugal partition chromatography and their anticomplement activity

Xie,

Chen,

Zhu

et al. 2023

J of Separation Science

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Centrifugal partition chromatography in the pH‐zone‐refining mode was successfully applied to the separation of alkaloids from the crude extract of Corydalis decumbens. The experiment was performed with a two‐phase solvent system composed of petroleum ether‐ethyl acetate‐ethanol‐water (5:5:3:7, v/v/v/v) where triethylamine (10 mM) was added to the stationary phase and hydrochloric acid (10 mM) to the mobile phase. From 1.6 g of the crude extract, 43 mg protopine, 189 mg (+)‐egenine, and 158 mg tetrahydropalmatine were obtained with a purity of 98.2%, 94.6%, and 96.7%, respectively. Tetrahydropalmatine showed an interesting anticomplement effect with CH50 0.11 and AP50 0.25 mg/mL, respectively. In a mechanistic study, tetrahydropalmatine interacted with C1, C3, C4, and C5 components in the complement activation cascade.

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Isolation of Three Lycorine Type Alkaloids from Rhodolirium speciosum (Herb.) Ravenna Using pH-Zone-Refinement Centrifugal Partition Chromatography and Their Acetylcholinesterase Inhibitory Activities

Cited by 7 publications

References 38 publications

Molecular Docking and GC/MS‐Based Approach for Identification of Anxiolytic Alkaloids from Griffinia (Amaryllidaceae) Species in a Zebrafish Model

Molecular Docking and GC/MS‐Based Approach for Identification of Anxiolytic Alkaloids from Griffinia (Amaryllidaceae) Species in a Zebrafish Model

Alkaloids and Alkaloid-Like Compounds are Potential Scaffolds of Antiviral Agents against SARS-CoV-2 (COVID-19) Virus

Large‐scale separation of alkaloids from Corydalis decumbens by pH‐zone‐refining centrifugal partition chromatography and their anticomplement activity

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