Naturally occurring plant isoquinoline N-oxide alkaloids: Their pharmacological and SAR activities

Pachycereus marginatus (DC.) Britton & Rose and Ibervillea sonorae (S. Watson) Greene have been used in the Mexican traditional medicine for the treatment of various diseases, including cancer. The present study aims to investigate the cytotoxic activity of these plants against a murine lymphoma. Soxhlet extraction of dried and powdered plant material was performed with methanol. Also, a further partitioning of these methanolic extracts with hexane and ethyl acetate was achieved. The in vitro cytotoxic activity against the murine lymphoma L5178Y-R cell line was assessed via the colorimetric MTT assay. The methanol extract from P. marginatus exhibited high cytotoxic activity (up to 94%) at concentrations ranging from 3.9 to 500 µg/mL; however, hexane and ethyl acetate partitions from this methanolic extract showed lower but significant (p < 0.05) concentration-dependent cytotoxicity (hexane partition up to 94% at 500 µg/mL; ethyl acetate partition up to 94% at 65.5 µg/mL). The methanolic extract and partitions derived from I. sonorae also showed significant (p < 0.05) and concentration-dependent cytotoxicity against L5178Y-R cells at concentrations ranging from 7.81 to 500 µg/mL (methanolic extract up to 63% at 500 µg/mL; hexane partition up to 76% at 250 µg/mL; ethyl acetate partition up to 73% at 500 µg/mL). These results demonstrate that the methanol extracts and partitions from P. marginatus and I. sonorae possess significant cytotoxic activity against the murine lymphoma L5178Y-R and validate the ethnobotanical use of these plants for the treatment of diseases consistent with cancer symptomatology. Previous scientific reports describe the isolation of isoquinoline alkaloids of P. margi-* Corresponding author. R. Quintanilla-Licea et al. 1522natus as well as cucurbitacins from I. sonorae, phytochemicals that could be responsible for their observed cytotoxic activity in this research. The direct extraction with methanol of medicinal plants allows extracting of both high and low-polarity compounds, contrary to the simple extraction with water that only allows obtaining compounds of high polarity. The subsequent partition of the methanol extract with a solvent of low polarity (hexane) and another of medium polarity (ethyl acetate) allows making a preliminary fractionation of the bioactive molecules present in the plant that will facilitate the bioguided chromatographic isolation of the pure compounds responsible for the biological activity of the plant.

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“…Similar alkaloids have been isolated from both cacti [32] [33]. Cactus alkaloids are of simple chemical constitution.…”

Section: Pachycereus Marginatusmentioning

confidence: 63%

Cytotoxic Effect of Methanol Extracts and Partitions of Two Mexican Desert Plants against the Murine Lymphoma L5178Y-R

Quintanilla-Licea¹,

Gómez-Flores²,

Samaniego-Escamilla³

et al. 2016

AJPS

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“…Coptisine is a typical quaternary proberberine alkaloid (QPA) with a parent nucleus of isoquinoline (Figure ), which plays a vital role in the secondary metabolism of herbals like CC . By far, efforts to promote natural QPAs’ bioactivities have been conducted by applying structural modifications.…”

Section: Structure‐activity Relationshipmentioning

confidence: 99%

“…Structure‐activity relationship studies demonstrated that QPAs’ activity was affected by (1) quaternary nitrogen atom, (2) character and size of substituent at C‐13, (3) aromatic substituent on ring C and (4) substituents type on ring A and D. To begin with, tetrahydroprotoberberine’ anti‐acetylcholinesterase activity was elevated after nitro substituents were introduced at ring A . Secondly, the presence of hydrophilic radical at C‐13 position could improve QPAs’ anti‐malarial activity against plasmodium falciparum while QPAs with a high lipophilicity exerted more potent anti‐bacterial activity . It is reported that an aromatic ring C contributes to a higher activity of G‐quadruplex induction and stabilization ability .…”

Section: Structure‐activity Relationshipmentioning

confidence: 99%

Coptisine from Coptis chinensis exerts diverse beneficial properties: A concise review

Luo

Deng

et al. 2019

J Cellular Molecular Medi

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Coptisine is a natural small‐molecular compound extracted from Coptis chinensis (CC) with a history of using for thousands of years. This work aimed at summarizing coptisine's activity and providing advice for its clinical use. We analysed the online papers in the database of SciFinder, Web of Science, PubMed, Google scholar and CNKI by setting keywords as ‘coptisine’ in combination of ‘each pivotal pathway target’. Based on the existing literatures, we find (a) coptisine exerted potential to be an anti‐cancer, anti‐inflammatory, CAD ameliorating or anti‐bacterial drug through regulating the signalling transduction of pathways such as NF‐κB, MAPK, PI3K/Akt, NLRP3 inflammasome, RANKL/RANK and Beclin 1/Sirt1. However, we also (b) observe that the plasma concentration of coptisine demonstrates obvious non‐liner relationship with dosage, and even the highest dosage used in animal study actually cannot reach the minimum concentration level used in cell experiments owing to the poor absorption and low availability of coptisine. We conclude (a) further investigations can focus on coptisine's effect on caspase‐1‐involved inflammasome assembling and pyroptosis activation, as well as autophagy. (b) Under circumstance of promoting coptisine availability by pursuing nano‐ or microrods strategies or applying salt‐forming process to coptisine, can it be introduced to clinical trial.

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“…According to previous reports, the main active components of the centipede were polypeptides, histamines, quinolines, and so on . Among numerous biological active ingredients, isoquinoline alkaloid showed the strong pharmacological effects, including anticancer, antimalarial, anti‐inflammatory, antioxidant, antithrombotic, antimicrobial, and other functions …”

Section: Introductionmentioning

confidence: 99%

A New 1,5‐Dihydroxy‐4‐methoxyisoquinoline from Scolopendra subspinipes mutilans

Guo

et al. 2017

Chemistry & Biodiversity

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A new isoquinoline, 1,5-dihydroxy-4-methoxyisoquinoline (1), was obtained from Scolopendra subspinipes mutilans. Compound 1 showed moderate cytotoxicity on tumour cells with IC values ranging from 13 to 26 μm against five esophageal squamous cancer cells whereas low cytotoxicity against normal human esophageal epithelial cells. Isoquinoline ring oxidized at C(1), C(4), and C(5) can enhance its cytotoxicity. In addition, compound 1 showed potent inhibitory effect (inhibition rate > 50% at 13 μm) on cell migration in human umbilical vein endothelial cells. This article mainly studies the structure and activity of 1, and more modification of 1 as a potential anticancer agent.

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Naturally occurring plant isoquinoline N-oxide alkaloids: Their pharmacological and SAR activities

Cited by 78 publications

References 201 publications

Cytotoxic Effect of Methanol Extracts and Partitions of Two Mexican Desert Plants against the Murine Lymphoma L5178Y-R

Cytotoxic Effect of Methanol Extracts and Partitions of Two Mexican Desert Plants against the Murine Lymphoma L5178Y-R

Coptisine from Coptis chinensis exerts diverse beneficial properties: A concise review

A New 1,5‐Dihydroxy‐4‐methoxyisoquinoline from Scolopendra subspinipes mutilans

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