Research Progress on Natural Benzophenanthridine Alkaloids and their Pharmacological Functions: A Review

Han, Na; Yang, Zhiyou; Liu, Zhihui; Liu, Huijing; Yin, Jun

doi:10.1177/1934578x1601100838

Cited by 19 publications

(27 citation statements)

References 58 publications

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“…In the MS 2 spectrum, the product ions of compounds 28 , 32 and 55 are similar to those of chelerythrine, and they readily lost CH 4 due to the presence of adjacent methoxy groups in their structures. Based on the above strategy and reported literature, 36–38 compounds 28 , 32 and 55 were identified as 7‐o‐demethylchelerythrine, chelilutine and norchelerythrine, respectively. Other than sanguinarine and chelerythrine, all these compounds are reported in ECH for the first time.…”

Section: Resultsmentioning

confidence: 99%

Systematic characterization of alkaloids in Eomecon chionantha Hance using ultrahigh‐performance liquid chromatography–tandem quadrupole Exactive Orbitrap mass spectrometry with a four‐step screening strategy

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale Eomecon chionantha Hance (ECH), a traditional folk herb, is commonly used to treat traumatic injuries based on its analgesic and anti‐inflammatory properties. Previous studies have reported that alkaloids are the major bioactive components in ECH. Therefore, identification of alkaloids from ECH contributes to the discovery of its potential active ingredients and quality control in clinic treatments. Methods A four‐step screening strategy was performed as follows. (1) Extracting the accurate masses of ions related to different molecules. (2) Screening different types of compounds using their molecular cations, protonated molecules, diagnostic product ions and fragmentation pathways. (3) Comparing the characteristic product ion formulae to obtain the type and number of substituents. (4) Using the biosynthetic pathways of isoquinoline alkaloids to determine the concentration of alkaloids. Results Ultrahigh‐performance liquid chromatography–tandem quadrupole Exactive Orbitrap mass spectrometry (UHPLC/Q‐Exactive Orbitrap MS) analysis combined with the four‐step screening strategy was used to profile the alkaloids in ECH. The structures of 95 alkaloids in ECH were unambiguously identified or reasonably assigned, of which 76 were reported in ECH for the first time. Six types of benzylisoquinoline alkaloids were identified in ECH: six benzyltetrahydroisoquinolines, nine protopines, five N‐methyltetrahydroprotoberberines, six protoberberines, eight benzophenanthridines and sixty‐one dihydrobenzophenanthridines. Conclusions This comprehensive study identified the alkaloids in ECH, thus providing a practical reference for further research. The UHPLC/Q‐Exactive Orbitrap MS method, combined with the four‐step screening strategy, which was developed and successfully applied to identify the alkaloids in ECH, may also be applicable for the efficient screening of other herbal medicines.

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Section: Resultsmentioning

confidence: 99%

Systematic characterization of alkaloids in Eomecon chionantha Hance using ultrahigh‐performance liquid chromatography–tandem quadrupole Exactive Orbitrap mass spectrometry with a four‐step screening strategy

et al. 2020

Rapid Comm Mass Spectrometry

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“…Benzophenanthridine alkaloids are commonly found in Papaveraceae and Rutaceae and belong to the benzyl isoquinoline family. They have been extensively investigated for their medicinal properties and bioactive constituents [ 102 ]. Though they exhibit a variety of pharmacological functions, only those with multimodality anticancer activities are presented in the current review.…”

Section: Heterocyclic Compoundsmentioning

confidence: 99%

Synthetic and Naturally Occurring Heterocyclic Anticancer Compounds with Multiple Biological Targets

et al. 2021

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Cancer is a complex group of diseases initiated by abnormal cell division with the potential of spreading to other parts of the body. The advancement in the discoveries of omics and bio- and cheminformatics has led to the identification of drugs inhibiting putative targets including vascular endothelial growth factor (VEGF) family receptors, fibroblast growth factors (FGF), platelet derived growth factors (PDGF), epidermal growth factor (EGF), thymidine phosphorylase (TP), and neuropeptide Y4 (NY4), amongst others. Drug resistance, systemic toxicity, and drug ineffectiveness for various cancer chemo-treatments are widespread. Due to this, efficient therapeutic agents targeting two or more of the putative targets in different cancer cells are proposed as cutting edge treatments. Heterocyclic compounds, both synthetic and natural products, have, however, contributed immensely to chemotherapeutics for treatments of various diseases, but little is known about such compounds and their multimodal anticancer properties. A compendium of heterocyclic synthetic and natural product multitarget anticancer compounds, their IC50, and biological targets of inhibition are therefore presented in this review.

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“…On the other hand, benzophenanthridines are reputed for their bioavailability because they contained more often ionic bond besides their bioactivity. Their mode of action in cancer therapy includes either the inhibition of mitosis via a reaction of the imine bond with the sulfhydryl nucleophile in protein and enzyme or the enzymatic activities of DNA Topoisomerase I and Topoisomerase II by implantation into DNA molecules to retard the fast proliferation of tumor cells [81].…”

Section: Plant-based Compounds With Anticancer Featuresmentioning

confidence: 99%

Plant-Derived Compounds against Microbial Infections and Cancers

Bitchagno¹,

Nchiozem-Ngnitedem²,

Wandji³

et al. 2021

Bioactive Compounds in Nutraceutical and Functional Food for Good Human Health

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Plants synthesize and preserve a variety of metabolites known as natural products. Many of them are easily extractable and can be used as starting material or chemical scaffolds for various purposes, especially in drug discovery. Numbers of reports have listed valuable candidates with privilege scaffolds currently in active development as drugs. New compounds with anticancer and antiinfective activities have been discovered recently, some presented these backbones. The present book chapter aims to highlight these findings from plants which can be considered valuable for the development of new drugs against malignant cells and infective diseases. Interest in anti-infective agents is increasing due to the resistance of microorganisms to existing drugs and newly emerging infectious diseases. This resistance is also, nowadays, associated to some forms of cancers. In addition, the value of plants as essential part in the health care pipeline in low- and middle-income countries is under consideration even though these countries are almost all surrounded by a rich and untapped biodiversity. People are always relying on “modern drugs and treatment” which is unfortunately not affordable to all. Therefore, the present compilation of data on plant-derived compounds can inspire the formulation of ameliorated traditional medicines (ATM) against the targeted diseases and the conservation of species.

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Research Progress on Natural Benzophenanthridine Alkaloids and their Pharmacological Functions: A Review

Cited by 19 publications

References 58 publications

Systematic characterization of alkaloids in Eomecon chionantha Hance using ultrahigh‐performance liquid chromatography–tandem quadrupole Exactive Orbitrap mass spectrometry with a four‐step screening strategy

Systematic characterization of alkaloids in Eomecon chionantha Hance using ultrahigh‐performance liquid chromatography–tandem quadrupole Exactive Orbitrap mass spectrometry with a four‐step screening strategy

Synthetic and Naturally Occurring Heterocyclic Anticancer Compounds with Multiple Biological Targets

Plant-Derived Compounds against Microbial Infections and Cancers

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