<sup>1</sup>H qNMR Quantification of Annonaceous Acetogenins in Crude Extracts of <i>Annona muricata</i> L. Fruit Pulp

Bonneau, Natacha; Cynober, Timothé; Jullian, Jean‐Christophe; Champy, Pierre

doi:10.1002/pca.2668

Cited by 16 publications

(4 citation statements)

References 23 publications

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“…As a multi-disciplinary approach, the present study focused on designating phytochemicals from leaf extracts of soursop (Annona muricata), a plant known for its broad spectrum anti-cancer activity against osteosarcoma or bone cancer through analytical and in silico chemistry approach with con rmation from in vitro cell line studies. Annona muricata L, widely known as graviola or soursop is considered to have potential phytochemicals like phenols, saponins, terpenoids, avonoids, isoquinoline alkaloids and annonaceous acetogenins (Alali et al 1999;Bonneau et al 2017;Shanmugam et al 2022) that are reported to be effective against various cancer cell lines (Pieme et al 2014). Several research works have con rmed that the entire soursop tree exhibits selective and signi cant anticancer activity, with leaves being the most potent (Mishra et al 2013;Rupprecht et al 1990).…”

Section: Introductionmentioning

confidence: 99%

Anti-proliferative effect of leaf phytochemicals of soursop (Annona muricata L.) against human osteosarcoma in vitro

Shanmugam,

Narmadha,

Ravikumar

et al. 2024

Chem. Pap.

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Soursop (Annona muricata) is being used in treating various types of cancers and there is no report on effect of soursop leaf phytochemicals against osteosarcoma. Current study identi ed 28 metabolites from ethyl acetate leaf (EAL) extract through GC-MS chemopro ling and subjected to in silico analysis against the potential protein target, Platelet Derived Growth Factor Receptor α (PDGFRA) of osteosarcoma, including Absorption, Distribution, Metabolism, and Excretion and Toxicity (ADMET) analysis to identify possible hit compounds. This resulted in three hit leaf bioactives namely, 2'-hydroxy-5'-methyl chalcone, linoleic acid and annonacin showing good binding a nity with a docking score of -7.4, -7.0 and -6.9 kcal/mol respectively. With ADMET analysis, 2'-hydroxy-5'-methyl chalcone and linoleic acid obeyed Lipkinsi's rule of ve, whereas annonacin showed slight violation. Among the three docked complexes, annonacin exhibited good stability during molecular dynamic simulation performed with PDGFRA. Hence, concentration of the key marker compound, annonacin in EAL concentrate is found to be 5.032± 0.13 mg/g of leaf sample. Further, EAL concentrate exhibited cytotoxicity (IC 50 value) on MG-63 osteosarcoma cells in vitro for concentrations ranging from 10 to 25 µg/mL and nuclear imaging of osteoblast cells treated with EAL concentrate at 25 µg/mL concentration exhibited typical symptoms of apoptosis. In vitro cytotoxicity along with nuclear imaging con rmed EAL concentrate from soursop to be a potential drug candidate in developing new anti-cancer agent against osteosarcoma.

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Section: Introductionmentioning

confidence: 99%

Anti-proliferative effect of leaf phytochemicals of soursop (Annona muricata L.) against human osteosarcoma in vitro

Shanmugam,

Narmadha,

Ravikumar

et al. 2024

Chem. Pap.

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“…Annonaceous acetogenins are present at a millimolar level in tropical plants from Annona genus. , Their various biological properties, both detrimental and beneficial, along with their widespread consumption, particularly as fruits, make their characterization an urgent need . The accurate structural characterization of acetogenins is difficult because of their long carbon chains.…”

Section: Introductionmentioning

confidence: 99%

Dereplication of Acetogenins from Annona muricata by Combining Tandem Mass Spectrometry after Lithium and Copper Postcolumn Cationization and Molecular Networks

Poyer

Laboureur

Hebra

et al. 2022

J. Am. Soc. Mass Spectrom.

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Annonaceous acetogenins are natural products held responsible for atypical Parkinsonism due to chronic consumption in traditional medicine or as food, leading to the development of analytical strategies for their complete chemical characterization in complex mixtures. Characterization by tandem mass spectrometry (MS/MS) of acetogenins using collision-induced dissociation from lithium adducts provides additional structural information compared to protonated or sodiated species such as ketone location on the acetogenin backbone. However, very low intensity diagnostic ions together with the lack of extensive structural information regarding position of OH and THF substituents limit this approach.Copper adducts led to diagnostic fragment ions that allow us to identify the position of oxygen rings and hydroxyl substituents. Fragmentation rules were established on the basis of acetogenin standards allowing the identification of 45 over the 77 analogues observed in an extract of Annona muricata by LC−MS/MS using postcolumn infusion of copper sulfate (CuSO 4 ) solution. Molecular networks that were generated thanks to specific fragmentations obtained with copper led to the distinction of THF ring position or to the identification of hydroxylated lactone, for instance.

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“…To minimize some of these problems, Nuclear Magnetic Resonance (NMR) spectrometry can be a suitable solution. NMR is a powerful technique for structure determination, that has also emerged as an important analytical tool in the biomedical and pharmaceutical field for quantitative determination of drugs in different matrices, providing high specificity and sensitivity [5][6][7]. Quantitative NMR (qNMR) have several advantages such as great reproducibility, automation, quantification without identical standard material, and total detection permitting an unbiased overview of the sample composition [8,9].…”

Section: Introductionmentioning

confidence: 99%

Quantification of drugs encapsulated in liposomes by 1H NMR

Guimarães

Noro

Loureiro

et al. 2019

Colloids and Surfaces B: Biointerfaces

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Liposomes are one of the most important and extensively studied drug delivery system due to their ability to encapsulate different kinds of drugs. Exploiting the advantages of 1 H Nuclear Magnetic Resonance (NMR) spectrometry, we established a rapid and easy method for quantification of drugs encapsulated in liposomes. An internal standard, pyridine, was used for quantitative determination of drug concentration. Two different drugs were involved in this work, one hydrophilic, methotrexate disodium salt, and another hydrophobic, tamoxifen. The specificity and selectivity of the suggested method were evaluated by the absence of overlapping of at least one signal of each drug with pyridine in the NMR spectrum. The accuracy and precision of the method were assessed by adding a known amount of each drug to unloaded liposomes. Results obtained by quantitative NMR (qNMR) were validated and confirmed by comparing with two other traditional techniques, Ultraviolet-Visible (UV-vis) spectrophotometry and High-Performance Liquid Chromatography (HPLC). It was found that the results were consistent with the ones obtained from our proposed qNMR method. Considering all the experiments conducted in this study, we deliberate that qNMR can be a suitable tool for the determination of drugs encapsulated in liposomes.

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¹H qNMR Quantification of Annonaceous Acetogenins in Crude Extracts of Annona muricata L. Fruit Pulp

Abstract: A simple, accurate and specific method for quantification of AAGs content was developed and validated for routine application to fruit pulp crude extracts. Copyright © 2017 John Wiley & Sons, Ltd.

Cited by 16 publications

References 23 publications

Anti-proliferative effect of leaf phytochemicals of soursop (Annona muricata L.) against human osteosarcoma in vitro

Anti-proliferative effect of leaf phytochemicals of soursop (Annona muricata L.) against human osteosarcoma in vitro

Dereplication of Acetogenins from Annona muricata by Combining Tandem Mass Spectrometry after Lithium and Copper Postcolumn Cationization and Molecular Networks

Quantification of drugs encapsulated in liposomes by 1H NMR

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1H qNMR Quantification of Annonaceous Acetogenins in Crude Extracts of Annona muricata L. Fruit Pulp

Abstract: A simple, accurate and specific method for quantification of AAGs content was developed and validated for routine application to fruit pulp crude extracts. Copyright © 2017 John Wiley & Sons, Ltd.

Cited by 16 publications

References 23 publications

Anti-proliferative effect of leaf phytochemicals of soursop (Annona muricata L.) against human osteosarcoma in vitro

Anti-proliferative effect of leaf phytochemicals of soursop (Annona muricata L.) against human osteosarcoma in vitro

Dereplication of Acetogenins from Annona muricata by Combining Tandem Mass Spectrometry after Lithium and Copper Postcolumn Cationization and Molecular Networks

Quantification of drugs encapsulated in liposomes by 1H NMR

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¹H qNMR Quantification of Annonaceous Acetogenins in Crude Extracts of Annona muricata L. Fruit Pulp