Alkaloids isolated from the leaves of atemoya (Annona cherimola×Annona squamosa)

Rabêlo, Suzana Vieira; Costa, Emmanoel V.; Barison, Andersson; Dutra, Lívia Macedo; Nunes, Xirley Pereira; Tomaz, José Carlos; Oliveira, Gibson Gomes de; Lopes, Norberto P.; Santos, Maria de Fátima Costa; Almeida, Jackson Roberto Guedes da Silva

doi:10.1016/j.bjp.2015.07.006

Cited by 31 publications

(20 citation statements)

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“…Molecular mass data were obtained for each active zone: band 1 showed two probable compounds with m/z values of 266 and 296 [M + H] + , named compound 1 and compound 2 respectively (Figure F); and band 2 the most probable m/z values was 356 [M + H] + , named as compound 3 (Figure G). According to some reports of alkaloids isolated from Annona species, these inhibitory compounds could correspond to the following aporphine alkaloids: compound 1 anonaine ( m/z 266 [M + H] + ), compound 2 norlaureline or xylopine (both with m/z 296 [M + H] + ), and band 2 glaucine ( m/z values: 356 [M + H] + ) . Figure shows the chemical structures of the proposed compounds and similarity between norlaureline and xylopine, which just differ in the position of methoxy group.…”

Section: Resultsmentioning

confidence: 98%

“…HPTLC-acetylcholinesterase (AChE) bioassay photo-documented under white light of DCM (A) and methanolic extract (B); photo-documentation at 366 nm-fluorescence (C) and 254 nm-UV (D); selected bands marked with soft pencil for elution to MS via TLC-MS interface (E) and ESI-MS spectra of selected bands (F and G) [Colour figure can be viewed at wileyonlinelibrary.com] compound 1 and compound 2 respectively (Figure 1F); and band 2 the most probable m/z values was 356 [M + H] + , named as compound Figure 1G). According to some reports of alkaloids isolated from Annona species, these inhibitory compounds could correspond to the following aporphine alkaloids: compound 1 anonaine (m/z 266 [M + H] + ), compound 2 norlaureline or xylopine (both with m/z 296 [M + H] + ), and band 2 glaucine (m/z values: 356 [M + H] + ) [21][22][23].…”

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confidence: 99%

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Detection and identification of acetylcholinesterase inhibitors in Annona cherimola Mill. by effect‐directed analysis using thin‐layer chromatography‐bioassay‐mass spectrometry

Galarce‐Bustos

Pavón

Henriquez‐Aedo

et al. 2019

Phytochemical Analysis

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Introduction Acetylcholinesterase (AChE) inhibitors are considered an important strategy in the treatment of neurological disorders such as Alzheimer's disease. A simple and fast planar chromatography‐bioassay methodology has been established to detect bioactive molecules in cherimoya fruit. Objective Detect and identify AChE inhibitors in cherimoya by high‐performance thin‐layer chromatography (HPTLC)‐bioassay‐mass spectrometry (MS) and related techniques. Methodology Effect‐directed analysis by planar chromatography‐bioassay‐mass spectrometry was applied to detect and identify AChE inhibitors in pulp, peel and cherimoya seed. Bioassay was optimised establishing the following conditions: enzymatic solution (1.0 U mL−1), 1‐naphtyl acetate substrate (1.5 mg mL−1) and Fast Blue B salt (1.0 mg mL−1). TLC‐MS interface was used to directly elute the active zones into a mass spectrometer or to a micro‐vial for further off‐line studies. Results Two AChE inhibitory bands were detected in peel extracts. An analysis via HPTLC‐MS and high‐performance liquid chromatography diode array detector tandem mass spectrometry (HPLC‐DAD‐MS/MS) allowed to characterise three potential AChE inhibitors: anonaine (m/z 266 [M + H]+; UV λmax = 269.6 nm), glaucine (m/z 256 [M + H]+; UV λmax = 282.9 and 300.6 nm) and xylopine (m/z 296 [M + H]+; UV λmax = 278.5 nm). Conclusions The application of this optimised high throughput method allowed to establish the presence of three potential AChE inhibitors in cherimoya peel. For the first time AChE inhibitory capacity of these alkaloids is reported.

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Section: Resultsmentioning

confidence: 98%

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confidence: 99%

Detection and identification of acetylcholinesterase inhibitors in Annona cherimola Mill. by effect‐directed analysis using thin‐layer chromatography‐bioassay‐mass spectrometry

Galarce‐Bustos

Pavón

Henriquez‐Aedo

et al. 2019

Phytochemical Analysis

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“…The alkaloid constituents isolated by extraction with hexane and methanol from the leaves of A. atemoya collected in Petrolina in Brazil have been reported [ 30 ]. The phytochemical investigation of the methanol extract led to the identification of seven alkaloids: anonaine, asimilobine, lanuginosine, liriodenine, lysicamine, pronuciferine and stepharine were identified by mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

The Phytochemical Constituents and Pharmacological Activities of Annona atemoya: A Systematic Review

2020

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Annona atemoya also known as the custard apple is a hybrid between two Annonaceae species: Cherimoya (Annona cherimola) and the sugar apple (Annona squamosa). It is widely cultivated in tropical and subtropical continents including north and south America, Asia, Africa and Australia. Despite becoming an increasingly important commercial fruit plant due to its’ creamy succulent flesh, compared to other Annonaceae species relatively few studies have investigated the phytochemistry and bioactivities of A. atemoya. Studies that evaluated A. atemoya extracts and its constituents were searched through the databases Scopus, Pubmed and Embase from inception to June 2020. Constituents of A. atemoya include alkaloids, flavonoids, terpenes and acetogenins. The results indicate that the constituents of A. atemoya possess cytotoxic, anti-angiogenic, hypolipidemic, antioxidant, anti-inflammatory and neuroprotective activities. However, many of these studies are currently limited in quality and further phytochemical and pharmacological studies are required.

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“…O estudo fitoquímico das folhas de atemoia levou ao isolamento e determinação estrutural de sete alcaloides, sendo dois aporfínicos (anonaína e asimilobina), três oxoaporfínicos (lanuginosina, liriodenina e lisicamina) e dois proaporfínicos (pronuciferina e stefarina). 12 Atividades antinociceptiva e antiinflamatória foram relatadas para o extrato etanólico bruto das folhas, 13 bem como atividades antioxidante e antimicrobiana de extratos obtidos dos talos e folhas. 14…”

Section: Atemoia (Annona Cherimola Mill X a Squamosa L) (Annonaceae)unclassified

Center for Studies and Research of Medicinal Plants (NEPLAME): a brief historic, major advances and perspectives

Almeida

2019

Rev. Virtual Quim.

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This paper describes a little of the history of the Center for Studies and Research of Medicinal Plants (NEPLAME) of the Federal University of the São Francisco Valley (UNIVASF), which is confused with the history of the Symposium of Medicinal Plants of the São Francisco Valley (PLAMEVASF). NEPLAME was created together with the first edition of PLAMEVASF on November 15, 2007, and since then we have contributed to the chemical and pharmacological study of medicinal plants in the Caatinga biome. Besides the research, we have developed several extension activities, giving back to the population the knowledge produced in our university. We also highlight the training of human resources at undergraduate and postgraduate levels and a relevant scientific production, with the Caatinga biome being the main object of study. We hope to continue this important work and reinforce increasingly the partnership between university, society and Brazilian research funding agencies.

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Alkaloids isolated from the leaves of atemoya (Annona cherimola×Annona squamosa)

Cited by 31 publications

References 11 publications

Detection and identification of acetylcholinesterase inhibitors in Annona cherimola Mill. by effect‐directed analysis using thin‐layer chromatography‐bioassay‐mass spectrometry

Detection and identification of acetylcholinesterase inhibitors in Annona cherimola Mill. by effect‐directed analysis using thin‐layer chromatography‐bioassay‐mass spectrometry

The Phytochemical Constituents and Pharmacological Activities of Annona atemoya: A Systematic Review

Center for Studies and Research of Medicinal Plants (NEPLAME): a brief historic, major advances and perspectives

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