Chemical constituents from the leaves and branches of Annona coriacea Mart. (Annonaceae)

Rocha, Giovanna Nogueira da Silva Avelino Oliveira; Dutra, Lívia Macedo; Paz, Weider H.P.; Silva, Felipe M. A. da; Costa, Emmanoel V.; Almeida, Jackson Roberto Guedes da Silva

doi:10.1016/j.bse.2021.104297

Cited by 6 publications

(7 citation statements)

References 40 publications

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“…Aporphine alkaloids and their derivatives are important constituents of Annona spp. ; thus, liriodenine and anonaine have been widely reported 53,60–63 . Also, anonaine has been the most reported aporphine alkaloid in the Annonacaea family 64 .…”

Section: Resultsmentioning

confidence: 98%

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Application of effect‐directed analysis using TLC–bioautography for rapid isolation and identification of antidiabetic compounds from the leaves of Annona cherimola Mill.

Galarce‐Bustos,

Obregón,

Vallejos‐Almirall

et al. 2023

Phytochemical Analysis

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IntroductionType 2 diabetes mellitus is a globally prevalent chronic disease characterised by hyperglycaemia and oxidative stress. The search for new natural bioactive compounds that contribute to controlling this condition and the application of analytical methodologies that facilitate rapid detection and identification are important challenges for science. Annona cherimola Mill. is an important source of aporphine alkaloids with many bioactivities.ObjectiveThe aim of this study is to isolate and identify antidiabetic compounds from alkaloid extracts with α‐glucosidase and α‐amylase inhibitory activity from A. cherimola Mill. leaves using an effect‐directed analysis by thin‐layer chromatography (TLC)–bioautography.MethodologyGuided fractionation for α‐glucosidase and α‐amylase inhibitors in leaf extracts was done using TLC–bioassays. The micro‐preparative TLC was used to isolate the active compounds, and the identification was performed by mass spectrometry associated with web‐based molecular networks. Additionally, in vitro estimation of the inhibitory activity and antioxidant capacity was performed in the isolated compounds.ResultsFive alkaloids (liriodenine, dicentrinone, N‐methylnuciferine, anonaine, and moupinamide) and two non‐alkaloid compounds (3‐methoxybenzenepropanoic acid and methylferulate) with inhibitory activity were isolated and identified using a combination of simple methodologies. Anonaine, moupinamide, and methylferulate showed promising results with an outstanding inhibitory activity against both enzymes and antioxidant capacity that could contribute to controlling redox imbalance.ConclusionsThese high‐throughput methodologies enabled a rapid isolation and identification of seven compounds with potential antidiabetic activity. To our knowledge, the estimated inhibitory activity of dicentrinone, N‐methylnuciferine, and anonaine against α‐glucosidase and α‐amylase is reported here for the first time.

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Section: Resultsmentioning

confidence: 98%

“…; thus, liriodenine and anonaine have been widely reported. 53,[60][61][62][63] Also, anonaine has been the most reported aporphine alkaloid in the Annonacaea family. 64 However, its biological effects are still being studied.…”

Section: Identification By Uhplc-ms/ms Analysismentioning

confidence: 99%

Application of effect‐directed analysis using TLC–bioautography for rapid isolation and identification of antidiabetic compounds from the leaves of Annona cherimola Mill.

Galarce‐Bustos,

Obregón,

Vallejos‐Almirall

et al. 2023

Phytochemical Analysis

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“…Among those hits, 7 were previously reported from this plant source: Annomontine, methoxyannomontine 14 , argentinine 39 , atherosperminine 37 , coreximine 37 , liriodenine 39 , and reticuline 37 . Besides being closely related to some of these putative structures, 13 further hits had already been reported from other Annona species: benzyltetrahydroisoquinolines anomuricine and anomurine (both known from A. muricata 31 ), N -methylcoclaurine (from A. sericea 40 ), reticuline N ‐oxide ( A. salzmanni 41 ) and tembetarine (tentatively known from A. salzmanni 41 ); proaporphines such as glaziovine and stepharine, both reported from A. purpurea 42 , 43 ; tetrahydroprotoberberines kikemanine ( A. glabra 44 ), pessoine (from A. spinescens 45 ), and stepholidine ( A. cherimolia 46 ); aporphines such as nornuciferine ( A. muricata 47 ), obovanine ( A. coriacea 48 ) and roemerine (from both A. squamosa 49 and A. senegalensis 50 ). Most other hits corresponded to metabolites occurring in other Annonaceous genera.…”

Section: Technical Validationmentioning

confidence: 99%

Implementation of a MS/MS database for isoquinoline alkaloids and other annonaceous metabolites

et al. 2022

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This data descriptor reports on the upload to a public repository (GNPS) of the IQAMDB, IsoQuinoline and Annonaceous Metabolites Data Base, comprising 320 tandem mass spectra. This project originated from our in-house collection of isoquinolines. The diversity of compounds included in this database was further extended through the contribution of two additional laboratories involved in isoquinoline alkaloids research: University of Angers and University of Manaus. The generated MS/MS data were processed and annotated on an individual basis to promote their straightforward reuse by natural product chemists interested in either the description of new isoquinoline alkaloids or the dereplication of isoquinoline-containing samples. The interest of the current repertoire for dereplication purposes has been validated based on the molecular networking of the well-investigated plant model Annona montana against the IQAMDB‐implemented GNPS.

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“…The genus of Annona is one of the 120 genera of the Annonaceae family and contains more than 119 species of trees and shrubs, most of them distributed in tropical areas of the Americas and Africa [6]. The majority of these species are found in tropical America, with more than 105 species (26 of them are endemic) and 10 species distributed in tropical Africa [10,34]. It has been reported that this genus is the second or the third largest genus in the Annonaceae family [35].…”

Section: Annona Generamentioning

confidence: 99%

“…Numerous Annona species furnish edible fruits like Annona muricata ("graviola"), Annona crassiflora ("araticum") and Annona sqaumosa ("fruta do conde") [2]. Most of the fruits are consumed either in fresh form or used in desserts, juices and ice cream preparations [34]. Despite Annona having many species, only limited species of this family are economically important such as A. squamosa L. (sugar apple), A. cherimola Mill.…”

Section: Annona Generamentioning

confidence: 99%

Traditional Uses, Phytochemistry and Pharmacological Activities of Annona Genus

Kazman¹,

Hanrahan²

2022

Preprint

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In 1789, the Annonaceae family was cataloged by de Jussieu. It encompasses tropical and subtropical plants which are widespread in distribution across various continents such as Asia, South and Central America, Australia and Africa. The genus of Annona is one of the 120 genera of the Annonaceae family and contains more than 119 species of trees and shrubs. The majority of these species are found in tropical America with more than 105 species (26 of them are endemic). Due to its edible fruits and medicinal properties, Annona is the most important genus of Annonaceae family. Despite Annona having many species, only limited species of this family are economically important such as A. squamosa L. (sugar apple), A. cherimola Mill. (Cherimoya), A. muricata L. (guanabana or soursop), A. atemoya Mabb. (atemoya), a hybrid between A. cherimola and A. squamosa, A. reticulata L. (custard apple), A. glabra L. (pond-apple) and A. macroprophyllata Donn. Sm. (ilama). Phytochemically, several classes of secondary metabolites such as acetogenins, essential oils, alkaloids, terpenoids and flavonoids have been described in this genus. A variety of pharmacological activities have been reported from various parts of Annona species specially leaves and seeds including applications against antibacterial, anticancer, antidiabetic and anti-inflammatory.

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Chemical constituents from the leaves and branches of Annona coriacea Mart. (Annonaceae)

Cited by 6 publications

References 40 publications

Application of effect‐directed analysis using TLC–bioautography for rapid isolation and identification of antidiabetic compounds from the leaves of Annona cherimola Mill.

Application of effect‐directed analysis using TLC–bioautography for rapid isolation and identification of antidiabetic compounds from the leaves of Annona cherimola Mill.

Implementation of a MS/MS database for isoquinoline alkaloids and other annonaceous metabolites

Traditional Uses, Phytochemistry and Pharmacological Activities of Annona Genus

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