Oligomeric phloroglucinols with hAChE inhibitory and antibacterial activities from tropic Rhodomyrtus tomentosa

Luo, E-E; Liu, Si-Na; Wang, Zhao-Jie; Chen, Ling-Yun; Liang, Cheng-Qin; Yu, Mu-Yuan; Qin, Xu-Jie

doi:10.1016/j.bioorg.2023.106836

Cited by 3 publications

(1 citation statement)

References 43 publications

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“…Certain oligomeric proanthocyanidins display useful bioactivities, such cinnamon polyphenols characterized as antidiabetic agents [6]. There are also phloroglucinol dimers and trimers acting as acetylcholinesterase inhibitors with antibacterial properties [7], and ellagitannin trimers such as rugosin G, which is a more potent inhibitor of human histidine decarboxylase than related ellagitannin monomers and dimers [8]. Various catechin oligomers have been discovered, including complex products with a high molecular weight, such as the antimicrobial ellagitannin sanguiin H-6 (C 82 H 54 O 52 , Mw: 1871.3 g/mol) active against methicillin-resistant Staphylococcus aureus (MRSA) [9,10].…”

Section: Introductionmentioning

confidence: 99%

Interaction of Norsecurinine-Type Oligomeric Alkaloids with α-Tubulin: A Molecular Docking Study

Vergoten,

Bailly

2024

Plants

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The medicinal plant Securinega virosa (Roxb ex. Willd) Baill., also known as Flueggea virosa (Roxb. ex Willd.) Royle, is commonly used in traditional medicine in Africa and Asia for the management of diverse pathologies, such as parasite infections, diabetes, and gastrointestinal diseases. Numerous alkaloids have been isolated from the twigs and leaves of the plant, notably a variety of oligomeric indolizidine alkaloids derived from the monomers securinine and norsecurinine which both display anticancer properties. The recent discovery that securinine can bind to tubulin and inhibit microtubule assembly prompted us to investigate the potential binding of two series of alkaloids, fluevirosines A–H and fluevirosinine A-J, with the tubulin dimer by means of molecular modeling. These natural products are rare high-order alkaloids with tri-, tetra-, and pentameric norsecurinine motifs. Despite their large size (up to 2500 Å3), these alkaloids can bind easily to the large drug-binding cavity (about 4800 Å3) on α-tubulin facing the β-tubulin unit. The molecular docking analysis suggests that these hydrophobic macro-alkaloids can form stable complexes with α/β-tubulin. The tubulin-binding capacity varies depending on the alkaloid size and structure. Structure-binding relationships are discussed. The docking analysis identifies the trimer fluevirosine D, tetramer fluevirosinine D, and pentamer fluevirosinine H as the most interesting tubulin ligands in the series. This study is the first to propose a molecular target for these atypical oligomeric Securinega alkaloids.

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