An overview of limonoid synthetic derivatives as promising bioactive molecules

Wang, Shaochi; Kuperman, Laura L.; Song, Zhihui; Chen, Yutian; Liu, K; Xia, Zongping; Xu, Yungen; Yu, Qiuning

doi:10.1016/j.ejmech.2023.115704

Cited by 3 publications

(1 citation statement)

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“…Priority is generally given to the most abundant polycyclic limonoids in plants, in particular, the classical intact limonoids, such as limonin and nomilin, and to smaller fragmented limonoids with easier synthetic access. The field of limonoids is very active, with more than 1600 compounds characterized over the past 15 years [2] and a profusion of synthetic derivatives (>800) elaborated during roughly the same period [121]. But in this vast molecular armamentarium, the use of degraded limonoids of the prieurianin type has been little considered, either because the molecules are too complex structurally or not well known and hardly available or because of the limited information concerning their bioactivities and mechanism of action.…”

Section: Discussionmentioning

confidence: 99%

Insights into the Mechanism of Action of the Degraded Limonoid Prieurianin

Vergoten,

Bailly

2024

IJMS

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Limonoids are extremely diversified in plants, with many categories of products bearing an intact, rearranged or fragmented oxygenated scaffold. A specific subgroup of fragmented or degraded limonoids derives from the tetranortriterpenoid prieurianin, initially isolated from the tree Trichilia prieuriana but also found in other plants of the Meliaceae family, including the more abundant species Aphanamixis polystachya. Prieurianin-type limonoids include about seventy compounds, among which are dregeanin and rohitukin. Prieurianin and analogs exhibit insecticidal, antimicrobial, antiadipogenic and/or antiparasitic properties but their mechanism of action remains ill-defined at present. Previous studies have shown that prieurianin, initially known as endosidin 1, stabilizes the actin cytoskeleton in plant and mammalian cells via the modulation of the architecture and dynamic of the actin network, most likely via interference with actin-binding proteins. A new mechanistic hypothesis is advanced here based on the recent discovery of the targeting of the chaperone protein Hsp47 by the fragmented limonoid fraxinellone. Molecular modeling suggested that prieurianin and, to a lesser extent dregeanin, can form very stable complexes with Hsp47 at the protein–collagen interface. Hsp-binding may account for the insecticidal action of the product. The present review draws up a new mechanistic portrait of prieurianin and provides an overview of the pharmacological properties of this atypical limonoid and its chemical family.

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Section: Discussionmentioning

confidence: 99%