Discovery and current developments of isoindolinone-based fungal natural products

Bailly, Christian

doi:10.1016/j.ejmcr.2023.100112

Cited by 4 publications

(3 citation statements)

References 223 publications

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“…The high yield of 1 instead of restricticin in the rice culture suggested the primary amine-scavenging pathway via the activation of cichorine biogenetic pathways. In fact, there were some hybrid products of cichorine, such as aspercryptin, 22 audicichorines B and C, 23 and N-(4′carboxybutyl)cichorine 24,25 (Figure S2), which were produced in A. nidulans by deletion of the negative regulator. To the best of our knowledge, compound 1 was the first example produced by condensation of the cichorine precursor with glycine amine via heterologous expression of the exogenous gene cluster in A. nidulans.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Discovery of a Hybrid Molecule with Phytotoxic Activity by Genome Mining, Heterologous Expression, and OSMAC Strategy

Lu,

Li,

Dou

et al. 2024

J. Agric. Food Chem.

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Genome mining in association with the OSMAC (one strain, many compounds) approach provides a feasible strategy to extend the chemical diversity and novelty of natural products. In this study, we identified the biosynthetic gene cluster (BGC) of restricticin, a promising antifungal agent featuring a reactive primary amine, from the fungus Aspergillus sclerotiorum LZDX-33-4 by genome mining. Combining heterologous expression and the OSMAC strategy resulted in the production of a new hybrid product (1), along with N-acetyl-restricticin (2) and restricticinol (3). The structure of 1 was determined by spectroscopic data, including optical rotation and electronic circular dichroism (ECD) calculations, for configurational assignment. Compound 1 represents a fusion of restricticin and phytotoxic cichorin. The biosynthetic pathway of 1 was proposed, in which the condensation of a primary amine of restricticin with a precursor of cichorine was postulated. Compound 1 at 5 mM concentration inhibited the growth of the shoots and roots of Lolium perenne, Festuca arundinacea, and Lactuca sativa with inhibitory rates of 71.3 and 88.7% for L. perenne, 79.4 and 73.0% for F. arundinacea, and 58.2 and 52.9% for L. sativa. In addition, compound 1 at 25 μg/mL showed moderate antifungal activity against Fusarium fujikuroi and Trichoderma harzianum with inhibition rates of 22.6 and 31.6%, respectively. These results suggest that heterologous expression in conjunction with the OSMAC approach provides a promising strategy to extend the metabolite novelty due to the incorporation of endogenous metabolites from the host strain with exogenous compounds, leading to the production of more complex compounds and the acquisition of new physiological functions.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Discovery of a Hybrid Molecule with Phytotoxic Activity by Genome Mining, Heterologous Expression, and OSMAC Strategy

Lu,

Li,

Dou

et al. 2024

J. Agric. Food Chem.

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“…In the same study, two additional compounds classified as alkaloids were isolated, termed erinacerin N and M. This nomenclature contrasts with the study by Ashour et al, where compounds bearing the same names exhibit entirely distinct structures [59,60]. Several erinacerins have been found to possess inhibitory effects on α-glucosidases, suggesting their potential as antidiabetic agents [57,60,61]. Wang et al demonstrated that erinacerins Q, S, and T exhibit inhibitory activities against both protein tyrosine phosphatase-1B (PTP1B) and α-glucosidase [60].…”

Section: Erinacerinsmentioning

confidence: 92%

“…Several erinacerins have been found to possess inhibitory effects on α-glucosidases, suggesting their potential as antidiabetic agents [ 57 , 60 , 61 ]. Wang et al demonstrated that erinacerins Q, S, and T exhibit inhibitory activities against both protein tyrosine phosphatase-1B (PTP1B) and α-glucosidase [ 60 ].…”

Section: Identification Of Novel Bioactive Compounds In Her...mentioning

confidence: 99%

Unveiling the Chemical Composition and Biofunctionality of Hericium spp. Fungi: A Comprehensive Overview

Kostanda,

Musa,

Pereman

2024

IJMS

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In recent years, research on mushrooms belonging to the Hericium genus has attracted considerable attention due to their unique appearance and well-known medicinal properties. These mushrooms are abundant in bioactive chemicals like polysaccharides, hericenones, erinacines, hericerins, resorcinols, steroids, mono- and diterpenes, and corallocins, alongside essential nutrients. These compounds demonstrate beneficial bioactivities which are related to various physiological systems of the body, including the digestive, immune, and nervous systems. Extensive research has been conducted on the isolation and identification of numerous bioactive chemicals, and both in vitro and in vivo studies have confirmed their antimicrobial, antioxidant, immunomodulatory, antidiabetic, anticholesterolemic, anticancer, and neuroprotective properties. Therefore, this review aims to provide a comprehensive summary of the latest scientific literature on the chemical composition and secondary metabolites profile of Hericium spp. through an introduction to their chemical characteristics, speculated biosynthesis pathways for key chemical families, potential toxicological aspects, and a detailed description of the recent updates regarding the bioactivity of these metabolites.

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Synthesis of 3‐Methyleneisoindolin‐1‐ones via Rhodium(III)‐Catalyzed C−H/N−H Activation and Annulation of N‐Methoxybenzamides with Potassium Vinyltrifluoroborate

Kumar,

Gandeepan

2024

Chemistry An Asian Journal

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Isoindolinones are vital heterocyclic compounds in medicinal chemistry, notable for their diverse bioactivities. Significant attention has been devoted to their preparation; however, existing methods are unsuitable for constructing unsubstituted 3‐methyleneisoindolin‐1‐ones. Herein, we present a rhodium(III)‐catalyzed method for synthesizing unsubstituted 3‐methyleneisoindolin‐1‐ones via C‒H/N‒H activation and annulation of N‐methoxybenzamides with potassium (ethenyl)trifluoroborate. This approach offers mild reaction conditions, high regioselectivity, and efficient yields. Interestingly, sterically demanding or heterocyclic N‐methoxyaromaticamides resulted in the formation of 2‐vinyl(hetero)aromatic amides instead of 3‐methyleneisoindolin‐1‐ones. Mechanistic insights suggest a rhodacycle intermediate pathway, highlighting the method's potential for developing new bioactive isoindolinone derivatives.

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Discovery and current developments of isoindolinone-based fungal natural products

Cited by 4 publications

References 223 publications

Discovery of a Hybrid Molecule with Phytotoxic Activity by Genome Mining, Heterologous Expression, and OSMAC Strategy

Discovery of a Hybrid Molecule with Phytotoxic Activity by Genome Mining, Heterologous Expression, and OSMAC Strategy

Unveiling the Chemical Composition and Biofunctionality of Hericium spp. Fungi: A Comprehensive Overview

Synthesis of 3‐Methyleneisoindolin‐1‐ones via Rhodium(III)‐Catalyzed C−H/N−H Activation and Annulation of N‐Methoxybenzamides with Potassium Vinyltrifluoroborate

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