A comprehensive review: Biological activity, modification and synthetic methodologies of prenylated flavonoids

Shi, Shao-Chun; Li, Jichong; Zhao, Xuemei; Liu, Qingbo; Song, Shao‐Jiang

doi:10.1016/j.phytochem.2021.112895

Cited by 71 publications

(33 citation statements)

References 156 publications

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“…With the activity against two strains that cause dermatological disorders, our study, furthermore, corroborates the ethnomedicinal use of V. guianensis for treating skin diseases. Because of the restricted occurrence of isoflavones in the plant kingdom and the increasing use of prenylated flavonoids for the development of new therapeutic agents, 43 V. guianensis presents a source of valuable natural products. Apart from our phytopharmacological findings, our study revealed deceptive coupling patterns in the proton NMR spectra observed for 3′,4′-disubstituted isoflavonoids, which have been the reason for several erroneously reported structures and which we resolved by higher order spectra simulations.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Antimicrobial Prenylated Isoflavones from the Leaves of the Amazonian Medicinal Plant Vatairea guianensis Aubl.

et al. 2022

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Vatairea guianenis Aubl. (Fabaceae) is an Amazonian medicinal plant species traditionally used for treating skin diseases. In an initial screening, a V. guianensis leaf extract and its subextracts showed antibacterial and antifungal activities. The EtOAc subextract was selected for chemical workup and afforded five known (1−4 and 8) and six undescribed isoflavones, vatairenones C−H (5−7 and 9−11). All isoflavones are prenylated in position C-8, displaying either chain-prenylated (1−7) or ring-closed forms (8−11). The most bioactive compound (3) exhibited in vitro activity against clinically relevant bacteria and fungi with IC 50 values ranging from 6.8 to 26.9 μM. Due to its broad antimicrobial activity and low general toxicity, compound 3 is a potential lead compound for structural modifications. The results of the present study support the ethnomedicinal use of V. guianensis in the treatment of dermatological disorders. 1 H NMR spectra of some of the isolated compounds showed intricate signal patterns, which might explain repeated errors in assigning the correct structure of the isoflavonoid B-ring in the literature and which we resolved by higher order spectra simulations.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Antimicrobial Prenylated Isoflavones from the Leaves of the Amazonian Medicinal Plant Vatairea guianensis Aubl.

et al. 2022

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“…Strikingly, compound 15 , a 4-prenylated acridone had a slightly higher binding energy (with protein 5R82) than compound 3 . The prenyl group has been known to increase affinity for biological membranes and also an improved interaction with proteins [ 31 , 32 ]. It is instructive to note that the pyranoacridones listed above are also a variant of 4-prenylation; with cyclization between C-3 OH and C-4 prenyl group.…”

Section: Resultsmentioning

confidence: 99%

Acridone Alkaloids: In-Silico Investigation Against SARS-CoV-2 Main Protease

et al. 2022

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The severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) infection that causes COVID-19 disease is still a major public health concern around the world. The main protease encoded by SARS-CoV-2 is a promising target for COVID-19 therapeutic development since it plays a crucial role in the virus’s life cycle. Repurposing known bioactive molecules is an effective strategy to fast-track the delivery of hits and leads in drug discovery. In this regard, this study assesses in-silico , 17 acridone-based alkaloids for their activity against SARS-CoV-2 main protease. The quantum chemical computations imply that the acridone alkaloids will interact better in the active sites of the enzymes due to their low energy gap. They also have good oral bioavailability as rationalized by “no rule of five violation" and favorable pharmacokinetics parameters. From the docking results, many of the alkaloids displayed a higher binding affinity than nirmatrelvir, an authorised protease inhibitor. Compound 3 (5-hydroxynoracronycine alcohol), with the better binding affinities (6W63, − 7.094 kcal/mol; 5R82, − 5.839 kcal/mol) and unique structural features is a viable candidate that could be investigated further for development of a novel target specific chemotherapeutic agent to stop SARS-CoV-2 invasion.

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“…Prenylation is a ubiquitous modification distributed in primary metabolism as well as biosynthetic pathways of diverse natural products, including terpenoids, 1-3 alkaloids, 4,5 polyketides, 6,7 flavonoids, 8,9 nonribosomal peptides, 10,11 and ribosomally synthesized and post-translationally modified peptides (RiPPs) [12][13][14] . Prenyl groups can contribute an enhancement of lipophilicity to the molecules, aiding their interaction with lipid membranes; and consequently they grant better membrane permeability and bioavailability.…”

Section: Introductionmentioning

confidence: 99%

LimF is a versatile prenyltransferase for histidine-C-geranylation on diverse non-natural substrates

et al. 2022

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Prenylation plays an important role in diversifying structure and function of secondary metabolites. Although several cyanobactin prenyltransferases have been characterized, their modes of action are mainly limited to the modification of electron-rich hetero atoms. Here we report a unique prenyltransferase originating from Limnothrix sp. CACIAM 69d, referred to as LimF, which catalyzes an unprecedented His-C-geranylation.Interestingly, LimF executes the geranylation on not only its native peptide substrate but also a wide range of exotic peptides, including thioether-closed macrocycles. We have also serendipitously uncovered an ability of Tyr-O-geranylation as the secondary function of LimF, indicating it is an unusual bifunctional prenyltransferase. Crystallographic analysis of LimF complexed with a pentapeptide substrate and a prenyl donor analog provides structural basis for its unique His recognition and its bifunctionality. Lastly, we show the LimF's prenylation ability on various bioactive molecules containing an imidazole group, highlighting its potential as a versatile biocatalyst for site-specific geranylation.

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A comprehensive review: Biological activity, modification and synthetic methodologies of prenylated flavonoids

Cited by 71 publications

References 156 publications

Antimicrobial Prenylated Isoflavones from the Leaves of the Amazonian Medicinal Plant Vatairea guianensis Aubl.

Antimicrobial Prenylated Isoflavones from the Leaves of the Amazonian Medicinal Plant Vatairea guianensis Aubl.

Acridone Alkaloids: In-Silico Investigation Against SARS-CoV-2 Main Protease

LimF is a versatile prenyltransferase for histidine-C-geranylation on diverse non-natural substrates

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