Total Synthesis of Geranyl-Resorcinols Isolated from Mushrooms of Genus Hericium

Kobayashi, Shōji

doi:10.1055/a-1944-9623

Cited by 8 publications

(3 citation statements)

References 87 publications

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“…Of note, in a study by He et al, two isoflavones were identified and isolated in H. erinaceus mycelium: genistein and daidzein, comprising 15% and 12% of the ethanolic extract, respectively [ 33 ]. Moreover, the Hericium genus is abundant in bioactive chemicals like polysaccharides, alkaloids, hericenones, erinacines, hericerins, resorcinols, steroids, mono- and diterpenes, and corallocins [ 16 , 17 , 20 , 26 , 29 , 34 , 35 , 36 ]. Extensive research underscores the therapeutic potential of Hericium fungi, demonstrating notable antioxidative, anti-inflammatory, antimicrobial, antidiabetic, and anticancer properties.…”

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

confidence: 99%

“…Furthermore, hericenes may undergo oxidative metabolism on the geranyl side chain to produce hericenones, which may be followed by reductive metabolism to produce hydroxyhericenone. On the other hand, isoindoline 1,3-dione derivatives are transformed into corallocins (isoindoline derivatives) through reduction, followed by oxidation to produce erinacerin derivatives ( Scheme 1 ) [ 34 , 57 , 97 ].…”

Section: Speculated Biosynthesismentioning

confidence: 99%

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

confidence: 99%

Section: Speculated Biosynthesismentioning

confidence: 99%

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

Kostanda,

Musa,

Pereman

2024

IJMS

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“…Hericerins, erinacines, erinacerins, erinaceolactones, glycoproteins, polysaccharides, sterols, and various volatile compounds are some groups of bioactive compounds isolated from their fruiting bodies and mycelia [5]. A major characteristic compound in H. erinaceus belongs to a class of compounds known as hericenones, a meroterpenoid represented by its unique geranyl-resorcinol structure [6]. Hericenone C, one such meroterpenoid produced in the fruiting bodies of this mushroom, is known to be an important stimulant to produce nerve growth factors (NGF) in brain astrocytes [7].…”

Section: Introductionmentioning

confidence: 99%

Deacylated Derivative of Hericenone C Treated by Lipase Shows Enhanced Neuroprotective Properties Compared to Its Parent Compound

et al. 2023

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Hericium erinaceus, a mushroom species commonly known as Yamabushitake in Japan, is known to have a stimulatory effect on neurotrophic factors, such as brain-derived neurotrophic factor (BDNF) and nerve growth factor (NGF). Hericenone C, a meroterpenoid with palmitic acid as the fatty acid side chain, is reported to be one such stimulant. However, according to the structure of the compound, the fatty acid side chain seems highly susceptible to lipase decomposition, under in vivo metabolic conditions. To study this phenomenon, hericenone C from the ethanol extract of the fruiting body was subjected to lipase enzyme treatment and observed for changes in the chemical structure. The compound formed after the lipase enzyme digestion was isolated and identified using LC-QTOF-MS combined with 1H-NMR analysis. It was found to be a derivative of hericenone C without its fatty acid side chain and was named deacylhericenone. Interestingly, a comparative investigation of the neuroprotective properties of hericenone C and deacylhericenone showed that the BDNF mRNA expression in human astrocytoma cells (1321N1) and the protection against H2O2-induced oxidative stress was considerably higher in the case of deacylhericenone. These findings suggest that the stronger bioactive form of the hericenone C compound is in fact deacylhericenone.

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Skeletal Isomerization of Ergosterol‐5,8‐Peroxide Leading to the Discovery of Unprecedented Ergostanes and Collective Syntheses of 5,6‐Epoxysterols and (+)‐Sarocladione

Nagayasu,

Togo,

Nagai

et al. 2024

Chemistry A European J

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Skeletal isomerization of ergosterol peroxide, a primary oxidation product of ergosterol, was investigated under thermal and iron(II)‐mediated conditions. Thermal isomerization resulted in not only the isolation of the predicted 7‐hydroxy‐5,6‐epoxides but also the discovery of the unprecedented 7/9/5‐ring‐fused ergostane for the first time. The iron(II)‐mediated isomerization proceeded at ambient temperature, resulting in the formation of the expected 5,6‐epoxysterols and a ring‐opened bicyclic diketone. The diketone was further converted into novel ergostane under thermal conditions and into (+)‐sarocladione under acidic conditions. All transformations from ergosterol to sarocladione, including the isolation of the unstable diketone intermediate, were achieved at ambient temperature, confirming the biosynthetic pathway of sarocladione. Several mushroom ingredients with a 5,6‐epoxy group were synthesized stereoselectively from the isomerization products, leading to the confirmation or revision of the structures of natural products. The β‐amyloid aggregation inhibitory activity of synthetic sterols was evaluated for the first time to gain insights into the potential for dementia prevention. This study is valuable both for supplying rare sterols found in mushrooms for biological studies and for shedding light on the oxidative metabolic pathways of ergosterol.

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Total Synthesis of Geranyl-Resorcinols Isolated from Mushrooms of Genus Hericium

Cited by 8 publications

References 87 publications

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

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

Deacylated Derivative of Hericenone C Treated by Lipase Shows Enhanced Neuroprotective Properties Compared to Its Parent Compound

Skeletal Isomerization of Ergosterol‐5,8‐Peroxide Leading to the Discovery of Unprecedented Ergostanes and Collective Syntheses of 5,6‐Epoxysterols and (+)‐Sarocladione

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