Antioxidant p-terphenyl compounds in the mushroom Boletopsis leucomelas (PERS.) FAYOD and how they change via cooking

Sakemi, Yuka; Hagiwara, Moe; Oikawa, Aya; Sato, Miho; Sato, Showbu; Sawa, Natsuki; Nishizawa, Hinata; Shindo, Kazutoshi

doi:10.1016/j.foodchem.2021.130281

Cited by 7 publications

(2 citation statements)

References 21 publications

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“…Terpenoids isolated and identified from Sanghuangporus sanghuang could scavenge DPPH and 2,2′-Azinobis-(3ethylbenzthiazoline-6-sulphonate) (ABTS) free radicals; however, their antioxidant activity is significantly inferior to the polysaccharides and phenolic compounds (Zhang et al, 2021). P-terphenyl compounds isolated from mushroom Boletopsis leucomelas through chromatography possess effective DPPH scavenging capacity, which can be enhanced with heating (Sakemi et al, 2021). 2,5-diarylcyclopentenone derivatives from Paxillus involutus possess clearing abilities of DPPH,•OH, and O 2 - (Lv et al, 2021).…”

Section: Proteins Terpenoids Arene and Lipidsmentioning

confidence: 99%

Compounds purified from edible fungi fight against chronic inflammation through oxidative stress regulation

Xia

Wang

et al. 2022

Front. Pharmacol.

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Chronic inflammation is associated with various chronic diseases, including cardiovascular disease, neurodegenerative disease, and cancer, which severely affect the health and quality of life of people. Oxidative stress induced by unbalanced production and elimination of reactive oxygen species (ROS) is one of the essential risk factors for chronic inflammation. Recent studies, including the studies of mushrooms, which have received considerable attention, report that the antioxidant effects of natural compounds have more advantages than synthetic antioxidants. Mushrooms have been consumed by humans as precious nourishment for 3,000 years, and so far, more than 350 types have been identified in China. Mushrooms are rich in polysaccharides, peptides, polyphenols, alkaloids, and terpenoids and are associated with several healthy biological functions, especially antioxidant properties. As such, the extracts purified from mushrooms could activate the expression of antioxidant enzymes through the Keap1/Nrf2/ARE pathway to neutralize excessive ROS and inhibit ROS-induced chronic inflammation through the NF-κB pathway. Recently, the antioxidant properties of mushrooms have been successfully applied to treating cardiovascular disease (CAD), neurodegenerative diseases, diabetes mellitus, and cancer. The present review summarizes the antioxidant properties and the mechanism of compounds purified from mushrooms, emphasizing the oxidative stress regulation of mushrooms to fight against chronic inflammation.

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Section: Proteins Terpenoids Arene and Lipidsmentioning

confidence: 99%

Compounds purified from edible fungi fight against chronic inflammation through oxidative stress regulation

Xia

Wang

et al. 2022

Front. Pharmacol.

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“…Compounds 4 and 5 showed weaker antiproliferative activity with IC50 range of 130-220 µM. For mixture 1 and 2, compound 1 has been reported to show antioxidant (Sakemi et al, 2021), antibacterial (Wossa et al, 2013), 5-lipoxygenase inhibitory , and lipidperoxidation-inhibitory activity while for compound 2, no bioactivity has ever been reported. An earlier study on compound 3 revealed that it possessed 5-lipoxygenase inhibitory , antibacterial (Wossa et al, 2013), antioxidant, and alpha-glucosidase inhibitory activity .…”

Section: Resultsmentioning

confidence: 99%

Synthetic small molecule inhibitors of KRAS expression and antiproliferative small molecules isolated from Onnia tomentosa and Sarcodon scabripes

Lee¹

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Small molecules, including synthetic and those isolated from natural products, are important classes of compounds with broad utility, including drugs. The objectives of this dissertation were (i) to synthesize, purify, and characterize novel small molecule inhibitors on KRAS expression level; (ii) to purify and characterize antiproliferative small molecules from Onnia tomentosa and Sarcodon Scabripes.The first part of this Ph.D. dissertation focuses on synthesizing dispiropyrrolidizine derivatives with potential KRAS protein expression inhibitory activity. At the outset of this study, compound UNBC 152, which turned out to be a mixture of compounds, was found to possess bioactivities including antiproliferative activity and the ability to inhibit KRAS expression. This study aimed to synthesize UNBC 152 and resolve the compound-activity ambiguity. The investigation on UNBC 152 led to the isolation of two novel regioisomers, 6 and 7. Regioisomers 6 and 7 were synthesized using a one-pot three-component 1,3-dipolar cycloaddition reaction.They were purified using recrystallization method and their structures were determined by FTIR, ESI-LRMS, NMR, and X-ray crystallography. Regioisomers 6 and 7 showed the ability to inhibit KRAS protein expression.Over the past several decades, researchers have isolated many useful medicinal compounds from mushrooms. Medicinal mushrooms with validated anticancer properties in animals have been found and this has encouraged further exploration of fungal metabolites with antiproliferative activity. The second part of this Ph.D. dissertation focuses on isolating antiproliferative small molecules from two species of mushrooms native to British Columbia (BC). Chapters 3 and 4 described the use of antiproliferative activity-guided approach that led to the isolation and structural elucidation of small molecules from O. tomentosa and S. scabripes native to Northern iii BC. The ethanolic extracts of O. tomentosa and S. scabripes were purified using phase separation, Sephadex LH-20, and HPLC-based fractionation. The final structure of the small molecules was determined by ESI-LRMS, ESI-HRMS/MS, and NMR. Fatty acids (labeled 1.1-1.4 and 2-7) were identified from the ethanolic extract of O. tomentosa, while several p-terphenyl derivatives (1-4) and one phenolic aldehyde (5) were identified from S. scabripes. Amongst the small molecules, oleic acid (7), linoleic acid (6), and linoleic degradation products from O. tomentosa, and compounds 1-5 from S. scabripes showed antiproliferative activity against HeLa cervical cancer cells. iv PREFACE This Ph.D. dissertation yielded one published manuscript for Chapter 2, while the manuscripts for Chapters 3 and 4 are currently under revision and review, respectively. Publication and authorships from this dissertation were stated as follows (Published or under review):

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Anti-inflammatory and anticancer p-terphenyl derivatives from fungi of the genus Thelephora

Bailly

2022

Bioorganic & Medicinal Chemistry

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Antioxidant p-terphenyl compounds in the mushroom Boletopsis leucomelas (PERS.) FAYOD and how they change via cooking

Cited by 7 publications

References 21 publications

Compounds purified from edible fungi fight against chronic inflammation through oxidative stress regulation

Compounds purified from edible fungi fight against chronic inflammation through oxidative stress regulation

Synthetic small molecule inhibitors of KRAS expression and antiproliferative small molecules isolated from Onnia tomentosa and Sarcodon scabripes

Anti-inflammatory and anticancer p-terphenyl derivatives from fungi of the genus Thelephora

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