Synthesis of polyozellin, a prolyl oligopeptidase inhibitor, and its structural revision

Takahashi, Shigetoshi; Kawano, Tsuyoshi; Nakajima, Natsumi; Suda, Yasuaki; Usukhbayar, Narandulam; Kimura, Ken‐ichi; Koshino, Hiroyuki

doi:10.1016/j.bmcl.2018.01.054

Cited by 9 publications

(5 citation statements)

References 47 publications

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“…A new inhibitor of prolyl endopeptidase (PEP) with an IC 50 value of 2.72 µM, named polyozellin, was identified from a methanolic extract of fresh fruiting bodies collected in Korea [176]. The total synthesis of polyozellin by Takahashi and his collaborators led to a revision of the structure which was determined to be 75 [177]. A Korean research group investigated the EtOAc soluble fraction of the mushroom and reported the chemical structure of two active compounds, thelephoric acid (76) and kynapcin-9 (77) with their PEP activities [178].…”

Section: Polyozellus Multiplex (Underw) Murrillmentioning

confidence: 99%

“…Polyozellin (75) and extract [189] Extract [188] Polyozellin (75) [179,190]. Extract [187,190] Polyozellin (75) (prolyl endopeptidase (PEP) inhibitory activity [176,177], β-secretase (BACE1) inhibitory activities [175], neuroprotective effect [187] and anti-inflammatory activities [189][190][191][192][193][194][195]). Thelephoric acid (76) (PEP inhibitory activity [178], β-secretase (BACE1) inhibitory activity [175] and neuroprotective effect [175]).…”

Section: Thelephora Ganbajun M Zangmentioning

confidence: 99%

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Bioactive Phytochemical Constituents of Wild Edible Mushrooms from Southeast Asia

et al. 2020

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Mushrooms have a long history of uses for their medicinal and nutritional properties. They have been consumed by people for thousands of years. Edible mushrooms are collected in the wild or cultivated worldwide. Recently, mushroom extracts and their secondary metabolites have acquired considerable attention due to their biological effects, which include antioxidant, antimicrobial, anti-cancer, anti-inflammatory, anti-obesity, and immunomodulatory activities. Thus, in addition to phytochemists, nutritionists and consumers are now deeply interested in the phytochemical constituents of mushrooms, which provide beneficial effects to humans in terms of health promotion and reduction of disease-related risks. In recent years, scientific reports on the nutritional, phytochemical and pharmacological properties of mushroom have been overwhelming. However, the bioactive compounds and biological properties of wild edible mushrooms growing in Southeast Asian countries have been rarely described. In this review, the bioactive compounds isolated from 25 selected wild edible mushrooms growing in Southeast Asia have been reviewed, together with their biological activities. Phytoconstituents with antioxidant and antimicrobial activities have been highlighted. Several evidences indicate that mushrooms are good sources for natural antioxidants and antimicrobial agents

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Section: Polyozellus Multiplex (Underw) Murrillmentioning

confidence: 99%

Section: Thelephora Ganbajun M Zangmentioning

confidence: 99%

Bioactive Phytochemical Constituents of Wild Edible Mushrooms from Southeast Asia

et al. 2020

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“…[33] In 2018, Takahashi and coworkers reported the synthesis naturally occurring p-terphenyl (polyozellin) in five chemical steps in including Pd-catalyzed Suzuki-Miyaura crosscoupling reaction. [34] Mandali and Chand have used palladium nanoparticles as catalyst to develop the Suzuki-Miyaura coupling for the synthesis of p-terphenyl. [35] Additionally, the immobilized palladium nanoparticles on silica-starch substrate (PNP-SSS) have been also used in Suzuki-Miyaura reaction to achieve the similar scaffolds.…”

Section: Introductionmentioning

confidence: 99%

“…In 2013, Wang and others developed the synthesis of p ‐terphenyls by Pd‐catalyzed Stille cross‐coupling of boron and tin‐cored substrates with aryl bromide followed by Pd‐catalyzed Suzuki‐Miyaura cross‐coupling of earlier coupling product with aryl bromide . In 2018, Takahashi and coworkers reported the synthesis naturally occurring p ‐terphenyl (polyozellin) in five chemical steps in including Pd‐catalyzed Suzuki‐Miyaura cross‐coupling reaction . Mandali and Chand have used palladium nanoparticles as catalyst to develop the Suzuki‐Miyaura coupling for the synthesis of p ‐terphenyl .…”

Section: Introductionmentioning

confidence: 99%

Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

Chandrasekar

Singh

2020

ChemistrySelect

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A metal-free approach for the synthesis of p-terphenyls 7 a-i and cyclic p-terphenyls 9 ad and 11 ad is described via carbanion induced ring transformation reaction of 6-biphenyl-2H-pyran-2-ones 5 with malononitrile 6, cyclohexanone 8 and 1,4-cyclohexanedione monoethylene ketal 10 respectively. Additionally, the base-mediated ring transformation reactions were working smoothly under mild reaction conditions and ring transformation products 7, 9 and 11 were isolated in good to excellent yields. The synthetic approach provides the flexibility of introducing of both electron-withdrawing and-donating functionalities in p-terphenyl architecture. Moreover, the photo physical properties of compounds 7, 9 and 11 were analyzed using UV-visible and Fluorescence Spectroscopy. p-Terphenyls 7 c showed cyan fluorescence in chloroform (λ max (em): 508 nm) and acetonitrile (λ max (em): 420 nm) while cyclic p-terphenyl 9 a showed blue fluorescence in chloroform and 1,4-dioxane (λ max (em): 470 nm). Similarly, compound 11 a showed blue fluorescence in chloroform (λ max (em): 468 nm) and 1,4-dioxane (λ max (em): 473 nm). Additionally, the thermal stability of synthesized cyclic p-terphenyls 11 a, 11 c and 11 d were also studied using TG and DTA techniques.

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“…(1), 22,23 kynapcin-12 (2), 19,24 NSC617425 (3), 25 cycloleucomelone (4), 26 Bl-V (5), 27 succinic acid (6), 28 and protocatechuic acid (7) 28 (Figures , 1, S2, S3). This is the first report on the isolation of compounds 4-7 from P. multiplex.…”

mentioning

confidence: 99%

Inhibition of Amyloid-β Aggregation by p-Terphenyls from the Mushroom Polyozellus multiplex and Their Neuroprotective Effects

Kinoshita¹,

Nakabayashi²,

Ishikura³

et al. 2022

HETEROCYCLES

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The main pathogenesis of Alzheimer's disease (AD) is related to the accumulation of amyloid-b (Ab) peptides in the brain that leads to neuronal cell death. In this study, we identified compounds in a methanol extract of the fruiting body of Polyozellus multiplex that inhibited Ab aggregation and are neuroprotective.Seven compounds against Ab40 aggregation were obtained through bioactivityguided fractionation of the extract, including polyozellin (1), kynapcin-12 (2), NSC617425 (3), cycloleucomelone (4), Bl-V (5), succinic acid (6), and protocatechuic acid (7). Compounds 1-5 inhibited Ab40 aggregation in a dosedependent manner. Moreover, compounds 2-5 protected SH-SY5Y cells from Ab toxicity. Therefore, these compounds are potential agents in AD treatment.Dementia is a neurodegenerative disease caused by acquired organic brain damage. The disease is characterized by a persistent loss of cognitive function that interferes with daily and social life. Alzheimer's disease (AD) is the most frequent cause of dementia 1 ; its pathological features include neuronal loss (mainly in the cerebral cortex), neurofibrillary tangles, and the occurrence of senile plaques in the brain parenchyma.Senile plaques are composed of amyloid-b (Ab) peptides. 2 Normally, Ab peptides are degraded and/or eliminated. However, excessive accumulation of Ab forms senile plaques, eventually leading to AD, which is known as the amyloid cascade hypothesis. 3 Ab is a partial fragment of amyloid precursor protein (APP), which is produced by the cleavage of b-secretase 1 (BACE1) and γ-secretase and is subsequently secreted into the extracellular milieu. [4][5][6] Ab undergoes degradation by various extracellular pathways. Therefore, 2025

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Synthesis of polyozellin, a prolyl oligopeptidase inhibitor, and its structural revision

Cited by 9 publications

References 47 publications

Bioactive Phytochemical Constituents of Wild Edible Mushrooms from Southeast Asia

Bioactive Phytochemical Constituents of Wild Edible Mushrooms from Southeast Asia

Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

Inhibition of Amyloid-β Aggregation by p-Terphenyls from the Mushroom Polyozellus multiplex and Their Neuroprotective Effects

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