Anticancer Activities of Thelephantin O and Vialinin A Isolated from Thelephora aurantiotincta

Norikura, Toshio; Fujiwara, Kenshu; Narita, Takanobu; Yamaguchi, Shinya; Morinaga, Yae; Iwai, Kunihisa; Matsue, Hiroyuki

doi:10.1021/jf200461j

Cited by 47 publications

(21 citation statements)

References 18 publications

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“…Vialinin A, commonly found in many edible mushroom species, through its antioxidant potential exerts anticarcinogenic effects [ 32 ]. In this study, our results demonstrate a novel antiangiogenic activity of vialinin A in vitro and in vivo.…”

Section: Discussionmentioning

confidence: 99%

Vialinin A, an Edible Mushroom‐Derived p‐Terphenyl Antioxidant, Prevents VEGF‐Induced Neovascularization In Vitro and In Vivo

Sonowal

Shukla

Kota

et al. 2018

Oxidative Medicine and Cellular Longevity

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Increased side toxicities and development of drug resistance are the major concern for the cancer chemotherapy using synthetic drugs. Therefore, identification of novel natural antioxidants with potential therapeutic efficacies is important. In the present study, we have examined how the antioxidant and anti-inflammatory activities of vialinin A, a p-terphenyl compound derived from Chinese edible mushroom T. terrestris and T. vialis, prevents human umbilical vascular endothelial cell (HUVEC) neovascularization in vitro and in vivo models. Pretreatment of HUVECs with vialinin A prevents vascular endothelial growth factor- (VEGF) induced HUVEC cell growth in a dose-dependent manner. Further, vialinin A also inhibits VEGF-induced migration as well as tube formation of HUVECs. Treatment of HUVECs prevents VEGF-induced generation of reactive oxygen species (ROS) and malondialdehyde (MDA) and also inhibits VEGF-induced NF-κB nuclear translocation as well as DNA-binding activity. The VEGF-induced release of various angiogenic cytokines and chemokines in HUVECs was also significantly blunted by vialinin A. Most importantly, in a mouse model of Matrigel plug assay, vialinin A prevents the formation of new blood vessels and the expression of CD31 and vWF. Thus, our results indicate a novel role of vialinin A in the prevention of neovascularization and suggest that anticancer effects of vialinin A could be mediated through its potent antioxidant and antiangiogenic properties.

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Section: Discussionmentioning

confidence: 99%

Vialinin A, an Edible Mushroom‐Derived p‐Terphenyl Antioxidant, Prevents VEGF‐Induced Neovascularization In Vitro and In Vivo

Sonowal

Shukla

Kota

et al. 2018

Oxidative Medicine and Cellular Longevity

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“…[1,2] p-Terphenyls cored with electron-withdrawing and electron-rich functionalities are mainly found in mushrooms of family Thelephoraceae [3,4,5,6,7] and Paxillaceae. [8] Various p-terphenyl-cored biologically active natural products such as thelephorin, [9] thelephantin, [10,11] vialinin, [12] aurantiotinin, [13] butlerin, [14,15] corticin [16] and polyozellin [17] have been isolated from different species of edible and inedible mushrooms. Various synthetic p-terphenyls have been prepared that exhibit different biological activities such as antibiotic, [18] antidiabetic, [19,20,21] antioxidant [22] and cancer cell-selective antiproliferative activity.…”

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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“…These compounds exhibit a broad range of biological properties, including antimicrobial, immuno-suppressant, neuro-protective, 5-lipoxygenase inhibitory, anti-coagulant and antithrombotic activities (5,(12)(13)(14)(15). In addition, different chemo-protective, cytotoxic and anti-proliferative effects have been documented with a variety of transformed or cancerous cell lines, such as HeLa, HepG2, HCT116 or Caco2 cells in culture (16,17). As such, p-terphenyl derivatives are attractive targets for medicinal chemists in the search for new therapeutic drug leads.…”

Section: Introductionmentioning

confidence: 99%

Flow reactor synthesis of unsymmetrically substitutedp-terphenyls using sequentially selective Suzuki cross-coupling protocols

Kazi

Campi

Hearn

2019

Green Chemistry Letters and Reviews

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Synthetic procedures, based on integrated flow chemical methods, have been developed for the sequential chemo-selective Suzuki-Miyaura cross-coupling of 1,4-dibromo-2-nitrobenzene (1) with various arylboronic acids. The first Suzuki coupling step used a phosphine-(ligand)-free palladium catalyst at room temperature and gave regio-selective coupling of (1) at the orthoposition to the nitro group. The bromo-biaryl product was then directly subjected in situ to a second coupling step, using different arylboronic acids, as a continuous in-flow operation. Based on this methodology, a number of unsymmetrically substituted p-terphenyl compounds were synthesized in excellent overall yields. This approach provides a convenient route to this class of compounds, and is suited for the generation of targeted chemical libraries, or the synthesis of precursors of biologically active natural product analogues that contain the p-terphenyl core. During the first coupling step, dimerization at low levels of the bromo-biaryl intermediate occurred, leading to formation of quaterphenyl compounds.

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Anticancer Activities of Thelephantin O and Vialinin A Isolated from Thelephora aurantiotincta

Cited by 47 publications

References 18 publications

Vialinin A, an Edible Mushroom‐Derived p‐Terphenyl Antioxidant, Prevents VEGF‐Induced Neovascularization In Vitro and In Vivo

Vialinin A, an Edible Mushroom‐Derived p‐Terphenyl Antioxidant, Prevents VEGF‐Induced Neovascularization In Vitro and In Vivo

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

Flow reactor synthesis of unsymmetrically substitutedp-terphenyls using sequentially selective Suzuki cross-coupling protocols

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