The broad spectrum 2-oxoglutarate oxygenase inhibitor N-oxalylglycine is present in rhubarb and spinach leaves

Al-Qahtani, Khalid; Jabeen, Bushra; Sekirnik, Rok; Riaz, Naheed; Claridge, Timothy D. W.; Schofield, Christopher J.; McCullagh, James

doi:10.1016/j.phytochem.2015.06.028

Cited by 20 publications

(16 citation statements)

References 22 publications

(29 reference statements)

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“…2OG-competition for binding the AspH active site ( e.g. N -oxalylglycine, 28 , 36 , 86 pyridine-2,3-dicarboxylic acid 21. , 87 ) and Fe(II)-chelation ( e.g.…”

Section: Discussionmentioning

confidence: 99%

Small-molecule active pharmaceutical ingredients of approved cancer therapeutics inhibit human aspartate/asparagine-β-hydroxylase

Brewitz

Tumber

Zhang

et al. 2020

Bioorganic & Medicinal Chemistry

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“…2OG-competition for binding the AspH active site ( e.g. N -oxalylglycine, 28 , 36 , 86 pyridine-2,3-dicarboxylic acid 21. , 87 ) and Fe(II)-chelation ( e.g.…”

Section: Discussionmentioning

confidence: 99%

Small-molecule active pharmaceutical ingredients of approved cancer therapeutics inhibit human aspartate/asparagine-β-hydroxylase

Brewitz

Tumber

Zhang

et al. 2020

Bioorganic & Medicinal Chemistry

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“…5B). The assay reveals that N-oxalylglycine (NOG), a plant metabolite and 2OG isostere, 18 inhibits the PHD2/probe 12 interaction with an IC 50 of 2.52 AE 0.6 mM. This value is similar to the IC 50 (3 AE 1 mM) determined by an NMR binding assay, 9 though lower than that obtained by MS based turnover assay (IC 50 of 18.5 mM).…”

mentioning

confidence: 52%

A small-molecule probe for monitoring binding to prolyl hydroxylase domain 2 by fluorescence polarisation

Zhen

et al. 2020

Chem. Commun.

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“…Natural PPAPs are usually isolated from Garcinia (Clusiaceae) and Hypericum (Hypericaceae) genera [26]. For the present study, PPAPs exhibiting a similar molecular scaffold to guttiferone J (1) were required.…”

Section: Phytochemical Analysismentioning

confidence: 99%

Targeting MHC Regulation Using Polycyclic Polyprenylated Acylphloroglucinols Isolated from Garcinia bancana

et al. 2020

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Modulation of major histocompatibility complex (MHC) expression using drugs has been proposed to control immunity. Phytochemical investigations on Garcinia species have allowed the isolation of bioactive compounds such as polycyclic polyprenylated acylphloroglucinols (PPAPs). PPAPs such as guttiferone J (1), display anti-inflammatory and immunoregulatory activities while garcinol (4) is a histone acetyltransferases (HAT) p300 inhibitor. This study reports on the isolation, identification and biological characterization of two other PPAPs, i.e., xanthochymol (2) and guttiferone F (3) from Garcinia bancana, sharing structural analogy with guttiferone J (1) and garcinol (4). We show that PPAPs 1–4 efficiently downregulated the expression of several MHC molecules (HLA-class I, -class II, MICA/B and HLA-E) at the surface of human primary endothelial cells upon inflammation. Mechanistically, PPAPs 1–4 reduce MHC proteins by decreasing the expression and phosphorylation of the transcription factor STAT1 involved in MHC upregulation mediated by IFN-γ. Loss of STAT1 activity results from inhibition of HAT CBP/p300 activity reflected by a hypoacetylation state. The binding interactions to p300 were confirmed through molecular docking. Loss of STAT1 impairs the expression of CIITA and GATA2 but also TAP1 and Tapasin required for peptide loading and transport of MHC. Overall, we identified new PPAPs issued from Garcinia bancana with potential immunoregulatory properties.

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The broad spectrum 2-oxoglutarate oxygenase inhibitor N-oxalylglycine is present in rhubarb and spinach leaves

Cited by 20 publications

References 22 publications

Small-molecule active pharmaceutical ingredients of approved cancer therapeutics inhibit human aspartate/asparagine-β-hydroxylase

Small-molecule active pharmaceutical ingredients of approved cancer therapeutics inhibit human aspartate/asparagine-β-hydroxylase

A small-molecule probe for monitoring binding to prolyl hydroxylase domain 2 by fluorescence polarisation

Targeting MHC Regulation Using Polycyclic Polyprenylated Acylphloroglucinols Isolated from Garcinia bancana

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