Chemical Modification of Pseurotin A: One-pot Synthesis of Synerazol and Pseurotin E and Determination of Absolute Stereochemistry of Pseurotin E

Ishikawa, Minoru; Ninomiya, Tomohisa

doi:10.1038/ja.2008.99

Cited by 24 publications

(7 citation statements)

References 25 publications

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“…18 These compounds possess the same 1-oxa-7-azaspiro [4.4]non-2-ene-4,6-dione core as pseurotins A-E ( 19) isolated from Pseudeurotium ovalis S2269/F, 19 pseurotins F 1 and F 2 (20), 20 and synerazol (21) isolated from Aspergillus fumigatus SANK 10588. 21 The hemisynthesis of synerazol and pseurotin E from pseurotin A has been reported and enabled the determination of the absolute stereochemistry of pseurotin E. 22 FD-838 (22) has been isolated from an Aspergillus strain and features an additional furan ring on the side chain. 23 Spirostaphylotrichin A ( 23) and congeners constitute another group of fungal spiro derivatives with a 6-membered carbocycle, isolated from Staphylotrichum coccosporum 24 and Curvularia pallescens.…”

Section: -Pyrrolidin-2-ones Included In Spirocyclic Systemsmentioning

confidence: 99%

Chemistry and biology of non-tetramic γ-hydroxy-γ-lactams and γ-alkylidene-γ-lactams from natural sources

2009

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Natural products containing non-tetramic gamma-hydroxy-gamma-lactams and gamma-alkylidene-gamma-lactams are usually but not exclusively derived from the mixed polyketide-non-ribosomal peptide biosynthetic pathway. Often they are fungal metabolites, although some plant- and marine-derived exceptions exist. Owing to their unique structures and biological properties, they have gained interest in the chemical and biological communities. In this review, we aim to emphasize the structural originality of these compounds, their biological properties and the synthetic efforts developed to reach them; 157 references are cited.

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Section: -Pyrrolidin-2-ones Included In Spirocyclic Systemsmentioning

confidence: 99%

Chemistry and biology of non-tetramic γ-hydroxy-γ-lactams and γ-alkylidene-γ-lactams from natural sources

2009

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“…Small organic molecules isolated from fungi represent highly attractive compounds that have the potential for the modulation of specific physiological processes by affecting individual cellular pathways. A particularly interesting group of such fungal secondary metabolites is pseurotins, ergot-like alkaloids containing a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione core, that comprise a family with over twenty-five members such as azaspirene and synerazol [ 1 , 2 , 3 , 4 ]. Pseurotin A, the first described member, was isolated in 1976 from the fermentation broth of Pseudeurotium ovalis Stolk (Ascomycetes) by Bloch [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

Pseurotin D Inhibits the Activation of Human Lymphocytes

Rubanova

Daďová

Vašíček

et al. 2021

IJMS

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Background: Pseurotins, a family of secondary metabolites of different fungi characterized by an unusual spirocyclic furanone-lactam core, are suggested to have different biological activities including the modulation of immune response. Purpose: Complex characterization of the effects of pseurotin D on human lymphocyte activation in order to understand the potential of pseurotin to modulate immune response in humans. Methods: CD4+ and CD8+ T cells and CD19+ B cells isolated from human blood were activated by various activators simultaneously with pseurotin D treatment. The effects of pseurotin were tested on the basis of changes in cell viability, apoptosis, activation of signal transducers and activators of transcription (STAT) signaling pathways, production of tumor necrosis factor (TNF)-α by T cells, expression of activation markers CD69 and CD25 on T cells and Human Leukocyte Antigen–DR isotype (HLA-DR) on B cells, and the differentiation markers CD20, CD27, CD38, and immunoglobulin (Ig) D on B cells. Results: Pseurotin D significantly inhibited the activation of both CD4+ and CD8+ human T cells complemented by the inhibition of TNF-α production without significant acute toxic effects. The Pseurotin D-mediated inhibition of T-cell activation was accompanied by the induction of the apoptosis of T cells. This corresponded with the inhibited phosphorylation of STAT3 and STAT5. In human B cells, pseurotin D did not significantly inhibit their activation; however, it affected their differentiation. Conclusions: Our results advance the current mechanistic understanding of the pseurotin-induced inhibition of lymphocytes and suggest pseurotins as new attractive chemotypes for future research in the context of immune-modulatory drugs.

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“…74 and synerazol (137). 53 The known compounds obtained from fermentation or precursor-directed biosynthesis were 12,13-dihydropseurotin A (209), 49,50 12,13-dibromopseurotin A (210), 46 10,11-acetonide 211, 46 aldehyde 212, 46,49 (10R,11S)-diastereomer of synerazol 208, 76 triacetylpseurotin A (214), 46 tetraacetylpseurotin A (215), 46 17-dihydropseurotin A (216), 50 and fluorinated pseurotin A (217, 218) (Figure 3). 40 Other compounds were prepared by synthetic derivatization of pseurotin A (134) from fermentation (Scheme 20).…”

Section: -3 Misaki and Tanabe's Total Synthesis Of Azaspirenementioning

confidence: 99%

Highly Oxidized γ-Lactam-Containing Natural Products: Total Synthesis and Biological Evaluation

Kobayashi¹,

Tanaka²,

Kogen³

2021

HETEROCYCLES

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γ-Lactam is a ubiquitous structure found in the natural products. A number of highly oxidized γ-lactam-containing natural products are produced by various fungi. These compounds often show a wide range of biological activities because their multiple internal reaction sites, which arise from the high oxidation state of the compounds, can react with biological nucleophiles. Due to their high reactivity and dense functionality, total syntheses of these molecules require strict control of the inherent reactivity and the appropriate design of synthetic intermediates. This review focuses on the recent total syntheses of some highly oxidized γ-lactam-containing natural products, including fused bicyclic (epolactaene, NG-391, lucilactaene, L-755,807), spirocyclic (azaspirene, pseurotin A, E, and F2, cephalimysin A-C, FD-838, and berkeleyamide D), and tricyclic (rubrobramide and talaramide A) skeletons, and on the structure-activity relationship studies of related molecules.

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Chemical Modification of Pseurotin A: One-pot Synthesis of Synerazol and Pseurotin E and Determination of Absolute Stereochemistry of Pseurotin E

Cited by 24 publications

References 25 publications

Chemistry and biology of non-tetramic γ-hydroxy-γ-lactams and γ-alkylidene-γ-lactams from natural sources

Chemistry and biology of non-tetramic γ-hydroxy-γ-lactams and γ-alkylidene-γ-lactams from natural sources

Pseurotin D Inhibits the Activation of Human Lymphocytes

Highly Oxidized γ-Lactam-Containing Natural Products: Total Synthesis and Biological Evaluation

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