Structure elucidation of xanthone derivatives with CD4-binding activity from Penicillium glabrum (Wehmer) Westling

Wrigley, Stephen K.; Latif, Marwa Abdel; Gibson, Trevor; Chicarelli-Robinson, M. I.; Williams, D. H.

doi:10.1351/pac199466102383

Cited by 19 publications

(12 citation statements)

References 6 publications

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“…In agreement with our proposal, heating 5,6-dehydropolivione (6) in deionized water to 55 8C provided vinaxanthone (2) in 61 % yield (Scheme 5). Thus, vinaxanthone was synthesized in nine steps from tetronic acid, whereas the previous synthesis required 14 steps to provide the natural product.…”

supporting

confidence: 90%

“…The isolation and structural characterization data of the natural products xanthofulvin (1) and 411J (3) reveal the structures show nearly identical spectral properties (Scheme 2). [6] In addition, the keto form 4 of xanthofulvin and the keto form 5 of 411J also possess overlapping spectral properties. [7] This observation led us to the conclusion that the assignments for xanthofulvin and 411J were based on the same natural product.…”

mentioning

confidence: 99%

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Syntheses of Xanthofulvin and Vinaxanthone, Natural Products Enabling Spinal Cord Regeneration

et al. 2012

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Growth promoting: The first synthesis of the natural product xanthofulvin (SM‐216289) has resolved issues regarding its structural assignment and that described for the natural product 411J. The structurally and biologically related natural product vinaxanthone was similarly prepared through a novel dimerization reaction. Treatment of C. elegans with synthetic xanthofulvin and vinaxanthone enhanced axonal branching.

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supporting

confidence: 90%

mentioning

confidence: 99%

Syntheses of Xanthofulvin and Vinaxanthone, Natural Products Enabling Spinal Cord Regeneration

et al. 2012

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“…In particular, mushrooms are known to produce a variety of styrylpyrones and their biological effects, including anti-oxidative, anti-cancer, anti-platelet, anti-diabetic, anti-inflammatory, and anti-viral activities, have been shown [42]. Anhydrofulvic acid ( 2 ) and citromycetin ( 3 ) are members of an under-represented structural class that forms via a single linear heptaketide, and their weak CD4-binding activity has been previously reported [43]. In addition, the anti-fungal activity of anhydrofulvic acid and its mode of action have been previously investigated [28], and citromycetin has been patented for the treatment of neurodegenerative diseases such as Alzheimer’s, Lewy body, and Parkinson’s disease [29].…”

Section: Discussionmentioning

confidence: 99%

PTP1B Inhibitory and Anti-Inflammatory Effects of Secondary Metabolites Isolated from the Marine-Derived Fungus Penicillium sp. JF-55

Lee

Jang

et al. 2013

Marine Drugs

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Protein tyrosine phosphatase 1B (PTP1B) plays a major role in the negative regulation of insulin signaling, and is thus considered as an attractive therapeutic target for the treatment of diabetes. Bioassay-guided investigation of the methylethylketone extract of marine-derived fungus Penicillium sp. JF-55 cultures afforded a new PTP1B inhibitory styrylpyrone-type metabolite named penstyrylpyrone (1), and two known metabolites, anhydrofulvic acid (2) and citromycetin (3). Compounds 1 and 2 inhibited PTP1B activity in a dose-dependent manner, and kinetic analyses of PTP1B inhibition suggested that these compounds inhibited PTP1B activity in a competitive manner. In an effort to gain more biological potential of the isolated compounds, the anti-inflammatory effects of compounds 1–3 were also evaluated. Among the tested compounds, only compound 1 inhibited the production of NO and PGE2, due to the inhibition of the expression of iNOS and COX-2. Penstyrylpyrone (1) also reduced TNF-α and IL-1β production, and these anti-inflammatory effects were shown to be correlated with the suppression of the phosphorylation and degradation of IκB-α, NF-κB nuclear translocation, and NF-κB DNA binding activity. In addition, using inhibitor tin protoporphyrin (SnPP), an inhibitor of HO-1, it was verified that the inhibitory effects of penstyrylpyrone (1) on the pro-inflammatory mediators and NF-κB DNA binding activity were associated with the HO-1 expression. Therefore, these results suggest that penstyrylpyrone (1) suppresses PTP1B activity, as well as the production of pro-inflammatory mediators via NF-κB pathway, through expression of anti-inflammatory HO-1.

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“…Structurally related to chaetocyclinone C (5) is vinaxanthone [9] (6), first isolated in 1991 by Aoki et al from Penicil- lium vinaceum as a phospholipase C inhibitor. [9] Additionally, 6 exhibits a potent CD4-binding activity, [10] touching the Achilles' heel of HIV.…”

Section: Structure Elucidationmentioning

confidence: 99%

Structure and Biosynthesis of Chaetocyclinones, New Polyketides Produced by an Endosymbiotic Fungus

et al. 2007

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Three new fungal polyketide metabolites, chaetocyclinone A to C, were produced by cultures of Chaetomium sp. (strain Gö 100/2), which was isolated from marine algae. The structures of the novel compounds were established by detailed spectroscopic analysis. Additionally, an X‐ray analysis of chaetocyclinone C (5) was performed. Chaetocyclinone A (1) exhibits inhibitory activity against selected phytopathogenic fungi. The biosynthesis of 1 and 5 was studied by feeding 13C‐labelled acetate. The results suggest the polyketide pathway for the isolated metabolites. In the case of chaetocyclinone C (5), we assume an unusual condensation of two highly reactive heptaketide intermediates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Structure elucidation of xanthone derivatives with CD4-binding activity from Penicillium glabrum (Wehmer) Westling

Abstract: Abstract

Cited by 19 publications

References 6 publications

Syntheses of Xanthofulvin and Vinaxanthone, Natural Products Enabling Spinal Cord Regeneration

Syntheses of Xanthofulvin and Vinaxanthone, Natural Products Enabling Spinal Cord Regeneration

PTP1B Inhibitory and Anti-Inflammatory Effects of Secondary Metabolites Isolated from the Marine-Derived Fungus Penicillium sp. JF-55

Structure and Biosynthesis of Chaetocyclinones, New Polyketides Produced by an Endosymbiotic Fungus

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