10-Methoxydihydrofuscin, Fuscinarin, and Fuscin, Novel Antagonists of the Human CCR5 Receptor from Oidiodendron griseum

Yoganathan, K.; Rossant, Christine; Ng, Siewbee; Huang, Yunsong; Butler, Mark S.; Buss, Antony D.

doi:10.1021/np030146m

Cited by 89 publications

(56 citation statements)

References 9 publications

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“…1 The isolation of fuscin (2) has also been reported by other researchers before. 2 The molecular structure of fuscin (2) was characterized by comparing its 1 H NMR and MS data with those in the literature, 2c,2d but the absolute stereochemistry and the specific rotation are still unknown. However, unlike fuscin, dihydrofuscin (4), a biosynthesis precursor of fuscin was first isolated from the fungus Potebniamyces gallicola as a natural product in 1983.…”

Section: Introductionsupporting

confidence: 64%

“…The novel pentaketide metabolites, fuscinarin (1) and two known pentaketide metabolites, fuscin (2) and 10-methoxydihydrofuscin (3), have been isolated recently from the fungus Oidiodendron griseum (a mitosporic fungus) ( Figure 1). 1 The isolation of fuscin (2) has also been reported by other researchers before.…”

Section: Introductionmentioning

confidence: 99%

“…1 The physiologically active mold metabolite fuscin has attracted much attention, and a number of synthetic approaches have been reported. 2b,3 Syntheses of 10-methoxydihydrofuscin (3) and dihydrofuscin (4) have appeared in the literature in 1955.…”

Section: Introductionmentioning

confidence: 99%

“…As a result of their interesting structural and biological properties, these pentaketide metabolites have received considerable interest from the pharmic community. 4 In this report we describe a versatile approach for the first total synthesis of fuscinarin (1) and total synthesis of fuscins from the commercially available starting material, gallacetophenone 9. (1), fuscin (2), 10-methoxydihydrofuscin (3), and dihydrofuscin (4).…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

A Versatile Approach for the Total Syntheses of Fuscinarin and Fuscins

Du¹,

Li²,

Da³

et al. 2008

Chin. J. Chem.

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Section: Introductionsupporting

confidence: 64%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

A Versatile Approach for the Total Syntheses of Fuscinarin and Fuscins

Du¹,

Li²,

Da³

et al. 2008

Chin. J. Chem.

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“…However, preliminary results showed that various concentrations of ␤-D-glucan did not induce eosinophil degranulation or superoxide production in vitro (data not shown). Finally, certain microorganisms, such as HIV and fungi, might directly interact with or produce a molecule(s) that binds to a cell's chemokine receptors (e.g., CCR5), which are coupled to certain G proteins (56,57). Additional studies are needed to identify the stimulatory component(s) in Alternaria extract and its receptor(s) on eosinophils.…”

Section: Discussionmentioning

confidence: 99%

Nonpathogenic, Environmental Fungi Induce Activation and Degranulation of Human Eosinophils

Inoue¹,

Matsuwaki²,

Shin³

et al. 2005

The Journal of Immunology

143

123

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Eosinophils and their products are probably important in the pathophysiology of allergic diseases, such as bronchial asthma, and in host immunity to certain organisms. An association between environmental fungal exposure and asthma has been long recognized clinically. Although products of microorganisms (e.g., lipopolysaccharides) directly activate certain inflammatory cells (e.g., macrophages), the mechanism(s) that triggers eosinophil degranulation is unknown. In this study we investigated whether human eosinophils have an innate immune response to certain fungal organisms. We incubated human eosinophils with extracts from seven environmental airborne fungi (Alternaria alternata, Aspergillus versicolor, Bipolaris sorokiniana, Candida albicans, Cladosporium herbarum, Curvularia spicifera, and Penicillium notatum). Alternaria and Penicillium induced calcium-dependent exocytosis (e.g., eosinophil-derived neurotoxin release) in eosinophils from normal individuals. Alternaria also strongly induced other activation events in eosinophils, including increases in intracellular calcium concentration, cell surface expression of CD63 and CD11b, and production of IL-8. Other fungi did not induce eosinophil degranulation, and Alternaria did not induce neutrophil activation, suggesting specificity for fungal species and cell type. The Alternaria-induced eosinophil degranulation was pertussis toxin sensitive and desensitized by preincubating cells with G protein-coupled receptor agonists, platelet-activating factor, or FMLP. The eosinophil-stimulating activity in Alternaria extract was highly heat labile and had an Mr of ∼60 kDa. Thus, eosinophils, but not neutrophils, possess G protein-dependent cellular activation machinery that directly responds to an Alternaria protein product(s). This innate response by eosinophils to certain environmental fungi may be important in host defense and in the exacerbation of inflammation in asthma and allergic diseases.

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Pd‐Catalyzed Benzylic CH Functionalization

Thorat¹,

Jain²,

Parganiha³

et al. 2022

Handbook of CH-Functionalization

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Palladium‐catalyzed benzylic CH functionalization has enormous application in industry and academia. Conventional methods have limited scope and selectivity toward functionalization attributed to the very high reactivity of benzylic position particularly benzylic anion. This article discusses the current development of palladium‐catalyzed benzylic CH functionalization involving CC, CO, CN, and CF bond formation which not only tame the reactivity of benzylic anion but also enables its reaction with a large variety of substrates. Some of the applications such as construction of biologically, pharmaceutically, and agrochemical relevant organic molecules have been discussed. This article summarizes palladium‐catalyzed benzylic CH functionalization in a comprehensive way.

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10-Methoxydihydrofuscin, Fuscinarin, and Fuscin, Novel Antagonists of the Human CCR5 Receptor from Oidiodendron griseum

Cited by 89 publications

References 9 publications

A Versatile Approach for the Total Syntheses of Fuscinarin and Fuscins

A Versatile Approach for the Total Syntheses of Fuscinarin and Fuscins

Nonpathogenic, Environmental Fungi Induce Activation and Degranulation of Human Eosinophils

Pd‐Catalyzed Benzylic CH Functionalization

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