Pigments of fungi (macromycetes)

Gill, Melvyn

doi:10.1039/np9941100067

Cited by 68 publications

(65 citation statements)

References 11 publications

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“…However, in the spectra of 5,5'-(atrovirin), 2 5,10'-(pseudophlegmacin), 17 7,10'-(phlegmacin) 18 and 10,10'-(tricolorin) 19 dimers, in which the C 4 methylene protons are in the zone of influence of the adjacent biaryl ring system, differential shielding can be translated in streochemical terms. 20 The method is particularly effective in those cases where more than one diastereoisomer of a biaryl system is known as a natural product.…”

Section: Introductionmentioning

confidence: 99%

Absolute stereochemistry of fungal metabolites: icterinoidins A1 and B1, and atrovirins B1 and B2

Gill

Morgan²

2004

Arkivoc

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Section: Introductionmentioning

confidence: 99%

Absolute stereochemistry of fungal metabolites: icterinoidins A1 and B1, and atrovirins B1 and B2

Gill

Morgan²

2004

Arkivoc

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“…1). [20][21][22] Effects of atromentic acid (1), variegatic acid (2), and xerocomic acid (3) on CYP3A4 activity Atromentic acid (1), variegatic acid (2), and xerocomic acid (3) inhibited CYP3A4 enzyme activity in vitro. All three compounds showed dose-dependent inhibitory effects on CYP3A4 activity (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…1). [20][21][22] CYP3A4 plays a pivotal role in oxidative drug metabolism. The three compounds, atromentic acid (1), variegatic acid (2), and xerocomic acid (3), inactivated CYP3A4 in a dose-dependent manner, by oxidative metabolism from BOMCC (non-fluorescent) to CHC (highly fluorescent) ( Table 1 and Fig.…”

Section: Discussionmentioning

confidence: 99%

In VitroInhibitory Effects of Pulvinic Acid Derivatives Isolated from Chinese Edible Mushrooms,Boletus calopusandSuillus bovinus, on Cytochrome P450 Activity

Huang¹,

Onose²,

Abe³

et al. 2009

Bioscience, Biotechnology, and Biochemistry

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Increasing attention has been focused on food-drug interactions. We have investigated the inhibitory effect of Chinese edible mushrooms, Boletus calopus and Suillus bovinus, on cytochrome P450 (CYP) 1A2, 2C9, 2D6, and 3A4, the main drug-metabolizing enzymes. Three pulvinic acid derivatives, atromentic acid (1), variegatic acid (2), and xerocomic acid (3), isolated from Boletus calopus and Suillus bovinus, revealed nonspecific inhibitory effects on all four CYPs. Using these compounds, the maximum IC50 values obtained with CYP3A4 in vitro were atromentic acid (1), 65.1+/-3.9 microM; variegatic acid (2), 2.2+/-0.1 microM; and xerocomic acid (3), 2.4+/-0.1 microM. Variegatic acid (2) and xerocomic acid (3) were effective inhibitors, comparable to cimetidine, dicoumarol, erythromycin, safrole, and uniconazole. Variegatic acid (2) and xerocomic acid (3) efficiently reduced ferryl myoglobin in CYPs. Reduction of ferryl heme to ferric heme is likely the mechanism of the nonspecific inhibitory effects of these compounds on CYPs.

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“…[12][13][14] These represent the first reports on the natural occurrence of dimeric quinones in higher-order fungi Basidiomycotina. [12][13][14] These represent the first reports on the natural occurrence of dimeric quinones in higher-order fungi Basidiomycotina.…”

Section: Isolation and Bioactivity 2a Cardinalinsmentioning

confidence: 99%

“…[12][13][14] These represent the first reports on the natural occurrence of dimeric quinones in higher-order fungi Basidiomycotina. Separation of this extract into its individual components yielded a colorless solid [cardinalin 1 (10)], two yellow quinones [cardinalin 2 (11) and cardinalin 3 (1)], and three red-purple pigments [cardinalin 4 (12), cardinalin 5 (13), and cardinalin 6 (14), Figure 2]. Separation of this extract into its individual components yielded a colorless solid [cardinalin 1 (10)], two yellow quinones [cardinalin 2 (11) and cardinalin 3 (1)], and three red-purple pigments [cardinalin 4 (12), cardinalin 5 (13), and cardinalin 6 (14), Figure 2].…”

Section: Isolation and Bioactivity 2a Cardinalinsmentioning

confidence: 99%

Dimeric Pyranonaphthoquinones: Isolation, Bioactivity, and Synthetic Approaches

2016

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The dimeric pyranonaphthoquinones, “bis versions” of the naphtho[2,3‐c]pyran‐5,10‐dione moiety, comprises a group of antibiotics that have been isolated from a variety of sources including plants, bacteria, fungi, and insects. This review discusses the known naturally occurring dimeric pyranonaphthoquinones, their isolation and bioactivity, and synthetic approaches towards them that have helped to confirm their structures, as well as to resolve structural uncertainties such as stereochemistry. The major focus has been on the synthetic approaches adopted to complete the challenging total synthesis of the natural isolates and analogues.

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Pigments of fungi (macromycetes)

Cited by 68 publications

References 11 publications

Absolute stereochemistry of fungal metabolites: icterinoidins A1 and B1, and atrovirins B1 and B2

Absolute stereochemistry of fungal metabolites: icterinoidins A1 and B1, and atrovirins B1 and B2

In VitroInhibitory Effects of Pulvinic Acid Derivatives Isolated from Chinese Edible Mushrooms,Boletus calopusandSuillus bovinus, on Cytochrome P450 Activity

Dimeric Pyranonaphthoquinones: Isolation, Bioactivity, and Synthetic Approaches

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