Isolation and characterization of luteoskyrin and rugulosin, two hepatotoxic anthraquinonoids from Penicillium islandicum Sopp. and Penicillium rugulosum Thom.

Jc, Bouhet; Pp, Van Chuong; Toma, Fareed Matti; Kirszenbaum, Marek; Fromageot, P.

doi:10.1021/jf60207a028

Cited by 23 publications

(9 citation statements)

References 25 publications

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“…Emodin ( 1 ), one of the most widely distributed anthraquinones, is found in various species of plants and fungi . It plays a crucial role as a biosynthetic precursor for many fungal metabolites such as the ergochromes ( Penicillium oxalicum ), xanthones ( Aspergillus versicolor ), monodictyphenone ( Aspergillus nidulans ), and bisanthraquinones ( Penicillium islandicum , Myrothecium verucaria , and Penicillium rugulosum ) . The astonishing molecular diversity is due to the versatile chemical properties of anthraquinones: reduction or oxidation and subsequent transformations may provide easy access to a variety of monomeric and dimeric metabolites.…”

Section: Figurementioning

confidence: 99%

Monomeric Dihydroanthraquinones: A Chemoenzymatic Approach and its (Bio)synthetic Implications for Bisanthraquinones

Saha

Mondal

Witte

et al. 2018

Chemistry A European J

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Modified bisanthraquinones are complex dimeric natural products containing a cage-like structural motif. For their biosynthesis, monomeric dihydroanthraquinones have been proposed as key intermediates despite not being isolated from natural sources or synthesized as of yet. Here, isolation and characterization of dihydroemodin, as well as dihydrolunatin, synthesized by a biomimetic and chemoenzymatic approach using NADPH-dependent polyhydroxyanthracence reductase (PHAR) from Cochliobolus lunatus followed by Pb(OAc) oxidation is reported. Subsequent dimerization through a hetero-Diels-Alder reaction of the dihydroemodin and dihydrolunatin resulted in (-)-flavoskyrin (68 %) and (-)-lunaskyrin (62 %), respectively. Pyridine treatment of (-)-flavoskyrin and (-)-lunaskyrin gave (-)-rugulosin and (-)-2,2'-epi-cytoskyrin A in 64 % and 60 % yield, respectively, through a cascade that involves two dimeric intermediates. Implications of the described synthesis for the biosynthesis of bisanthraquinones by a combination of enzymatic and spontaneous steps are discussed.

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Section: Figurementioning

confidence: 99%

Monomeric Dihydroanthraquinones: A Chemoenzymatic Approach and its (Bio)synthetic Implications for Bisanthraquinones

Saha

Mondal

Witte

et al. 2018

Chemistry A European J

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“…A teenaged boy needed an immediate liver transplant after drinking rhubarb-wine, which was contaminated with T. purpurogenus and contained a high concentration of rubratoxin ( Sigler et al 1996, Richer et al 1997 ). Talaromyces islandicus is one of the most destructive and harmful fungi affecting rice in storage, causing the yellowing of rice ( Saito et al 1971, Sakai et al 2005, Oh et al 2008 ) and also produces mycotoxins such as cyclochlorotine, islanditoxin, erythroskyrine and luteoskyrin, which are hepatotoxic agents and carcinogenic ( Uraguchi et al 1961, 1972, Uraguchi 1962, Ueno & Ishikawa 1969, Bouhet et al 1976, Stark et al 1978 ). Talaromyces islandicus , T. radicus , T. rugulosus and T. wortmannii produce rugulosin and skyrin.…”

Section: Introductionmentioning

confidence: 99%

Polyphasic taxonomy of the genus Talaromyces

Yılmaz¹,

Visagie²,

Houbraken³

et al. 2014

Studies in Mycology

322

396

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The genus Talaromyces was described by Benjamin in 1955 as a sexual state of Penicillium that produces soft walled ascomata covered with interwoven hyphae. Phylogenetic information revealed that Penicillium subgenus Biverticillium and Talaromyces form a monophyletic clade distinct from the other Penicillium subgenera. Subsequently, in combination with the recent adoption of the one fungus one name concept, Penicillium subgenus Biverticillium was transferred to Talaromyces. At the time, the new combinations were made based only on phylogenetic information. As such, the aim of this study was to provide a monograph on Talaromyces applying a polyphasic species concept, including morphological, molecular and physiological characters. Based on an ITS, BenA and RPB2 multigene phylogeny, we propose a new sectional classification for the genus, placing the 88 accepted species into seven sections, named sections Bacillispori, Helici, Islandici, Purpurei, Subinflati, Talaromyces and Trachyspermi. We provide morphological descriptions for each of these species, as well as notes on their identification using morphology and DNA sequences. For molecular identification, BenA is proposed as a secondary molecular marker to the accepted ITS barcode for fungi.

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“…Bearing an inversion center, dibefurin belongs to the molecular point group C i , which is rare amongst natural products. [12] By contrast, C 2 symmetry is frequently encountered in fungal metabolites, for instance in the phenolic dimers (+)-rugulosin [13] and (À)-trichodimerol. [2a,b, 14] Further increasing its attractiveness as a synthetic target, dibefurin shows remarkable biological activity.…”

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confidence: 99%

Biomimetic Synthesis of the Calcineurin Phosphatase Inhibitor Dibefurin

2014

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Dibefurin is a Ci -symmetric natural product that acts as an inhibitor of calcineurin phosphatase. A six-step synthesis of this compound is reported, which features an oxidative dimerization of the aromatic polyketide epicoccine as the key step. Dibefurin is proposed to be related to epicolactone, a complex yet racemic fungal metabolite that has recently been discovered. Attempts to access epicolactone from epicoccine and epicoccone B resulted in an unusual dimer that is formed through a hetero-Diels-Alder reaction of a para-quinone methide with an ortho-quinone.

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Isolation and characterization of luteoskyrin and rugulosin, two hepatotoxic anthraquinonoids from Penicillium islandicum Sopp. and Penicillium rugulosum Thom.

Cited by 23 publications

References 25 publications

Monomeric Dihydroanthraquinones: A Chemoenzymatic Approach and its (Bio)synthetic Implications for Bisanthraquinones

Monomeric Dihydroanthraquinones: A Chemoenzymatic Approach and its (Bio)synthetic Implications for Bisanthraquinones

Polyphasic taxonomy of the genus Talaromyces

Biomimetic Synthesis of the Calcineurin Phosphatase Inhibitor Dibefurin

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