Pyran Rings Containing Polyketides from Penicillium raistrickii

Ma, Liying; Liu, Desheng; Li, De-Guo; Huang, Yangen; Kang, Hui-Hui; Wang, Chunhua; Liu, Weizhong

doi:10.3390/md15010002

Cited by 13 publications

(13 citation statements)

References 24 publications

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“…Extrolites : Atrovenetins, chrysogine, griseofulvins, penicillic acid, peniciketals, peniciraistrins, pestafolide and desmethylcandidusins are produced by ser. Raistrickiorum species ( Belofsky et al., 1998 , Ma et al., 2012 , Ma et al., 2017b , Liu et al., 2014a , Liu et al., 2018a , Li et al., 2019b ).…”

Section: Resultsmentioning

confidence: 99%

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

Houbraken¹,

Kocsubé²,

Visagie³

et al. 2020

Studies in Mycology

406

458

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The Eurotiales is a relatively large order of Ascomycetes with members frequently having positive and negative impact on human activities. Species within this order gain attention from various research fields such as food, indoor and medical mycology and biotechnology. In this article we give an overview of families and genera present in the Eurotiales and introduce an updated subgeneric, sectional and series classification for Aspergillus and Penicillium . Finally, a comprehensive list of accepted species in the Eurotiales is given. The classification of the Eurotiales at family and genus level is traditionally based on phenotypic characters, and this classification has since been challenged using sequence-based approaches. Here, we re-evaluated the relationships between families and genera of the Eurotiales using a nine-gene sequence dataset. Based on this analysis, the new family Penicillaginaceae is introduced and four known families are accepted: Aspergillaceae , Elaphomycetaceae , Thermoascaceae and Trichocomaceae . The Eurotiales includes 28 genera: 15 genera are accommodated in the Aspergillaceae ( Aspergillago , Aspergillus , Evansstolkia , Hamigera , Leiothecium , Monascus , Penicilliopsis , Penicillium , Phialomyces , Pseudohamigera , Pseudopenicillium , Sclerocleista , Warcupiella , Xerochrysium and Xeromyces ), eight in the Trichocomaceae ( Acidotalaromyces , Ascospirella , Dendrosphaera , Rasamsonia , Sagenomella , Talaromyces , Thermomyces , Trichocoma ), two in the Thermoascaceae ( Paecilomyces , Thermoascus ) and one in the Penicillaginaceae ( Penicillago ). The classification of the Elaphomycetaceae was not part of this study, but according to literature two genera are present in this family ( Elaphomyces and Pseudotulostoma ). The use of an infrageneric classification system has a long tradition in Aspergillus and Penicillium . Most recent taxonomic studies focused on the sectional l...

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Section: Resultsmentioning

confidence: 99%

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

Houbraken¹,

Kocsubé²,

Visagie³

et al. 2020

Studies in Mycology

406

458

View full text Add to dashboard Cite

show abstract

“…The above information suggested a symmetrically tetrasubstituted phenyl ring in 1 . The upfield chemical shift (δ C 8.9) of the arylmethyl group implied that it was sandwiched between two phenolic hydroxyls in the phenyl ring [ 16 , 17 ]. Furthermore, the upfield chemical shift (δ C 199.2) of keto carbonyl suggested it to be conjugated with the phenyl ring, and located at the para position of the arylmethyl, which was proven by the non-chelated phenolic hydroxyl signals at δ H 6.89.…”

Section: Resultsmentioning

confidence: 99%

“…Among the cultivation-based approaches, thermo change is one of the effective strategies for triggering silent biosynthetic expression systems to enlarge the numbers of fungi-derived natural products, with only a few cases reported [ 13 , 14 , 15 ]. Strain JH-18 of P. raistrickii , which was isolated from marine saline soil of the coast of Bohai Bay in China, was investigated with only a few reports [ 16 , 17 , 18 , 19 ]. Its routine laboratory fermentation enabled the isolation of series of novel natural products including spiroketals, isocoumarins, α-pyrone, and dihydropyran derivatives [ 16 , 17 , 18 ], and some of them possess an unusual chemical skeleton and exhibit cytotoxic activity [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

Raistrickiones A−E from a Highly Productive Strain of Penicillium raistrickii Generated through Thermo Change

et al. 2018

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Three new diastereomers of polyketides (PKs), raistrickiones A−C (1–3), together with two new analogues, raistrickiones D and E (4 and 5), were isolated from a highly productive strain of Penicillium raistrickii, which was subjected to an experimental thermo-change strategy to tap its potential of producing new secondary metabolites. Metabolites 1 and 2 existed in a diastereomeric mixture in the crystal packing according to the X-ray data, and were laboriously separated by semi-preparative HPLC on a chiral column. The structures of 1–5 were determined on the basis of the detailed analyses of the spectroscopic data (UV, IR, HRESIMS, 1D, and 2D NMR), single-crystal X-ray diffractions, and comparison of the experimental and calculated electronic circular dichroism spectra. Compounds 1–5 represented the first case of 3,5-dihydroxy-4-methylbenzoyl derivatives of natural products. Compounds 1–5 exhibited moderate radical scavenging activities against 1,1-diphenyl-2-picrylhydrazyl radical 2,2-diphenyl-1-(2,4,6-trinitrophenyl) hydrazyl (DPPH).

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“…Instrumentation used to acquire UV, IR, HRESIMS, optical rotation, and 1D and 2D NMR spectra and to perform column chromatography has been previously described [ 6 , 7 , 8 ] A TU-1091 spectrophotometer (Beijing Purkinje General Instrument Co., Ltd., Beijing, China) was used to measure the UV spectra in MeOH. An attenuated total reflection (ATR) method was employed to record the infrared spectra on a Nicolet 6700 spectrophotometer (Thermo Fisher Scientific, Madison, WI, USA).…”

Section: Methodsmentioning

confidence: 99%

“…In our continuing search for new biologically active metabolites from fungi [ 6 , 7 ], the prolific fungus A. iizukae was isolated from coastal saline soil in Kenli, China. Previously, two new diphenyl derivatives and nine known compounds were obtained from it in a shaken fermentation, and six of them contain chloride atoms, that demonstrating the strain was able to utilize chlorine in the biosynthesis of its metabolites [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

Potential Antiviral Xanthones from a Coastal Saline Soil Fungus Aspergillus iizukae

et al. 2018

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Five new (1–5) and two known xanthones (6 and 7), one of the latter (6) obtained for the first time as a natural product, together with three known anthraquinones, questin, penipurdin A, and questinol, were isolated from the coastal saline soil-derived Aspergillus iizukae by application of an OSMAC (one strain many compounds) approach. Their structures were determined by interpretation of nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, as well as comparison of these data with those of related known compounds. Antiviral activity of xanthones 1−7 was evaluated through the cytopathic effect (CPE) inhibition assay, and compound 2 exhibited distinctly strong activity towards influenza virus (H1N1), herpes simplex virus types 1 (HSV-1) and 2 (HSV-2) with IC50 values of 44.6, 21.4, and 76.7 μM, respectively, which indicated that it was worth to further investigate it as a potential lead compound. The preliminary structure-activity relationship of the xanthones is discussed.

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Pyran Rings Containing Polyketides from Penicillium raistrickii

Cited by 13 publications

References 24 publications

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

Raistrickiones A−E from a Highly Productive Strain of Penicillium raistrickii Generated through Thermo Change

Potential Antiviral Xanthones from a Coastal Saline Soil Fungus Aspergillus iizukae

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