Miniolins A–C, novel isomeric furanones induced by epigenetic manipulation of Penicillium minioluteum

Tang, Huibin; Zhang, Qiang; Gao, Yuqi; Zhang, Anling; Gao, Jin‐Ming

doi:10.1039/c4ra11712c

Cited by 23 publications

(10 citation statements)

References 32 publications

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“…Fungi of the genus Penicillium are rich in bioactive compounds [ 4 , 5 , 6 , 7 , 8 ], and among them, Penicillium minioluteum produces bioactive metabolites, for example, polyketide-terpenoid hybrids [ 9 ], hydrazide derivative as a potentiator of nerve growth factor [ 10 ], and antifungal tetracyclic diterpenes [ 11 ]. The fungus P. minioluteum was recently found to produce isomeric furanones through epigenetic manipulation through the addition of azacitidine, a DNA methyltransferase inhibitor [ 12 ]; it was also used in the biotransformation of clovane derivatives for the synthesis of rumphellclovane A [ 13 ]. It should be noted that the name of the fungus P. minioluteum was recently revised to “ Talaromyces minioluteus ” [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

Drimane Sesquiterpene-Conjugated Amino Acids from a Marine Isolate of the Fungus Talaromyces minioluteus (Penicillium Minioluteum)

et al. 2015

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Four new sesquiterpene lactones (3, 4, 6 and 7) and three known compounds, purpuride (1), berkedrimane B (2) and purpuride B (5), were isolated from the marine fungus, Talaromyces minioluteus (Penicillium minioluteum). New compounds were drimane sesquiterpenes conjugated with N-acetyl-l-valine, and their structures were elucidated by analysis of spectroscopic data, as well as by single crystal X-ray analysis. The isolated compounds could not inhibit the apoptosis-regulating enzyme, caspase-3, while three of the compounds (2, 3 and 7) exhibited weak cytotoxic activity.

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Section: Introductionmentioning

confidence: 99%

Drimane Sesquiterpene-Conjugated Amino Acids from a Marine Isolate of the Fungus Talaromyces minioluteus (Penicillium Minioluteum)

et al. 2015

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“…The configuration at C-5 was proposed to be S based on the negative optical rotation of 3 (−36.67) by opposition to that of ( R )- cis -gregatin B (+168). Furthermore, the negative Cotton effect observed in the 255–265 nm region of the electronic circular dichroism (ECD) curves of Compound 3 in EtOH ( Figure 3 ), when compared to the ECD spectra of aspertetronin A, was indicative of the S configuration [ 7 ]. The new natural furanone was finally elucidated as methyl (5 S )-5-[(1′ E ,3′ Z )-hexa-1,3-dienyl]-5-methyl-4-oxo-2-methyl 4,5-dihydrofuran-3 carboxylate ((5 S ) cis -gregatin B).…”

Section: Resultsmentioning

confidence: 99%

Furanones and Anthranilic Acid Derivatives from the Endophytic Fungus Dendrothyrium variisporum

et al. 2017

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Extracts from an endophytic fungus isolated from the roots of the Algerian plant Globularia alypum showed prominent antimicrobial activity in a screening for novel antibiotics. The producer organism was identified as Dendrothyrium variisporum by means of morphological studies and molecular phylogenetic methods. Studies on the secondary metabolite production of this strain in various culture media revealed that the major components from shake flasks were massarilactones D (1) and H (2) as well as two new furanone derivatives for which we propose the trivial names (5S)-cis-gregatin B (3) and graminin D (4). Scale-up of the fermentation in a 10 L bioreactor yielded massarilactone D and several further metabolites. Among those were three new anthranilic acid derivatives (5–7), two known anthranilic acid analogues (8 and 9) and three cyclopeptides (10–12). Their structures were elucidated on the basis of extensive spectroscopic analysis (1D- and 2D-NMR), high-resolution mass spectrometry (HRESIMS), and the application of the modified Mosher’s method. The isolated metabolites were tested for antimicrobial and cytotoxic activities against various bacteria, fungi, and two mammalian cell lines. The new Metabolite 5 and Compound 9 exhibited antimicrobial activity while Compound 9 showed cytotoxicity activity against KB3.1 cells.

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“…The mycology of the genus Talaromyces , in addition to a brief summary of the few secondary metabolites reported from T. minioluteus , has been reviewed recently (Yilmaz et al, 2014). Miniolins A–C were reported from an epigenetically modified culture of P. minioluteum (now T. minioluteus ) (Tang et al, 2015). Our ongoing studies of endophytes of milk thistle and other medicinal plants have also yielded a suite of secondary metabolites belonging to structurally diverse classes (Bussey et al, 2015; El-Elimat et al, 2014b; Figueroa et al, 2014; Kaur et al, 2015; Raja et al, 2015).…”

Section: Discussionmentioning

confidence: 99%

Talarolutins A–D: Meroterpenoids from an endophytic fungal isolate of Talaromyces minioluteus

et al. 2016

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Four meroterpenoids [talarolutins A–D] and one known compound [purpurquinone A] were characterized from an endophytic fungal isolate of Talaromyces minioluteus (G413), which was obtained from the leaves of the medicinal plant milk thistle [Silybum marianum (L.) Gaertn. (Asteraceae)]. The structures of talarolutins A–D were determined by the analysis of various NMR and MS techniques. The relative and absolute configuration of talarolutins A was determined by X-ray diffraction analysis. A combination of NOESY data and comparisons of ECD spectra were employed to assign the relative and absolute configuration of the other analogues. Talarolutins B–D were tested for cytotoxicity against human prostate carcinoma (PC-3) cell line, antimicrobial activity, and induction of quinone reductase; no notable bioactivity was observed in any assay.

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Miniolins A–C, novel isomeric furanones induced by epigenetic manipulation of Penicillium minioluteum

Abstract: Cultivation of Penicillium minioluteum with a DNA methyltransferase inhibitor led to the isolation of a novel type of aspertetronin dimer, miniolins A–C, along with their precursor. The dimeric absolute configurations were assigned by chiral HPLC and ECD calculations.

Cited by 23 publications

References 32 publications

Drimane Sesquiterpene-Conjugated Amino Acids from a Marine Isolate of the Fungus Talaromyces minioluteus (Penicillium Minioluteum)

Drimane Sesquiterpene-Conjugated Amino Acids from a Marine Isolate of the Fungus Talaromyces minioluteus (Penicillium Minioluteum)

Furanones and Anthranilic Acid Derivatives from the Endophytic Fungus Dendrothyrium variisporum

Talarolutins A–D: Meroterpenoids from an endophytic fungal isolate of Talaromyces minioluteus

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