Minor anthraquinonoid metabolites of <i>Cercospora</i><i>arachidicola</i>

Stoessl, A.; Stothers, J. B.

doi:10.1139/v85-214

Cited by 15 publications

(3 citation statements)

References 10 publications

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“…Accordingly, two new brominated anthraquinones ( 8 , 9 ) and a new anthraquinone ( 10 ) were obtained from MeOH extracts of the fungal mycelia. The known compounds averantin ( 11 ), − 1′- O -methylaverantin ( 12 ), 6- O -methylaverantin ( 13 ), averantin-1′-butyl ether ( 14 ), and averythrin ( 15 ) were identified on the basis of comparison of their 1D NMR with previously reported data (Supporting Information, Tables S1–S5). The specific rotation of 11 showed a negative value ([α] 25 D −140 ( c 0.05, MeOH)), which is in agreement with that of ( S )-(−)-averantin ([α] 22 579 −138 ( c 0.37, EtOH)) .…”

Section: Resultsmentioning

confidence: 98%

Halogenated Anthraquinones from the Marine-Derived Fungus Aspergillus sp. SCSIO F063

et al. 2012

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Metabolomic investigations focusing on the marine-derived fungus Aspergillus sp. SCSIO F063 have unveiled seven new chlorinated anthraquinones (1–7) related to averantin, together with five known analogues (11–15) when the fungus was fermented using sea salt-containing potato dextrose broth. Through the addition of sodium bromide to the broth, two new brominated anthraquinones (8, 9) and one new nonhalogenated anthraquinone (10) were obtained from the fungal mycelia. Their structures were elucidated by extensive spectroscopic analyses including MS and 1D and 2D NMR data. One metabolite, 6-O-methyl-7-chloroaveratin (2), displayed inhibition activity against three human tumor cell lines, SF-268, MCF-7, and NCI-H460, with IC50 values of 7.11, 6.64, and 7.42 μM, respectively.

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Section: Resultsmentioning

confidence: 98%

Halogenated Anthraquinones from the Marine-Derived Fungus Aspergillus sp. SCSIO F063

et al. 2012

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“…Three metabolites were identified in the LO11174 control strain, including 2,ωdihydroxyemodin (21), 27 3-methylorsellinic acid (22), and an unknown compound (23). Compounds 21−23 were upregulated in the llmG overexpression strains along with 12 additional metabolites (1, 14, 18, 19, and 24−31), including 1 and its intermediates 14, 28 versicolorin B (24), 28 averantin (25), 30 metabolites from the emodin/mondictyphenone pathway, 31 monodictyphenone (26), ω-hydroxyemodin (27), 2hydroxyemodin (28), emodin (29), chrysophanol (30), nidulanins (18 and 19), 13,19 3-methylorsellinic acid (22), 32 and an unknown (31) (Figure 2B, ii−iv). As was the case for GMM(s), we observed an even greater increase in production of the same SMs in the mcrAΔ strain than in the llmG overexpression strains and, notably, the gpdA(p)llmG, mcrAΔ strain demonstrated enhanced SM production in comparison with the mcrAΔ strain (Figure 2B, iii and iv, Supplemental Table 2).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Overexpression of an LaeA-like Methyltransferase Upregulates Secondary Metabolite Production in Aspergillus nidulans

et al. 2019

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Fungal secondary metabolites (SMs) include medically valuable compounds as well as compounds that are toxic, carcinogenic and/or contributors to fungal pathogenesis. It is consequently important to understand the regulation of fungal secondary metabolism. McrA is a recently discovered transcription factor that negatively regulates fungal secondary metabolism. Deletion of mcrA (mcrAΔ), the gene encoding McrA, results in upregulation of many SMs and alters the expression of more than 1000 genes. One gene strongly upregulated by the deletion of mcrA is llmG, a putative methyl transferase related to LaeA, a major regulator of secondary metabolism. We have artificially upregulated llmG by replacing its promoter with strong constitutive promoters in strains carrying either wild-type mcrA or mcrAΔ. Upregulation of llmG, on various media, resulted in increased production of the important toxin sterigmatocystin and compounds from at least six major SM pathways. llmG is, thus, a master SM regulator. mcrAΔ generally resulted in greater upregulation of SMs than upregulation of llmG, indicating that the full effects of mcrA on secondary metabolism involve genes in addition to llmG. However, the combination of mcrAΔ and upregulation of llmG generally resulted in greater compound production than mcrAΔ alone (in one case more than 460 times greater than the control). This result indicates that deletion of mcrA and/or upregulation of llmG can likely be combined with other strategies for eliciting SM production to greater levels than can be obtained with any single strategy.

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“…The homogenate was filtered and allowed to stand for 1 h. The organic phase, which contained the anthraquinones, was evaporated to dryness under reduced pressure. DOTH was crystallized from pyridine as described previously (Stoessl & Stothers, 1985). DOTH and the minor anthraquinones contained in the pyridine filtrates were further purified by preparative TLC (20 X 20 cm plates, 0-5 mm thick silica gel G) developed with choloroform:methanol:formic acid (50:3, v.v plus 1% v.v formic acid).…”

Section: Isolation Of Doth and Fungal Anthraquinonesmentioning

confidence: 99%

Competitive ELISA employing monoclonal antibodies specific for dothistromin

Jones

Harvey

Jones

et al. 1993

Food and Agricultural Immunology

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Dothistromin (DOTH) is a fungal toxin occurring inPinus radiata needles contaminated with Dothistroma pini. Monoclonal antibodies (MAbs) of high affinity were prepared against DOTH and incorporated into competitive ELISAs. MAbs were secreted by hybridoma prepared from mice immunized with DOTH conjugated, through the aromatic ring of the anthraquinone, to bovine serum albumin. DOTH could be quantitated at 2-60 ng ml -1 (0.1-2 ng/assay) and at 8-300 ng ml -1 (0.4-15 ng/assay) using peroxidase-labelled MAb 10C12A5 and MAb 6A2D4 respectively in indirect competitive ELISA. The corresponding limits of detection of DOTH were < 300 pg and 1 ng ml -1 respectively. The furan ring was an important structure in the epitope recognized by both MAbs.

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Minor anthraquinonoid metabolites of Cercosporaarachidicola

Cited by 15 publications

References 10 publications

Halogenated Anthraquinones from the Marine-Derived Fungus Aspergillus sp. SCSIO F063

Halogenated Anthraquinones from the Marine-Derived Fungus Aspergillus sp. SCSIO F063

Overexpression of an LaeA-like Methyltransferase Upregulates Secondary Metabolite Production in Aspergillus nidulans

Competitive ELISA employing monoclonal antibodies specific for dothistromin

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