The Biosynthesis of Citrinin in Penicillium citrinum. II. Tracer Studies on the Formation of Citrinin<sup>*</sup>

Rodig, Oscar R.; Ellis, L. C.; Glover, Irving T.

doi:10.1021/bi00871a041

Cited by 14 publications

(6 citation statements)

References 16 publications

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“…21 Compound 1 possesses a carbon skeleton similar to citrinin (2), and it is possibly biosynthesized via mixed routes. The proposed biosynthesis of compound 1 proceeds via an enzyme-bonded poly-b-ketone chain 22 and the amino acid formation is accomplished by an aminotransferase (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

Yao¹,

Sebisubi²,

Voo³

et al. 2011

J. Braz. Chem. Soc.

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A investigação do extrato orgânico produzido na fermentação microbiológica de Penicillium sp. H9318 conduziu ao isolamento de um novo alcaloide isoquinolínico, o composto (5S)-3,4,5,7-tetrametil-5,8-di-hidróxi-6(5H)-isoquinolinona (1), juntamente com quatro outros conhecidos compostos derivados da citrinina (2-5). Uma atividade inibitória significativa no ensaio da inibição da formação dos halos (HFI), foi exibida pela citrinina (2), semelhante àquela observada pelo Streptomyces 85E, enquanto os compostos 1, 3, 4 e 5 não mostraram atividade inibitória com respeito ao ensaio HFI quando testados com 20 mg/disco. Em relação ao ensaio de citotoxicidade, a citrinina (2) demonstrou uma atividade inibitória mais fraca quando comparada as linhagens de células cancerosas MCF-7 (IC 50 71,93 µmol L -1 ), LNCaP (IC 50 77,92 µmol L -1 ), LU-1 (147,85 µmol L -1 ) e KB (IC 50 65,93 µmol L -1 ).Investigation of a microbial fermentation organic extract of Penicillium sp. H9318 led to the isolation of a new isoquinolinone alkaloid, (5S)-3,4,5,7-tetramethyl-5,8-dihydroxyl-6(5H)-isoquinolinone (1), along with four known citrinin derivatives (2-5). Citrinin (2) exhibited significant inhibitory activity against Streptomyces 85E in the hyphae formation inhibition (HFI) assay, while compounds 1, 3-5 were not active when tested at 20 mg/disk in the HFI assay. Citrinin (2) further demonstrated a weak inhibitory activity against MCF-7 (IC 50 71.93 µmol L -1 ), LNCaP (IC 50 77.92 µmol L -1 ), LU-1 (147.85 µmol L -1 ) and KB (IC 50 65.93 µmol L -1 ) cell lines, respectively, in the cytotoxicity assay.

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Section: Resultsmentioning

confidence: 99%

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

Yao¹,

Sebisubi²,

Voo³

et al. 2011

J. Braz. Chem. Soc.

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“…[ethyl acetate-light petroleum (b.p. 60-80 "C), 2: 11 to give one main band, R, 0 The second band, RF 0.75, gave starting material (15) (4 mg, 16%).…”

Section: Methodsmentioning

confidence: 99%

A diastereoselective synthesis of the polyketide antibiotic citrinin using toluate anion chemistry

Barber¹,

Staunton²,

Wilkinson³

1986

J. Chem. Soc., Perkin Trans. 1

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“…Os primeiros trabalhos sugerem que a citrinina produzida pela espécie Aspergillus candidus é derivada de pentacetídeos formados pela condensação de cinco grupos de acetato e de três átomos de carbono. [28][29][30][31][32][33] Mais recentemente a rota biossintética foi confirmada utilizando marcadores isotópicos, sugerindo que a formação da citrinina seja através de tetracetídeos em culturas de Monascus ruber (Figura 4). A síntese da citrinina foi proposta em 1949 (Figura 5).…”

Section: Biossíntese E Síntese Da Citrininaunclassified

History, Applications, Activity and Changes of Citrinin

Cruz

Costa

Figueroa‐Villar

2016

Revista Virtual De Química

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Abstract:Citrinin is a natural product obtained from fungi and with good biological activity. Because this compound also presents toxicity, especially being nephrotoxicity, its structural modification is important to obtain new potential pharmacological agents without toxicity. This article presents the history, obtention methods, synthesis, structural modification, evaluation and biological activity of citrinin.Keywords: Citrinin; Penicillium; mycotoxins; biosynthesis; antibiotic; nephrotoxicity. ResumoA Citrinina é um produto natural obtido de fungos e com boa atividade biológica. Como ela também apresenta certa toxidez, especialmente sendo nefrotóxica, é importante sua modificação estrutural para obter novos fármacos sem essa toxidez. Este artigo apresenta a história, os métodos de obtenção, síntese, modificação estrutural, avaliação e atividade biológica da citrinina.

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The Biosynthesis of Citrinin in Penicillium citrinum. II. Tracer Studies on the Formation of Citrinin^*

Cited by 14 publications

References 16 publications

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

A diastereoselective synthesis of the polyketide antibiotic citrinin using toluate anion chemistry

History, Applications, Activity and Changes of Citrinin

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The Biosynthesis of Citrinin in Penicillium citrinum. II. Tracer Studies on the Formation of Citrinin*

Cited by 14 publications

References 16 publications

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

A diastereoselective synthesis of the polyketide antibiotic citrinin using toluate anion chemistry

History, Applications, Activity and Changes of Citrinin

Contact Info

Product

Resources

About

The Biosynthesis of Citrinin in Penicillium citrinum. II. Tracer Studies on the Formation of Citrinin^*