Structures of TMC-120A, B and C, novel isoquinoline alkaloids from Aspergillus ustus TC 1118

Kohno, Jun; Hiramatsu, Hidenori; Nishio, Maki; Sakurai, Masaaki; Okuda, Tôru; Komatsubara, Saburo

doi:10.1016/s0040-4020(99)00648-1

Cited by 45 publications

(39 citation statements)

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“…Several similar novel isoquinoline alkaloids have been reported from the genus of Penicillium, 17 Aspergillus, 18 Streptomyces 19,20 and Chaetomium. 21 Most isoquinoline alkaloids discovered from plants exhibit complicated structures, which were mainly synthesized from tyrosine, whereas most isoquinolines from lichens, fungi, and sponges show simple skeletons and are probably biosynthesized via mixed pathways.…”

Section: Resultsmentioning

confidence: 80%

“…The chemical shift Chromatographic fractions and pure compounds were monitored by TLC, detected by absorption of UV light at 254 nm and a color reaction by spraying with a solution of 10%, v/v, sulfuric acid/EtOH followed by 5 min heating at 120 °C. MPLC (medium pressure column chromatography) was carried out on a Büchi ® pump system and a Büchi column packed with Merck silica gel 60 and/or reversed-phase C 18 .…”

Section: General Proceduresmentioning

confidence: 99%

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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: 80%

Section: General Proceduresmentioning

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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“…The organic layer was washed with brine, dried over Na 2 SO 4 , and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 10 g) using EtOAc-hexane (4 : 1) as an eluent to give TMC-120B (2) (14 mg, 58%), mp 175-178°C (MeOH) (lit., 8,9) mp 176-178°C …”

Section: Methyl [6-formyl-3-hydroxy-2-(methoxyiminomethyl)phenyloxy]amentioning

confidence: 99%

“…1), which were isolated from a fermentation broth of Aspergillus ustus TC 1118 by . 8,9) Their structures have been determined by spectroscopic, chemical, and X-ray analyses. TMC-120B (2) shows moderate inhibitory activity against the interleukin-5 mediated prolongation of eosinophil survival (IC 50 ϭ2.0 mM).…”

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confidence: 99%

Synthesis of the New Furo[3,2-h]isoquinoline Alkaloid, TMC-120B from Aspergillus ustus

Kumemura

Choshi

Hirata

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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A total synthesis of a new furo[3,2-h]isoquinoline alkaloid TMC120-B (2), isolated from Aspergillus ustus together with two related compounds, has been completed in sixteen steps. The key step is the synthesis of the appropriate 3,7,8-trisubstituted isoquinoline framework (23) based on a thermal electrocyclic reaction of the 1-aza 6p p-electron system involving the benzene double bond. In addition, the microwave assisted electrocyclic reaction of this system was newly performed.

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“…The genus has proven to be a rich source of secondary metabolites with novel structures and interesting bioactivity. [7][8][9][10][11] Examples of isolated metabolites include meroterpenoids, [10,[12][13][14] isochroman derivatives, [9,[15][16][17] drimane sesquiterpenoids, [7,18] and cyclic tripeptides, [11] which exhibited interesting biological activities such as plant growth inhibition, [15] cytotoxic activity against tumor cell lines, [7,9] selective antifungal activity, [11] as well as inhibition of endothelin-type B receptors. [18] As part of our ongoing research on marine fungi, [7,19,20] we have investigated a marine-derived fungal Aspergillus strain, isolated from a specimen of the Mediterranean sponge Tethya aurantium.…”

Section: Introductionmentioning

confidence: 99%

New Austalides from the Sponge‐Associated Fungus Aspergillus sp.

et al. 2011

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Keywords: Natural products / Fused-ring systems / Circular dichroism / Density functional calculations / Structure elucidation / CytotoxicityChromatographic separation of a crude extract obtained from the fungus Aspergillus sp., isolated from the Mediterranean sponge Tethya aurantium, yielded five new meroterpenoid metabolites, austalides M-Q (1-5), together with nine known compounds (6-13). The structures of the new compounds were unambiguously elucidated on the basis of extensive 1D and 2D NMR methods and by mass spectral analysis. Furthermore, the absolute configurations of 1 and 4 were determined by time-dependent density functional theory electronic circular dichroism (TDDFT ECD) calculations, allowing the assignment of the absolute configuration of analo-

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Structures of TMC-120A, B and C, novel isoquinoline alkaloids from Aspergillus ustus TC 1118

Cited by 45 publications

References 1 publication

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

Synthesis of the New Furo[3,2-h]isoquinoline Alkaloid, TMC-120B from Aspergillus ustus

New Austalides from the Sponge‐Associated Fungus Aspergillus sp.

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