Mansouramycins A−D, Cytotoxic Isoquinolinequinones from a Marine Streptomycete

Hawas, Usama W.; Shaaban, Mohamed; Shaaban, Khaled A.; Speitling, Michael; Maier, Armin; Kelter, Gerhard; Fiebig, Heinz H.; Meiners, Marinus; Helmke, Elisabeth; Laatsch, Hartmut

doi:10.1021/np900160g

Cited by 102 publications

(88 citation statements)

References 23 publications

(30 reference 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: 82%

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: 82%

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

Yao¹,

Sebisubi²,

Voo³

et al. 2011

J. Braz. Chem. Soc.

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“…In vitro cytotoxicity against several human cancer cell lines such as MDA-MB-231, HCT 15, human prostate cancer (PC-3), human lung cancer (NCI-H23), human renal cancer (ACHN), human skin cancer (LOXIMVI), K562 proved that streptokordin exhibited significant cytotoxicity (Jeong et al 2006). Hawas et al (2009) reported the isolation of Streptomyces sp. Mei37 from the muddy sediment of Jade Bay on the southern German North Sea coast, which produced five isoquinolinequinones among which mansouramycin C as the main quinone.…”

Section: Indolocarbazolesmentioning

confidence: 99%

“…Mansouramycin C dark red in color, showed highest cytotoxic action compared with other mansouramycis. When tested on 36 different cancer cell lines it exhibited action against 10 cell lines (T-24, SF-268, LXFA629L, MEXF 520L, OVCAR-3, RXF944L and UXF1138L), with inhibition concentrations ranging from 0.008 to 0.02 µM (Hawas et al 2009). Streptomyces sp.…”

Section: Introductionmentioning

confidence: 99%

Ocean Dwelling Actinobacteria as Source of Antitumor Compounds

Gomathi

Gothandam

2016

Braz. arch. biol. technol.

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“…Mansouramycins A-D are isoquinolinequinones isolated from the marine-derived Mei37 isolate of Streptomyces sp. They show antitumour activity against lung cancer, breast cancer, melanoma and prostate cancer cells [11,75]. Tartrolons, compounds leukaemia cell line K562), antiprotozoal and free radical scavenging activity (Figure 9) [78].…”

Section: Anticancer Activity Of Actinomycete Metabolites Now and In mentioning

confidence: 99%

Biologically active secondary metabolites from Actinomycetes

Solecka¹,

Zajko²,

Postek³

et al. 2012

Open Life Sciences

110

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AbstractSecondary metabolites obtained from Actinomycetales provide a potential source of many novel compounds with antibacterial, antitumour, antifungal, antiviral, antiparasitic and other properties. The majority of these compounds are widely used as medicines for combating multidrug-resistant Gram-positive and Gram-negative bacterial strains. Members of the genus Streptomyces are profile producers of previously-known secondary metabolites. Actinomycetes have been isolated from terrestrial soils, from the rhizospheres of plant roots, and recently from marine sediments. This review demonstrates the diversity of secondary metabolites produced by actinomycete strains with respect to their chemical structure, biological activity and origin. On the basis of this diversity, this review concludes that the discovery of new bioactive compounds will continue to pose a great challenge for scientists.

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Mansouramycins A−D, Cytotoxic Isoquinolinequinones from a Marine Streptomycete

Cited by 102 publications

References 23 publications

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

Ocean Dwelling Actinobacteria as Source of Antitumor Compounds

Biologically active secondary metabolites from Actinomycetes

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