Brasiliquinones A, B and C, New Benz(a)anthraquinone Antibiotics from Nocardia brasiliensis. I. Producing Strain, Isolation and Biological Activities of the Antibiotics.

Nemoto, Akira; Tanaka, Yasushi; Karasaki, Yuji; Komaki, Hisayuki; Yazawa, Kazunaga; Mikami, Yuzuru; Tojo, Takashi; Kadowaki, Kiyoshi; Tsuda, Masashi; Kobayashi, Jun’ichi

doi:10.7164/antibiotics.50.18

Cited by 25 publications

(18 citation statements)

References 11 publications

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“…Compounds anthramycin and brasiliquinone-C were identified in the extract from RKMT_184. Both compounds are reported as antimicrobial agents and may be responsible for the antimicrobial activity exhibited by the fermentation extract of this strain (Kohn et al 1967;Nemoto et al 1997). N-acetyl-β-oxotryptamine, mansouramycin A, sannanine and caerulomycin F were also tentatively identified, although further study is needed to confirm the identity of the active constituents of these extracts.…”

Section: Discussionmentioning

confidence: 92%

“…However, only one of them, brasiliquinone C, was reported from a bacterial source. Brasilquinone C is active against Gram-positive bacteria and thus may be in part responsible for the antimicrobial activity observed in the RKMT_184 extract (Nemoto et al 1997). The compound eluting at 2.13 min with a m/z of 217.0972 [M + H] + had four hits in Antibase with the molecular formula C 12 H 12 N 2 O 2 (Δ ppm = 0.54 ppm), which is consistent with the known actinomycete metabolites N-acetyl-β-oxotryptamine, mansouramycin A, sannanine and caerulomycin F. Since all were previously reported as produced by bacterial sources, no specific compound can be attributed to the ion detected.…”

Section: Chemical Analysis Of Bioactive Extractsmentioning

confidence: 99%

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Bioprospecting from cultivable bacterial communities of marine sediment and invertebrates from the underexplored Ubatuba region of Brazil

et al. 2016

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Shrimp fisheries along the Brazilian coast have significant environmental impact due to high by-catch rates (21 kg per kilogram of shrimp). Typically discarded, by-catch contains many invertebrates that may host a great variety of bacterial genera, some of which may produce bioactive natural products with biotechnological applications. Therefore, to utilize by-catch that is usually discarded we explored the biotechnological potential of culturable bacteria of two abundant by-catch invertebrate species, the snail Olivancillaria urceus and the sea star Luidia senegalensis. Sediment from the collection area was also investigated. Utilizing multiple isolation approaches, 134 isolates were obtained from the invertebrates and sediment. Small-subunit rRNA (16S) gene sequencing revealed that the isolates belonged to Proteobacteria, Firmicutes and Actinobacteria phyla and were distributed among 28 genera. Several genera known for their capacity to produce bioactive natural products (Micromonospora, Streptomyces, Serinicoccus and Verrucosispora) were retrieved from the invertebrate samples. To query the bacterial isolates for their ability to produce bioactive metabolites, all strains were fermented and fermentation extracts profiled by UP LC-HRMS and tested for antimicrobial activity. Four strains exhibited antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus warneri.

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Section: Discussionmentioning

confidence: 92%

Section: Chemical Analysis Of Bioactive Extractsmentioning

confidence: 99%

Bioprospecting from cultivable bacterial communities of marine sediment and invertebrates from the underexplored Ubatuba region of Brazil

et al. 2016

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“…The brasiliquinones A (119), B (120), C (121), and D (122) are new benz[a]anthraquinone antibiotics isolated from fermentations of Nocardia brasiliensis. 72, 102 All four compounds exhibited antimycobacterial activity towards M. smegmatis with MIC values of 0.39, 0.78, 12.5 and 12.5 µg ml Ϫ1 respectively. Mild cytotoxicity towards murine leukaemia cell lines L1210 and P388 was also observed, with IC 50 values of 2.9-11 µg ml Ϫ1 .…”

Section: Alkanes Alkenes Alkynes and Simple Aromaticsmentioning

confidence: 92%

Antimycobacterial natural products

Copp

2003

Nat. Prod. Rep.

183

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This review covers the literature published between January 1990 and December 2002 (inclusive) for natural products with reported antimycobacterial activity, with 248 citations to 352 compounds isolated from both terrestrial and marine sources The compounds are presented in order of chemical type, namely lipids/fatty acids and simple aromatics phenolics and acetogenic quinones, peptides, alkaloids, terpenes (monoterpenoids, diterpenes, sesquiterpenes, sesterterpenes and triterpenes) and steroids.

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“…Nemoto et al , in 1996 [ 209 ], investigated the antimicrobial and antitumor activities of three benz[a]anthraquinone derivatives, i.e. , brasiliquinones A, B, and C (isolated from the pathogenic strain Nocardia brasiliensis ), against LI210, P388, and drug resistant P388/ADR tumor cells .…”

Section: In Vitro Biological Activities Of Natumentioning

confidence: 99%

Anthraquinones and Derivatives from Marine-Derived Fungi: Structural Diversity and Selected Biological Activities

et al. 2016

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Anthraquinones and their derivatives constitute a large group of quinoid compounds with about 700 molecules described. They are widespread in fungi and their chemical diversity and biological activities recently attracted attention of industries in such fields as pharmaceuticals, clothes dyeing, and food colorants. Their positive and/or negative effect(s) due to the 9,10-anthracenedione structure and its substituents are still not clearly understood and their potential roles or effects on human health are today strongly discussed among scientists. As marine microorganisms recently appeared as producers of an astonishing variety of structurally unique secondary metabolites, they may represent a promising resource for identifying new candidates for therapeutic drugs or daily additives. Within this review, we investigate the present knowledge about the anthraquinones and derivatives listed to date from marine-derived filamentous fungi′s productions. This overview highlights the molecules which have been identified in microorganisms for the first time. The structures and colors of the anthraquinoid compounds come along with the known roles of some molecules in the life of the organisms. Some specific biological activities are also described. This may help to open doors towards innovative natural substances.

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Brasiliquinones A, B and C, New Benz(a)anthraquinone Antibiotics from Nocardia brasiliensis. I. Producing Strain, Isolation and Biological Activities of the Antibiotics.

Cited by 25 publications

References 11 publications

Bioprospecting from cultivable bacterial communities of marine sediment and invertebrates from the underexplored Ubatuba region of Brazil

Bioprospecting from cultivable bacterial communities of marine sediment and invertebrates from the underexplored Ubatuba region of Brazil

Antimycobacterial natural products

Anthraquinones and Derivatives from Marine-Derived Fungi: Structural Diversity and Selected Biological Activities

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