The Structures of Fluostatins C, D and E, Novel Members of the Fluostatin Family

Schneider, Kathrin; Nicholson, Graeme; Ströbele, Markus; Baur, Stephanie; Niehaus, Jörg; Fiedler, Hans‐Peter; Süssmuth, Roderich D.

doi:10.1038/ja.2006.15

Cited by 30 publications

(24 citation statements)

References 10 publications

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“…High-resolution FTICR-MS of the main metabolite gave an exact mass of 324.05650 Da which corresponded to the molecular formula C 18 H 12 O 6 (1). Structural data on the isolated metabolites from strain Acta 1383 [3] showed a relationship to fluostatins A (4) and B (5); the latter are inhibitors of dipeptidyl peptidase III produced by a member of the genus Streptomyces [4,5]. The structures of the fluostatins are shown in Fig.…”

Section: Introductionmentioning

confidence: 99%

“…Fluostatin A (4) was not observed in all of the fermentations of strain Acta 1383 or in all of the isolation trials. The structures of the novel fluostatins CϳE were elucidated as described in a previous report [3]. The physico-chemical properties of the compounds are summarized in Table 1.…”

Section: Isolation and Physico-chemical Propertiesmentioning

confidence: 99%

“…Batch fermentations of strain Acta 1383 were carried out in a 20-liter fermentor equipped with a turbine impellor system in a medium consisting of soluble starch 20 g, KNO 3 5 g, K 2 HPO 4 0.5 g, NaCl 0.5 g, MgSO 4 · 7H 2 O 0.5 g and FeSO 4 · 7H 2 O 0.01 g in 1.0 liter deionized water. The fermentor was inoculated with 5% by volume of a shake flask culture, grown at 27°C in 500 ml-Erlenmeyer flasks with one baffle for 48 hours on a rotary shaker at 120 rpm.…”

Section: Fermentation and Isolationmentioning

confidence: 99%

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Fluostatins C∼E, Novel Members of the Fluostatin Family Produced by Streptomyces Strain Acta 1383

et al. 2006

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Three new members of the fluostatin family, fluostatins CϳE, were discovered in a culture filtrate extract of strain Acta 1383 during an HPLC screening program. The producing strain belongs to the genus Streptomyces and is closely related to type strains classified in the Streptomyces lavendulae 16S rRNA subclade. Fluostatins are named by their characteristic fluorenone chromophore. Fluostatin C shows moderate activity against selected human tumor cell lines.

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Section: Introductionmentioning

confidence: 99%

Section: Isolation and Physico-chemical Propertiesmentioning

confidence: 99%

Section: Fermentation and Isolationmentioning

confidence: 99%

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Fluostatins C∼E, Novel Members of the Fluostatin Family Produced by Streptomyces Strain Acta 1383

et al. 2006

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“…In anoxic mangrove rhizosphere, Actinobacterial species such as Streptomyces, Micromonospora, and Nocardioform were found to be abundant, which is 1000 to 10000 times smaller than arable lands because of tidal influence [2]. Similarly, Nocardia isolated from mangrove soil produced new cytotoxic metabolites that strongly inhibited human cell lines, such as gastric adenocarcinoma [3]. Dessert soil is also considered as an extreme terrestrial environment where only certain species, especially wherein Actinobacteria, often use Microcoleus as a source of food.…”

Section: Terrestrial Environmentmentioning

confidence: 99%

An Introduction to Actinobacteria

Ranjani¹,

Dhanasekaran²,

Gopinath³

2016

Actinobacteria - Basics and Biotechnological Applications

102

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Actinobacteria, which share the characteristics of both bacteria and fungi, are widely distributed in both terrestrial and aquatic ecosystems, mainly in soil, where they play an essential role in recycling refractory biomaterials by decomposing complex mixtures of polymers in dead plants and animals and fungal materials. They are considered as the biotechnologically valuable bacteria that are exploited for its secondary metabolite production. Approximately, 10,000 bioactive metabolites are produced by Actinobacteria, which is 45% of all bioactive microbial metabolites discovered. Especially Streptomyces species produce industrially important microorganisms as they are a rich source of several useful bioactive natural products with potential applications. Though it has various applications, some Actinobacteria have its own negative effect against plants, animals, and humans. On this context, this chapter summarizes the general characteristics of Actinobacteria, its habitat, systematic classification, various biotechnological applications, and negative impact on plants and animals.

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“…Until now, there have been 16 fluostatin analogues discovered from terrestrial and marine actinomycetes [ 22 , 23 , 24 , 25 , 26 ] or heterologous expression of environmental DNAs [ 27 ]. Compared to known fluostatins, compounds 1 – 5 contain different methoxy group attached at C-7; compounds 2 – 5 contain different hydroxy group attached at C-4; and compound 4 contains high oxidized A-ring with four hydroxy groups attached at C-1, C-2, C-3 and C-4.…”

Section: Resultsmentioning

confidence: 99%

Fluostatins M–Q Featuring a 6-5-6-6 Ring Skeleton and High Oxidized A-Rings from Marine Streptomyces sp. PKU-MA00045

et al. 2018

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Aromatic polyketides from marine actinomycetes have received increasing attention due to their unusual structures and potent bioactivities. Compared to their terrestrial counterparts, marine aromatic polyketides have been less discovered and their structural and biological diversities are far from being fully investigated. In this study, we employed a PCR-based genome mining method to discover aromatic polyketides in our marine bacteria collection. Five new atypical angucyclinones, fluostatins M–Q (1–5) featuring a unique 6-5-6-6 ring skeleton, were discovered from one “positive” Streptomyces sp. PKU-MA00045. The structures of fluostatins M–Q (1–5) were elucidated based on comprehensive spectroscopic analyses and the crystallographic structure of fluostatin P (4), which contains the most oxidized A-ring, was solved by X-ray diffraction analysis with Cu Kα radiation. Compared to the published 16 fluostatin analogues, fluostatins M–Q (1–5) contained a different methoxy group attached at C-7 and hydroxy group attached at C-4, enriching the structural diversity of aromatic polyketides from marine actinomycetes. Genome sequencing of Streptomyces sp. PKU-MA00045 revealed the biosynthetic gene cluster of fluostatins M–Q (1–5), which contained different genes and gene organizations compared to known fluostatin gene clusters, facilitating the investigation of the biosynthesis of the unique 6-5-6-6 ring skeleton in all fluostatins.

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The Structures of Fluostatins C, D and E, Novel Members of the Fluostatin Family

Cited by 30 publications

References 10 publications

Fluostatins C∼E, Novel Members of the Fluostatin Family Produced by Streptomyces Strain Acta 1383

Fluostatins C∼E, Novel Members of the Fluostatin Family Produced by Streptomyces Strain Acta 1383

An Introduction to Actinobacteria

Fluostatins M–Q Featuring a 6-5-6-6 Ring Skeleton and High Oxidized A-Rings from Marine Streptomyces sp. PKU-MA00045

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