Spirodionic Acid, a Novel Metabolite from <i>Streptomyces</i> sp., Part 1: Structure Elucidation and Diels–Alder‐Type Biosynthesis

Textor, Adriana; Papastavrou, Ina; Siewert, Jiirgen; Magull, Jörg; Kulik, Andreas; Fiedler, Hans‐Peter; Zezschwitz, Paultheo von; Grond, Stephanie

doi:10.1002/chem.200601687

Cited by 12 publications

(25 citation statements)

References 46 publications

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“…In addition to the phenazines and pyrones, a diastereomeric mixture of dihydrosarkomycins was also identified 13, 15. The collection of diverse metabolites in the ICBB8198 strain paralleled that of the spirodionic acid producer, Streptomyces sp.…”

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confidence: 89%

“…The collection of diverse metabolites in the ICBB8198 strain paralleled that of the spirodionic acid producer, Streptomyces sp. Tü6077, which produced griseoluteic acid, griseolutein, dihydrosarkomycin, and pyrone 4a , in addition to spirodionic acid 13. This similarity in metabolite production with the ICBB8198 strain led us to re-examine the extract for the presence of spirodionic acid.…”

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confidence: 95%

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Modified Phenazines from an Indonesian Streptomyces sp.

et al. 2010

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Fractionation of the extract from the Indonesian Streptomyces sp. ICBB8198 as directed by the antibacterial activity delivered the known phenazine antibiotics griseoluteic acid (1a) and griseolutein A (1b), as well as two new phenazine derivatives (2 and 3). In addition, the known compounds spirodionic acid, dihydrosarkomycins, and 6-ethyl-4-hydroxy-3,5-dimethyl-2H-pyran-2-one (4a), along with the new pyrone, 3,6-diethyl-4-hydroxy-5-methyl-2H-pyran-2-one (4b), were isolated. We report here the isolation, structure elucidation, and antibiotic activity of the new metabolites as well as a hypothetical pathway for the formation of the new phenazine derivatives.

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confidence: 89%

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confidence: 95%

Modified Phenazines from an Indonesian Streptomyces sp.

et al. 2010

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“…In 2007, spirodionic acid ( 5 ) was reported as a new secondary metabolite from Streptomyces sp.,18 and we have achieved its first racemic total synthesis starting from rac ‐3‐ethenyl‐1‐trimethylsilyloxycyclopentene ( cf. structure 4 , R=H) 19.…”

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confidence: 99%

Production of detoxified sorghum straw hydrolysates for fermentative purposes

et al. 2006

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Sorghum straw can be hydrolysed to obtain monosaccharide solutions, mainly containing xylose. The usual biotechnological application of xylose is its bioconversion to xylitol. The global process from straw to xylitol can give an added value to the sorghum straw. The process has the following sequential steps: reduction of size, acid hydrolysis, neutralization, detoxification, fermentation, recovery and purification. This work deals with the optimization of the detoxification process of sorghum straw hydrolysates with activated charcoal. The variables evaluated were pH (1-5), contact time (20-60 min) and activated charcoal charge (20-33 g kg −1 ). Mathematical models were obtained through a factorial experimental design. The models suggest that optimal conditions for detoxification are pH 1, contact time of 29 min and a charcoal charge of 33 g kg −1 . These conditions allowed hydrolysates with 54.2 g xylose L −1 , 13.5 g glucose L −1 , 12 g arabinose L −1 , 0.2 g furfural L −1 and 0.0 g acetic acid L −1 to be obtained. The results suggest that performing the detoxification step before the neutralization step gave the best outcome. Fermentations by Candida parapsilosis NRRL Y-2315 were performed and it was confirmed that the treated hydrolysate is suitable for xylitol production, yielding up to 17 g L −1 of this polyol.

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“…The proposed intermolecular Diels–Alder step joining the two polyketide fragments to create the cyclohexene ring of 1 is of particular interest. While intramolecular Diels–Alder reactions in the biosynthesis of secondary metabolites are well-documented, − the involvement of intermolecular Diels–Alder reactions in the biosynthesis of natural products is much less common. − Such reactions are more likely to involve Diels–Alderases since diene–dienophile interactions should be less effective when the substrates are separated, compared with the intramolecular version of such reactions, for which the molecular constraints often facilitate a non-enzymatic spontaneous reactivity.…”

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Structure and Biogenesis of Roussoellatide, a Dichlorinated Polyketide from the Marine-Derived Fungus Roussoella sp. DLM33

et al. 2015

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The structure of the fungal metabolite roussoellatide (1) has been established by spectroscopic and X-ray diffraction analyses. Results from feeding experiments with [1-(13)C]acetate, [2-(13)C]acetate, and [1,2-(13)C]acetate were consistent with a biosynthetic pathway to the unprecedented skeleton of 1 involving Favorskii rearrangements in separate pentaketides, subsequently joined via an intermolecular Diels-Alder reaction.

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Spirodionic Acid, a Novel Metabolite from Streptomyces sp., Part 1: Structure Elucidation and Diels–Alder‐Type Biosynthesis

Cited by 12 publications

References 46 publications

Modified Phenazines from an Indonesian Streptomyces sp.

Modified Phenazines from an Indonesian Streptomyces sp.

Production of detoxified sorghum straw hydrolysates for fermentative purposes

Structure and Biogenesis of Roussoellatide, a Dichlorinated Polyketide from the Marine-Derived Fungus Roussoella sp. DLM33

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