Determination of the structure of fusaproliferin by1H-NMR and distance geometry

Manetti, Cesare; Fogliano, Vincenzo; Ritieni, Alberto; Santini, Antonello; Randazzo, G.; Logrieco, A.; Segre, Anna Laura

doi:10.1007/bf02286446

Cited by 21 publications

(7 citation statements)

References 19 publications

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“…These results confirm the hypothesis proposed on the basis of molecular dynamics calculations and partially by 2D-NMR data. The configurations of the three CdC double bonds of the macrocyclic a Anisotropic thermal factors for refined atoms are given in the form of the isotropic equivalent displacement parameter defined as: This result, in contrast to that proposed in an earlier solution study 1 where a Z configuration for the C11dC12 double bond was claimed, confirms the molecular dynamics results 16 and is fully compatible with an isoprenoid biosynthetic pathway. The planes of two double bonds, C6dC7 and C11dC12, together with their substituents are nearly co-planar (the angle between the two average planes is 18°).…”

Section: Resultssupporting

confidence: 77%

Structure and Absolute Stereochemistry of Fusaproliferin, a Toxic Metabolite from Fusarium proliferatum

et al. 1996

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Fusaproliferin is a toxic sesterterpene isolated from Fusarium proliferatum, a widespread pathogen of cereals. Its absolute configuration has been determined by single crystal X-ray diffraction analysis. Fusaproliferin is considered to be a sesterterpene with a new ring skeleton having four C = C double bonds and four chiral atoms. The configurations of the four chiral atoms C10, C14, C15, and C19 are (R), (S), (R), and (S), respectively. In the solid state the macrolide shows a concave hydrophobic surface and hydrophilic convex face. The absolute configuration of C14 and C15 is the same as that observed for retigeranic acid, consistent with fusaproliferin being formed via a sesterterpenic-type biosynthetic pathway.

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Section: Resultssupporting

confidence: 77%

Structure and Absolute Stereochemistry of Fusaproliferin, a Toxic Metabolite from Fusarium proliferatum

et al. 1996

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“…Fusaproliferin is a toxic metabolite originally isolated from cultures of F. proliferatum (15,26,29). It is a sesterterpene compound that has toxic activity against brine shrimp (Artemia salina L.), insect cells, and human B lymphocytes and has teratogenic effects on chicken embryos (13,(26)(27)(28).…”

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confidence: 99%

Occurrence of Fusaproliferin and Beauvericin in Fusarium -Contaminated Livestock Feed in Iowa

Munkvold

Stahr

Logrieco³

et al. 1998

Appl Environ Microbiol

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Fusarium fungal contaminants and related mycotoxins were investigated in eight maize feed samples submitted to the Iowa State University Veterinary Diagnostic Laboratory. Fusarium moniliforme, F. proliferatum, and F. subglutinans were isolated from seven, eight, and five samples, respectively. These strains belonged to mating populations A, D, and E of the teleomorph Gibberella fujikuroi. Fusaproliferin was detected at concentrations of 0.1 to 30 μg/g in four samples, and beauvericin was detected (0.1 to 3.0 μg/g) in five samples. Fumonisins were detected in all eight samples (1.1 to 14 μg/g). Ten of 11 strains of F. proliferatum and all 12 strains ofF. subglutinans isolated from the samples produced fusaproliferin in culture on whole maize kernels (4 to 350 and 100 to 1,000 μg/g, respectively). Nine F. proliferatum strains also produced beauvericin in culture (85 to 350 μg/g), but none of the F. subglutinans strains produced beauvericin. Fumonisin B1 was produced by all nine F. moniliformestrains (50 to 2,000 μg/g) and by 10 of the F. proliferatum strains (1,000 to 2,000 μg/g). This is the first report of the natural occurrence of fusaproliferin outside Italy and of the natural occurrence of beauvericin in North America.

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“…In a brine shrimp (Artemia salina L.) bioassay, fusaproliferin was recognized as the major toxic component of organic extracts from maize cultures of ITEM-1494 (31). Further work has been devoted to elucidating the chemical structure of fusaproliferin (19,34). However, little information on its production by other Fusarium species and its toxicity has been available.…”

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Fusaproliferin production by Fusarium subglutinans and its toxicity to Artemia salina, SF-9 insect cells, and IARC/LCL 171 human B lymphocytes

Logrieco¹,

Moretti²,

Fornelli³

et al. 1996

Appl Environ Microbiol

124

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Fusarium subglutinans is an important pathogen of maize and other commodities worldwide. We examined MRC-115 and 71 other F. subglutinans strains from various geographic areas for their ability to synthesize fusaproliferin, a novel toxic sesterterpene recently isolated from F. proliferatum. Fusaproliferin production ranged from 30 to 1,500 g/g of dried ground substrate, with 33 strains producing more than 500 g/g. In particular, strain MRC-115 produced as much as 1,100 to 1,300 g/g. In toxicity studies of two invertebrate models, fusaproliferin was toxic to Artemia salina (50% lethal dose, 53.4 M) and to the lepidopteran cell line SF-9 (50% cytotoxic concentration, approximately 70 M, after a 48-h exposure). Fusaproliferin was also toxic to the human nonneoplastic B-lymphocyte cell line IARC/LCL 171 (50% cytotoxic concentration, approximately 55 M in culture in stationary phase after a 48-h exposure). Experiments performed with cells exposed at seeding suggested a possible cytostatic effect at subtoxic concentrations.

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Determination of the structure of fusaproliferin by1H-NMR and distance geometry

Cited by 21 publications

References 19 publications

Structure and Absolute Stereochemistry of Fusaproliferin, a Toxic Metabolite from Fusarium proliferatum

Structure and Absolute Stereochemistry of Fusaproliferin, a Toxic Metabolite from Fusarium proliferatum

Occurrence of Fusaproliferin and Beauvericin in Fusarium -Contaminated Livestock Feed in Iowa

Fusaproliferin production by Fusarium subglutinans and its toxicity to Artemia salina, SF-9 insect cells, and IARC/LCL 171 human B lymphocytes

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