Incorporation of Thiazolidine-4-Carbozylic Acid Into Ergosine by<i>Claviceps purpurea</i>

Baumert, A.; Erge, D.; Gröger, D.

doi:10.1055/s-2007-971418

Cited by 14 publications

(11 citation statements)

References 7 publications

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“…This step is thought to be followed by relatively nonspecific attachment of two additional amino acid units before the resulting tripeptide unit is linked to lysergic acid. Proline has been considered to play a key role in ergopeptide biosynthesis and, except for a report that l-thiazolidine-4-carboxylic acid will serve as a substitute (23), a proline residue has always been observed in the naturally occurring ergopeptines. Which specific amino acids are subsequently incorporated into the remainder of the peptide unit is at least partially controlled by the relative amino acid concentrations in the internal pool of the cells.…”

Section: Resultsmentioning

confidence: 99%

Ergobalansine, a New Ergot-Type Peptide Alkaloid Isolated from Cenchrus echinatus (Sandbur Grass) Infected with Balansia obtecta, and Produced in Liquid Cultures of B. obtecta and Balansia cyperi

Powell¹,

Plattner²,

Yates³

et al. 1990

J. Nat. Prod.

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An EtOH extract of Cenchrus echinatus (sandbur grass) infected with Balansia obtecta, a fungal endophyte of the Clavicipitaceae, has yielded ergobalansine [1], a new ergottype alkaloid. Ergobalansine is a peptide derivative of lysergic acid, but differs from other known ergopeptine alkaloids in that the characteristic proline residue has been replaced by an alanine residue. The structure of ergobalansine was determined by analysis of [H nmr, 13C nmr, and mass spectra of the parent compound and of the C-8 epimer (ergobalansinine [2]) and by comparison of these to spectra of the common ergopeptine alkaloids.Cenchrus echinatus L. (Gramineae) is an annual grass species native to the tropics or subtropics. It ranks highly among the world's worst weeds and has been reported as a serious pest in at least 18 crops in 35 countries (1). In the United States, Ce. echinatus is common along the South Atlantic and southern border area (2). Ce. echinatus is often referred to as sandbur, burgrass, or sandspur. When present as contaminants in feeds and hay, the burs of the seed heads reduce its acceptability and palatability for animals. Sandbur grass grows rapidly in sandy well-drained soils and often is found in cultivated fields, pastures, abandoned fields, and lawns, along roadsides, and along beaches. A search of the literature has revealed that there have been no detailed studies of the secondary metabolites of sandbur grass.Fungal endophytes of grasses, and ergot-like toxicity associated with endophyte-infected grasses, have become important topics during the last decade (3-5). Acremonium coenophialum and Acremonium lolii, the endophytes of tall fescue and perennial ryegrass,

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Section: Resultsmentioning

confidence: 99%

Ergobalansine, a New Ergot-Type Peptide Alkaloid Isolated from Cenchrus echinatus (Sandbur Grass) Infected with Balansia obtecta, and Produced in Liquid Cultures of B. obtecta and Balansia cyperi

Powell¹,

Plattner²,

Yates³

et al. 1990

J. Nat. Prod.

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“…Ergonorine [2] gave norvaline and proline in equal amounts by hydrolysis in HC1, and dimethylpyruvic acid by alkaline hydrolysis: this assigned 2 to the group of ergotoxine. Its field desorption mass spectrum (fdms) confirmed the mol wt with the molecular ion at mlz 561.…”

Section: And Discussionmentioning

confidence: 97%

“…The experiments performed by feeding norvaline to the strain of Claviceps purpurea 231 FI led to the isolation of three unnatural ergopeptine alkaloids, for which the names 1 R^Me, R2=»-Pr of ergorine [1], ergonorine [2], and ergonornorine [3] are proposed. These alkaloids form a new unnatural series having an «-propyl substituent at C-5' of the cyclol moiety.…”

Section: And Discussionmentioning

confidence: 99%

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Directed Biosynthesis of Unnatural Ergot Peptide Alkaloids

Perellino¹,

Małyszko²,

Ballabio³

et al. 1992

J. Nat. Prod.

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Three unnatural lysergic derivatives belonging to the class of ergopeptines have been obtained by feeding L-norvaline to a strain of Claviceps purpurea. Ergorine {!] corresponds to an analogue of ergovaline, and ergonorine {2} is an analogue of ergocornine; both have at C-5' an ß-propyl substituent instead of an isopropyl group. Ergonomorine [3] has the npropyl group at C-2' and C-5' as well. This alkaloid represents the first example of an ergopeptine having an unnatural amino acid in the first position of the cyclol moiety. Additional feeding experiments with natural and unnatural amino acids indicated the maximum possible size of the substitutent in the first position of the peptide moiety.All natural peptide ergot alkaloids are divided into two groups differing only in the extent of cyclization of their peptide moiety. The class of ergopeptine alkaloids is characterized by the presence of the cyclol, a tricyclic structure which is absent in the analogous ergopeptam alkaloids (Figure 1).

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“…So bauten Kulturen von Sphacelia sorghi bei der Inkubation mit allo-4-Hydroxy-prolin oder cis-4-Hydroxy-prolin die beiden Verbindungen zu einem geringen Prozentsatz in das Gerüst des 9,10-Dihydro-a-ergosins em, wobei die beiden epimeren 9'-Hydroxydihydroergosine der Formel 97 entstanden [73]. Der u-Ergosinstamm C. purpurea MUT 168/2 war sogar imstande, L-Thiazolidin-4-carbonsäure anstelle von L-Prolin zu verwerten und damit 2'(3-Methyl-S'a-isobutyl-9 ' -thiaergopeptin, 98, aufzubauen [74].…”

Section: Zur Biosynthese Der Ergotalkaloideunclassified

Neuere Ergebnisse der Mutterkornalkaloid-Forschung

Pa¹

1982

Planta Med

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Incorporation of Thiazolidine-4-Carbozylic Acid Into Ergosine byClaviceps purpurea

Cited by 14 publications

References 7 publications

Ergobalansine, a New Ergot-Type Peptide Alkaloid Isolated from Cenchrus echinatus (Sandbur Grass) Infected with Balansia obtecta, and Produced in Liquid Cultures of B. obtecta and Balansia cyperi

Ergobalansine, a New Ergot-Type Peptide Alkaloid Isolated from Cenchrus echinatus (Sandbur Grass) Infected with Balansia obtecta, and Produced in Liquid Cultures of B. obtecta and Balansia cyperi

Directed Biosynthesis of Unnatural Ergot Peptide Alkaloids

Neuere Ergebnisse der Mutterkornalkaloid-Forschung

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