Directed Biosynthesis of Unnatural Ergot Peptide Alkaloids

Perellino, Nicoletta Crespi; Małyszko, Jan; Ballabio, Marzia; Gioia, B.; Minghetti, A.

doi:10.1021/np50082a003

Cited by 16 publications

(3 citation statements)

References 4 publications

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“…The known "ergot alkaloids" produced by Clauiceps spp. may be divided into five major classes: the clavine, lysergic acid, simple lysergic acid amides, ergopeptine, and ergopeptam alkaloids (Berde and Schild, 1978;Perellino et al, 1992Perellino et al, , 1993. The ergopeptines, simple lysergic acid amides, and clavines (Figures 1, 5, and 6 ) have been isolated from A. coenophialum-infected tall fescue (Yates et al, 1985;Lyons et al, 1986;Petroski and Powell, 1991).…”

Section: A Coenophialum-infected Fescuementioning

confidence: 99%

Analysis of endophyte toxins: fescue and other grasses toxic to livestock

1995

Journal of Animal Science

162

110

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Research on livestock toxicoses caused by Acremonium (endophyte)-infected grasses strongly implicate the ergopeptine alkaloids with A. coenophialum-infected fescue and paxilline and the lolitrem alkaloids with A. lolii-infected perennial ryegrass as the causative agents. Isolation, identification, and detection of these toxins involves extraction with appropriate solvents, clean-up procedures, and chromatographic methods with known standards. Thin-layer, high-performance liquid and gas chromatography along with ultraviolet and mass spectrometric (i.e., electron impact, chemical ionization, tandem mass) characterizations have been reported. These methods have varying degrees of success depending on the matrix from which the alkaloids have been extracted. Ergovaline is the primary ergopeptine alkaloid isolated from cultures of A. coenophialum and also from infected fescue grass and seeds toxic to livestock. Other compounds isolated from the endophyte-infected fescue include: lysergic acid amide (ergine), the clavine class of ergot alkaloids (chanoclavine I, agroclavine, elymoclavine, penniclavine), the pyrrolizidine alkaloids (N-formylloline, N-acetylloline, N-methyloline, N-acetylnorloline), and the unique pyrrolopyrazine alkaloid peramine. The loline alkaloids and peramine have been more associated with the insect-deterrent properties of the endophyte-infected fescue than with livestock toxicoses. Also, both peramine and the ergopeptine alkaloids (ergovaline, ergotamine) have been isolated from A. lolii-infected perennial ryegrass. More recently, paxilline and lolitrem B have been detected in laboratory cultures of A. coenophialum isolated from tall fescue. The ergot alkaloids in endophyte-infected perennial ryegrass may be more related to decreased animal productivity (weight gains, reproduction problems), whereas the lolitrems cause the staggers syndrome. The detection, isolation, identification, and analyses of these compounds from Acremonium-infected grasses is presented.

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Section: A Coenophialum-infected Fescuementioning

confidence: 99%

Analysis of endophyte toxins: fescue and other grasses toxic to livestock

1995

Journal of Animal Science

162

110

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“…2). Since the alkaloid production depends primarily on the relative concentration of free amino acids in cells (Beacco et al, 1978;Bianchi et al, 1982;Crespi-Perellino et al, 1992;Cvak et al, 1996;Flieger et al, 1984;Keller et al, 1980), the comparison of the homo-Ile/Leu ratio in the amino acid pool, Table 3, with that in the corresponding alkaloids, i.e. Ergot alkaloids are synthetized by a multienzyme system extraribosomally (Maier et al, 1987).…”

Section: Discussionmentioning

confidence: 99%

Free and bonded homoisoleucine in sclerotia of the parasitic fungusClaviceps purpurea

et al. 1997

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Homoisoleucine, an unusual amino acid recently discovered in the structure of the ergopeptine alkaloid ergogaline, was determined in the parasitic fungus Claviceps purpurea Fr. (Tul.). growing on rye Secale cereale (L.) and in its host plant. Free homoisoleucine was detected by gas chromatography-mass spectrometry (GC-MS) in the amino acid pool of sclerotia of all fungal strains examined. Since homoisoleucine was not detected in rye, it seems that the amino acid is synthetized by the fungus. Furthermore, the ratio of leucine/homoisoleucine in the free amino acid pool of sclerotia is in good agreement with the ratio of the corresponding alkaloids a-ergokryptine/ ergogaline estimated by high performance liquid chromatography (HPLC). Thus, homoisoleucine is incorporated into the ergopeptines randomly with the similar specificity as leucine.

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“…:34 It was found that lochnericine (36) and lochnerinine (37) were metabolites, which were presumably sequentially formed. Metabolism of ajmaline (38) by cell cultures of R. serpentina has been found to yield raumacline (39) and its derivatives ( 40) and (41), which are new alkaloids. 35 Illustration is hereby provided of the ability of cell cultures to make new compounds which may be of biological interest and application.…”

Section: Terpenoid Indole Alkaloidsmentioning

confidence: 99%

The biosynthesis of plant alkaloids and nitrogenous microbial metabolites

Herbert¹

1995

Nat. Prod. Rep.

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Directed Biosynthesis of Unnatural Ergot Peptide Alkaloids

Cited by 16 publications

References 4 publications

Analysis of endophyte toxins: fescue and other grasses toxic to livestock

Analysis of endophyte toxins: fescue and other grasses toxic to livestock

Free and bonded homoisoleucine in sclerotia of the parasitic fungusClaviceps purpurea

The biosynthesis of plant alkaloids and nitrogenous microbial metabolites

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