scholarly journals Total synthesis, biosynthesis and biological profiles of clavine alkaloids

2016 ◽  
Vol 14 (25) ◽  
pp. 5894-5913 ◽  
Author(s):  
Stephanie R. McCabe ◽  
Peter Wipf
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloids ◽  
Clavine Alkaloids ◽  
Biological Aspects

This review highlights noteworthy synthetic and biological aspects of the clavine subfamily of ergot alkaloids.

Isolation of ergovaline, ergoptine, and ergonine, new alkaloids of the peptide type, from ergot sclerotia

1979 ◽  
Vol 57 (13) ◽  
pp. 1638-1641 ◽  
Author(s):  
Rudolf Brunner ◽  
Peter Leopold Stütz ◽  
Hans Tscherter ◽  
Paul Albert Stadler
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloid ◽  
Ergot Alkaloids ◽  
Extraction Processes

The isolation of three new ergot alkaloids of the peptide type from sclerotia of Clavicepspurpurea and from mother liquors of rye ergot alkaloid extraction processes is described. The constitution of the new alkaloids ergovaline, ergoptine, and ergonine has been established by comparison with compounds previously obtained by total synthesis.

ChemInform Abstract: Photocyclization of Enamides. Part 29. Dehydrogenation with Benzeneseleninic Anhydride in the Total Synthesis of Ergot Alkaloids.

ChemInform ◽  
1990 ◽  
Vol 21 (27) ◽  
Author(s):  
I. NINOMIYA ◽  
C. HASHIMOTO ◽  
T. KIGUCHI ◽  
T. NAITO ◽  
D. H. R. BARTON ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloids

Dehydrogenation with Benzeneseleninic Anhydride in the Total Synthesis of Ergot Alkaloids

1996 ◽  
pp. 529-532
Author(s):  
Ichiya Ninomiya ◽  
Chiyomi Hashimoto ◽  
Toshiko Kiguchi ◽  
Takeaki Naito ◽  
Derek H. R. Barton ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloids

Dehydrogenation with phenylseleninic anhydride in the total synthesis of ergot alkaloids

1985 ◽  
Vol 26 (35) ◽  
pp. 4187-4190 ◽  
Author(s):  
Ichiya Ninomiya ◽  
Chiyomi Hashimoto ◽  
Toshiko Kiguchi ◽  
Derek H.R. Barton ◽  
Xavier Lusinchi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloids

New Routes to Clavine-type Ergot Alkaloids. Part 1. First Total Synthesis of Three Natural Products: (+)-Setoclavine, (+)-Isosetoclavine, (-)-9,10-Dihydroisosetoclavine, and Structure Correction of the Latter

Heterocycles ◽  
2006 ◽  
Vol 67 (1) ◽  
pp. 291 ◽  
Author(s):  
István Moldvai ◽  
Eszter Temesvári-Major ◽  
Eszter Gács-Baitz ◽  
Mária Incze ◽  
Gábor Dörnyei ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Ergot Alkaloids

Total Synthesis of Ergot Alkaloids, (±)-Elymoclavine and (±)-Isolysergol

Heterocycles ◽  
1984 ◽  
Vol 22 (5) ◽  
pp. 1035 ◽  
Author(s):  
Ichiya Ninomiya ◽  
Chiyomi Hashimoto ◽  
Toshiko Kiguchi
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloids

scholarly journals Alkaloid Cluster Gene ccsA of the Ergot Fungus Claviceps purpurea Encodes Chanoclavine I Synthase, a Flavin Adenine Dinucleotide-Containing Oxidoreductase Mediating the Transformation of N-Methyl-Dimethylallyltryptophan to Chanoclavine I

2010 ◽  
Vol 76 (6) ◽  
pp. 1822-1830 ◽  
Author(s):  
Nicole Lorenz ◽  
Jana Olšovská ◽  
Miroslav Šulc ◽  
Paul Tudzynski
Keyword(s):  
Flavin Adenine Dinucleotide ◽  
Axenic Culture ◽  
Ergot Alkaloids ◽  
Claviceps Purpurea ◽  
Alkaloid Biosynthesis ◽  
Fusion Construct ◽  
Knockout Mutants ◽  
Clavine Alkaloids ◽  
Functional Analyses ◽  
Layer Chromatography

ABSTRACT Ergot alkaloids are indole-derived secondary metabolites synthesized by the phytopathogenic ascomycete Claviceps purpurea. In wild-type strains, they are exclusively produced in the sclerotium, a hibernation structure; for biotechnological applications, submerse production strains have been generated by mutagenesis. It was shown previously that the enzymes specific for alkaloid biosynthesis are encoded by a gene cluster of 68.5 kb. This ergot alkaloid cluster consists of 14 genes coregulated and expressed under alkaloid-producing conditions. Although the role of some of the cluster genes in alkaloid biosynthesis could be confirmed by a targeted knockout approach, further functional analyses are needed, especially concerning the early pathway-specific steps up to the production of clavine alkaloids. Therefore, the gene ccsA, originally named easE and preliminarily annotated as coding for a flavin adenine dinucleotide-containing oxidoreductase, was deleted in the C. purpurea strain P1, which is able to synthesize ergot alkaloids in axenic culture. Five independent knockout mutants were analyzed with regard to alkaloid-producing capability. Thin-layer chromatography (TLC), ultrapressure liquid chromatography (UPLC), and mass spectrometry (MS) analyses revealed accumulation of N-methyl-dimethylallyltryptophan (Me-DMAT) and traces of dimethylallyltryptophan (DMAT), the first pathway-specific intermediate. Since other alkaloid intermediates could not be detected, we conclude that deletion of ccsA led to a block in alkaloid biosynthesis beyond Me-DMAT formation. Complementation with a ccsA/gfp fusion construct restored alkaloid biosynthesis. These data indicate that ccsA encodes the chanoclavine I synthase or a component thereof catalyzing the conversion of N-methyl-dimethylallyltryptophan to chanoclavine I.

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