Isolation and identification of 6,7-seco-agroclavine from Claviceps purpurea

Phytochemistry
1979.0

Abstract

Agroclavine 1 and elymoclavine 2 are the major clavine alkaloids from Claviceps purpurea strain AA-218. Analysis of the crude fermentation product by TLC showed 5 additional minor components positive to Allport and Cocking's reagent. The two most prominent minor alkaloids (3 and 4) were purified by HPLC followed by PLC. Compound 4 was identified as setoclavine via comparison of PMR, IR, UV, and mass spectral data with published values. Compound 3 was identified as 6,7-seco-agroclavine based on IR, UV, PMR, and mass spectral data and its identity with a synthetic sample from agroclavine. The biosynthetic origin of compound 3 was discussed: while its role in clavine biosynthesis is not ruled out, it appears more likely a reductive metabolite of agroclavine, supported by the ease of chemical cleavage of the 6,7-bond in agroclavine and feeding experiments excluding its incorporation into major clavines.

Knowledge Graph

Similar Paper

Isolation and identification of 6,7-seco-agroclavine from Claviceps purpurea
Phytochemistry 1979.0
New insights into ergot alkaloid biosynthesis in Claviceps purpurea: An agroclavine synthase EasG catalyses, via a non-enzymatic adduct with reduced glutathione, the conversion of chanoclavine-I aldehyde to agroclavine
Organic & Biomolecular Chemistry 2011.0
Two Unusual Ergopeptines Produced by a Saprophytic Culture of Claviceps purpurea
Journal of Natural Products 1987.0
Two Unusual Ergopeptines Produced by a Saprophytic Culture of Claviceps purpurea
Journal of Natural Products 1987.0
On the New Peptide-Type Ergot Alkaloids, Ergosecaline and Ergosecalinine
Bulletin of the Agricultural Chemical Society of Japan 1959.0
Drei neue Mutterkornalkaloide aus saprophytischen Kulturen von Claviceps paspali Stevens et Hall. 77. Mitteilung über Mutterkornalkaloide [1]
Helvetica Chimica Acta 1974.0
Isolation and structure elucidation of 6-(3'-methylbuten-2'-yl)isatin, an unusual metabolite from Streptomyces albus.
The Journal of Antibiotics 1986.0
Drei neue Mutterkornalkaloide aus saprophytischen Kulturen von <i>Claviceps paspali Stevens et Hall</i>. 77. Mitteilung über Mutterkornalkaloide [1]
Helvetica Chimica Acta 1974.0
Lactam ergot alkaloids (ergopeptams) as predominant alkaloids in sclerotia of Claviceps purpurea from Norwegian wild grasses
Toxicon 2008.0
Lactam ergot alkaloids (ergopeptams) as predominant alkaloids in sclerotia of Claviceps purpurea from Norwegian wild grasses
Toxicon 2008.0