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Literature summary extracted from

  • Martin, J.F.; Alvarez-Alvarez, R.; Liras, P.
    Clavine alkaloids gene clusters of Penicillium and related fungi evolutionary combination of prenyltransferases, monooxygenases and dioxygenases (2017), Genes (Basel), 8, 342 .
    View publication on PubMedView publication on EuropePMC

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+ Penicillium griseofulvum
-
 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+ Penicillium camemberti
-
 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+ Penicillium commune
-
 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+ Penicillium roqueforti
-
 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+ Aspergillus fumigatus
-
 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+ Penicillium expansum
-
 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+ Penicillium steckii
-
 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+ Penicillium roqueforti FM164
-
 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+ Aspergillus fumigatus CBS 101355
-
 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+ Aspergillus fumigatus ATCC MYA-4609
-
 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+ Aspergillus fumigatus FGSC A1100
-
 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+ Aspergillus fumigatus Af293
-
 festuclavine + NAD+
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.5.1.44 Aspergillus fumigatus Q4WZ69 Aspergillus fumigatus
-
1.5.1.44 Aspergillus fumigatus Af293 Q4WZ69 Aspergillus fumigatus
-
1.5.1.44 Aspergillus fumigatus ATCC MYA-4609 Q4WZ69 Aspergillus fumigatus
-
1.5.1.44 Aspergillus fumigatus CBS 101355 Q4WZ69 Aspergillus fumigatus
-
1.5.1.44 Aspergillus fumigatus FGSC A1100 Q4WZ69 Aspergillus fumigatus
-
1.5.1.44 Penicillium camemberti
-
-
-
1.5.1.44 Penicillium commune I6U936
-
-
1.5.1.44 Penicillium expansum A0A0A2J928
-
-
1.5.1.44 Penicillium griseofulvum
-
-
-
1.5.1.44 Penicillium roqueforti W6Q1E9
-
-
1.5.1.44 Penicillium roqueforti W6QRI9
-
-
1.5.1.44 Penicillium roqueforti FM164 W6Q1E9
-
-
1.5.1.44 Penicillium roqueforti FM164 W6QRI9
-
-
1.5.1.44 Penicillium steckii A0A1V6SJK0
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+
-
 Penicillium griseofulvum festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+
-
 Penicillium camemberti festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+
-
 Penicillium commune festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+
-
 Penicillium roqueforti festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+
-
 Aspergillus fumigatus festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+
-
 Penicillium expansum festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+
-
 Penicillium steckii festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+
-
 Penicillium roqueforti FM164 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+
-
 Aspergillus fumigatus CBS 101355 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+
-
 Aspergillus fumigatus ATCC MYA-4609 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+
-
 Aspergillus fumigatus FGSC A1100 festuclavine + NAD+
-
 ?
1.5.1.44 6,8-dimethyl-6,7-didehydroergoline + NADH + H+
-
 Aspergillus fumigatus Af293 festuclavine + NAD+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.5.1.44 EasG
-
 Aspergillus fumigatus
1.5.1.44 ergot alkaloid biosynthetic protein G UniProt Aspergillus fumigatus
1.5.1.44 festuclavine synthase
-
 Penicillium commune
1.5.1.44 festuclavine synthase I
-
 Penicillium roqueforti
1.5.1.44 festuclavine synthase II
-
 Penicillium roqueforti
1.5.1.44 FgaFS
-
 Aspergillus fumigatus
1.5.1.44 FgaFS
-
 Penicillium commune
1.5.1.44 FgaFS UniProt Penicillium commune
1.5.1.44 ifgF1
-
 Penicillium roqueforti
1.5.1.44 ifgF2
-
 Penicillium roqueforti
1.5.1.44 isofumigaclavine biosynthesis cluster A protein F1 UniProt Penicillium roqueforti
1.5.1.44 isofumigaclavine biosynthesis cluster A protein F2 UniProt Penicillium roqueforti

Cofactor

EC Number Cofactor Comment Organism Structure
1.5.1.44 NADH
-
 Penicillium griseofulvum
1.5.1.44 NADH
-
 Penicillium camemberti
1.5.1.44 NADH
-
 Penicillium commune
1.5.1.44 NADH
-
 Penicillium roqueforti
1.5.1.44 NADH
-
 Aspergillus fumigatus
1.5.1.44 NADH
-
 Penicillium expansum
1.5.1.44 NADH
-
 Penicillium steckii

General Information

EC Number General Information Comment Organism
1.5.1.44 evolution organization of the clavine gene clusters in different species, e.g. clusters A and B of isofumigaclavine in Penicillium roqueforti, overview Penicillium roqueforti
1.5.1.44 evolution organization of the clavine gene clusters in different species, e.g. fumigaclavine A gene cluster of Penicillium commune, overview Penicillium commune
1.5.1.44 evolution organization of the clavine gene clusters in different species, e.g. fumigaclavine C gene cluster in Neosartorya fumigata, overview Aspergillus fumigatus
1.5.1.44 evolution organization of the clavine gene clusters in different species, overview Penicillium camemberti
1.5.1.44 malfunction accumulation of prenylated intermediates and lack of fumigaclavine A formation has been reported in mutants of Neosartorya fumigata disrupted in the festuclavine hydroxylase Aspergillus fumigatus
1.5.1.44 metabolism clavine and lysergic acid-containing alkaloids derive from the condensation of tryptophan and dimethylallylpyrophosphate (DMA-PP), catalyzed by the first enzyme of the pathway, named dimethylallyltryptophan synthase (DMATS). This results in the formation of tricyclic intermediates, the most relevant being chanoclavine I and chanoclavine I aldehyde, which the branch point intermediate for the formation of different types of alkaloids. Chanoclavine I aldehyde, is later cyclized to form the tetracyclic ergoline nucleus. The ergoline structure constitutes the nucleus of festuclavine, agroclavine, elymoclavine, pyroclavine and their derivatives. In agroclavine and elymoclavine, there is a double bond between carbons C-8 and C-9, whereas in festuclavine this double bond is not present. Pyroclavine, an C-8 stereoisomer (carbons 8R/9S) of festuclavine (carbon 8S/9S), is also present in cultures of some of the clavine alkaloids producers. The late steps of the biosynthesis of fumigaclavine alkaloids involve the oxidation of festuclavine to 9-hydroxyfestuclavine (named fumigaclavine B) and later the acetylation of fumigaclavine B to fumigaclavine A. Comparison of the synthetic pathway of isofumigaclavine A in Penicillium roqueforti and fumigaclavine C in Neosartorya fumigata Penicillium roqueforti
1.5.1.44 metabolism clavine and lysergic acid-containing alkaloids derive from the condensation of tryptophan and dimethylallylpyrophosphate (DMA-PP), catalyzed by the first enzyme of the pathway, named dimethylallyltryptophan synthase (DMATS). This results in the formation of tricyclic intermediates, the most relevant being chanoclavine I and chanoclavine I aldehyde, which the branch point intermediate for the formation of different types of alkaloids. Chanoclavine I aldehyde, is later cyclized to form the tetracyclic ergoline nucleus. The ergoline structure constitutes the nucleus of festuclavine, agroclavine, elymoclavine, pyroclavine and their derivatives. In agroclavine and elymoclavine, there is a double bond between carbons C-8 and C-9, whereas in festuclavine this double bond is not present. Pyroclavine, an C-8 stereoisomer (carbons 8R/9S) of festuclavine (carbon 8S/9S), is also present in cultures of some of the clavine alkaloids producers. The late steps of the biosynthesis of fumigaclavine alkaloids involve the oxidation of festuclavine to 9-hydroxyfestuclavine (named fumigaclavine B) and later the acetylation of fumigaclavine B to fumigaclavine A. Finally, in Neosartorya fumigata, there is a step that involves the prenylation of fumigaclavine A to form fumigaclavine C. Comparison of the synthetic pathway of isofumigaclavine A in Penicillium roqueforti and fumigaclavine C in Neosartorya fumigata Aspergillus fumigatus
1.5.1.44 metabolism clavine and lysergic acid-containing alkaloids derive from the condensation of tryptophan and dimethylallylpyrophosphate (DMA-PP), catalyzed by the first enzyme of the pathway, named dimethylallyltryptophan synthase (DMATS). This results in the formation of tricyclic intermediates, the most relevant being chanoclavine I and chanoclavine I aldehyde, which the branch point intermediate for the formation of different types of alkaloids. Chanoclavine I aldehyde, is later cyclized to form the tetracyclic ergoline nucleus. The ergoline structure constitutes the nucleus of festuclavine, agroclavine, elymoclavine, pyroclavine and their derivatives. In agroclavine and elymoclavine, there is a double bond between carbons C-8 and C-9, whereas in festuclavine this double bond is not present. Pyroclavine, an C-8 stereoisomer (carbons 8R/9S) of festuclavine (carbon 8S/9S), is also present in cultures of some of the clavine alkaloids producers. The late steps of the biosynthesis of fumigaclavine alkaloids involve the oxidation of festuclavine to 9-hydroxyfestuclavine (named fumigaclavine B) and later the acetylation of fumigaclavine B to fumigaclavine A Penicillium griseofulvum
1.5.1.44 metabolism clavine and lysergic acid-containing alkaloids derive from the condensation of tryptophan and dimethylallylpyrophosphate (DMA-PP), catalyzed by the first enzyme of the pathway, named dimethylallyltryptophan synthase (DMATS). This results in the formation of tricyclic intermediates, the most relevant being chanoclavine I and chanoclavine I aldehyde, which the branch point intermediate for the formation of different types of alkaloids. Chanoclavine I aldehyde, is later cyclized to form the tetracyclic ergoline nucleus. The ergoline structure constitutes the nucleus of festuclavine, agroclavine, elymoclavine, pyroclavine and their derivatives. In agroclavine and elymoclavine, there is a double bond between carbons C-8 and C-9, whereas in festuclavine this double bond is not present. Pyroclavine, an C-8 stereoisomer (carbons 8R/9S) of festuclavine (carbon 8S/9S), is also present in cultures of some of the clavine alkaloids producers. The late steps of the biosynthesis of fumigaclavine alkaloids involve the oxidation of festuclavine to 9-hydroxyfestuclavine (named fumigaclavine B) and later the acetylation of fumigaclavine B to fumigaclavine A Penicillium camemberti
1.5.1.44 metabolism clavine and lysergic acid-containing alkaloids derive from the condensation of tryptophan and dimethylallylpyrophosphate (DMA-PP), catalyzed by the first enzyme of the pathway, named dimethylallyltryptophan synthase (DMATS). This results in the formation of tricyclic intermediates, the most relevant being chanoclavine I and chanoclavine I aldehyde, which the branch point intermediate for the formation of different types of alkaloids. Chanoclavine I aldehyde, is later cyclized to form the tetracyclic ergoline nucleus. The ergoline structure constitutes the nucleus of festuclavine, agroclavine, elymoclavine, pyroclavine and their derivatives. In agroclavine and elymoclavine, there is a double bond between carbons C-8 and C-9, whereas in festuclavine this double bond is not present. Pyroclavine, an C-8 stereoisomer (carbons 8R/9S) of festuclavine (carbon 8S/9S), is also present in cultures of some of the clavine alkaloids producers. The late steps of the biosynthesis of fumigaclavine alkaloids involve the oxidation of festuclavine to 9-hydroxyfestuclavine (named fumigaclavine B) and later the acetylation of fumigaclavine B to fumigaclavine A Penicillium commune
1.5.1.44 metabolism clavine and lysergic acid-containing alkaloids derive from the condensation of tryptophan and dimethylallylpyrophosphate (DMA-PP), catalyzed by the first enzyme of the pathway, named dimethylallyltryptophan synthase (DMATS). This results in the formation of tricyclic intermediates, the most relevant being chanoclavine I and chanoclavine I aldehyde, which the branch point intermediate for the formation of different types of alkaloids. Chanoclavine I aldehyde, is later cyclized to form the tetracyclic ergoline nucleus. The ergoline structure constitutes the nucleus of festuclavine, agroclavine, elymoclavine, pyroclavine and their derivatives. In agroclavine and elymoclavine, there is a double bond between carbons C-8 and C-9, whereas in festuclavine this double bond is not present. Pyroclavine, an C-8 stereoisomer (carbons 8R/9S) of festuclavine (carbon 8S/9S), is also present in cultures of some of the clavine alkaloids producers. The late steps of the biosynthesis of fumigaclavine alkaloids involve the oxidation of festuclavine to 9-hydroxyfestuclavine (named fumigaclavine B) and later the acetylation of fumigaclavine B to fumigaclavine A Penicillium expansum
1.5.1.44 metabolism clavine and lysergic acid-containing alkaloids derive from the condensation of tryptophan and dimethylallylpyrophosphate (DMA-PP), catalyzed by the first enzyme of the pathway, named dimethylallyltryptophan synthase (DMATS). This results in the formation of tricyclic intermediates, the most relevant being chanoclavine I and chanoclavine I aldehyde, which the branch point intermediate for the formation of different types of alkaloids. Chanoclavine I aldehyde, is later cyclized to form the tetracyclic ergoline nucleus. The ergoline structure constitutes the nucleus of festuclavine, agroclavine, elymoclavine, pyroclavine and their derivatives. In agroclavine and elymoclavine, there is a double bond between carbons C-8 and C-9, whereas in festuclavine this double bond is not present. Pyroclavine, an C-8 stereoisomer (carbons 8R/9S) of festuclavine (carbon 8S/9S), is also present in cultures of some of the clavine alkaloids producers. The late steps of the biosynthesis of fumigaclavine alkaloids involve the oxidation of festuclavine to 9-hydroxyfestuclavine (named fumigaclavine B) and later the acetylation of fumigaclavine B to fumigaclavine A Penicillium steckii
1.5.1.44 physiological function gene ifgF1 encodes a festuclavine synthase that is involved in the conversion of chanoclavine I aldehyde into festuclavine Penicillium roqueforti