Progress and Prospects of Ergot Alkaloid Research
11
Table 2. Application of different feeding strategies in the directed biosynthesis of Claviceps
Synthon
Incorporation strategy
Target/Objective
Reference
l-Valine,
Addition to Claviceps strain Higher yields of ergo[2]
l-leucine,
producing ergornine, acornine, a-ergokryptine
l-isoleucine
and b-ergokryptine
and b-ergokryptine
respectively
l-Valine
Use of lower concentration Change of the ergo[68]
of synthon and addition at cornine/ergokryptine ratio
an optimal time (towards
2:1 to the desired ratio 1:1
the end of the bioprocess) for better pharmacologic
activity
p-Chlorophenylalanine, Use of a phenylalanine
New alkaloids with the
[2]
p-fluorophenylalanine,
auxotrophic ergocristine
synthons as amino acid II
5,5,5-trifluoroleucine,
producing and a leucine
b-hydroxyleucine
auxotrophic ergocornine
and ergokryptine producing
strain
[114 C]-Aminobutyric
Use of Claviceps purpurea
Isolation of ergobine, the
[69]
acid
strain 231 F1 (producer of missing member of the
ergocornine)
series in the ergotamine
group having a-aminobutyric acid as amino
acid II
l-Thiazolidine-4Use of ergosine, ergotamine Sulfur-containing peptide [2]
carboxylic acid
and ergocristine producing alkaloids
Claviceps strains
Norvaline
Use of Claviceps purpurea
Incorporation of norvaline [70]
strain 231 F1 (producer of in position of amino acid I
ergocornine)
led to the isolation of three
unnatural ergopeptine
alkaloids – ergorine,
ergonorine, and ergonornorine
Derivative of DMAT:
Use of washed mycelium
To probe the possibility of [71]
3-[4-((E)-3,4-dihydroxy- of Claviceps sp. SD58
diastereomeric amino acids
3-methyl-1-butenyl)-1Hbeing intermediates in ergot
indol-3-yl]-2alkaloid biosynthesis
(methylamino)propanoic
acid, trideuterated in its
methyl group
2 Derivatives of DMAT:
Use of washed mycelium of To study the mode of C
[72]
(E)-N-(methyl-d 3 )-4-(3- Claviceps sp. SD58
ring formation in ergot
methyl-1,3-butadienyl)alkaloid biosynthesis
dl-tryptophan,
hydroxy-3-methyl-1butenyl)-dl-tryptophan
11
Table 2. Application of different feeding strategies in the directed biosynthesis of Claviceps
Synthon
Incorporation strategy
Target/Objective
Reference
l-Valine,
Addition to Claviceps strain Higher yields of ergo[2]
l-leucine,
producing ergornine, acornine, a-ergokryptine
l-isoleucine
and b-ergokryptine
and b-ergokryptine
respectively
l-Valine
Use of lower concentration Change of the ergo[68]
of synthon and addition at cornine/ergokryptine ratio
an optimal time (towards
2:1 to the desired ratio 1:1
the end of the bioprocess) for better pharmacologic
activity
p-Chlorophenylalanine, Use of a phenylalanine
New alkaloids with the
[2]
p-fluorophenylalanine,
auxotrophic ergocristine
synthons as amino acid II
5,5,5-trifluoroleucine,
producing and a leucine
b-hydroxyleucine
auxotrophic ergocornine
and ergokryptine producing
strain
[114 C]-Aminobutyric
Use of Claviceps purpurea
Isolation of ergobine, the
[69]
acid
strain 231 F1 (producer of missing member of the
ergocornine)
series in the ergotamine
group having a-aminobutyric acid as amino
acid II
l-Thiazolidine-4Use of ergosine, ergotamine Sulfur-containing peptide [2]
carboxylic acid
and ergocristine producing alkaloids
Claviceps strains
Norvaline
Use of Claviceps purpurea
Incorporation of norvaline [70]
strain 231 F1 (producer of in position of amino acid I
ergocornine)
led to the isolation of three
unnatural ergopeptine
alkaloids – ergorine,
ergonorine, and ergonornorine
Derivative of DMAT:
Use of washed mycelium
To probe the possibility of [71]
3-[4-((E)-3,4-dihydroxy- of Claviceps sp. SD58
diastereomeric amino acids
3-methyl-1-butenyl)-1Hbeing intermediates in ergot
indol-3-yl]-2alkaloid biosynthesis
(methylamino)propanoic
acid, trideuterated in its
methyl group
2 Derivatives of DMAT:
Use of washed mycelium of To study the mode of C
[72]
(E)-N-(methyl-d 3 )-4-(3- Claviceps sp. SD58
ring formation in ergot
methyl-1,3-butadienyl)alkaloid biosynthesis
dl-tryptophan,
hydroxy-3-methyl-1butenyl)-dl-tryptophan