Names | |
---|---|
IUPAC name
(6-Methyl-8,9-didehydroergolin-8-yl)methanol
| |
Systematic IUPAC name
[(6aR,10aR)-7-Methyl-4,6,6a,7,8,10a-hexahydroindolo[4,3-fg]quinolin-9-yl]methanol | |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.008.136 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C16H18N2O | |
Molar mass | 254.327 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Elymoclavine is an ergot alkaloid (ergoline alkaloid). It can be produced from C. fusiformis from Pennisetum typhoideum. It is a precursor in the biosynthesis of D-(+)-lysergic acid. Ergot alkaloids are natural products derived from L-tryptophan. They are often toxic for humans and animals. Despite that they are also well known for their pharmacological activities. [1] [2]
The main building blocks for biosynthesis of elymoclavine are tryptophan (Trp) and DMAPP. DMATrp is obtained after electrophilic substitution followed by addition (Step A below). Then an amine is methylated by an N-methyltransfersase (Step B). Next, the allyl alcohol is oxidized to the diene (Step C). After 1,4-elimination, the diene undergoes an epoxidation (Step D). Then decarboxylation is followed by the 6-member ring formation and epoxide opened to form terminal alcohol (Step E). Obtained chanoclavine gets oxidized to chanoclavine aldehyde (Step F). Then the second 6-member ring forms and agroclavine is obtained after additional reductase (Steps G and H). Finally elymoclavine is generated after an oxidation (Step I). The last step is NADPH-dependent, and it is suggested that cytochrome P450 is the catalyst. [3] [4]
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Names | |
---|---|
IUPAC name
(6-Methyl-8,9-didehydroergolin-8-yl)methanol
| |
Systematic IUPAC name
[(6aR,10aR)-7-Methyl-4,6,6a,7,8,10a-hexahydroindolo[4,3-fg]quinolin-9-yl]methanol | |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.008.136 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C16H18N2O | |
Molar mass | 254.327 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Elymoclavine is an ergot alkaloid (ergoline alkaloid). It can be produced from C. fusiformis from Pennisetum typhoideum. It is a precursor in the biosynthesis of D-(+)-lysergic acid. Ergot alkaloids are natural products derived from L-tryptophan. They are often toxic for humans and animals. Despite that they are also well known for their pharmacological activities. [1] [2]
The main building blocks for biosynthesis of elymoclavine are tryptophan (Trp) and DMAPP. DMATrp is obtained after electrophilic substitution followed by addition (Step A below). Then an amine is methylated by an N-methyltransfersase (Step B). Next, the allyl alcohol is oxidized to the diene (Step C). After 1,4-elimination, the diene undergoes an epoxidation (Step D). Then decarboxylation is followed by the 6-member ring formation and epoxide opened to form terminal alcohol (Step E). Obtained chanoclavine gets oxidized to chanoclavine aldehyde (Step F). Then the second 6-member ring forms and agroclavine is obtained after additional reductase (Steps G and H). Finally elymoclavine is generated after an oxidation (Step I). The last step is NADPH-dependent, and it is suggested that cytochrome P450 is the catalyst. [3] [4]
{{
cite journal}}
: Cite journal requires |journal=
(
help)