Elymoclavine
Names | |
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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 | |
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3D model (JSmol) |
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ChemSpider |
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ECHA InfoCard | 100.008.136 |
PubChem CID |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | 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). Infobox references |
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]
Biosynthesis
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]
References
- ^ Ahimsa-Müller, M. A.; Markert A.; Hellwig S.; Knoop V.; Steiner U.; Drewke C.; Leistner E. (2007). "Clavicipitaceous fungi associated with ergoline alkaloid-containing convolvulaceae". J. Nat. Prod. 70 (12): 1955–1960. doi:10.1021/np070315t. PMID 18031017.
- ^ Komarova, E. L.; Tolkachev O. N. (2001). "The Chemistry of Peptide Ergot Alkaloids. Part 2. Analytical Methods for Determining Ergot Alkaloids". Pharm. Chem. J. 35 (10): 542–549. doi:10.1023/A:1014706301632. S2CID 2721387.
- ^ Schardl, C. L.; Panaccione D. G.; Tudzynski P. "The Alkaloids - Chemistry and Biology".
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(help) - ^ Dewick, P. M. (2009). Medicinal Natural Products. A Biosynthetic Approach. 3rd Edition. Wiley.
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derivatives
- 2-Bromo-LSD (BOL-148)
- Amesergide
- Bromocriptine
- Cabergoline
- Dihydroergocornine
- Dihydroergocristine
- Dihydroergocryptine
- Dihydroergometrine (Dihydroergonovine, Dihydroergobasine)
- Dihydroergosine
- Dihydroergotamine
- Epicriptine
- Ergine (LSA; LA-111; Lysergamide)
- Ergocornine
- Ergocristine
- Ergocryptine
- Ergoloid (Dihydroergotoxine)
- Ergometrine (Ergonovine, Ergobasine)
- Ergometrinine
- Ergostine
- Ergotamine
- Ergotoxine
- Ergovaline
- Lisuride
- LY-215,840
- LSH
- Lysergic acid
- Lysergic acid methyl ester
- Lysergol
- Mesulergine
- Metergoline
- MIPLA
- Methysergide
- Sergolexole
lysergamides
- 1B-LSD
- 1cP-LSD
- 1P-ETH-LAD
- 1P-LSD
- AL-LAD
- ALD-52
- BU-LAD
- CYP-LAD
- Diallyllysergamide (DAL)
- Dimethyllysergamide (DAM-57)
- ECPLA
- Ergonovine
- ETFELA
- ETH-LAD
- IP-LAD
- LAMPA
- LAE-32
- LSD
- LPD-824
- LSM-775
- LSH
- LSD-Pip
- Lysergic Acid 2-Butylamide
- Lysergic Acid 2,4-Dimethylazetidide
- Lysergic Acid 3-Pentylamide
- Lysergic acid cyclobutylamide
- Lysergic acid cyclopentylamide
- Methylergometrine (Methylergonovine, Methylergobasine)
- MIPLA
- MLD-41
- PARGY-LAD
- PRO-LAD
ergolines
sources
- Achnatherum robustum (Sleepy Grass)
- Claviceps spp. (Ergot)
Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)