Elymoclavine

Elymoclavine

Names
IUPAC name (6-Methyl-8,9-didehydroergolin-8-yl)methanol
Identifiers
CAS Number	548-43-6
ChemSpider	389734
Jmol interactive 3D	Image
PubChem	440904
InChI InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,13,15,17,19H,6,8-9H2,1H3/t13-,15-/m1/s1 Key: DAVNRFCJMIONPO-UKRRQHHQSA-N InChI=1/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,13,15,17,19H,6,8-9H2,1H3/t13-,15-/m1/s1 Key: DAVNRFCJMIONPO-UKRRQHHQBW
SMILES OCC\2=C\[C@@H]3c4cccc1c4c(cn1)C[C@H]3N(C/2)C
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

1. 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.
2. Komarova, E. L.; Tolkachev O. N. (2001). Pharm. Chem. J. 35 (10): 542–549. doi:10.1023/A:1014706301632. Missing or empty |title= (help)
3. Schardl, C. L.; Panaccione D. G.; Tudzynski P. "The Alkaloids - Chemistry and Biology".
4. Dewick, P. M. (2009). Medicinal Natural Products. A Biosynthetic Approach. 3rd Edition. Wiley.