Fumigaclavine C

Fumigaclavine C is an ergoline alkaloid produced by Aspergillus fumigatus.[1]

Fumigaclavine C

Names
IUPAC name [(6aR,9S,10S)-7,9-Dimethyl-5-(2-methylbut-3-en-2-yl)-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-10-yl] acetate
Other names SM-1; (8β,9β)-2-(1,1-Dimethyl-2-propenyl)-6,8-dimethylergolin-9-ol acetate
Identifiers
3D model (JSmol)	Interactive image
PubChem CID	173878
CompTox Dashboard (EPA)	DTXSID60978599
SMILES C[C@H]1CN([C@@H]2CC3=C(NC4=CC=CC(=C34)C2[C@H]1OC(=O)C)C(C)(C)C=C)C
Properties
Chemical formula	C23H30N2O2
Molar mass	366.505 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Both 8α and 8β diastereomers (epimers) were named fumigaclavine C in scientific literature.[2]

See also

• 9-Deacetoxyfumigaclavine C
• Fumigaclavine A
• Fumigaclavine B
• Fumigaclavine A dimethylallyltransferase
• Desformylflustrabromine

References

1. Ma, HY; Song, YC; Mao, YY; Jiang, JH; Tan, RX; Luo, L (2006). "Endophytic fungal metabolite fumigaclavine C causes relaxation of isolated rat aortic rings". Planta Medica. 72 (5): 387–92. doi:10.1055/s-2005-916235. PMID 16557450.
2. Wallwey, Christiane; Li, Shu-Ming (2011-03-01). "Ergot alkaloids: structure diversity, biosynthetic gene clusters and functional proof of biosynthetic genes". Natural Product Reports. 28 (3): 496–510. doi:10.1039/C0NP00060D. ISSN 1460-4752.