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)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C23H30N2O2/c1-7-23(4,5)22-16-11-18-20(15-9-8-10-17(24-22)19(15)16)21(27-14(3)26)13(2)12-25(18)6/h7-10,13,18,20-21,24H,1,11-12H2,2-6H3/t13-,18+,20?,21-/m0/s1
    Key: OSICWVVWEXKSBD-HXLPLIFYSA-N
  • 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
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).

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

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

See also

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. PMID 21186384.


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