Fumigaclavine A

Fumigaclavine A

Names
IUPAC name [(6aR,9R,10S)-7,9-Dimethyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-10-yl] acetate
Other names (8α,9β)-6,8-Dimethylergolin-9-ol acetate
Identifiers
CAS Number	6879-59-0  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:67159
ChemSpider	2299489
KEGG	C20436
PubChem CID	3035188
UNII	DV9FK5AO1K  Y
CompTox Dashboard (EPA)	DTXSID40988499
InChI InChI=1S/C18H22N2O2/c1-10-9-20(3)15-7-12-8-19-14-6-4-5-13(16(12)14)17(15)18(10)22-11(2)21/h4-6,8,10,15,17-19H,7,9H2,1-3H3/t10-,15-,17-,18+/m1/s1 Key: GJSSYQDXZLZOLR-ONUGHKICSA-N
SMILES C[C@@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2[C@H]1OC(=O)C)C
Properties
Chemical formula	C18H22N2O2
Molar mass	298.386 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

Fumigaclavine A is an antibacterial ergoline alkaloid produced by endophytic Aspergillus . ^[1]

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

See also

• Fumigaclavine B
• Fumigaclavine C
• Fumigaclavine A dimethylallyltransferase

References

1. Pinheiro, EA; Carvalho, JM; Dos Santos, DC; Feitosa, AD; Marinho, PS; Guilhon, GM; De Souza, AD; Da Silva, FM; Marinho, AM (2012). "Antibacterial activity of alkaloids produced by endophytic fungus Aspergillus sp. EJC08 isolated from medical plant Bauhinia guianensis". Natural Product Research. 27 (18): 1633–8. doi:10.1080/14786419.2012.750316. PMID   23234304. S2CID   38933742.
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.