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

Chemical compound

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]

References

^ 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.
^ 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.

Ergolines

Lysergic acid
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

Psychedelic
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

Clavines

Other
ergolines

Natural
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)