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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:67159;
ChemSpider	2299489;
KEGG	C20436;
PubChem CID	3035188;
UNII	DV9FK5AO1K ;
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]

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.

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[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.

[1]

[2]

v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Amesergide Bromerguride (2-bromolisuride) 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 Fludihydroergotamine Lisuride LY-215,840 LSH Lysergic acid Lysergic acid methyl ester Lysergine Lysergol Mergocriptine Mesulergine Metergoline Metergotamine MIPLA Methysergide Propisergide 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 (lysergide) 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	9-Deacetoxyfumigaclavine C Agroclavine Chanoclavine Chanoclavine II Costaclavin Cycloclavine Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Paliclavine Penniclavine Setoclavine
Other ergolines	Acetergamine Brazergoline Cianergoline CY-208,243 Delergotrile Disulergine Dosergoside Ergoline Etisulergine Lergotrile Nicergoline Pergolide Proterguride Romergoline Terguride Tiomergine Voxergolide
Related compounds	Adrogolide Naxagolide Quinagolide
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)

See also

References