Senecionine

Senecionine
Names
	Other names Aureine
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9107 ;
ChEMBL	ChEMBL362153 ;
ChemSpider	10254883 ;
ECHA InfoCard	100.125.118
KEGG	C06176 ;
PubChem CID	5280906;
CompTox Dashboard (EPA)	DTXSID40871615 ;
	InChI InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-/t11-,14-,15-,18-/m1/s1 Key: HKODIGSRFALUTA-JTLQZVBZSA-N ;
	SMILES O=C1O[C@@H]3CCN2C\C=C(\COC(=O)[C@](C)(O)[C@H](C)CC1=[C@H]C)[C@@H]23;
Properties
Chemical formula	C18H25NO5
Density	1.25 g/cm3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Senecionine is an organic compound with the chemical formula C
₁₈H
₂₅NO
₅. It is produced by Senecio species and classified as a pyrrolizidine alkaloid. It has a core structure of retronecine which is further esterified by two Isoleucine to form a 12 member lactone ring. The compound is toxic and as alkaloid of the widespread plant Jacobaea vulgaris also problematic for feed stock and human consumption.^[1]

Biosynthesis

In Senecio species, biosynthesis of Senecionine starts from L-Arginine or L-ornithine. Since plants don't have decarboxylase enzyme for L-ornithine, it must be first converted into L-Arginine, which can be readily converted to putrescine. Putrescine gains an aminopropyl group from spermidine in an NAD+ fashion to form homospermidine via homospermidine synthase. The detailed mechanism for this step isn't well understood and it is suspected that imine intermediate is involved. Homospermidine undergo a series of reactions to form the 2 five member rings structure of retronecine. Retronecine is further esterified by two L-isoleucine and modified through a couple of steps to senecionine.

References

^ "Pyrrolizidine Alkaloids—Genotoxicity, Metabolism Enzymes, Metabolic Activation, and Mechanisms". doi:10.1081/DMR-120028426. {{cite journal}}: Cite journal requires |journal= (help)

Dewick, M,Paul (Feb 4, 2009). Medicinal Natural Products. wiley online. pp. 324–325. doi:10.1002/9780470742761. ISBN 9780470742761.{{cite book}}: CS1 maint: multiple names: authors list (link)

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[1] "Pyrrolizidine Alkaloids—Genotoxicity, Metabolism Enzymes, Metabolic Activation, and Mechanisms". doi:10.1081/DMR-120028426. {{cite journal}}: Cite journal requires |journal= (help)

[1]

Biosynthesis

See also

References