Retrorsine

Chemical compound From Wikipedia, the free encyclopedia

Retrorsine (RTS or RS) is a naturally occurring pyrrolizidine alkaloid primarily found in plants of the genus Senecio.[2][3] It was first isolated from the plant Senecio retrorsus and named by the Canadian chemist Richard H.F. Manske in 1931.[4] Known for its potent hepatotoxicity (one of the most potent liver toxin among pyrrolizidine alkaloids) and carcinogenicity, it is a significant plant toxin affecting livestock and humans through contaminated feed and herbal products.[2][3][5][6]

Quick facts Names, Identifiers ...
Retrorsine
Names
IUPAC name
(1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
Other names
Retrorsin
β-Longilobine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.119.898 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-/t11-,14-,15-,18-/m1/s1
    Key: BCJMNZRQJAVDLD-CQRYIUNCSA-N
  • C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(CO)O)C
Properties
C18H25NO6
Molar mass 351.399 g·mol−1
Appearance Colorless prisms
Density 1.38 g/cm3
Melting point 212 °C (414 °F; 485 K)
Solubility Soluble in chloroform
Slightly soluble in acetone, ethanol, water
Hazards
GHS labelling:[1]
GHS06: Toxic
Danger
H300
P264, P270, P301+P316, P321, P330, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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In biomedical research, retrorsine is used to induce selective liver injury in animal models to study liver regeneration and liver transplantation, due to its ability to block the cell cycle of host hepatocytes without killing them immediately, such as the retrorsine/partial hepatectomy (RS/PH) model.[3][7][8][9][10]

References

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