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R0382

Sigma-Aldrich

Retrorsine

≥90% (HPLC), powder, retronecine-type pyrrolizidine alkaloid

Synonym(s):

Retrorsin, Senecionan-11,16-Dione, 12,18-Dihydroxy- (9CI), β-Longilobine, 12,18-Dihydroxysenecionan-11,16-dione

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About This Item

Empirical Formula (Hill Notation):
C18H25NO6
CAS Number:
480-54-6
Molecular Weight:
351.39
UNSPSC Code:
12352200
PubChem Substance ID:
24899338
NACRES:
NA.77

product name

Retrorsine, ≥90% (HPLC)

Assay

≥90% (HPLC)

mp

208-211 °C (lit.)

SMILES string

C\C=C1\C[C@@H](C)[C@](O)(CO)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23

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

InChI key

BCJMNZRQJAVDLD-CQRYIUNCSA-N

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Application

Retrorsine has been used:
  • as a mito-inhibitory pyrrolizidine alkaloid compound to induce necrotic liver injury in rats
  • to induce hepatocellular injury in rats
  • to arrest endogenous hepatocyte growth in mice

Biochem/physiol Actions

Retrorsine (RTS) is a retronecine-type pyrrolizidine alkaloid associated with Senecio and Crotalaria species. It belongs to the pyrrolizidine alkaloid family with mito-inhibitory property and elicits hepatotoxicity. It mediates the inactivation of cytochrome P450 3A4. Retrorsine also inhibits replication of fully differentiated hepatocytes.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Valerie Gouon-Evans et al.
Nature biotechnology, 24(11), 1402-1411 (2006-11-07)
When differentiated in the presence of activin A in serum-free conditions, mouse embryonic stem cells efficiently generate an endoderm progenitor population defined by the coexpression of either Brachyury, Foxa2 and c-Kit, or c-Kit and Cxcr4. Specification of these progenitors with
Qingsu Xia et al.
Toxicology letters, 178(2), 77-82 (2008-04-09)
Pyrrolizidine alkaloid-containing plants are widespread in the world and may be the most common poisonous plants affecting livestock, wildlife, and humans. Pyrrolizidine alkaloids require metabolism to exert their genotoxicity and tumorigenicity. Our mechanistic studies have determined that metabolism of the
Ya-Hui Chen et al.
Hepatology (Baltimore, Md.), 57(3), 1215-1224 (2012-10-20)
The potential lineage relationship between hepatic oval cells, small hepatocyte-like progenitor cells (SHPCs), and hepatocytes in liver regeneration is debated. To test whether mature hepatocytes can give rise to SHPCs, rats with dipeptidyl peptidase IV (DPPIV) chimeric livers, which harbored
Chun-Hsien Yu et al.
Cell transplantation, 19(2), 231-243 (2009-11-13)
Oval cells and hepatocytes rarely proliferate simultaneously. This study aimed to determine the impacts of hepatocyte transplantation on the response and fate of oval cells that are activated to proliferate in acute severe hepatic injury. Retrorsine + D-galactosamine (R+D-gal) treatment
Gary E Martin et al.
Journal of natural products, 74(11), 2400-2407 (2011-11-08)
1H-13C GHSQC and GHMBC spectra are irrefutably among the most valuable 2D NMR experiments for the establishment of unknown chemical structures. However, the indeterminate nature of the length of the long-range coupling(s) observed via the (n)J(CH)-optimized delay of the GHMBC
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