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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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Chun-Hsien Yu et al.
Cell transplantation, 18(10), 1081-1092 (2009-08-05)
Efficient repopulation by transplanted hepatocytes in the severely injured liver is essential for their clinical application in the treatment of acute hepatic failure. We studied here whether and how the transplanted hepatocytes are able to efficiently repopulate the toxin-induced acute
Mabel Fragoso-Serrano et al.
Journal of natural products, 75(5), 890-895 (2012-05-04)
Commercial preparations of the Mexican herbal drug known as "miracle tea" (Packera candidissima and P. bellidifolia) have been profiled qualitatively by HPLC and GC-MS. Eremophilanes (3-7) were the major components found in the hexane-soluble fraction, while pyrrolizidine alkaloids (PAs) were
Biao Zhang et al.
The Journal of surgical research, 157(1), 71-80 (2009-04-07)
The therapeutic effects of bone marrow and hepatocyte transplantation were investigated regarding the treatment of retrorsine-partial hepatectomy-induced liver injury. Analbuminemic F344alb rats were given two doses of retrorsine 2 wk apart, followed 4 wk later by transplantation with F344 rat
Kate E Brilliant et al.
Transplantation, 88(4), 486-495 (2009-08-22)
Pretreatment with retrorsine crosslinks host hepatocyte DNA and prevents proliferation after partial hepatectomy (PH), allowing selective expansion of transplanted progenitors. Shortcomings are length of protocol and carcinogenicity of retrorsine. This report describes a rapid liver repopulation protocol using mitomycin C
Gary E Martin et al.
Magnetic resonance in chemistry : MRC, 50(8), 563-568 (2012-07-19)
ADEQUATE experiments provide an alternative to the more commonly employed GHMBC experiment for the establishment of long-range heteronuclear connectivities. The 1,1-ADEQUATE experiment allows the unequivocal identification of both protonated and non-protonated carbon resonances adjacent to a protonated carbon. The 1,n-ADEQUATE
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