R0382
倒千里光碱
≥90% (HPLC), powder, retronecine-type pyrrolizidine alkaloid
别名:
Retrorsin, Senecionan-11,16-Dione, 12,18-Dihydroxy- (9CI), β-Longilobine, 12,18-Dihydroxysenecionan-11,16-dione
产品名称
倒千里光碱, ≥90% (HPLC)
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
assay
≥90% (HPLC)
mp
208-211 °C (lit.)
Quality Level
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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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral
存储类别
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
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
法规信息
涉药品监管产品
此项目有
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
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
Virginie Pichard et al.
PloS one, 4(9), e7267-e7267 (2009-10-01)
When hepatocyte proliferation is impaired, liver regeneration proceeds from the division of non parenchymal hepatocyte progenitors. Oval cells and Small Hepatocyte-like Progenitor Cells (SHPCs) represent the two most studied examples of such epithelial cells with putative stem cell capacity. In
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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