| Identification | Back Directory | [Name]
RETRORSINE | [CAS]
480-54-6 | [Synonyms]
RETRORSIN
Retrosine
Retrorcine
RETRORSINE
β-Longilobine
RETRORSINE(AS)
BETA-LONGILOBINE
cis-retronecicacidesterofretronecine
12,18-DIHYDROXYSENECIONAN-11,16-DIONE
16-dione,12,18-dihydroxy-senecionan-1
β-Longilobine, 12,18-Dihydroxysenecionan-11,16-dione
methyl(1,6)dioxacyclododeca(2,3,4-gh)pyrrolizidine-2,7-dione
5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-hydroxymethyl-5-3-ethylidene-4
trans-15-ethylidene-12beta-hydroxy-12alpha-hydroxymethyl-13beta-methylsenec-1-
[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, (3Z,5R,6S,14aR,14bR)- | [EINECS(EC#)]
999-999-2 | [Molecular Formula]
C18H25NO6 | [MDL Number]
MFCD00013331 | [MOL File]
480-54-6.mol | [Molecular Weight]
351.39 |
| Chemical Properties | Back Directory | [Melting point ]
208-211 °C(lit.) | [alpha ]
D18 -17.6° (c = 1.99 in ethanol) | [Boiling point ]
485.2°C (rough estimate) | [density ]
1.32±0.1 g/cm3 (20 ºC 760 Torr) | [refractive index ]
1.5100 (estimate) | [storage temp. ]
?20°C | [solubility ]
DMSO: Slightly soluble: 0.1-1 mg/mlPBS (pH 7.2): Slightly soluble: 0.1-1 mg/ml | [form ]
neat | [pka]
12.00±0.40(Predicted) | [color ]
White to off-white | [Merck ]
13,8253 | [InChI]
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 | [InChIKey]
BCJMNZRQJAVDLD-VMOBWIEOSA-N | [SMILES]
N12CC=C3COC(=O)[C@@](O)(CO)[C@H](C)C/C(=C/C)/C(=O)O[C@@]([H])([C@]13[H])CC2 | [CAS DataBase Reference]
480-54-6 | [IARC]
3 (Vol. 10, Sup 7) 1987 | [EPA Substance Registry System]
Retrorsine (480-54-6) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
25 | [Safety Statements ]
22-36/37/39-45 | [RIDADR ]
1544 | [WGK Germany ]
3 | [RTECS ]
VH7525000 | [HazardClass ]
6.1(a) | [PackingGroup ]
II | [Safety Profile]
Poison by ingestion, intraperitoneal, and intravenous routes. Questionable carcinogen with experimental neoplastigenic and tumorigenic data. hhtation data reported. When heated to decomposition it emits toxic fumes of NOx. | [Hazardous Substances Data]
480-54-6(Hazardous Substances Data) |
| Hazard Information | Back Directory | [Uses]
Retrorsine-D4 is a labelled analogue of Retrorsine (R279000). Retrorsine is a pyrrolizidine alkaloid that blocks the hepatocyte cell cycle, ultimately affecting hepatocyte proliferative capacity. | [Definition]
ChEBI: Retrorsine is a macrolide. | [General Description]
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG | [in vivo]
Retrorsine (30 mg/kg; i.p.; twice) impairs liver regeneration in the PBL model not only by an S or G2/M phase block, but also by a block located before the G1/S transition of the cell cycle[4].
| Animal Model: | Male Wistar rats (180±20 g), portal branch ligation (PBL) model[4] | | Dosage: | 30 mg/kg | | Administration: | Intraperitoneal injection, twice, separated by 2-week interval | | Result: | Strongly impaired the liver weight gain, protein and DNA synthesis as well as induction of cell cycle related proteins in the regenerating lobes after PBL. |
| [References]
[1] C.C.J. CULVENOR. Hepato- and pneumotoxicity of pyrrolizidine alkaloids and derivatives in relation to molecular structure[J]. Chemico-Biological Interactions, 1976, 12 3: Pages 299-324. DOI: 10.1016/0009-2797(76)90046-6
[2] M. J. PESTCHANKER O. S G. Pyrrolizidine Alkaloids from Five Senecio Species[J]. Journal of Natural Products , 1986, 49 4: 722-723. DOI: 10.1021/np50046a041
[3] YAN HONG LI. Assessment of pyrrolizidine alkaloid-induced toxicity in an in vitro screening model[J]. Journal of ethnopharmacology, 2013, 150 2: Pages 560-567. DOI: 10.1016/j.jep.2013.09.010 |
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