Retrorsine
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
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.119.898
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
C 18 H 25 N O 6
Molar mass g·mol−1
Appearance
Colorless prisms
Density 1.38 g/cm3
Melting point 212 °C (414 °F; 485 K)
Solubility Soluble in chloroform acetone , ethanol , water
Hazards
GHS labelling[ 1]
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).
Chemical compound
Retrorsine (RTS or RS ) is a naturally occurring pyrrolizidine alkaloid primarily found in plants of the genus Senecio [ 2] [ 3] Senecio retrorsus Canadian chemist Richard Manske in 1931.[ 4] 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]
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
↑ "Retrorsine" . PubChem . Retrieved 2026-02-13 .1 2 Guo, Li; Zhang, Li; Xu, Haiman; Yu, Pei; Wang, Zhigang; Lu, Danyi; Chen, Min; Wu, Baojian (2021-09-02). "Diurnal hepatic CYP3A11 contributes to chronotoxicity of the pyrrolizidine alkaloid retrorsine in mice". Xenobiotica . 51 (9): 1019– 1028. doi :10.1080/00498254.2021.1950867 . ISSN 0049-8254 . PMID 34311664 . 1 2 3 Zhu, Yanli; Zhang, Shuhang; Shao, Yin; Tang, Lihui; Zhang, Congcheng; Tang, Shiyu; Lu, Hao (2024). "Regulatory role of oxidative stress in retrorsine – Induced apoptosis and autophagy in primary rat hepatocytes" . Ecotoxicology and Environmental Safety . 279 116515. Bibcode :2024EcoES.27916515Z . doi :10.1016/j.ecoenv.2024.116515 PMID 38810283 . ↑ Manske, Richard H. F. (1931-12-01). "THE ALKALOIDS OF SENECIO SPECIES: I. THE NECINES AND NECIC ACIDS FROM S . RETRORSUS AND S . JACOBAEA ". Canadian Journal of Research . 5 (6): 651– 659. Bibcode :1931CJRes...5..651M . doi :10.1139/cjr31-103 . ISSN 1923-4287 . ↑ Schoental, Regina (1959). "Liver lesions in young rats suckled by mothers treated with the pyrrolizidine (Senecio) alkaloids, lasiocarpine and retrorsine". The Journal of Pathology and Bacteriology . 77 (2): 485– 495. doi :10.1002/path.1700770220 . ISSN 0368-3494 . PMID 13642195 . ↑ Mulder, Patrick P.J.; López, Patricia; Castelari, Massimo; Bodi, Dorina; Ronczka, Stefan; Preiss-Weigert, Angelika; These, Anja (2018-01-02). "Occurrence of pyrrolizidine alkaloids in animal- and plant-derived food: results of a survey across Europe". Food Additives & Contaminants: Part A . 35 (1): 118– 133. doi :10.1080/19440049.2017.1382726 . ISSN 1944-0049 . PMID 28942718 . ↑ Laconi, Ezio; Oren, Ran; Mukhopadhyay, Deb K.; Hurston, Ethel; Laconi, Sergio; Pani, Paolo; Dabeva, Mariana D.; Shafritz, David A. (1998). "Long-Term, Near-Total Liver Replacement by Transplantation of Isolated Hepatocytes in Rats Treated with Retrorsine" . The American Journal of Pathology . 153 (1): 319– 329. doi :10.1016/S0002-9440(10)65574-5 . PMC 1852941 PMID 9665494 . ↑ Shafritz, David A.; Oertel, Michael (2011). "Model systems and experimental conditions that lead to effective repopulation of the liver by transplanted cells" . The International Journal of Biochemistry & Cell Biology . 43 (2): 198– 213. doi :10.1016/j.biocel.2010.01.013 . PMC 2907475 PMID 20080205 . ↑ Laconi, Sergio; Doratiotto, Silvia; Montisci, Stefania; Pani, Paolo; Laconi, Ezio (2008). "Repopulation by Endogenous Hepatocytes Does Not Reconstitute Liver Mass in Rats Treated with Retrorsine". Cell Transplantation . 17 (12): 1415– 1421. doi :10.3727/096368908787648128 . ISSN 0963-6897 . PMID 19364078 . ↑ Tsuchida, Tomonori; Murata, Soichiro; Matsuki, Koichiro; Mori, Akihiro; Matsuo, Megumi; Mikami, Satoshi; Okamoto, Satoshi; Ueno, Yasuharu; Tadokoro, Tomomi; Zheng, Yun-Wen; Taniguchi, Hideki (2019-12-26). "The Regenerative Effect of Portal Vein Injection of Liver Organoids by Retrorsine/Partial Hepatectomy in Rats" . International Journal of Molecular Sciences . 21 (1): 178. doi :10.3390/ijms21010178 ISSN 1422-0067 . PMC 6981799 PMID 31887985 .
