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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
β-Longilobine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.119.898 Edit this at Wikidata
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
C18H25NO6
Molar mass 351.399 g·mol−1
Appearance Colorless prisms
Density 1.38 g/cm3
Melting point 212 °C (414 °F; 485 K)
Solubility Soluble in chloroform
Slightly soluble in acetone, ethanol, water
Hazards
GHS labelling:[1]
GHS06: Toxic
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).

Retrorsine (RTS or RS) is a naturally occurring pyrrolizidine alkaloid primarily found in plants of the genus Senecio.[2][3] It was first isolated from the plant Senecio retrorsus and named by the Canadian chemist Richard Manske in 1931.[4] Known for its potent 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

  1. ^ "Retrorsine". PubChem. Retrieved 2026-02-13.
  2. ^ a b 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.
  3. ^ a b c 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.

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