Retrorsine

Last updated
Retrorsine
Retrorsine.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
AppearanceColorless prisms
Density 1.38 g/cm3
Melting point 212 °C (414 °F; 485 K)
Solubility Soluble in chloroform; slightly soluble in acetone, ethanol, water
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 . [1] [2] It was first isolated from the plant Senecio retrorsus (now classified under Senecio latifolius ) and named by the Canadian chemist Richard H.F. Manske in 1931. [3] 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. [1] [2] [4] [5]

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. [2] [6] [7] [8] [9]

References

  1. 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.
  2. 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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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