Ferroptosis-centered Drug Response Information

General Information of the Drug (ID: ferrodrug0344)
Name
Eupalinolide B
Synonyms
Eupalinolide A; Eupalinolide B; 877822-41-8; C24H30O9; Eupalinolide-A; 877822-40-7; DTXSID50855825; HY-N0753; AC-35004; CS-0009781; (3aR,4R,6Z,9S,10E,11aR)-9-(Acetyloxy)-6-[(acetyloxy)methyl]-10-methyl-3-methylidene-2-oxo-2,3,3a,4,5,8,9,11a-octahydrocyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-methylbut-2-enoate

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Structure
Formula
C24H30O9
IUPAC Name
[(3aR,4R,6Z,9S,10E,11aR)-9-acetyloxy-6-(acetyloxymethyl)-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-methylbut-2-enoate
Canonical SMILES
CC1=CC2C(C(CC(=CCC1OC(=O)C)COC(=O)C)OC(=O)C(=CCO)C)C(=C)C(=O)O2
InChI
InChI=1S/C24H30O9/c1-13(8-9-25)23(28)32-21-11-18(12-30-16(4)26)6-7-19(31-17(5)27)14(2)10-20-22(21)15(3)24(29)33-20/h6,8,10,19-22,25H,3,7,9,11-12H2,1-2,4-5H3/b13-8+,14-10+,18-6-/t19-,20+,21+,22-/m0/s1
InChIKey
HPWMABTYJYZFLK-FHEQDPKSSA-N
PubChem CID
71463992
Full List of Ferroptosis Target Related to This Drug
Heme oxygenase 1 (HMOX1)
 Target Info 
In total 1 item(s) under this Target
Experiment 1 Reporting the Ferroptosis-centered Drug Act on This Target [1]
Target for Ferroptosis Driver
Responsed Disease Hepatocellular carcinoma ICD-11: 2C12
 Disease Info 
Pathway Response MAPK signaling pathway hsa04010
Ferroptosis hsa04216
Cell Process Cell ferroptosis
Cell migration
Cell proliferation
In Vitro Model SMMC-7721 cells Endocervical adenocarcinoma Homo sapiens CVCL_0534
HCCLM3 cells Adult hepatocellular carcinoma Homo sapiens CVCL_6832
In Vivo Model
Four-week-old nude mice (BALB/c) were used, and they were housed for 1 week in a specific pathogen-free (SPF) environment before experimentation. Each mouse received subcutaneous injections of 1 x 106 SMMC-7721 or HCCLM3 cells in 200 uL phosphate-buffered saline (PBS) into both flanks. One group was intraperitoneally injected every two days with EB at 25 or 50 mg/mouse body weight, for a total of 3 weeks. As a control, DMSO was used in another group. Tumor size was measured to calculate tumor volume, and mouse body weights were monitored every two days.

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Response regulation Eupalinolide B (EB) exerts anti-proliferative activity in hepatic carcinoma by blocking cell cycle arrest at S phase and inducing ferroptosis mediated by endoplasmic reticulum (ER) stress, as well as HO-1 activation. And EB has the ability to inhibit cell proliferation and migration in hepatic carcinoma.
References
Ref 1 Eupalinolide B inhibits hepatic carcinoma by inducing ferroptosis and ROS-ER-JNK pathway. Acta Biochim Biophys Sin (Shanghai). 2022 Jul 25;54(7):974-986. doi: 10.3724/abbs.2022082.