89353-99-1
Chemical Structure
Chiisanogenin
- CAS No.: 89353-99-1
- Formula:C30H44O5
- Molecular Weight:484.68
IUPAC Name: (3S,3aS,3a1S,4R,7aR,8aR,8bR,9R,11aS,13aR,13bR)-4-hydroxy-3a,13a,13b-trimethyl-6-oxo-3,9-di(prop-1-en-2-yl)octadecahydrocyclopenta[7,8]phenanthro[10,1-bc]oxepine-11a(1H)-carboxylic acid
InChIKey: BYCBJBLIOKGBPB-YQIBJACNSA-N
SMILES: C[C@]12[C@]3([C@](C)([C@H](C(C)=C)CC1)[C@H](O)CC(=O)O[C@@]3(C[C@]4([C@@]2(C)CC[C@]5(C(O)=O)[C@@]4([C@H](C(C)=C)CC5)[H])[H])[H])[H]
Biological Activity: Chiisanogenin is an orally active triterpenoid. Chiisanogenin reduces postprandial blood glucose by promoting GLUT4 translocation and glucose uptake via activation of the IRS-1/PI3K/Akt signaling pathway. Chiisanogenin binds to MLKL and inhibits its phosphorylation and oligomerization, maintains lysosomal integrity, restores autophagic flux, and suppresses NLRP3 inflammasome activation and pyroptosis. Chiisanogenin inhibits xanthine oxidase activity and regulates oxidative stress and ion pump activity. Chiisanogenin binds to or inhibits PKA, H+/K+-ATPase and β-glucuronidase. Chiisanogenin possesses multiple pharmacological activities, including broad-spectrum antibacterial activity, anticancer, anti-inflammatory, antirheumatic, renoprotective, cardioprotective and antiarrhythmic effects. Chiisanogenin can be used in research related to type 2 diabetes, rheumatoid arthritis, myocardial injury, hepatocellular carcinoma and ventricular arrhythmia[1][2][3][4][5][6][7][8][9][10].
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Chiisanogenin | Chiisanogenin is an orally active triterpenoid. Chiisanogenin reduces postprandial blood glucose by promoting GLUT4 translocation and glucose uptake via activation of the IRS-1/PI3K/Akt signaling pathway. Chiisanogenin binds to MLKL and inhibits its phosphorylation and oligomerization, maintains lysosomal integrity, restores autophagic flux, and suppresses NLRP3 inflammasome activation and pyroptosis. Chiisanogenin inhibits xanthine oxidase activity and regulates oxidative stress and ion pump activity. Chiisanogenin binds to or inhibits PKA, H+/K+-ATPase and β-glucuronidase. Chiisanogenin possesses multiple pharmacological activities, including broad-spectrum antibacterial activity, anticancer, anti-inflammatory, antirheumatic, renoprotective, cardioprotective and antiarrhythmic effects. Chiisanogenin can be used in research related to type 2 diabetes, rheumatoid arthritis, myocardial injury, hepatocellular carcinoma and ventricular arrhythmia. | |||||||||||||||||||||
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- [1]. Kwon EB, et al. Chiisanogenin enhances glucose uptake and lowers blood glucose via insulin signaling activation. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2025 Aug;189:118281. [Content Brief]
- [2]. Jung HJ, et al. Antiinflammatory effects of chiisanoside and chiisanogenin obtained from the leaves of Acanthopanax chiisanensis in the carrageenan- and Freund's complete adjuvant-induced rats. Journal of ethnopharmacology. 2005 Feb 28;97(2):359-67. [Content Brief]
- [3]. Qu S, et al. Chiisanogenin Targets MLKL to Restore Autophagy and Suppress Pyroptosis in Renal Ischemia-Reperfusion Injury. Journal of agricultural and food chemistry. 2026 Jun 10;74(22):17099-17128. [Content Brief]
- [4]. Bae EA, et al. Metabolism of chiisanoside from Acanthopanax divaricatus var. albeofructus by human intestinal bacteria and its relation to some biological activities. Biological & pharmaceutical bulletin. 2001 May;24(5):582-5. [Content Brief]
- [5]. Lee S, et al. Antibacterial compounds from the leaves of Acanthopanax senticosus. Archives of pharmacal research. 2003 Jan;26(1):40-2. [Content Brief]
- [6]. Yang C, et al. Determination and pharmacokinetic study of chiisanogenin in rat plasma by ultra performance liquid chromatography-tandem mass spectrometry. Phytochemical analysis : PCA. 2011;22(3):225-9. [Content Brief]
- [7]. Wang H, et al. Potential Myocardial Protection of 3,4-seco-Lupane Triterpenoids from Acanthopanax sessiliflorus Leaves. Chemistry & biodiversity. 2021 Jan;18(1):e2000830. [Content Brief]
- [8]. Wang H, et al. Cytotoxic and anti-tumor effects of 3,4-seco-lupane triterpenoids from the leaves of Eleutherococcus sessiliflorus against hepatocellular carcinoma. Nat Prod Res. 2022 Feb;36(4):1062-1066. [Content Brief]
- [9]. Liu Y, et al. Triterpenoids from the leaves of Eleutherococcus sessiliflorus, and their antiproliferative activities in TNF-α induced HFLS-RA cells. Phytochemistry. 2024 Jul;223:114133. [Content Brief]
- [10]. Zhao Y, et al. Protective Effects of 3,4-Seco-Lupane Triterpenes from Food Raw Materials of the Leaves of Eleutherococcus Senticosus and Eleutherococcus Sessiliflorus on Arrhythmia Induced by Barium Chloride. Chemistry & biodiversity. 2021 Apr;18(4):e2001021. [Content Brief]
Keywords
