21871-10-3
Chemical Structure
Vernodalin
- CAS No.: 21871-10-3
- Formula:C19H20O7
- Molecular Weight:360.36
IUPAC Name: (3aR,4S,5aR,9aR,9bR)-3,9-dimethylene-2,8-dioxo-5a-vinyldecahydro-2H-furo[2,3-f]isochromen-4-yl 2-(hydroxymethyl)acrylate
InChIKey: ZSXNBLOPYIJLQV-WSVVRNJXSA-N
SMILES: C(=C)[C@@]12[C@@]([C@@]3([C@@]([C@@H](OC(C(CO)=C)=O)C1)(C(=C)C(=O)O3)[H])[H])(C(=C)C(=O)OC2)[H]
Biological Activity: Vernodalin is an orally active, cytotoxic sesquiterpene lactone with a Kd value of 9.55 μM for p38 MAPK. Vernodalin downregulates the expression of phosphorylated ERK, JNK, AKT, PI3K, mTOR, p38MAPK, FAK, MMP-2, MMP-9, and uPA, while upregulates the expression of TIMP-1 and TIMP-2. Vernodalin increases ROS production, upregulates the expression of Bax and caspase 3, downregulates the expression of Bcl-2, and induces apoptosis (apoptosis), oxidative stress response and cell cycle arrest. Vernodalin inhibits the proliferation, adhesion and metastasis of cancer cells. Vernodalin enhances the activity of VEGF-B, AMPK and eNOS signaling pathways. Vernodalin alleviates myocardial injury and restores hemodynamic parameters. Vernodalin inhibits the growth of Trypanosoma brucei rhodesiense. Vernodalin can be used in research related to various cancers including gastric cancer, colorectal cancer and lung cancer, as well as African human trypanosomiasis and myocardial infarction[1][2][3][4][5][6].
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Vernodalin | Vernodalin is an orally active, cytotoxic sesquiterpene lactone with a Kd value of 9.55 μM for p38 MAPK. Vernodalin downregulates the expression of phosphorylated ERK, JNK, AKT, PI3K, mTOR, p38MAPK, FAK, MMP-2, MMP-9, and uPA, while upregulates the expression of TIMP-1 and TIMP-2. Vernodalin increases ROS production, upregulates the expression of Bax and caspase 3, downregulates the expression of Bcl-2, and induces apoptosis (apoptosis), oxidative stress response and cell cycle arrest. Vernodalin inhibits the proliferation, adhesion and metastasis of cancer cells. Vernodalin enhances the activity of VEGF-B, AMPK and eNOS signaling pathways. Vernodalin alleviates myocardial injury and restores hemodynamic parameters. Vernodalin inhibits the growth of Trypanosoma brucei rhodesiense. Vernodalin can be used in research related to various cancers including gastric cancer, colorectal cancer and lung cancer, as well as African human trypanosomiasis and myocardial infarction. | |||||||||||||||||||||
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- [1]. Luo Y, et al. Vernodalin Suppresses Tumor Proliferation and Increases Apoptosis of Gastric Cancer Cells Through Attenuation of FAK/PI3K/AKT/mTOR and MAPKs Signaling Pathways. Current pharmaceutical biotechnology. 2023;24(5):708-717. [Content Brief]
- [2]. Tao T, et al. Vernodalin Alleviates Cardiotoxicity and Inflammation in Isoproterenol-Mediated Myocardial Infarction through NF-κB/AMPK Signaling Pathways in Rats. Comb Chem High Throughput Screen. 2025;28(9):1594-1603. [Content Brief]
- [3]. Mohebali N, et al. Vernodalin induces apoptosis through the activation of ROS/JNK pathway in human colon cancer cells. Journal of biochemical and molecular toxicology. 2020 Dec;34(12):e22587. [Content Brief]
- [4]. Zhou J, et al. Interaction of vernodalin with p38 mitogen-activated protein kinase (p38 MAPK) and subsequent effects in lung cancer cell model. International journal of biological macromolecules. 2025 Jun;311(Pt 1):143413. [Content Brief]
- [5]. Kimani NM, et al. Sesquiterpene Lactones from Vernonia cinerascens Sch. Bip. and Their in Vitro Antitrypanosomal Activity. Molecules (Basel, Switzerland). 2018 Jan 27;23(2):248. [Content Brief]
- [6]. Thongnest S, et al. Vernodalidimer L, a sesquiterpene lactone dimer from Vernonia extensa and anti-tumor effects of vernodalin, vernolepin, and vernolide on HepG2 liver cancer cells. Bioorganic chemistry. 2019 Nov;92:103197. [Content Brief]
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