Clerodin
Clerodin (3-Deoxycaryoptinol) is a natural diterpenoid compound that can be isolated from traditional Chinese medicinal plants such as Clerodendrum infortunatum. Clerodin exhibits caspase-3 regulation, apoptosis induction, cell cycle arrest, ROS induction and glutathione depletion effects, along with anti-cancer and antifeedant activities. It shows selective cytotoxicity against leukemia cells and breast cancer cells, but has no obvious toxicity to normal human blood cells and lymphocytes. Clerodin also reduces the feeding behavior of Helicoverpa armigera larvae on cabbage leaf discs, but has no significant contact toxicity to these larvae. Clerodin can be used in research related to acute monocytic leukemia and human breast cancer.
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- CAS. Nr.: 464-71-1
- Formel: C24H34O7
- Molecular Weight:434.52
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Speicherung:
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Biologische Aktivität
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Chemical Information
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Clerodin (30-150 μM) potently reduces viability of human monocytic leukemia (THP-1) cells with an IC50 of 60 μM[1].
Clerodin (60 μM) induces apoptosis-related morphological changes including nuclear condensation and apoptotic body formation in human monocytic leukemia (THP-1) cells[1].
Clerodin (60 μM) induces significant apoptosis in human monocytic leukemia (THP-1) cells, with 86.6% of cells in early or late apoptotic stages[1].
Clerodin (60 μM) increases intracellular ROS levels by ≥80% in human monocytic leukemia (THP-1) cells[1].
Clerodin (60 μM; 18 h) significantly upregulates caspase-3 gene expression 6-fold without altering Bcl-2 gene expression in human monocytic leukemia (THP-1) cells[1].
Clerodin (60 μM) activates caspase-3/7 in human monocytic leukemia (THP-1) cells[1].
Clerodin (60 μM) increases caspase-3 protein levels 5-fold and decreases Bcl-2 protein levels in human monocytic leukemia (THP-1) cells[1].
Clerodin (60 μM) induces a dose-dependent increase in cleaved caspase-3 activation (2 to 4-fold) in human monocytic leukemia (THP-1) cells[1].
Clerodin (60 μM) induces G2/M phase cell cycle arrest and increases the Sub G0/G1 apoptotic cell population in human monocytic leukemia (THP-1) cells[1].
Clerodin (60 μM) exhibits no significant cytotoxicity to ex vivo healthy human peripheral blood mononuclear cells (PBMNCs)[1].
Clerodin binds with highest affinity to human farnesyltransferase (PDB ID 1JCQ, ΔG = -8.2 kcal/mol) and second-highest affinity to human phosphoinositide 3-kinase (PDB ID 4FLH, ΔG = -7.9 kcal/mol), with weaker binding to other tested human cancer-related proteins[2].
Clerodin (0.5-100 μg/mL; 24 h) potently inhibits human breast carcinoma MCF-7 cell viability with an IC50 of 30.88 μg/mL, while showing lower toxicity to normal human lymphocyte cells (HLCs) at concentrations up to 50 μg/mL[2].
Clerodin (30.88 μg/mL; 24 h) significantly increases intracellular reactive oxygen species (ROS) generation in human breast carcinoma MCF-7 cells[2].
Clerodin significantly reduces reduced glutathione (GSH) levels and increases oxidized glutathione (GSSG) levels in human breast carcinoma MCF-7 cells, disrupting redox homeostasis[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:human monocytic leukemia (THP-1) cells
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Concentration:60 μM
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Incubation Time:18 h
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Result:Caused a significant 6-fold upregulation of caspase-3 gene expression (p<0.01) compared to untreated controls.
Showed no significant change in Bcl-2 gene expression relative to controls.
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Cell Line:human breast carcinoma MCF-7 cells, normal human lymphocyte cells (HLCs)
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Concentration:0.5-100 μg/mL
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Incubation Time:24 h
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Result:Inhibited MCF-7 cell viability in a concentration-dependent manner, with an IC50 value of 30.88 μg/mL.
Showed 51% cell viability in HLCs at 25 μg/mL and 28% cell viability at 100 μg/mL.
Exhibited minimal toxicity to HLCs at concentrations up to 50 μg/mL.
Chemical Information
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CAS. Nr. 464-71-1
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Molecular Weight 434.52
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Formel C24H34O7
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SMILES
CC(OC[C@]12[C@]3(CCC[C@]1([H])[C@]([C@@H](C[C@@H]2OC(C)=O)C)([C@]4([H])C[C@]5([H])[C@](OC=C5)([H])O4)C)CO3)=O
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Synonyms
3-Deoxycaryoptinol
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Structure Classification
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Initial Source
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Versand
Room temperature in continental US; may vary elsewhere.
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Speicherung
Please store the product under the recommended conditions in the Certificate of Analysis.
Reinheit & Dokumentation
Verweise
[1]. Nagaraj B, et al. Clerodane diterpene 3-deoxycaryoptinol (Clerodin) selectively induces apoptosis in human monocytic leukemia (THP-1) cells and upregulates apoptotic protein caspase-3. Free radical biology & medicine. 2024 Nov 20;225:925-932. [Content Brief]
[2]. Pakrashy S, et al. Bioinformatics and Network Pharmacology of the First Crystal Structured Clerodin: Anticancer and Antioxidant Potential against Human Breast Carcinoma Cell. ACS omega. 2022 Dec 27;7(51):48572-48582. [Content Brief]
[3]. Abbaszadeh G, et al. Insecticidal and antifeedant activities of clerodane diterpenoids isolated from the Indian bhant tree, Clerodendron infortunatum, against the cotton bollworm, Helicoverpa armigera. Journal of insect science (Online). 2014 Feb 26;14:29. [Content Brief]
Calculators
Konzentration (Stammlösung) × Volumen (Stammlösung) = Konzentration (Ziellösung) × Volumen (Ziellösung)
Clerodin Related Classifications
HY-N20639 Related Classifications
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