Cubebin
Cubebin ((-)-Cubebin), a dibenzyl butyrolactone lignan, is an orally active AChE inhibitor. Cubebin binds to active sites of NF-κB, TNF-α, and TGF-β1 via hydrogen and hydrophobic interactions, obstructing critical residues to inhibit pro-inflammatory or renal fibrosis-related activity. Cubebin enhances p38 MAPK phosphorylation to increase tyrosinase gene expression, stimulating melanogenesis via elevated tyrosinase activity, expression, and mRNA levels. Cubebin reduces oxidative stress via enhanced endogenous antioxidant enzyme activity and inhibited lipid peroxidation, regulates lipid metabolism, improves glycemic control, and exerts renoprotective effects via reduced renal dysfunction markers and improved renal architecture. Cubebin shows antimicrobial activity. Cubebin exerts larvicidal activity against Angiostrongylus cantonensis larvae, with no cytotoxicity toward monkey or human cell lines or Caenorhabditis elegans. Cubebin can be used for the research of diabetic nephropathy, melanoma, colon adenocarcinoma, neuroangiostrongyliasis, Alzheimer’s disease (AD) and depression.
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- No. CAS: 18423-69-3
- Fòrmula: C20H20O6
- Peso molecular:356.37
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Almacenamiento:
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Actividad biológica
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AChE |
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| MDCK | IC50 |
>200 μM
Compound: 1
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Inhibition of human NET expressed in MDCK cells using [3H]-norepinephrine as substrate after 10 mins by scintillation counting
Inhibition of human NET expressed in MDCK cells using [3H]-norepinephrine as substrate after 10 mins by scintillation counting
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[PMID: 24112084] |
| MDCK | IC50 |
>200 μM
Compound: 1
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Inhibition of human SERT expressed in MDCK cells using [3H]-serotonin as substrate after 10 mins by scintillation counting
Inhibition of human SERT expressed in MDCK cells using [3H]-serotonin as substrate after 10 mins by scintillation counting
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[PMID: 24112084] |
| MDCK | IC50 |
12 μM
Compound: 1
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Inhibition of human DAT expressed in MDCK cells using [3H]-dopamine as substrate after 10 mins by scintillation counting
Inhibition of human DAT expressed in MDCK cells using [3H]-dopamine as substrate after 10 mins by scintillation counting
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[PMID: 24112084] |
Cubebin (2-20 μM; 72 h) stimulates melanogenesis in a concentration-dependent manner in murine B16 melanoma cells, with no significant impact on cell proliferation at 2, 5, and 10 μM[3].
Cubebin (10 μM; 24-96 h) enhances tyrosinase activity, and increases intracellular melanin amount significantly starting at 48 h and reaching maximum levels at 72 and 96 h in murine B16 melanoma cells[3].
Cubebin (10 μM; 24-72 h) enhances tyrosinase protein expression, reaching a 6.2-fold increase relative to pre-treated cells at 48 h in murine B16 melanoma cells[3].
Cubebin (10 μM; 12-48 h) increases tyrosinase mRNA expression, reaching a 1.8-fold increase relative to pre-treated cells at 12 h in murine B16 melanoma cells[3].
Cubebin (10 μM; 2-12 h) significantly enhances p38 MAPK phosphorylation at 4-8 h, with no impact on ERK1/2 or p70 S6K1 phosphorylation in murine B16 melanoma cells[3].
Cubebin (2.8-280 μM; 24-72 h) is non-cytotoxic to HT29 cells at 2.8 and 28 μM for 24, 48, or 72 h, but induces significant cytotoxicity (≈50% viability reduction at 24 h) at 280 μM for 24, 48, or 72 h[4].
Cubebin (50-200 μM; 24 h) shows no cytotoxicity toward Vero monkey kidney epithelial cells or HaCaT human keratinocytes at concentrations up to 200 μM, resulting in high selectivity indices against Angiostrongylus cantonensis larvae[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:murine B16 melanoma cells
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Concentration:2, 5, 10, 20 μM
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Incubation Time:72 h
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Result:Stimulated melanogenesis in a concentration-dependent manner.
Significantly increased melanin amount at 2 μM relative to control cells.
Showed greater significant increases in melanin amount at 5, 10, and 20 μM relative to control cells.
Showed no significant effects on cell proliferation at 2, 5, and 10 μM.
Slightly decreased cell proliferation at 20 μM.
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Cell Line:murine B16 melanoma cells
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Concentration:10 μM
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Incubation Time:24, 48, 72 h
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Result:Enhanced tyrosinase expression to 4.9-fold of pre-treated cells at 24 h.
Enhanced tyrosinase expression to 6.2-fold of pre-treated cells at 48 h.
Enhanced tyrosinase expression to 1.7-fold of pre-treated cells at 72 h.
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Cell Line:murine B16 melanoma cells
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Concentration:10 μM
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Incubation Time:12, 24, 48 h
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Result:Increased tyrosinase mRNA expression 1.8-fold relative to pre-treated cells at 12 h.
Showed 1.7-fold increases in tyrosinase mRNA expression at 24 and 48 h relative to pre-treated cells.
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Cell Line:murine B16 melanoma cells
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Concentration:10 μM
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Incubation Time:2, 4, 6, 8, 10, 12 h
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Result:Significantly enhanced phosphorylation of p38 MAPK at 4-8 h after treatment.
Showed no effects on the phosphorylation levels of ERK1/2 or p70 S6K1.
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Cell Line:murine B16 melanoma cells
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Concentration:10 μM
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Incubation Time:12 h
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Result:Increased tyrosinase mRNA expression 1.9-fold relative to pre-treated cells.
Showed complete block of this cubebin-induced increase in tyrosinase mRNA expression when co-treated with SB203580.
Cubebin (10 mg/kg; p.o.; single dose) inhibits carrageenin-induced rat paw edema by 53%, with statistically significant anti-inflammatory activity[2].
Cubebin (10 mg/kg; p.o.; single dose) inhibits PGE2-induced rat paw edema by 20%, with statistically significant anti-inflammatory activity[2].
Cubebin (10 mg/kg; p.o.; single dose) inhibits serotonin-induced rat paw edema by 23%, with statistically significant anti-inflammatory activity[2].
Cubebin (10 mg/kg; p.o.; single dose) does not produce a statistically significant reduction in carrageenin-induced peritoneal cell migration in rats, with only 12% inhibition observed[2].
Cubebin (10 mg/kg; p.o.; single dose) inhibits acetic acid-induced writhing in mice by 50%, with statistically significant peripheral antinociceptive activity[2].
Cubebin (10 mg/kg; p.o.; single dose) inhibits PGI2-induced writhing in mice by 71%, with statistically significant peripheral antinociceptive activity[2].
Cubebin (10-40 mg/kg; i.g.; daily; 35 days) significantly alleviates CUMS-induced depression-like behavior in male C57BL/6 mice by restoring brain neurotransmitter levels, reducing neuronal tissue damage, and normalizing gut microbiota composition and function[6].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Wistar (male, 8-10-week-old, 180 g, Streptozotocin-induced diabetic nephropathy)[1]
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Dosage:10 mg/kg; 20 mg/kg
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Administration:p.o.; daily; 8 weeks
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Result:Significantly reduced fasting blood glucose levels and restored serum insulin levels.
Significantly reduced HbA1c levels.
Significantly reduced total cholesterol and triglyceride levels, and increased high-density lipoprotein levels.
Significantly reduced serum creatinine, blood urea nitrogen, and 24-hour urine volume.
Significantly increased kidney superoxide dismutase, catalase, and glutathione reductase activity, and reduced kidney malondialdehyde levels.
Significantly reduced kidney tumor necrosis factor-α, interleukin-1β, interleukin-6, nuclear factor-kappa B, and transforming growth factor-β1 levels.
Significantly improved renal histopathology, restoring normal glomerular and tubular structures and reducing lesions including glomerular basement membrane thickening, cellular necrosis, interstitial inflammation, and hemorrhage.
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Animal Model:C57BL/6 (male, 6-8 weeks old, 18-22 g, CUMS-induced depression-like behavior)[6]
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Dosage:10 mg/kg; 20 mg/kg; 40 mg/kg
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Administration:i.g.; daily; 35 days
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Result:Significantly increased total distance traveled in the open field test and sucrose preference percentage, and significantly decreased immobility time in the tail suspension test and forced swimming test compared to the model group.
Reduced pathological damage to hippocampal and cortical neuronal cells, with restored arrangement, number, and morphology of neurons compared to the model group; significantly increased cortical neuron count in the 40 mg/kg group compared to the model group.
Significantly increased norepinephrine (NE) and dopamine (DA) levels in cortical tissue in the 20 mg/kg and 40 mg/kg groups compared to the model group; significantly increased NE levels in hypothalamic tissue in all dose groups, and significantly increased DA levels in hypothalamic tissue in the 20 mg/kg group compared to the model group; significantly increased serotonin (5-HT) levels in cortical tissue in all dose groups compared to the model group.
Reversed CUMS-induced gut microbiota alterations, including reduced relative abundance of Clostridium, Dorea, Ruminococcus, Eubacterium, Escherichia, Phascolarctobacterium, Lactobacillus, Roseburia, Coprococcus, Sutterella, Akkermansia, Parabacteroides, and Allobaculum, and increased relative abundance of Prevotella, Dehalobacterium, Flavobacterium, and Blautia compared to the model group.
Reversed CUMS-induced dysregulation of gut microbiota metabolic pathways, with restored expression levels of KEGG and COG pathway sequences toward control group levels.
Chemical Information
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No. CAS 18423-69-3
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Peso molecular 356.37
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Fòrmula C20H20O6
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SMILES
O[C@@H]1[C@@H]([C@H](CO1)CC2=CC=C3C(OCO3)=C2)CC4=CC=C5C(OCO5)=C4
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Synonyms
(-)-Cubebin
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Structure Classification
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Initial Source
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
Please store the product under the recommended conditions in the Certificate of Analysis.
Pureza y Documentación
Referencias
[1]. Syed RU, et al. Effect of cubebin against streptozotocin-induced diabetic nephropathy rats via inhibition TNF-α/NF-κB/TGF-β: in vivo and in silico study. Sci Rep. 2025;15(1):4369. Published 2025 Feb 5. [Content Brief]
[2]. Bastos JK, et al. Anti-inflammatory activity of cubebin, a lignan from the leaves of Zanthoxyllum naranjillo Griseb. J Ethnopharmacol. 2001;75(2-3):279-282. [Content Brief]
[3]. Hirata N, et al. Mechanism of the melanogenesis stimulation activity of (-)-cubebin in murine B16 melanoma cells. Bioorg Med Chem. 2007;15(14):4897-4902. [Content Brief]
[4]. Niwa AM, et al. Evaluation of lignan (-)-cubebin extracted from Piper cubeba on human colon adenocarcinoma cells (HT29). J Toxicol Environ Health A. 2016;79(2):92-100. [Content Brief]
[5]. eixeira TR, et al. Cubebin, a Lignan Isolated from Drimys andina, Exhibits Potent and Selective Antiparasitic Activity against Angiostrongylus cantonensis. ACS Omega. 2025 Jul 11;10(28):31161-31169. [Content Brief]
[6]. Wan M, et al. Cubebin alleviates chronic stress-induced depression-like behavior in mice by regulating the gut microbiome. Eur J Pharmacol. 2025;994:177384. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Cubebin Related Classifications
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