| Field | Specification |
|---|---|
| Target | |
| Alternative names | Nymphaeol A; Propolin C |
| CAS no. | |
| Applications | |
| Source | Plant — Scrophulariaceae Paulownia tomentosa (Thunb.) Steud. |
| Molecular weight | |
| Molecular formula | C25H28O6 |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Diplacone is an orally active geranyl flavanone isolated from the fruits of Paulownia tomentosa, also known as Nymphaeol A or Propolin C. It lowers COX-2 levels, increases the pro-MMP2/MMP2 ratio, and induces ferroptosis-mediated cell death, while enhancing mitochondrial Ca2+ influx and reactive oxygen species production; it also shows anti-inflammatory and free-radical-scavenging activity relevant to ulcerative colitis and non-small cell lung cancer research[1][2][3]. It is supplied as a white to off-white solid (C25H28O6, MW 424.49) at 98.38% purity.
Physical & Chemical Properties
| CAS Number | 73676-38-7 |
|---|---|
| Molecular Formula | C25H28O6 |
| Molecular Weight | 424.49 g/mol |
| Purity | 98.38% |
| Appearance | Solid |
| Color | White to off-white |
| Structure Classification | Flavonoids Flavones |
| SMILES | OC1=C2C(O[C@H](C3=CC(O)=C(C=C3)O)CC2=O)=CC(O)=C1C/C=C(C)/CC/C=C(C)\C |
| Target | COX-2, MMP-2 |
| Signaling Pathway | Immunology/Inflammation; NF-κB; Metabolic Enzyme/Protease; Membrane Transporter/Ion Channel; Neuronal Signaling; Apoptosis |
| Initial Source | Plant — Scrophulariaceae Paulownia tomentosa (Thunb.) Steud. |
| Storage | Powder: -20°C, 3 years; 4°C, 2 years. In solvent: -80°C, 6 months; -20°C, 1 month. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Biological Activity
IC50 & Target[1]
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
Diplacone inhibits LPS-induced inflammatory responses and reduces COX-2 expression in mouse macrophages[1]. When pre-incubated for 1 h before lipopolysaccharide stimulation at 10-20 μM, Diplacone downregulates the gene expression of the LPS-induced pro-inflammatory factors TNF-α and MCP-1 and upregulates expression of the anti-inflammatory gene ZFP36 that LPS induces. In macrophages differentiated from the human monocytic leukemia cell line THP-1, it doubles total TNF-α mRNA production, halves total MCP-1 mRNA production, and slightly raises total ZFP36 mRNA production[2]. In human non-small cell lung cancer A549 cells, Diplacone (5-40 μM; 24-48 h) potently inhibits viability, with IC50 values of 10.6 μM (24 h) and 7.9 μM (48 h)[3]. At 20-40 μM for 1 min, Diplacone raises the cytoplasmic Ca2+ concentration in A549 non-small cell lung cancer cells[3]. In non-small cell lung cancer A549 cells, 3-24 h of exposure to Diplacone at 20-40 μM induces loss of mitochondrial membrane potential[3]. Exposure of non-small cell lung cancer A549 cells to Diplacone at 40 μM for 3-24 h induces time-dependent upregulation of ATF3 protein expression[3].
Real Time qPCR[2]
| Cell Line | Differentiated THP-1 human monocytic leukaemia cell line-derived macrophages |
|---|---|
| Concentration | 10 μM; 20 μM |
| Incubation Time | 1 h (pre-incubation); 1, 2, 4, 6, 10, 24 h (post-LPS stimulation harvest) |
| Result | Significantly decreased TNF-α gene expression at 2 h post-LPS (P < 0.001) and significantly increased it at 4, 10, and 24 h post-LPS (P < 0.05) at 10 μM. Significantly decreased TNF-α gene expression at 2 h post-LPS (P < 0.001), significantly decreased it at 1 h post-LPS (P < 0.05), and significantly increased it at 24 h post-LPS (P < 0.05) at 20 μM. Significantly decreased MCP-1 gene expression at 4 h post-LPS (P < 0.0005), 6 h post-LPS (P < 0.0001), and 10 h post-LPS (P < 0.0001) at 10 μM. Significantly decreased MCP-1 gene expression at 4 h post-LPS (P < 0.0001), 6 h post-LPS (P < 0.0001), and 10 h post-LPS (P < 0.0001) at 20 μM. |
Cell Viability Assay[3]
| Cell Line | A549 human non-small cell lung cancer cells |
|---|---|
| Concentration | 5-40 μM |
| Incubation Time | 24 h; 48 h |
| Result | Inhibited A549 cell viability in a dose-dependent manner. Reached IC50 values of 10.6 μM (24 h) and 7.9 μM (48 h). |
Western Blot Analysis[3]
| Cell Line | A549 human non-small cell lung cancer cells |
|---|---|
| Concentration | 40 μM |
| Incubation Time | 3, 6, 9, 12, 24 h |
| Result | Increased ATF3 protein expression in a time-dependent manner, with relative expression levels of 2.75-fold (3 h), 3.58-fold (6 h), 2.87-fold (9 h), 2.9-fold (12 h), and 3.2-fold (24 h) compared to control. |
In Vivo
In Wistar rats, Diplacone (25 mg/kg; i.g.; given 48 h and 24 h before colitis induction, then every 24 h during DSS exposure) significantly reduces colitis severity. Relative to untreated DSS-exposed rats, the treatment achieves a statistically significant drop in disease activity index, along with COX-2 levels that are 55.9% lower and a pro-MMP2/MMP2 ratio that is 50.7% higher[1].
| Animal Model | Wistar rats (male, 180-220 g, ulcerative colitis induced by 10% DSS in drinking water for 5 days)[1] |
|---|---|
| Dosage | 25 mg/kg |
| Administration | i.g.; 48 h and 24 h pre-colitis induction, then every 24 h during DSS exposure |
| Result | Ameliorated colitis symptoms (diarrhea, rectal bleeding) and delayed symptom onset. Showed the lowest disease activity index (DAI) on the final day of the experiment, with a statistically significant reduction compared to the DSS-only group (### p < 0.001). Reduced colon weight/length ratio increase to 20.4% relative to the intact group. Reduced colonic COX-2 levels by 55.9% compared to the DSS-only group. Increased the pro-MMP2/MMP2 ratio by 50.7% compared to the DSS-only group. Reduced colonic levels of antioxidant enzymes SOD2 and CAT. Resulted in an 87.5% survival rate (1 of 8 rats died). |
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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