1. Immunology/Inflammation NF-κB Metabolic Enzyme/Protease Membrane Transporter/Ion Channel Neuronal Signaling Apoptosis
  2. COX Reactive Oxygen Species (ROS) Calcium Channel Ferroptosis Mitochondrial Metabolism MMP
  3. Diplacone

Diplacone  (Synonyms: Nymphaeol A; Propolin C)

製品番号: HY-N16129 純度: 98.38%
COA 取扱説明書 Technical Support

Diplacone is an orally active geranyl flavanone. It is isolated from the fruits of Paulownia tomentosa. Diplacone reduces COX-2 levels and increases the pro-MMP2/MMP2 ratio. It induces ferroptosis-mediated cell death. Diplacone enhances mitochondrial Ca2+ influx and ROS production. It possesses anti-inflammatory and free radical-scavenging activities. Diplacone can be used in research related to ulcerative colitis and non-small cell lung cancer.

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Diplacone

Diplacone 構造式

CAS 番号 : 73676-38-7

容量 価格(税別) 在庫状況 数量
1 mg $520 在庫あり
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製品説明

Diplacone is an orally active geranyl flavanone. It is isolated from the fruits of Paulownia tomentosa. Diplacone reduces COX-2 levels and increases the pro-MMP2/MMP2 ratio. It induces ferroptosis-mediated cell death. Diplacone enhances mitochondrial Ca2+ influx and ROS production. It possesses anti-inflammatory and free radical-scavenging activities. Diplacone can be used in research related to ulcerative colitis and non-small cell lung cancer[1][2][3].

IC50 & Target[1]

COX-2

 

MMP-2

 

Cellular Effect
Cell Line Type Value Description References
A2780 IC50
5.5 μg/mL
Compound: 4
Cytotoxicity against human A2780 cells
Cytotoxicity against human A2780 cells
[PMID: 15787448]
A2780cisR IC50
10.5 μM
Compound: 10
Antiproliferative activity against drug-sensitive human A2780 cells
Antiproliferative activity against drug-sensitive human A2780 cells
[PMID: 17326683]
A549 IC50
4 μM
Compound: Nymphaeol A
Growth inhibition of human A549 cells
Growth inhibition of human A549 cells
[PMID: 28814374]
BC IC50
2.7 μg/mL
Compound: 4
Cytotoxicity against human BC cells
Cytotoxicity against human BC cells
[PMID: 15974621]
BJ EC50
5.9 μM
Compound: 8
Cytotoxicity against human BJ cells assessed as viable cells after 72 hrs by calcein AM assay
Cytotoxicity against human BJ cells assessed as viable cells after 72 hrs by calcein AM assay
[PMID: 20192247]
CCRF-CEM EC50
3.2 μM
Compound: 8
Cytotoxicity against human CEM cells assessed as viable cells after 72 hrs by calcein AM assay
Cytotoxicity against human CEM cells assessed as viable cells after 72 hrs by calcein AM assay
[PMID: 20192247]
HeLa EC50
<10 μM
Compound: 8
Cytotoxicity against human HeLa cells assessed as viable cells after 72 hrs by calcein AM assay
Cytotoxicity against human HeLa cells assessed as viable cells after 72 hrs by calcein AM assay
[PMID: 20192247]
KB IC50
4.6 μg/mL
Compound: 4
Cytotoxicity against human KB cells
Cytotoxicity against human KB cells
[PMID: 15974621]
MCF7 EC50
<10 μM
Compound: 8
Cytotoxicity against human MCF7 cells assessed as viable cells after 72 hrs by calcein AM assay
Cytotoxicity against human MCF7 cells assessed as viable cells after 72 hrs by calcein AM assay
[PMID: 20192247]
NCI-H187 IC50
1.5 μg/mL
Compound: 4
Cytotoxicity against human NCI-H187 cells
Cytotoxicity against human NCI-H187 cells
[PMID: 15974621]
RPMI-8226 EC50
<10 μM
Compound: 8
Cytotoxicity against human RPMI8226 cells assessed as viable cells after 72 hrs by calcein AM assay
Cytotoxicity against human RPMI8226 cells assessed as viable cells after 72 hrs by calcein AM assay
[PMID: 20192247]
THP-1 EC50
<10 μM
Compound: 8
Cytotoxicity against human THP1 cells after 72 hrs by erythosin B staining method
Cytotoxicity against human THP1 cells after 72 hrs by erythosin B staining method
[PMID: 20192247]
THP-1 IC50
>10 μM
Compound: 22
Cytotoxicity against human THP1 cells assessed as cell viability after 24 hrs by WST assay
Cytotoxicity against human THP1 cells assessed as cell viability after 24 hrs by WST assay
[PMID: 25735399]
U-266 EC50
2.4 μM
Compound: 8
Cytotoxicity against human U266 cells assessed as viable cells after 72 hrs by calcein AM assay
Cytotoxicity against human U266 cells assessed as viable cells after 72 hrs by calcein AM assay
[PMID: 20192247]
Vero IC50
3.8 μg/mL
Compound: 4
Cytotoxicity against african green monkey Vero cells
Cytotoxicity against african green monkey Vero cells
[PMID: 15974621]
体外実験

Diplacone inhibits LPS-induced inflammatory responses and reduces the expression of COX-2 in mouse macrophages[1].
Diplacone (pre-incubated for 1 h before lipopolysaccharide stimulation at concentrations of 10-20 μM) downregulates the gene expression of LPS-induced pro-inflammatory factors TNF-α and MCP-1, and upregulates the expression of LPS-induced anti-inflammatory gene ZFP36. In macrophages differentiated from the THP-1 human monocytic leukemia cell line, it doubles the total production of TNF-α mRNA, halves the total production of MCP-1 mRNA, and slightly increases the total production of ZFP36 mRNA[2].
Diplacone (5-40 μM; 24-48 h) potently inhibits the viability of human non-small cell lung cancer A549 cells, with an IC50 value of 10.6 μM at 24 h and 7.9 μM at 48 h[3].
Diplacone (20-40 μM; 1 min) increases the cytoplasmic Ca2+ concentration in non-small cell lung cancer A549 cells[3].
Diplacone (20-40 μM; 3-24 h) induces loss of mitochondrial membrane potential in non-small cell lung cancer A549 cells[3].
Diplacone (40 μM; 3-24 h) induces time-dependent upregulation of ATF3 protein expression in non-small cell lung cancer A549 cells[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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.
体内実験

Diplacone (25 mg/kg; i.g.; 48 h and 24 h pre-colitis induction, then every 24 h during DSS exposure) significantly reduces colitis severity in Wistar rats, achieving a statistically significant reduction in disease activity index, 55.9% lower COX-2 levels, and a 50.7% higher pro-MMP2/MMP2 ratio compared to untreated DSS-exposed rats[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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).
分子量

424.49

分子式

C25H28O6

CAS 番号
Appearance

Solid

Color

White to off-white

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

Structure Classification
Initial Source
輸送条件

Room temperature in continental US; may vary elsewhere.

保管条件
Powder -20°C 3 years
  4°C 2 years
In solvent -80°C 6 months
  -20°C 1 month
純度とドキュメンテーション
参考文献
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製品名:
Diplacone
製品番号:
HY-N16129
数量:
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