Diplacone (Synonyms: Nymphaeol A; Propolin C)

Cat. No.: HY-N16129 Purity: 98.38%: Data Sheet
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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.

For research use only. We do not sell to patients.

Diplacone Chemical Structure

CAS No. : 73676-38-7

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COX COX-1 COX-2 COX-3

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N-type calcium channel L-type calcium channel P/Q-type calcium channel T-type calcium channel Calcium Channel

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MMP-1 MMP-2 MMP-3 MMP-8 MMP-9 MMP-13 MMP-14 MMP-17 ADAM10 ADAM17 MMP-7 MMP-12 MMP-10 MMP ADAM8 MMP-19

Biological Activity
Purity & Documentation
References
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Description

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]

In Vitro

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.

In Vivo

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).

Molecular Weight

424.49

Formula

C₂₅H₂₈O₆

CAS No.

73676-38-7

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

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Purity & Documentation

Purity: 98.38%

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Data Sheet (276 KB) SDS (251 KB)

COA (245 KB) HNMR (279 KB) LCMS (91 KB)

Handling Instructions (2659 KB)

References

[1]. Vochyánová Z, et al. Diplacone and mimulone ameliorate dextran sulfate sodium-induced colitis in rats. Fitoterapia. 2015;101:201-207. [Content Brief]

[2]. Hosek J, et al. Effect of diplacone on LPS-induced inflammatory gene expression in macrophages. Folia Biol (Praha). 2010;56(3):124-130.

[3]. Kang MJ, et al. Diplacone Isolated from Paulownia tomentosa Mature Fruit Induces Ferroptosis-Mediated Cell Death through Mitochondrial Ca2+ Influx and Mitochondrial Permeability Transition. Int J Mol Sci. 2023 Apr 11;24(8):7057. [Content Brief]

Diplacone Related Classifications

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Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

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Diplacone (Synonyms: Nymphaeol A; Propolin C)

Diplacone Related Antibodies

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