Daidzein

Names

[ CAS No. ]:
486-66-8

[ Name ]:
Daidzein

[Synonym ]:
4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-
k251b
K 251-6
MFCD00016954
Tatoin
Soybean Extract
7-Hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (7-Hydroxy-3-(4-hydroxyphenyl)chromone
4',7-Dihydroxyisoflavone
Daidzeol
7-Hydroxy-3-(4-hydroxy phenyl) chromone
EINECS 207-635-4
7,4'-dihydroxyisoflavone
isoaurostatin
Daizeol
Daidzein
Daidsein

Biological Activity

[Description]:

Daidzein is a soy isoflavone, which acts as a PPAR activator.

[Related Catalog]:

Research Areas >> Endocrinology

Natural Products >> Flavonoids

[Target]

PPAR-α

PPAR-γ

[In Vitro]

In 3T3-L1 adipocytes, Daidzein inverses the attenuation of adiponectin gene expression by co-culture, and these effects are inhibited by the PPAR-γ specific inhibitor. Daidzein attenuates the reduction of adiponectin expression in adipocytes, and a PPAR-γ specific inhibitor abrogated this effect. Direct activation of PPAR-α and-γ by Daidzein is confirmed by a luciferase reporter assay. In HEK293T cells, Daidzein significantly increases PPAR-α transcriptional activity in a concentration-dependent manner. Although an obvious dose-dependency is not observed in PPAR-γ transcriptional activity, Daidzein also significantly increases PPAR-γ transcriptional activity over a similar range of concentrations at which Daidzein enhanced PPAR-α transcriptional activity, with a maximum increase at 25 μM[1]. Daidzein is a soy isoflavone, which upregulates the expression of Abcg1, and it promotes axonal outgrowth in cultured hippocampal neurons via estrogen receptor signaling. Daidzein is a major component of soy with structural similarity to estrogen. It exerts an anti-inflammatory effect, lowers lipid levels, and increases mitochondrial biogenesis. As an activator of nuclear receptor peroxisome proliferator-activated receptors (PPARs), Daidzein enhances transcription of PPARs-dependent genes, including liver X receptors (LXRs, Nr1h gene family in mice). Incubation with different concentrations of Daidzein, from 5 to 100 μM, increases APOE transcriptional activity[2].

[In Vivo]

Treating Apoe KO mice with Daidzein increases Lxr and Abca1 gene expression at 1 month after stroke, showing that the absence of ApoE does not interfere with other cholesterol homeostasis genetic programs. Therefore, the findings suggest that Daidzein-induced ApoE upregulation is a critical component in fostering functional recovery in chronic stroke[2].

[Cell Assay]

HEK293T cells are plated on 24-well plates at a cell density of approximately 2.5×104 cells/well and are grown to 70-80% confluence. Cells are then transiently transfected with a PPAR-α or PPAR-γ expression plasmid, and a plasmid containing the luciferase gene under the control of three tandem PPAR response elements (PPRE × 3 TK-luciferase) using an X-treme GENE HP DNA Transfection Reagent. Renilla luciferase control vectors are co-transfected to control for transfection efficiency. After transfection, cells are cultured for another 24 h in medium containing DMSO or various concentrations (6.25, 12.5, 25 μM) of Daidzein. Cells are lysed, and luciferase activity is measured and expressed as fold induction, that is normalized to the activity of the renilla luciferase control plasmid[1].

[Animal admin]

Mice[2] Experiments are performed in 10- to 11-week-old male C57 (C57 bl/6) and Apoe KO (C57 background) mice. For long-term stroke recovery, mice receive Moxifloxacin (100 mg/kg) for 3 d. The prophylactic antibiotic treatment is shown to effectively reduce mortality in an animal model of stroke by attenuating peripheral infection. In addition, saline is subcutaneously administered daily, and hydrogel (Clear H2O) is given to prevent dehydration. With the implementation of poststroke care (antibiotic regimen, rehydration, and feeding hydrogels with soft diet) during the acute period (<1 week), mice start to regain their body weight by day 5 and continue to recover from stroke. Animals are randomly selected for vehicle or Daidzein treatment. Vehicle or Daidzein (10 mg/kg) is administered subcutaneously within 30 min of reperfusion after confirming the reperfusion of blood flow, daily for 7 d and then every other day up to 1 month.

[References]

[1]. Sakamoto Y1, et al. The Dietary Isoflavone Daidzein Reduces Expression of Pro-Inflammatory Genes through PPARα/γ and JNK Pathways in Adipocyte and Macrophage Co-Cultures. PLoS One. 2016 Feb 22;11(2):e0149676.

[2]. Kim E, et al. Daidzein Augments Cholesterol Homeostasis via ApoE to Promote Functional Recovery in Chronic Stroke. J Neurosci. 2015 Nov 11;35(45):15113-26.

[Related Small Molecules]

GW9662 | Retinoic acid | Elafibranor | GW501516 | Troglitazone | T0070907 | Pemafibrate | CDDO-Im | Wy-14643 | GW0742 | GW1929 | FH535 | Icariin | Fisetin | GSK0660

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
512.8±50.0 °C at 760 mmHg

[ Melting Point ]:
315-323°C (dec.)

[ Molecular Formula ]:
C₁₅H₁₀O₄

[ Molecular Weight ]:
254.238

[ Flash Point ]:
201.2±23.6 °C

[ Exact Mass ]:
254.057907

[ PSA ]:
70.67000

[ LogP ]:
2.78

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.699

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
insoluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ3100040

CHEMICAL NAME :: 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-

CAS REGISTRY NUMBER :: 486-66-8

BEILSTEIN REFERENCE NO. :: 0231523

LAST UPDATED :: 199709

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C15-H10-O4

MOLECULAR WEIGHT :: 254.25

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 13,51,1979

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319

[ Precautionary Statements ]:
P280-P305 + P351 + P338-P337 + P313

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/38

[ Safety Phrases ]:
S24-S26-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DJ3100040

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Comparing morphological, chemical and anti-diabetic characteristics of Puerariae Lobatae Radix and Puerariae Thomsonii Radix.

J. Ethnopharmacol. 164 , 53-63, (2015)

Puerariae Lobatae Radix (PLR) and Puerariae Thomsonii Radix (PTR) are traditional Chinese medicines used for the treatment of diabetes and cardiovascular diseases. These two herbs are used interchange...

A nicotinic receptor-mediated anti-inflammatory effect of the flavonoid rhamnetin in BV2 microglia.

Fitoterapia 98 , 11-21, (2014)

The alpha7 nicotinic acetylcholine receptor (nAChR) is a potential target in neuroinflammation. Screening a plant extract library identified Solidago nemoralis as containing methyl-quercetin derivativ...

A novel UHPLC method for the rapid and simultaneous determination of daidzein, genistein and equol in human urine.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 1005 , 1-8, (2015)

This work reports on a novel method involving reverse-phased ultra-high performance liquid chromatography (UHPLC) plus a spectrophotometric photodiode array/fluorescence (FLR) detection system for det...