Daidzin

For research use only.

Catalog No.S2289 Synonyms: Daidzoside, Daidzein 7-O-glucoside, Daidzein 7-glucoside

Daidzin Chemical Structure

CAS No. 552-66-9

Daidzin (Daidzoside, Daidzein 7-O-glucoside, Daidzein 7-glucoside), a natural organic compound in the class of phytochemicals known as isoflavones, is a potent and selective inhibitor of human mitochondrial aldehyde dehydrogenase and inhibits ALDH-I selectively (Ki=20 nM); at least 500 times less effective against ALDH-Ⅱ, the cytosolic isozyme (Ki=10 μM).

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Biological Activity

Description Daidzin (Daidzoside, Daidzein 7-O-glucoside, Daidzein 7-glucoside), a natural organic compound in the class of phytochemicals known as isoflavones, is a potent and selective inhibitor of human mitochondrial aldehyde dehydrogenase and inhibits ALDH-I selectively (Ki=20 nM); at least 500 times less effective against ALDH-Ⅱ, the cytosolic isozyme (Ki=10 μM).
Targets
ALDH-Ⅰ [3]
(Cell-free assay)
20 nM(Ki)
In vitro

Daidzin, a glycoside of daidzein, increases the transcriptional activity of RARα and RARγ but does not bind to the RARs[1]. Daidzin does not inhibit human class Ⅰ, Ⅱ, or Ⅲ alcohol dehydrogenases, nor does it have any significant effect on biological systems that are known to be affected by other isoflavones. Daidzin inhibits human ALDH-I and ALDH-II in a concentration-dependent manner. Daidzin inhibits both ALDH-I and ALDH-II in an apparently competitive manner with Ki values of 40 nM and 20 μM, respectively, and it inhibits ALDH-I uncompetitively with respect to NAD+. The inhibition of ALDH-I by daidzin is reversible[3].
In vivo Daidzin has no effect on alcohol-metabolizing enzymes(i.e., ADH and ALDH) when given to rats intragastrically. Chronic daidzin administration exerts an effect on alcohol pharmacokinetics, although the effect is less pronounced than when the compound is administered concurrently with ethanol.The compound is shown to shorten sleep time if ethanol is given intragastrically, but not when given intraperitoneally, indicating absence of effect on ethanol elimination rate. Daidzin delays ethanol absorption and lessens alcohol intoxication. The compound is shown to suppress the levels of BAC(blood alcohol concentration) for the first 3 hr after alcohol ingestion in both fasted and fed rats. These effects of daidzin may in part be due to its antioxidant activity[2].

Protocol

Cell Research:

[1]
- Collapse
  • Cell lines: CV-1 cells
  • Concentrations: 0.5, 1, 10, 50, and 100 μM
  • Incubation Time: 24 h
  • Method:

    CV-1 cells are transfected with 100 ng ERE-Luc and 50 ng ER-RARα or ER-RARγ. Transfected cells are treated with the indicated isoflavone at 0.5, 1, 10, 50, and 100 μM for 24 h. The β-Gal activity is used to normalize luciferase activity. 


    (Only for Reference)
Animal Research:

[2]
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  • Animal Models: Male Wistar rats
  • Dosages: 30 mg/kg
  • Administration: intragastrically
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 83 mg/mL (199.33 mM)
Ethanol 4 mg/mL (9.6 mM)
Water Insoluble

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 416.38
Formula

C21H20O9

CAS No. 552-66-9
Storage powder
in solvent
Synonyms Daidzoside, Daidzein 7-O-glucoside, Daidzein 7-glucoside
Smiles C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O)O

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Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID