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Chemical Structure| 552-66-9 Chemical Structure| 552-66-9

Structure of Daidzin
CAS No.: 552-66-9

Chemical Structure| 552-66-9

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Daidzin can inhibit mitochondrial aldehyde dehydrogenase2 with IC50 of 80 nM and ALDH-I selectively (Ki=20 nM). Daidzin is purified from the root of Pueraria lobata with effective anti-atherosclerotic activities.

Synonyms: Daidzoside; NPI-031D; Daidzein 7-glucoside

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Product Details of Daidzin

CAS No. :552-66-9
Formula : C21H20O9
M.W : 416.38
SMILES Code : OC1=CC=C(C2=COC(C=C(O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)C=C4)=C4C2=O)C=C1
Synonyms :
Daidzoside; NPI-031D; Daidzein 7-glucoside
MDL No. :MFCD00017466
InChI Key :KYQZWONCHDNPDP-QNDFHXLGSA-N
Pubchem ID :107971

Safety of Daidzin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

Target
  • Dehydrogenase

    ALDH-Ⅰ, Ki:20 nM

In Vitro:

Cell Line
Concentration Treated Time Description References
Hamster liver mitochondria 0.4 μM 10 min To study the inhibitory effect of Daidzin on mitochondria-catalyzed acetaldehyde oxidation, results showed Daidzin significantly inhibited acetaldehyde oxidation with an IC50 of 0.4 μM. Proc Natl Acad Sci U S A. 1995 Sep 12;92(19):8990-3
neonatal rat cardiomyocytes 20 µM 48 h To investigate the effect of Daidzin on mitochondrial membrane potential in cardiomyocytes under high glucose conditions. Results showed that high glucose treatment significantly decreased mitochondrial membrane potential, and Daidzin further exacerbated this effect. Mol Med. 2011 Mar-Apr;17(3-4):172-9
Neuro2A cells 20 or 40 µM 12 h To study the effect of ALDH2 inhibition on alcohol-induced neuronal damage, results showed that Daidzin pretreatment exacerbated ethanol-induced cell viability reduction and oxidative stress-related PTMs. Cells. 2024 May 28;13(11):927
T84 human colon cells 10 μM 12 h Pretreatment with Daidzin exacerbated ethanol-induced cell permeability and reduced TJ/AJ proteins in T84 human colon cells. These changes were reversed by Alda-1, an ALDH2 activator. Redox Biol. 2023 Feb;59:102577.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Syrian golden hamsters Free-choice ethanol intake model Intraperitoneal injection 150 mg/kg/day Once daily for 6 days To study the effect of Daidzin on hamster ethanol intake and its impact on acetaldehyde metabolism, results showed Daidzin significantly suppressed ethanol intake (70%) without affecting acetaldehyde metabolism. Proc Natl Acad Sci U S A. 1995 Sep 12;92(19):8990-3

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.40mL

0.48mL

0.24mL

12.01mL

2.40mL

1.20mL

24.02mL

4.80mL

2.40mL

References

[1]Keung WM, Vallee BL. Kudzu root: an ancient Chinese source of modern antidipsotropic agents. Phytochemistry. 1998 Feb;47(4):499-506.

[2]Keung WM, Vallee BL. Daidzin: a potent, selective inhibitor of human mitochondrial aldehyde dehydrogenase. Proc Natl Acad Sci U S A. 1993 Feb 15;90(4):1247-51.

[3]Keung WM, Klyosov AA, Vallee BL. Daidzin inhibits mitochondrial aldehyde dehydrogenase and suppresses ethanol intake of Syrian golden hamsters. Proc Natl Acad Sci U S A. 1997 Mar 4;94(5):1675-9

[4]Xie CI, Lin RC, Antony V, Lumeng L, Li TK, Mai K, Liu C, Wang QD, Zhao ZH, Wang GF. Daidzin, an antioxidant isoflavonoid, decreases blood alcohol levels and shortens sleep time induced by ethanol intoxication. Alcohol Clin Exp Res. 1994 Dec;18(6):1443-7

[5]Xiao F, Cui H, Zhong X. Beneficial effect of daidzin in dry eye rat model through the suppression of inflammation and oxidative stress in the cornea. Saudi J Biol Sci. 2018 May;25(4):832-837

[6]Wu KC, Lin WY, Sung YT, Wu WY, Cheng YH, Chen TS, Chiang BJ, Chien CT. Glycine tomentella hayata extract and its ingredient daidzin ameliorate cyclophosphamide-induced hemorrhagic cystitis and oxidative stress through the action of antioxidation, anti-fibrosis, and anti-inflammation. Chin J Physiol. 2019 Sep-Oct;62(5):188-195

[7]Keung WM, Lazo O, Kunze L, Vallee BL. Daidzin suppresses ethanol consumption by Syrian golden hamsters without blocking acetaldehyde metabolism. Proc Natl Acad Sci U S A. 1995 Sep 12;92(19):8990-3

[8]Keung WM, Vallee BL. Daidzin: a potent, selective inhibitor of human mitochondrial aldehyde dehydrogenase. Proc Natl Acad Sci U S A. 1993 Feb 15;90(4):1247-51

 

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