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486-66-8 Usage

Description

Different sources of media describe the Description of 486-66-8 differently. You can refer to the following data:
1. Daidzein mainly comes from leguminous plants, the seeds of soybean (dadou), red clover grass, or all Pueraria roots. Its medicinal value was first recorded in Shen Nong Ben Cao Jing 2838 BC.?Daidzein, one of the main soy isoflavones, is also the main component of radix puerariae (Gegen) which is the dry root of kudzu leguminous plants. Radix puerariae can reduce fever, produce saliva, and relieve diarrhea. Its chemical composition is complicated, including puerarin, xyloside, soy flavonoids, soybean flavonoid glycosides, beta-sitosterol, daidzin, daidzein. The main effective components are puerarin and daidzein
2. Daidzein is an isoflavone phytoestrogenic compound that has been found in soybeans and other legumes. It binds to estrogen receptor β (ERβ; Ki = 2.8 μM) but not ERα at concentrations up to 1 mM. It is estrogenic in vitro, increasing gene transcription mediated by the estrogen response element (ERE) in a reporter assay in an ERβ-dependent manner (EC50 = 2.8 μM for MCF-7 cells expressing ERβ). Daidzein is an inhibitor of carbonic anhydrase (CA) that is selective for carbonic CAVII and CAXII (Kis = 4.2 and 56 nM, respectively) over CAI, II, and IV (Kis = >10,000, >10,000, and 718.7 nM, respectively). It reduces tumor growth in a PC3 prostate cancer mouse orthotopic model when administered at a dose of 50 mg/kg per day and potentiates the effects of radiation therapy.

Chemical Properties

Off-White Crystalline Solid

Physical properties

Appearance: pale-yellow prismatic crystal. Melting point: 315–323?°C. Solubility: soluble in ethanol and ether

History

Daidzein is a kind of isoflavone compound, which was first synthetized by researchers in China. It has been widely used in drugs, food supplements, and cosmetics. Because of two phenolic hydroxyl structures, Daidzein has poor water solubility, poor liposolubility, and strong first-pass effect, leading to the low bioavailability of oral absorption, which limits its widely clinical usage. Ipriflavone is a kind of isoflavone modified from Daidzein, which has been used for the treatment of osteoporosis in Japan and some European countries. The effects of a series of amino alkoxy derivatives of ipriflavones on inhibiting the bone absorption were evaluated. The researchers found that 7-amino alkoxy derivative works best. When Daidzein was alkylated or acylated at 7-hydroxyl selectively, the stability was increased, and thus the proliferation of MCF-7 cell was inhibited.

Uses

Different sources of media describe the Uses of 486-66-8 differently. You can refer to the following data:
1. Inactive analog of Genistein (Cat. #G350000). Blocks the G1 phase of the cell cycle in Swiss 3T3 cells by inhibiting casein kinase II activity1. Daidzein has also been shown to inhibit the action of GABA on recombinant GABAA receptors2. uv max:250 nm (log e 4.44)
2. Daidzein belongs to the group of isoflavones. Daidzein and other isoflavone compounds, such as genistein, are present in a number of plants and herbs. Soy isoflavones are a group of compounds found in and isolated from the soybean. Besides functioning as

Definition

ChEBI: A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone substituted by an additional hydroxy group at position 4'.

Indications

Daidzein is mainly used for the treatment of hypertension, coronary heart disease, cerebral thrombosis, and vertigo and aids in the treatment of sudden deafness. It can also treat women with menopause syndrome.

General Description

Daidzein is an endocrine-active estrogenic isoflavone. This phytoestrogen is capable to bind to estrogen to exert estrogenic effects in vivo. It can naturally be found in soybean seed and flour.

Biological Activity

Analog of the phytoestrogen genistein (5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one ). Blocks G 1 phase cell cycle progression and is an agonist at estrogen receptors.

Biochem/physiol Actions

Soy isoflavone daidzein protects against oxidative damage in liver cells induced by 7,12-dimethylbenz[a]anthracene (DMBA). Catalase and superoxide dismutase activity, down-regulated by DMBA, was restored by daidzein.

Pharmacology

Daidzein has many kinds of pharmacological effects, such as anticancer, cardiovascular protection, estrogen- and antiestrogen-like effects, antiosteoporosis, antioxidation, improving immunity, and affecting the endocrine system. More attention has been paid by domestic and international pharmaceutical and food industries. Daidzein has obviously antibacterial effect on Staphylococcus aureus and Escherichia coli. It can also increase the weight of immune organs in mice and has anti-arrhythmic effect. The chemical structure of daidzein is very similar to the endogenous estrogen, so the estrogen-like effect is used to treat menopausal syndrome and increase the levels of osteocalcin (BGP) and also the bone mineral deposits. The clinical efficacy is similar to estrogen replacement therapy (ERT). Daidzein doesn’t induce the high expression of estrogen. It has effects on the osteoblast to reduce the bone absorption of osteoclast, thus maintains the dynamic balance of osteoblast and osteoclast, finally reduces the risk of fracture. So it is safe for usage. Daidzein can also increase the bone mineral density (BMD) and bone mineral content (BMC) of the lumbar spine, the number of trabecular bone, and bone volume fraction, improve the bone microstructure, and thus prevent the reduction of femur biomechanics in glucocorticoid-induced osteoporosis in the rat. Daidzein has an anti-hypoxia effect. The study showed that Daidzein could significantly prolong the survival time of mice in hypoxia tolerance test under normal pressure and after subcutaneous injection of isoproterenol, suggesting that Daidzein has the significant anti-hypoxia effects. Daidzein plays a protective role in myocardial hypertrophy induced by isoproterenol in rat probably by the antioxidative effects. Similarly, Daidzein may protect the ischemia-reperfusion injury in rats by increasing the antioxidative capacity. Daidzein can significantly inhibit the proliferation of two human breast cancer cells (MCF-7 and MDA-MB-231) in?vitro with the significant dose-dependent and time-dependent effects. Daidzein can markedly decrease the colony-forming ability, suggesting that Daidzein may have the effect of preventing and treating breast cancer. It was found that Daidzein has the obviously preventive effect on chloroforminduced ventricular fibrillation in mice, therapeutic effect on aconitine-induced arrhythmia in rats, as well as protective effect on the adrenaline-induced arrhythmia in rabbit. Daidzein can significantly reduce the action potential amplitude of sciatic nerve in toad in?vitro. All of the above effects were obviously dose-dependent, suggesting Daidzein has the significant anti-arrhythmic effects

Clinical Use

Daidzein can expand the coronary artery, femoral artery, and cerebral artery, increase cerebral blood flow and limb blood circulation, reduce blood viscosity and vascular resistance, decrease myocardial oxygen consumption, improve heartfunction, increase the microcirculation and blood flow to the tip, lower the blood pressure, and adjust the heart rhythm. Daidzein can be used for the treatment of hypertension, coronary heart disease, angina pectoris, myocardial infarction, cerebral thrombosis, dizziness, and sudden deafness. It can also be used for women’s menopause syndrome.

Check Digit Verification of cas no

The CAS Registry Mumber 486-66-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 6 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 486-66:
(5*4)+(4*8)+(3*6)+(2*6)+(1*6)=88
88 % 10 = 8
So 486-66-8 is a valid CAS Registry Number.
InChI:InChI=1/C15H10O4/c16-10-6-4-9(5-7-10)11-8-19-13-3-1-2-12(17)14(13)15(11)18/h1-8,16-17H

486-66-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (D2668)  Daidzein  >98.0%(HPLC)(T)

  • 486-66-8

  • 1g

  • 253.00CNY

  • Detail
  • Alfa Aesar

  • (B22877)  4',7-Dihydroxyisoflavone, 97%   

  • 486-66-8

  • 1g

  • 719.0CNY

  • Detail
  • Alfa Aesar

  • (B22877)  4',7-Dihydroxyisoflavone, 97%   

  • 486-66-8

  • 5g

  • 1593.0CNY

  • Detail
  • Alfa Aesar

  • (B22877)  4',7-Dihydroxyisoflavone, 97%   

  • 486-66-8

  • 25g

  • 5927.0CNY

  • Detail
  • USP

  • (1162421)  Daidzein  United States Pharmacopeia (USP) Reference Standard

  • 486-66-8

  • 1162421-25MG

  • 4,662.45CNY

  • Detail
  • Sigma-Aldrich

  • (16587)  Daidzein  analytical standard

  • 486-66-8

  • 16587-10MG

  • 2,046.33CNY

  • Detail
  • Sigma-Aldrich

  • (05340590)  Daidzein  primary pharmaceutical reference standard

  • 486-66-8

  • 05340590-50MG

  • 5,933.07CNY

  • Detail

486-66-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Daidzein

1.2 Other means of identification

Product number -
Other names 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:486-66-8 SDS

486-66-8Synthetic route

daidzin
552-66-9

daidzin

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
β-glucosidase, derived from Aspergillus niger In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;100%
diglycosidase, produced by Penicillium multicolor IAM7153 In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;88.5%
With sulfonated graphene oxide nanosheets In water; ethylene glycol at 105℃; for 8h; Reagent/catalyst; Sealed tube;55.7%
2,4,4'-trihydroxy deoxybenzoin
17720-60-4

2,4,4'-trihydroxy deoxybenzoin

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
With methanesulfonyl chloride In N,N-dimethyl-formamide at 60 - 70℃; for 1.5h;98%
Multi-step reaction with 2 steps
1: pyridine / Behandeln des Reaktionsprodukts mit wss. Natronlauge
2: 300 °C
View Scheme
daidzein 7-O-phosphate

daidzein 7-O-phosphate

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
With sulfatase VIII In water at 37℃; for 0.5h; pH=5.2;98%
6''-O-Acetyldaidzin

6''-O-Acetyldaidzin

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
diglycosidase, produced by Penicillium multicolor IAM7153 In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;96.2%
diglycosidase, produced by Aspergillus fumigatus IAM2046 In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;66.5%
β-glucosidase, derived from Aspergillus niger In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;9%
β-xylosidase, derived from pectinase G In methanol at 55℃; for 1h; pH=4; Enzyme kinetics; Aqueous acetate buffer;9.7%
β-glucosidase, derived from almond In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;0.6%
7-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one
1157-39-7

7-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
With hydrogen iodide for 4h; Reflux;94%
With aluminum (III) chloride In toluene at 100℃; for 12h; Sealed tube; Inert atmosphere;92%
With boron tribromide84%
With pyridine hydrochloride at 180℃; for 12h; Inert atmosphere;63%
With hydrogen iodide
7-benzyloxy-3-(4-methoxyphenyl)-1-benzopyran-4-one
1621-59-6

7-benzyloxy-3-(4-methoxyphenyl)-1-benzopyran-4-one

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
With aluminum (III) chloride; ethanethiol In dichloromethane at 0℃; for 0.5h; Inert atmosphere;92%
With aluminum (III) chloride; ethanethiol In dichloromethane at 0℃; for 0.5h; Inert atmosphere;92%
7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on
485-72-3

7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
Stage #1: 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on With boron tribromide In dichloromethane at 0 - 20℃; for 4h;
Stage #2: With water In dichloromethane at 0℃;
65%
With boron tribromide In dichloromethane at 0 - 20℃;65%
6''-O-malonyldaidzin
124590-31-4

6''-O-malonyldaidzin

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
diglycosidase, produced by Penicillium multicolor IAM7153 In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;61.5%
diglycosidase, produced by Aspergillus fumigatus IAM2046 In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;32.3%
β-glucosidase, derived from Aspergillus niger In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;16%
β-xylosidase, derived from pectinase G In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;3.3%
4-hydroxyphenylacetate
156-38-7

4-hydroxyphenylacetate

recorcinol
108-46-3

recorcinol

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
Stage #1: 4-hydroxyphenylacetate; recorcinol With zinc(II) chloride at 140℃; under 600.06 Torr; for 0.333333h;
Stage #2: With moroxydine; acetic acid; orthoformic acid triethyl ester In N,N-dimethyl-formamide at 140℃; for 5h; Temperature;
60%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

recorcinol
108-46-3

recorcinol

2-Hydroxyphenylacetic acid
614-75-5

2-Hydroxyphenylacetic acid

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
In ethanol; water; trifluoroborane diethyl ether; N,N-dimethyl-formamide44%
7-hydroxy-3-(4-aminophenyl)-4H-benzopyran-4-one
77316-78-0

7-hydroxy-3-(4-aminophenyl)-4H-benzopyran-4-one

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite ueber das Diazoniumsalz;
pratol
487-24-1

pratol

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
With hydrogen iodide
2-Carboxy-7,4'-dihydroxyisoflavone
57023-42-4

2-Carboxy-7,4'-dihydroxyisoflavone

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
at 300℃;
7,4'-dihydroxy-dihydroflavone
69097-97-8

7,4'-dihydroxy-dihydroflavone

A

daidzein
486-66-8

daidzein

B

(2R,3S)-2,7,4'-trihydroxyisoflavanone
131887-80-4

(2R,3S)-2,7,4'-trihydroxyisoflavanone

Conditions
ConditionsYield
With NADPH at 30℃; for 0.75h; Mechanism; cytochrome P-450; other substrates, effect of detergents;
1-(2,4-Dihydroxy-phenyl)-2-(4-hydroxy-phenyl)-3,3-dimethoxy-propan-1-one

1-(2,4-Dihydroxy-phenyl)-2-(4-hydroxy-phenyl)-3,3-dimethoxy-propan-1-one

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
With hydrogenchloride In methanol for 2h; Heating; Yield given;
Formic acid 3-(4-hydroxy-phenyl)-4-oxo-4H-chromen-7-yl ester

Formic acid 3-(4-hydroxy-phenyl)-4-oxo-4H-chromen-7-yl ester

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
With triethylamine; formyl acetic anhydride at 80 - 100℃; for 0.25h; Yield given;
daidzin
552-66-9

daidzin

A

D-Glucose
2280-44-6

D-Glucose

B

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
With hydrogenchloride
With citrate buffer; phosphate buffer; soybean β-glucosidase at 40℃; pH=5.0; Enzyme kinetics;
2,7,4'-trihydroxyisoflavanone
109963-62-4

2,7,4'-trihydroxyisoflavanone

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
2-hydroxyisoflavanone dehydratase In phosphate buffer; acetone at 30℃; for 0.333333h; pH=7.0; Dehydration;
2-hydroxyisoflavanone dehydratase In phosphate buffer; acetone at 30℃; for 0.333333h; pH=7.0; Enzyme kinetics; Dehydration;
2,4,4'-trihydroxy deoxybenzoin
17720-60-4

2,4,4'-trihydroxy deoxybenzoin

zinc cyanide

zinc cyanide

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
With diethyl ether Einleiten von Chlorwasserstoff und Erhitzen des Reaktionsprodukts mit Wasser;
Multi-step reaction with 2 steps
1: Et3N / 0.17 h / 0 °C
2: mixed anhydride of acetic and formic acid, Et3N / 0.25 h / 80 - 100 °C
View Scheme
2,4,4'-trihydroxy deoxybenzoin
17720-60-4

2,4,4'-trihydroxy deoxybenzoin

formic acid ethyl ester
109-94-4

formic acid ethyl ester

sodium

sodium

daidzein
486-66-8

daidzein

Conditions
ConditionsYield
Erhitzen des Reaktionsprodukts mit wss.-aethanol.HCl;
daidzein
486-66-8

daidzein

equol
531-95-3

equol

Conditions
ConditionsYield
With Eggerthella sp. YY7918 at 37℃; for 72h;100%
With 5%-palladium/activated carbon; hydrogen; acetic acid In ethanol; water at 20℃; under 760.051 Torr; for 10h;95%
daidzein
486-66-8

daidzein

3',4',7-trihydroxyisoflavone
485-63-2

3',4',7-trihydroxyisoflavone

Conditions
ConditionsYield
With bacillus megaterium tyrosinase In dimethyl sulfoxide at 20℃; for 6h; pH=9 - 10; Enzymatic reaction;100%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 50℃; for 2h;28%
With ferredoxin reductase; ferredoxin; recombinant CYP105D7 from Streptomyces avermitilis MA4680; NADH In aq. phosphate buffer at 20℃; for 2h; pH=7.2; Kinetics; Enzymatic reaction;
Multi-step reaction with 4 steps
1: potassium carbonate / acetone / 12 h / 60 °C
2: bromine / dichloromethane / 0.5 h / 20 °C
3: copper(I) bromide / methanol; N,N-dimethyl-formamide / 2 h / 20 - 120 °C / Darkness
4: dimethylsulfide; aluminum (III) chloride / dichloromethane / 6 h / 5 - 20 °C
View Scheme
daidzein
486-66-8

daidzein

3-(chloromethyl)-2-benzothiazolinone
73762-91-1

3-(chloromethyl)-2-benzothiazolinone

daidzein 7-N-(2
640275-93-0

daidzein 7-N-(2"(3"H)-benzothiazolonyl)methyl ether

Conditions
ConditionsYield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 14h;98.4%
daidzein
486-66-8

daidzein

acetic anhydride
108-24-7

acetic anhydride

daidzein diacetate
3682-01-7

daidzein diacetate

Conditions
ConditionsYield
Stage #1: daidzein; acetic anhydride at 60℃; for 0.166667h;
Stage #2: With pyridine at 60℃; for 0.0833333h;
98%
for 3h; Reflux;96.5%
With pyridine at 105 - 110℃; for 1h;90%
daidzein
486-66-8

daidzein

Hexanoyl chloride
142-61-0

Hexanoyl chloride

7,4'-di-O-hexanoyl-daidzein
602329-45-3

7,4'-di-O-hexanoyl-daidzein

Conditions
ConditionsYield
With dmap; triethylamine In N,N-dimethyl-formamide at 20℃; for 4.5h; Cooling with ice;95%
With pyridine; dmap In chloroform at -20℃;77%
daidzein
486-66-8

daidzein

allyl bromide
106-95-6

allyl bromide

7-allyloxy-3-(4-allyloxy-phenyl)-4H-chromen-4-one
102042-06-8

7-allyloxy-3-(4-allyloxy-phenyl)-4H-chromen-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone for 8h; Williamson-type O-alkylation reaction; Reflux;94%
daidzein
486-66-8

daidzein

7,4’-dihydroxy-3’-nitroisoflavone

7,4’-dihydroxy-3’-nitroisoflavone

Conditions
ConditionsYield
With ammonium nitrate; trifluoroacetic anhydride In acetonitrile at 20℃; for 1.5h;94%
With ammonium cerium (IV) nitrate; acetic acid In N,N-dimethyl-formamide at 20℃;92%
With sulfuric acid; nitric acid In ethanol at 20℃; for 2h;
daidzein
486-66-8

daidzein

(+/-)-4-Hydroxy-Equol

(+/-)-4-Hydroxy-Equol

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In N,N-dimethyl-formamide at 25℃; under 600.06 Torr; for 3h; Time;93%
With hydrogen; 10% Pd/Al2O3 In ethanol under 750.075 Torr;
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 40 °C
2: sodium tetrahydroborate; ethanol / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
3: palladium(II) hydroxide; ammonium formate / water; tetrahydrofuran; ethanol / Inert atmosphere
View Scheme
daidzein
486-66-8

daidzein

N-chloroethylpiperidine hydrochloride
2008-75-5

N-chloroethylpiperidine hydrochloride

7-(2-(piperidin-1-yl)ethoxy)-3-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-4H-chromen-4-one
41524-24-7

7-(2-(piperidin-1-yl)ethoxy)-3-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-4H-chromen-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone for 8h; Williamson-type O-alkylation reaction; Reflux;93%

486-66-8Relevant articles and documents

-

Kazakov et al.

, (1975)

-

P-450-DEPENDENT OXIDATIVE REARRANGEMENT IN ISOFLAVONE BIOSYNTHESIS: RECONSTITUTION OF P-450 AND NADPH:P-450 REDUCTASE

Hakamatsuka, Takashi,Hashim, Muhammed Faisal,Ebizuka, Yutaka,Sankawa, Ushio

, p. 5969 - 5978 (1991)

The reaction mechanism of oxidative rearrangement in the conversion of liquiritigenin, a flavanone, into 2,7,4'-trihydroxyisoflavanone was studied in elicitor-challenged Pueraria lobata cell cultures.The involvement of cytochrome P-450 in the reaction, hydroxylation associated with 1,2-aryl migration, was proved previously by the inhibition experiments with carbon monoxide and P-450 inhibitors.In order to obtain rigorous evidence proving that the enzyme is a P-450, a reconstitution experiment was performed with solubilized cytochrome P-450 and NADPH:cytochrome P-450 reductase fractions.During these studies we noticed that various biosynthetic reactions can be interpreted as P-450-mediated reactions associated with migration or bond cleavage.Ring contraction of 7-hydroxy-kaurenoic acid in gibberellin biosynthesis, the formation of a furan ring in furanocoumarin biosynthesis and several rearrangement reactions in steroid metabolism are discussed as examples of P-450 reactions associated with migration or bond cleavage.

Structure–activity relationship of phytoestrogen analogs as ERα/β agonists with neuroprotective activities

Cho, Hye Won,Gim, Hyo Jin,Li, Hua,Subedi, Lalita,Kim, Sun Yeou,Ryu, Jae-Ha,Jeon, Raok

, p. 99 - 105 (2021/01/06)

A set of isoflavononid and flavonoid analogs was prepared and evaluated for estrogen receptor α (ERα) and ERβ transactivation and anti-neuroinflammatory activities. Structure–activity relationship (SAR) study of naturally occurring phytoestrogens, their metabolites, and related isoflavone analogs revealed the importance of the C-ring of isoflavonoids for ER activity and selectivity. Docking study suggested putative binding modes of daidzein 2 and dehydroequol 8 in the active site of ERα and ERβ, and provided an understanding of the promising activity and selectivity of dehydroequol 8. Among the tested compounds, equol 7 and dehydroequol 8 were the most potent ERα/β agonists with ERβ selectivity and neuroprotective activity. This study provides knowledge on the SAR of isoflavonoids for further development of potent and selective ER agonists with neuroprotective potential.

Identification of ortho catechol-containing isoflavone as a privileged scaffold that directly prevents the aggregation of both amyloid β plaques and tau-mediated neurofibrillary tangles and its in vivo evaluation

Do, Ji Min,Gee, Min Sung,Inn, Kyung-Soo,Kim, Jong-Ho,Kim, Nam Kwon,Kim, Nam-Jung,Lee, Hyun Woo,Lee, Jong Kil,Seo, Min-Duk,Seong, Ji Hye,Son, Seung Hwan,Yoo, Hyung-Seok,Yoo, Ji-Na

, (2021/07/01)

In this study, polyhydroxyisoflavones that directly prevent the aggregation of both amyloid β (Aβ) and tau were expediently synthesized via divergent Pd(0)-catalyzed Suzuki-Miyaura coupling and then biologically evaluated. By preliminary structure–activity relationship studies using thioflavin T (ThT) assays, an ortho-catechol containing isoflavone scaffold was proven to be crucial for preventing both Aβ aggregation and tau-mediated neurofibrillary tangle formation. Additional TEM experiment confirmed that ortho-catechol containing isoflavone 4d significantly prevented the aggregation of both Aβ and tau. To investigate the mode of action (MOA) of 4d, which possesses an ortho-catechol moiety, 1H-15N HSQC NMR analysis was thoroughly performed and the result indicated that 4d could directly inhibit both the formation of Aβ42 fibrils and the formation of tau-derived neurofibrils, probably through the catechol-mediated nucleation of tau. Finally, 4d was demonstrated to alleviate cognitive impairment and pathologies related to Alzheimer's disease in a 5XFAD transgenic mouse model.

Transient and Recyclable Halogenation Coupling (TRHC) for Isoflavonoid Synthesis with Site-Selective Arylation

Wan, Jie-Ping,Tu, Zhi,Wang, Yuyun

supporting information, p. 6907 - 6910 (2019/05/10)

A transient and recyclable C?H iodination has been designed for the synthesis of isoflavonoids through the domino reactions of o-hydroxyphenyl enaminones and aryl boronic acids in the presence of catalytic KI and Pd catalyst. Instead of the conventional cross-coupling strategy employing pre-halogenated substrates, this method transforms raw C?H bond by means of a transient C?H halogenation to smoothly relay the subsequent C-arylation. Consequently, such a method avoids the pre-functionalization for C?halogen bond installation as well as the generation of stoichiometric halogen-containing waste following the cross-coupled product, disclosing an intriguing new coupling protocol to forge the C?C bond in the virgin area between classical C?X (X=halogen) bond cross coupling and the C?H activation.

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