Dihydrodaidzein | CAS:17238-05-0 | Manufacturer ChemFaces

Dihydrodaidzein

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Description:

Dihydrodaidzein-producing bacteria might lead to clarification of some of the mechanisms regulating the production of equol by fecal microbiota.

Targets:

P-gp

In vitro:

Biosci Microflora. 2011;30(3):65-71.

Dihydrodaidzein-producing Clostridium-like intestinal bacterium, strain TM-40, affects in vitro metabolism of daidzein by fecal microbiota of human male equol producer and non-producers.[Pubmed: 25045313]

Much attention has been focused on the biological effects of equol, a metabolite of daidzein produced by intestinal microbiota. However, little is known about the role of isoflavone metabolizing bacteria in the intestinal microbiota.
METHODS AND RESULTS:
Recently, we isolated a Dihydrodaidzein (DHD)-producing Clostridium-like bacterium, strain TM-40, from human feces. We investigated the effects of strain TM-40 on in vitro daidzein metabolism by human fecal microbiota from a male equol producer and two male equol non-producers. In the fecal suspension from the male equol non-producer and DHD producer, DHD was detected in the in vitro fecal incubation of daidzein after addition of TM-40. The DHD concentration increased as the concentration of strain TM-40 increased. In the fecal suspension from the equol producer, the fecal equol production was increased by the addition of strain TM-40. The occupation ratios of Bifidobacterium and Lactobacillales were higher in the equol non-producers than in the equol producer. Adding isoflavone-metabolizing bacteria to the fecal microbiota should facilitate the estimation of the metabolism of isoflavonoids by fecal microbiota.
CONCLUSIONS:
Studies on the interactions among equol-producing microbiota and DHD-producing bacteria might lead to clarification of some of the mechanisms regulating the production of equol by fecal microbiota.

Biosci Biotechnol Biochem. 2013;77(11):2210-7.

Transport mechanisms for soy isoflavones and microbial metabolites dihydrogenistein and dihydrodaidzein across monolayers and membranes.[Pubmed: 24200780]

Isoflavone data concerning the metabolism and permeability on intestinal epithelial cells are scarce, particularly for microbial isoflavone metabolites.
METHODS AND RESULTS:
This study evaluates the absorption mechanisms for the isoflavones, genistein and daidzein, and their microbial metabolites, dihydrogenistein (DHG) and Dihydrodaidzein (DHD). The permeability characteristics of isoflavones were compared by using the Caco-2 human colon adenocarcinoma cell line for a parallel artificial membrane permeability assay, and comparing their physicochemical properties.
CONCLUSIONS:
The data suggest that genistein, DHG and DHD were efficiently transported by passive diffusion according to the pH-partition hypothesis. Genistein was conjugated by phase II metabolizing enzymes and acted as a substrate of the breast cancer resistance protein (BCRP). Daidzein was not conjugated but did act as a substrate for BCRP, multidrug resistance-associated proteins, and P-glycoprotein. In contrast, DHG and DHD were markedly more permeable than their parent isoflavones; they were therefore difficult to transport by the efflux effect, and glucuronidation/sulfation was limited by the flux time.

Dihydrodaidzein Description

Source:	The seeds of Glycine max.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

More...

Cell. 2018 Jan 11;172(1-2):249-261.e12.
doi: 10.1016/j.cell.2017.12.019.
IF=36.216(2019)

PMID: 29328914

Cell Metab. 2020 Mar 3;31(3):534-548.e5.
doi: 10.1016/j.cmet.2020.01.002.
IF=22.415(2019)

PMID: 32004475

Mol Cell. 2017 Nov 16;68(4):673-685.e6.
doi: 10.1016/j.molcel.2017.10.022.
IF=14.548(2019)

PMID: 29149595

ACS Nano. 2018 Apr 24;12(4): 3385-3396.
doi: 10.1021/acsnano.7b08969.
IF=13.903(2019)

PMID: 29553709

Nature Plants. 2016 Dec 22;3: 16206.
doi: 10.1038/nplants.2016.205.
IF=13.297(2019)

PMID: 28005066

Sci Adv. 2018 Oct 24;4(10): eaat6994.
doi: 10.1126/sciadv.aat6994.
IF=12.804(2019)

PMID: 30417089

Kinase Assay:

Appl Environ Microbiol. 2005 Jan;71(1):214-9.

Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium.[Pubmed: 15640190]

A newly isolated rod-shaped, gram-negative anaerobic bacterium from human feces, named Julong 732, was found to be capable of metabolizing the isoflavone Dihydrodaidzein to S-equol under anaerobic conditions.
METHODS AND RESULTS:
The metabolite, equol, was identified by using electron impact ionization mass spectrometry, (1)H and (13)C nuclear magnetic resonance spectroscopy, and UV spectral analyses. However, strain Julong 732 was not able to produce equol from daidzein, and tetrahydrodaidzein and dehydroequol, which are most likely intermediates in the anaerobic metabolism of Dihydrodaidzein, were not detected in bacterial culture medium containing Dihydrodaidzein. Chiral stationary-phase high-performance liquid chromatography eluted only one metabolite, S-equol, which was produced from a bacterial culture containing a racemic mixture of Dihydrodaidzein. Strain Julong 732 did not show racemase activity to transform R-equol to S-equol and vice versa. Its full 16S rRNA gene sequence (1,429 bp) had 92.8% similarity to that of Eggerthella hongkongenis HKU10.
CONCLUSIONS:
This is the first report of a single bacterium capable of converting a racemic mixture of Dihydrodaidzein to enantiomeric pure S-equol.

CAS No.	17238-05-0	Price	$268 / 10mg
Catalog No.	CFN90686	Purity	>=98%
Molecular Weight	256.26	Type of Compound	Flavonoids
Formula	C₁₅H₁₂O₄	Physical Description	Powder
Download	COA MSDS SDF Manual	Similar structural	Comparison (Web) (SDF)

Product Name	Dihydrodaidzein
CAS No.:	17238-05-0
Catalog No.:	CFN90686
Molecular Formula:	C₁₅H₁₂O₄
Molecular Weight:	256.26 g/mol
Purity:	>=98%
Type of Compound:	Flavonoids
Physical Desc.:	Powder
Targets:	P-gp
Source:	The seeds of Glycine max.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Price:	$268 / 10mg
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Antioxidants Compound Library Flavonoids Compound Library P-gp Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	3.9023 mL	19.5114 mL	39.0229 mL	78.0457 mL	97.5572 mL
5 mM	0.7805 mL	3.9023 mL	7.8046 mL	15.6091 mL	19.5114 mL
10 mM	0.3902 mL	1.9511 mL	3.9023 mL	7.8046 mL	9.7557 mL
50 mM	0.078 mL	0.3902 mL	0.7805 mL	1.5609 mL	1.9511 mL
100 mM	0.039 mL	0.1951 mL	0.3902 mL	0.7805 mL	0.9756 mL

CFN96546	Erythrinin D	1616592-59-6	366.37	C₂₁H₁₈O₆
CFN96554	Isoficusin A	1914963-20-4	404.47	C₂₅H₂₄O₅
CFN93022	5-Methyl-7-methoxyisoflavone	82517-12-2	266.29	C₁₇H₁₄O₃
CFN95385	Violanone	52250-38-1	316.3	C₁₇H₁₆O₆
CFN95387	3'-O-Methylviolanone	56973-42-3	330.3	C₁₈H₁₈O₆
CFN90686	Dihydrodaidzein	17238-05-0	256.26	C₁₅H₁₂O₄
CFN98774	Daidzein	486-66-8	254.2	C₁₅H₁₀O₄
CFN99962	Formononetin	485-72-3	268.27	C₁₆H₁₂O₄
CFN95024	Isoformononetin	486-63-5	268.3	C₁₆H₁₂O₄
CFN90873	Daidzein dimethyl ether	1157-39-7	282.3	C₁₇H₁₄O₄