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Dihydrokaempferide

CAS# 137225-59-3

Dihydrokaempferide

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Chemical structure

Dihydrokaempferide

3D structure

Chemical Properties of Dihydrokaempferide

Cas No. 137225-59-3 SDF Download SDF
PubChem ID 21721857 Appearance Powder
Formula C16H14O6 M.Wt 302.3
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Aromadendrin 4'-methyl ether
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2R,3R)-3,5,7-trihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
SMILES COC1=CC=C(C=C1)C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O
Standard InChIKey CKDYDMSDCNQHEB-JKSUJKDBSA-N
Standard InChI InChI=1S/C16H14O6/c1-21-10-4-2-8(3-5-10)16-15(20)14(19)13-11(18)6-9(17)7-12(13)22-16/h2-7,15-18,20H,1H3/t15-,16+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Dihydrokaempferide Dilution Calculator

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Dihydrokaempferide Molarity Calculator

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Preparing Stock Solutions of Dihydrokaempferide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.308 mL 16.5399 mL 33.0797 mL 66.1594 mL 82.6993 mL
5 mM 0.6616 mL 3.308 mL 6.6159 mL 13.2319 mL 16.5399 mL
10 mM 0.3308 mL 1.654 mL 3.308 mL 6.6159 mL 8.2699 mL
50 mM 0.0662 mL 0.3308 mL 0.6616 mL 1.3232 mL 1.654 mL
100 mM 0.0331 mL 0.1654 mL 0.3308 mL 0.6616 mL 0.827 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Dihydrokaempferide

Kaempferide Enhances Chemosensitivity of Human Lung Adenocarcinoma A549 Cells Mediated by the Decrease in Phosphorylation of Akt and Claudin-2 Expression.[Pubmed:32340376]

Nutrients. 2020 Apr 23;12(4). pii: nu12041190.

Claudins (CLDNs) play crucial roles in the formation of tight junctions. We have reported that abnormal expression of CLDN2 confers chemoresistance in the spheroids of human lung adenocarcinoma A549 cells. A food composition, which can reduce CLDN2 expression, may function to prevent the malignant progression. Here, we found that ethanol extract of Brazilian green propolis (EBGP) and kaempferide, a major component of EBGP, decrease CLDN2 expression. In the two-dimensional culture model, EBGP decreased the tight junctional localization of CLDN2 without affecting that of zonula occludens-1, an adaptor protein, and enhanced paracellular permeability to doxorubicin, a cytotoxic anticancer drug. EBGP reduced hypoxic stress, and enhanced the accumulation and sensitivity of doxorubicin in the spheroid of A549 cells. Kaempferide dose-dependently decreased CLDN2 expression, although Dihydrokaempferide and pinocembrin did not. The phosphorylation of Akt, a regulatory factor of CLDN2 expression, was inhibited by kaempferide but not by Dihydrokaempferide. The 2,3-double bond in the C ring may be important to inhibit Akt. Kaempferide decreased the mRNA level and promoter activity of CLDN2, indicating that it inhibits the transcription of CLDN2. In accordance with EBGP, kaempferide decreased the tight junctional localization of CLDN2 and increased a paracellular permeability to doxorubicin, suggesting that it diminished the paracellular barrier to small molecules. In addition, kaempferide reduced hypoxic stress, and enhanced the accumulation and sensitivity of doxorubicin in the spheroids. In contrast, Dihydrokaempferide did not improve the sensitivity to doxorubicin. Further study is needed using an animal model, but we suggest that natural foods abundantly containing kaempferide are candidates for the prevention of the chemoresistance of lung adenocarcinoma.

Isolation, Identification, and Synthesis of a New Prenylated Cinnamic Acid Derivative from Brazilian Green Propolis and Simultaneous Quantification of Bioactive Components by LC-MS/MS.[Pubmed:31597041]

J Agric Food Chem. 2019 Nov 6;67(44):12303-12312.

A new cinnamic acid derivative, (E)-3-[4-hydroxy-3-((E)-3-formyl-2-butenyl)phenyl]-2- propenoic acid (20) has been isolated from the ethanol extract of Brazilian green propolis along with three known cinnamic acid derivatives, 3,4-dihydroxy-5-prenyl-(E)-cinnamic acid (4), capillartemisin A (6), and 2,2-dimethylchromene-6-(E)-propenoic acid (8), and a flavonoid, Dihydrokaempferide (16) by liquid-liquid participation, a series of column chromatography and preparative HPLC. Their structures have been determined by spectroscopic analyses and chemical synthesis of compound 20. The simultaneous quantification of 20 constituents, including 10 cinnamic acid derivatives, 7 flavonoids, and 3 caffeoylquinic acid derivatives, has also been developed and validated using LC-MS/MS. The new compound 20 was shown to activate PPAR alpha but not PPAR beta or gamma.

Putative identification of new p-coumaroyl glycoside flavonoids in grape by ultra-high performance liquid chromatography/high-resolution mass spectrometry.[Pubmed:26406348]

Rapid Commun Mass Spectrom. 2015 Feb 28;29(4):357-66.

RATIONALE: Grape polyphenols are antioxidant compounds, markers in vine chemotaxonomy, and involved in color stabilization of red wines. Sugar acylation usually confers higher stability on glycoside derivatives and this effect is enhanced by an aromatic substituent such as p-coumaric acid. Until now, only p-coumaroyl anthocyanins have been found in grape. METHODS: A method of 'suspect screening analysis' by ultra-high-performance liquid chromatography/high-resolution mass spectrometry (UHPLC/QTOFMS) has recently been developed to study grape metabolomics. In the present study, this approach was used to identify new polyphenols in grape by accurate mass measurement, MS/MS fragmentation, and study of correlations between fragments observed and putative structures. RESULTS: Three putative p-coumaroyl flavonoids were identified in Raboso Piave grape extract: a Dihydrokaempferide-3-O-p-coumaroylhexoside-like flavanone, isorhamnetin-3-O-p-coumaroylglucoside, and a chrysoeriol-p-coumaroylhexoside-like flavone. Accurate MS provided structural characterization of functional groups, and literature data indicates their probable position in the molecule. A fragmentation scheme is proposed for each compound. CONCLUSIONS: Compounds were identified by overlapping various analytical methods according to recommendations in the MS-based metabolomics literature. Stereochemistry and the definitive position of substituents in the molecule can only be confirmed by isolation and characterization or synthesis of each compound. These findings suggest addressing research of acylated polyphenol glycosides to other grape varieties.

LC-MS-based metabolite profiling of methanolic extracts from the medicinal and aromatic species Mentha pulegium and Origanum majorana.[Pubmed:25982347]

Phytochem Anal. 2015 Sep-Oct;26(5):320-30.

INTRODUCTION: There has been increasing interest dedicated to the phenolic compounds with a view to their antioxidant and healthy properties. Recent studies have focused on plants from the Lamiaceae family with special interest in phenolic compounds antioxidant potential. OBJECTIVE: The metabolite profile of methanolic extracts from two Lamiacea medicinal plants was investigated. MATERIALS AND METHODS: Mentha pulegium and Origanum majorana methanolic extracts were analysed using reversed-phase ultra-high-performance liquid chromatography (RP-UHPLC) coupled to electrospray ionisation quadrupole time-of-flight mass spectrometry (ESI-QTOF-MS) detection in the negative ion mode. RESULTS: A total of 85 metabolites were characterised from different families, such as organic acids and derivatives, amino acids and derivatives, nucleosides, phenolic compounds as well as other polar metabolites, by using the MS and MS/MS information provided by the QTOF-MS. However, the total phenols and flavonoids were also quantified spectrophotometrically and they registered higher amounts in Mentha pulegium than in Origanum majorana extract. Gallocatechin was the major compound in M. pulegium extract whereas quercetin dimethyl ether, jaceidin and Dihydrokaempferide were the major ones in O. majorana extract. CONCLUSION: The distribution of phenolic compounds in the methanolic extract showed a variation among studied plants. Mentha pulegium can be considered as a source of gallocatechin.

Effects of an ethanol extract of Brazilian green propolis on human cytochrome P450 enzyme activities in vitro.[Pubmed:25361167]

J Agric Food Chem. 2014 Nov 19;62(46):11296-302.

Supplement-drug interaction on CYP enzyme activity is occasionally found to cause clinically adverse events, and no report on interactions of propolis is available either in vitro or clinical. In this study, we tried to estimate the risk of an interaction between an ethanol extract of Brazilian green propolis (EEP-B55) and drugs in vitro and in vivo. The activities of CYP1A2, CYP2C9, CYP2C19, CYP2D6, and CYP3A4 were attenuated by EEP-B55 in a concentration-dependent manner, and artepillin C, kaempferide, Dihydrokaempferide, isosakuranetin, and kaempferol were estimated to have potential for CYP inhibition. The IC50 values of artepillin C for each CYP were approximately 33-fold higher than its Cmax in the blood of rats after dosing with 5-fold the recommended daily intake of EEP-B55. These findings suggest that liver CYP enzyme activities are not markedly affected by artepillin C at the recommended daily intake of EEP-B55.

Antihypertensive effects of flavonoids isolated from brazilian green propolis in spontaneously hypertensive rats.[Pubmed:19571393]

Biol Pharm Bull. 2009 Jul;32(7):1244-50.

Propolis, a honeybee product, has become popular as a food and alternative medicine. Its constituents have been shown to exert pharmacological effects, such as anticancer, antimicrobial, and anti-inflammatory effects. The present study was performed to investigate whether Brazilian green propolis exerts antihypertensive effects in spontaneously hypertensive rats (SHR) and which constituents are involved in its effects. Brazilian green propolis was extracted with ethanol and subjected to LH-20 column chromatography eluted with ethanol. The ethanol-eluted fractions at 10 mg/kg were administered orally to SHR for 14 d. Significant decreases in blood pressure were observed in fractions 6 and 7. The active constituents were purified and identified to be four flavonoids: Dihydrokaempferide and isosakuranetin in fraction 6 and betuletol and kaempferide in fraction 7. These flavonoids at 10 mg/kg were administered orally to SHR for 28 d, and as a result, isosakuranetin, Dihydrokaempferide and betuletol produced significant decrease in blood pressure, especially marked were the effects observed in the group that received isosakuranetin. Brazilian green propolis, fractions 6 and 7, and the 4 active constituents relaxed isolated SHR aorta in a concentration-dependent manner. Therefore, these finding suggest that the vasodilating action may be partly involved in the mechanism of antihypertensive effect. Hence, the ethanol extract of Brazilian green propolis and its main constituents may be useful for prevention of hypertension.

[Studies on flavonoids of Eupatorium odoratum L].[Pubmed:17918432]

Zhong Yao Cai. 2007 Jun;30(6):657-60.

OBJECTIVE: To investigate the flavonoid constituents from aerial parts of Eupatorium odoratum L. systematically. METHODS: The constituents of the EtoAc-soluble portions of the 95% ethanol extraction were isolated and purified by silica gel and sephadex LH-20 chromatography. Their structures were elucidated on the basis of physicochemical properties and spectral analysis. RESULTS: Eight compounds were isolated and identified as kaempferol-3-methoxy (I), rhamnetin (II), tamarixetin (III), quercetin (IV), kaempferol (V), apigenin (VI), luteolin (VII), Dihydrokaempferide (VIII). CONCLUSION: Compound I , II and VI were isolated for the first time from genus Eupatorium, and VIII which is rare flavonoid was obtainted for the first time from family Compositae.

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