Alpinumisoflavone | CAS:34086-50-5 | Manufacturer ChemFaces

Alpinumisoflavone

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Description:

Alpinumisoflavone has atheroprotective effects, may result from their ability to upregulate mechanisms promoting HDL-cholesterol and bile acid formation, it is endowed with estrogenic properties accounting, at least in part, for E. lysistemon effects. Alpinumisoflavone induces cell death, may be via repressing both the ERK/MAPK and NF-κB pathways. Alpinumisoflavone is active against both Gram-negative and Gram-positive bacteria, the minimum inhibitory concentration values obtained (MIC) ranged from 3.9 ug/mL to 125 ug/mL.

Targets:

MEK | ERK | MAPK | NO | NF-kB | LDL | Antifection

In vitro:

Phytother Res. 2011 Jan;25(1):46-8.

Antibacterial activity of flavonoids from the stem bark of Erythrina caffra thunb.[Pubmed: 20623615 ]

The antibacterial activity of the stem bark of Erythrina caffra Thunb. was investigated against different bacterial strains.
METHODS AND RESULTS:
The antibacterial activity was determined by a micro broth dilution assay. Antibacterial compounds were isolated and identified using a Bruker Avance III LPO NMR spectrometer. Four known flavonoids, abyssione-V 4'-O-methyl ether, 6,8-diprenylgenistein, Alpinumisoflavone and burttinone, were isolated.
CONCLUSIONS:
All the compounds were active against both Gram-negative and Gram-positive bacteria. The minimum inhibitory concentration values obtained (MIC) ranged from 3.9 μg/mL to 125 μg/mL. This is the first report of antibacterial activity of burttinone and the isolation of these compounds from E. caffra.

In vivo:

Phytother Res. 2012 Jul;26(7):1029-36.

Effects of alpinumisoflavone and abyssinone V-4'-methyl ether derived from Erythrina lysistemon (Fabaceae) on the genital tract of ovariectomized female Wistar rat.[Pubmed: 22183714]

Erythrina lysistemon is an African medicinal plant used as a palliative for problems in women. The crude extract of this plant was shown to exhibit estrogenic effects on the female rat reproductive tract and on cell cuture.
METHODS AND RESULTS:
Using classic chromatographic methods, two compounds have been isolated as major constituents of this extract: Alpinumisoflavone (1) and abyssinone V-4'-methyl ether (2). To determine whether both compounds are actives principles accounting for E. lysistemon effects, we applied the classic 3-day uterotrophic assay. We also carried out a ligand binding assay to determine whether the observed effects are estrogen receptor (ER) mediated. This study showed that whereas compound 1 displayed a fourfold preference for ERα, compound 2 bound ERα and ERβ with a same affinity. The in vivo study showed that compound 1 increased the uterine wet weight by 182.23% (p < 0.01) and 71.79% (p < 0.05) at doses of 0.1 and 1 mg/kg BW/day respectively. The uterine epithelium thickened dose-dependently. Vaginal epithelial height also increased by 369.97 and 226.76% respectively (p < 0.01). Compound 2 acted only on the vagina and increased vaginal epithelial height by 244.56% (p < 0.01) at 1 mg/kg BW/day.
CONCLUSIONS:
These results suggest that compounds 1 and 2 are endowed with estrogenic properties accounting, at least in part, for E. lysistemon effects.

Alpinumisoflavone Description

Source:	The herbs of Genista pichisermolliana
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.

Kinase Assay:

J Pharm Pharmacol. 2015 Jul;67(7):990-6.

Alpinumisoflavone and abyssinone V 4'-methylether derived from Erythrina lysistemon (Fabaceae) promote HDL-cholesterol synthesis and prevent cholesterol gallstone formation in ovariectomized rats.[Pubmed: 25683903]

Erythrina lysistemon was found to improve lipid profile in ovariectomized rats. Alpinumisoflavone (AIF) and abyssinone V 4'-methylether (AME) derived from this plant induced analogous effects on lipid profile and decreased atherogenic risks. To highlight the molecular mechanism of action of these natural products, we evaluated their effects on the expression of some estrogen-sensitive genes associated with cholesterol synthesis (Esr1 and Apoa1) and cholesterol clearance (Ldlr, Scarb1 and Cyp7a1).
METHODS AND RESULTS:
Ovariectomized rats were subcutaneously treated for three consecutive days with either compound at the daily dose of 0.1, 1 and 10 mg/kg body weight (BW). Animals were sacrificed thereafter and their liver was collected. The mRNA of genes of interest was analysed by quantitative real-time polymerase chain reaction. Both compounds downregulated the mRNA expression of Esr1, a gene associated with cholesterogenesis and cholesterol gallstone formation. AME leaned the Apoa1/Scarb1 balance in favour of Apoa1, an effect promoting high-density lipoprotein (HDL)-cholesterol formation. It also upregulated the mRNA expression of Ldlr at 1 mg/kg/BW per day (25%) and 10 mg/kg/BW per day (133.17%), an effect favouring the clearance of low-density lipoprotein (LDL)-cholesterol. Both compounds may also promote the conversion of cholesterol into bile acids as they upregulated Cyp7a1 mRNA expression.
CONCLUSIONS:
AIF and AME atheroprotective effects may result from their ability to upregulate mechanisms promoting HDL-cholesterol and bile acid formation.

Animal Research:

Biol Pharm Bull. 2011;34(2):203-8.

Alpinumisoflavone induces apoptosis and suppresses extracellular signal-regulated kinases/mitogen activated protein kinase and nuclear factor-κB pathways in lung tumor cells.[Pubmed: 21415528 ]

Structure Identification:

Acta Crystallogr Sect E Struct Rep Online. 2008 Mar 14;64(Pt 4):o713.

Alpinumisoflavone.[Pubmed: 21202104 ]

METHODS AND RESULTS:
Alpinumisoflavone, C(20)H(16)O(5), {systematic name: 5-hydr-oxy-7-(4-hydroxy-phen-yl)-2,2-dimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one}, was obtained by demethyl-ation of the biologically active related compound, 4-O-methyl-alpinum-iso-flavone. The mol-ecular structure of Alpinumisoflavone is characterized by a fused tricyclic system that contains an approximately planar benzopyrone ring fragment. The six membered pyran ring adopts a half-chair conformation. Both ring systems show an out-of-plane twist. The dihedral angle between the mean plane of the benzopyrone system and the benzene ring is 54.29 (3)°. The mol-ecules are linked by O-H⋯O hydrogen bonds, forming a mol-ecular tape running along the b axis.

Product Name	Alpinumisoflavone
Price:
CAS No.:	34086-50-5
Catalog No.:	CFN98440
Molecular Formula:	C₂₀H₁₆O₅
Molecular Weight:	336.3 g/mol
Purity:	>=98%
Type of Compound:	Flavonoids
Physical Desc.:	Powder
Source:	The herbs of Genista pichisermolliana
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Antibacterial Compound Library Anti-hyperlipidemic Compound Library Anti-Atherosclerotic Compound Library Estrogenic effect Compound Library Flavonoids Compound Library NO Inhibitor Library NF-kB Inhibitor Library MEK Inhibitor Library MAPK Inhibitor Library LDL Inhibitor Library ERK Inhibitor Library Antifection Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.9735 mL	14.8677 mL	29.7354 mL	59.4707 mL	74.3384 mL
5 mM	0.5947 mL	2.9735 mL	5.9471 mL	11.8941 mL	14.8677 mL
10 mM	0.2974 mL	1.4868 mL	2.9735 mL	5.9471 mL	7.4338 mL
50 mM	0.0595 mL	0.2974 mL	0.5947 mL	1.1894 mL	1.4868 mL
100 mM	0.0297 mL	0.1487 mL	0.2974 mL	0.5947 mL	0.7434 mL

CFN97097	Dihydroalpinumisoflavone	63807-90-9	338.4	C₂₀H₁₈O₅
CFN92231	Erythrinin A	63807-86-3	320.3	C₂₀H₁₆O₄
CFN98440	Alpinumisoflavone	34086-50-5	336.3	C₂₀H₁₆O₅
CFN96499	Alpinumisoflavone acetate	86989-18-6	378.38	C₂₂H₁₈O₆
CFN98098	Erysubin B	221150-19-2	352.3	C₂₀H₁₆O₆
CFN97916	Warangalone	4449-55-2	404.5	C₂₅H₂₄O₅
CFN98062	2',4',5'-Trimethoxy-2'',2''-dimethylpyrano[5'',6'':6,7]isoflavone	211799-56-3	394.4	C₂₃H₂₂O₆