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Noroxyhydrastinine

CAS# 21796-14-5

Noroxyhydrastinine

Catalog No. BCN2646----Order now to get a substantial discount!

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Quality Control of Noroxyhydrastinine

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Chemical structure

Noroxyhydrastinine

3D structure

Chemical Properties of Noroxyhydrastinine

Cas No. 21796-14-5 SDF Download SDF
PubChem ID 89047 Appearance Powder
Formula C10H9NO3 M.Wt 191.19
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 7,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquinolin-5-one
SMILES C1CNC(=O)C2=CC3=C(C=C21)OCO3
Standard InChIKey VSOJKDUWYQCWFM-UHFFFAOYSA-N
Standard InChI InChI=1S/C10H9NO3/c12-10-7-4-9-8(13-5-14-9)3-6(7)1-2-11-10/h3-4H,1-2,5H2,(H,11,12)
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.

Source of Noroxyhydrastinine

The herbs of Thalictrum foliolosum DC.

Biological Activity of Noroxyhydrastinine

DescriptionNoroxyhydrastinine exhibits potent melanogenesis-inhibitory activities, it inhibits melanogenesis, at least in part, by inhibiting the expression of protein levels of tyrosinase, TRP-1, and TRP-2 in α-MSH-stimulated B16 melanoma cells.
TargetsTyrosinase | TRP-1 | TRP-2
In vitro

Alkaloids from Zuojin Formula and their cytotoxicities against proliferation of cancer cells[Reference: WebLink]

《Chinese Traditional and Herbal Drugs》 2014-01

To study the alkaloid constituents of Zuojin Formula, consisting of Coptidis Rhizoma and Euodiae Fructus, and to evaluate their cytotoxicities against the proliferation of cancer cells in human digestive tract.
METHODS AND RESULTS:
The constituents were isolated and purified by column chromatography on silica gel and Sephadex LH-20, as well as the chemical structures of alkaloids were determined by physicochemical properties and spectral data analyses. The cytotoxicities assay against human gastric NCI-N87 and colon adenocarcinoma Caco-2 cell lines was carried out by MTT method. Fifteen alkaloids were obtained from the normal butanol soluble fraction of 70% ethanolic extract in Zuojin Formula and identified as rutaecarpine(1), evodiamine(2), rhetsinine(3), coptisine(4), wuchuyuamide III(5), 8-trichloromethyl-7, 8-dihydropalmatine(6), epiberberine(7), 8-trichloromethyl-7, 8-dihydroepiberberine(8), 8-trichloromethyl-7, 8-dihydrocoptisine(9), palmatine(10), berberine(11), 1, 2, 3, 4-tetrahydro-1-oxo-β-carboline(12), Noroxyhydrastinine(13), 8-oxo-epiberberine(14), and corydaldine(15). Compounds 1, 2, 4, and 11 showed the inhibitory activities against the proliferation of NCI-N87 and Caco-2 cell with the half inhibitory concentration of 12.61—91.18 μmol/L.
CONCLUSIONS:
Compound 8 is a new compound. Compounds 1, 2, 4, and 11 may be the main effective components in Zuojin Formula against the proliferation of cancer cells in human digestive tract.

Melanogenesis-Inhibitory and Cytotoxic Activities of Limonoids, Alkaloids, and Phenolic Compounds from Phellodendron amurense Bark.[Pubmed: 28425165]

Chem Biodivers. 2017 Jul;14(7).

Four limonoids, 1 - 4, five alkaloids, 5 - 9, and four phenolic compounds, 10 - 13, were isolated from a MeOH extract of the bark of Phellodendron amurense (Rutaceae). Among these, compound 13 was new, and its structure was established as rel-(1R,2R,3R)-5-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-1-(methoxycarbonylmethyl)indane-2-carboxylic acid methyl ester (γ-di(methyl ferulate)) based on the spectrometric analysis.
METHODS AND RESULTS:
Upon evaluation of compounds 1 - 13 against the melanogenesis in the B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), four compounds, limonin (1), Noroxyhydrastinine (6), haplopine (7), and 4-methoxy-1-methylquinolin-2(1H)-one (8), exhibited potent melanogenesis-inhibitory activities with almost no toxicity to the cells. Western blot analysis revealed that compound 6 inhibited melanogenesis, at least in part, by inhibiting the expression of protein levels of tyrosinase, TRP-1, and TRP-2 in α-MSH-stimulated B16 melanoma cells. In addition, when compounds 1 - 13 were evaluated for their cytotoxic activities against leukemia (HL60), lung (A549), duodenum (AZ521), and breast (SK-BR-3) cancer cell lines, five compounds, berberine (5), 8, canthin-6-one (9), α-di-(methyl ferulate) (12), and 13, exhibited cytotoxicities against one or more cancer cell lines with IC50 values in the range of 2.6 - 90.0 μm. In particular, compound 5 exhibited strong cytotoxicity against AZ521 (IC50 2.6 μm) which was superior to that of the reference cisplatin (IC50 9.5 μm).

Protocol of Noroxyhydrastinine

Structure Identification
Chemical & pharmaceutical bulletin 30(8), 2793-2796, 1982-08-25

Chemical Transformation of Protoberberines. I. Conversion of Tetrahydroberberine and Dihydroberberine into Noroxyhydrastinine by Photooxygenation[Reference: WebLink]

Simple and biomimetic conversions of tetrahydroberberine (1) and dihydroberberine (6) into Noroxyhydrastinine (3), an isoquinolone alkaloid, are described. Photooxygenation of 1 afforded berberal (2), 3,and O-methylpseudopianic acid (4). The same products were obtained more efficiently by photooxygenation of 6.

Zhong Yao Cai. 2008 Nov;31(11):1656-8.

Studies on chemical constituents in the anti-myocardial ischemia effective fraction of Corydalis yanhusuo.[Pubmed: 19260272]

To study the chemical constituents in the anti-myocardial ischemia effective fraction of Corydalis yanhusuo.
METHODS AND RESULTS:
Compounds were isolated and purified by a macroporous resin, Sephadex LH-20, ODS column chromatography, and prepared TLC. Their structures were identified by spectral analysis and chemical evidence. Nine compounds, tetrahydrocolumbamine (1), Noroxyhydrastinine (2), corunine (3), dehydrocorydaline (4), dehydrocorybulbine (5), columbamine (6), coptisine (7), berberine (8), palmatine (9) were isolated and identified from the effective fraction of Corydalis yanhusuo.
CONCLUSIONS:
Compounds 2, 3 and 5 were isolated from this plant for the first time.

Noroxyhydrastinine Dilution Calculator

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Noroxyhydrastinine Molarity Calculator

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Preparing Stock Solutions of Noroxyhydrastinine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.2304 mL 26.152 mL 52.304 mL 104.608 mL 130.76 mL
5 mM 1.0461 mL 5.2304 mL 10.4608 mL 20.9216 mL 26.152 mL
10 mM 0.523 mL 2.6152 mL 5.2304 mL 10.4608 mL 13.076 mL
50 mM 0.1046 mL 0.523 mL 1.0461 mL 2.0922 mL 2.6152 mL
100 mM 0.0523 mL 0.2615 mL 0.523 mL 1.0461 mL 1.3076 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 Noroxyhydrastinine

Melanogenesis-Inhibitory and Cytotoxic Activities of Limonoids, Alkaloids, and Phenolic Compounds from Phellodendron amurense Bark.[Pubmed:28425165]

Chem Biodivers. 2017 Jul;14(7).

Four limonoids, 1 - 4, five alkaloids, 5 - 9, and four phenolic compounds, 10 - 13, were isolated from a MeOH extract of the bark of Phellodendron amurense (Rutaceae). Among these, compound 13 was new, and its structure was established as rel-(1R,2R,3R)-5-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-1-(methoxycarbon ylmethyl)indane-2-carboxylic acid methyl ester (gamma-di(methyl ferulate)) based on the spectrometric analysis. Upon evaluation of compounds 1 - 13 against the melanogenesis in the B16 melanoma cells induced with alpha-melanocyte-stimulating hormone (alpha-MSH), four compounds, limonin (1), Noroxyhydrastinine (6), haplopine (7), and 4-methoxy-1-methylquinolin-2(1H)-one (8), exhibited potent melanogenesis-inhibitory activities with almost no toxicity to the cells. Western blot analysis revealed that compound 6 inhibited melanogenesis, at least in part, by inhibiting the expression of protein levels of tyrosinase, TRP-1, and TRP-2 in alpha-MSH-stimulated B16 melanoma cells. In addition, when compounds 1 - 13 were evaluated for their cytotoxic activities against leukemia (HL60), lung (A549), duodenum (AZ521), and breast (SK-BR-3) cancer cell lines, five compounds, berberine (5), 8, canthin-6-one (9), alpha-di-(methyl ferulate) (12), and 13, exhibited cytotoxicities against one or more cancer cell lines with IC50 values in the range of 2.6 - 90.0 mum. In particular, compound 5 exhibited strong cytotoxicity against AZ521 (IC50 2.6 mum) which was superior to that of the reference cisplatin (IC50 9.5 mum).

[Studies on chemical constituents in the anti-myocardial ischemia effective fraction of Corydalis yanhusuo].[Pubmed:19260272]

Zhong Yao Cai. 2008 Nov;31(11):1656-8.

OBJECTIVE: To study the chemical constituents in the anti-myocardial ischemia effective fraction of Corydalis yanhusuo. METHODS: Compounds were isolated and purified by a macroporous resin, Sephadex LH-20, ODS column chromatography, and prepared TLC. Their structures were identified by spectral analysis and chemical evidence. RESULTS: Nine compounds, tetrahydrocolumbamine (1), Noroxyhydrastinine (2), corunine (3), dehydrocorydaline (4), dehydrocorybulbine (5), columbamine (6), coptisine (7), berberine (8), palmatine (9) were isolated and identified from the effective fraction of Corydalis yanhusuo. CONCLUSION: Compounds 2, 3 and 5 were isolated from this plant for the first time.

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