NarcissosideCAS# 604-80-8 |
- Isorhamnetin 3-robinobioside
Catalog No.:BCN8693
CAS No.:53584-69-3
Quality Control & MSDS
3D structure
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| Cas No. | 604-80-8 | SDF | Download SDF |
| PubChem ID | 5481663 | Appearance | Yellow powder |
| Formula | C28H32O16 | M.Wt | 624.54 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Synonyms | Isorhamnetol 3-rutinoside; 3'-Methylquercetin 3-rutinoside; Narcissin; Narcissoside; Quercetin 3'-methyl ether 3-rutinoside; 3-Rutinosylisorhamnetin; 3,4',5,7-Tetrahydroxy 3'-methoxyflavone 3-rutinoside | ||
| Solubility | Soluble in DMSO and methan | ||
| Chemical Name | 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one | ||
| SMILES | CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)OC)O)O)O)O)O)O | ||
| Standard InChIKey | UIDGLYUNOUKLBM-GEBJFKNCSA-N | ||
| Standard InChI | InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-13(31)6-11(29)7-15(17)42-25(26)10-3-4-12(30)14(5-10)39-2/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16+,18-,19+,21+,22-,23+,24+,27+,28-/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. |
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| 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. |
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| 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. | ||
| Description | Narcissoside is a good 15-LO and α-glucosidase inhibitor, it with synergism of B.flavum flavonoid and rutin, could be responsible for stronger protection against mitochondrial induced oxidative stress. |
| Targets | AMPK | α-Glucosidase | 15-lipoxygenase |
| In vitro | Flavonoid profiles of three Bupleurum species and in vitro hepatoprotective of activity Bupleurum flavum Forsk.[Pubmed: 25709205]Pharmacogn Mag. 2015 Jan-Mar;11(41):14-23.Bupleurum L. (Aspiaceae) species are used as herbal remedy in Chinese traditional medicine. OBJECTIVE: The aim was to investigate the flavonoids in three annual European Bupleurum species, including B. baldense, B. affine and B. flavum, and to test their antioxidant and possible hepatoprotective effects. |
| Kinase Assay | α-Glucosidase inhibition, 15-lipoxygenase inhibition, and brine shrimp toxicity of extracts and isolated compounds from Terminalia macroptera leaves.[Pubmed: 24635511]Pharm Biol. 2014 Sep;52(9):1166-9.Terminalia macroptera Guill. & Perr. (Combretaceae), a tree that grows in West Africa, has been used in traditional medicine against a variety of diseases such as hepatitis, gonorrhea, skin diseases, and diabetes. To investigate enzyme inhibitory activity against α-glucosidase and 15-lipoxygenase (15-LO) and toxicity against brine shrimp of extracts and compounds from T. macroptera leaves. |
| Structure Identification | J Sep Sci. 2014 Apr;37(8):957-65.Extraction and isolation of flavonoid glycosides from Flos Sophorae Immaturus using ultrasonic-assisted extraction followed by high-speed countercurrent chromatography.[Pubmed: 24515421]
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Narcissoside Dilution Calculator
Narcissoside Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.6012 mL | 8.0059 mL | 16.0118 mL | 32.0236 mL | 40.0295 mL |
| 5 mM | 0.3202 mL | 1.6012 mL | 3.2024 mL | 6.4047 mL | 8.0059 mL |
| 10 mM | 0.1601 mL | 0.8006 mL | 1.6012 mL | 3.2024 mL | 4.0029 mL |
| 50 mM | 0.032 mL | 0.1601 mL | 0.3202 mL | 0.6405 mL | 0.8006 mL |
| 100 mM | 0.016 mL | 0.0801 mL | 0.1601 mL | 0.3202 mL | 0.4003 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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Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activity.[Pubmed:15844957]
J Nat Prod. 2005 Apr;68(4):592-5.
Purification of a n-BuOH-soluble partition of the MeOH extract of Morinda citrifolia (Noni) fruits led to the isolation of two new iridoid glucosides, 6alpha-hydroxyadoxoside (1) and 6beta,7beta-epoxy-8-epi-splendoside (2), as well as 17 known compounds, americanin A (3), Narcissoside (4), asperuloside, asperulosidic acid, borreriagenin, citrifolinin B epimer a, citrifolinin B epimer b, cytidine, deacetylasperuloside, dehydromethoxygaertneroside, epi-dihydrocornin, d-glucose, d-mannitol, methyl alpha-d-fructofuranoside, methyl beta-d-fructofuranoside, nicotifloroside, and beta-sitosterol 3-O-beta-d-glucopyranoside. The structures of the new compounds were determined by spectroscopic data interpretation. Compound 4, borreriagenin, cytidine, deacetylasperuloside, dehydromethoxygaertneroside, epi-dihydrocornin, methyl alpha-d-fructofuranoside, and methyl beta-d-fructofuranoside were isolated for the first time from M. citrifolia. The antioxidant activity was evaluated for all isolates in terms of both DPPH and ONOO(-) bioassays. The neolignan, americanin A (3), was found to be a potent antioxidant in these assays.
Extraction and isolation of flavonoid glycosides from Flos Sophorae Immaturus using ultrasonic-assisted extraction followed by high-speed countercurrent chromatography.[Pubmed:24515421]
J Sep Sci. 2014 Apr;37(8):957-65.
A method of ultrasonic-assisted extraction followed by high-speed countercurrent chromatography was established for the extraction and isolation of three flavonoid glycosides, i.e. rutin, narcissin, and nicotiflorin from Flos Sophorae Immaturus. The effects of ultrasonic-assisted extraction factors for the main flavonoid compound (rutin) from Flos Sophorae Immaturus were optimized using Box-Behnken design combined with response surface methodology. The optimum conditions were determined as ultrasonic power 83% (600 W), solvent-to-material ratio 56:1, methanol concentration 82% v/v, and extraction time 60 min. Three bioactive flavonol glucosides, rutin, narcissin, and nicotiflorin were isolated from Flos Sophorae Immaturus using high-speed countercurrent chromatography. The separation was performed with a two-phase solvent system containing ethyl acetate/n-butanol/methanol/water (4:0.9:0.2:5, v/v). Amounts of 87 mg of rutin, 10.8 mg of narcissin, and 1.8 mg of nicotiflorin were isolated from 302 mg of crude extract of Flos Sophorae Immaturus in a one-step separation within 160 min with purities of 99.3, 98.0, and 95.1%, respectively, as determined by HPLC with diode array detection. Their structures were characterized by UV, MS, and NMR spectroscopy. It was demonstrated that the established method was simple, fast, and convenient, which was feasible to extract and isolate active flavonoid glycosides from Flos Sophorae Immaturus.
Flavonoid profiles of three Bupleurum species and in vitro hepatoprotective of activity Bupleurum flavum Forsk.[Pubmed:25709205]
Pharmacogn Mag. 2015 Jan-Mar;11(41):14-23.
BACKGROUND: Bupleurum L. (Aspiaceae) species are used as herbal remedy in Chinese traditional medicine. OBJECTIVE: The aim was to investigate the flavonoids in three annual European Bupleurum species, including B. baldense, B. affine and B. flavum, and to test their antioxidant and possible hepatoprotective effects. MATERIALS AND METHODS: Flavonoids from the methanol-aqueous extracts were quantified by solid-phase extraction-high-performance liquid chromatography. Bupleurum extracts (1-220 mg/ml) were tested for their antioxidant activity in DPPH and ABTS assays, as well as on isolated liver rat microsomes. In vitro hepatoprotective activity of B. flavum flavonoid (BFF) mixture and rutin, and narcissin, isolated from the same mixture, were evaluated on carbon tetrachloride (CCl4) and tert-butyl hydroperoxide (t-BuOOH) toxicity models in isolated rat hepatocytes. RESULTS: Narcissin was the dominant flavonol glycoside in B. flavum being present at 24.21 +/- 0.19 mg/g, whilst the highest content of rutin (28.63 +/- 1.57 mg/g) was found in B. baldense. B. flavum possessed the strongest DPPH (IC50 22.12 mug/ml) and ABTS (IC50 118.15 mug/ml) activity. At a concentration 1 mg/ml of BFF (rutin 197.58 mg/g, narcissin 75.74 mg/g), a stronger antioxidant effect in microsomes was evidenced in comparison with silymarin, rutin and narcissin. The hepatoprotective effect of BFF significantly reduced the elevated levels of lactate dehydrogenase and malondialdehyde, and ameliorated glutathione, being most active in t-BuOOH-induced injury model when compared with CCl4 toxicity (P < 0.001). CONCLUSION: In BFF, synergism of rutin and narcissin could be responsible for stronger protection against mitochondrial induced oxidative stress.
alpha-Glucosidase inhibition, 15-lipoxygenase inhibition, and brine shrimp toxicity of extracts and isolated compounds from Terminalia macroptera leaves.[Pubmed:24635511]
Pharm Biol. 2014 Sep;52(9):1166-9.
CONTEXT: Terminalia macroptera Guill. & Perr. (Combretaceae), a tree that grows in West Africa, has been used in traditional medicine against a variety of diseases such as hepatitis, gonorrhea, skin diseases, and diabetes. OBJECTIVE: To investigate enzyme inhibitory activity against alpha-glucosidase and 15-lipoxygenase (15-LO) and toxicity against brine shrimp of extracts and compounds from T. macroptera leaves. MATERIALS AND METHODS: Methanol extract, ethyl acetate, and butanol extracts obtained from the methanol extract, six isolated polyphenols (chebulagic acid, chebulic acid trimethyl ester, corilagin, methyl gallate, narcissin, and rutin), and shikimic acid were evaluated for enzyme inhibition and toxicity. RESULTS: In enzyme inhibition assays, all extracts showed high or very high activity. Chebulagic acid showed an IC50 value of 0.05 microM towards alpha-glucosidase and 24.9 +/- 0.4 microM towards 15-LO, in contrast to positive controls (acarbose: IC50 201 +/- 28 microM towards alpha-glucosidase, quercetin: 93 +/- 3 microM towards 15-LO). Corilagin and narcissin were good 15-LO and alpha-glucosidase inhibitors, as well, while shikimic acid, methyl gallate, and chebulic acid trimethyl ester were less active or inactive. Rutin was a good alpha-glucosidase inhibitor (IC50 ca. 3 microM), but less active towards 15-LO. None of the extracts or the isolated compounds seemed to be very toxic in the brine shrimp assay compared with the positive control podophyllotoxin. CONCLUSION: Inhibition of alpha-glucosidase in the gastrointestinal tract may be a rationale for the medicinal use of T. macroptera leaves against diabetes in traditional medicine in Mali. The plant extracts and its constituents show strong inhibition of the peroxidative enzyme 15-LO.
