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Nicotiflorin CAS NO.17650-84-9

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  • Nicotiflorin
  • 17650-84-9
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Quick Details

  • ProName: Nicotiflorin
  • CasNo: 17650-84-9
  • Molecular Formula: C27H30O15= 594.5
  • Appearance: detailed see specifications
  • Application: analysis,activity test,Botanical Refer...
  • DeliveryTime: 1-3?working?days?after?confirming?the?...
  • PackAge: According to the clients requirement.
  • Port: China main port
  • ProductionCapacity: 1 Metric Ton/Day
  • Purity: ≥98%
  • Storage: Store at 2~8°C
  • Transportation: by air or by ocean shipping
  • LimitNum: 10 Milligram
  • Plant of Origin: Chinese herbal medicine
  • Testing Method: NMR/MS/HPLC
  • Product Ecification: 1mg-1kg
  • Heavy Metal: <10ppm
  • Voluntary Standards: company standard
  • Storage: Store in dry, dark and ventilated plac...
  • PackAge: Brown vial HDPE plastic bottle

Superiority

Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine,Traditional Chinese Medicine), Natural Active Pharmaceutical Ingredients worldwide. From small quantities for R&D or reference standard, to large quantities for customizing or manufacturing, Biopurify emphasizes on consistent and reliable services for his customers. 
With excellent quality products and good service, we have clients from more than dozens countries and regions, and we pride ourselves in providing our customers with a total satisfaction experiences.
We are doing our best to be your reliable partner for high quality Phytochemicals and Reference Standards from china.
 
Our main services:
A. Supply active ingredients and reference standards ofTraditional Chinese Medicine, from mgs to kgs scale.
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR, CM and PD services from lab scale, pilot scale to commercial scale(GMP is also available)
E.Traditional Chinese Medicine compounds library
 

1.Provide traditional Chinese medicine reference materials and natural active ingredients;
2.More than 2200 compounds are available for selection, continuously building high-quality natural product libraries for drug research and development;
3.Provide various screening libraries and more inhibitor products;
4.Provide separation and structural determination of natural products;
5.Laboratory scale pilot to commercial scale collaborative research and process development services.More than 180 experiences in phytochemistry (still increasing)
Each product has passed very strict testing (NMR/MS/HPLC)
Agents from many countries

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.

Details

Chemical Properties of Nicotiflorin

Cas No. 17650-84-9    
PubChem ID 5318767 Appearance Yellow powder
Formula C27H30O15 M.Wt 594.5
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Nicotifiorin; Nicotiflorin; Nicotifloroside; 3,4',5,7-Tetrahydroxyflavone 3-rutinoside
Solubility DMSO : 100 mg/mL (168.20 mM; Need ultrasonic)
Chemical Name 5,7-dihydroxy-2-(4-hydroxyphenyl)-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)O)O)O)O)O)O
Standard InChIKey RTATXGUCZHCSNG-QHWHWDPRSA-N
Standard InChI InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-12(29)7-14(16)40-24(25)10-2-4-11(28)5-3-10/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,23+,26+,27-/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.

Source of Nicotiflorin

1 Cucurbita sp. 2 Geranium sp. 3 Glycyrrhiza sp. 4 Heterotheca sp. 5 Larrea sp. 6 Lycium sp. 7 Quercus sp. 8 Ruscus sp. 9 Sambucus sp. 10 Solidago sp.

Biological Activity of Nicotiflorin

Description Nicotiflorin shows potent antiglycation activity and neuroprotection effects, it has protective effects on cerebral ischemic damage, reducing memory dysfunction, energy metabolism failure and oxidative stress in multi-infarct dementia model rats.
Targets NOS | ATPase | Calcium Channel | Potassium Channel
In vitro

Nicotiflorin, rutin and chlorogenic acid: phenylpropanoids involved differently in quantitative resistance of potato tubers to biotrophic and necrotrophic pathogens.[Pubmed: 22677447]

Plant Physiol Biochem. 2012 Aug;57:23-31.

Physiological and molecular mechanisms underlying quantitative resistance of plants to pathogens are still poorly understood, but could depend upon differences in the intensity or timing of general defense responses.
METHODS AND RESULTS:
This may be the case for the biosynthesis of phenolics which are known to increase after elicitation by pathogens. We thus tested the hypothesis that differences in quantitative resistance were related to differential induction of phenolics by pathogen-derived elicitors. Five potato cultivars (Solanum tuberosum, L.) spanning a range of quantitative resistance were treated with a concentrated culture filtrate (CCF) of Phytophthora infestans or purified lipopolysaccharides (LPS) from Pectobacterium atrosepticum. The kinetic of phenolics accumulation was followed and a set of typical phenolics was identified: chlorogenic acid, phenolamides and flavonols including rutin (quercetin-3-O-rutinoside) and Nicotiflorin (kaempferol-3-O-rutinoside). Our results showed that CCF but not LPS induced differential accumulation of major phenolics among cultivars. Total phenolics were related with resistance to P. atrosepticum but not to P. infestans. However, Nicotiflorin was inversely related with resistance to both pathogens. Rutin, but not Nicotiflorin, inhibited pathogen growth in vitro at physiological concentrations.
CONCLUSIONS:
These data therefore suggest that (i) several phenolics are candidate markers for quantitative resistance in potato, (ii) some of these are pathogen specific although they are produced by a general defense pathway, (iii) resistance marker molecules do not necessarily have antimicrobial activity, and (iv) the final content of these target molecules-either constitutive or induced-is a better predictor of resistance than their inducibility by pathogen elicitors.

In vivo

Protective effects of Nicotiflorin on reducing memory dysfunction, energy metabolism failure and oxidative stress in multi-infarct dementia model rats.[Pubmed: 17448528]

Pharmacol Biochem Behav. 2007 Apr;86(4):741-8.

The present study aimed to determine whether Nicotiflorin, a natural flavonoid extracted from coronal of Carthamus tinctorius, has a protective effect on cerebral multi-infarct dementia in rats.
METHODS AND RESULTS:
The multi-infarct dementia model rats were prepared by injecting man-made micro-thrombi into the right hemisphere. The administration groups were treated once daily with 30, 60 and 120 mg/kg Nicotiflorin (i.g.) from 5 days before ischemia operation to 3 days after the operation for biochemical examination, 10 days for Morris water maze study and morphological observations and 20 days for eight-arm radial maze task. 2,3,5-triphenyltetrazolium chloride (TTC) staining showed that infarct volume of each Nicotiflorin administration group was much smaller than that of vehicle-treated multi-infarct dementia group, and hematoxylin and eosin (HE) staining showed that histopathological abnormalities of each Nicotiflorin group were also much lighter than that of vehicle-treated multi-infarct dementia group. Each Nicotiflorin group showed much better spatial memory performance in Morris water maze tests and eight-arm radial maze task compared with the vehicle-treated multi-infarct dementia group, significantly attenuated the elevation of lactic acid and malondialdehyde (MDA) contents and the decrease in lactate dehydrogenase (LDH), Na(+)K(+)ATPase, Ca(2+)Mg(2+)ATPase and superoxide dismutase (SOD) activity in the brain tissue which was composed of striatum, cortex and hippocampus of the ischemia hemisphere at day 3 after ischemia operation.
CONCLUSIONS:
These results suggest that Nicotiflorin has protective effects on reducing memory dysfunction, energy metabolism failure and oxidative stress in multi-infarct dementia model rats.

Protocol of Nicotiflorin

Cell Research

Nicotiflorin reduces cerebral ischemic damage and upregulates endothelial nitric oxide synthase in primarily cultured rat cerebral blood vessel endothelial cells.[Pubmed: 16806761]

J Ethnopharmacol. 2006 Aug 11;107(1):143-50.

Nicotiflorin is a flavonoid glycoside extracted from a traditional Chinese medicine Flos Carthami.
METHODS AND RESULTS:
In the current study, we investigated the neuroprotective effect of Nicotiflorin on a transient focal cerebral ischemia-reperfusion model in rats. Nicotiflorin (2.5-10 mg/kg) administered after onset of ischemia markedly reduced brain infarct volume by 24.5-63.2% and neurological deficits. Also the effect of Nicotiflorin on endothelial nitric oxide synthase (eNOS) activity, mRNA and protein expression after hypoxia-reoxygenation (H-R) treatment was investigated in an in vitro model mimic cerebrum ischemia-reperfusion in vivo. After total 4 h hypoxia and 12 h reoxygenation, eNOS activity, mRNA and protein levels in the primarily cultured rat cerebral blood vessel endothelial cells treated with Nicotiflorin (25-100 microg/ml) 2 h after onset of hypoxia were significantly higher than eNOS activity, mRNA and protein levels in the pure H-R cells and also higher than eNOS activity, mRNA and protein levels in cells cultured under normoxic conditions. The results demonstrated that Nicotiflorin had a protective effect against cerebral ischemic damage.
CONCLUSIONS:
The results also gave an important elucidation for the mechanism underlying the protective effect at the cellular level.

Structure Identification

Med Chem. 2012 May;8(3):415-20.

Synthesis and antiglycation activity of kaempferol-3-O-rutinoside (nicotiflorin).[Pubmed: 22530897]


METHODS AND RESULTS:
Kaempferol-3-O-α-L-rhamanopyranosyl-(1'''-6'')-β-D-glucopyranoside (1) (Nicotiflorin or kaempferol-3-O-rutinoside), isolated from the aerial parts of Osyris wightiana Wall. ex Wight, exhibited a potent antiglycation activity in vitro. A short and efficient route to kaempferol-3-O-rutinoside (1) is also described in this paper. To study the structure-activity relationship, few other derivatives of kaempferol were also evaluated for their antiglycation activity. Moreover the cytotoxicity analysis was also performed for these compounds.
CONCLUSIONS:
The Structure-Activity Relationship (SAR) studies showed that sugar derivatives of kaempferol possess a promising antiglycation activity.

Preparing Stock Solutions of Nicotiflorin

  1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.6821 mL 8.4104 mL 16.8209 mL 33.6417 mL 42.0521 mL
5 mM 0.3364 mL 1.6821 mL 3.3642 mL 6.7283 mL 8.4104 mL
10 mM 0.1682 mL 0.841 mL 1.6821 mL 3.3642 mL 4.2052 mL
50 mM 0.0336 mL 0.1682 mL 0.3364 mL 0.6728 mL 0.841 mL
100 mM 0.0168 mL 0.0841 mL 0.1682 mL 0.3364 mL 0.4205 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.

 

References on Nicotiflorin

Protective effects of Nicotiflorin on reducing memory dysfunction, energy metabolism failure and oxidative stress in multi-infarct dementia model rats.[Pubmed:17448528]

Pharmacol Biochem Behav. 2007 Apr;86(4):741-8.

The present study aimed to determine whether Nicotiflorin, a natural flavonoid extracted from coronal of Carthamus tinctorius, has a protective effect on cerebral multi-infarct dementia in rats. The multi-infarct dementia model rats were prepared by injecting man-made micro-thrombi into the right hemisphere. The administration groups were treated once daily with 30, 60 and 120 mg/kg Nicotiflorin (i.g.) from 5 days before ischemia operation to 3 days after the operation for biochemical examination, 10 days for Morris water maze study and morphological observations and 20 days for eight-arm radial maze task. 2,3,5-triphenyltetrazolium chloride (TTC) staining showed that infarct volume of each Nicotiflorin administration group was much smaller than that of vehicle-treated multi-infarct dementia group, and hematoxylin and eosin (HE) staining showed that histopathological abnormalities of each Nicotiflorin group were also much lighter than that of vehicle-treated multi-infarct dementia group. Each Nicotiflorin group showed much better spatial memory performance in Morris water maze tests and eight-arm radial maze task compared with the vehicle-treated multi-infarct dementia group, significantly attenuated the elevation of lactic acid and malondialdehyde (MDA) contents and the decrease in lactate dehydrogenase (LDH), Na(+)K(+)ATPase, Ca(2+)Mg(2+)ATPase and superoxide dismutase (SOD) activity in the brain tissue which was composed of striatum, cortex and hippocampus of the ischemia hemisphere at day 3 after ischemia operation. These results suggest that Nicotiflorin has protective effects on reducing memory dysfunction, energy metabolism failure and oxidative stress in multi-infarct dementia model rats.

Isolation and characterization of nicotiflorin obtained by enzymatic hydrolysis of two precursors in tea seed extract.[Pubmed:20225859]

J Agric Food Chem. 2010 Apr 28;58(8):4808-13.

Two flavonol triglycosides, camelliaside A (CamA) and camelliaside B (CamB), of tea seed extract (TSE) were subjected to enzymatic hydrolysis. Among five kinds of glycosidases investigated, beta-galactosidase (Gal) induced selective hydrolysis of CamA. On the other hand, pectinase (Pec) and cellulase (Cel) induced hydrolysis of CamB. For Gal and Pec, only kaempferol diglycoside (Nicotiflorin, NF) was produced; on the other hand, significant amounts of kaempferol monoglycoside (astragalin, AS) and kaempferol (KR) were also detected for Cel. The combination of the use of Gal and Pec in the enzymatic hydrolysis of TSE afforded NF with high specificity. Crude NF with 22% purity was recovered from the enzymatic reaction mixture by extraction with organic solvent, and pure NF with >95% purity was obtained by crystallized in water. The chemical structure of NF was confirmed by (1)H and (13)C NMR analyses.

Nicotiflorin, rutin and chlorogenic acid: phenylpropanoids involved differently in quantitative resistance of potato tubers to biotrophic and necrotrophic pathogens.[Pubmed:22677447]

Plant Physiol Biochem. 2012 Aug;57:23-31.

Physiological and molecular mechanisms underlying quantitative resistance of plants to pathogens are still poorly understood, but could depend upon differences in the intensity or timing of general defense responses. This may be the case for the biosynthesis of phenolics which are known to increase after elicitation by pathogens. We thus tested the hypothesis that differences in quantitative resistance were related to differential induction of phenolics by pathogen-derived elicitors. Five potato cultivars (Solanum tuberosum, L.) spanning a range of quantitative resistance were treated with a concentrated culture filtrate (CCF) of Phytophthora infestans or purified lipopolysaccharides (LPS) from Pectobacterium atrosepticum. The kinetic of phenolics accumulation was followed and a set of typical phenolics was identified: chlorogenic acid, phenolamides and flavonols including rutin (quercetin-3-O-rutinoside) and Nicotiflorin (kaempferol-3-O-rutinoside). Our results showed that CCF but not LPS induced differential accumulation of major phenolics among cultivars. Total phenolics were related with resistance to P. atrosepticum but not to P. infestans. However, Nicotiflorin was inversely related with resistance to both pathogens. Rutin, but not Nicotiflorin, inhibited pathogen growth in vitro at physiological concentrations. These data therefore suggest that (i) several phenolics are candidate markers for quantitative resistance in potato, (ii) some of these are pathogen specific although they are produced by a general defense pathway, (iii) resistance marker molecules do not necessarily have antimicrobial activity, and (iv) the final content of these target molecules-either constitutive or induced-is a better predictor of resistance than their inducibility by pathogen elicitors.

Nicotiflorin reduces cerebral ischemic damage and upregulates endothelial nitric oxide synthase in primarily cultured rat cerebral blood vessel endothelial cells.[Pubmed:16806761]

J Ethnopharmacol. 2006 Aug 11;107(1):143-50.

Nicotiflorin is a flavonoid glycoside extracted from a traditional Chinese medicine Flos Carthami. In the current study, we investigated the neuroprotective effect of Nicotiflorin on a transient focal cerebral ischemia-reperfusion model in rats. Nicotiflorin (2.5-10 mg/kg) administered after onset of ischemia markedly reduced brain infarct volume by 24.5-63.2% and neurological deficits. Also the effect of Nicotiflorin on endothelial nitric oxide synthase (eNOS) activity, mRNA and protein expression after hypoxia-reoxygenation (H-R) treatment was investigated in an in vitro model mimic cerebrum ischemia-reperfusion in vivo. After total 4 h hypoxia and 12 h reoxygenation, eNOS activity, mRNA and protein levels in the primarily cultured rat cerebral blood vessel endothelial cells treated with Nicotiflorin (25-100 microg/ml) 2 h after onset of hypoxia were significantly higher than eNOS activity, mRNA and protein levels in the pure H-R cells and also higher than eNOS activity, mRNA and protein levels in cells cultured under normoxic conditions. The results demonstrated that Nicotiflorin had a protective effect against cerebral ischemic damage. The results also gave an important elucidation for the mechanism underlying the protective effect at the cellular level.

Description

Nicotiflorin is a flavonoid glycoside extracted from a traditional Chinese medicine Flos Carthami. Nicotiflorin shows potent antiglycation activity and neuroprotection effects.

Keywords:

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