Nicotiflorin

Names

[ Name ]:
Nicotiflorin

[Synonym ]:
kaempferol-3-O-rutinoside
Nicotiflorin
Kaempferol 3-O-rutinose
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
4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranoside
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside
Nicotiflorine
4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-
kaempferol 3-O-rutinoside
NICOTIFLOROSIDE
Kaempferol 3-O-β-rutinoside
Kaempferol-3-rutinoside
kaempferol-3-rhamnoglucoside

Biological Activity

[Description]:

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

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Flavonoids

Research Areas >> Neurological Disease

[Target]

Antiglycation[1]

[In Vitro]

For primarily cultured neurons suffered 2 h hypoxia followed by 24 h reoxygenation, nicotiflorin significantly attenuates cell death and reduces LDH release. Morphological observation also directly confirms its protective effect on neuron[2]. 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 g/mL) 2 h after onset of hypoxia are 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[3].

[In Vivo]

At doses of 2.5, 5 and 10 mg/kg, nicotiflorin administered immediately after the onset of ischemia markedly reduces brain infarct volume and neurological deficits[2]. Nicotiflorin (2.5-10 mg/kg) administered after onset of ischemia markedly reduces brain infarct volume by 24.5-63.2% and neurological deficits[3].

[Cell Assay]

Cortical neurons are treated with nicotiflorin (25-100 mg/mL) just before hypoxia. Cell viability is determined using the MTT assay[2].

[Animal admin]

Rats[2] A neurological examination is performed on each rat 24 h after the onset of ischemia. Briefly, neurological scores (NS) are derived using a 10-point sliding scale. Rats are administered 2.5, 5, and 10 mg/kg nicotiflorin or vehicle immediately after occlusion. Each animal is examined for reduced resistance to lateral push (score, 4), open field circling (score, 3), and shoulder adduction (score, 2) or contralateral forelimb flexion (score, 1) when held by the tail and suspended approximately 0.5 m above the floor. Rats extending both forelimbs toward the floor and not showing any other signs of neurological impairment are scored 0[2].

[References]

[1]. Lal Shyaula S, et al. Synthesis and antiglycation activity of kaempferol-3-O-rutinoside (nicotiflorin). Med Chem. 2012 May;8(3):415-20.

[2]. Li R, et al. Neuroprotection of nicotiflorin in permanent focal cerebral ischemia and in neuronal cultures. Biol Pharm Bull. 2006 Sep;29(9):1868-72.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.76

[ Boiling Point ]:
941.7±65.0 °C at 760 mmHg

[ Melting Point ]:
181-186 ºC

[ Molecular Formula ]:
C₂₇H₃₀O₁₅

[ Molecular Weight ]:
594.518

[ Flash Point ]:
312.8±27.8 °C

[ Exact Mass ]:
594.158447

[ PSA ]:
249.20000

[ LogP ]:
1.96

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.744

[ Storage condition ]:
?20°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ Safety Phrases ]:
22-45

[ RIDADR ]:
NONH for all modes of transport