A flavonoid
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Nicotiflorin

Item No. 27392

Technical Information
Formal Name
3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
CAS Number
17650-84-9
Synonyms
  • Kaempferol 3-O-β-rutinoside
  • 3,4′,5,7-Tetrahydroxyflavone 3-rhamnoglucoside
Molecular Formula
C27H30O15
Formula Weight
Purity
≥98%
A solid
DMF: 3mg/mLDMSO: 5mg/mLDMSO:PBS (pH 7.2) (1:5): 0.5mg/mL
λmax
267, 349 nm
SMILES
O=C(C(O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O2)O1)=C(C3=CC=C(O)C=C3)O4)C5=C4C=C(O)C=C5O
InChi Code
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
InChi Key
RTATXGUCZHCSNG-QHWHWDPRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Nicotiflorin is a flavonoid that has been found in I. glandulifera and has antioxidant and neuroprotective activities. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) and ABTS (Item No. 27317) radicals with EC50 values of 0.52 and 0.48 mg/ml, respectively, in cell-free assays.1 Nicotiflorin (1 µM) prevents hydrogen peroxide-induced decreases in tyrosine hydroxylase activity in PC12 cells and cell death in primary rat mesencephalic neurons.2 It decreases infarct volume by 24.5, 45.8, and 63.2% when administered at doses of 2.5, 5, and 10 mg/kg, respectively, in a rat model of cerebral ischemia-reperfusion injury induced by transient middle central artery occlusion (MCAO).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Szewczyk, K., Sezai Cicek, S., Zidorn, C., et alPhenolic constituents of the aerial parts of Impatiens glandulifera Royle (Balsaminaceae) and their antioxidant activities. Nat. Prod. Res. 33(19), 2851-2855 (2019).

    2. Qu, W., Fan, L., Kim, Y.C., et alKaempferol derivatives prevent oxidative stress-induced cell death in a DJ-1-dependent manner. J. Pharmacol. Sci. 110(2), 191-200 (2009).

    3. Li, R., Guo, M., Zhang, G., et alNicotiflorin reduces cerebral ischemic damage and upregulates endothelial nitric oxide synthase in primarily cultured rat cerebral blood vessel endothelial cells. J. Ethnopharmacol. 107(1), 143-150 (2006).