A polyphenolic glycoside flavone with diverse biological activities
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Afzelin

Item No. 31135

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[(6-deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
CAS Number
482-39-3
Synonyms
  • Kaempferin
  • Kaempferol 3-O-rhamnoside
  • Kaempferol 3-O-α-L-rhamnopyranoside
Molecular Formula
C21H20O10
Formula Weight
432.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: soluble
SMILES
OC1=C2C(OC(C3=CC=C(O)C=C3)=C(O[C@H]4[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O4)C2=O)=CC(O)=C1
InChi Code
InChI=1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/t8-,15-,17+,18+,21-/m0/s1
InChi Key
SOSLMHZOJATCCP-AEIZVZFYSA-N
Origin
Plant/Cyclocarya paliurus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $66

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    5 mg

    $182

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    10 mg

    $297

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    25 mg

    $578

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    Cayman Chemical
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    Product Description

    Afzelin is a polyphenolic glycoside flavone that has been found in B. pinnatum and has diverse biological activities.1,2,3 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals with an IC50 value of 6.44 μg/ml.1 Afzelin is active against S. aureus, P. aeruginosa, S. typhi, C. albicans, C. parapsilosis, and C. neoformans (MICs = 8, 16, 2, 16, 4, and 4 μg/ml, respectively). It inhibits the proliferation of A549, SKOV3, and SK-MEL-2 cells (EC50s = 40.6, 34.5, and 33.9 μg/ml, respectively).2 Afzelin (26 mg/kg per day) reduces the number of eosinophils, other inflammatory cells, and total cells, as well as the levels of IL-4, IL-5, and IL-13, in bronchoalveolar lavage fluid (BALF) in a mouse model of allergic asthma.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tatsimo, S.J.N., Tamokou, J.d.D., Havyarimana, L., et al. Antimicrobial and antioxidant activity of kaempferol rhamnoside derivatives from Bryophyllum pinnatum. BMC Res. Notes 5, 158 (2012).

    2. Kim, Y.-K., Kim, Y.S., Choi, S.U., et al. Isolation of flavonol rhamnosides from Loranthus tanakae and cytotoxic effect of them on human tumor cell lines. Arch. Pharm. Res. 27(1), 44-47 (2004).

    3. Chung, M.J., Pandey, R.P., Choi, J.W., et al. Inhibitory effects of kaempferol-3-O-rhamnoside on ovalbumin-induced lung inflammation in a mouse model of allergic asthma. Int. Immunopharmacol. 25(2), 302-310 (2015).