A flavonoid glycoside with diverse biological activities
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Engeletin

Item No. 34657

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3R)-3-[(6-deoxy-α-L-mannopyranosyl)oxy]-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
CAS Number
572-31-6
Synonyms
  • Dihydrokaempferol 3-O-α-L-rhamnopyranoside
  • (+)-(2R,3R)-Dihydrokaempferol 3-O-α-L-rhamnoside
  • Dihydrokaempferol 3-rhamnoside
Molecular Formula
C21H22O10
Formula Weight
434.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:4): 0.2 mg/mlEthanol: 25 mg/ml
λmax
216, 293 nm
SMILES
O=C([C@@H]([C@](C1=CC=C(C=C1)O)([H])OC2=CC(O)=C3)O[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)C)O)O)O)C2=C3O
InChi Code
InChI=1S/C21H22O10/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/h2-8,15,17-25,27-28H,1H3/t8-,15-,17+,18+,19+,20-,21-/m0/s1
InChi Key
VQUPQWGKORWZII-WDPYGAQVSA-N
Origin
Plant/Engelhardia roxburghiana
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $63

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    10 mg

    $105

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    25 mg

    $197

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    50 mg

    $363

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    Cayman Chemical
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    Product Description

    Engeletin is a flavonoid glycoside that has been found in S. glabra and has diverse biological activities.1,2,3 It scavenges ABTS (Item No. 27317) radicals in a cell-free assay (IC50 = 18.13 µg/ml).1 Engeletin (2 µg/ml) induces apoptosis in MCF-7 and MDA-MB-231 human breast cancer cells.2 It inhibits LPS-induced production of IL-1β, IL-6, and nitric oxide (NO) in RAW 264.7 cells when used at a concentration of 100 µM.1 Engeletin inhibits TNF-α-induced NF-κB activation and apoptosis in isolated rat chondrocytes, as well as reduces cartilage erosion and the loss of proteoglycan in the inflamed joints in a rat model of surgically induced osteoarthritis.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhao, X., Chen, R., Shi, Y., et al. Antioxidant and anti-inflammatory activities of six flavonoids from Smilax glabra Roxb. Molecules 25(22), 5295 (2020).

    2. Wu, L.-S., Wang, X.-J., Wang, H., et al. Cytotoxic polyphenols against breast tumor cell in Smilax china L. J. Ethnaopharmacol. 130(3), 460-464 (2010).

    3. Wang, H., Jiang, Z., Pang, Z., et al. Engeletin protects against TNF-α-induced apoptosis and reactive oxygen species generation in chondrocytes and alleviates osteoarthritis in vivo. J. Inflamm. Res. 14, 745-760 (2021).