A flavonoid glycoside with diverse biological activities
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Isomer(s)
36467Myricetin 3-galactoside
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Gossypin

Item No. 34142

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(3,4-dihydroxyphenyl)-8-(β-D-glucopyranosyloxy)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
CAS Number
652-78-8
Synonyms
  • Gossypetin-8-O-glucoside
Molecular Formula
C21H20O13
Formula Weight
480.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:2): 0.3 mg/mlDMSO: 25 mg/ml
λmax
262, 382 nm
SMILES
O=C(C(O)=C(C1=CC(O)=C(C=C1)O)O2)C(C2=C3O[C@@H]4O[C@@H]([C@H]([C@@H]([C@H]4O)O)O)CO)=C(C=C3O)O
InChi Code
InChI=1S/C21H20O13/c22-5-11-13(27)15(29)17(31)21(32-11)34-19-10(26)4-9(25)12-14(28)16(30)18(33-20(12)19)6-1-2-7(23)8(24)3-6/h1-4,11,13,15,17,21-27,29-31H,5H2/t11-,13-,15+,17-,21+/m1/s1
InChi Key
SJRXVLUZMMDCNG-KKPQBLLMSA-N
Origin
Plant/Hibiscus vitifolius
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $41

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    50 mg

    $108

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    100 mg

    $196

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    250 mg

    $389

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    Product Description

    Gossypin is a flavonoid glycoside originally isolated from H. vitifolius that has diverse biological activities.1,2,3,4,5 It inhibits RANKL-induced osteoclastogenesis in RAW 264.7 cells when used at a concentration of 5 µM.1 Gossypin inhibits Aurora B kinase (IC50 = 11.07 µM in a cell-free assay using the human enzyme), as well as Aurora A kinase and p90 ribosomal S6 kinase 2 (RSK2) at 20 µM.2,3 It induces cell cycle arrest at the G2/M phase and apoptosis in HGC-27 gastric cancer cells.3 Gossypin decreases lactate dehydrogenase (LDH) release induced by the glutathione-depleting agent D,L-buthionine (S,R)-sulfoximine (Item No. 23691) in primary rat cortical cells (IC50 = 7.4 µg/ml).4 It reduces acetic acid-induced writhing in mice, an effect that can be reversed by the opioid antagonist naloxone, in a dose-dependent manner.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kunnumakkara, A.B., Nair, A.S., Ahn, K.S., et al. Gossypin, a pentahydroxy glucosyl flavone, inhibits the transforming growth factor beta-activated kinase-1-mediated NF-κB activation pathway, leading to potentiation of apoptosis, suppression of invasion, and abrogation of osteoclastogenesis. Blood 109(12), 5112-5121 (2007).

    2. Jung, Y., Shin, S.Y., Yong, Y., et al. Plant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationships. Chem. Biol. Drug Des. 85(5), 574-585 (2015).

    3. Wang, L., Wang, X., Chen, H., et al. Gossypin inhibits gastric cancer growth by direct targeting of AURKA and RSK2. Phytother. Res. 33(3), 640-650 (2019).

    4. Yoon, I., Lee, K.H., and Cho, J. Gossypin protects primary cultured rat cortical cells from oxidative stress- and beta-amyloid-induced toxicity. Arch. Pharm. Res. 27(4), 454-459 (2004).

    5. Viswanathan, S., Sambantham, P.T., Reddy, K., et al. Gossypin-induced analgesia in mice. Eur. J. Pharmacol. 98(2), 289-291 (1984).