An iridoid glucoside with diverse biological activities
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Isomer(s)
28281Geniposide
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Verbenalin

Item No. 34663

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,4aS,7S,7aR)-1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-methyl-5-oxo-cyclopenta[c]pyran-4-carboxylic acid, methyl ester
CAS Number
548-37-8
Synonyms
  • Cornin
  • NSC 118055
Molecular Formula
C17H24O10
Formula Weight
388.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
236 nm
SMILES
COC(C1=CO[C@H]([C@@]2([H])[C@]1([H])C(C[C@@H]2C)=O)O[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO)=O
InChi Code
InChI=1S/C17H24O10/c1-6-3-8(19)11-7(15(23)24-2)5-25-16(10(6)11)27-17-14(22)13(21)12(20)9(4-18)26-17/h5-6,9-14,16-18,20-22H,3-4H2,1-2H3/t6-,9+,10+,11-,12+,13-,14+,16-,17-/m0/s1
InChi Key
HLXRWTJXGMHOFN-XJSNKYLASA-N
Origin
Plant/Cornus officinalis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $110

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    10 mg

    $203

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    25 mg

    $462

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    Product Description

    Verbenalin is an iridoid glucoside that has been found in V. officinalis and has diverse biological activities.1,2,3 It inhibits the activities of COX-1 and COX-2 by 37 and 48%, respectively, when used at a concentration of 258 µM.2 Verbenalin (129 µM) inhibits proliferation of AGS gastric, SF-268 CNS, HCT116 colon, NCI H460 lung, and MCF-7 breast cancer cells. It reduces carrageenan-induced paw edema, as well as ear edema induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014), in mice.3 Verbenalin (5 and 10 mg/kg) reduces increases in malondialdehyde (MDA) levels and the production of reactive oxygen species (ROS) in brain mitochondria isolated from, as well as decreases infarct volume and neurological deficits in, a rat model of ischemia-reperfusion injury induced by middle cerebral artery occlusion (MCAO).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jiang, W.-L., Zhang, S.-P., Zhu, H.-B., et al. Cornin ameliorates cerebral infarction in rats by antioxidant action and stabilization of mitochondrial function. Phytother. Res. 24(4), 547-552 (2010).

    2. Vareed, S.K., Schutzki, R.E., and Nair, M.G. Lipid peroxidation, cyclooxygenase enzyme and tumor cell proliferation inhibitory compounds in Cornus kousa fruits. Phytomedicine 14(10), 706-709 (2007).

    3. Recio, M.d.C., Giner, R.M., Máñez, S., et al. Structural considerations on the iridoids as anti-inflammatory agents. Planta Med. 60(3), 232-234 (1994).