An iridoid glycoside with diverse biological activities
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Isomer(s)
34047Shanzhiside methyl ester
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Acetylharpagide

Item No. 39930

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,4aS,5R,7S,7aS)-7-(acetyloxy)-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methylcyclopenta[c]pyran-1-yl, β-D-glucopyranoside
CAS Number
6926-14-3
Synonyms
  • 8-Acetylharpagide
  • 8-O-Acetylharpagide
  • 8-AcHarp
  • Harpagide Acetate
Molecular Formula
C17H26O11
Formula Weight
406.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: SolubleWater: Soluble
SMILES
O[C@@]([C@@H]1O)(C=CO2)[C@]([C@](C)(C1)OC(C)=O)([H])[C@@H]2O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]([C@H]3O)CO
InChi Code
InChI=1S/C17H26O11/c1-7(19)28-16(2)5-9(20)17(24)3-4-25-15(13(16)17)27-14-12(23)11(22)10(21)8(6-18)26-14/h3-4,8-15,18,20-24H,5-6H2,1-2H3/t8-,9-,10-,11+,12-,13-,14+,15+,16+,17-/m1/s1
InChi Key
CAFTUQNGDROXEZ-XBDCZORHSA-N
Origin
Plant/Scrophularia ningpoensis Hemsl.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Acetylharpagide is an iridoid glycoside that has been found in A. decumbens and has diverse biological activities.1,2,3 It reduces the proliferation of A431 skin cancer cells (IC50 = 310 µM).1 Acetylharpagide (0.005% in the drinking water) reduces the number of tumors per mouse and the percentage of mice with tumors in a mouse model of 4-nitroquinolin 1-oxide-induced carcinogenesis.2 It decreases carrageenan-induced paw swelling in rats when administered at a dose of 10 mg/kg.3 Acetylharpagide (10 mg/kg) reduces blood glucose levels in a mouse model of type I diabetes induced by alloxan (Item No. 9002196).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kuria, K.A.M., Chepkwony, H., Govaerts, C., et al. The antiplasmodial activity of isolates from Ajuga remota. J. Nat. Prod. 65(5), 789-793 (2002).

    2. Takasaki, M., Tokuda, H., Nishino, H., et al. Cancer chemopreventive agents (antitumor-promoters) from Ajuga decumbens. J. Nat. Prod. 62(7), 972-975 (1999).

    3. Ahmed, B., Al-Rehaily, A.J., Al-Howiriny, T.A., et al. Scropolioside-D2 and harpagoside-B: Two new iridoid glycosides from Scrophularia deserti and their antidiabetic and antiinflammatory activity. Biol. Pharm. Bull. 26(4), 462-467 (2003).