An iridoid glycoside with diverse biological activities
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Agnuside

Item No. 24971

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1S,4aR,5S,7aS-tetrahydro-5-hydroxy-7-[[(4-hydroxybenzoyl)oxy]methyl]cyclopenta[c]pyran-1-yl, β-D-glucopyranoside
CAS Number
11027-63-7
Molecular Formula
C22H26O11
Formula Weight
466.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 0.5 mg/mlPBS (pH 7.2): 0.2 mg/ml
λmax
203, 259 nm
SMILES
OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@](O[C@H]2[C@@](C(COC(C3=CC=C(O)C=C3)=O)=C[C@H]4O)([H])[C@@]4([H])C=CO2)([H])O1
InChi Code
InChI=1S/C22H26O11/c23-8-15-17(26)18(27)19(28)22(32-15)33-21-16-11(7-14(25)13(16)5-6-30-21)9-31-20(29)10-1-3-12(24)4-2-10/h1-7,13-19,21-28H,8-9H2/t13-,14+,15+,16+,17+,18-,19+,21-,22-/m0/s1
InChi Key
GLACGTLACKLUJX-QNAXTHAFSA-N
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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    5 mg

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    10 mg

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    25 mg

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    Product Description

    Agnuside is an iridoid glycoside originally isolated from V. rotundifolia fruit that has diverse biological activities.1,2,3,4 It inhibits COX-2 with an IC50 value of 0.026 mg/ml but exhibits less than 10% inhibition of COX-1 at this concentration.1 It also inhibits 46.3, 66.8, and 82.1% of P-glycoprotein (P-gp) ATPase activity at concentrations of 5, 25, and 100 μM, respectively.5 Agnuside (0.1-10 μM) induces proliferation of MCF-7 breast cancer cells, an effect that is inhibited by the estrogen receptor antagonist fulvestrant (ICI 182780; Item No. 10011269).2 In vivo, agnuside (50 mg/kg) reduces acetic acid-induced writhing in mice indicating analgesia.3 It also suppresses production of the pro-inflammatory mediators prostaglandin E2 (PGE2) and leukotriene B4 (LTB4; Item No. 20110) and the T cell-mediated cytokines IL-2, TNF-α, INF-γ, IL-4, IL-10, and IL-17 in splenocytes and arthritic paw tissue from arthritic adrenalectomized rats.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Suksamrarn, A., Kumpun, S., Kirtikara, K., et al. Iridoids with anti-inflammatory activity from Vitex peduncularis. Planta Med. 68(1), 72-73 (2002).

    2. Hu, Y., Hou, T.T., Zhang, Q.Y., et al. Evaluation of the estrogenic activity of the constituents in the fruits of Vitex rotundifolia L. for the potential treatment of premenstrual syndrome. J. Pharm. Pharmacol. 59(9), 1307-1312 (2007).

    3. Okuyama, E., Fujimori, S., Yamazaki, M., et al. Pharmacologically active components of viticis fructus (Vitex rotundifolia). II. The components having analgesic effects. Chem. Pharm. Bull. (Tokyo) 46(4), 655-662 (1998).

    4. Pandey, A., Bani, S., Satti, N.K., et al. Anti-arthritic activity of agnuside mediated through the down-regulation of inflammatory mediators and cytokines. Inflamm. Res. 61(4), 293-304 (2012).

    5. Najar, I.A., Sachin, B.S., Sharma, S.C., et al. Modulation of P-glycoprotein ATPase activity by some phytoconstituents. Phytother. Res. 24(3), 454-458 (2010).