A secoiridoid glycoside with diverse biological activities
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Amarogentin

Item No. 24914

Technical Information
Formal Name
5-ethenyl-4,4aS,5R,6S-tetrahydro-6-[[2-O-[(3,3',5-trihydroxy[1,1'-biphenyl]-2-yl)carbonyl]-β-D-glucopyranosyl]oxy]-1H,3H-pyrano[3,4-c]pyran-1-one
CAS Number
21018-84-8
Molecular Formula
C29H30O13
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 1 mg/mlDMSO: 2 mg/mlPBS (pH 7.2): 0.1 mg/ml
λmax
218, 228, 264, 302 nm
SMILES
O=C1OCC[C@]2([H])C1=CO[C@@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC(C4=C(C5=CC=CC(O)=C5)C=C(O)C=C4O)=O)[C@@H]2C=C
InChi Code
InChI=1S/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1
InChi Key
DBOVHQOUSDWAPQ-WTONXPSSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Amarogentin is a secoiridoid glycoside that has been found in Swertia and has diverse biological activities, including anticancer, antidiabetic, and anti-leishmanial properties.1,2,3 It inhibits the growth of SNU-16 human gastric cancer cells (IC50 = 12.4 µM after 48 hours) and increases apoptosis when used at a concentration of 50 µM.2 Amarogentin (10-50 mg/kg, s.c.) dose-dependently reduces tumor growth in a SNU-16 nude mouse xenograft model. It reduces plasma glucose levels in a rat model of diabetes induced by streptozotocin (STZ; Item No. 13104) in a dose-dependent manner and reverses the STZ-induced increase in soleus muscle levels of glucose transporter 4 (Glut4) when administered at a dose of 0.5 mg/kg.3 Amarogentin reduces parasite burden in the spleen of hamsters infected with L. donovani in a dose-dependent manner.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Medda, S., Mukhopadhyay, S., and Basu, M.K. Evaluation of the in-vivo activity and toxicity of amarogentin, an antileishmanial agent, in both liposomal and niosomal forms. J. Antimicrob. Chemother. 44(6), 791-794 (1999).

    2. Zhao, J.G., Zhang, L., Xiang, X.-j., et alAmarogentin secoiridoid inhibits in vivo cancer cell growth in xenograft mice model and induces apoptosis in human gastric cancer cells (SNU-16) through G2/M cell cycle arrest and PI3K/Akt signalling pathway. J. BUON. 21(3), 609-617 (2016).

    3. Niu, H.S., Chao, P.-C., Ku, P.-M., et alAmarogentin ameliorates diabetic disorders in animal models. Naunyn Schmiedebergs Arch. Pharmacol. 389(11), 1215-1223 (2016).