A triterpene glycoside
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Bacopaside II

Item No. 11822

Technical Information
Formal Name
(1S,2R,4aR,6aS,6bR,8aR,10S,12aR,12bR,14aR,14bS)-hexadecahydro-1-hydroxy-1,6b,9,9,12a-pentamethyl-2-(2-methyl-1-propen-1-yl)-4a,6a-methano-1H,6H-phenanthro[2,1-d]pyrano[2,3-b]pyran-10-yl O-α-L-arabinofuranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside
CAS Number
382146-66-9
Molecular Formula
C47H76O18
Formula Weight
Purity
≥95%
A crystalline solid
Methanol: soluble
SMILES
O[C@@H]1[C@@H](O)[C@H](CO)O[C@@]1([H])O[C@@H]2[C@@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@@H](CO)O[C@@]2([H])O[C@H]4CC[C@@]5(C)[C@](CC[C@]6(C)[C@]5([H])CC[C@@]7([H])[C@@]68C[C@@]9(OC8)[C@]7([H])[C@@](C)(O)[C@H](/C=C(C)\C)CO9)([H])C4(C)C
InChi Code
InChI=1S/C47H76O18/c1-21(2)14-22-18-58-47-19-46(20-59-47)23(38(47)45(22,7)57)8-9-28-43(5)12-11-29(42(3,4)27(43)10-13-44(28,46)6)63-41-37(65-39-34(55)31(52)25(16-49)61-39)36(32(53)26(17-50)62-41)64-40-35(56)33(54)30(51)24(15-48)60-40/h14,22-41,48-57H,8-13,15-20H2,1-7H3/t22-,23-,24-,25+,26-,27+,28-,29+,30-,31+,32-,33+,34-,35-,36+,37-,38+,39+,40+,41+,43+,44-,45+,46+,47-/m1/s1
InChi Key
WZWPYJOPCULCLQ-UOXCDNDQSA-N
Origin
Plant/Bacopa monnieri (L.)
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Bacopaside II is a triterpene glycoside found in B. monnieri that has neuroprotective, anti-angiogenic, and anticancer activities.1,2,3,4 Bacopaside II (0.4 mg/ml) decreases hydrogen peroxide-induced intracellular reactive oxygen species (ROS) production and cell death in N2a neuroblastoma cells.1 It decreases immobility time in the forced swim and tail suspension tests in mice, indicating anti-depressant like activity, when administered at a dose of 50 mg/kg.2 Bacopaside II decreases migration and tube formation in 2H11 and 3B11 cells, as well as human umbilical vein endothelial cells (HUVECs) when used at concentrations greater than 15 µM.3 Bacopaside II inhibits the growth of MDA-MB-231, SHG-44, HCT8, A549, and PC3M cancer cells (IC50s = 32.4, 36.9, 40.3, 44.4, and 45.4 µM, respectively).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bhardwaj, P., Jain, C.K., and Mathur, A. Comparative evaluation of four triterpenoid glycoside saponins of bacoside A in alleviating sub-cellular oxidative stress of N2a neuroblastoma cells. J. Pharm. Pharmacol. 70(11), 1531-1540 (2018).

    2. Zhou, Y., Shen, Y.-H., Zhang, C., et alTriterpene saponins from Bacopa monnieri and their antidepressant effects in two mice models. J. Nat. Prod. 70(4), 652-655 (2007).

    3. Palethorpe, H.M., Tomita, Y., Smith, E., et alThe aquaporin 1 inhibitor bacopaside II reduces endothelial cell migration and tubulogenesis and induces apoptosis. Int. J. Mol. Sci. 19(3), E653 (2018).

    4. Peng, L., Zhou, Y., Kong, D.Y., et alAntitumor activities of dammarane triterpene saponins from Bacopa monniera. Phytother. Res. 24(6), 864-868 (2010).