Bacopaside II
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MedKoo CAT#: 573967

CAS#: 382146-66-9

Description: Bacopaside II is a triterpene glycoside found in B. monnieri that has neuroprotective, anti-angiogenic, and anticancer activities. Bacopaside II decreases hydrogen peroxide-induced intracellular reactive oxygen species (ROS) production and cell death in N2a neuroblastoma cells. 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. 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).


Chemical Structure

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Bacopaside II
CAS# 382146-66-9

Theoretical Analysis

MedKoo Cat#: 573967
Name: Bacopaside II
CAS#: 382146-66-9
Chemical Formula: C47H76O18
Exact Mass: 928.5032
Molecular Weight: 929.11
Elemental Analysis: C, 60.76; H, 8.25; O, 31.00

Price and Availability

Size Price Availability Quantity
1.0mg USD 265.0 2 Weeks
5.0mg USD 675.0 2 Weeks
10.0mg USD 1335.0 2 Weeks
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Synonym: Bacopaside II

IUPAC/Chemical Name: (2S,3R,4S,5S,6R)-2-(((2R,3R,4S,5R,6R)-3-(((2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-5-hydroxy-2-(((1S,2R,4aR,6aS,6bR,8aR,10S,12aR,12bR,14aR,14bS)-1-hydroxy-1,6b,9,9,12a-pentamethyl-2-(2-methylprop-1-en-1-yl)hexadecahydro-1H,6H-4a,6a-methanonaphtho[1,2-h]pyrano[2,3-c]isochromen-10-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

InChi Key: WZWPYJOPCULCLQ-UOXCDNDQSA-N

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

SMILES Code: O[C@H]1[C@H](O)[C@@H](CO)O[C@](O[C@@H]2[C@@H](O[C@]3([H])O[C@@H](CO)[C@H](O)[C@H]3O)[C@]([H])(O[C@@H]4C(C)(C)[C@@](CC[C@@](C)([C@@](C[C@]5(OC[C@@H](/C=C(C)\C)[C@]6(C)O)[C@@]76[H])(CO5)[C@]7([H])CC8)[C@@]98[H])([H])[C@]9(C)CC4)O[C@H](CO)[C@H]2O)([H])[C@@H]1O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: Bacopaside II blocks the Aquaporin-1 (AQP1) water channel and impairs migration of cells that express AQP1.
In vitro activity: The AQP1 inhibitor bacopaside II, derived from medicinal plant Bacopa monnieri, was tested on endothelial cell migration and tube-formation in vitro using mouse endothelial cell lines (2H11 and 3B11) and human umbilical vein endothelial cells (HUVEC). The effect of bacopaside II on viability, apoptosis, migration and tubulogenesis was assessed by a proliferation assay, annexin-V/propidium iodide flow cytometry, the scratch wound assay and endothelial tube-formation, respectively. Cell viability was reduced significantly for 2H11 at 15 μM (p = 0.037), 3B11 at 12.5 μM (p = 0.017) and HUVEC at 10 μM (p < 0.0001). At 15 μM, the reduced viability was accompanied by an increase in apoptosis of 38%, 50% and 32% for 2H11, 3B11 and HUVEC, respectively. Bacopaside II at ≥10 μM significantly reduced migration of 2H11 (p = 0.0002) and 3B11 (p = 0.034). HUVECs were most sensitive with a significant reduction at ≥7.5 μM (p = 0.037). Tube-formation was reduced with a 15 μM dose for all cell lines and 10 μM for 3B11 (p < 0.0001). Reference: Int J Mol Sci. 2018 Feb 26;19(3):653. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5877514/
In vivo activity: TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 929.11 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Palethorpe HM, Tomita Y, Smith E, Pei JV, Townsend AR, Price TJ, Young JP, Yool AJ, Hardingham JE. The Aquaporin 1 Inhibitor Bacopaside II Reduces Endothelial Cell Migration and Tubulogenesis and Induces Apoptosis. Int J Mol Sci. 2018 Feb 26;19(3):653. doi: 10.3390/ijms19030653. PMID: 29495367; PMCID: PMC5877514. 2. Smith E, Palethorpe HM, Tomita Y, Pei JV, Townsend AR, Price TJ, Young JP, Yool AJ, Hardingham JE. The Purified Extract from the Medicinal Plant Bacopa monnieri, Bacopaside II, Inhibits Growth of Colon Cancer Cells In Vitro by Inducing Cell Cycle Arrest and Apoptosis. Cells. 2018 Jul 21;7(7):81. doi: 10.3390/cells7070081. PMID: 30037060; PMCID: PMC6070819.
In vitro protocol: 1. Palethorpe HM, Tomita Y, Smith E, Pei JV, Townsend AR, Price TJ, Young JP, Yool AJ, Hardingham JE. The Aquaporin 1 Inhibitor Bacopaside II Reduces Endothelial Cell Migration and Tubulogenesis and Induces Apoptosis. Int J Mol Sci. 2018 Feb 26;19(3):653. doi: 10.3390/ijms19030653. PMID: 29495367; PMCID: PMC5877514. 2. Smith E, Palethorpe HM, Tomita Y, Pei JV, Townsend AR, Price TJ, Young JP, Yool AJ, Hardingham JE. The Purified Extract from the Medicinal Plant Bacopa monnieri, Bacopaside II, Inhibits Growth of Colon Cancer Cells In Vitro by Inducing Cell Cycle Arrest and Apoptosis. Cells. 2018 Jul 21;7(7):81. doi: 10.3390/cells7070081. PMID: 30037060; PMCID: PMC6070819.
In vivo protocol: TBD

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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 al. Triterpene 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 al. The 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 al. Antitumor activities of dammarane triterpene saponins from Bacopa monniera. Phytother. Res. 24(6), 864-868 (2010).