Bacopaside II | CAS# 382146-66-9 | triterpene glycoside

MedKoo Cat#: 573967 | Name: Bacopaside II

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

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
5mg	USD 650.00	2 weeks
10mg	USD 1,250.00	2 weeks

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Related CAS #

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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

More Info

Product Data

Product Data

Instruction

View handling instruction

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.

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:

In vivo protocol:

TBD

1: Anwar S, Mohammad T, Azhar MK, Fatima H, Alam A, Hasan GM, Islam A, Kaur P, Hassan MI. Investigating MARK4 inhibitory potential of Bacopaside II: Targeting Alzheimer's disease. Int J Biol Macromol. 2023 Jun 12:125364. doi: 10.1016/j.ijbiomac.2023.125364. Epub ahead of print. PMID: 37315665. 2: 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. 3: Tomita Y, Smith E, Palethorpe HM, Nakhjavani M, Yeo KKL, Townsend AR, Price TJ, Yool AJ, Hardingham JE. In Vitro Synergistic Inhibition of HT-29 Proliferation and 2H-11 and HUVEC Tubulogenesis by Bacopaside I and II Is Associated with Ca2+ Flux and Loss of Plasma Membrane Integrity. Pharmaceuticals (Basel). 2021 May 6;14(5):436. doi: 10.3390/ph14050436. PMID: 34066415; PMCID: PMC8148107. 4: Sekhar VC, Viswanathan G, Baby S. Insights Into the Molecular Aspects of Neuroprotective Bacoside A and Bacopaside I. Curr Neuropharmacol. 2019;17(5):438-446. doi: 10.2174/1570159X16666180419123022. PMID: 29676230; PMCID: PMC6520587. 5: 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. 6: De Ieso ML, Pei JV, Nourmohammadi S, Smith E, Chow PH, Kourghi M, Hardingham JE, Yool AJ. Combined pharmacological administration of AQP1 ion channel blocker AqB011 and water channel blocker Bacopaside II amplifies inhibition of colon cancer cell migration. Sci Rep. 2019 Sep 2;9(1):12635. doi: 10.1038/s41598-019-49045-9. PMID: 31477744; PMCID: PMC6718670. 7: Chakravarty AK, Sarkar T, Masuda K, Shiojima K, Nakane T, Kawahara N. Bacopaside I and II: two pseudojujubogenin glycosides from Bacopa monniera. Phytochemistry. 2001 Oct;58(4):553-6. doi: 10.1016/s0031-9422(01)00275-8. Erratum in: Phytochemistry 2002 Feb;59(3):365. PMID: 11576596. 8: Yen DTH, Cuc NT, Tai BH, Van Kiem P, Hoang Duc M, Nhiem NX, Cho SH, Jeong SB, Seo Y, Park S. Two new triterpenoid glycosides from Bacopa monnieri and their cytotoxic activity. Nat Prod Res. 2022 Oct 14:1-7. doi: 10.1080/14786419.2022.2132498. Epub ahead of print. PMID: 36239487. 9: Pei JV, Kourghi M, De Ieso ML, Campbell EM, Dorward HS, Hardingham JE, Yool AJ. Differential Inhibition of Water and Ion Channel Activities of Mammalian Aquaporin-1 by Two Structurally Related Bacopaside Compounds Derived from the Medicinal Plant Bacopa monnieri. Mol Pharmacol. 2016 Oct;90(4):496-507. doi: 10.1124/mol.116.105882. Epub 2016 Jul 29. PMID: 27474162. 10: Phrompittayarat W, Putalun W, Tanaka H, Wittaya-Areekul S, Jetiyanon K, Ingkaninan K. An enzyme-linked immunosorbant assay using polyclonal antibodies against bacopaside I. Anal Chim Acta. 2007 Feb 12;584(1):1-6. doi: 10.1016/j.aca.2006.11.017. Epub 2006 Nov 12. PMID: 17386577. 11: Deepak M, Amit A. 'Bacoside B'--the need remains for establishing identity. Fitoterapia. 2013 Jun;87:7-10. doi: 10.1016/j.fitote.2013.03.011. Epub 2013 Mar 16. PMID: 23506783. 12: Murthy PB, Raju VR, Ramakrisana T, Chakravarthy MS, Kumar KV, Kannababu S, Subbaraju GV. Estimation of twelve bacopa saponins in Bacopa monnieri extracts and formulations by high-performance liquid chromatography. Chem Pharm Bull (Tokyo). 2006 Jun;54(6):907-11. doi: 10.1248/cpb.54.907. PMID: 16755069. 13: Palethorpe HM, Smith E, Tomita Y, Nakhjavani M, Yool AJ, Price TJ, Young JP, Townsend AR, Hardingham JE. Bacopasides I and II Act in Synergy to Inhibit the Growth, Migration and Invasion of Breast Cancer Cell Lines. Molecules. 2019 Sep 30;24(19):3539. doi: 10.3390/molecules24193539. PMID: 31574930; PMCID: PMC6803832. 14: Sahoo KK, Sahu BB, Singh VR, Patra N. Enhanced production of Bacopa saponins by repeated batch strategy in bioreactor. Bioprocess Biosyst Eng. 2022 May;45(5):829-841. doi: 10.1007/s00449-022-02700-4. Epub 2022 Feb 4. PMID: 35119526. 15: Singh R, Ramakrishna R, Bhateria M, Bhatta RS. In vitro evaluation of Bacopa monniera extract and individual constituents on human recombinant monoamine oxidase enzymes. Phytother Res. 2014 Sep;28(9):1419-22. doi: 10.1002/ptr.5116. Epub 2014 Jan 21. PMID: 24449518. 16: Dixit H, Selvaa Kumar C, Dasgupta D, Gadewal N. Molecular docking analysis of hyperphosphorylated tau protein with compounds derived from Bacopa monnieri and Withania somnifera. Bioinformation. 2021 Sep 30;17(9):798-804. doi: 10.6026/97320630017798. PMID: 35539884; PMCID: PMC9049085. 17: Peng L, Zhou Y, Kong de Y, Zhang WD. Antitumor activities of dammarane triterpene saponins from Bacopa monniera. Phytother Res. 2010 Jun;24(6):864-8. doi: 10.1002/ptr.3034. PMID: 19960417. 18: Singh R, Rachumallu R, Bhateria M, Panduri J, Bhatta RS. In vitro effects of standardized extract of Bacopa monniera and its five individual active constituents on human P-glycoprotein activity. Xenobiotica. 2015;45(8):741-9. doi: 10.3109/00498254.2015.1017752. Epub 2015 Apr 14. PMID: 25869246. 19: Majumdar S, Garai S, Jha S. Use of the cryptogein gene to stimulate the accumulation of Bacopa saponins in transgenic Bacopa monnieri plants. Plant Cell Rep. 2012 Oct;31(10):1899-909. doi: 10.1007/s00299-012-1303-3. Epub 2012 Jun 26. PMID: 22733208. 20: Zhou Y, Peng L, Zhang WD, Kong DY. Effect of triterpenoid saponins from Bacopa monniera on scopolamine-induced memory impairment in mice. Planta Med. 2009 May;75(6):568-74. doi: 10.1055/s-0029-1185339. Epub 2009 Feb 12. PMID: 19214943.(2010).