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Bacoside A3

CAS# 157408-08-7

Bacoside A3

2D Structure

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Bacoside A3

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Chemical Properties of Bacoside A3

Cas No. 157408-08-7 SDF Download SDF
PubChem ID 91827005 Appearance White powder
Formula C47H76O18 M.Wt 929
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms 3-beta-((O-beta-D-glucopyranosyl(1-3)-O-(alpha-L-arabinofuranosyl(1-2))-O-beta-D-glucopyranosyl)oxy)jujubogenin
Solubility Soluble in ethanol and methanol; insoluble in chloroform and n-hexane
Chemical Name (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-5-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-2-(hydroxymethyl)-6-[[(1S,2R,5R,7S,10R,11R,14R,15S,16S,18R,20S)-16-hydroxy-2,6,6,10,16-pentamethyl-18-(2-methylprop-1-enyl)-19,21-dioxahexacyclo[18.2.1.01,14.02,11.05,10.015,20]tricosan-7-yl]oxy]oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES CC(=CC1CC(C2C3CCC4C5(CCC(C(C5CCC4(C36CC2(O1)OC6)C)(C)C)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(O9)CO)O)O)C)(C)O)C
Standard InChIKey CDEVGTJBRPBOPH-INTDMYAHSA-N
Standard InChI InChI=1S/C47H76O18/c1-21(2)14-22-15-45(7,57)38-23-8-9-28-43(5)12-11-29(42(3,4)27(43)10-13-44(28,6)46(23)19-47(38,65-22)58-20-46)62-41-37(64-39-34(55)31(52)25(17-49)60-39)36(32(53)26(18-50)61-41)63-40-35(56)33(54)30(51)24(16-48)59-40/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-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Bacoside A3

The herbs of Bacopa monnieri

Biological Activity of Bacoside A3

DescriptionBacoside A3 has antioxidant potential, it shows comparatively higher neuroprotective response analysed as higher cell viability and decreased intracellular ROS. Bacoside A3 shows a newer potential role in the clinical management of opioid withdrawal induced depression. Bacoside A3 inhibited both basal activity as well as verapamil-stimulated ATPase activity, thus its affinity towards P-gp; the interaction of bacosides (A3/A) with Tryptophan hydroxylase (TPH) might up-regulate its activity to elevate the biosynthesis of 5-HT, thereby enhances learning and memory formation.
TargetsROS | P-gp | 5-HT recepter | ATPase
In vitro

Comparative evaluation of four triterpenoid glycoside saponins of bacoside A in alleviating sub-cellular oxidative stress of N2a neuroblastoma cells.[Pubmed: 30073654 ]

J Pharm Pharmacol. 2018 Nov;70(11):1531-1540.

To examine the neuroprotective property of triterpenoid glycoside saponins of Bacopa monnieri (L.) Wettst. bacoside A and its components against H2 O2 -induced oxidative stress on neuronal (N2a) cells.
METHODS AND RESULTS:
The cytoprotective effects of individual bacoside A components were evaluated towards oxidative stressed neuronal cells. Bacoside A was screened for neuronal cell viability (MTT assay) and change in intracellular reactive oxygen species (ROS), anti-apoptotic properties and mitochondrial membrane potential (MMP) using fluorescence microscopy. Different bacoside A components showed decrease in N2a cell viability below 100 (%) after bacoside A concentration of 0.4 mg/ml. Further, cytoprotective effect of optimized dose of bacoside A was analysed for alleviating oxidative stressed, apoptosis and MMP in H2 O2 stressed neuronal cells. Results showed increase in MMP, and decrease in apoptotic induction, without much change in nuclear integrity in stressed neuronal cells. Results showed Bacoside A3 and bacopaside II have comparatively higher cytoprotective ability whilst isomer of bacopasponin C, bacopasaponin C and mixture showed comparatively less response.
CONCLUSIONS:
Amongst four different bacoside A components, Bacoside A3 and bacopaside II showed comparatively higher neuroprotective response analysed as higher cell viability and decreased intracellular ROS, suggesting better regulation of cyto-(neuronal) protection of N2a cells.

Molecular docking of bacosides with tryptophan hydroxylase: a model to understand the bacosides mechanism.[Pubmed: 25089244]

Nat Prod Bioprospect. 2014 Aug;4(4):251-5.

Tryptophan hydroxylase (TPH) catalyses l-tryptophan into 5-hydroxy-l-tryptophan, which is the first and rate-limiting step of serotonin (5-HT) biosynthesis. Earlier, we found that TPH2 up-regulated in the hippocampus of postnatal rats after the oral treatment of Bacopa monniera leaf extract containing the active compound bacosides. However, the knowledge about the interactions between bacosides with TPH is limited.
METHODS AND RESULTS:
In this study, we take advantage of in silico approach to understand the interaction of bacoside-TPH complex using three different docking algorithms such as HexDock, PatchDock and AutoDock. All these three algorithms showed that bacoside A and Bacoside A3 well fit into the cavity consists of active sites. Further, our analysis revealed that major active compounds Bacoside A3 and A interact with different residues of TPH through hydrogen bond. Interestingly, Tyr235, Thr265 and Glu317 are the key residues among them, but none of them are either at tryptophan or BH4 binding region. However, its note worthy to mention that Tyr 235 is a catalytic sensitive residue, Thr265 is present in the flexible loop region and Glu317 is known to interacts with Fe. Interactions with these residues may critically regulate TPH function and thus serotonin synthesis.
CONCLUSIONS:
Our study suggested that the interaction of bacosides (A3/A) with TPH might up-regulate its activity to elevate the biosynthesis of 5-HT, thereby enhances learning and memory formation.

In vivo

Beneficial effects of Bacopa monnieri extract on opioid induced toxicity.[Pubmed: 27441247 ]

Heliyon. 2016 Feb 15;2(2):e00068.

The present study examined the hepatotoxicity and nephrotoxicity of morphine and illicit street heroin and their amelioration by a standardized methanolic extract of Bacopa monnieri (L.) (mBME) in rats.
METHODS AND RESULTS:
Morphine or street heroin was administered at a dose of 20 mg/kg for 14 and 21 days. mBME (40 mg/kg) or ascorbic acid (50 mg/kg) was administered two hours before morphine or street heroin. High performance liquid chromatography (HPLC) was used for the standardization of bacoside-A major components in mBME. The antioxidant potential of mBME was evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assay. Administration of morphine and street heroin resulted in marked elevation of serum alanine aminotransferase (ALT), aspartate aminotransferase (AST) and creatinine. Histopathological changes induced by morphine and street heroin after 14 days were of reversible nature while treatment for 21 days was associated with irreversible changes. Pretreatment with mBME or ascorbic acid restored the elevation of serum ALT, AST and creatinine and protected liver and kidneys from the toxicological influence of morphine and street heroin. HPLC analysis showed that mBME contained bacoside A major components i.e. Bacoside A3 (37.5 μg/mg), bacopaside II (4.62 μg/mg) and bacopasaponin-C (1.91 μg/mg). The EC50 for the DPPH free radical scavenging assay revealed that mBME possessed strong antioxidant potential. These results concluded that as compared to morphine, street heroin was associated with severe biochemical and histopathological changes in the liver and kidneys.
CONCLUSIONS:
Bacopa monnieri having strong antioxidant potential may provide a beneficial herbal remedy for the efficient management of opioid related hepatotoxicity and nephrotoxicity.

Protocol of Bacoside A3

Kinase Assay

In vitro effects of standardized extract of Bacopa monniera and its five individual active constituents on human P-glycoprotein activity.[Pubmed: 25869246 ]

Xenobiotica. 2015;45(8):741-9.

1. For centuries Bacopa monniera (BM) has been used as an herbal drug for the treatment of various mental ailments. A chemically standardized alcoholic extract of BM is clinically available over the counter herbal remedy for memory enhancement in children and adults. Consumption of herbal preparations has been reported to alter the function of membrane transporters, especially P-glycoprotein (P-gp), ATP-dependent drug efflux transporter responsible for the development of herb-drug interactions.
METHODS AND RESULTS:
2. In the present study, we evaluated the in vitro effect of BM extract and its five individual active constituents (namely, bacopaside I, bacopaside II and bacopasaponin C, bacoside A and Bacoside A3) on P-gp function using luminescent P-gp ATPase assay and Rh123 transport assay across human MDR1 gene transfected LLC-GA5-COL150 cell line. 3. It was observed that BM extract and its five individual constituents inhibited both basal activity as well as verapamil-stimulated ATPase activity, suggesting their affinity towards P-gp. Further, BM and its five active constituents inhibited the rhodamine 123 (Rh123) transport across LLC-GA5-COL150 cell monolayer with bacopaside II being the most potent inhibitor of P-gp, which decreased P-gp efflux ratio of Rh123 by fourfold in comparison to control.
CONCLUSIONS:
4. Our finding may prove beneficial in predicting the potential herb-drug interactions of BM on concomitant medication with P-gp substrate drugs in clinical settings.

Animal Research

Inhibitory effect of bacopasides on spontaneous morphine withdrawal induced depression in mice.[Pubmed: 24243728]

Phytother Res. 2014 Jun;28(6):937-9.

Bacopa monnieri is a perennial herb with a world known image as a nootropic.
METHODS AND RESULTS:
We investigated the effect of Bacopa monnieri methanolic extract (Mt Ext BM) 10, 20, and 30 mg/kg body weight (b.w) on acquisition and expression of morphine withdrawal induced depression in mice. Locally available Bacopa monnieri (BM) was screened for contents of Bacoside A3, Bacopasaponin C, and Bacopaside II using HPLC with UV. Morphine dependence was induced in mice using twice daily escalating chronic morphine treatments (20-65 mg/kg b.w) for eight consecutive days. Morphine withdrawal induced depression was assayed in animals using forced swimming test (FST), three days after last morphine injection. The HPLC analysis revealed that Mt-ext BM contained Bacoside A3 as major component, i.e. 4 µg in each mg of extract. The chronic treatment with Met Ext BM 10, 20, and 30 mg/kg b.w. dosing significantly inhibited opioid withdrawal induced depression in mice.
CONCLUSIONS:
These findings imply a newer potential role of Bacopa monnieri in the clinical management of opioid withdrawal induced depression which can be attributed to Bacoside A3.

Bacoside A3 Dilution Calculator

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Bacoside A3 Molarity Calculator

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Preparing Stock Solutions of Bacoside A3

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.0764 mL 5.3821 mL 10.7643 mL 21.5285 mL 26.9107 mL
5 mM 0.2153 mL 1.0764 mL 2.1529 mL 4.3057 mL 5.3821 mL
10 mM 0.1076 mL 0.5382 mL 1.0764 mL 2.1529 mL 2.6911 mL
50 mM 0.0215 mL 0.1076 mL 0.2153 mL 0.4306 mL 0.5382 mL
100 mM 0.0108 mL 0.0538 mL 0.1076 mL 0.2153 mL 0.2691 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Bacoside A3

HPLC analysis and standardization of Brahmi vati - An Ayurvedic poly-herbal formulation.[Pubmed:24396246]

J Young Pharm. 2013 Sep;5(3):77-82.

OBJECTIVES: The aim of the present study was to standardize Brahmi vati (BV) by simultaneous quantitative estimation of Bacoside A3 and Piperine adopting HPLC-UV method. BV very important Ayurvedic polyherbo formulation used to treat epilepsy and mental disorders containing thirty eight ingredients including Bacopa monnieri L. and Piper longum L. MATERIALS AND METHODS: An HPLC-UV method was developed for the standardization of BV in light of simultaneous quantitative estimation of Bacoside A3 and Piperine, the major constituents of B. monnieri L. and P. longum L. respectively. The developed method was validated on parameters including linearity, precision, accuracy and robustness. RESULTS: The HPLC analysis showed significant increase in amount of Bacoside A3 and Piperine in the in-house sample of BV when compared with all three different marketed samples of the same. Results showed variations in the amount of Bacoside A3 and Piperine in different samples which indicate non-uniformity in their quality which will lead to difference in their therapeutic effects. CONCLUSION: The outcome of the present investigation underlines the importance of standardization of Ayurvedic formulations. The developed method may be further used to standardize other samples of BV or other formulations containing Bacoside A3 and Piperine.

Inhibitory effect of bacopasides on spontaneous morphine withdrawal induced depression in mice.[Pubmed:24243728]

Phytother Res. 2014 Jun;28(6):937-9.

Bacopa monnieri is a perennial herb with a world known image as a nootropic. We investigated the effect of Bacopa monnieri methanolic extract (Mt Ext BM) 10, 20, and 30 mg/kg body weight (b.w) on acquisition and expression of morphine withdrawal induced depression in mice. Locally available Bacopa monnieri (BM) was screened for contents of Bacoside A3, Bacopasaponin C, and Bacopaside II using HPLC with UV. Morphine dependence was induced in mice using twice daily escalating chronic morphine treatments (20-65 mg/kg b.w) for eight consecutive days. Morphine withdrawal induced depression was assayed in animals using forced swimming test (FST), three days after last morphine injection. The HPLC analysis revealed that Mt-ext BM contained Bacoside A3 as major component, i.e. 4 microg in each mg of extract. The chronic treatment with Met Ext BM 10, 20, and 30 mg/kg b.w. dosing significantly inhibited opioid withdrawal induced depression in mice. These findings imply a newer potential role of Bacopa monnieri in the clinical management of opioid withdrawal induced depression which can be attributed to Bacoside A3.

Keywords:

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