Hederasaponin B

CAS# 36284-77-2

Hederasaponin B

Catalog No. BCN1085----Order now to get a substantial discount!

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Quality Control of Hederasaponin B

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Chemical structure

Hederasaponin B

3D structure

Chemical Properties of Hederasaponin B

Cas No. 36284-77-2 SDF Download SDF
PubChem ID 21626480 Appearance White powder
Formula C59H96O25 M.Wt 1205.4
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
SMILES CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(CC4C6=CCC7C8(CCC(C(C8CCC7(C6(CC5)C)C)(C)C)OC9C(C(C(CO9)O)O)OC1C(C(C(C(O1)C)O)O)O)C)(C)C)O)O)O)CO)O)O)O
Standard InChIKey NVSLBOBPSCMMSO-BVLVEXITSA-N
Standard InChI InChI=1S/C59H96O25/c1-24-34(62)38(66)42(70)49(77-24)82-46-29(21-60)79-48(45(73)41(46)69)76-23-30-37(65)40(68)44(72)51(80-30)84-53(74)59-18-16-54(3,4)20-27(59)26-10-11-32-56(7)14-13-33(55(5,6)31(56)12-15-58(32,9)57(26,8)17-19-59)81-52-47(36(64)28(61)22-75-52)83-50-43(71)39(67)35(63)25(2)78-50/h10,24-25,27-52,60-73H,11-23H2,1-9H3/t24-,25-,27-,28-,29+,30+,31-,32+,33-,34-,35-,36-,37+,38+,39+,40-,41+,42+,43+,44+,45+,46+,47+,48+,49-,50-,51-,52-,56-,57+,58+,59-/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 Hederasaponin B

The herbs of Hedera nepalensis

Biological Activity of Hederasaponin B

DescriptionHederasaponin B has antiviral activity, via inhibiting the viral VP2 protein expression and blocking viral capsid protein synthesis. It also has antitumor activity, and it inhibits the superoxide generation induced by arachidonic acid (AA).
TargetsAntifection
In vitro

Antiviral Activity of Hederasaponin B from Hedera helix against Enterovirus 71 Subgenotypes C3 and C4a.[Pubmed: 24596620]

Biomol Ther (Seoul). 2014 Jan;22(1):41-6.

Enterovirus 71 (EV71) is the predominant cause of hand, foot and mouth disease (HFMD). The antiviral activity of Hederasaponin B from Hedera helix against EV71 subgenotypes C3 and C4a was evaluated in vero cells.
METHODS AND RESULTS:
In the current study, the antiviral activity of Hederasaponin B against EV71 C3 and C4a was determined by cytopathic effect (CPE) reduction method and western blot assay. Our results demonstrated that Hederasaponin B and 30% ethanol extract of Hedera helix containing Hederasaponin B showed significant antiviral activity against EV71 subgenotypes C3 and C4a by reducing the formation of a visible CPE. Hederasaponin B also inhibited the viral VP2 protein expression, suggesting the inhibition of viral capsid protein synthesis.
CONCLUSIONS:
These results suggest that Hederasaponin B and Hedera helix extract containing Hederasaponin B can be novel drug candidates with broad-spectrum antiviral activity against various subgenotypes of EV71.

Triterpenoid saponins from Anemone flaccida induce apoptosis activity in HeLa cells.[Pubmed: 19219723]

J Asian Nat Prod Res. 2009;11(2):122-7.

Five triterpenoid saponins were isolated from Anemone flaccida Fr. Schmidt. Their structures were identified as glycoside St-I4a (1), glycoside St-J (2), anhuienoside E (3), Hederasaponin B (4), and flaccidoside II (5). Compounds 1-2 were isolated from Anemone family for the first time, and compounds 3-4 were isolated from this plant for the first time.
METHODS AND RESULTS:
The inhibitory effects of saponins on proliferation of HeLa cells were studied by MTT assay, the apoptosis-induction activity was observed by cell-cycle analysis and caspase-3 expression assay. The antitumor activities of the saponins were ranked in the following order: 5 > 3 > 4 > 1 > 2.
CONCLUSIONS:
The data presented here indicated that naturally occurring triterpenoid saponins can be regarded as excellent structures for the potential development of new anticancer agents.

Antiperoxidation activity of triterpenoids from rhizome of Anemone raddeana.[Pubmed: 19084054]

Fitoterapia. 2009 Mar;80(2):105-11.

Four triterpenoid compounds hederacolchiside E (1), Hederasaponin B (2), raddeanoside 20 (3) and raddeanoside 21 (4) were isolated from ethanol extracts of rhizome of Anemone raddeana Regel.
METHODS AND RESULTS:
The effects of these triterpenoids on superoxide generation, tyrosyl phosphorylation of proteins and translocation of cytosolic compounds, such as p47(phox), p67(phox) and Rac to the cell membrane in human neutrophils was investigated. The superoxide generation induced by N-formyl-methionyl-leucyl-phenylalanine (fMLP) was slightly suppressed by Hederasaponin B, raddeanoside 20 and raddeanoside 21 in a concentration dependent manner. The superoxide generation induced by arachidonic acid (AA) was suppressed by Hederasaponin B and raddeanoside 21 significantly.
CONCLUSIONS:
fMLP- and AA-induced tyrosyl phosphorylation and translocation of the cytosolic proteins: p47(phox), p67(phox), and Rac to the cell membrane were suppressed in parallel with the suppression of stimulus-induced superoxide generation.

Protocol of Hederasaponin B

Structure Identification
J Chromatogr Sci. 2015 Apr;53(4):478-83.

Determination of saponins and flavonoids in ivy leaf extracts using HPLC-DAD.[Pubmed: 24981979]

A new method for the determination of six compounds, chlorogenic acid, rutin, nicotiflorin, hederacoside C, Hederasaponin B and α-hederin, in ivy leaf extracts using high-performance liquid chromatography with diode array detector was developed.
METHODS AND RESULTS:
The chromatographic separation was performed on a YMC Hydrosphere C18 analytical column using a gradient elution of 0.1% phosphoric acid and acetonitrile. The method was validated in terms of specificity, linearity (r(2) > 0.9999), precision [relative standard deviation (RSD) < 0.36%] and accuracy (97.4-103.8%). The limit of detection and limit of quantification were <20.32 and 61.56 ng for all analytes, respectively. The tested compounds were found to be stable in the ivy leaf extract from 0 to 48 h, and the RSD value for each compound was <0.90%. The validated method was successfully applied to quantify all six compounds in a 30% ethanol ivy leaf extract and 13 ivy leaf extract products.
CONCLUSIONS:
The results showed that all the tested products satisfied the minimum requirement for the content of hederacoside C. However, there were some differences between the contents of other constituents.

Hederasaponin B Dilution Calculator

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Hederasaponin B Molarity Calculator

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Preparing Stock Solutions of Hederasaponin B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.8296 mL 4.148 mL 8.296 mL 16.592 mL 20.74 mL
5 mM 0.1659 mL 0.8296 mL 1.6592 mL 3.3184 mL 4.148 mL
10 mM 0.083 mL 0.4148 mL 0.8296 mL 1.6592 mL 2.074 mL
50 mM 0.0166 mL 0.083 mL 0.1659 mL 0.3318 mL 0.4148 mL
100 mM 0.0083 mL 0.0415 mL 0.083 mL 0.1659 mL 0.2074 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 Hederasaponin B

Triterpenoid saponins from Anemone flaccida induce apoptosis activity in HeLa cells.[Pubmed:19219723]

J Asian Nat Prod Res. 2009;11(2):122-7.

Five triterpenoid saponins were isolated from Anemone flaccida Fr. Schmidt. Their structures were identified as glycoside St-I4a (1), glycoside St-J (2), anhuienoside E (3), Hederasaponin B (4), and flaccidoside II (5). Compounds 1-2 were isolated from Anemone family for the first time, and compounds 3-4 were isolated from this plant for the first time. The inhibitory effects of saponins on proliferation of HeLa cells were studied by MTT assay, the apoptosis-induction activity was observed by cell-cycle analysis and caspase-3 expression assay. The antitumor activities of the saponins were ranked in the following order: 5 > 3 > 4 > 1 > 2. The data presented here indicated that naturally occurring triterpenoid saponins can be regarded as excellent structures for the potential development of new anticancer agents.

Antiperoxidation activity of triterpenoids from rhizome of Anemone raddeana.[Pubmed:19084054]

Fitoterapia. 2009 Mar;80(2):105-11.

Four triterpenoid compounds hederacolchiside E (1), Hederasaponin B (2), raddeanoside 20 (3) and raddeanoside 21 (4) were isolated from ethanol extracts of rhizome of Anemone raddeana Regel. The effects of these triterpenoids on superoxide generation, tyrosyl phosphorylation of proteins and translocation of cytosolic compounds, such as p47(phox), p67(phox) and Rac to the cell membrane in human neutrophils was investigated. The superoxide generation induced by N-formyl-methionyl-leucyl-phenylalanine (fMLP) was slightly suppressed by Hederasaponin B, raddeanoside 20 and raddeanoside 21 in a concentration dependent manner. The superoxide generation induced by arachidonic acid (AA) was suppressed by Hederasaponin B and raddeanoside 21 significantly. fMLP- and AA-induced tyrosyl phosphorylation and translocation of the cytosolic proteins: p47(phox), p67(phox), and Rac to the cell membrane were suppressed in parallel with the suppression of stimulus-induced superoxide generation.

Determination of saponins and flavonoids in ivy leaf extracts using HPLC-DAD.[Pubmed:24981979]

J Chromatogr Sci. 2015 Apr;53(4):478-83.

A new method for the determination of six compounds, chlorogenic acid, rutin, nicotiflorin, hederacoside C, Hederasaponin B and alpha-hederin, in ivy leaf extracts using high-performance liquid chromatography with diode array detector was developed. The chromatographic separation was performed on a YMC Hydrosphere C18 analytical column using a gradient elution of 0.1% phosphoric acid and acetonitrile. The method was validated in terms of specificity, linearity (r(2) > 0.9999), precision [relative standard deviation (RSD) < 0.36%] and accuracy (97.4-103.8%). The limit of detection and limit of quantification were <20.32 and 61.56 ng for all analytes, respectively. The tested compounds were found to be stable in the ivy leaf extract from 0 to 48 h, and the RSD value for each compound was <0.90%. The validated method was successfully applied to quantify all six compounds in a 30% ethanol ivy leaf extract and 13 ivy leaf extract products. The results showed that all the tested products satisfied the minimum requirement for the content of hederacoside C. However, there were some differences between the contents of other constituents.

Antiviral Activity of Hederasaponin B from Hedera helix against Enterovirus 71 Subgenotypes C3 and C4a.[Pubmed:24596620]

Biomol Ther (Seoul). 2014 Jan;22(1):41-6.

Enterovirus 71 (EV71) is the predominant cause of hand, foot and mouth disease (HFMD). The antiviral activity of Hederasaponin B from Hedera helix against EV71 subgenotypes C3 and C4a was evaluated in vero cells. In the current study, the antiviral activity of Hederasaponin B against EV71 C3 and C4a was determined by cytopathic effect (CPE) reduction method and western blot assay. Our results demonstrated that Hederasaponin B and 30% ethanol extract of Hedera helix containing Hederasaponin B showed significant antiviral activity against EV71 subgenotypes C3 and C4a by reducing the formation of a visible CPE. Hederasaponin B also inhibited the viral VP2 protein expression, suggesting the inhibition of viral capsid protein synthesis.These results suggest that Hederasaponin B and Hedera helix extract containing Hederasaponin B can be novel drug candidates with broad-spectrum antiviral activity against various subgenotypes of EV71.

Description

Hederasaponin B, isolated from Hedera helix, has broad-spectrum antiviral activity against various subgenotypes of Enterovirus 71 (EV71).

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