Phytolaccagenin

CAS# 1802-12-6

Phytolaccagenin

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Quality Control of Phytolaccagenin

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Chemical structure

Phytolaccagenin

3D structure

Chemical Properties of Phytolaccagenin

Cas No. 1802-12-6 SDF Download SDF
PubChem ID 272184 Appearance White powder
Formula C31H48O7 M.Wt 532.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms Jaligonic acid 30-methyl ester
Solubility Soluble in methan
Chemical Name 10,11-dihydroxy-9-(hydroxymethyl)-2-methoxycarbonyl-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
SMILES CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)CO)O)O)C)C)C2C1)C)C(=O)O)C(=O)OC
Standard InChIKey CYJWWQALTIKOAG-UHFFFAOYSA-N
Standard InChI InChI=1S/C31H48O7/c1-26(25(37)38-6)11-13-31(24(35)36)14-12-29(4)18(19(31)15-26)7-8-22-27(2)16-20(33)23(34)28(3,17-32)21(27)9-10-30(22,29)5/h7,19-23,32-34H,8-17H2,1-6H3,(H,35,36)
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 Phytolaccagenin

The roots of Phytolacca acinosa Roxb

Biological Activity of Phytolaccagenin

DescriptionPhytolaccagenin has promising antifungal activity against ATCC standard cultures of Candida albicans and Cryptococcus neoformans, and against clinical isolates of these fungi, it also shows inhibitory effects on lipopolysaccharide-induced NO production, and haemolytic activities.
TargetsAntifection | NO
In vitro

Antifungal activity of saponin-rich extracts of Phytolacca dioica and of the sapogenins obtained through hydrolysis.[Pubmed: 20734930]

Nat. Prod. Commun.,2010, 5(7):1013-8.


METHODS AND RESULTS:
A saponin-rich extract of Phytolacca dioica L. berries, its acid hydrolysate, and its major aglycone, Phytolaccagenin, were assayed for antifungal activity against ATCC standard cultures of Candida albicans and Cryptococcus neoformans, and against clinical isolates of these fungi. The activity of the extract was either low or negligible, but the hydrolysate, containing the sapogenins, including Phytolaccagenin, and also pure Phytolaccagenin, showed promising antifungal potency.
CONCLUSIONS:
Hydrolysis of a natural product extract is shown to be a useful modification leading to improved bioactivity.

Protocol of Phytolaccagenin

Structure Identification
J Pharm Biomed Anal. 2015 Mar 25;107:82-8.

Development and validation of a HPLC-MS/MS method for the determination of phytolaccagenin in rat plasma and application to a pharmacokinetic study.[Pubmed: 25575173]

Radix Phytolaccae (the dried root of Phytolacca acinosa Roxb. or Phytolacca americana L.) is widely used in East Asian countries for the treatment of inflammation-related diseases. The active component of Radix Phtolaccae is Phytolcaccagenin a triterpenoid saponin. Phytolcaccagenin has anti-inflammatory activities that exceed those of Esculentoside A and its derivatives regarding suppression of LPS-induced inflammation, and has a lower toxicity profile with less hemolysis. To date, no information is available about analytical method and pharmacokinetic studies of Phytolaccagenin.
METHODS AND RESULTS:
To explore PK profile of this compound, a HPLC-MS/MS assay of Phytolaccagenin in rat plasma was developed and validated. The method was fully validated according to FDA Guidance for industry. The detection was performed by a triple-quadrupole tandem mass spectrometer with multiple reactions monitoring (MRM) in positive ion mode via electrospray ionization. The monitored transitions were m/z 533.2>515.3 for Phytolcaccagenin, and 491.2>473.2 for I.S. The analysis was performed on a Symmetry C18 column (4.6 mm × 50 mm, 3.5 μm) using gradient elution with the mobile phase consisting of acetonitrile and 0.1% formic acid water at a flow rate of 1 ml/min with a 1:1 splitter ratio. The method was validated with a LLOQ of 20 ng/ml and an ULOQ of 1000 ng/ml. The response versus concentration data were fitted with 1/x weighting and the correlation coefficient (r) were greater than 0.999. The average matrix effect and the average extraction recovery were acceptable. This validation in rat plasma demonstrated that Phytolaccagenin was stable for 30 days when stored below -20°C, for 6h at room temperature (RT, 22°C), for 12 h at RT for prepared control samples in auto-sampler vials, and during three successive freeze/thaw cycles results at -20°C.
CONCLUSIONS:
The validated method has been successfully applied to an intravenous bolus pharmacokinetic study of Phytolaccagenin in male Sprague-Dawley rats (10 mg/kg, i.v.). Blood samples taken from 0 to 24h after injection were collected, and data analyzed with WinNonlin. The half-life and clearance were 1.4±0.9 h and 2.1±1.1 L/h/kg, respectively.

Phytolaccagenin Dilution Calculator

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Phytolaccagenin Molarity Calculator

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Preparing Stock Solutions of Phytolaccagenin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.8772 mL 9.3861 mL 18.7723 mL 37.5446 mL 46.9307 mL
5 mM 0.3754 mL 1.8772 mL 3.7545 mL 7.5089 mL 9.3861 mL
10 mM 0.1877 mL 0.9386 mL 1.8772 mL 3.7545 mL 4.6931 mL
50 mM 0.0375 mL 0.1877 mL 0.3754 mL 0.7509 mL 0.9386 mL
100 mM 0.0188 mL 0.0939 mL 0.1877 mL 0.3754 mL 0.4693 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 Phytolaccagenin

Antifungal activity of saponin-rich extracts of Phytolacca dioica and of the sapogenins obtained through hydrolysis.[Pubmed:20734930]

Nat Prod Commun. 2010 Jul;5(7):1013-8.

A saponin-rich extract of Phytolacca dioica L. berries, its acid hydrolysate, and its major aglycone, Phytolaccagenin, were assayed for antifungal activity against ATCC standard cultures of Candida albicans and Cryptococcus neoformans, and against clinical isolates of these fungi. The activity of the extract was either low or negligible, but the hydrolysate, containing the sapogenins, including Phytolaccagenin, and also pure Phytolaccagenin, showed promising antifungal potency. Hydrolysis of a natural product extract is shown to be a useful modification leading to improved bioactivity.

Development and validation of a HPLC-MS/MS method for the determination of phytolaccagenin in rat plasma and application to a pharmacokinetic study.[Pubmed:25575173]

J Pharm Biomed Anal. 2015 Mar 25;107:82-8.

Radix Phytolaccae (the dried root of Phytolacca acinosa Roxb. or Phytolacca americana L.) is widely used in East Asian countries for the treatment of inflammation-related diseases. The active component of Radix Phtolaccae is Phytolcaccagenin a triterpenoid saponin. Phytolcaccagenin has anti-inflammatory activities that exceed those of Esculentoside A and its derivatives regarding suppression of LPS-induced inflammation, and has a lower toxicity profile with less hemolysis. To date, no information is available about analytical method and pharmacokinetic studies of Phytolaccagenin. To explore PK profile of this compound, a HPLC-MS/MS assay of Phytolaccagenin in rat plasma was developed and validated. The method was fully validated according to FDA Guidance for industry. The detection was performed by a triple-quadrupole tandem mass spectrometer with multiple reactions monitoring (MRM) in positive ion mode via electrospray ionization. The monitored transitions were m/z 533.2>515.3 for Phytolcaccagenin, and 491.2>473.2 for I.S. The analysis was performed on a Symmetry C18 column (4.6 mm x 50 mm, 3.5 mum) using gradient elution with the mobile phase consisting of acetonitrile and 0.1% formic acid water at a flow rate of 1 ml/min with a 1:1 splitter ratio. The method was validated with a LLOQ of 20 ng/ml and an ULOQ of 1000 ng/ml. The response versus concentration data were fitted with 1/x weighting and the correlation coefficient (r) were greater than 0.999. The average matrix effect and the average extraction recovery were acceptable. This validation in rat plasma demonstrated that Phytolaccagenin was stable for 30 days when stored below -20 degrees C, for 6h at room temperature (RT, 22 degrees C), for 12 h at RT for prepared control samples in auto-sampler vials, and during three successive freeze/thaw cycles results at -20 degrees C. The validated method has been successfully applied to an intravenous bolus pharmacokinetic study of Phytolaccagenin in male Sprague-Dawley rats (10 mg/kg, i.v.). Blood samples taken from 0 to 24h after injection were collected, and data analyzed with WinNonlin. The half-life and clearance were 1.4+/-0.9 h and 2.1+/-1.1 L/h/kg, respectively.

Synthesis of novel derivatives of esculentoside A and its aglycone phytolaccagenin, and evaluation of their haemolytic activity and inhibition of lipopolysaccharide-induced nitric oxide production.[Pubmed:22006712]

Chem Biodivers. 2011 Oct;8(10):1833-52.

A series of 46 compounds derived from esculentoside A and its aglycone were synthesized and characterized. The effect of these compounds on lipopolysaccharide (LPS)-induced NO production, haemolytic activity, and cell viability was evaluated. Structure-activity relationship was established by comparing the derivatives of esculentoside A with its aglycone derivatives. Both the aglycone and its derivatives showed higher inhibitory effects on LPS-induced NO production, and lower haemolytic activities than esculentoside A and its derivatives.

Description

Phytolaccagenin, a triterpenoid saponin, is the active component of Radix Phytolaccae. Phytolcaccagenin has antifungal activity, anti-inflammatory activity and lower toxicity

Keywords:

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