Picroside III

CAS# 64461-95-6

Picroside III

2D Structure

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Picroside III

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Chemical Properties of Picroside III

Cas No. 64461-95-6 SDF Download SDF
PubChem ID 24121289 Appearance White powder
Formula C25H30O13 M.Wt 538.50
Type of Compound Iridoids Storage Desiccate at -20°C
Synonyms 770721-33-0;6-Feruloylcatalpol;6-O-Feruloylcatalpol
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(1aS,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-6-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
SMILES COC1=C(C=CC(=C1)C=CC(=O)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)O
Standard InChIKey RMSKZOXJAHOIER-GGKKSNITSA-N
Standard InChI InChI=1S/C25H30O13/c1-33-14-8-11(2-4-13(14)28)3-5-16(29)36-21-12-6-7-34-23(17(12)25(10-27)22(21)38-25)37-24-20(32)19(31)18(30)15(9-26)35-24/h2-8,12,15,17-24,26-28,30-32H,9-10H2,1H3/b5-3+/t12-,15-,17-,18-,19+,20-,21+,22+,23+,24+,25-/m1/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 Picroside III

The roots of Picrorhiza scrophulariiflora

Biological Activity of Picroside III

DescriptionPicrosides exhibit significant learning and memory deficits, just as Alzheimer's disease(AD) in human.
In vitro

Pipette tip solid-phase extraction and ultra-performance liquid chromatography/mass spectrometry based rapid analysis of picrosides from Picrorhiza scrophulariiflora.[Pubmed: 23567266]

J Pharm Biomed Anal. 2013 Jun;80:136-40.

Pipette tip solid-phase extraction (PT-SPE) is a technique popular in sample preparation of biological fluids and protein hydrolysates.
METHODS AND RESULTS:
In this study, we developed a microtechnic using a pipette tip packed with C18 as sorbent for extraction and purification of bioactive compounds, picroside-I, II and III, in crude herbal extracts from Picrorhiza scrophulariiflora (P. scrophulariiflora). Compared to conventional SPE, PT-SPE is fast, easy to operate, and the tools are very accessible (pipette tip and tube, without expensive SPE set-up). Moreover, it is also cost-effective because significant amount of sorbent and solvents can be saved. The eluate was analyzed by ultra-performance liquid chromatography and tandem mass spectrometry (UPLC-MS/MS). Afterwards, the method was fully validated and the results demonstrated that the PT-SPE-UPLC-MS/MS method is an excellent technique for analysis of the herbal medicine. Finally, this PT-SPE-UPLC-MS/MS strategy was successfully applied to analyze the crude extracts from P. scrophulariiflora samples within 10min (2min for PT-SPE and 8min for UPLC), 3.5mL solvents (including water, 0.3mL for PT-SPE and 3.2mL for UPLC), and 2mg C18 sorbent for each sample.
CONCLUSIONS:
We believe this method to be very practical and, in particular, to be suitable for widespread herbal medicine analysis.

Protocol of Picroside III

Structure Identification
J Sep Sci. 2011 Aug;34(15):1910-6.

Counter-current chromatographic method for preparative scale isolation of picrosides from traditional Chinese medicine Picrorhiza scrophulariiflora.[Pubmed: 21721121]

Apocynin, androsin, together with picroside I, picrosideII and Picroside III from crude extracts of Picrorhiza scrophulariiflora were isolated by means of high-speed counter-current chromatography (CCC) combining elution-extrusion (EE) and cycling-elution (CE) approach. The EECCC took full advantages of the liquid nature of the stationary phase for a complete sample recovery and extended the solute hydrophobicity window, while CECCC showed its unique advantage in achieving effective separation of special compounds through preventing stationary phase loss.
METHODS AND RESULTS:
In the present work, the biphasic liquid system composed of n-hexane/ethyl acetate/methanol/water (1:2:1:2, v/v/v/v) was used for separation of apocynin and androsin, ethyl acetate/n-butanol/water/formic acid (4:1:5:0.005, v/v/v/v) for picroside I,picroside II and Picroside III.However, due to the extremely similar K values (K1 /K2 ≈1.2), picroside I and Picroside III were always eluted together by several biphasic solvent systems. In this case, the CECCC exhibited great superiority and baseline separated in the sixth cycle using ethyl acetate/water (1:1, v/v) as biphasic liquid system.
CONCLUSIONS:
Each fraction was analyzed by UPLC-UV and ESI-MS analysis, and identified by comparing with the data of reference substances. Compared with classical elution, the combination of EE and CE approach exhibits strong separation efficiency and great potential to be a high-throughput separation technique in the case of complex samples.

Picroside III Dilution Calculator

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Preparing Stock Solutions of Picroside III

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.857 mL 9.2851 mL 18.5701 mL 37.1402 mL 46.4253 mL
5 mM 0.3714 mL 1.857 mL 3.714 mL 7.428 mL 9.2851 mL
10 mM 0.1857 mL 0.9285 mL 1.857 mL 3.714 mL 4.6425 mL
50 mM 0.0371 mL 0.1857 mL 0.3714 mL 0.7428 mL 0.9285 mL
100 mM 0.0186 mL 0.0929 mL 0.1857 mL 0.3714 mL 0.4643 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 Picroside III

Pipette tip solid-phase extraction and ultra-performance liquid chromatography/mass spectrometry based rapid analysis of picrosides from Picrorhiza scrophulariiflora.[Pubmed:23567266]

J Pharm Biomed Anal. 2013 Jun;80:136-40.

Pipette tip solid-phase extraction (PT-SPE) is a technique popular in sample preparation of biological fluids and protein hydrolysates. In this study, we developed a microtechnic using a pipette tip packed with C18 as sorbent for extraction and purification of bioactive compounds, picroside-I, II and III, in crude herbal extracts from Picrorhiza scrophulariiflora (P. scrophulariiflora). Compared to conventional SPE, PT-SPE is fast, easy to operate, and the tools are very accessible (pipette tip and tube, without expensive SPE set-up). Moreover, it is also cost-effective because significant amount of sorbent and solvents can be saved. The eluate was analyzed by ultra-performance liquid chromatography and tandem mass spectrometry (UPLC-MS/MS). Afterwards, the method was fully validated and the results demonstrated that the PT-SPE-UPLC-MS/MS method is an excellent technique for analysis of the herbal medicine. Finally, this PT-SPE-UPLC-MS/MS strategy was successfully applied to analyze the crude extracts from P. scrophulariiflora samples within 10min (2min for PT-SPE and 8min for UPLC), 3.5mL solvents (including water, 0.3mL for PT-SPE and 3.2mL for UPLC), and 2mg C18 sorbent for each sample. We believe this method to be very practical and, in particular, to be suitable for widespread herbal medicine analysis.

Counter-current chromatographic method for preparative scale isolation of picrosides from traditional Chinese medicine Picrorhiza scrophulariiflora.[Pubmed:21721121]

J Sep Sci. 2011 Aug;34(15):1910-6.

Apocynin, androsin, together with picroside I, II and III from crude extracts of Picrorhiza scrophulariiflora were isolated by means of high-speed counter-current chromatography (CCC) combining elution-extrusion (EE) and cycling-elution (CE) approach. The EECCC took full advantages of the liquid nature of the stationary phase for a complete sample recovery and extended the solute hydrophobicity window, while CECCC showed its unique advantage in achieving effective separation of special compounds through preventing stationary phase loss. In the present work, the biphasic liquid system composed of n-hexane/ethyl acetate/methanol/water (1:2:1:2, v/v/v/v) was used for separation of apocynin and androsin, ethyl acetate/n-butanol/water/formic acid (4:1:5:0.005, v/v/v/v) for picroside I, II and III. However, due to the extremely similar K values (K1 /K2 approximately 1.2), picroside I and III were always eluted together by several biphasic solvent systems. In this case, the CECCC exhibited great superiority and baseline separated in the sixth cycle using ethyl acetate/water (1:1, v/v) as biphasic liquid system. Each fraction was analyzed by UPLC-UV and ESI-MS analysis, and identified by comparing with the data of reference substances. Compared with classical elution, the combination of EE and CE approach exhibits strong separation efficiency and great potential to be a high-throughput separation technique in the case of complex samples.

Description

Picroside III is an iridoid glycoside isolated from Picrorhiza scrophulariiflora (PS), a traditional Chinese medicine.

Keywords:

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