Polygalacic acid

CAS# 22338-71-2

Polygalacic acid

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Quality Control of Polygalacic acid

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Chemical structure

Polygalacic acid

3D structure

Chemical Properties of Polygalacic acid

Cas No. 22338-71-2 SDF Download SDF
PubChem ID 161388 Appearance Powder
Formula C30H48O6 M.Wt 504.71
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (4aR,5R,6aR,6aS,6bR,9R,10R,11S,12aR,14bR)-5,10,11-trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
SMILES CC1(CCC2(C(C1)C3=CCC4C(C3(CC2O)C)(CCC5C4(CC(C(C5(C)CO)O)O)C)C)C(=O)O)C
Standard InChIKey KGGGRGBDMBZXKF-KZMOAHQXSA-N
Standard InChI InChI=1S/C30H48O6/c1-25(2)11-12-30(24(35)36)18(13-25)17-7-8-21-26(3)14-19(32)23(34)27(4,16-31)20(26)9-10-28(21,5)29(17,6)15-22(30)33/h7,18-23,31-34H,8-16H2,1-6H3,(H,35,36)/t18-,19+,20?,21-,22-,23+,26+,27+,28-,29-,30-/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 Polygalacic acid

The root of Polygala tenuifolia Willd.

Biological Activity of Polygalacic acid

DescriptionPolygalacic acid may exert a significant neuroprotective effect on cognitive impairment, driven in part by the modulation of cholinergic activity and neuroinflammation. Polygalacic acid shows significant postingestive effects on Spodoptera littoralis larvae.
TargetsAChR | Immunology & Inflammation related
In vitro

Antiproliferative effects of saponins from the roots of Platycodon grandiflorum on cultured human tumor cells.[Pubmed: 20939516]

J Nat Prod. 2010 Nov 29;73(11):1863-7.


METHODS AND RESULTS:
Three new triterpenoid saponins, platyconic acid B lactone (1), deapio-platyconic acid B lactone (2), and deapio-platycodin D(2) (3), together with 17 known triterpenoid saponins, were isolated from a root extract of Platycodon grandiflorum. The structures of 1-3 were determined on the basis of spectroscopic data interpretation and chemical transformation.
CONCLUSIONS:
Saponins with a platycodigenin or Polygalacic acid unit as a sapogenin demonstrated significant inhibitory effects on the proliferation of a small panel of cultured human tumor cells.

Bioactive saponins from Microsechium helleri and Sicyos bulbosus.[Pubmed: 21439597 ]

Phytochemistry. 2011 Jun;72(8):743-51.

Eleven oleanane-type saponins (1-11) have been isolated from Microsechium helleri and Sicyos bulbosus roots and were evaluated for their antifeedant, nematicidal and phytotoxic activities.
METHODS AND RESULTS:
Saponins {3-O-β-D-glucopyranosyl (1→3)-β-D-glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-oic acid 28-O-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside} (1), and {3-O-β-D-glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-oic acid 28-O-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside} (2) were also isolated from M. helleri roots together with the two known compounds 3 and 4. Seven known structurally related saponins (5-11) were isolated from S. bulbosus roots. The structures of these compounds were established as bayogenin and polygalacic glycosides using one- and two-dimensional NMR spectroscopy and mass spectrometry. Compounds 7, 10, bayogenin (12) and Polygalacic acid (13) showed significant (p<0.05) postingestive effects on Spodoptera littoralis larvae, compounds 5-11 and 12 showed variable nematicidal effects on Meloydogyne javanica and all tested saponins had variable phytotoxic effects on several plant species (Lycopersicum esculentum, Lolium perenne and Lactuca sativa).
CONCLUSIONS:
These are promising results in the search for natural pesticides from the Cucurbitaceae family.

In vivo

Neuroprotective effects of polygalacic acid on scopolamine-induced memory deficits in mice.[Pubmed: 26926176 ]

Phytomedicine. 2016 Feb 15;23(2):149-55.

Polygala tenuifolia Willd is a Traditional Chinese Medicine used for the treatment of learning and memory deficits.
METHODS AND RESULTS:
Triterpenoid saponins, the main bioactive compounds of Polygala tenuifolia Willd, are easily hydrolyzed to Polygalacic acid (PA).Treatment with scopolamine significantly increased the escape latency time, decreased the number of crossings, and shortened the time spent in the target quadrant, while PA reversed these scopolamine-induced effects. PA significantly improved cholinergic system reactivity, as indicated by decreased acetylcholinesterase (AChE) activity, increased choline acetyltransferase (ChAT) activity, and elevated levels of acetylcholine (ACh) in the hippocampus and frontal cortex. PA also significantly ameliorated neuroinflammation and oxidative stress in mice.
CONCLUSIONS:
These results suggest that PA might exert a significant neuroprotective effect on cognitive impairment, driven in part by the modulation of cholinergic activity and neuroinflammation.

Polygalacic acid Dilution Calculator

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Polygalacic acid Molarity Calculator

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Preparing Stock Solutions of Polygalacic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.9813 mL 9.9067 mL 19.8134 mL 39.6267 mL 49.5334 mL
5 mM 0.3963 mL 1.9813 mL 3.9627 mL 7.9253 mL 9.9067 mL
10 mM 0.1981 mL 0.9907 mL 1.9813 mL 3.9627 mL 4.9533 mL
50 mM 0.0396 mL 0.1981 mL 0.3963 mL 0.7925 mL 0.9907 mL
100 mM 0.0198 mL 0.0991 mL 0.1981 mL 0.3963 mL 0.4953 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 Polygalacic acid

Bioactive saponins from Microsechium helleri and Sicyos bulbosus.[Pubmed:21439597]

Phytochemistry. 2011 Jun;72(8):743-51.

Eleven oleanane-type saponins (1-11) have been isolated from Microsechium helleri and Sicyos bulbosus roots and were evaluated for their antifeedant, nematicidal and phytotoxic activities. Saponins {3-O-beta-D-glucopyranosyl (1-->3)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-o ic acid 28-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta-D-xylopyr anosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside} (1), and {3-O-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta-D-xylopyr anosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside} (2) were also isolated from M. helleri roots together with the two known compounds 3 and 4. Seven known structurally related saponins (5-11) were isolated from S. bulbosus roots. The structures of these compounds were established as bayogenin and polygalacic glycosides using one- and two-dimensional NMR spectroscopy and mass spectrometry. Compounds 7, 10, bayogenin (12) and Polygalacic acid (13) showed significant (p<0.05) postingestive effects on Spodoptera littoralis larvae, compounds 5-11 and 12 showed variable nematicidal effects on Meloydogyne javanica and all tested saponins had variable phytotoxic effects on several plant species (Lycopersicum esculentum, Lolium perenne and Lactuca sativa). These are promising results in the search for natural pesticides from the Cucurbitaceae family.

Neuroprotective effects of polygalacic acid on scopolamine-induced memory deficits in mice.[Pubmed:26926176]

Phytomedicine. 2016 Feb 15;23(2):149-55.

BACKGROUND: Polygala tenuifolia Willd is a Traditional Chinese Medicine used for the treatment of learning and memory deficits. Triterpenoid saponins, the main bioactive compounds of Polygala tenuifolia Willd, are easily hydrolyzed to Polygalacic acid (PA). PURPOSE: The present study was undertaken to investigate the neuroprotective effects of PA on scopolamine-induced cognitive dysfunction and to elucidate its underlying mechanisms of action. METHODS: PA (3, 6, and 12 mg/kg) was administered orally to mice for fourteen days, and scopolamine (1 mg/kg) was injected intraperitoneally for fourteen days to induce memory impairment. Memory-related behaviors were evaluated using the Morris water maze. Cholinergic and neuroinflammatory activities were measured in brain tissue. Superoxide dismutase activities, malondialdehyde and reduced glutathione contents were also measured in the brains. RESULTS: Treatment with scopolamine significantly increased the escape latency time, decreased the number of crossings, and shortened the time spent in the target quadrant, while PA reversed these scopolamine-induced effects. PA significantly improved cholinergic system reactivity, as indicated by decreased acetylcholinesterase (AChE) activity, increased choline acetyltransferase (ChAT) activity, and elevated levels of acetylcholine (ACh) in the hippocampus and frontal cortex. PA also significantly ameliorated neuroinflammation and oxidative stress in mice. CONCLUSION: These results suggest that PA might exert a significant neuroprotective effect on cognitive impairment, driven in part by the modulation of cholinergic activity and neuroinflammation.

Antiproliferative effects of saponins from the roots of Platycodon grandiflorum on cultured human tumor cells.[Pubmed:20939516]

J Nat Prod. 2010 Nov 29;73(11):1863-7.

Three new triterpenoid saponins, platyconic acid B lactone (1), deapio-platyconic acid B lactone (2), and deapio-platycodin D(2) (3), together with 17 known triterpenoid saponins, were isolated from a root extract of Platycodon grandiflorum. The structures of 1-3 were determined on the basis of spectroscopic data interpretation and chemical transformation. Saponins with a platycodigenin or Polygalacic acid unit as a sapogenin demonstrated significant inhibitory effects on the proliferation of a small panel of cultured human tumor cells.

Description

Polygalacic acid, is a triterpene, isolated from the root of Polygala tenuifolia Willd. Polygalacic acid inhibits MMP expression. Polygalacic acid may have a therapeutic effect in Osteoarthritis (OA) treatment . Polygalacic acid exerts a significant neuroprotective effect on cognitive impairment, PA improves cholinergic system reactivity by inhibiting acetylcholinesterase (AChE) activity, increasing choline acetyltransferase (ChAT) activity, and elevating levels of acetylcholine (Ach) in the hippocampus and frontal cortex.

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