Pteroside A

CAS# 35910-15-7

Pteroside A

Catalog No. BCN8146----Order now to get a substantial discount!

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Quality Control of Pteroside A

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Chemical structure

Pteroside A

3D structure

Chemical Properties of Pteroside A

Cas No. 35910-15-7 SDF Download SDF
PubChem ID 169727 Appearance Powder
Formula C21H30O8 M.Wt 410.5
Type of Compound Sesquiterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S)-2-(hydroxymethyl)-2,5,7-trimethyl-6-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-3H-inden-1-one
SMILES CC1=C(C(=C2C(=C1)CC(C2=O)(C)CO)C)CCOC3C(C(C(C(O3)CO)O)O)O
Standard InChIKey UTBLUTBCAVVCIO-HPCBLLCTSA-N
Standard InChI InChI=1S/C21H30O8/c1-10-6-12-7-21(3,9-23)19(27)15(12)11(2)13(10)4-5-28-20-18(26)17(25)16(24)14(8-22)29-20/h6,14,16-18,20,22-26H,4-5,7-9H2,1-3H3/t14-,16-,17+,18-,20-,21+/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 Pteroside A

The herbs of Pteris aquilinum

Biological Activity of Pteroside A

In vitro

Chemical and biologically active constituents of Pteris multifida.[Pubmed: 18553125]

J Nat Med. 2008 Oct;62(4):452-5.

A new compound, 4-caffeoyl quinic acid 5-O-methyl ether (2), together with 12 known compounds--identified as (2R,3R)-pterosin L 3-O-beta-D-glucopyrannoside (3), beta-sitosterol beta-D-glucopyranoside (4), apigenin 7-O-beta-D-glucopyranoside (5), luteolin 7-O-beta-D-glucopyranoside (6), sucrose (7), caffeic acid (8), pterosin C 3-O-beta-D-glucopyranoside (9), pteroside C (10), 4,5-dicaffeoyl quinic acid (11), Pteroside A (12), wallichoside (13) and (2S)-5,7,3',5'-tetrahydroxyflavanone (14)--were isolated from Pteris multifida.
METHODS AND RESULTS:
The structure of the new compound was determined by means of physical, chemical and spectroscopic evidence. Compounds 5 and 6 were the main constituents of the plant, with yields of 0.19% and 0.16%, respectively. The cytotoxic activities of 2, 3, and 9-13 were evaluated against a human cell line (KB cells).
CONCLUSIONS:
Among the isolated compounds, pterosin C 3-O-beta-D-glucopyrannoside (9) and 4,5-dicaffeoylquinic acid (11) showed a significant selective cytotoxicity (IC(50) 2.35 and 5.38, respectively), while moderate activity was observed for compound 2 (IC(50) 12.3). The chemosystematics of Pteris species is also discussed.

Protocol of Pteroside A

Structure Identification
Phytochemistry. 2016 Aug;128:82-94.

Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome.[Pubmed: 27177933 ]

Systematic phytochemical investigations of the underground rhizome of Pteridium aquilinum (L.) Kuhn (Dennstaedtiaceae) afforded thirty-five pterosins and pterosides.
METHODS AND RESULTS:
By detailed analysis of one- and two-dimensional nuclear magnetic resonance spectroscopy, circular dichroism (CD) and high-resolution mass spectrometric data, thirteen previously undescribed pterosins and pterosides have been identified. Interestingly, for the first time 12-O-β-D-glucopyranoside substituted pterosins, rhedynosides C and D, and the sulfate-containing pterosin, rhedynosin H, alongside the two known compounds, histiopterosin A and (2S)-Pteroside A2, were isolated from the rhizomes of subsp. aquilinum of bracken. In addition, six-membered cyclic ether pterosins and pterosides, rhedynosin A and rhedynoside A, are the first examples of this type of pterosin-sesquiterpenoid. Additionally, the three previously reported compounds (rhedynosin I, (2S)-2-hydroxymethylpterosin E and (2S)-12-hydroxypterosin A) were obtained for the first time from plants as opposed to mammalian metabolic products. Single crystal X-ray diffraction analysis was applied to the previously undescribed compounds (2R)-rhedynoside B, (2R)-pteroside B and (2S)-pteroside K, yielding the first crystal structures for pterosides, and three known pterosins, (2S)-pterosin A, trans-pterosin C and cis-pterosin C. Rhedynosin C is the only example of the cyclic lactone pterosins with a keto group at position C-14.
CONCLUSIONS:
Six selected pterosins ((2S)-pterosin A, (2R)-pterosin B and trans-pterosin C) and associated glycosides ((2S)-Pteroside A, (2R)-pteroside B and pteroside Z) were assessed for their anti-diabetic activity using an intestinal glucose uptake assay; all were found to be inactive at 300 μM.

Pteroside A Dilution Calculator

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Pteroside A Molarity Calculator

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Preparing Stock Solutions of Pteroside A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4361 mL 12.1803 mL 24.3605 mL 48.7211 mL 60.9013 mL
5 mM 0.4872 mL 2.4361 mL 4.8721 mL 9.7442 mL 12.1803 mL
10 mM 0.2436 mL 1.218 mL 2.4361 mL 4.8721 mL 6.0901 mL
50 mM 0.0487 mL 0.2436 mL 0.4872 mL 0.9744 mL 1.218 mL
100 mM 0.0244 mL 0.1218 mL 0.2436 mL 0.4872 mL 0.609 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 Pteroside A

Isolation and characterisation of 13 pterosins and pterosides from bracken (Pteridium aquilinum (L.) Kuhn) rhizome.[Pubmed:27177933]

Phytochemistry. 2016 Aug;128:82-94.

Systematic phytochemical investigations of the underground rhizome of Pteridium aquilinum (L.) Kuhn (Dennstaedtiaceae) afforded thirty-five pterosins and pterosides. By detailed analysis of one- and two-dimensional nuclear magnetic resonance spectroscopy, circular dichroism (CD) and high-resolution mass spectrometric data, thirteen previously undescribed pterosins and pterosides have been identified. Interestingly, for the first time 12-O-beta-D-glucopyranoside substituted pterosins, rhedynosides C and D, and the sulfate-containing pterosin, rhedynosin H, alongside the two known compounds, histiopterosin A and (2S)-Pteroside A2, were isolated from the rhizomes of subsp. aquilinum of bracken. In addition, six-membered cyclic ether pterosins and pterosides, rhedynosin A and rhedynoside A, are the first examples of this type of pterosin-sesquiterpenoid. Additionally, the three previously reported compounds (rhedynosin I, (2S)-2-hydroxymethylpterosin E and (2S)-12-hydroxypterosin A) were obtained for the first time from plants as opposed to mammalian metabolic products. Single crystal X-ray diffraction analysis was applied to the previously undescribed compounds (2R)-rhedynoside B, (2R)-pteroside B and (2S)-pteroside K, yielding the first crystal structures for pterosides, and three known pterosins, (2S)-pterosin A, trans-pterosin C and cis-pterosin C. Rhedynosin C is the only example of the cyclic lactone pterosins with a keto group at position C-14. Six selected pterosins ((2S)-pterosin A, (2R)-pterosin B and trans-pterosin C) and associated glycosides ((2S)-Pteroside A, (2R)-pteroside B and pteroside Z) were assessed for their anti-diabetic activity using an intestinal glucose uptake assay; all were found to be inactive at 300 muM.

Chemical and biologically active constituents of Pteris multifida.[Pubmed:18553125]

J Nat Med. 2008 Oct;62(4):452-5.

A new compound, 4-caffeoyl quinic acid 5-O-methyl ether (2), together with 12 known compounds--identified as (2R,3R)-pterosin L 3-O-beta-D-glucopyrannoside (3), beta-sitosterol beta-D-glucopyranoside (4), apigenin 7-O-beta-D-glucopyranoside (5), luteolin 7-O-beta-D-glucopyranoside (6), sucrose (7), caffeic acid (8), pterosin C 3-O-beta-D-glucopyranoside (9), pteroside C (10), 4,5-dicaffeoyl quinic acid (11), Pteroside A (12), wallichoside (13) and (2S)-5,7,3',5'-tetrahydroxyflavanone (14)--were isolated from Pteris multifida. The structure of the new compound was determined by means of physical, chemical and spectroscopic evidence. Compounds 5 and 6 were the main constituents of the plant, with yields of 0.19% and 0.16%, respectively. The cytotoxic activities of 2, 3, and 9-13 were evaluated against a human cell line (KB cells). Among the isolated compounds, pterosin C 3-O-beta-D-glucopyrannoside (9) and 4,5-dicaffeoylquinic acid (11) showed a significant selective cytotoxicity (IC(50) 2.35 and 5.38, respectively), while moderate activity was observed for compound 2 (IC(50) 12.3). The chemosystematics of Pteris species is also discussed.

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