Pedunculoside

CAS# 42719-32-4

Pedunculoside

Catalog No. BCN1191----Order now to get a substantial discount!

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Quality Control of Pedunculoside

Number of papers citing our products

Chemical structure

Pedunculoside

3D structure

Chemical Properties of Pedunculoside

Cas No. 42719-32-4 SDF Download SDF
PubChem ID 14286954 Appearance White powder
Formula C36H58O10 M.Wt 650.84
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms Peduncloside
Solubility Soluble in methanol and pyridine
Chemical Name [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-1,10-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
SMILES CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)O)C)C)C2C1(C)O)C)C(=O)OC6C(C(C(C(O6)CO)O)O)O
Standard InChIKey LARPFJIXBULVPK-FBAXZNBGSA-N
Standard InChI InChI=1S/C36H58O10/c1-19-9-14-36(30(43)46-29-27(42)26(41)25(40)21(17-37)45-29)16-15-33(4)20(28(36)35(19,6)44)7-8-23-31(2)12-11-24(39)32(3,18-38)22(31)10-13-34(23,33)5/h7,19,21-29,37-42,44H,8-18H2,1-6H3/t19-,21-,22-,23-,24+,25-,26+,27-,28-,29+,31+,32+,33-,34-,35-,36+/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 Pedunculoside

The barks of Ilex rotunda Thunb.

Biological Activity of Pedunculoside

DescriptionPedunculoside shows significant hypocholesterolemic and anti-inflammatory activities, it shows potential nitric oxide inhibitory activities with the IC50 value ranging from 14.92 uM to 52.23 uM.
TargetsNO
In vitro

Inhibitory activity of chemical constituents from Arenaria serpyllifolia on nitric oxide production.[Pubmed: 23670630]

Planta Med. 2013 May;79(8):687-92.

Five new compounds, including one new xanthone, 1-hydroxy-5-methoxyxanthone 6-O-β-D-glucopyranoside (1), one new lignan, 3-(β-D-glucopyranosyloxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-acetoxypropyl)-7-methoxy-(2R,3S)-dihydrobenzofuran (2), and three new γ-pyrones, japonicumone A 4'-O-β-D-glucopyranoside (3), japonicumone B 3'-O-β-D-glucopyranoside (4), and japonicumone B 4'-O-β-D-glucopyranoside (5), together with eight known compounds (6-13) were isolated from the whole plants of Arenaria serpyllifolia.
METHODS AND RESULTS:
Their structures were elucidated on the basis of extensive spectroscopic analysis (UV, IR, HRESIMS, 1D- and 2D-NMR, and CD) as well as chemical methods. The isolated compounds were evaluated for their inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW 264.7 macrophages. Compounds 1-5, sacranoside A (9), and Pedunculoside (13) showed potential nitric oxide inhibitory activities with IC50 values ranging from 14.92 µM to 52.23 µM.

In vivo

Hypolipidemic Activity of Pedunculoside, A Constituent of Ilex doniana.[Reference: WebLink]

Pharm. Biol.,1999, 37(1):37- 41.

Pedunculoside, an ester glucoside of 3ß, 19a, 23-trihydroxyurs-12-en-28-oic acid, was isolated from the leaves of Ilex doniana DC. On dietary administration to hyperlipidemic albino rats, it showed significant hypocholesterolemic activity.

Protocol of Pedunculoside

Structure Identification
PLoS One. 2014 Jul 11;9(7):e101761.

A water-soluble inclusion complex of pedunculoside with the polymer β-cyclodextrin: a novel anti-inflammation agent with low toxicity.[Pubmed: 25013908]

More than 50% of new drug candidates in drug discovery are lipophilic and exhibit poor aqueous solubility, which results in poor bioavailability and a lack of dose proportionality.
METHODS AND RESULTS:
Here, we improved the solubility of Pedunculoside (PE) by generating a water-soluble inclusion complex composed of PE and the polymer β-cyclodextrin (CDP). We characterized this novel complex by 1H NMR, FT-IR, UV-vis spectroscopy, powder X-ray diffractometry and thermogravimetric analysis. The ratio of β-cyclodextrin (β-CD) units in CDP to PE was determined to be 2∶1. The KD value of the inclusion complex was determined to be 4.29×10(-3) mol•L(-1). In contrast to the low solubility of PE, the water-solubility of the PE-CDP complex was greatly enhanced. A preclinical toxicological study indicated that PE-CDP was well tolerated for a single administration. Importantly, the anti-inflammation potency of the PE-CDP complex was higher than that of PE.
CONCLUSIONS:
As a result, the formation of inclusion complexes by water-soluble CDP opens up possible aqueous applications of insoluble drug candidates in drug delivery.

J Liq Chromatogr Relat Technol. 2014 Feb 1;37(4):572-587.

Enrichment and purification of pedunculoside and syringin from the barks of Ilex rotunda with macroporous resins.[Pubmed: 25104900]

Jiubiying, the dried barks of Ilex rotunda Thunb. (Aquifoliaceae), has been used as herbal tea and traditional Chinese medicine for heat-clearing, detoxifying, dehumidification, and odynolysis. Pedunculoside and syringin are two main bioactive components.
METHODS AND RESULTS:
For the new drug development, we tried to isolate and purify several chemical constituents from Jiubiying by high-speed counter-current chromatography (HSCCC). The two-phase solvent system used was composed of ethyl acetate-n-butanol-water (1:6:7, v/v/v). From 1.0 g of Jiubiying extracts syringaresinol 4',4″-bis-O-β-D- glucopyranoside (I, 20.2 mg), syringin (II, 56.8 mg), sinapaldehyde glucoside (III, 26.2 mg), syringaresinol 4'-O-β-D-glucopyranoside (IV, 20.4 mg), and Pedunculoside (V, 45.1 mg) were obtained by one run of TBE-1000A HSCCC machine with 1000 mL of column volume.
CONCLUSIONS:
Their structures were identified by IR, MS, and extensive NMR studies. Syringaresinol 4',4″-bis-O-β-D-glucopyranoside (I) was isolated from this plant for the first time.

Pedunculoside Dilution Calculator

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Pedunculoside Molarity Calculator

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Preparing Stock Solutions of Pedunculoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.5365 mL 7.6824 mL 15.3648 mL 30.7295 mL 38.4119 mL
5 mM 0.3073 mL 1.5365 mL 3.073 mL 6.1459 mL 7.6824 mL
10 mM 0.1536 mL 0.7682 mL 1.5365 mL 3.073 mL 3.8412 mL
50 mM 0.0307 mL 0.1536 mL 0.3073 mL 0.6146 mL 0.7682 mL
100 mM 0.0154 mL 0.0768 mL 0.1536 mL 0.3073 mL 0.3841 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 Pedunculoside

Enrichment and purification of pedunculoside and syringin from the barks of Ilex rotunda with macroporous resins.[Pubmed:25104900]

J Liq Chromatogr Relat Technol. 2014 Feb 1;37(4):572-587.

Jiubiying, the dried barks of Ilex rotunda Thunb. (Aquifoliaceae), has been used as herbal tea and traditional Chinese medicine for heat-clearing, detoxifying, dehumidification, and odynolysis. Pedunculoside and syringin are two main bioactive components. For the new drug development, we tried to isolate and purify several chemical constituents from Jiubiying by high-speed counter-current chromatography (HSCCC). The two-phase solvent system used was composed of ethyl acetate-n-butanol-water (1:6:7, v/v/v). From 1.0 g of Jiubiying extracts syringaresinol 4',4''-bis-O-beta-D- glucopyranoside (I, 20.2 mg), syringin (II, 56.8 mg), sinapaldehyde glucoside (III, 26.2 mg), syringaresinol 4'-O-beta-D-glucopyranoside (IV, 20.4 mg), and Pedunculoside (V, 45.1 mg) were obtained by one run of TBE-1000A HSCCC machine with 1000 mL of column volume. Their structures were identified by IR, MS, and extensive NMR studies. Syringaresinol 4',4''-bis-O-beta-D-glucopyranoside (I) was isolated from this plant for the first time.

Inhibitory activity of chemical constituents from Arenaria serpyllifolia on nitric oxide production.[Pubmed:23670630]

Planta Med. 2013 May;79(8):687-92.

Five new compounds, including one new xanthone, 1-hydroxy-5-methoxyxanthone 6-O-beta-D-glucopyranoside (1), one new lignan, 3-(beta-D-glucopyranosyloxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-acetoxyprop yl)-7-methoxy-(2R,3S)-dihydrobenzofuran (2), and three new gamma-pyrones, japonicumone A 4'-O-beta-D-glucopyranoside (3), japonicumone B 3'-O-beta-D-glucopyranoside (4), and japonicumone B 4'-O-beta-D-glucopyranoside (5), together with eight known compounds (6-13) were isolated from the whole plants of Arenaria serpyllifolia. Their structures were elucidated on the basis of extensive spectroscopic analysis (UV, IR, HRESIMS, 1D- and 2D-NMR, and CD) as well as chemical methods. The isolated compounds were evaluated for their inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW 264.7 macrophages. Compounds 1-5, sacranoside A (9), and Pedunculoside (13) showed potential nitric oxide inhibitory activities with IC50 values ranging from 14.92 microM to 52.23 microM.

A water-soluble inclusion complex of pedunculoside with the polymer beta-cyclodextrin: a novel anti-inflammation agent with low toxicity.[Pubmed:25013908]

PLoS One. 2014 Jul 11;9(7):e101761.

More than 50% of new drug candidates in drug discovery are lipophilic and exhibit poor aqueous solubility, which results in poor bioavailability and a lack of dose proportionality. Here, we improved the solubility of Pedunculoside (PE) by generating a water-soluble inclusion complex composed of PE and the polymer beta-cyclodextrin (CDP). We characterized this novel complex by 1H NMR, FT-IR, UV-vis spectroscopy, powder X-ray diffractometry and thermogravimetric analysis. The ratio of beta-cyclodextrin (beta-CD) units in CDP to PE was determined to be 2ratio1. The KD value of the inclusion complex was determined to be 4.29x10(-3) mol*L(-1). In contrast to the low solubility of PE, the water-solubility of the PE-CDP complex was greatly enhanced. A preclinical toxicological study indicated that PE-CDP was well tolerated for a single administration. Importantly, the anti-inflammation potency of the PE-CDP complex was higher than that of PE. As a result, the formation of inclusion complexes by water-soluble CDP opens up possible aqueous applications of insoluble drug candidates in drug delivery.

Description

Pedunculoside is a main bioactive component isolated from Jiubiying. Pedunculoside exerts lipid-lowering effects partly through the regulation of lipogenesis and fatty acid β-oxidation.

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