Scandoside

CAS# 18842-99-4

Scandoside

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Chemical structure

Scandoside

3D structure

Chemical Properties of Scandoside

Cas No. 18842-99-4 SDF Download SDF
PubChem ID 21602023 Appearance Powder
Formula C16H22O11 M.Wt 390.3
Type of Compound Iridoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1S,4aS,5R,7aS)-5-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
SMILES C1=C(C2C(C1O)C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)CO
Standard InChIKey ZVXWFPTVHBWJOU-AWQYILTISA-N
Standard InChI InChI=1S/C16H22O11/c17-2-5-1-7(19)10-6(14(23)24)4-25-15(9(5)10)27-16-13(22)12(21)11(20)8(3-18)26-16/h1,4,7-13,15-22H,2-3H2,(H,23,24)/t7-,8-,9-,10+,11-,12+,13-,15+,16+/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 Scandoside

The herbs of Paederia scandens (Lour.) Merr

Biological Activity of Scandoside

DescriptionScandoside exerts anti-inflammatory effect via suppressing NF-κB and MAPK signaling pathways in LPS-induced RAW 264.7 macrophages.It also inhibits LDL-oxidation.
TargetsMAPK | NF-κB
In vitro

Iridoid glycosides isolated from Oldenlandia diffusa inhibit LDL-oxidation.[Reference: WebLink]

Archives of Pharmacal Research, 2005, 28(10):1156-1160.


METHODS AND RESULTS:
An iridoid glycoside, oldenlandoside III ( 5 ) was isolated from the n -butanol fraction of methanol extracts of the aerial parts of Oldenlandia diffusa Roxb, along with six others previously characterized iridoid glycosides; geniposidic acid ( 1 ), Scandoside ( 2 ), feretoside ( 3 ), 10- O -benzoylScandoside methyl ester ( 4 ), asperulosidic acid ( 6 ) and deacetylasperulosidic acid ( 7 ).
CONCLUSIONS:
Compounds 1, 2 , and 7 inhibited LDL-oxidation, and showed 63.3±2.0, 62.2±1.6, and 63.8±1.5% inhibition, respectively, at a concentration of 20 μg/mL.

Iridoid glucosides with insecticidal activity from Galium melanantherum.[Reference: WebLink]

Zeitschrift für Naturforschung C, 2007, 62(7-8):597---602.

The insecticidal activity of the endemic species Galium melanantherum was evaluated against Crematogaster scutellaris ants and Kalotermes flavicollis termites.
METHODS AND RESULTS:
Iridoid glucosides 1-7 were isolated for the first time as metabolites of the investigated plant, along with the coumarin scopolin. The main components of the extract were found to be the non-acetylated iridoids: geniposidic acid (1), 10-hydroxyloganin (2), deacetyldaphylloside (3), monotropein (4), deacetylasperulosidic acid (5) and Scandoside (6), while asperulosidic acid (7) was present only in minute quantities. All isolated metabolites were identified on the basis of their spectral data.
CONCLUSIONS:
Laboratory bioassays revealed significant levels of toxicity for 1-4 against Kalotermes flavicollis termites and Crematogaster scutellaris ants.

Protocol of Scandoside

Kinase Assay

Scandoside Exerts Anti-Inflammatory Effect Via Suppressing NF-κB and MAPK Signaling Pathways in LPS-Induced RAW 264.7 Macrophages.[Reference: WebLink]

International Journal of Molecular Sciences, 2018, 19(2):457.

The iridoids of Hedyotis diffusa Willd play an important role in the anti-inflammatory process, but the specific iridoid with anti-inflammatory effect and its mechanism has not be thoroughly studied.
METHODS AND RESULTS:
An iridoid compound named Scandoside (SCA) was isolated from H. diffusa and its anti-inflammatory effect was investigated in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages. Its anti-inflammatory mechanism was confirmed by in intro experiments and molecular docking analyses. As results, SCA significantly decreased the productions of nitric oxide (NO), prostaglandin E₂ (PGE₂), tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) and inhibited the levels of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), TNF-α and IL-6 messenger RNA (mRNA) expression in LPS-induced RAW 264.7 macrophages. SCA treatment suppressed the phosphorylation of inhibitor of nuclear transcription factor kappa-B alpaha (IκB-α), p38, extracellular signal-regulated kinase (ERK) and c-Jun N-terminal kinase (JNK). The docking data suggested that SCA had great binding abilities to COX-2, iNOS and IκB.
CONCLUSIONS:
Taken together, the results indicated that the anti-inflammatory effect of SCA is due to inhibition of pro-inflammatory cytokines and mediators via suppressing the nuclear transcription factor kappa-B (NF-κB) and mitogen-activated protein kinase (MAPK) signaling pathways, which provided useful information for its application and development.

Scandoside Dilution Calculator

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Preparing Stock Solutions of Scandoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.5621 mL 12.8107 mL 25.6213 mL 51.2426 mL 64.0533 mL
5 mM 0.5124 mL 2.5621 mL 5.1243 mL 10.2485 mL 12.8107 mL
10 mM 0.2562 mL 1.2811 mL 2.5621 mL 5.1243 mL 6.4053 mL
50 mM 0.0512 mL 0.2562 mL 0.5124 mL 1.0249 mL 1.2811 mL
100 mM 0.0256 mL 0.1281 mL 0.2562 mL 0.5124 mL 0.6405 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 Scandoside

Estimation of p-coumaric acid as metabolite of E-6-O-p-coumaroyl scandoside methyl ester in rat plasma by HPLC and its application to a pharmacokinetic study.[Pubmed:16388996]

J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Feb 2;831(1-2):303-6.

A rapid and simple high-performance liquid chromatographic (HPLC) method has been developed for the determination of p-coumaric acid in rat plasma and applied to a pharmacokinetic study in rats after administration of a prodrug, E-6-O-p-coumaroyl Scandoside methyl ester, isolated from Hedyotis diffusa (Willd.). Sample preparation involved protein precipitation with acetonitrile. The supernatant was then injected onto a Diamonsil C(18) column (250 mm x 4.6mm i.d., 5 microm). The mobile phase consisted of acetonitrile-water (21:79, v/v) with 1% glacial acetic acid. The UV detector was set at 310 nm. The lower limit of quantification of p-coumaric acid in rat plasma was 0.02 microg/mL. The calibration curves were linear over the concentration range 0.02-5 microg/mL with correlations greater than 0.999. The assay procedure was applied to the study of the metabolite pharmacokinetics of E-6-O-p-coumaroyl Scandoside methyl ester in rat.

[Determination of scandoside methyl ester in Hedyotis chrysotricha by HPLC].[Pubmed:20069906]

Zhongguo Zhong Yao Za Zhi. 2009 Oct;34(20):2619-21.

OBJECTIVE: To develop an HPLC method for determination of Scandoside methyl ester in Hedyotis chrysotricha. METHOD: The determination was carried out on an HC-C18 column elnted with acetonitrile-water (7:93) as mobile phase, and the detection wavelength was set at 238 nm. RESULT: There is a good linearity in the range 22.08-552 mg L(-1) of Scandoside methyl ester and the average recovery is 97.7% (n = 6), RSD 0.72%. CONCLUSION: This method is convenient, quick, and is applicable to the quality control of H. chrysotricha.

[In vivo comparison analysis of scandoside methyl ester metabolites in four kinds of liver microsomes using ultra-performance liquid chromatography combined with electrospray ionization tandem orbitrap mass spectrometry].[Pubmed:25518332]

Yao Xue Xue Bao. 2014 Sep;49(9):1315-9.

In order to clarify the metabolism pathways of Scandoside methyl ester, the analysis of metabolites profiling in four kinds of liver microsomes was performed by using an ultra-performance liquid chromatography/ electrospray-tandem mass spectrometry (UPLC-ESI-MS). The data obtained from the 0 h-incubation and the 2 h-incubation were compared and analyzed. After incubation, 5 metabolites of Scandoside methyl ester were found in rat, Beagles, rhesus monkey and human liver microsome. The results showed that Scandoside methyl ester's major metabolic pathway in the liver microsomes is hydrolysis, oxidation and reduction reactions, and there are certain kinds differences between species. The study provides a research base for further research about iridoid compounds in vivo metabolic pathways.

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