Darutoside

CAS# 59219-65-7

Darutoside

Catalog No. BCN4094----Order now to get a substantial discount!

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Quality Control of Darutoside

Number of papers citing our products

Chemical structure

Darutoside

3D structure

Chemical Properties of Darutoside

Cas No. 59219-65-7 SDF Download SDF
PubChem ID 44715524 Appearance White powder
Formula C26H44O8 M.Wt 484.6
Type of Compound Diterpenoids Storage Desiccate at -20°C
Synonyms Darutigenol 3-glucoside
Solubility Soluble in methanol and DMSO
Chemical Name (2R,3R,4S,5S,6R)-2-[[(2R,4aS,4bR,7S,10aS)-7-[(1R)-1,2-dihydroxyethyl]-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthren-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES CC1(C2CCC3=CC(CCC3C2(CCC1OC4C(C(C(C(O4)CO)O)O)O)C)(C)C(CO)O)C
Standard InChIKey QWWPCQGHWWNGET-LCVVDEIYSA-N
Standard InChI InChI=1S/C26H44O8/c1-24(2)17-6-5-14-11-25(3,18(29)13-28)9-7-15(14)26(17,4)10-8-19(24)34-23-22(32)21(31)20(30)16(12-27)33-23/h11,15-23,27-32H,5-10,12-13H2,1-4H3/t15-,16-,17-,18+,19-,20-,21+,22-,23+,25+,26+/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 Darutoside

The herb of Siegesbeckia orientalis.

Biological Activity of Darutoside

DescriptionDarutoside can improve skin elasticity, surface appearance and stretch mark removal, through soothing the skin, decreasing inflammation, restoring collagen and promoting collagen production; it could as an appropriate treatment for wounds.
TargetsImmunology & Inflammation related
In vitro

Comparisons of the chemical profiles, cytotoxicities and anti-inflammatory effects of raw and rice wine-processed Herba Siegesbeckiae.[Pubmed: 25278181]

J Ethnopharmacol. 2014 Oct 28;156:365-9.

Although slightly toxic, the Chinese medicinal herb Herba Siegesbeckiae (HS) has long been used as a remedy for traditional Chinese medicine symptoms that resemble inflammatory joint disorders, because it can eliminate the wind-dampness and soothe painful joints. Proper processing can reduce the toxicity and/or enhance the efficacy of raw herbs. In this study, we aim to examine if processing with rice wine reduces the cytotoxicities and/or enhances the anti-inflammatory effects of HS, and to explore the chemical basis behind the potential changes of medicinal properties caused by the processing.
METHODS AND RESULTS:
We used cell models to examine the cytotoxicities and anti-inflammatory effects of HS and rice wine-processed HS (WHS). The chemical profiles of HS and WHS were compared using the ultra-performance liquid chromatography/quadrupole-time-of-flight mass spectrometry (UPLC/Q-TOF-MS) analysis. We found that WHS was less toxic than HS in cultured cells as shown in the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Both HS and WHS had anti-inflammatory effects as demonstrated by their abilities to reduce nitric oxide (NO) production as well as protein and mRNA expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Interestingly, the anti-inflammatory effects of WHS were more potent than that of HS at the concentration of 100 μg/mL. By comparing the chemical profiles, we found that 19 peaks were lower, while 2 other peaks were higher in WHS than in HS. Four compounds including neo-Darutoside, Darutoside, stigmasterol and 16-O-acetylDarutoside corresponding to 4 individual changed peaks were tentatively identified by matching with empirical molecular formulae and mass fragments.
CONCLUSIONS:
Our study showed that processing with rice wine significantly reduced the cytotoxicities and enhanced the anti-inflammatory effects of HS as demonstrated in cell models. We also developed a UPLC/Q-TOF-MS method to clearly differentiate HS from WHS by their different chemical profiles. Further study is warranted to establish the relationship between the alteration of chemical profiles and the changes of medicinal properties caused by processing with rice wine.

Protocol of Darutoside

Structure Identification
Zhongguo Zhong Yao Za Zhi. 2014 Aug;39(15):2907-11.

Study on index components and fingerprints of crude and processed Siegesbeckia Herbs.[Pubmed: 25507552]

The change of kirenol, darutigenol and Darutoside in Siegesbeckia and its first to ninth processed products were studied, and the ten fingerprints were compared, which provided the experimental basis for the study of Siegesbeckia processing tech- nology.
METHODS AND RESULTS:
The samples were analysed by HPLC on a SunFire-C18 column (4.6 mm x 150 mm, 5 μm) with gradient elution of acetonitrile (0.1% formic acid)-water (0.1% formic acid) at a flow rate of 1.0 mL x min(-1). Column temperaturewas 30 °C and the detected wavelength was 215, 320 nm. The calibration curves of kirenol, darutigenol and Darutoside were linear in the range of 2.180-26.16, 2.900-34.80, and 1.012-6.072 mg x L(-1), respectively, and the average recoveries were 96.4%, 97.2% and 96.3% wit RSD 2.2%, 1.7% and 2.4%.
CONCLUSIONS:
This method was simple, the result was stable and had good repeatability, recovery and precision. The result was the basis of the chemical contents variation in the processing of Siegesbeckia Herbs and further clarifying the effect of the changing.

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Preparing Stock Solutions of Darutoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0636 mL 10.3178 mL 20.6356 mL 41.2712 mL 51.5889 mL
5 mM 0.4127 mL 2.0636 mL 4.1271 mL 8.2542 mL 10.3178 mL
10 mM 0.2064 mL 1.0318 mL 2.0636 mL 4.1271 mL 5.1589 mL
50 mM 0.0413 mL 0.2064 mL 0.4127 mL 0.8254 mL 1.0318 mL
100 mM 0.0206 mL 0.1032 mL 0.2064 mL 0.4127 mL 0.5159 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 Darutoside

Comparisons of the chemical profiles, cytotoxicities and anti-inflammatory effects of raw and rice wine-processed Herba Siegesbeckiae.[Pubmed:25278181]

J Ethnopharmacol. 2014 Oct 28;156:365-9.

ETHNOPHARMACOLOGICAL RELEVANCE: Although slightly toxic, the Chinese medicinal herb Herba Siegesbeckiae (HS) has long been used as a remedy for traditional Chinese medicine symptoms that resemble inflammatory joint disorders, because it can eliminate the wind-dampness and soothe painful joints. Proper processing can reduce the toxicity and/or enhance the efficacy of raw herbs. In this study, we aim to examine if processing with rice wine reduces the cytotoxicities and/or enhances the anti-inflammatory effects of HS, and to explore the chemical basis behind the potential changes of medicinal properties caused by the processing. MATERIALS AND METHODS: We used cell models to examine the cytotoxicities and anti-inflammatory effects of HS and rice wine-processed HS (WHS). The chemical profiles of HS and WHS were compared using the ultra-performance liquid chromatography/quadrupole-time-of-flight mass spectrometry (UPLC/Q-TOF-MS) analysis. RESULTS: We found that WHS was less toxic than HS in cultured cells as shown in the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Both HS and WHS had anti-inflammatory effects as demonstrated by their abilities to reduce nitric oxide (NO) production as well as protein and mRNA expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Interestingly, the anti-inflammatory effects of WHS were more potent than that of HS at the concentration of 100 mug/mL. By comparing the chemical profiles, we found that 19 peaks were lower, while 2 other peaks were higher in WHS than in HS. Four compounds including neo-Darutoside, Darutoside, stigmasterol and 16-O-acetylDarutoside corresponding to 4 individual changed peaks were tentatively identified by matching with empirical molecular formulae and mass fragments. CONCLUSION: Our study showed that processing with rice wine significantly reduced the cytotoxicities and enhanced the anti-inflammatory effects of HS as demonstrated in cell models. We also developed a UPLC/Q-TOF-MS method to clearly differentiate HS from WHS by their different chemical profiles. Further study is warranted to establish the relationship between the alteration of chemical profiles and the changes of medicinal properties caused by processing with rice wine.

Description

Darutoside is a diterpenoid isolated from Siegesbeckia.

Keywords:

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