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Darutoside

$896

  • Brand : BIOFRON

  • Catalogue Number : BD-P0779

  • Specification : 98.5%(HPLC&TLC)

  • CAS number : 59219-65-7

  • PUBCHEM ID : 44715524

  • Volume : 25mg

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Catalogue Number

BD-P0779

Analysis Method

HPLC,NMR,MS

Specification

98.5%(HPLC&TLC)

Storage

2-8°C

Molecular Weight

Appearance

Powder

Botanical Source

Palafoxia arida and Siegesbeckia orientalis

Structure Type

Diterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(C2CCC3=CC(CCC3C2(CCC1OC4C(C(C(C(O4)CO)O)O)O)C)(C)C(CO)O)C

Synonyms

(3α,5β,9β,10α,13α,15R)-15,16-Dihydroxypimar-8(14)-en-3-yl β-D-glucopyranoside/β-D-Glucopyranoside, (2R,4aS,4bR,7S,10aS)-7-[(1R)-1,2-dihydroxyethyl]-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,1,4a,7-tetramethyl-2-phenanthrenyl

IUPAC 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

Applications

Darutoside is a diterpenoid isolated from Siegesbeckia[1].

Density

1.3±0.1 g/cm3

Solubility

Methanol; DMSO

Flash Point

357.2±31.5 °C

Boiling Point

667.0±55.0 °C at 760 mmHg

Melting Point

InChl

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

InChl Key

QWWPCQGHWWNGET-LCVVDEIYSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:59219-65-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

28302401

Abstract

Five new diterpenoid glycosides, siegesides A-E (1-5), along with the known compound darutoside (6) were isolated and characterized from the ethanol extract of Siegesbeckia pubescens. The structural elucidation of the isolates was accomplished by extensive HRESIMS and NMR analysis. Compounds 1 and 2 are epimers of 6. All isolates were evaluated for their inhibition on the migration of MB-MDA-231 breast cancer cells induced by the chemokine epithelial growth factor, and compound 2 showed superior inhibitory activities in comparison with the positive control drug with IC50 value of 0.27μM.

Copyright © 2017 Elsevier Ltd. All rights reserved.

KEYWORDS

Chemokine epithelial growth factor; Diterpenoid glycosides; MB-MDA-231 breast cancer cells; Siegesbeckia pubescens

Title

Isolation and characterization of diterpene glycosides from Siegesbeckia pubescens.

Author

Wang J1, Xie K1, Duan H2, Wang Y1, Ma H3, Fu H4.

Publish date

2017 Apr 15

PMID

25278181

Abstract

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 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.

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.

Copyright © 2014 Elsevier Ireland Ltd. All rights reserved.

KEYWORDS

Anti-inflammatory effect; Cytotoxicity; Herba Siegesbeckiae; Processing with rice wine; UPLC/Q-TOF-MS

Title

Comparisons of the chemical profiles, cytotoxicities and anti-inflammatory effects of raw and rice wine-processed Herba Siegesbeckiae.

Author

Su T1, Yu H1, Kwan HY1, Ma XQ1, Cao HH1, Cheng CY1, Leung AK1, Chan CL1, Li WD1, Cao H2, Fong WF1, Yu ZL3.

Publish date

2014 Oct 28;

PMID

20687099

Abstract

A rapid and simple reverse-phase high-performance liquid chromatography (RP-HPLC) was developed and validated for the quantification of kirenol in rat plasma after oral administration. Kirenol and darutoside (internal standard, IS) were extracted from rat plasma using Cleanert™ C(18) solid-phase extraction (SPE) cartridge. Analysis of the extraction was performed on a Thermo ODS-2 Hypersil C(18) reversed-phase column with a gradient eluent composed of acetonitrile and 0.1% phosphoric acid. The flow rate was 1.0 mL/min and the detection wavelength was set at 215 nm. The calibration curve was linear over the range of 9.756-133.333 µg/mL (r(2) = 0.9991) in rat plasma. The lower limits of detection and quantification were 2.857 and 9.756 µg/mL, respectively. The intra- and inter-day precisions (relative standard deviation, RSD) were between 2.24 and 4.46%, with accuracies ranging from 91.80 to 102.74%. The extraction recovery ranged from 98.16 to 107.62% with RSD less than 4.81%. Stability studies showed that kirenol was stable in preparation and analytical process. The present method was successfully applied to the pharmacokinetic study of kirenol in male Sprague-Dawley rats after oral administration at a dose of 50 mg/kg.

Copyright © 2010 John Wiley & Sons, Ltd.

Title

A rapid and simple RP-HPLC method for quantification of kirenol in rat plasma after oral administration and its application to pharmacokinetic study.

Author

Song XL1, Zhang QY, Wang ZM, Fu HZ, Qian RQ.

Publish date

2011 May;