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Schaftoside

$198

  • Brand : BIOFRON

  • Catalogue Number : BF-S1007

  • Specification : 98%

  • CAS number : 51938-32-0

  • Formula : C26H28O14

  • Molecular Weight : 564.49

  • PUBCHEM ID : 442658

  • Volume : 20mg

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Catalogue Number

BF-S1007

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

564.49

Appearance

White crystalline powder

Botanical Source

Pinellia ternata,Ilex cornuta,Arisaema heterophyllum,Mallotus apelta,Desmodium styracifolium

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

C1C(C(C(C(O1)C2=C3C(=C(C(=C2O)C4C(C(C(C(O4)CO)O)O)O)O)C(=O)C=C(O3)C5=CC=C(C=C5)O)O)O)O

Synonyms

4H-1-Benzopyran-4-one, 8-(D-arabinopyranosyloxy)-6-(D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-/Shaftoside/Apigenin 8-C-|A-L-arabinoside 6-C-|A-D-glucoside/Schaftoside/5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one/8-(D-Arabinopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl D-glucopyranoside/schaftozide

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one

Density

1.8±0.1 g/cm3

Solubility

Methanol; DMF; DMSO

Flash Point

342.7±27.8 °C

Boiling Point

1028.2±65.0 °C at 760 mmHg

Melting Point

228ºC

InChl

InChI=1S/C26H28O14/c27-6-13-18(32)21(35)23(37)26(40-13)15-19(33)14-10(29)5-12(8-1-3-9(28)4-2-8)39-24(14)16(20(15)34)25-22(36)17(31)11(30)7-38-25/h1-5,11,13,17-18,21-23,25-28,30-37H,6-7H2/t11-,13+,17-,18+,21-,22+,23+,25-,26-/m0/s1

InChl Key

MMDUKUSNQNWVET-VYUBKLCTSA-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#:51938-32-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29890139

Abstract

Skin pigmentation involves multiple processes, including melanin synthesis, transport, and melanosome release. Melanin content determines skin color and protects against UV radiation-induced damage. Autophagy is a cooperative process between autophagosomes and lysosomes that degrades cellular components and organelles. In the present study, B16F1 cells were treated with Rhizoma Arisaematis extract (RA) and assessed for pigmentation and autophagy regulation. RA treatment suppressed the α-MSH-stimulated increase of melanogenesis and down-regulated the expression of tyrosinase and TRP1 proteins in B16F1 cells. In addition, autophagy was activated in RA-treated cells. Inhibition of autophagy reduced the anti-melanogenic activity of RA in α-MSH-treated B16F1 cells. We identified schaftoside as an effector molecule by LC-MS analysis of RA. Consistently, treatment of schaftoside showed anti-melanogenic effect and induced autophagy activation in B16F1 cells. Inhibition of autophagy by 3 MA treatment reduced the anti-melanogenic effect of the schaftoside and recovered expression level of melanogenesis regulators in α-MSH-treated B16F1 cells. Taken together, our results suggest that schaftoside from RA inhibits skin pigmentation through modulation of autophagy.

Copyright © 2018 Elsevier Inc. All rights reserved.

Title

Anti-melanogenic activity of schaftoside in Rhizoma Arisaematis by increasing autophagy in B16F1 cells.

Author

Kim PS1, Shin JH2, Jo DS2, Shin DW2, Choi DH3, Kim WJ4, Park K4, Kim JK4, Joo CG5, Lee JS4, Choi Y4, Shin YW2, Shin JJ5, Jeon HB6, Seo JH7, Cho DH8.

Publish date

2018 Sep 3

PMID

29896209

Abstract

Brown planthopper (BPH) Nilaparvata lugens Stal is a serious insect pest of rice in Asian countries. Active compounds have close relationship with rice resistance against BPH. In this study, HPLC, MS/MS, and NMR techniques were used to identify active compounds in total flavonoids of rice. As a result, a BPH resistance-associated compound, Peak 1 in HPLC chromatogram of rice flavonoids, was isolated and identified as schaftoside. Feeding experiment with artificial diet indicated that schaftoside played its role in a dose dependent manner, under the concentration of 0.10 and 0.15 mg mL-1, schaftoside showed a significant inhibitory effect on BPH survival (p < 0.05), in comparison with the control. The fluorescent spectra showed that schaftoside has a strong ability to bind with NlCDK1, a CDK1 kinase of BPH. The apparent association constant KA for NlCDK1 binding with schaftoside is 6.436 × 103 L/mol. Docking model suggested that binding of schaftoside might affect the activation of NlCDK1 as a protein kinase, mainly through interacting with amino acid residues Glu12, Thr14 and Val17 in the ATP binding element GXGXXGXV (Gly11 to Val18). Western blot using anti-phospho-CDK1 (pThr14) antibody confirmed that schaftoside treatment suppressed the phosphorylation on Thr-14 site of NlCDK1, thus inhibited its activation as a kinase. Therefore, this study revealed the schaftoside-NlCDK1 interaction mode, and unraveled a novel mechanism of rice resistance against BPH.

KEYWORDS

CDK1 protein; brown planthopper; flavonoids; interaction mechanism; rice; schaftoside; varietal resistance

Title

Schaftoside Interacts With NlCDK1 Protein: A Mechanism of Rice Resistance to Brown Planthopper, Nilaparvata lugens.

Author

Hao PY1, Feng YL1, Zhou YS1, Song XM1, Li HL1, Ma Y1, Ye CL1, Yu XP1.

Publish date

2018 May 29

PMID

30528467

Abstract

BACKGROUND:
Neuroinflammation plays a major role in the development of ischemic stroke, and regulation of the proinflammatory TLR4 signaling pathway in microglia stands to be a promising therapeutic strategy for stroke intervention. Recently, the homeostasis of mitochondrial dynamics has also been raised as a vital component in maintaining neuronal health, but its relevance in microglia hasn’t been investigated. Schaftoside, a natural flavonoid compound and a promising treatment for inflammation, has demonstrated potency against LPS-induced lung inflammation in mice; however, its action on TLR4-induced neuroinflammation and mitochondrial dynamics in microglia is still unknown.

METHODS:
The effects of schaftoside in regulating inflammation and mitochondrial dynamics were investigated in vitro in oxygen glucose deprivation (OGD)-stimulated BV2 microglia cells.

RESULTS:
Schaftoside inhibited mRNA and protein expressions of proinflammatory cytokines (IL-1β, TNF-α, and IL-6) after 4 h in OGD-stimulated BV2 microglia cells, similar to the effect of TAK242, an inhibitor of TLR4. TLR4/Myd88 signaling pathway was effectively suppressed by schaftoside. In addition, both schaftoside and TAK242 treatments significantly decreased Drp1 expression, phosphorylation, translocation and mitochondrial fission in OGD-stimulated BV2 cells.

CONCLUSIONS:
Our study suggested that schaftoside was able to reduce neuroinflammation, which is mediated in part by reducing TLR4/Myd88/Drp1-related mitochondrial fission in BV2 microglia cells.

Copyright © 2018 The Authors. Production and hosting by Elsevier B.V. All rights reserved.

KEYWORDS

Microglia; Mitochondrial fission; Schaftoside; Stroke; TLR4

Title

Schaftoside ameliorates oxygen glucose deprivation-induced inflammation associated with the TLR4/Myd88/Drp1-related mitochondrial fission in BV2 microglia cells.

Author

Zhou K1, Wu J1, Chen J1, Zhou Y1, Chen X1, Wu Q1, Xu Y2, Tu W1, Lou X3, Yang G3, Jiang S4.

Publish date

2019 Jan


Description :

Schaftoside is a flavonoid found in a variety of Chinese herbal medicines, such as Eleusine indica. Schaftoside inhibits the expression of TLR4 and Myd88. Schaftoside also decreases Drp1 expression and phosphorylation, and reduces mitochondrial fission[1].