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Astilbin

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-A3020

  • Specification : 98%

  • CAS number : 29838-67-3

  • Formula : C21H22O11

  • Molecular Weight : 450.4

  • PUBCHEM ID : 119258

  • Volume : 25mg

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Catalogue Number

BF-A3020

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

450.4

Appearance

White crystalline powder

Botanical Source

Smilax glabra

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1C(C(C(C(O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O

Synonyms

4H-1-Benzopyran-4-one, 3-[(6-deoxy-α-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-, (2R,3R)-/Astilbin Dihydroquercetin 3-rhamnoside Taxifolin 3-rhamnoside/4H-1-Benzopyran-4-one, 3-((6-deoxy-α-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-, (2R,3R)-/Taxifolin 3-rhamnoside/Neoisoastilbin/Astilbin/(2R-trans)-3-((6-Deoxy-α-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one/4H-1-Benzopyran-4-one, 3-((6-deoxy-α-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-, (2R-trans)-/Taxifolin 3-O-rhamnoside/Astilbin from Engelhardtia roxburghiana/(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one/(2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chromen-3-yl 6-deoxy-α-L-mannopyranoside

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one

Density

1.7±0.1 g/cm3

Solubility

Methanol; Acetontrile; DMSO

Flash Point

282.9±27.8 °C

Boiling Point

801.1±65.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:29838-67-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

28700975

Abstract

Psoriasis is a common chronic dermatosis characterized by keratinocyte hyperproliferation accompanied by inflammatory reactions. Pathological changes upset the balance between keratinocyte proliferation, differentiation, and death in psoriatic lesions, suggesting that molecules with topical anti-inflammatory, anti-proliferation and anti-angiogenesis abilities may be useful for its treatment. The flavonoid astilbin is the major active component extracted from the rhizome of Smilax glabra, which has been widely used in China to treat inflammatory and autoimmune diseases. Here, we investigate the potential of astilbin as a treatment for psoriasis. We reveal that astilbin inhibits the growth of HaCaT keratinocytes. Detailed study shows that astilbin leads to S phase arrest of the cell cycle by induction of p53 and p21 and activated-AMPK. Additionally, astilbin induced keratinocyte differentiation correlated with suppression of keratin 5 (KRT5) and KRT14 proteins (the markers of epidermal basal layer) and induction KRT1 and KRT10 proteins (occurring in the upper layers). Moreover, astilbin regulates the expression of VEGF in human HaCaT keratinocytes. These results suggest that astilbin may be a promising agent for psoriasis treatment.

KEYWORDS

Astilbin; HaCaT; Keratinocyte differentiation; Psoriasis; VEGF.

Title

Astilbin Decreases Proliferation and Improves Differentiation in HaCaT Keratinocytes

Author

Chunhong Zhang 1 , Qingqing Xu 1 , Xi Tan 1 , Liya Meng 1 , Guo Wei 1 , Ying Liu 1 , Chunmin Zhang 2

Publish date

2017 Sep

PMID

29653345

Abstract

Astilbin is the most predominant flavonoid in Rhizoma Smilacis Glabrae (RSG) with many bioactivities. The interconversion of the astilbin and its three stereoisomers was found with incubation of RSG extract at different temperatures, and the equilibrium ratios were calculated. Under certain conditions, neoastilbin would replace astilbin and become the predominant flavonoid in RSG extract. The effects of ascorbic acid, sucrose, sodium benzoate, β-cyclodextrin (β-CD) and common metal ions on the isomerization and decomposition of astilbin were studied. Ascorbic acid showed the best protective effect on the decomposition of astilbin and its isomers, which may be attributed to its reducing and radical scavenging ability. Besides, ascorbic acid also accelerated the isomerization of astilbin. β-CD suppressed both isomerization and decomposition of astilbin through complexation between them. Most metal ions had inhibition effects on the isomerization of astilbin. Al3+ could almost completely inhibit the isomerization. The presence of Fe3+ caused the rapid decomposition of astilbin, and Cu2+ also showed weak effects. Based on the isomerization study, a novel and simple method for preparative separation of astilbin and neoastilbin from RSG sample was developed. Astilbin and neoastilbin with purity of 93% and yield of 0.86% and 0.48% were obtained, respectively, which represent 46.8% of total flavonoids in RSG sample. By controlling the isomerization conditions, astilbin and neoastilbin could be used as the initial reactants to produce neoisoastilbin and isoastilbin, respectively.

KEYWORDS

Astilbin; HaCaT; Keratinocyte differentiation; Psoriasis; VEGF.

Title

Isomerization of Astilbin and Its Application for Preparation of the Four Stereoisomers From Rhizoma Smilacis Glabrae

Author

Dan Zheng 1 , Li Zhang 1 , Qing-Feng Zhang 2

Publish date

2018 Jun 5

PMID

29621624

Abstract

Background and objective: The nature of pulmonary fibrosis involves inadequate repair of the epithelial cell barrier accompanied by impaired regulation of the fibroblast. Moreover, pulmonary fibrosis currently lacks an effective therapeutic drug. This study targets the protection of the epithelial cell and fibroblast to identify a novel, potentially therapeutic drug (i.e., astilbin).
Methods: In this study, the cytotoxicity of astilbin was firstly detected using CCK-8. A real-time proliferation/migration analysis system was used to test the inhibitory proliferation and migration of astilbin in vitro. The expression of mesenchymal markers and the loss of epithelial cell markers were analyzed to evaluate the antifibrotic activity of astilbin on TGF-β1-treated AEC-II and L929 cells and bleomycin-treated mice. Then, in fibrosis-associated signaling pathways, the regulation of astilbin was tested using RNA sequencing and Cignal Finder 45-Pathway system. Rescue and other experiments were used to confirm this pathway regulation further.
Results: The data showed that astilbin inhibited proliferation and migration of cell samples. Its treatment resulted in the reduction of pathological score and collagen deposition, with a decrease in α-SMA and Snail and an increase in E-cadherin and SP-C in vivo and in vitro. The fibrosis-associated aberrant genes are some of the most notable components of the Hedgehog signaling pathway.
Conclusions: Astilbin ameliorates pulmonary fibrosis via blockade of Hedgehog signaling pathway and has potential therapeutic value for lung fibrosis treatment.

KEYWORDS

Anti-pulmonary fibrosis; Astilbin; Hedgehog pathway.

Title

Astilbin Ameliorates Pulmonary Fibrosis via Blockade of Hedgehog Signaling Pathway

Author

Jie Zhang 1 , Hanchen Liu 2 , Chenguang Song 3 , Jinjin Zhang 1 , Youlei Wang 4 , Changjun Lv 5 , Xiaodong Song 6

Publish date

2018 Jun


Description :

Astilbin, a flavonoid compound, is isolated from the rhizome of Smilax glabra. Astilbin enhances NRF2 activation. Astilbin also suppresses TNF-α expression and NF-κB activation.