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Key Documents

A2862

Sigma-Aldrich

Astilbin from Engelhardtia roxburghiana

≥98%

Synonym(s):

Astilbin, Dihydroquercetin 3-rhamnoside, Taxifolin 3-rhamnoside

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About This Item

Empirical Formula (Hill Notation):
C21H22O11
CAS Number:
Molecular Weight:
450.39
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.25

Quality Level

Assay

≥98%

form

powder

solubility

H2O: 1 mg/mL, clear, colorless

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

O=C1C2=C(O)C=C(O)C=C2O[C@H](C3=CC(O)=C(O)C=C3)[C@H]1O[C@@]4([H])[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O4

InChI

1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19-,20+,21-/m0/s1

InChI key

ZROGCCBNZBKLEL-MFSALPCASA-N

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General description

Astilbin belongs to the class of dihydroflavanol compounds and is the chief biologically active component of Rhizoma Smilacis Glabrae (RSG) extract. RSG is obtained from the dried rhizome of Smilax Glabra Roxb.

Application

Astilbin from Engelhardtia roxburghiana, a flavonoid phytochemical with antibacterial activity, may be used to study its pharmacology and the effects of its antiproliferative activities versus a variety of cell types.

Biochem/physiol Actions

Astilbin exerts various biological activities such as anti-oxidative, anti-bacterial, and inhibition of contact hypersensitivity. Also, it shows insecticidal, anti-oedematogenic, antinociceptive and antidepressant properties. It has an inhibitory effect on the aldose reductase enzyme, the accumulation of sorbitol, and a protective effect on the liver. Astilbin is helpful against autoimmune diseases such as rheumatoid arthritis due to its ability to reduce matrix metalloproteinase (MMP) activity and Nitric oxide production in T lymphocytes.
Flavonoid phytochemical found in St. John′s wort and Traditional Chinese Medicine herbal preparations. Immunosuppresive. Antiproliferative.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nicolas Landrault et al.
Journal of agricultural and food chemistry, 50(7), 2046-2052 (2002-03-21)
Phenolics from grapes and wines can play a role against oxidation and development of atherosclerosis. Stilbenes have been shown to have cancer chemopreventive activity and to protect lipoproteins from oxidative damage. A method for the direct determination of stilbene oligomers
S Zou et al.
Transplantation proceedings, 42(9), 3798-3802 (2010-11-26)
The effect of astilbin on acute graft rejection was investigated in C57BL/6 mice carrying BALB/c hearts heterotopically transplanted into the neck vessels. Daily treatment with astilbin (50, 125, or 250 mg/kg intraperitoneally) significantly prolonged the survival of grafts in a
H Haraguchi et al.
Bioscience, biotechnology, and biochemistry, 61(4), 651-654 (1997-04-01)
Dihydroflavonol taxifolin and its glycoside, astilbin, from Engelhardtia chrysolepis inhibited rat lens and recombinant human aldose reductase. Taxifolin also inhibited sorbitol accumulation in human red blood cells. Furthermore, this dihydroflavonol aglycone maintained the clarity of rat lens incubated with a
Luciane G Batista Pereira et al.
Pest management science, 58(5), 503-507 (2002-05-10)
Astilbin was isolated in high yield from Dimorphandra mollis, and its insecticidal and growth inhibiting activity by stomach ingestion were evaluated against Anticarsia gemmatalis and Spodoptera frugiperda. The insecticidal activity of astilbin, the weight reduction of the larval phase and
Xiao-Ya Shang et al.
Journal of Asian natural products research, 14(10), 966-972 (2012-10-11)
A new dihydroflavonol glycoside dimer 6,6-bisastilbin (1) and a new nitrile-containing metabolite (Z)-5α,6β-dihydroxy-4β-methoxy-2-cyclohexene-Δ(1,α)-acetonitrile (2), together with three known analogs, bauhinin, bauhinilide, and dehydrodicatechin A, have been isolated from an ethanol extract of Bauhinia aurea. Their structures were determined by spectroscopic

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