Astragalin

Names

[ CAS No. ]:
480-10-4

[ Name ]:
Astragalin

[Synonym ]:
5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl b-D-glucopyranoside
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl β-D-glucopyranoside
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl-β-D-glucopyranoside
Kaempferol-3-O-D-glucopyranoside
4H-1-Benzopyran-4-one, 3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-
Kaempferol-3-β-glucopyranoside
5,7-Dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-4H-chromen-4-one
Kaempferol-3-O-glucoside
Kaempferol 3-O-β-D-glucoside
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
kaempferol 3-O-glucoside
Astragaloside
MFCD00075932
Kaempferol-3-O-β-D-glucopyranoside
Kaempferol-3-β-monoglucoside
Kaempferol-3-D-glucoside
Kaempferol 3-O-β-D-glucopyranoside
3-Glucosylkaempferol
Astragalin
5,7-Dihydroxy-2-(4-hydroxyphényl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]oxy}-4H-chromén-4-one
Kaempferol-3-glucoside
5,7-Dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-4H-chromen-4-on
Kaempferol 3-glucoside

Biological Activity

[Description]:

Astragalin (kaempferol-3-O-glucoside) is a flavonoid with anti-inflammatory activity and newly found in persimmon leaves and green tea seeds.IC50 value:Target: in vitro: Astragalin nontoxic at ≤ 20 μM suppressed cellular induction of Toll-like receptor 4 (TLR4) and ROS production enhanced by LPS. Both LPS and H2O2 induced epithelial eotaxin-1 expression, which was blocked by astragalin. LPS activated and induced PLCγ1, PKCβ2, and NADPH oxidase subunits of p22phox and p47phox in epithelial cells and such activation and induction were demoted by astragalin or TLR4 inhibition antagonizing eotaxin-1 induction. H2O2-upregulated phosphorylation of JNK and p38 MAPK was dampened by adding astragalin to epithelial cells, while this compound enhanced epithelial activation of Akt and ERK. H2O2 and LPS promoted epithelial apoptosis concomitant with nuclear condensation or caspase-3 activation, which was blunted by astragalin [1]. astragalin suppressed the expression of tumor necrosis factor α, interleukin 6, and nitric oxide in a dose-dependent manner in mMECs [2]. astragalin attenuated the infiltration of inflammatory cells, the activity of myeloperoxidase (MPO) and the expression of tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6) and interleukin-1β (IL-1β) in a dose-dependent manner. Additionally, Western blotting results showed that astragalin efficiently blunt decreased nuclear factor-kappaB (NF-κB) activation by inhibiting the degradation and phosphorylation of IκBα and the nuclear translocation of p65 [3]. Astragalin significantly reduced LPS-induced expression of iNOS, COX-2 and cytokines/chemokines, and production of NO in J774A.1 mouse macrophages. Astragalin inhibited LPSinduced activation of NF-κB as indicated by inhibition of degradation of IκBα, nuclear translocation of NF-κB, and NF-κB dependent gene reporter assay [4].in vivo: Mice were injected intraperitoneally (i.p.) with lipopolysaccharide (LPS) (dose range: 5-40 mg/kg). pretreatment with astragalin can improve survival during lethal endotoxemia and attenuate inflammatory responses in a murine model of lipopolysaccharide-induced acute lung injury [4].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Flavonoids

Research Areas >> Inflammation/Immunology

[References]

[1]. Cho IH, et al. Astragalin inhibits airway eotaxin-1 induction and epithelial apoptosis through modulating oxidative stress-responsive MAPK signaling. BMC Pulm Med. 2014 Jul 29;14:122.

[2]. Li F, et al. Inhibitory effects of astragalin on lipopolysaccharide-induced inflammatory response in mouse mammary epithelial cells. J Surg Res. 2014 Dec;192(2):573-81.

[3]. Li F, et al. Astragalin suppresses inflammatory responses via down-regulation of NF-κB signaling pathway in lipopolysaccharide-induced mastitis in a murine model. Int Immunopharmacol. 2013 Oct;17(2):478-82.

[4]. Kim MS, et al. Inhibitory effect of astragalin on expression of lipopolysaccharide-induced inflammatory mediators through NF-κB in macrophages. Arch Pharm Res. 2011 Dec;34(12):2101-7.

[5]. Soromou LW, et al. Astragalin attenuates lipopolysaccharide-induced inflammatory responses by down-regulating NF-κB signaling pathway. Biochem Biophys Res Commun. 2012 Mar 9;419(2):256-61.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
823.2±65.0 °C at 760 mmHg

[ Melting Point ]:
223-229ºC

[ Molecular Formula ]:
C₂₁H₂₀O₁₁

[ Molecular Weight ]:
448.377

[ Flash Point ]:
291.6±27.8 °C

[ Exact Mass ]:
448.100555

[ PSA ]:
190.28000

[ LogP ]:
1.95

[ Vapour Pressure ]:
0.0±3.1 mmHg at 25°C

[ Index of Refraction ]:
1.774

[ Storage condition ]:
?20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ3080000

CHEMICAL NAME :: 4H-1-Benzopyran-4-one, 3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydro xyphenyl)-

CAS REGISTRY NUMBER :: 480-10-4

LAST UPDATED :: 199410

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C21-H20-O11

MOLECULAR WEIGHT :: 448.41

WISWESSER LINE NOTATION :: T66 BO EVJ CR DQ& GQ IQ DO- BT6OTJ CQ DQ EQ F1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 10 ug/plate

REFERENCE :: ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 3,401,1981

Safety Information

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
22

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
DJ3080000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Separation of patuletin-3-O-glucoside, astragalin, quercetin, kaempferol and isorhamnetin from Flaveria bidentis (L.) Kuntze by elution-pump-out high-performance counter-current chromatography.

J. Chromatogr. A. 1218(36) , 6206-11, (2011)

Flaveria bidentis (L.) Kuntze is an annual alien weed of Flaveria Juss. (Asteraceae) in China. Bioactive compounds, mainly flavonol glycosides and flavones from F. bidentis (L.) Kuntze, have been stud...

A sensitive LC-MS/MS method for simultaneous determination of six flavonoids in rat plasma: application to a pharmacokinetic study of total flavonoids from mulberry leaves.

J. Pharm. Biomed. Anal. 84 , 189-95, (2013)

A simple and sensitive LC-MS/MS method has been developed and validated for the determination of rutin, isoquercitrin, astragalin, quercetin, kaempferol and isorhamnetin in rat plasma using naringin a...

[Study on the chemical constituets in ethyl acetante extraction from semen litchi].

Zhong Yao Cai 35(1) , 64-6, (2012)

To study the chemical constituents in ethyl acetate extraction of Semen Litchi.The compounds were isolated and purified by column chromatography on silica gel and Sephadex LH-20 coupled with preparati...