spiraeoside

Names

[ CAS No. ]:
20229-56-5

[ Name ]:
spiraeoside

[Synonym ]:
Spiraeosid
Quercetin 4'-b-D-glucopyranoside
Quercetin 4'-O-glucoside
Quercetin-4'-glucoside
EINECS 243-614-6
Spiraein
3,5,7-trihydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
quercetin 4'-O-beta-D-glucopyranoside
Spiraeoside

Biological Activity

[Description]:

Spiraeoside, an orally active natural compound, exerts antioxidant activity, inhibits reactive oxygen species (ROS) and malondialdehyde production. Spiraeoside possesses antiallergic, anti-inflammatory and antitumor activities[1].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

[In Vitro]

Spiraeoside elevates HG stimulation-caused the decrease in the expression levels of p-Akt, nuclear Nrf2, and HO-1 in AC16 cells (the effects of Spiraeoside are reversedby LY294002)[1]. Spiraeoside protects AC16 cells against HG-induced oxidative stress, cell injury, and apoptosis[1]. Spiraeoside activates the PI3K/Akt/Nrf2 pathway in AC16 cells on exposure to HG[1]. Spiraeoside protects AC16 cells against HG-induced apoptosis through the PI3K/Akt/Nrf2 pathway[1]. Cell Viability Assay[1] Cell Line: AC16 cells. Concentration: 1, 5, 10, or 20 μM. Incubation Time: 0, 24, or 48 hours. Result: Inhibited AC16 cells viability (20 μM).

[In Vivo]

Spiraeoside (50 mg/kg, p.o.) shows ulcer preventive ability[2]. Animal Model: Male Wistar rats (6-8 weeks old)[2]. Dosage: 50 mg/kg. Administration: Oral gavage an hour before inducing the lesions. Result: Decreased severity of the formed lesions.

[References]

[1]. Hongyang Liu, et al. Spiraeoside protects human cardiomyocytes against high glucose-induced injury, oxidative stress, and apoptosis by activation of PI3K/Akt/Nrf2 pathway. J Biochem Mol Toxicol. 2020 Oct;34(10):e22548.

[2]. Stevan Samardžić, et al. Antioxidant, anti-inflammatory and gastroprotective activity of Filipendula ulmaria (L.) Maxim. and Filipendula vulgaris Moench. J Ethnopharmacol. 2018 Mar 1;213:132-137.

Chemical & Physical Properties

[ Density]:
1.809g/cm3

[ Boiling Point ]:
835.6ºC at 760mmHg

[ Melting Point ]:
209-211ºC

[ Molecular Formula ]:
C₂₁H₂₀O₁₂

[ Molecular Weight ]:
464.37600

[ Flash Point ]:
294.6ºC

[ Exact Mass ]:
464.09500

[ PSA ]:
210.51000

[ Vapour Pressure ]:
1.28E-29mmHg at 25°C

[ Index of Refraction ]:
1.774

[ Storage condition ]:
?20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ3095000

CHEMICAL NAME :: 4H-1-Benzopyran-4-one, 2-(4-(beta-D-glucopyranosyloxy)-3-hydroxyphenyl)-3,5, 7-trihydroxy-

CAS REGISTRY NUMBER :: 20229-56-5

LAST UPDATED :: 199503

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C21-H20-C12

MOLECULAR WEIGHT :: 416.53

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 50 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 246,205,1991

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

The crystal structure of human cytosolic beta-glucosidase unravels the substrate aglycone specificity of a family 1 glycoside hydrolase.

J. Mol. Biol. 370(5) , 964-75, (2007)

Human cytosolic beta-glucosidase (hCBG) is a xenobiotic-metabolizing enzyme that hydrolyses certain flavonoid glucosides, with specificity depending on the aglycone moiety, the type of sugar and the l...

Flavonoid glycosides inhibit oral cancer cell proliferation--role of cellular uptake and hydrolysis to the aglycones.

J. Pharm. Pharmacol. 57(8) , 1037-42, (2005)

Epidemiologic evidence supports the view that dietary flavonoids exert protective effects in oral diseases, including cancer. However, the dietary forms of flavonoids, the flavonoid glycosides, are th...

Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver beta-glucosidase activity.

FEBS Lett. 436(1) , 71-5, (1998)

Flavonoid and isoflavonoid glycosides are common dietary phenolics which may be absorbed from the small intestine of humans. The ability of cell-free extracts from human small intestine and liver to d...