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Sagittatoside A

CAS# 118525-35-2

Sagittatoside A

Catalog No. BCN2285----Order now to get a substantial discount!

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Quality Control of Sagittatoside A

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Chemical structure

Sagittatoside A

3D structure

Chemical Properties of Sagittatoside A

Cas No. 118525-35-2 SDF Download SDF
PubChem ID 13916054 Appearance Yellow powder
Formula C33H40O15 M.Wt 676.67
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Icariin-A
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
SMILES CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)O)O)C4=CC=C(C=C4)OC)OC5C(C(C(C(O5)CO)O)O)O)O)O
Standard InChIKey COHHGQPQHHUMDG-WVQJJEIESA-N
Standard InChI InChI=1S/C33H40O15/c1-13(2)5-10-17-18(35)11-19(36)21-24(39)30(28(46-29(17)21)15-6-8-16(43-4)9-7-15)47-33-31(26(41)22(37)14(3)44-33)48-32-27(42)25(40)23(38)20(12-34)45-32/h5-9,11,14,20,22-23,25-27,31-38,40-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25-,26+,27+,31+,32-,33-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Sagittatoside A

The roots of Epimedium brevicornu Maxim

Biological Activity of Sagittatoside A

DescriptionSagittatoside A selectively activates estrogen response element (ERE)-luciferase activity via ERα, and sagittatoside A and icariin induces ERα phosphorylation at serine 118 residue.
TargetsNF-kB | Estrogen receptor | Progestogen receptor
In vitro

Flavonoids from Herba epimedii selectively activate estrogen receptor alpha (ERα) and stimulate ER-dependent osteoblastic functions in UMR-106 cells.[Pubmed: 24607839]

J Steroid Biochem Mol Biol. 2014 Sep;143:141-51.

Total flavonoids in Herba epimedii (HEP) have been demonstrated to protect against bone loss and bone deterioration associated with estrogen deficiency without exerting any uterotrophic effects. However, it is unclear how flavonoids in HEP exert their protective effects on bone and if different flavonoids exert estrogenic actions in bone cells via similar mechanism of actions.
METHODS AND RESULTS:
The present study aims to investigate the bone anabolic effects of four major flavonoids isolated from HEP, namely icariin, baohuoside-I, epimedin B and Sagittatoside A as well as the mechanism involved in mediating their estrogenic actions in rat osteoblastic-like UMR-106 cells. All tested compounds significantly stimulated the cell proliferation rate, alkaline phosphate (ALP) activity and osteoprotegerin (OPG)/receptor activator of nuclear factor κ-B ligand (RANKL) mRNA expression in UMR-106 cells and their effects could be abolished by co-incubation with 10(-6)M ICI 182,780. None of the flavonoids exhibited binding affinities toward ERα and ERβ. However, Sagittatoside A selectively activated estrogen response element (ERE)-luciferase activity via ERα. In addition, icariin and Sagittatoside A induced ERα phosphorylation at serine 118 residue.
CONCLUSIONS:
Taken together, our results indicated that all four flavonoids from HEP stimulated ER-dependent osteoblastic functions in UMR-106 cells, but only two of them appeared to exert their actions by ligand-independent activation of ERα. Our study provides evidence to support the hypothesis that the estrogen-like protective effects on bone by flavonoids are mediated via mechanisms that are distinct from the classical actions of estrogen.

Protocol of Sagittatoside A

Structure Identification
J Sep Sci. 2009 Jan;32(2):275-81.

Effect of stability of internal standard on quantification of 15 flavonoids in Epimedium using CZE.[Pubmed: 19101945]


METHODS AND RESULTS:
A CZE method was developed for the simultaneous determination of 15 flavonoids, including epimedin B, epimedin A, hexandraside F, epimedin C, icariin, sagittatoside B, Sagittatoside A, hexandraside E, 2''-O-rhamnosyl icariside II, baohuoside VII, baohuoside I, caohuoside C, epimedoside C, baohuoside II, and kaempferol-3-O-rhamnoside, in different species of Epimedium, and the effect of stability of internal standard (IS) on quantification was also investigated. As a result, rutin was not available for use as an IS because of its unstable property in sample solution, which suggested that the stability of IS both in standards and sample solution should be considered for the analysis. Using stable daidzein as IS, the analysis was performed within 35 min by using 50 mM borax buffer containing 20% ACN as a modifier (pH 10.0), while separation voltage was 25 kV and temperature was at 30 degrees C.
CONCLUSIONS:
The method was validated to be accurate, simple, and repeatable, and was successfully applied to the analysis of 36 samples from 17 species of Epimedium.

Sagittatoside A Dilution Calculator

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Preparing Stock Solutions of Sagittatoside A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.4778 mL 7.3891 mL 14.7783 mL 29.5565 mL 36.9456 mL
5 mM 0.2956 mL 1.4778 mL 2.9557 mL 5.9113 mL 7.3891 mL
10 mM 0.1478 mL 0.7389 mL 1.4778 mL 2.9557 mL 3.6946 mL
50 mM 0.0296 mL 0.1478 mL 0.2956 mL 0.5911 mL 0.7389 mL
100 mM 0.0148 mL 0.0739 mL 0.1478 mL 0.2956 mL 0.3695 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Sagittatoside A

Sagittatoside A is a natural compound isolated from traditional Chinese herb Yinyanghuo (Herba Epimdii).

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References on Sagittatoside A

Flavonoids from Herba epimedii selectively activate estrogen receptor alpha (ERalpha) and stimulate ER-dependent osteoblastic functions in UMR-106 cells.[Pubmed:24607839]

J Steroid Biochem Mol Biol. 2014 Sep;143:141-51.

Total flavonoids in Herba epimedii (HEP) have been demonstrated to protect against bone loss and bone deterioration associated with estrogen deficiency without exerting any uterotrophic effects. However, it is unclear how flavonoids in HEP exert their protective effects on bone and if different flavonoids exert estrogenic actions in bone cells via similar mechanism of actions. The present study aims to investigate the bone anabolic effects of four major flavonoids isolated from HEP, namely icariin, baohuoside-I, epimedin B and Sagittatoside A as well as the mechanism involved in mediating their estrogenic actions in rat osteoblastic-like UMR-106 cells. All tested compounds significantly stimulated the cell proliferation rate, alkaline phosphate (ALP) activity and osteoprotegerin (OPG)/receptor activator of nuclear factor kappa-B ligand (RANKL) mRNA expression in UMR-106 cells and their effects could be abolished by co-incubation with 10(-6)M ICI 182,780. None of the flavonoids exhibited binding affinities toward ERalpha and ERbeta. However, Sagittatoside A selectively activated estrogen response element (ERE)-luciferase activity via ERalpha. In addition, icariin and Sagittatoside A induced ERalpha phosphorylation at serine 118 residue. Taken together, our results indicated that all four flavonoids from HEP stimulated ER-dependent osteoblastic functions in UMR-106 cells, but only two of them appeared to exert their actions by ligand-independent activation of ERalpha. Our study provides evidence to support the hypothesis that the estrogen-like protective effects on bone by flavonoids are mediated via mechanisms that are distinct from the classical actions of estrogen.

Effect of stability of internal standard on quantification of 15 flavonoids in Epimedium using CZE.[Pubmed:19101945]

J Sep Sci. 2009 Jan;32(2):275-81.

A CZE method was developed for the simultaneous determination of 15 flavonoids, including epimedin B, epimedin A, hexandraside F, epimedin C, icariin, sagittatoside B, Sagittatoside A, hexandraside E, 2''-O-rhamnosyl icariside II, baohuoside VII, baohuoside I, caohuoside C, epimedoside C, baohuoside II, and kaempferol-3-O-rhamnoside, in different species of Epimedium, and the effect of stability of internal standard (IS) on quantification was also investigated. As a result, rutin was not available for use as an IS because of its unstable property in sample solution, which suggested that the stability of IS both in standards and sample solution should be considered for the analysis. Using stable daidzein as IS, the analysis was performed within 35 min by using 50 mM borax buffer containing 20% ACN as a modifier (pH 10.0), while separation voltage was 25 kV and temperature was at 30 degrees C. The method was validated to be accurate, simple, and repeatable, and was successfully applied to the analysis of 36 samples from 17 species of Epimedium.

Description

Sagittatoside A is a natural compound isolated from traditional Chinese herb Yinyanghuo (Herba Epimdii).

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