2'-Acetylacteoside

CAS# 94492-24-7

2'-Acetylacteoside

Catalog No. BCN3409----Order now to get a substantial discount!

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Quality Control of 2'-Acetylacteoside

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Chemical structure

2'-Acetylacteoside

3D structure

Chemical Properties of 2'-Acetylacteoside

Cas No. 94492-24-7 SDF Download SDF
PubChem ID 21629996 Appearance White powder
Formula C31H38O16 M.Wt 666.6
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Synonyms 2'-Acetylverbascoside
Solubility Soluble in methan
Chemical Name [(2R,3R,4S,5R,6R)-5-acetyloxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
SMILES CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C)OCCC3=CC(=C(C=C3)O)O)CO)OC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)O
Standard InChIKey ALERZNQPBWWLMW-OMRKUVHCSA-N
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 2'-Acetylacteoside

1 Cistanche sp.

Biological Activity of 2'-Acetylacteoside

Description2'-Acetylacteoside has antioxidative, hepatoprotective, and neuroprotective activities. 2'-Acetylacteoside (0.071 uM) demonstrates potent rat lens aldose reductase inhibitory activity; it can significantly suppress NADPH/CCl4-induced lipid peroxidation in rat liver microsomes.
TargetsNADPH-oxidase
In vitro

Hepatoprotective activity of phenylethanoids from Cistanche deserticola.[Pubmed: 9525102 ]

Planta Med. 1998 Mar;64(2):120-5.


METHODS AND RESULTS:
Four phenylethanoids isolated from the stems of Cistanche deserticola, acteoside (1), 2'-Acetylacteoside (2), isoacteoside (3) and tubuloside B (4), significantly suppressed NADPH/CCl4-induced lipid peroxidation in rat liver microsomes. Addition of them to primary cultured rat hepatocytes efficiently prevented cell damage induced by exposure to CCl4 or D-galactosamine (D-GalN).
CONCLUSIONS:
Acteoside (1) further showed pronounced anti-hepatotoxic activity against CCl4 in vivo.

In vitro neuroprotective activities of phenylethanoid glycosides from Callicarpa dichotoma.[Pubmed: 16142646 ]

Planta Med. 2005 Aug;71(8):778-80.


METHODS AND RESULTS:
Ten phenylethanoid glycosides, forsythoside B, acteoside, 2'-Acetylacteoside, poliumoside, brandioside, echinacoside, isoacteoside, cistanoside H and E-tubuloside E as well as a new compound, Z-tubuloside E, were isolated from the n-BuOH fraction of Callicarpa dichotoma Raeuschel (Verbenaceae) by bioactivity-guided fractionation using glutamate-injured primary cultures of rat cortical cells as a screening system.
CONCLUSIONS:
These phenylethanoid glycosides significantly attenuated glutamate-induced neurotoxicity at concentrations ranging from 0.1 to 10 microM.

Protocol of 2'-Acetylacteoside

Animal Research

Acylated phenylethanoid glycosides, echinacoside and acteoside from Cistanche tubulosa, improve glucose tolerance in mice.[Pubmed: 24748124]

J Nat Med. 2014 Jul;68(3):561-6.


METHODS AND RESULTS:
Acylated phenylethanoid glycosides, echinacoside (1) and acteoside (2), principal constituents in stems of Cistanche tubulosa (Orobanchaceae), inhibited the increase in postprandial blood glucose levels in starch-loaded mice at doses of 250-500 mg/kg p.o. These compounds (1 and 2) also significantly improved glucose tolerance in starch-loaded mice after 2 weeks of continuous administration at doses of 125 and/or 250 mg/kg/day p.o. without producing significant changes in body weight or food intake.
CONCLUSIONS:
In addition, several constituents from C. tubulosa, including 1 (IC50 = 3.1 μM), 2 (1.2 μM), isoacteoside (3, 4.6 μM), 2'-Acetylacteoside (4, 0.071 μM), tubulosides A (5, 8.8 μM) and B (9, 4.0 μM), syringalide A 3-O-α-L-rhamnopyranoside (10, 1.1 μM), campneoside I (13, 0.53 μM), and kankanoside J1 (14, 9.3 μM), demonstrated potent rat lens aldose reductase inhibitory activity. In particular, the potency of compound 4 was similar to that of epalrestat (0.072 μM), a clinical aldose reductase inhibitor.

Structure Identification
Planta Med. 2001 Aug;67(6):520-2.

Purification of phenylethanoids from Brandisia hancei and the antiproliferative effects on aortic smooth muscle.[Pubmed: 11509971 ]


METHODS AND RESULTS:
The present study describes the isolation and purification of acteoside, 2'-Acetylacteoside, poliumoside and brandioside, four phenylethanoid glycosides from Brandisia hancei. We examined their effects on the proliferation of cultured A7r5 rat aortic smooth muscle cells. The proliferative response was measured from the [(3)H]-thymidine incorporation into DNA. All four glycosides suppressed the proliferative response in the presence of 2 % or 5 % fetal bovine serum in a concentration-dependent manner. The rank order of effectiveness for inhibition of cell proliferation was: brandioside > or = poliumoside > 2'-Acetylacteoside > or = acteoside. The acetyl group at position 2' of glucose does not seem necessary for the anti-proliferative effects of acteoside and 2'-Acetylacteoside, while the hydroxy groups of the aromatic rings appear to play a role.
CONCLUSIONS:
Inhibition of smooth muscle cell proliferation by phenylethanoids indicates that these compounds may have preventative effects on arteriosclerosis.

Zhong Yao Cai. 2009 Jul;32(7):1067-9.

Structure-activity relationships of phenylethanoid glycosides in plants of Cistanche salsa on antioxidative activity.[Pubmed: 19873735]

To study the structure-activity relationships of phenylethanoid glycosides in plants of Cistanche salsa on antioxidative activity.
METHODS AND RESULTS:
By the assay systems of DPPH*, the antioxidant activity of six phenylethanoid glycosides from plants of Cistanche salsa was determined to investigate the relationship between the antioxidant activities and phenylethanoid glycosides's structural characteristics. The antioxidative activity of phenylethanoid glycosides was variant with dose-dependent effect. The sequence of the strength of the antioxidative activity of the six components was shown to be 2'-Acetylacteoside > Acteoside > or = Tubuloside B > or = Isoacteoside > Echinacoside > Cistanoside A.
CONCLUSIONS:
The antioxidative activity of phenylethanoid glycosides is related to the number of phenolic hydroxyl, steric hindrance, 2-acetyl on the middle glucopyranose, and the location of phenolic hydroxyl. Additionally, it may be related to the alpha, beta-unsaturated ketone of phenl-2-propenoyl.

2'-Acetylacteoside Dilution Calculator

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2'-Acetylacteoside Molarity Calculator

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Preparing Stock Solutions of 2'-Acetylacteoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.5002 mL 7.5008 mL 15.0015 mL 30.003 mL 37.5038 mL
5 mM 0.3 mL 1.5002 mL 3.0003 mL 6.0006 mL 7.5008 mL
10 mM 0.15 mL 0.7501 mL 1.5002 mL 3.0003 mL 3.7504 mL
50 mM 0.03 mL 0.15 mL 0.3 mL 0.6001 mL 0.7501 mL
100 mM 0.015 mL 0.075 mL 0.15 mL 0.3 mL 0.375 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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References on 2'-Acetylacteoside

In vitro neuroprotective activities of phenylethanoid glycosides from Callicarpa dichotoma.[Pubmed:16142646]

Planta Med. 2005 Aug;71(8):778-80.

Ten phenylethanoid glycosides, forsythoside B, acteoside, 2'-acetylacteoside, poliumoside, brandioside, echinacoside, isoacteoside, cistanoside H and E-tubuloside E as well as a new compound, Z-tubuloside E, were isolated from the n-BuOH fraction of Callicarpa dichotoma Raeuschel (Verbenaceae) by bioactivity-guided fractionation using glutamate-injured primary cultures of rat cortical cells as a screening system. These phenylethanoid glycosides significantly attenuated glutamate-induced neurotoxicity at concentrations ranging from 0.1 to 10 microM.

Hepatoprotective activity of phenylethanoids from Cistanche deserticola.[Pubmed:9525102]

Planta Med. 1998 Mar;64(2):120-5.

Four phenylethanoids isolated from the stems of Cistanche deserticola, acteoside (1), 2'-acetylacteoside (2), isoacteoside (3) and tubuloside B (4), significantly suppressed NADPH/CCl4-induced lipid peroxidation in rat liver microsomes. Addition of them to primary cultured rat hepatocytes efficiently prevented cell damage induced by exposure to CCl4 or D-galactosamine (D-GalN). Acteoside (1) further showed pronounced anti-hepatotoxic activity against CCl4 in vivo.

Acylated phenylethanoid glycosides, echinacoside and acteoside from Cistanche tubulosa, improve glucose tolerance in mice.[Pubmed:24748124]

J Nat Med. 2014 Jul;68(3):561-6.

Acylated phenylethanoid glycosides, echinacoside (1) and acteoside (2), principal constituents in stems of Cistanche tubulosa (Orobanchaceae), inhibited the increase in postprandial blood glucose levels in starch-loaded mice at doses of 250-500 mg/kg p.o. These compounds (1 and 2) also significantly improved glucose tolerance in starch-loaded mice after 2 weeks of continuous administration at doses of 125 and/or 250 mg/kg/day p.o. without producing significant changes in body weight or food intake. In addition, several constituents from C. tubulosa, including 1 (IC50 = 3.1 muM), 2 (1.2 muM), isoacteoside (3, 4.6 muM), 2'-acetylacteoside (4, 0.071 muM), tubulosides A (5, 8.8 muM) and B (9, 4.0 muM), syringalide A 3-O-alpha-L-rhamnopyranoside (10, 1.1 muM), campneoside I (13, 0.53 muM), and kankanoside J1 (14, 9.3 muM), demonstrated potent rat lens aldose reductase inhibitory activity. In particular, the potency of compound 4 was similar to that of epalrestat (0.072 muM), a clinical aldose reductase inhibitor.

Purification of phenylethanoids from Brandisia hancei and the antiproliferative effects on aortic smooth muscle.[Pubmed:11509971]

Planta Med. 2001 Aug;67(6):520-2.

The present study describes the isolation and purification of acteoside, 2'-acetylacteoside, poliumoside and brandioside, four phenylethanoid glycosides from Brandisia hancei. We examined their effects on the proliferation of cultured A7r5 rat aortic smooth muscle cells. The proliferative response was measured from the [(3)H]-thymidine incorporation into DNA. All four glycosides suppressed the proliferative response in the presence of 2 % or 5 % fetal bovine serum in a concentration-dependent manner. The rank order of effectiveness for inhibition of cell proliferation was: brandioside > or = poliumoside > 2'-acetylacteoside > or = acteoside. The acetyl group at position 2' of glucose does not seem necessary for the anti-proliferative effects of acteoside and 2'-acetylacteoside, while the hydroxy groups of the aromatic rings appear to play a role. Inhibition of smooth muscle cell proliferation by phenylethanoids indicates that these compounds may have preventative effects on arteriosclerosis.

[Structure-activity relationships of phenylethanoid glycosides in plants of Cistanche salsa on antioxidative activity].[Pubmed:19873735]

Zhong Yao Cai. 2009 Jul;32(7):1067-9.

OBJECTIVE: To study the structure-activity relationships of phenylethanoid glycosides in plants of Cistanche salsa on antioxidative activity. METHODS: By the assay systems of DPPH*, the antioxidant activity of six phenylethanoid glycosides from plants of Cistanche salsa was determined to investigate the relationship between the antioxidant activities and phenylethanoid glycosides's structural characteristics. RESULTS: The antioxidative activity of phenylethanoid glycosides was variant with dose-dependent effect. The sequence of the strength of the antioxidative activity of the six components was shown to be 2'-Acetylacteoside > Acteoside > or = Tubuloside B > or = Isoacteoside > Echinacoside > Cistanoside A. CONCLUSION: The antioxidative activity of phenylethanoid glycosides is related to the number of phenolic hydroxyl, steric hindrance, 2-acetyl on the middle glucopyranose, and the location of phenolic hydroxyl. Additionally, it may be related to the alpha, beta-unsaturated ketone of phenl-2-propenoyl.

Description

2'-Acetylacteoside is a phenylethanoid glycoside isolated from Brandisia hancei, inhibits free radical-induced hemolysis of red blood cells and exhibits free radical scavenging activity.

Keywords:

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