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Tubuloside A

Cat No.:V33821 Purity: ≥98%
Tubuloside A is a phenylethanoid glycoside with antioxidant and hepatoprotective activity.
Tubuloside A
Tubuloside A Chemical Structure CAS No.: 112516-05-9
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Tubuloside A is a phenylethanoid glycoside with antioxidant and hepatoprotective activity.
Biological Activity I Assay Protocols (From Reference)
Targets
Antioxidant / Free radical scavenger
Inhibitor of lipid peroxidation
ln Vitro
Phenylethanol glycoside tubuloside A has hepatoprotective and antioxidant properties [1][2]. Hepatocyte mortality produced by D-GalN can be inhibited by tubuloside A (8.6 μM) [2].
- Tubuloside A demonstrated DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity with an IC₅₀ of 3.34 µM, which was stronger than α-tocopherol (IC₅₀ = 10.2 µM) and caffeic acid (IC₅₀ = 4.79 µM). [1]
- Tubuloside A showed scavenging activity against xanthine/xanthine oxidase (XOD)-generated superoxide anion radical (O₂⁻) with an IC₅₀ of 3.17 µM. This activity was stronger than α-tocopherol (IC₅₀ > 10 µM) but weaker than caffeic acid (IC₅₀ = 1.82 µM). [1]
- Tubuloside A did not show an inhibitory effect on xanthine oxidase (XOD) activity at the tested concentrations (25-200 µM). [1]
- Tubuloside A significantly inhibited ascorbic acid/Fe²⁺-induced lipid peroxidation in rat liver microsomes with an IC₅₀ of 9.3 µM. Its activity was stronger than caffeic acid (IC₅₀ = 32.2 µM) and much stronger than α-tocopherol (IC₅₀ > 100 µM). [1]
- Tubuloside A significantly inhibited ADP/NADPH/Fe³⁺-induced lipid peroxidation in rat liver microsomes with an IC₅₀ of 47.6 µM. Its activity was stronger than caffeic acid (IC₅₀ = 214.0 µM) and much stronger than α-tocopherol (IC₅₀ > 1000 µM). [1]
Enzyme Assay
The inhibitory effect of Tubuloside A on xanthine oxidase (XOD) activity was estimated. A reaction mixture consisting of phosphate buffer (pH 7.5), XOD solution, and the sample solution was pre-incubated. Xanthine solution was then added to start the enzyme reaction. After incubation, the reaction was terminated by adding HCl, and the absorbance of the reaction mixture was measured at 295 nm to determine the concentration of uric acid formed. The inhibitory effect was expressed as the percent inhibition of uric acid formation compared to the control (where water was used instead of the sample solution). [1]
References

[1]. Antioxidative effects of phenylethanoids from Cistanche deserticola. Biol Pharm Bull. 1996 Dec;19(12):1580-5.

[2]. Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa. Bioorg Med Chem. 2010 Mar 1;18(5):1882-90.

Additional Infomation
Tubular glycoside A is an oligosaccharide. It has been reported that tubular glycoside A exists in Cistanche tubulosa, Cistanche phelypaea and Cistanche deserticola, and there are relevant data. Tubular glycoside A is a phenylethanol glycoside that was isolated from the stem of Cistanche deserticola. Its chemical structure is characterized by a caffeoyl group attached to the 4-position of the glucose unit. [1] The antioxidant activity of tubular glycoside A and its related phenylethanol glycosides increases with the number of phenolic hydroxyl groups in the molecule. For example, tubular glycoside A with four phenolic hydroxyl groups exhibits stronger activity. [1] This study suggests that the anti-lipid peroxidation activity of Tubuloside A may involve multiple mechanisms, such as chelating Fe²⁺ or Fe³⁺ ions, scavenging superoxide radicals (O₂⁻) to block free radical chain reactions, and directly scavenging more toxic free radicals, such as hydroxyl radicals and lipid peroxide radicals. [1] Compared with the superoxide anion radical scavenging activity, the DPPH radical scavenging activity sequence of the tested compounds showed better consistency with their anti-lipid peroxidation activity sequence. [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C37H48O21
Molecular Weight
828.7644
Exact Mass
828.268
CAS #
112516-05-9
PubChem CID
21637830
Appearance
Off-white to light yellow solid powder
Density
1.6±0.1 g/cm3
Boiling Point
1045.5±65.0 °C at 760 mmHg
Flash Point
317.7±27.8 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.676
LogP
0.75
Hydrogen Bond Donor Count
11
Hydrogen Bond Acceptor Count
21
Rotatable Bond Count
16
Heavy Atom Count
58
Complexity
1340
Defined Atom Stereocenter Count
15
SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@H](O[C@H]([C@@H]2OC(=O)C)OCCC3=CC(=C(C=C3)O)O)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC(=O)/C=C/C5=CC(=C(C=C5)O)O)O)O)O
InChi Key
KZLDMAIXPXOZCX-BBQAUMBQSA-N
InChi Code
InChI=1S/C37H48O21/c1-15-26(45)28(47)31(50)36(53-15)58-33-32(57-25(44)8-5-17-3-6-19(40)21(42)11-17)24(14-52-35-30(49)29(48)27(46)23(13-38)55-35)56-37(34(33)54-16(2)39)51-10-9-18-4-7-20(41)22(43)12-18/h3-8,11-12,15,23-24,26-38,40-43,45-50H,9-10,13-14H2,1-2H3/b8-5+/t15-,23+,24+,26-,27+,28+,29-,30+,31+,32+,33-,34+,35+,36-,37+/m0/s1
Chemical Name
[(2R,3R,4S,5R,6R)-5-acetyloxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-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
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~50 mg/mL (~60.33 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.02 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (3.02 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (3.02 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.2066 mL 6.0331 mL 12.0662 mL
5 mM 0.2413 mL 1.2066 mL 2.4132 mL
10 mM 0.1207 mL 0.6033 mL 1.2066 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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