Tubuloside A

CAS# 112516-05-9

Tubuloside A

Catalog No. BCN2806----Order now to get a substantial discount!

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Quality Control of Tubuloside A

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Chemical structure

Tubuloside A

3D structure

Chemical Properties of Tubuloside A

Cas No. 112516-05-9 SDF Download SDF
PubChem ID 21637830 Appearance Powder
Formula C37H48O21 M.Wt 828.76
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Solubility Soluble in methanol; insoluble in water
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
SMILES CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C)OCCC3=CC(=C(C=C3)O)O)COC4C(C(C(C(O4)CO)O)O)O)OC(=O)C=CC5=CC(=C(C=C5)O)O)O)O)O
Standard InChIKey KZLDMAIXPXOZCX-BBQAUMBQSA-N
Standard InChI 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
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 Tubuloside A

The rhizomes of Cistanche tubulosa (Schenk) Wight

Biological Activity of Tubuloside A

DescriptionTubuloside A has anti-inflammatory, antioxidative and hepatoprotective activities. Tubuloside A shows stronger free radical scavenging activities than alpha-tocopherol on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and xanthine/xanthine oxidase (XOD) generated superoxide anion radical (O2-.).
TargetsNADPH-oxidase | NOS | NO | TNF-α
In vitro

Studies on the Tissue Culture of Cistanche Plants: I. Callus Induction and Shoot Differentiation from the Seed of Cistanche tubulosa Wight[Reference: WebLink]

Plant Biotechnology 12(1), 46-54, 1995-04-01

Cistanche tubulosa Wight. is an important herbal medicine including such phenylethanoide glycosides as echinacoside (E), Tubuloside A (TA), acteoside (A) and 2′-acetylacteoside (2′AA), and is a holoparasitic plant distributed in a wide range from the North African to Chinese in and and semi arid regions.
METHODS AND RESULTS:
In this plant, seed germination occured without a host plant by the addition of gibberellic acid to the medium and the removal of the seed coat. Callus were induced on 1/2MS medium containing 2.5mg/l indol-3-acetic acid and 0.5mg/l kinetin, and with chilling treatment (at 4°C for 3 months) of the seeds. With this condition, a shoot differentiated from the callus in 6 weeks, but a parasitic root did not form. The shape of the vascular bundle of the shoot and that of the mother plant was slightly different.The largest value for phenylethanoide glycosides contained in the shoot was 10 fold that of the mother plant.

Inhibition of nitric oxide by phenylethanoids in activated macrophages.[Pubmed: 10913595]

Eur J Pharmacol. 2000 Jul 14;400(1):137-44.

Nitric oxide (NO) is one of the pro-inflammatory molecules. Some phenylethanoids have been previously shown to possess anti-inflammatory effects.
METHODS AND RESULTS:
Seven phenylethanoids from the stems of Cistanche deserticola, viz. isoacteoside, tubuloside B, acteoside, 2'-O-acetylacteoside, echinacoside, cistanoside A and Tubuloside A, were tested for their effect on NO radical generation by activated murine macrophages. At the concentration of 100-200 microM, all the phenylethanoids reduced (6.3-62.3%) nitrite accumulation in lipopolysaccharide (0.1 microgram/ml)-stimulated J774.1 cells. At 200 microM, they inhibited by 32.2-72.4% nitrite accumulation induced by lipopolysaccharide (0.1 microgram/ml)/interferon-gamma (100 U/ml) in mouse peritoneal exudate macrophages. However, these compounds did not affect the expression of inducible nitric oxide (iNOS) mRNA, the iNOS protein level, or the iNOS activity in lipopolysaccharide-stimulated J774.1 cells. Instead, they showed a clear scavenging effect (6.9-43.9%) at the low concentrations of 2-10 microM of about 12 microM nitrite generated from an NO donor, 1-propanamine-3-hydroxy-2-nitroso-1-propylhydrazino (PAPA NONOate).
CONCLUSIONS:
These results indicate that the phenylethanoids have NO radical-scavenging activity, which possibly contributes to their anti-inflammatory effects.

Protocol of Tubuloside A

Cell Research

Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa.[Pubmed: 20159656 ]

Bioorg Med Chem. 2010 Mar 1;18(5):1882-90.

The methanolic extract from fresh stems of Cistanche tubulosa (Orobanchaceae) was found to show hepatoprotective effects against D-galactosamine (D-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice.
METHODS AND RESULTS:
From the extract, three new phenylethanoid oligoglycosides, kankanosides H(1) (1), H(2) (2), and I (3), were isolated together with 16 phenylethanoid glycosides (4-19) and two acylated oligosugars (20, 21). The structures of 1-3 were determined on the basis of spectroscopic properties as well as of chemical evidence. Among the isolates, echinacoside (4, IC(50)=10.2 microM), acteoside (5, 4.6 microM), isoacteoside (6, 5.3 microM), 2'-acetylacteoside (8, 4.8 microM), and Tubuloside A (10, 8.6 microM) inhibited D-GalN-induced death of hepatocytes. These five isolates, 4 (31.1 microM), 5 (17.8 microM), 6 (22.7 microM), 8 (25.7 microM), and 10 (23.2 microM), and cistantubuloside B(1) (11, 21.4 microM) also reduced TNF-alpha-induced cytotoxicity in L929 cells. Moreover, principal constituents (4-6) exhibited in vivo hepatoprotective effects at doses of 25-100mg/kg, po.

Structure Identification
Biol Pharm Bull. 1996 Dec;19(12):1580-5.

Antioxidative effects of phenylethanoids from Cistanche deserticola.[Pubmed: 8996643]


METHODS AND RESULTS:
The acetone-H2O (9:1) extract from the stem of Cistanche deserticola showed a strong free radical scavenging activity. Nine major phenylethanoid compounds were isolated from this extract. They were identified by NMR as acteoside, isoacteoside, 2'-acetylacteoside, tubuloside B, echinacoside, Tubuloside A, syringalide A 3'-alpha-rhamnopyranoside, cistanoside A and cistanoside F. All of these compounds showed stronger free radical scavenging activities than alpha-tocopherol on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and xanthine/xanthine oxidase (XOD) generated superoxide anion radical (O2-.). Among the nine compounds, isoacteoside and tubuloside B, whose caffeoyl moiety is at 6'-position of the glucose, showed an inhibitory effect on XOD. We further studied the effects of these phenylethanoids on the lipid peroxidation in rat liver microsomes induced by enzymatic and non-enzymatic methods. As expected, each of them exhibited significant inhibition on both ascorbic acid/Fe2+ and ADP/NADPH/Fe3+ induced lipid peroxidation in rat liver microsomes, which were more potent than alpha-tocopherol of caffeic acid.
CONCLUSIONS:
The antioxidative effect was found to be potentiated by an increase in the number of phenolic hydroxyl groups in the molecule.

Tubuloside A Dilution Calculator

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Tubuloside A Molarity Calculator

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Preparing Stock Solutions of Tubuloside A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.2066 mL 6.0331 mL 12.0662 mL 24.1324 mL 30.1655 mL
5 mM 0.2413 mL 1.2066 mL 2.4132 mL 4.8265 mL 6.0331 mL
10 mM 0.1207 mL 0.6033 mL 1.2066 mL 2.4132 mL 3.0166 mL
50 mM 0.0241 mL 0.1207 mL 0.2413 mL 0.4826 mL 0.6033 mL
100 mM 0.0121 mL 0.0603 mL 0.1207 mL 0.2413 mL 0.3017 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 Tubuloside A

Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa.[Pubmed:20159656]

Bioorg Med Chem. 2010 Mar 1;18(5):1882-90.

The methanolic extract from fresh stems of Cistanche tubulosa (Orobanchaceae) was found to show hepatoprotective effects against D-galactosamine (D-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. From the extract, three new phenylethanoid oligoglycosides, kankanosides H(1) (1), H(2) (2), and I (3), were isolated together with 16 phenylethanoid glycosides (4-19) and two acylated oligosugars (20, 21). The structures of 1-3 were determined on the basis of spectroscopic properties as well as of chemical evidence. Among the isolates, echinacoside (4, IC(50)=10.2 microM), acteoside (5, 4.6 microM), isoacteoside (6, 5.3 microM), 2'-acetylacteoside (8, 4.8 microM), and Tubuloside A (10, 8.6 microM) inhibited D-GalN-induced death of hepatocytes. These five isolates, 4 (31.1 microM), 5 (17.8 microM), 6 (22.7 microM), 8 (25.7 microM), and 10 (23.2 microM), and cistantubuloside B(1) (11, 21.4 microM) also reduced TNF-alpha-induced cytotoxicity in L929 cells. Moreover, principal constituents (4-6) exhibited in vivo hepatoprotective effects at doses of 25-100mg/kg, po.

Inhibition of nitric oxide by phenylethanoids in activated macrophages.[Pubmed:10913595]

Eur J Pharmacol. 2000 Jul 14;400(1):137-44.

Nitric oxide (NO) is one of the pro-inflammatory molecules. Some phenylethanoids have been previously shown to possess anti-inflammatory effects. Seven phenylethanoids from the stems of Cistanche deserticola, viz. isoacteoside, tubuloside B, acteoside, 2'-O-acetylacteoside, echinacoside, cistanoside A and Tubuloside A, were tested for their effect on NO radical generation by activated murine macrophages. At the concentration of 100-200 microM, all the phenylethanoids reduced (6.3-62.3%) nitrite accumulation in lipopolysaccharide (0.1 microgram/ml)-stimulated J774.1 cells. At 200 microM, they inhibited by 32.2-72.4% nitrite accumulation induced by lipopolysaccharide (0.1 microgram/ml)/interferon-gamma (100 U/ml) in mouse peritoneal exudate macrophages. However, these compounds did not affect the expression of inducible nitric oxide (iNOS) mRNA, the iNOS protein level, or the iNOS activity in lipopolysaccharide-stimulated J774.1 cells. Instead, they showed a clear scavenging effect (6.9-43.9%) at the low concentrations of 2-10 microM of about 12 microM nitrite generated from an NO donor, 1-propanamine-3-hydroxy-2-nitroso-1-propylhydrazino (PAPA NONOate). These results indicate that the phenylethanoids have NO radical-scavenging activity, which possibly contributes to their anti-inflammatory effects.

Antioxidative effects of phenylethanoids from Cistanche deserticola.[Pubmed:8996643]

Biol Pharm Bull. 1996 Dec;19(12):1580-5.

The acetone-H2O (9:1) extract from the stem of Cistanche deserticola showed a strong free radical scavenging activity. Nine major phenylethanoid compounds were isolated from this extract. They were identified by NMR as acteoside, isoacteoside, 2'-acetylacteoside, tubuloside B, echinacoside, Tubuloside A, syringalide A 3'-alpha-rhamnopyranoside, cistanoside A and cistanoside F. All of these compounds showed stronger free radical scavenging activities than alpha-tocopherol on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and xanthine/xanthine oxidase (XOD) generated superoxide anion radical (O2-.). Among the nine compounds, isoacteoside and tubuloside B, whose caffeoyl moiety is at 6'-position of the glucose, showed an inhibitory effect on XOD. We further studied the effects of these phenylethanoids on the lipid peroxidation in rat liver microsomes induced by enzymatic and non-enzymatic methods. As expected, each of them exhibited significant inhibition on both ascorbic acid/Fe2+ and ADP/NADPH/Fe3+ induced lipid peroxidation in rat liver microsomes, which were more potent than alpha-tocopherol of caffeic acid. The antioxidative effect was found to be potentiated by an increase in the number of phenolic hydroxyl groups in the molecule.

Description

Tubuloside A is a phenylethanoid glycoside with antioxidative effect and hepatoprotective activity.

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