Tubeimoside III

CAS# 115810-13-4

Tubeimoside III

Catalog No. BCN2956----Order now to get a substantial discount!

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Quality Control of Tubeimoside III

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Chemical structure

Tubeimoside III

3D structure

Chemical Properties of Tubeimoside III

Cas No. 115810-13-4 SDF Download SDF
PubChem ID 5489425 Appearance Powder
Formula C64H100O31 M.Wt 1365.5
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms Tubeimoside C
Solubility Soluble in DMSO and methanol; insoluble in water
SMILES CC1C2C(C(C(O1)OC3C(C(COC3OC(=O)C45CCC(CC4C6=CCC7C(C6(CC5O)C)(CCC8C7(CC(C(C8(C)CO)OC9C(C(C(C(O9)CO)O)O)OC1C(C(C(C(O1)COC(=O)CC(CC(=O)O2)(C)O)O)O)O)O)C)C)(C)C)O)O)O)OC1C(C(C(CO1)O)O)O
Standard InChIKey MTICHQXHYUJVDV-UHFFFAOYSA-N
Standard InChI InChI=1S/C64H100O31/c1-25-47-48(91-52-44(79)38(73)29(68)21-85-52)46(81)54(87-25)92-49-39(74)30(69)22-86-55(49)95-57(82)64-14-13-58(2,3)15-27(64)26-9-10-34-60(5)16-28(67)51(61(6,24-66)33(60)11-12-62(34,7)63(26,8)17-35(64)70)94-56-50(43(78)40(75)31(20-65)88-56)93-53-45(80)42(77)41(76)32(89-53)23-84-36(71)18-59(4,83)19-37(72)90-47/h9,25,27-35,38-56,65-70,73-81,83H,10-24H2,1-8H3
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 Tubeimoside III

The bulbs of Bolbostemma paniculatum

Biological Activity of Tubeimoside III

DescriptionTubeimoside III has anti-inflammatory, anti-tumor, and anti-tumorigenic activities, stronger than those of tubeimoside II. It has acute toxicity, stronger than that of tubeimoside II.
TargetsImmunology & Inflammation related
In vivo

Structure-activity relationship of tubeimosides in anti-inflammatory, antitumor, and antitumor-promoting effects.[Pubmed: 11743898]

Acta Pharmacol Sin. 2001 May;22(5):463-8.

To study structure-activity relationship of tubeimosides isolated from Bolbostemma paniculatum for their anti-inflammatory, antitumor, and antitumor-promoting effects.
METHODS AND RESULTS:
Tubeimoside I, Tubeimoside II, and Tubeimoside III were isolated from tubers of Bolbostemma paniculatum (Maxim) Franquet (Cucurbitaceae), a Chinese folk medicine,"Tubeimu", and their anti-inflammatory, anti-tumor, anti-tumorigenic activities, and acute toxicity were studied in vivo. Tubeimoside I, Tubeimoside II, and Tubeimoside III are all natural analogues of oleanane type of triterpenoid saponins from the same medicinal plant, and all show anti-inflammatory, antitumor, and antitumor-promo ting effects. However, the anti-inflammatory, anti-tumor, and anti-tumorigenic activities of Tubeimoside II are stronger than those of tubeimoside I, and the acute toxicity of Tubeimoside II is lower than that of tubeimoside I; the anti-inflammatory, anti-tumor, and anti-tumorigenic activities of Tubeimoside III are stronger than those of Tubeimoside II, and the acute toxicity of Tubeimoside III is also stronger than that of Tubeimoside II.
CONCLUSIONS:
C-16 hydroxyl group of Tubeimoside II plays an important role in enhancing biological activity of Tubeimoside II and in decreasing its toxicity. The difference of chemical structure in B and/or C position between tubeimosides III and II plays an important role in enhancing biological activity and toxicity of Tubeimoside III. Therefore tubeimosidre II may be the most promising agent for cancer chemoprevention and chemotherapy among tubeimosides I, II, and III.

Inhibition of the tumor promoting action of 12-O-tetradecanoylphorbol-13-acetate by tubeimoside III isolated from Bolbostemma paniculatum.[Pubmed: 8603483]

Carcinogenesis. 1995 Dec;16(12):3045-8.


METHODS AND RESULTS:
As tubeimoside I isolated from Bolbostemma paniculatum (Maxim.) Franquet (Cucurbitaceae) has been shown to suppress tumor promoter effects, Tubeimoside III from the same plant was tested in vitro and in vivo against the action of the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA). Tubeimoside III, the natural analog of tubeimoside I, also had an anti-inflammatory effect on mouse ear edema induced by arachidonic acid and TPA and a potent anti-tumor promoting effect on two-stage carcinogenesis of mouse skin after topical application. However, the important difference in bioactivities between tubeimosides I and III is the non-activity of Tubeimoside III as an inhibitor of tumor promotion if administered orally.
CONCLUSIONS:
Differences in metabolism connected with different routes of the compound may be one of a number of explanations of the important difference.

Tubeimoside III Dilution Calculator

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Tubeimoside III Molarity Calculator

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Preparing Stock Solutions of Tubeimoside III

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.7323 mL 3.6617 mL 7.3233 mL 14.6466 mL 18.3083 mL
5 mM 0.1465 mL 0.7323 mL 1.4647 mL 2.9293 mL 3.6617 mL
10 mM 0.0732 mL 0.3662 mL 0.7323 mL 1.4647 mL 1.8308 mL
50 mM 0.0146 mL 0.0732 mL 0.1465 mL 0.2929 mL 0.3662 mL
100 mM 0.0073 mL 0.0366 mL 0.0732 mL 0.1465 mL 0.1831 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 Tubeimoside III

Structure-activity relationship of tubeimosides in anti-inflammatory, antitumor, and antitumor-promoting effects.[Pubmed:11743898]

Acta Pharmacol Sin. 2001 May;22(5):463-8.

AIM: To study structure-activity relationship of tubeimosides isolated from Bolbostemma paniculatum for their anti-inflammatory, antitumor, and antitumor-promoting effects. METHODS: Tubeimosides I, II, and III were isolated from tubers of Bolbostemma paniculatum (Maxim) Franquet (Cucurbitaceae), a Chinese folk medicine,"Tubeimu", and their anti-inflammatory, anti-tumor, anti-tumorigenic activities, and acute toxicity were studied in vivo. RESULTS: Tubeimosides I, II, and III are all natural analogues of oleanane type of triterpenoid saponins from the same medicinal plant, and all show anti-inflammatory, antitumor, and antitumor-promo ting effects. However, the anti-inflammatory, anti-tumor, and anti-tumorigenic activities of tubeimoside II are stronger than those of tubeimoside I, and the acute toxicity of tubeimoside II is lower than that of tubeimoside I; the anti-inflammatory, anti-tumor, and anti-tumorigenic activities of Tubeimoside III are stronger than those of tubeimoside II, and the acute toxicity of Tubeimoside III is also stronger than that of tubeimoside II. CONCLUSION: C-16 hydroxyl group of tubeimoside II plays an important role in enhancing biological activity of tubeimoside II and in decreasing its toxicity. The difference of chemical structure in B and/or C position between tubeimosides III and II plays an important role in enhancing biological activity and toxicity of Tubeimoside III. Therefore tubeimosidre II may be the most promising agent for cancer chemoprevention and chemotherapy among tubeimosides I, II, and III.

Inhibition of the tumor promoting action of 12-O-tetradecanoylphorbol-13-acetate by tubeimoside III isolated from Bolbostemma paniculatum.[Pubmed:8603483]

Carcinogenesis. 1995 Dec;16(12):3045-8.

As tubeimoside I isolated from Bolbostemma paniculatum (Maxim.) Franquet (Cucurbitaceae) has been shown to suppress tumor promoter effects, Tubeimoside III from the same plant was tested in vitro and in vivo against the action of the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA). Tubeimoside III, the natural analog of tubeimoside I, also had an anti-inflammatory effect on mouse ear edema induced by arachidonic acid and TPA and a potent anti-tumor promoting effect on two-stage carcinogenesis of mouse skin after topical application. However, the important difference in bioactivities between tubeimosides I and III is the non-activity of Tubeimoside III as an inhibitor of tumor promotion if administered orally. Differences in metabolism connected with different routes of the compound may be one of a number of explanations of the important difference.

Description

Tubeimoside III, a triterpenoid saponin isolated from a Chinese folk medicine"Tubeimu", shows anti-inflammatory, anti-tumor, anti-tumorigenic activities, and acute toxicity in vivo.

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