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21-O-Tigloylgymnemagenin

CAS# 1581276-63-2

21-O-Tigloylgymnemagenin

Catalog No. BCN7854----Order now to get a substantial discount!

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Quality Control of 21-O-Tigloylgymnemagenin

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Chemical structure

21-O-Tigloylgymnemagenin

3D structure

Chemical Properties of 21-O-Tigloylgymnemagenin

Cas No. 1581276-63-2 SDF Download SDF
PubChem ID 124928704 Appearance Powder
Formula C35H56O7 M.Wt 588.81
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(3R,4R,4aR,5S,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-4,5,10-trihydroxy-4a,9-bis(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-3-yl] (E)-2-methylbut-2-enoate
SMILES CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)CO)O)C)CO)O
Standard InChIKey ZVFCKHLBNXUAAD-DQGOMBRUSA-N
Standard InChI InChI=1S/C35H56O7/c1-9-20(2)29(41)42-28-27(40)35(19-37)22(16-30(28,3)4)21-10-11-24-31(5)14-13-25(38)32(6,18-36)23(31)12-15-33(24,7)34(21,8)17-26(35)39/h9-10,22-28,36-40H,11-19H2,1-8H3/b20-9+/t22-,23+,24+,25-,26-,27-,28-,31-,32-,33+,34+,35-/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 21-O-Tigloylgymnemagenin

The

Protocol of 21-O-Tigloylgymnemagenin

Structure Identification
CHEMICAL & PHARMACEUTICAL BULLETIN, 1997, 45(10):1671-1676.

Medicinal foodstuffs. IX. The inhibitors of glucose absorption from the leaves of Gymnema sylvestre R. BR. (Asclepiadaceae): structures of gymnemosides a and b.[Reference: WebLink]

Although the glycosidic fraction from the dried leaves of Gymnema sylvestre R. BR., gymnemic acid, was reported to be effective for diabetes, it showed little inhibitory activity on the increase of serum glucose level in oral glucose-loaded rats.
METHODS AND RESULTS:
From the glycosidic fraction, six triterpene glycosides, gymnemosides a, b, c, d, e, and f, were isolated together with nine known triterpene glycosides. The structures of gymnemosides a and b were determined on the basis of chemical and physicochemical evidence as 21-O-tigloyl-22-O-acetylgymnemagenin 3-O-beta-D-glucopyranosiduronic acid and 16-O-acetyl-21-O-Tigloylgymnemagenin 3-O-beta-D-glucopyranosiduronic acid, respectively. In addition, an acetyl group linked to the 16- or 22-hydroxyl group in gymnemosides a and b was found to migrate easily to the primary 28-hydroxyl group, while the acyl migration from the 28-position was rarely observed.
CONCLUSIONS:
The inhibitory activity of each triterpene glycoside from gymnemic acid was examined to determine its impact on the increase of serum glucose level in oral glucose-loaded rats. Gymnemoside b and gymnemic acids III, V, and VII were found to exhibit a little inhibitory activity against glucose absorption, but the principal constituents, gymnemic acid I and gymnemasaponin V, lacked this activity.

21-O-Tigloylgymnemagenin Dilution Calculator

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Preparing Stock Solutions of 21-O-Tigloylgymnemagenin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.6983 mL 8.4917 mL 16.9834 mL 33.9668 mL 42.4585 mL
5 mM 0.3397 mL 1.6983 mL 3.3967 mL 6.7934 mL 8.4917 mL
10 mM 0.1698 mL 0.8492 mL 1.6983 mL 3.3967 mL 4.2459 mL
50 mM 0.034 mL 0.1698 mL 0.3397 mL 0.6793 mL 0.8492 mL
100 mM 0.017 mL 0.0849 mL 0.1698 mL 0.3397 mL 0.4246 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 21-O-Tigloylgymnemagenin

Medicinal foodstuffs. IX. The inhibitors of glucose absorption from the leaves of Gymnema sylvestre R. BR. (Asclepiadaceae): structures of gymnemosides a and b.[Pubmed:9353896]

Chem Pharm Bull (Tokyo). 1997 Oct;45(10):1671-6.

Although the glycosidic fraction from the dried leaves of Gymnema sylvestre R. BR., gymnemic acid, was reported to be effective for diabetes, it showed little inhibitory activity on the increase of serum glucose level in oral glucose-loaded rats. From the glycosidic fraction, six triterpene glycosides, gymnemosides a, b, c, d, e, and f, were isolated together with nine known triterpene glycosides. The structures of gymnemosides a and b were determined on the basis of chemical and physicochemical evidence as 21-O-tigloyl-22-O-acetylgymnemagenin 3-O-beta-D-glucopyranosiduronic acid and 16-O-acetyl-21-O-Tigloylgymnemagenin 3-O-beta-D-glucopyranosiduronic acid, respectively. In addition, an acetyl group linked to the 16- or 22-hydroxyl group in gymnemosides a and b was found to migrate easily to the primary 28-hydroxyl group, while the acyl migration from the 28-position was rarely observed. The inhibitory activity of each triterpene glycoside from gymnemic acid was examined to determine its impact on the increase of serum glucose level in oral glucose-loaded rats. Gymnemoside b and gymnemic acids III, V, and VII were found to exhibit a little inhibitory activity against glucose absorption, but the principal constituents, gymnemic acid I and gymnemasaponin V, lacked this activity.

Description

21-​O-​Tigloylgymnemagenin (Compound 7) is a acylated triterpenes isolated from Gymnema sylvestre.

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