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Dehydrotrametenolic acid

CAS# 29220-16-4

Dehydrotrametenolic acid

2D Structure

Catalog No. BCN2718----Order now to get a substantial discount!

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3D structure

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Dehydrotrametenolic acid

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Chemical Properties of Dehydrotrametenolic acid

Cas No. 29220-16-4 SDF Download SDF
PubChem ID 15391340 Appearance Powder
Formula C30H46O3 M.Wt 454.69
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms 3-DEHYDROTRAMETENOLIC ACID
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2R)-2-[(3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
SMILES CC(=CCCC(C1CCC2(C1(CC=C3C2=CCC4C3(CCC(C4(C)C)O)C)C)C)C(=O)O)C
Standard InChIKey QFPLAAZRZNKRRY-GIICLEHTSA-N
Standard InChI InChI=1S/C30H46O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,11,14,20-21,24-25,31H,8,10,12-13,15-18H2,1-7H3,(H,32,33)/t20-,21-,24+,25+,28-,29-,30+/m1/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 Dehydrotrametenolic acid

The roots of Wolfiporia cocos (Schw.) Ryv.

Biological Activity of Dehydrotrametenolic acid

DescriptionDehydrotrametenolic acid is a promising candidate for a new type of insulin-sensitizing drug; it can be a potential anticancer agent against H-ras transformed tumor.
TargetsPARP | Caspase | Akt | ERK | PPAR
In vitro

Dehydrotrametenolic acid selectively inhibits the growth of H-ras transformed rat2 cells and induces apoptosis through caspase-3 pathway.[Pubmed: 16112686]

Life Sci. 2006 Jan 2;78(6):607-13.

The screening of natural products that preferentially inhibit growth of H-ras transformed rat2 cells vs. rat2 cells was performed to identify H-ras specific growth inhibitor.
METHODS AND RESULTS:
A lanostane-type triterpene acid, Dehydrotrametenolic acid (3beta-hydroxylanosta-7,9(11),24-trien-21-oic acid), was isolated from the sclerotium of Poria cocos (Polyporaceae). Dehydrotrametenolic acid selectively inhibited the growth of H-ras transformed cells with a GI(50) value of 40 microM. FACS analysis indicated that the compound exerted its anti-proliferation effects through cell cycle arrest at G2/M phase and accumulation of sub-G1 population. Dehydrotrametenolic acid-induced apoptosis was further confirmed with chromosomal DNA fragmentation, caspase-3 activation, and degradation of PARP and Lamin A/C degradation. The compound also regulated the expression of H-ras, Akt and Erk, which are the downstream proteins of H-ras signaling pathways.
CONCLUSIONS:
The results suggest that Dehydrotrametenolic acid can be a potential anticancer agent against H-ras transformed tumor.

In vivo

Dehydrotrametenolic acid induces preadipocyte differentiation and sensitizes animal models of noninsulin-dependent diabetes mellitus to insulin.[Pubmed: 11824563]

Biol Pharm Bull. 2002 Jan;25(1):81-6.

We recently discovered that the triterpene acid compound Dehydrotrametenolic acid promotes adipocyte differentiation in vitro and acts as an insulin sensitizer in vivo. This natural product has been isolated from dried sclerotia of Poria cocos WOLF (Polyporaceae), a well-known traditional Chinese medicinal plant.
METHODS AND RESULTS:
We examined the effects of Dehydrotrametenolic acid on plasma glucose concentration in obese hyperglycemic db/db mice. Dehydrotrametenolic acid can reduce hyperglycemia in mouse models of noninsulin-dependent diabetes mellitus (NIDDM) and act as an insulin sensitizer as indicated by the results of the glucose tolerance test. These terpenoids and thiazolidine type of antidiabetic agents such as Ciglitazone, although structurally unrelated, share many biological activities: both induce adipose conversion, activate peroxisome proliferator-activated receptor gamma (PPAR gamma) in vitro, and reduce hyperglycemia in animal models of NIDDM. Dehydrotrametenolic acid is a promising candidate for a new type of insulin-sensitizing drug.
CONCLUSIONS:
This finding is very important for the development of insulin sensitizers that are not of the thiazolidine type.

Dehydrotrametenolic acid Dilution Calculator

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Preparing Stock Solutions of Dehydrotrametenolic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1993 mL 10.9965 mL 21.993 mL 43.986 mL 54.9825 mL
5 mM 0.4399 mL 2.1993 mL 4.3986 mL 8.7972 mL 10.9965 mL
10 mM 0.2199 mL 1.0997 mL 2.1993 mL 4.3986 mL 5.4983 mL
50 mM 0.044 mL 0.2199 mL 0.4399 mL 0.8797 mL 1.0997 mL
100 mM 0.022 mL 0.11 mL 0.2199 mL 0.4399 mL 0.5498 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 Dehydrotrametenolic acid

Dehydrotrametenolic acid induces preadipocyte differentiation and sensitizes animal models of noninsulin-dependent diabetes mellitus to insulin.[Pubmed:11824563]

Biol Pharm Bull. 2002 Jan;25(1):81-6.

We recently discovered that the triterpene acid compound Dehydrotrametenolic acid promotes adipocyte differentiation in vitro and acts as an insulin sensitizer in vivo. This natural product has been isolated from dried sclerotia of Poria cocos WOLF (Polyporaceae), a well-known traditional Chinese medicinal plant. We examined the effects of Dehydrotrametenolic acid on plasma glucose concentration in obese hyperglycemic db/db mice. Dehydrotrametenolic acid can reduce hyperglycemia in mouse models of noninsulin-dependent diabetes mellitus (NIDDM) and act as an insulin sensitizer as indicated by the results of the glucose tolerance test. These terpenoids and thiazolidine type of antidiabetic agents such as Ciglitazone, although structurally unrelated, share many biological activities: both induce adipose conversion, activate peroxisome proliferator-activated receptor gamma (PPAR gamma) in vitro, and reduce hyperglycemia in animal models of NIDDM. Dehydrotrametenolic acid is a promising candidate for a new type of insulin-sensitizing drug. This finding is very important for the development of insulin sensitizers that are not of the thiazolidine type.

Dehydrotrametenolic acid selectively inhibits the growth of H-ras transformed rat2 cells and induces apoptosis through caspase-3 pathway.[Pubmed:16112686]

Life Sci. 2006 Jan 2;78(6):607-13.

The screening of natural products that preferentially inhibit growth of H-ras transformed rat2 cells vs. rat2 cells was performed to identify H-ras specific growth inhibitor. A lanostane-type triterpene acid, Dehydrotrametenolic acid (3beta-hydroxylanosta-7,9(11),24-trien-21-oic acid), was isolated from the sclerotium of Poria cocos (Polyporaceae). Dehydrotrametenolic acid selectively inhibited the growth of H-ras transformed cells with a GI(50) value of 40 microM. FACS analysis indicated that the compound exerted its anti-proliferation effects through cell cycle arrest at G2/M phase and accumulation of sub-G1 population. Dehydrotrametenolic acid-induced apoptosis was further confirmed with chromosomal DNA fragmentation, caspase-3 activation, and degradation of PARP and Lamin A/C degradation. The compound also regulated the expression of H-ras, Akt and Erk, which are the downstream proteins of H-ras signaling pathways. The results suggest that Dehydrotrametenolic acid can be a potential anticancer agent against H-ras transformed tumor.

Description

3-​Dehydrotrametenolic acid, isolated from the sclerotium of Poria cocos, is a lactate dehydrogenase (LDH) inhibitor. 3-​Dehydrotrametenolic acid promotes adipocyte differentiation in vitro and acts as an insulin sensitizer in vivo. 3-​Dehydrotrametenolic acid induces apoptosis and has anticancer activity.

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