Ganoderic acid D

CAS# 108340-60-9

Ganoderic acid D

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Chemical structure

Ganoderic acid D

3D structure

Chemical Properties of Ganoderic acid D

Cas No. 108340-60-9 SDF Download SDF
PubChem ID 102004379 Appearance White powder
Formula C30H42O7 M.Wt 514.66
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in methanol; insoluble in water
Chemical Name (6R)-6-[(7S,10S,13R,14R,17R)-7-hydroxy-4,4,10,13,14-pentamethyl-3,11,15-trioxo-1,2,5,6,7,12,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic acid
SMILES CC(CC(=O)CC(C)C(=O)O)C1CC(=O)C2(C1(CC(=O)C3=C2C(CC4C3(CCC(=O)C4(C)C)C)O)C)C
Standard InChIKey YTVGSCZIHGRVAV-FTRKVESOSA-N
Standard InChI InChI=1S/C30H42O7/c1-15(10-17(31)11-16(2)26(36)37)18-12-23(35)30(7)25-19(32)13-21-27(3,4)22(34)8-9-28(21,5)24(25)20(33)14-29(18,30)6/h15-16,18-19,21,32H,8-14H2,1-7H3,(H,36,37)/t15-,16?,18-,19+,21?,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 Ganoderic acid D

The fruit body of Ganoderma lucidum

Biological Activity of Ganoderic acid D

DescriptionGanoderic acid D treatment for 48h inhibits the proliferation of HeLa human cervical carcinoma cells with an IC(50) value of 17.3 +/- 0.3 microM.
In vitro

Proteomics characterization of the cytotoxicity mechanism of ganoderic acid D and computer-automated estimation of the possible drug target network.[Pubmed: 18166740]

Mol Cell Proteomics. 2008 May;7(5):949-61.

Triterpenes isolated from Ganoderma lucidum could inhibit the growth of numerous cancer cell lines and were thought to be the basis of the anticancer effects of G. lucidum. Ganoderic acid D (GAD) is one of the major components in Ganoderma triterpenes. GAD treatment for 48 h inhibited the proliferation of HeLa human cervical carcinoma cells with an IC(50) value of 17.3 +/- 0.3 microM. Flow cytometric analysis and DNA fragmentation analysis indicated that Ganoderic acid D induced G(2)/M cell cycle arrest and apoptosis.
METHODS AND RESULTS:
To identify the cellular targets of Ganoderic acid D, two-dimensional gel electrophoresis was performed, and proteins altered in expressional level after Ganoderic acid D exposure of cells were identified by MALDI-TOF MS/MS. The regulation of proteins was also confirmed by Western blotting. The cytotoxic effect of Ganoderic acid D was associated with regulated expression of 21 proteins. Furthermore these possible Ganoderic acid D target-related proteins were evaluated by an in silico drug target searching program, INVDOCK. The INVDOCK analysis results suggested that Ganoderic acid D could bind six isoforms of 14-3-3 protein family, annexin A5, and aminopeptidase B. The direct binding affinity of Ganoderic acid D toward 14-3-3 zeta was confirmed in vitro using surface plasmon resonance biosensor analysis. In addition, the intensive study of functional association among these 21 proteins revealed that 14 of them were closely related in the protein-protein interaction network. They had been found to either interact with each other directly or associate with each other via only one intermediate protein from previous protein-protein interaction experimental results. When the network was expanded to a further interaction outward, all 21 proteins could be included into one network.
CONCLUSIONS:
In this way, the possible network associated with Ganoderic acid D target-related proteins was constructed, and the possible contribution of these proteins to the cytotoxicity of Ganoderic acid D is discussed in this report.

In vivo

Identification of metabolites of ganoderic acid D by ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry.[Pubmed: 22942320]

Drug Metab Dispos. 2012 Dec;40(12):2307-14.

Ganoderic acid D (GD) is the major active triterpenoid in Ganoderma lucidum, a medicinal fungus used daily. However, the metabolic fate of Ganoderic acid D remains unknown. To know whether Ganoderic acid D is extensively metabolized, we first investigated the metabolism of Ganoderic acid D in vitro and in vivo.
METHODS AND RESULTS:
The metabolic profiles of the bile samples obtained from rats in vivo were almost the same as those obtained in vitro. Using ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry, a total of 25 metabolites were identified from the bile sample. Few metabolites were found in the urine samples. These results indicated that biliary rather than renal clearance was the major route of excretion. The major metabolites were identified by comparison with the standard reference compounds. Metabolites at low concentrations were identified by interpreting the mass spectra. Both phase I and phase II metabolites were observed. The metabolic transformation included reduction, monohydroxylation, dihydroxylation, trihydroxylation, oxidation, desaturation, sulfation, and glucuronidation. The main metabolic soft spots in the chemical structure of Ganoderic acid D were the 3-carbonyl group, angular methyl groups, the 7-hydroxy group, and the 26-carboxylic acid moiety.
CONCLUSIONS:
Overall, this study gives us an insight into the metabolism of Ganoderic acid D, an active oxygenated tetracyclic triterpenoid.

Ganoderic acid D Dilution Calculator

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Preparing Stock Solutions of Ganoderic acid D

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.943 mL 9.7152 mL 19.4303 mL 38.8606 mL 48.5758 mL
5 mM 0.3886 mL 1.943 mL 3.8861 mL 7.7721 mL 9.7152 mL
10 mM 0.1943 mL 0.9715 mL 1.943 mL 3.8861 mL 4.8576 mL
50 mM 0.0389 mL 0.1943 mL 0.3886 mL 0.7772 mL 0.9715 mL
100 mM 0.0194 mL 0.0972 mL 0.1943 mL 0.3886 mL 0.4858 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 Ganoderic acid D

Identification of metabolites of ganoderic acid D by ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry.[Pubmed:22942320]

Drug Metab Dispos. 2012 Dec;40(12):2307-14.

Ganoderic acid D (GD) is the major active triterpenoid in Ganoderma lucidum, a medicinal fungus used daily. However, the metabolic fate of GD remains unknown. To know whether GD is extensively metabolized, we first investigated the metabolism of GD in vitro and in vivo. The metabolic profiles of the bile samples obtained from rats in vivo were almost the same as those obtained in vitro. Using ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry, a total of 25 metabolites were identified from the bile sample. Few metabolites were found in the urine samples. These results indicated that biliary rather than renal clearance was the major route of excretion. The major metabolites were identified by comparison with the standard reference compounds. Metabolites at low concentrations were identified by interpreting the mass spectra. Both phase I and phase II metabolites were observed. The metabolic transformation included reduction, monohydroxylation, dihydroxylation, trihydroxylation, oxidation, desaturation, sulfation, and glucuronidation. The main metabolic soft spots in the chemical structure of GD were the 3-carbonyl group, angular methyl groups, the 7-hydroxy group, and the 26-carboxylic acid moiety. Overall, this study gives us an insight into the metabolism of GD, an active oxygenated tetracyclic triterpenoid.

Proteomics characterization of the cytotoxicity mechanism of ganoderic acid D and computer-automated estimation of the possible drug target network.[Pubmed:18166740]

Mol Cell Proteomics. 2008 May;7(5):949-61.

Triterpenes isolated from Ganoderma lucidum could inhibit the growth of numerous cancer cell lines and were thought to be the basis of the anticancer effects of G. lucidum. Ganoderic acid D (GAD) is one of the major components in Ganoderma triterpenes. GAD treatment for 48 h inhibited the proliferation of HeLa human cervical carcinoma cells with an IC(50) value of 17.3 +/- 0.3 microM. Flow cytometric analysis and DNA fragmentation analysis indicated that GAD induced G(2)/M cell cycle arrest and apoptosis. To identify the cellular targets of GAD, two-dimensional gel electrophoresis was performed, and proteins altered in expressional level after GAD exposure of cells were identified by MALDI-TOF MS/MS. The regulation of proteins was also confirmed by Western blotting. The cytotoxic effect of GAD was associated with regulated expression of 21 proteins. Furthermore these possible GAD target-related proteins were evaluated by an in silico drug target searching program, INVDOCK. The INVDOCK analysis results suggested that GAD could bind six isoforms of 14-3-3 protein family, annexin A5, and aminopeptidase B. The direct binding affinity of GAD toward 14-3-3 zeta was confirmed in vitro using surface plasmon resonance biosensor analysis. In addition, the intensive study of functional association among these 21 proteins revealed that 14 of them were closely related in the protein-protein interaction network. They had been found to either interact with each other directly or associate with each other via only one intermediate protein from previous protein-protein interaction experimental results. When the network was expanded to a further interaction outward, all 21 proteins could be included into one network. In this way, the possible network associated with GAD target-related proteins was constructed, and the possible contribution of these proteins to the cytotoxicity of GAD is discussed in this report.

Description

Ganoderic acid D, a highly oxygenated tetracyclic triterpenoid, is the major active component of Ganoderma lucidum. Ganoderic acid D upregulates the protein expression of SIRT3 and induces the deacetylated cyclophilin D (CypD) by SIRT3. Ganoderic acid D inhibits the energy reprogramming of colon cancer cells including glucose uptake, lactate production, pyruvate and acetyl-coenzyme production in colon cancer cells.

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