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Ganoderic acid DM (Ganoderic acid DM) 173075-45-1

Ganoderic acid DM (Ganoderic acid DM) 173075-45-1

CAS No.: 173075-45-1

Ganoderic acid DM is a natural triterpene extracted from Ganoderma lucidum and can induce DNA damage, G1 cell cycle arre
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Ganoderic acid DM is a natural triterpene extracted from Ganoderma lucidum and can induce DNA damage, G1 cell cycle arrest and apoptosis in human breast cancer cells. Ganoderic acid DM is also a specific inhibitor of osteoclastogenesis.

Physicochemical Properties


Molecular Formula C30H44O4
Molecular Weight 468.67
Exact Mass 468.323
CAS # 173075-45-1
PubChem CID 11784642
Appearance White to off-white solid powder
Density 1.1±0.1 g/cm3
Boiling Point 602.1±55.0 °C at 760 mmHg
Flash Point 332.0±28.0 °C
Vapour Pressure 0.0±3.7 mmHg at 25°C
Index of Refraction 1.547
LogP 6.9
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 4
Rotatable Bond Count 5
Heavy Atom Count 34
Complexity 984
Defined Atom Stereocenter Count 6
SMILES

C[C@H](CC/C=C(\C)/C(=O)O)[C@H]1CC[C@@]2([C@@]1(CCC3=C2C(=O)C[C@@H]4[C@@]3(CCC(=O)C4(C)C)C)C)C

InChi Key ZTKZZRIVAYGFSF-PIPDTRPPSA-N
InChi Code

InChI=1S/C30H44O4/c1-18(9-8-10-19(2)26(33)34)20-11-16-30(7)25-21(12-15-29(20,30)6)28(5)14-13-24(32)27(3,4)23(28)17-22(25)31/h10,18,20,23H,8-9,11-17H2,1-7H3,(H,33,34)/b19-10+/t18-,20-,23+,28-,29-,30+/m1/s1
Chemical Name

(E,6R)-2-methyl-6-[(5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3,7-dioxo-2,5,6,11,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]hept-2-enoic acid
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


ln Vitro In MCF-7 human breast cancer cells, ganoderic acid DM (GADM) significantly suppresses colony formation and cell proliferation more potently than it does in MDA-MB-231 breast cancer cells[1]. Nuclear factor of activated T cells c1 (NFATc1) and c-Fos expression are specifically suppressed by ganoderic acid DM. The expression of TRAP mRNA and cathepsin K was significantly decreased by ganoderic acid DM[2]. Non-small cell lung cancer cells undergo autophagic apoptosis when ganoderic acid DM inhibits PI3K/Akt/mTOR activity[3].
Cell Assay Cell Viability Assay[1]
Cell Types: MCF-7 and MDA-MB-231 cells.
Tested Concentrations: 0-100 μM.
Incubation Duration: 48 h.
Experimental Results: diminished the cell viability in breast cancer cells.

Cell Viability Assay[2]
Cell Types: RAW-D cells.
Tested Concentrations: 0-100 μg/mL.
Incubation Duration: 0-100 μg/mL.
Experimental Results: Clearly suppressed osteoclastogenesis from the RAW 264 cell D-clone.
References

[1]. Ganoderic acid DM, a natural triterpenoid, induces DNA damage, G1 cell cycle arrest and apoptosis in human breast cancer cells. Fitoterapia. 2012 Mar;83(2):408-14.

[2]. Regulation of osteoclastogenesis by ganoderic acid DM isolated from Ganoderma lucidum. Eur J Pharmacol. 2009 Jan 5;602(1):1-7.

[3]. Ganoderic acid DM induces autophagic apoptosis in non-small cell lung cancer cells by inhibiting the PI3K/Akt/mTOR activity. Chem Biol Interact. 2020 Jan 25;316:108932.

Additional Infomation Ganoderic acid DM is a triterpenoid.
(E,6R)-2-methyl-6-[(5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3,7-dioxo-2,5,6,11,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]hept-2-enoic acid has been reported in Ganoderma lucidum with data available.

Solubility Data


Solubility (In Vitro) DMSO : 50 mg/mL (106.68 mM)
Solubility (In Vivo) Solubility in Formulation 1: 1.25 mg/mL (2.67 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 1.25 mg/mL (2.67 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

Solubility in Formulation 3: ≥ 1.25 mg/mL (2.67 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1337 mL 10.6685 mL 21.3370 mL
5 mM 0.4267 mL 2.1337 mL 4.2674 mL
10 mM 0.2134 mL 1.0668 mL 2.1337 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.