Ganoderic acid H

CAS# 98665-19-1

Ganoderic acid H

2D Structure

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Ganoderic acid H: 5mg $322 In Stock
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Quality Control of Ganoderic acid H

3D structure

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Ganoderic acid H

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Chemical Properties of Ganoderic acid H

Cas No. 98665-19-1 SDF Download SDF
PubChem ID 471005 Appearance Powder
Formula C32H44O9 M.Wt 572.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2R,6S)-6-[(3S,5R,10S,12S,13R,14R,17R)-12-acetyloxy-3-hydroxy-4,4,10,13,14-pentamethyl-7,11,15-trioxo-1,2,3,5,6,12,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic acid
SMILES CC(CC(=O)CC(C)C(=O)O)C1CC(=O)C2(C1(C(C(=O)C3=C2C(=O)CC4C3(CCC(C4(C)C)O)C)OC(=O)C)C)C
Standard InChIKey YCXUCEXEMJPDRZ-QWPKPZHNSA-N
Standard InChI InChI=1S/C32H44O9/c1-15(11-18(34)12-16(2)28(39)40)19-13-23(37)32(8)24-20(35)14-21-29(4,5)22(36)9-10-30(21,6)25(24)26(38)27(31(19,32)7)41-17(3)33/h15-16,19,21-22,27,36H,9-14H2,1-8H3,(H,39,40)/t15-,16+,19+,21-,22-,27+,30-,31-,32-/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 Ganoderic acid H

The fruit body of Ganoderma lucidum

Biological Activity of Ganoderic acid H

DescriptionGanoderic acid H is a potent antitumour agent, it mediates its biological effects through the inhibition of transcription factors AP-1 and NF-kappaB, resulting in the down-regulation of expression of Cdk4.
TargetsNF-kB | AP-1 | CDK
In vitro

Ganoderic acids suppress growth and invasive behavior of breast cancer cells by modulating AP-1 and NF-kappaB signaling.[Pubmed: 18425349]

Int J Mol Med. 2008 May;21(5):577-84.

Structurally related lanostane-type triterpenes, ganoderic acid A, F and H (GA-A, GA-F, Ganoderic acid H), were identified in an oriental medicinal mushroom Ganoderma lucidum.
METHODS AND RESULTS:
In the present study we evaluated the effect of GA-A, Ganoderic acid H and GA-F on highly invasive human breast cancer cells. We showed that GA-A and Ganoderic acid H suppressed growth (cell proliferation and colony formation) and invasive behavior (adhesion, migration and invasion) of MDA-MB-231 cells. Our results suggest that GA-A and Ganoderic acid H mediate their biological effects through the inhibition of transcription factors AP-1 and NF-kappaB, resulting in the down-regulation of expression of Cdk4 and the suppression of secretion of uPA, respectively. Furthermore, the activity of ganoderic acids is linked to the hydroxylation in the position 7 and 15 (GA-A) and 3 (Ganoderic acid H) in their triterpene lanostane structure.
CONCLUSIONS:
In conclusion, hydroxylated triterpenes from G. lucidum could be promising natural agents for the therapy of invasive breast cancers.

Protocol of Ganoderic acid H

Structure Identification
Nat Prod Res. 2014;28(24):2264-72.

Extraction optimisation and isolation of triterpenoids from Ganoderma lucidum and their effect on human carcinoma cell growth.[Pubmed: 25032738]

The response surface methodology was used to optimise the extraction conditions of Ganoderma lucidum based on a Box-Behnken design.
METHODS AND RESULTS:
A quadratic model sufficiently simulated the response of Ganoderic acid H with a determination coefficient (R(2)) of 0.98. The optimal condition for extracting triterpenoids was determined to be 100.00% ethanol at 60.22°C for 6.00 h, under which the yield of the reference triterpenoid Ganoderic acid H increased from 0.88 to 2.09 mg/g powder. Following extraction, triterpenoid-enriched fraction was further isolated into 23 fractions, and 7 fractions were identified as ganoderic acids A, B, D, G, H and I and ganoderenic acid D. Of the seven triterpenoids, ganoderenic acid D was most cytotoxic with IC50 values of 0.14 ± 0.01, 0.18 ± 0.02 and 0.26 ± 0.03 mg/mL in Hep G2, Hela and Caco-2 cells, respectively. While ganoderic acids A, G and H were relatively non-cytotoxic.
CONCLUSIONS:
The variation of inhibitory effects for these triterpenoids was likely related to their chemical structures.

Ganoderic acid H Dilution Calculator

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Ganoderic acid H Molarity Calculator

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Preparing Stock Solutions of Ganoderic acid H

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.7461 mL 8.7306 mL 17.4611 mL 34.9223 mL 43.6529 mL
5 mM 0.3492 mL 1.7461 mL 3.4922 mL 6.9845 mL 8.7306 mL
10 mM 0.1746 mL 0.8731 mL 1.7461 mL 3.4922 mL 4.3653 mL
50 mM 0.0349 mL 0.1746 mL 0.3492 mL 0.6984 mL 0.8731 mL
100 mM 0.0175 mL 0.0873 mL 0.1746 mL 0.3492 mL 0.4365 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 H

Extraction optimisation and isolation of triterpenoids from Ganoderma lucidum and their effect on human carcinoma cell growth.[Pubmed:25032738]

Nat Prod Res. 2014;28(24):2264-72.

The response surface methodology was used to optimise the extraction conditions of Ganoderma lucidum based on a Box-Behnken design. A quadratic model sufficiently simulated the response of Ganoderic acid H with a determination coefficient (R(2)) of 0.98. The optimal condition for extracting triterpenoids was determined to be 100.00% ethanol at 60.22 degrees C for 6.00 h, under which the yield of the reference triterpenoid Ganoderic acid H increased from 0.88 to 2.09 mg/g powder. Following extraction, triterpenoid-enriched fraction was further isolated into 23 fractions, and 7 fractions were identified as ganoderic acids A, B, D, G, H and I and ganoderenic acid D. Of the seven triterpenoids, ganoderenic acid D was most cytotoxic with IC50 values of 0.14 +/- 0.01, 0.18 +/- 0.02 and 0.26 +/- 0.03 mg/mL in Hep G2, Hela and Caco-2 cells, respectively. While ganoderic acids A, G and H were relatively non-cytotoxic. The variation of inhibitory effects for these triterpenoids was likely related to their chemical structures.

Ganoderic acids suppress growth and invasive behavior of breast cancer cells by modulating AP-1 and NF-kappaB signaling.[Pubmed:18425349]

Int J Mol Med. 2008 May;21(5):577-84.

Structurally related lanostane-type triterpenes, ganoderic acid A, F and H (GA-A, GA-F, GA-H), were identified in an oriental medicinal mushroom Ganoderma lucidum. In the present study we evaluated the effect of GA-A, GA-H and GA-F on highly invasive human breast cancer cells. We showed that GA-A and GA-H suppressed growth (cell proliferation and colony formation) and invasive behavior (adhesion, migration and invasion) of MDA-MB-231 cells. Our results suggest that GA-A and GA-H mediate their biological effects through the inhibition of transcription factors AP-1 and NF-kappaB, resulting in the down-regulation of expression of Cdk4 and the suppression of secretion of uPA, respectively. Furthermore, the activity of ganoderic acids is linked to the hydroxylation in the position 7 and 15 (GA-A) and 3 (GA-H) in their triterpene lanostane structure. In conclusion, hydroxylated triterpenes from G. lucidum could be promising natural agents for the therapy of invasive breast cancers.

Description

Ganoderic acid H is a lanostane-type triterpene isolated from Ganoderma lucidum. Ganoderic acid H suppresses growth and invasive behavior of breast cancer cells through the inhibition of transcription factors AP-1 and NF-kappaB signaling.

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