Ganoderic Acid DM | CAS#173075-45-1 | Diverse triterpenoid

MedKoo Cat#: 465314 | Name: Ganoderic Acid DM

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ganoderic acid DM is a triterpenoid that has been found in G. lucidum and has diverse biological activities. It inhibits 5α-reductase and HMG-CoA reductase (IC50s = 10.6 and 9.5 µM, respectively) and binds to the ligand-binding domain of the androgen receptor in a fluorescence polarization assay. Ganoderic acid suppresses osteoclastogenesis of RAW 264.7 cells when used at a concentration of 12.5 µM and is cytotoxic to K562 leukemia and PC3 prostate cancer cells (IC50s = 18.8 and 81.6 µM, respectively). It reduces ear edema induced by phorbol 12-myristate 13-acetate (TPA) in mice (ID50 = 0.08 mg/ear).

Chemical Structure

Ganoderic Acid DM

CAS#173075-45-1

Theoretical Analysis

MedKoo Cat#: 465314

Name: Ganoderic Acid DM

CAS#: 173075-45-1

Chemical Formula: C30H44O4

Exact Mass: 468.3240

Molecular Weight: 468.68

Elemental Analysis: C, 76.88; H, 9.46; O, 13.65

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350.00	2 Weeks
5mg	USD 850.00	2 Weeks

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Related CAS #

No Data

Synonym

Ganoderic Acid DM; (+)-Ganoderic acid DM;

IUPAC/Chemical Name

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

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

SMILES Code

C[C@]12C3=C([C@]4(C)[C@@]([H])(CC3=O)C(C(CC4)=O)(C)C)CC[C@]1(C)[C@]([H])(CC2)[C@H](C)CC/C=C(C(O)=O)\C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 468.68 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Xia J, Dai L, Wang L, Zhu J. 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. doi: 10.1016/j.cbi.2019.108932. Epub 2019 Dec 23. PMID: 31874162. 2: Das A, Alshareef M, Henderson F Jr, Martinez Santos JL, Vandergrift WA 3rd, Lindhorst SM, Varma AK, Infinger L, Patel SJ, Cachia D. Ganoderic acid A/DM- induced NDRG2 over-expression suppresses high-grade meningioma growth. Clin Transl Oncol. 2020 Jul;22(7):1138-1145. doi: 10.1007/s12094-019-02240-6. Epub 2019 Nov 15. PMID: 31732915. 3: Liang C, Tian D, Liu Y, Li H, Zhu J, Li M, Xin M, Xia J. Review of the molecular mechanisms of Ganoderma lucidum triterpenoids: Ganoderic acids A, C2, D, F, DM, X and Y. Eur J Med Chem. 2019 Jul 15;174:130-141. doi: 10.1016/j.ejmech.2019.04.039. Epub 2019 Apr 20. PMID: 31035236. 4: Johnson BM, Radwan FFY, Hossain A, Doonan BP, Hathaway-Schrader JD, God JM, Voelkel-Johnson CV, Banik NL, Reddy SV, Haque A. Endoplasmic reticulum stress, autophagic and apoptotic cell death, and immune activation by a natural triterpenoid in human prostate cancer cells. J Cell Biochem. 2019 Apr;120(4):6264-6276. doi: 10.1002/jcb.27913. Epub 2018 Oct 30. PMID: 30378157; PMCID: PMC6561659. 5: Yang C, Li W, Li C, Zhou Z, Xiao Y, Yan X. Metabolism of ganoderic acids by a Ganoderma lucidum cytochrome P450 and the 3-keto sterol reductase ERG27 from yeast. Phytochemistry. 2018 Nov;155:83-92. doi: 10.1016/j.phytochem.2018.07.009. Epub 2018 Aug 2. PMID: 30077898. 6: Bryant JM, Bouchard M, Haque A. Anticancer Activity of Ganoderic Acid DM: Current Status and Future Perspective. J Clin Cell Immunol. 2017;8(6):535. doi: 10.4172/2155-9899.1000535. Epub 2017 Dec 12. PMID: 29399381; PMCID: PMC5795599. 7: Yang Z, Wu F, Yuan X, Zhang L, Zhang S. Novel binding patterns between ganoderic acids and neuraminidase: Insights from docking, molecular dynamics and MM/PBSA studies. J Mol Graph Model. 2016 Apr;65:27-34. doi: 10.1016/j.jmgm.2016.02.006. Epub 2016 Feb 15. PMID: 26905206. 8: Ruan W, Wei Y, Popovich DG. Distinct Responses of Cytotoxic Ganoderma lucidum Triterpenoids in Human Carcinoma Cells. Phytother Res. 2015 Nov;29(11):1744-52. doi: 10.1002/ptr.5426. Epub 2015 Aug 21. PMID: 26292672. 9: Das A, Miller R, Lee P, Holden CA, Lindhorst SM, Jaboin J, Vandergrift WA 3rd, Banik NL, Giglio P, Varma AK, Raizer JJ, Patel SJ. A novel component from citrus, ginger, and mushroom family exhibits antitumor activity on human meningioma cells through suppressing the Wnt/β-catenin signaling pathway. Tumour Biol. 2015 Sep;36(9):7027-34. doi: 10.1007/s13277-015-3388-0. Epub 2015 Apr 12. PMID: 25864108. 10: Liu J, Shimizu K, Tanaka A, Shinobu W, Ohnuki K, Nakamura T, Kondo R. Target proteins of ganoderic acid DM provides clues to various pharmacological mechanisms. Sci Rep. 2012;2:905. doi: 10.1038/srep00905. Epub 2012 Nov 30. PMID: 23205267; PMCID: PMC3510465. 11: Hossain A, Radwan FF, Doonan BP, God JM, Zhang L, Bell PD, Haque A. A possible cross-talk between autophagy and apoptosis in generating an immune response in melanoma. Apoptosis. 2012 Oct;17(10):1066-78. doi: 10.1007/s10495-012-0745-y. PMID: 22847295; PMCID: PMC3747633. 12: Wu GS, Lu JJ, Guo JJ, Li YB, Tan W, Dang YY, Zhong ZF, Xu ZT, Chen XP, Wang YT. 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. doi: 10.1016/j.fitote.2011.12.004. Epub 2011 Dec 9. PMID: 22178684. 13: Chakrabortee S, Liu Y, Zhang L, Matthews HR, Zhang H, Pan N, Cheng CR, Guan SH, Guo DA, Huang Z, Zheng Y, Tunnacliffe A. Macromolecular and small-molecule modulation of intracellular Aβ42 aggregation and associated toxicity. Biochem J. 2012 Mar 15;442(3):507-15. doi: 10.1042/BJ20111661. PMID: 22150318. 14: Johnson BM, Doonan BP, Radwan FF, Haque A. Ganoderic Acid DM: An Alternative Agent for the Treatment of Advanced Prostate Cancer. Open Prost Cancer J. 2010 Jan 1;3:78-85. doi: 10.2174/1876822901003010078. PMID: 24790681; PMCID: PMC4002166. 15: Liu J, Shiono J, Shimizu K, Kukita A, Kukita T, Kondo R. Ganoderic acid DM: anti-androgenic osteoclastogenesis inhibitor. Bioorg Med Chem Lett. 2009 Apr 15;19(8):2154-7. doi: 10.1016/j.bmcl.2009.02.119. Epub 2009 Mar 4. PMID: 19289282. 16: Miyamoto I, Liu J, Shimizu K, Sato M, Kukita A, Kukita T, Kondo R. Regulation of osteoclastogenesis by ganoderic acid DM isolated from Ganoderma lucidum. Eur J Pharmacol. 2009 Jan 5;602(1):1-7. doi: 10.1016/j.ejphar.2008.11.005. Epub 2008 Nov 9. PMID: 19026632. 17: Zhao J, Zhang XQ, Li SP, Yang FQ, Wang YT, Ye WC. Quality evaluation of Ganoderma through simultaneous determination of nine triterpenes and sterols using pressurized liquid extraction and high performance liquid chromatography. J Sep Sci. 2006 Nov;29(17):2609-15. doi: 10.1002/jssc.200600178. PMID: 17313101. 18: Liu J, Kurashiki K, Shimizu K, Kondo R. 5alpha-reductase inhibitory effect of triterpenoids isolated from Ganoderma lucidum. Biol Pharm Bull. 2006 Feb;29(2):392-5. doi: 10.1248/bpb.29.392. PMID: 16462054. 19: Wang FS, Cai H, Yang JS, Zhang YM, Hou CY, Liu JQ, Zhao MJ. [Studies on the ganoderic acid, a new constituents from the fruiting body of Ganoderma lucidum (Fr.) Karst]. Yao Xue Xue Bao. 1997 Jun;32(6):447-50. Chinese. PMID: 11596326.