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MedKoo Cat#: 462790 | Name: Ergosterol Peroxide
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Description:

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

Ergosterol peroxide is an oxidized sterol and derivative of ergosterol that has been found in S. aspratus and has diverse biological activities. It is active against the P. falciparum chloroquine-sensitive strain FCA 20/GHA with an IC50 value of 8.2 µM. Ergosterol peroxide induces apoptosis in LNCaP and DU145 prostate cancer cells. It inhibits growth of SNU-1 gastric, SNU-354 hepatoma, and SNU-C4 colorectal cancer cells. Ergosterol peroxide inhibits LPS-induced NF-kB DNA-binding activity and production of TNF-α in RAW 264.7 cells.4 Topical application of ergosterol peroxide reduces ear edema in a mouse model of inflammation induced by phorbol 12-myristate 13-acetate with an ID50 value of 0.2 mg/ear.

Chemical Structure

Ergosterol Peroxide
Ergosterol Peroxide
CAS#2061-64-5

Theoretical Analysis

MedKoo Cat#: 462790

Name: Ergosterol Peroxide

CAS#: 2061-64-5

Chemical Formula: C28H44O3

Exact Mass: 428.3290

Molecular Weight: 428.66

Elemental Analysis: C, 78.46; H, 10.35; O, 11.20

Price and Availability

Size Price Availability Quantity
1mg USD 385.00 2 Weeks
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Synonym
Ergosterol Peroxide; Ergosterol Endoperoxide; 5a,8a-Peroxyergosterol; NSC31324; NSC 31324; NSC-31324;
IUPAC/Chemical Name
(3S,5S,8S,9R,10R,13R,14R,17R)-17-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-10,13-dimethyl-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-5,8-epidioxycyclopenta[a]phenanthren-3-ol
InChi Key
VXOZCESVZIRHCJ-KGHQQZOUSA-N
InChi Code
InChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,24+,25+,26+,27+,28-/m0/s1
SMILES Code
CC([C@H](/C=C/[C@H]([C@]1(CC[C@]2([C@@]34OO[C@@]5(C[C@H](CC[C@@]5([C@]4(CC[C@@]21C)[H])C)O)C=C3)[H])[H])C)C)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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Ergosterol peroxide has anti-tumour, proapoptotic, anti-inflammatory, anti-mycobacterial, and anti-proliferative activities.
In vitro activity:
Ergosterol peroxide showed preferred inhibition of MCF-7 (ER +ve) cell lines relative to MDA-MB-231 (ER -ve) cell lines with an IC50 of 1.18 μM and 12.82 μM respectively. These data suggest that ergosterol peroxide targets estrogen receptors. Reference: Int J Med Mushrooms. 2020;22(4):389-396. https://pubmed.ncbi.nlm.nih.gov/32558503/
In vivo activity:
Furthermore, EPO (ergosterol peroxide) significant inhibited both the migration and invasion of 4T1 cells in vitro, and pre-treatment of 4T1 cells with EPO significantly inhibited the formation of experimental lung metastases in vivo. Reference: J Nat Med. 2021 Apr 27. https://pubmed.ncbi.nlm.nih.gov/33905080/

Preparing Stock Solutions

The following data is based on the product molecular weight 428.66 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. El-Sherif NF, Ahmed SA, Ibrahim AK, Habib ES, El-Fallal AA, El-Sayed AK, Wahba AE. Ergosterol Peroxide from the Egyptian Red Lingzhi or Reishi Mushroom, Ganoderma resinaceum (Agaricomycetes), Showed Preferred Inhibition of MCF-7 over MDA-MB-231 Breast Cancer Cell Lines. Int J Med Mushrooms. 2020;22(4):389-396. doi: 10.1615/IntJMedMushrooms.2020034223. PMID: 32558503. 2. Tan W, Pan M, Liu H, Tian H, Ye Q, Liu H. Ergosterol peroxide inhibits ovarian cancer cell growth through multiple pathways. Onco Targets Ther. 2017 Jul 13;10:3467-3474. doi: 10.2147/OTT.S139009. PMID: 28761355; PMCID: PMC5518915. 3. Shin MK, Sasaki F, Ki DW, Win NN, Morita H, Hayakawa Y. Anti-metastatic effects of ergosterol peroxide from the entomopathogenic fungus Ophiocordyceps gracilioides on 4T1 breast cancer cells. J Nat Med. 2021 Apr 27. doi: 10.1007/s11418-021-01520-2. Epub ahead of print. PMID: 33905080. 4. Yang Y , Luo X , Yasheng M , Zhao J , Li J , Li J . Ergosterol peroxide from Pleurotus ferulae inhibits gastrointestinal tumor cell growth through induction of apoptosis via reactive oxygen species and endoplasmic reticulum stress. Food Funct. 2020 May 1;11(5):4171-4184. doi: 10.1039/c9fo02454a. Epub 2020 Apr 30. PMID: 32352095.
In vitro protocol:
1. El-Sherif NF, Ahmed SA, Ibrahim AK, Habib ES, El-Fallal AA, El-Sayed AK, Wahba AE. Ergosterol Peroxide from the Egyptian Red Lingzhi or Reishi Mushroom, Ganoderma resinaceum (Agaricomycetes), Showed Preferred Inhibition of MCF-7 over MDA-MB-231 Breast Cancer Cell Lines. Int J Med Mushrooms. 2020;22(4):389-396. doi: 10.1615/IntJMedMushrooms.2020034223. PMID: 32558503. 2. Tan W, Pan M, Liu H, Tian H, Ye Q, Liu H. Ergosterol peroxide inhibits ovarian cancer cell growth through multiple pathways. Onco Targets Ther. 2017 Jul 13;10:3467-3474. doi: 10.2147/OTT.S139009. PMID: 28761355; PMCID: PMC5518915.
In vivo protocol:
1. Shin MK, Sasaki F, Ki DW, Win NN, Morita H, Hayakawa Y. Anti-metastatic effects of ergosterol peroxide from the entomopathogenic fungus Ophiocordyceps gracilioides on 4T1 breast cancer cells. J Nat Med. 2021 Apr 27. doi: 10.1007/s11418-021-01520-2. Epub ahead of print. PMID: 33905080. 2. Yang Y , Luo X , Yasheng M , Zhao J , Li J , Li J . Ergosterol peroxide from Pleurotus ferulae inhibits gastrointestinal tumor cell growth through induction of apoptosis via reactive oxygen species and endoplasmic reticulum stress. Food Funct. 2020 May 1;11(5):4171-4184. doi: 10.1039/c9fo02454a. Epub 2020 Apr 30. PMID: 32352095.
1: Zhou B, Liang X, Feng Q, Li J, Pan X, Xie P, Jiang Z, Yang Z. Ergosterol peroxide suppresses influenza A virus-induced pro-inflammatory response and apoptosis by blocking RIG-I signaling. Eur J Pharmacol. 2019 Oct 5;860:172543. doi: 10.1016/j.ejphar.2019.172543. Epub 2019 Jul 16. PMID: 31323223. 2: Merdivan S, Lindequist U. Ergosterol Peroxide: A Mushroom-Derived Compound with Promising Biological Activities-A Review. Int J Med Mushrooms. 2017;19(2):93-105. doi: 10.1615/IntJMedMushrooms.v19.i2.10. PMID: 28436318. 3: Meza-Menchaca T, Ramos-Ligonio A, López-Monteon A, Vidal Limón A, Kaluzhskiy LA, V Shkel T, V Strushkevich N, Jiménez-García LF, Agredano Moreno LT, Gallegos-García V, Suárez-Medellín J, Trigos Á. Insights into Ergosterol Peroxide's Trypanocidal Activity. Biomolecules. 2019 Sep 12;9(9):484. doi: 10.3390/biom9090484. PMID: 31547423; PMCID: PMC6770379. 4: Ling T, Lang WH, Martinez-Montemayor MM, Rivas F. Development of ergosterol peroxide probes for cellular localisation studies. Org Biomol Chem. 2019 May 29;17(21):5223-5229. doi: 10.1039/c9ob00145j. PMID: 31025693; PMCID: PMC6541511. 5: Bu M, Li H, Wang H, Wang J, Lin Y, Ma Y. Synthesis of Ergosterol Peroxide Conjugates as Mitochondria Targeting Probes for Enhanced Anticancer Activity. Molecules. 2019 Sep 11;24(18):3307. doi: 10.3390/molecules24183307. PMID: 31514398; PMCID: PMC6766909. 6: Li X, Wu Q, Bu M, Hu L, Du WW, Jiao C, Pan H, Sdiri M, Wu N, Xie Y, Yang BB. Ergosterol peroxide activates Foxo3-mediated cell death signaling by inhibiting AKT and c-Myc in human hepatocellular carcinoma cells. Oncotarget. 2016 Jun 7;7(23):33948-59. doi: 10.18632/oncotarget.8608. PMID: 27058618; PMCID: PMC5085130. 7: Meza-Menchaca T, Suárez-Medellín J, Del Ángel-Piña C, Trigos Á. The Amoebicidal Effect of Ergosterol Peroxide Isolated from Pleurotus ostreatus. Phytother Res. 2015 Dec;29(12):1982-6. doi: 10.1002/ptr.5474. Epub 2015 Sep 22. PMID: 26392373. 8: He L, Shi W, Liu X, Zhao X, Zhang Z. Anticancer Action and Mechanism of Ergosterol Peroxide from Paecilomyces cicadae Fermentation Broth. Int J Mol Sci. 2018 Dec 7;19(12):3935. doi: 10.3390/ijms19123935. PMID: 30544579; PMCID: PMC6321734. 9: Kang JH, Jang JE, Mishra SK, Lee HJ, Nho CW, Shin D, Jin M, Kim MK, Choi C, Oh SH. Ergosterol peroxide from Chaga mushroom (Inonotus obliquus) exhibits anti-cancer activity by down-regulation of the β-catenin pathway in colorectal cancer. J Ethnopharmacol. 2015 Sep 15;173:303-12. doi: 10.1016/j.jep.2015.07.030. Epub 2015 Jul 22. PMID: 26210065. 10: Nowak R, Drozd M, Mendyk E, Lemieszek M, Krakowiak O, Kisiel W, Rzeski W, Szewczyk K. A New Method for the Isolation of Ergosterol and Peroxyergosterol as Active Compounds of Hygrophoropsis aurantiaca and in Vitro Antiproliferative Activity of Isolated Ergosterol Peroxide. Molecules. 2016 Jul 21;21(7):946. doi: 10.3390/molecules21070946. PMID: 27455215; PMCID: PMC6273287. 11: Govindharaj M, Arumugam S, Nirmala G, Bharadwaj M, Murugiyan K. Effect of Marine Basidiomycetes Fulvifomes sp.-Derived Ergosterol Peroxide on Cytotoxicity and Apoptosis Induction in MCF-7 Cell Line. J Fungi (Basel). 2019 Feb 13;5(1):16. doi: 10.3390/jof5010016. PMID: 30781890; PMCID: PMC6463160. 12: Kobori M, Yoshida M, Ohnishi-Kameyama M, Shinmoto H. Ergosterol peroxide from an edible mushroom suppresses inflammatory responses in RAW264.7 macrophages and growth of HT29 colon adenocarcinoma cells. Br J Pharmacol. 2007 Jan;150(2):209-19. doi: 10.1038/sj.bjp.0706972. Epub 2006 Dec 11. PMID: 17160010; PMCID: PMC2042906. 13: Wu HY, Yang FL, Li LH, Rao YK, Ju TC, Wong WT, Hsieh CY, Pivkin MV, Hua KF, Wu SH. Ergosterol peroxide from marine fungus Phoma sp. induces ROS-dependent apoptosis and autophagy in human lung adenocarcinoma cells. Sci Rep. 2018 Dec 18;8(1):17956. doi: 10.1038/s41598-018-36411-2. PMID: 30560887; PMCID: PMC6298985. 14: Ramos-Ligonio A, López-Monteon A, Trigos A. Trypanocidal activity of ergosterol peroxide from Pleurotus ostreatus. Phytother Res. 2012 Jun;26(6):938-43. doi: 10.1002/ptr.3653. Epub 2011 Nov 14. PMID: 22083593. 15: Wu QP, Xie YZ, Deng Z, Li XM, Yang W, Jiao CW, Fang L, Li SZ, Pan HH, Yee AJ, Lee DY, Li C, Zhang Z, Guo J, Yang BB. Ergosterol peroxide isolated from Ganoderma lucidum abolishes microRNA miR-378-mediated tumor cells on chemoresistance. PLoS One. 2012;7(8):e44579. doi: 10.1371/journal.pone.0044579. Epub 2012 Aug 30. PMID: 22952996; PMCID: PMC3431381. 16: Jeong YU, Park YJ. Ergosterol Peroxide from the Medicinal Mushroom Ganoderma lucidum Inhibits Differentiation and Lipid Accumulation of 3T3-L1 Adipocytes. Int J Mol Sci. 2020 Jan 10;21(2):460. doi: 10.3390/ijms21020460. PMID: 31936890; PMCID: PMC7014426. 17: Tan W, Pan M, Liu H, Tian H, Ye Q, Liu H. Ergosterol peroxide inhibits ovarian cancer cell growth through multiple pathways. Onco Targets Ther. 2017 Jul 13;10:3467-3474. doi: 10.2147/OTT.S139009. PMID: 28761355; PMCID: PMC5518915. 18: Bu M, Cao T, Li H, Guo M, Yang BB, Zeng C, Hu L. Synthesis of 5α,8α-Ergosterol Peroxide 3-Carbamate Derivatives and a Fluorescent Mitochondria-Targeting Conjugate for Enhanced Anticancer Activities. ChemMedChem. 2017 Mar 17;12(6):466-474. doi: 10.1002/cmdc.201700021. Epub 2017 Mar 9. PMID: 28198103. 19: Russo A, Cardile V, Piovano M, Caggia S, Espinoza CL, Garbarino JA. Pro- apoptotic activity of ergosterol peroxide and (22E)-ergosta-7,22-dien-5alpha- hydroxy-3,6-dione in human prostate cancer cells. Chem Biol Interact. 2010 Mar 30;184(3):352-8. doi: 10.1016/j.cbi.2010.01.032. Epub 2010 Jan 25. PMID: 20100469. 20: Han J, Sohn EJ, Kim B, Kim S, Won G, Yoon S, Lee J, Kim MJ, Lee H, Chung K, Kim SH. Upregulation of death receptor 5 and activation of caspase 8/3 play a critical role in ergosterol peroxide induced apoptosis in DU 145 prostate cancer cells. Cancer Cell Int. 2014 Nov 30;14(1):117. doi: 10.1186/s12935-014-0117-5. PMID: 25506265; PMCID: PMC4265345.