An oxidized sterol with diverse biological activities
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Ergosterol Peroxide

Item No. 30860

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β,5α,8α,22E)-5,8-epidioxy-ergosta-6,22-dien-3-ol
CAS Number
2061-64-5
Synonyms
  • Ergosterol Endoperoxide
  • NSC 31324
Molecular Formula
C28H44O3
Formula Weight
428.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Methanol: soluble
SMILES
CC(C)[C@@H](C)/C=C/[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@@]3(OO4)C=C[C@@]54C[C@@H](O)CC[C@]5(C)[C@@]3([H])CC[C@@]21C
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
InChi Key
VXOZCESVZIRHCJ-KGHQQZOUSA-N
Origin
Plant/Unidentified sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    500 µg

    $90

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    1 mg

    $168

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    5 mg

    $653

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    Product Description

    Ergosterol peroxide is an oxidized sterol and derivative of ergosterol (Item No. 19850) that has been found in S. aspratus and has diverse biological activities.1,2,3,4,5 It is active against the P. falciparum chloroquine-sensitive strain FCA 20/GHA with an IC50 value of 8.2 µM.2 Ergosterol peroxide (6.25-50 µM) induces apoptosis in LNCaP and DU145 prostate cancer cells.3 It inhibits growth of SNU-1 gastric, SNU-354 hepatoma, and SNU-C4 colorectal cancer cells (IC50s = 18.7, 158.2, and 84.6 µM, respectively).6 Ergosterol peroxide (60 µM) 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 (TPA; Item No. 10008014) with an ID50 value of 0.2 mg/ear.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nielson, J.R., Fredrickson, E.K., Waller, T.C., et al. Sterol oxidation mediates stress-responsive Vms1 translocation to mitochondria. Mol. Cell 68(4), 673-685 (2017).

    2. Kuria, K.A.M., Chepkwony, H., Govaerts, C., et al. The antiplasmodial activity of isolates from Ajuga remota. J. Nat. Prod. 65(5), 789-793 (2002).

    3. Russo, A., Cardile, V., Piovano, M., et al. Pro-apoptotic activity of ergosterol peroxide and (22E)-ergosta-7,22-dien-5α-hydroxy-3,6-dione in human prostate cancer cells. Chem. Biol. Interact. 184(3), 352-358 (2010).

    4. Kobori, M., Yoshida, M., Ohnishi-Kameyama, M., et al. Ergosterol peroxide from an edible mushroom suppresses inflammatory responses in RAW264.7 macrophages and growth of HT29 colon adenocarcinoma cells. Br. J. Pharmacol. 150(2), 209-219 (2007).

    5. Yasukawa, K., Aoki, T., Takido, M., et al. Inhibitory effects of ergosterol isolated from the edible mushroom Hypsizigus marmoreus on TPA‐induced inflammatory ear oedema and tumour promotion in mice. Phytother. Res. 8(1), 10-13 (1994).

    6. Nam, K.S., Jo, Y.S., Kim, Y.H., et al. Cytotoxic activities of acetoxyscirpenediol and ergosterol peroxide from Paecilomyces tenuipes. Life Sci. 69(2), 229-237 (2001).