A mycotoxin
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Emestrin

Item No. 29970

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,2R,6aS,20S,21R,22bS)-6a,22b-dihydro-2,16,20-trihydroxy-12-methoxy-25-methyl-2H,8H,20H,22H-1,21-epidithio-21,1-(iminomethano)-9,13:15,19-dimetheno-4,7,14-trioxa-22a-azacyclononadec[cd]azulene-8,22,26-trione
CAS Number
97816-62-1
Molecular Formula
C27H22N2O10S2
Formula Weight
598.6
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
OC(C=CC([C@@H]([C@]1(SS2)N(C)C([C@]2([C@H](O)C3=COC=CC(OC4=O)[C@]35[H])N5C1=O)=O)O)=C6)=C6OC7=CC4=CC=C7OC
InChi Code
InChI=1S/C27H22N2O10S2/c1-28-24(34)27-22(32)14-11-37-8-7-17-20(14)29(27)25(35)26(28,40-41-27)21(31)12-3-5-15(30)18(9-12)38-19-10-13(23(33)39-17)4-6-16(19)36-2/h3-11,17,20-22,30-32H,1-2H3/t17?,20-,21-,22+,26+,27+/m0/s1
InChi Key
UWWYWUMDYAWTKK-REDDWEFJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Emestrin is a mycotoxin originally isolated from E. striata that has antimicrobial, immunomodulatory, and cytotoxic activities.1,2,3,4,5 It is active against the fungi C. albicans and C. neoformans, as well as the bacteria E. coli, S. aureus, and methicillin-resistant S. aureus (MRSA; IC50s = 3.94, 0.6, 2.21, 4.55, and 2.21 µg/ml, respectively).2 Emestrin is a chemokine (C-C motif) receptor 2 (CCR2) antagonist (IC50 = 5.4 µM in a radioligand binding assay using isolated human monocytes).3 Emestrin (0.1 µg/ml) induces apoptosis in HL-60 cells.4 It induces heart, thymus, and liver tissue necrosis in mice when administered at doses ranging from 18 to 30 mg/kg.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Seya, H., Nakajima, S., Kawai, K.-i., et al. Structure and absolute configuration of emestrin, a new macrocyclic epidithiodioxopiperazine from Emericella striata. J. Chem. Soc. Chem. Commun. 10, 657-658 (1985).

    2. Herath, H.M.T.B., Jacob, M., Wilson, A.D., et al. New secondary metabolites from bioactive extracts of the fungus Armillaria tabescens. Nat. Prod. Res. 27(17), 1562-1568 (2013).

    3. Herath, K.B., Jayasuriya, H., Ondeyka, J.G., et al. Isolation and structures of novel fungal metabolites as chemokine receptor (CCR2) antagonists. J. Antibiot. (Tokyo) 58(11), 686-694 (2005).

    4. Ueno, Y., Umemori, K., Niimi, E.-c., et al. Induction of apoptosis by T-2 toxin and other natural toxins in HL-60 human promyelotic leukemia cells. Nat. Toxins 3(3), 129-137 (1995).

    5. Terao, K., Ito, E., Kawai, K.-i., et al. Experimental acute poisoning in mice induced by emestrin, a new mycotoxin isolated from Emericella species. Mycopathologia 112(2), 71-79 (1990).