A fungal metabolite with diverse biological activities
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Ilicicolin F

Item No. 29850

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[(2E,4E)-5-[(1S,2S,3S,6R)-3-(acetyloxy)-1,2,6-trimethyl-5-oxocyclohexyl]-3-methyl-2,4-pentadien-1-yl]-5-chloro-2,4-dihydroxy-6-methyl-benzaldehyde
CAS Number
22738-98-3
Synonyms
  • LL-Z 1272ζ
Molecular Formula
C25H31ClO6
Formula Weight
463.0
Purity
≥70%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Dichloromethane: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C1[C@H](C)[C@](/C=C/C(C)=C/CC2=C(O)C(C=O)=C(C)C(Cl)=C2O)(C)[C@H](C)[C@@H](OC(C)=O)C1
InChi Code
InChI=1S/C25H31ClO6/c1-13(7-8-18-23(30)19(12-27)14(2)22(26)24(18)31)9-10-25(6)15(3)20(29)11-21(16(25)4)32-17(5)28/h7,9-10,12,15-16,21,30-31H,8,11H2,1-6H3/b10-9+,13-7+/t15-,16+,21-,25+/m0/s1
InChi Key
ACSLMZYXJATICN-IRMIYARYSA-N
Origin
Fungus/Unidentified sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $329

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    Product Description

    Ilicicolin F is a fungal metabolite that has been found in Fusarium and has diverse biological activities.1,2,3 It inhibits T. vivax alternative oxidase and the E. coli ubiquinol oxidase cytochrome bo (IC50s = 0.43 and 0.37 µM, respectively) but not the E. coli ubiquinol oxidase cytochrome bd (IC50 = 85 µM).2 Ilicicolin F is active against the fungi A. fumigatus and C. albicans (MICs = 1.66-3.33 and 6.66-13.33 µg/ml, respectively).4 It is cytotoxic to HeLa cells with an EC50 value of 0.003 µg/ml.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ellestad, G.A., Evans, R.H., Jr., and Kunstmann, M.P. Some new terpenoid metabolites from an unidentified fusarium species. Tetrahedron 25(6), 1323-1334 (1969).

    2. Mogi, T., Ui, H., Shiomi, K., et al. Antibiotics LL-Z1272 identified as novel inhibitors discriminating bacterial and mitochondrial quinol oxidases. Biochim. Biophys. Acta 1787(2), 129-133 (2009).

    3. Bal-Tembe, S., Kundu, S., Roy, K., et al. Activity of the ilicicolins against plant pathogenic fungi. Pestic. Sci. 55(6), 645-647 (1999).

    4. Subko, K., Kildgaard, S., Vicente, F., et al. Bioactive ascochlorin analogues from the marine-derived fungus Stilbella fimetaria. Mar. Drugs 19(2), 46 (2021).

    5. Hayakawa, S., Minato, H., and Katagiri, K. The ilicicolins, antibiotics from Cylindrocladium ilicicola. J. Antibiot. (Tokyo) 24(9), 653-654 (1971).