Butyrolactone I

Butyrolactone I is a secondary metabolite from A. terreus that acts as an ATP-competitive inhibitor of cyclin-dependent kinase 1 (Cdk1, IC50 = 20 µg/ml in PC-14 cells). It induces dose-dependent G2/M arrest, inhibits DNA synthesis, and decreases Cdk1 protein expression in vitro. Butyrolactone I has antitumor effects in non-small cell lung, small cell lung, and prostate cancer cell lines (mean IC50 = 50 µg/ml). It inhibits in vitro Cdk1 phosphorylation of tau and in vivo phosphorylation of transcription factor E2F-1. Additionally, exogenous application of butyrolactone I to A. terreus cultures increases biogenesis of the secondary metabolites lovastatin (Cay-10010338) and conidiation in a quorum-sensing manner.Formal Name: (2R)-2,5-dihydro-4-hydroxy-2-[[4-hydroxy-3-(3-methyl-2-buten-1-yl)phenyl]methyl]-3-(4-hydroxyphenyl)-5-oxo-2-furancarboxylic acid, methyl ester. CAS Number: 87414-49-1. Molecular Formula: C24H24O7. Formula Weight: 424.5. Purity: >90%. Formulation: (Request formulation change), A solid. Solubility: DMF: soluble, DMSO: soluble, Ethanol: soluble, Methanol: soluble. SMILES: O=C1O[C@@](CC2=CC(C/C=C(C)/C)=C(O)C=C2)(C(OC)=O)C(C3=CC=C(O)C=C3)=C1O. InChi Code: InChI=1S/C24H24O7/c1-14(2)4-6-17-12-15(5-11-19(17)26)13-24(23(29)30-3)20(21(27)22(28)31-24)16-7-9-18(25)10-8-16/h4-5,7-12,25-27H,6,13H2,1-3H3/t24-/m1/s1. InChi Key: NGOLMNWQNHWEKU-XMMPIXPASA-N. Origin: Fungus/Aspergillus sp..