Terrein

Terrein is a fungal metabolite produced by A. terreus with diverse biological activities. It reduces melanin production in Mel-Ab mouse melanocytes in a dose-dependent manner via ERK activation and downregulation of microphthalmia-associated transcription factor (MITF). Terrein inhibits proliferation of human keratinocytes and thins the epidermis in a skin equivalent model of psoriasis vulgaris. It is antimicrobial, inhibiting the growth of S. aureus, A. hydrophila, E. faecalis, A. flavus, A. alternata, B. sorokiniana, and P. drechsleri (MICs = 1-40 µg/ml). Terrein also inhibits growth of A549 lung cancer cells in a dose-dependent manner.Formal Name: 4S,5R-dihydroxy-3-(1E)-1-propen-1-yl-2-cyclopenten-1-one. CAS Number: 582-46-7. Synonyms: NSC 291308. Molecular Formula: C8H10O3. Formula Weight: 154.2. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: DMSO: Soluble, Methanol: Soluble. SMILES: O=C1[C@H](O)[C@@H](O)C(/C=C/C)=C1. InChi Code: InChI=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1. InChi Key: MHOOPNKRBMHHEC-HZIBQTDNSA-N.