(±)-Terreinlactone A, a Pair of 3-Substituted δ-Lactone Enantiomers Derived from Terrein from the Fungus Aspergillus terreus.


Zhang X, Wu Z, Lai Y, Li D, Wang J, Luo Z, Xue Y, Zhu H, Chen C, Zhang Y.
Chem Pharm Bull (Tokyo). 2018 Jul 1;66(7):764-767


Terreinlactone A (1a/1b), a pair of 3-substituted δ-lactone enantiomers, and terreinlactone B (2), a new biosynthetic intermediate of 1a/1b, were isolated from Aspergillus terreus, along with their biosynthetic precursor (+)-terrein (3) and (+)-isoterrein (4). Compounds 1a and 1b were separated by using a Daicel chiral-pak ASH column eluting with n-hexane-EtOH (80 : 20). The structures of 1a/1b with absolute configurations were determined by comprehensive spectroscopic analyses and electronic circular dichroic (ECD) calculations. Terreinlactone A (1) represents the first example of 1,5-seco-terrein and a biogenetic pathway is proposed from the precursor terrein via the intermediated terreinlactone B (2).


Aspergillus terreus; electronic circular dichroic (ECD) calculation; enantiomer; terrein; δ-lactone