Chaetoglobosin A

Chaetoglobosin A is a fungal isolate with anticancer activity in vitro. Derivatives of the compound include MBJ-0038, MBJ-0039, and MBJ-0040.

Biosynthesis

Chaetoglobosin A biosynthesis begins with a product from hybrid PKS-NRPS encoded by the gene CHGG_01239, followed by multiple oxidations which form different intermediates depending on the order of functional groups oxidized. The PKS-NRPS product undergoes a diels alder, to form I and is subsequently oxidized in different paths as shown in the scheme. Either the epoxide is created first to form IV, followed by di-hydroxylation to form 20-dihydrochaetoglobosin A, and a final oxidation of one hydroxyl to ketone to form chaetoglobosin A, or di-hydroxylation of occurs first, forming cytoglobosin D, followed by one hydroxyl oxidation to form chaetoglobosin J, and lastly epoxidation to form chaetoglobosin A. Epoxidation of can also occur prior to hydroxyl oxidation to form.