Waikikiamides A–C: Complex Diketopiperazine Dimer and Diketopiperazine–Polyketide Hybrids from a Hawaiian Marine Fungal Strain <i>Aspergillus</i> sp. FM242
Fuqian Wang, Ariel M. Sarotti, Guangde Jiang, José C. Huguet‐Tapia, Shao‐Liang Zheng, Xiaohua Wu, Chun‐Shun Li, Yousong Ding, Shugeng Cao
Abstract
Waikikiamides A–C (1–3), structurally complex diketopiperazine derivatives, and putative biogenic precursors, (+)-semivioxanthin (4), notoamide F (5), and (−)-notoamide A (6), were isolated from Aspergillus sp. FM242. 1 and 2, bearing a hendecacyclic ring system, represent a novel skeleton. 3 features the first unique heterodimer of two notoamide analogs with an N–O–C bridge. Compounds 1 and 3 exhibit antiproliferative activity with IC50 values in the range of 0.56 to 1.86 μM. The gene clusters mined from the sequenced genome support their putative biosynthetic pathways.
Topics & Concepts
StereochemistryPolyketideDimerChemistryAspergillusStrain (injury)Marine fungiGeneRing (chemistry)Gene clusterBiologyBiochemistryBiosynthesisMicrobiologyBotanyOrganic chemistryAnatomyMicrobial Natural Products and BiosynthesisMarine Sponges and Natural ProductsSynthetic Organic Chemistry Methods