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  • Title: Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A⁻C from the Gorgonian-Derived Penicillium chrysogenum Fungus.
    Author: Xu WF, Mao N, Xue XJ, Qi YX, Wei MY, Wang CY, Shao CL.
    Journal: Mar Drugs; 2019 Apr 26; 17(5):. PubMed ID: 31035506.
    Abstract:
    Three new diketopiperazine alkaloids, including two oxepine-containing diketopiperazines, chrysopiperazines A and B (1 and 2), and one quinazoline-containing diketopiperazine, chrysopiperazine C (5), together with three known analogues (3, 4, and 6), were isolated from the gorgonian-derived Penicillium chrysogenum fungus. The relative and absolute configurations of C-3 and C-15 in 1 and 2, C-3 and C-14 in 5 were established by NOE modified Marfey's analysis and electronic circular dichroism (ECD) calculations. Particularly, the absolute configurations of C-19 in 1 and 3, which was very challenging to be identified due to the flexible conformation in a short aliphatic chain, were successfully determined by the vibrational circular dichroism (VCD) method, supplying with a reliable and optional method to define the absolute configurations. Additionally, this is the first report on oxepine-containing diketopiperazines from the genus Penicillium.
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