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Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A–C from the Gorgonian-Derived Penicillium chrysogenum Fungus

1,2,†, 1,2,†, 1,2, 1,2, 1,2,3, 1,2 and 1,2,*
1
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
2
Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266200, China
3
College of Food Science and Engineering, Ocean University of China, Qingdao 266003, China
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Mar. Drugs 2019, 17(5), 250; https://doi.org/10.3390/md17050250
Received: 8 April 2019 / Revised: 20 April 2019 / Accepted: 24 April 2019 / Published: 26 April 2019
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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. View Full-Text
Keywords: diketopiperazine alkaloids; oxepine-containing; Penicillium chrysogenum; absolute configurations; VCD method diketopiperazine alkaloids; oxepine-containing; Penicillium chrysogenum; absolute configurations; VCD method
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Xu, W.-F.; Mao, N.; Xue, X.-J.; Qi, Y.-X.; Wei, M.-Y.; Wang, C.-Y.; Shao, C.-L. Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A–C from the Gorgonian-Derived Penicillium chrysogenum Fungus. Mar. Drugs 2019, 17, 250.

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