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Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A⁻C from the Gorgonian-Derived Penicillium chrysogenum Fungus.
Mar Drugs. 2019 Apr 26; 17(5)MD

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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Authors+Show Affiliations

Xu WF
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. Xuweifeng_u@163.com. Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266200, China. Xuweifeng_u@163.com.
Mao N
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. 13012456579@163.com. Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266200, China. 13012456579@163.com.
Xue XJ
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. xiaoxuexiaojia@163.com. Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266200, China. xiaoxuexiaojia@163.com.
Qi YX
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. qiyuexuan9475@163.com. Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266200, China. qiyuexuan9475@163.com.
Wei MY
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. mywei95@126.com. Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266200, China. mywei95@126.com. College of Food Science and Engineering, Ocean University of China, Qingdao 266003, China. mywei95@126.com.
Wang CY
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. changyun@ouc.edu.cn. Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266200, China. changyun@ouc.edu.cn.
Shao CL
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. shaochanglun@163.com. Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266200, China. shaochanglun@163.com.

MeSH

AlkaloidsAnimalsAnthozoaAnti-Bacterial AgentsAntifungal AgentsBacteriaCircular DichroismDiketopiperazinesFungiMicrobial Sensitivity TestsMolecular ConformationMolecular StructurePenicillium chrysogenumProton Magnetic Resonance Spectroscopy

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31035506

Citation

Xu, Wei-Feng, et al. "Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A⁻C From the Gorgonian-Derived Penicillium Chrysogenum Fungus." Marine Drugs, vol. 17, no. 5, 2019.
Xu WF, Mao N, Xue XJ, et al. Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A⁻C from the Gorgonian-Derived Penicillium chrysogenum Fungus. Mar Drugs. 2019;17(5).
Xu, W. F., Mao, N., Xue, X. J., Qi, Y. X., Wei, M. Y., Wang, C. Y., & Shao, C. L. (2019). Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A⁻C from the Gorgonian-Derived Penicillium chrysogenum Fungus. Marine Drugs, 17(5). https://doi.org/10.3390/md17050250
Xu WF, et al. Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A⁻C From the Gorgonian-Derived Penicillium Chrysogenum Fungus. Mar Drugs. 2019 Apr 26;17(5) PubMed PMID: 31035506.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A⁻C from the Gorgonian-Derived Penicillium chrysogenum Fungus. AU - Xu,Wei-Feng, AU - Mao,Ning, AU - Xue,Xiao-Jia, AU - Qi,Yue-Xuan, AU - Wei,Mei-Yan, AU - Wang,Chang-Yun, AU - Shao,Chang-Lun, Y1 - 2019/04/26/ PY - 2019/04/08/received PY - 2019/04/20/revised PY - 2019/04/24/accepted PY - 2019/5/1/entrez PY - 2019/5/1/pubmed PY - 2019/8/27/medline KW - Penicillium chrysogenum KW - VCD method KW - absolute configurations KW - diketopiperazine alkaloids KW - oxepine‐containing JF - Marine drugs JO - Mar Drugs VL - 17 IS - 5 N2 - 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. SN - 1660-3397 UR - https://www.unboundmedicine.com/medline/citation/31035506/Structures_and_Absolute_Configurations_of_Diketopiperazine_Alkaloids_Chrysopiperazines_A⁻C_from_the_Gorgonian_Derived_Penicillium_chrysogenum_Fungus_ DB - PRIME DP - Unbound Medicine ER -