1. Three Pairs of New Spirocyclic Alkaloid Enantiomers From the Marine-Derived Fungus Eurotium sp. SCSIO F452
- Author
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Weimao Zhong, Junfeng Wang, Xiaoyi Wei, Tingdan Fu, Yuchan Chen, Qi Zeng, Zhonghui Huang, Xinan Huang, Weimin Zhang, Si Zhang, Lijuan Long, and Fazuo Wang
- Subjects
Eurotium sp. SCSIO F452 ,spirocyclic alkaloid enantiomers ,antioxidative and cytotoxic activities ,Diels-Alder cycloaddition ,molecular docking ,Chemistry ,QD1-999 - Abstract
Three pairs of new spirocyclic alkaloid enantiomers eurotinoids A–C (1–3), as well as a known biogenetically related racemate dihydrocryptoechinulin D (4) were isolated from a marine-derived fungus Eurotium sp. SCSIO F452. Their structures were determined by spectroscopic analyses and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 represent the first two “meta” products from a non-stereoselective [4 + 2] Diels-Alder cycloaddition presumably between an enone group of a diketopiperazine alkaloid and a diene group of a benzaldehyde derivative via a new head-to-tail coupling mode biosynthetically, while 3 and 4 were “ortho” products. Their enantiomers exhibited different antioxidative and cytotoxic activities. The modes of action were investigated by a preliminary molecular docking study.
- Published
- 2019
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