Three Pairs of New Spirocyclic Alkaloid Enantiomers From the Marine-Derived Fungus Eurotium sp. SCSIO F452

Weimao Zhong; Weimao Zhong; Junfeng Wang; Xiaoyi Wei; Tingdan Fu; Yuchan Chen; Qi Zeng; Qi Zeng; Zhonghui Huang; Zhonghui Huang; Xinan Huang; Weimin Zhang; Si Zhang; Lijuan Long; Fazuo Wang

doi:10.3389/fchem.2019.00350

Frontiers in Chemistry (May 2019)

Three Pairs of New Spirocyclic Alkaloid Enantiomers From the Marine-Derived Fungus Eurotium sp. SCSIO F452

Weimao Zhong,
Weimao Zhong,
Junfeng Wang,
Xiaoyi Wei,
Tingdan Fu,
Yuchan Chen,
Qi Zeng,
Qi Zeng,
Zhonghui Huang,
Zhonghui Huang,
Xinan Huang,
Weimin Zhang,
Si Zhang,
Lijuan Long,
Fazuo Wang

Affiliations

Weimao Zhong: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China
Weimao Zhong: College of Earth and Planetary Sciences, University of Chinese Academy of Sciences, Beijing, China
Junfeng Wang: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China
Xiaoyi Wei: Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, China
Tingdan Fu: Institute of Tropical Medicine, Guangzhou University of Chinese Medicine, Guangzhou, China
Yuchan Chen: State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou, China
Qi Zeng: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China
Qi Zeng: College of Earth and Planetary Sciences, University of Chinese Academy of Sciences, Beijing, China
Zhonghui Huang: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China
Zhonghui Huang: College of Earth and Planetary Sciences, University of Chinese Academy of Sciences, Beijing, China
Xinan Huang: Institute of Tropical Medicine, Guangzhou University of Chinese Medicine, Guangzhou, China
Weimin Zhang: State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou, China
Si Zhang: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China
Lijuan Long: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China
Fazuo Wang: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China

DOI: https://doi.org/10.3389/fchem.2019.00350
Journal volume & issue: Vol. 7

Abstract

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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 in Frontiers in Chemistry

ISSN: 2296-2646 (Online)
Publisher: Frontiers Media S.A.
Country of publisher: Switzerland
LCC subjects: Science: Chemistry
Website: http://journal.frontiersin.org/journal/chemistry

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