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

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.

SUBMITTER: Zhong W

PROVIDER: S-EPMC6536037 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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

Zhong Weimao W Wang Junfeng J Wei Xiaoyi X Fu Tingdan T Chen Yuchan Y Zeng Qi Q Huang Zhonghui Z Huang Xinan X Zhang Weimin W Zhang Si S Long Lijuan L Wang Fazuo F

Frontiers in chemistry 20190520

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 cycloaddit ...[more]

PMID: 31165062

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