(+)- and (−)-Eurotone A: A pair of enantiomeric polyketide dimers from a marine-derived fungus Eurotium sp. SCSIO F452

[Display omitted] •(±)-Eurotone A was identified from the marine fungus Eurotium sp. SCSIO F452.•(±)-Eurotone A was a pair of spirodihydrobenzanthracene enantiomers.•The absolute configuration of (±)-eurotone A was evidenced by ECD calculations. (±)-Eurotone A [(±)-1], a pair of new enantiomeric pol...

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Bibliographic Details
Published in:Tetrahedron letters 2019-06, Vol.60 (24), p.1600-1603
Main Authors: Zhong, Wei-Mao, Wang, Jun-Feng, Wei, Xiao-Yi, Zeng, Qi, Chen, Xia-Yu, Xiang, Yao, Tian, Xin-Peng, Zhang, Si, Long, Li-Juan, Wang, Fa-Zuo
Format: Article
Language:English
Subjects:
Enantiomeric dimers
Marine-derived fungi
Polyketide
Structure elucidation
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Summary:[Display omitted] •(±)-Eurotone A was identified from the marine fungus Eurotium sp. SCSIO F452.•(±)-Eurotone A was a pair of spirodihydrobenzanthracene enantiomers.•The absolute configuration of (±)-eurotone A was evidenced by ECD calculations. (±)-Eurotone A [(±)-1], a pair of new enantiomeric polyketide dimers, as well as six known biogenetically related polyketides (2–7) were isolated from a marine-derived fungus Eurotium sp. SCSIO F452. Their structures were determined by comprehensive spectroscopic methods, X-ray diffraction and quantum chemical calculations. Compound 1 represented the first pair of spirodihydrobenzanthracene enantiomers isolated from marine fungi with their absolute configurations assigned. A plausible biosynthetic pathway involving a key acid-mediated dimerization was proposed for 1. The antioxidative activities of the new enantiomers were evaluated.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.05.025