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Issue 5, 2017
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New compounds from a hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4

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Abstract

Three new quinazoline derivatives (1–3), one new oxepin-containing natural product (4) and four new cyclopenin derivatives (5–7 and 9) have been isolated from an EtOAc extract of the Taiwan Kueishantao hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4. Their planar structures were established by HRMS, 1D and 2D NMR spectroscopic data analyses. The absolute configurations for compounds 1 and 4 were determined by chiral phase HPLC analysis of their hydrolysis products. The absolute configurations of 2, 3 and 7 were defined mainly by comparison of the quantum chemical TDDFT calculated and the experimental ECD spectra, and the absolute configuration of 5 was deduced from comparison of the optical rotation values reported in the literature. The presence of two atropisomers of 5 was established by NOE analyses. The Ile & Val units in compounds 1–3 allowed the assignment of a new quinazoline skeleton and it's the first time the configuration of isoleucine in the quinazoline skeleton was defined. A series of 7-methoxy cyclopenin derivatives were reported for the first time in this study. The bioevaluation of compounds 5, 7, 8 and 9 revealed inhibitory activities against E. coli at MIC values around 32 μg mL−1.

Graphical abstract: New compounds from a hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4

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Supplementary files

Article information


Submitted
01 Nov 2016
Accepted
03 Jan 2017
First published
03 Jan 2017

Org. Biomol. Chem., 2017,15, 1155-1163
Article type
Paper

New compounds from a hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4

C. Pan, Y. Shi, X. Chen, C. A. Chen, X. Tao and B. Wu, Org. Biomol. Chem., 2017, 15, 1155
DOI: 10.1039/C6OB02374F

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