title: New compounds from a hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4.
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.
authors.affiliation: Ocean College, Zhejiang University, Hangzhou 310058, China. wubin@zju.edu.cn.
authors.forename: Chengqian
authors.identifier: http://orcid.org/0000-0001-9306-2419
authors.initials: C
authors.lastname: Pan
authors.affiliation: Ocean College, Zhejiang University, Hangzhou 310058, China. wubin@zju.edu.cn.
authors.forename: Yutong
authors.initials: Y
authors.lastname: Shi
authors.affiliation: Ocean College, Zhejiang University, Hangzhou 310058, China. wubin@zju.edu.cn.
authors.forename: Xuegang
authors.initials: X
authors.lastname: Chen
authors.affiliation: Institute of Marine Geology and Chemistry, National Sun Yat-sen University, Kaohsiung 80424, Taiwan, Republic of China.
authors.forename: Chen-Tung Arthur
authors.initials: CA
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China.
authors.forename: Xinyi
authors.initials: X
authors.lastname: Tao
authors.affiliation: Ocean College, Zhejiang University, Hangzhou 310058, China. wubin@zju.edu.cn.
authors.forename: Bin
authors.initials: B
authors.lastname: Wu
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001230:Aspergillus / Q000737:chemistry*; D001570:Benzodiazepinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004926:Escherichia coli / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010082:Oxepins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D011799:Quinazolines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D001570:Benzodiazepinones; D001688:Biological Products; D010082:Oxepins; D011799:Quinazolines; C007200:cyclopenin