title: Versiquinazolines A-K, Fumiquinazoline-Type Alkaloids from the Gorgonian-Derived Fungus Aspergillus versicolor LZD-14-1.
abstract: Eleven fumiquinazoline-type alkaloids, namely, versiquinazolines A-K (1-11), along with cottoquinazolines B-D, were isolated from the gorgonian-derived fungus Aspergillus versicolor LZD-14-1. Their structures were determined by extensive analyses of the spectroscopic data (1D and 2D NMR, HRESIMS), in addition to the experimental and calculated ECD data and X-ray single-crystal diffraction analysis for the assignments of the absolute configurations. Versiquinazolines A, B, and F (1, 2, and 6), bearing a methanediamine or an aminomethanol unit and representing a unique subtype of fumiquinazolines, were found from nature for the first time. Possible biogenetic relationships of the versiquinazolines are postulated. In addition, the structures of cottoquinazolines B (12), D (13), and C (14) should be revised to the enantiomers. Compounds 1, 2, 7, and 11 exhibited inhibitory activities against thioredoxin reductase (IC50values ranging from 12 to 20 μM).
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, Institute of Ocean Research, Peking University , Beijing, 100191, People's Republic of China.
authors.forename: Zhongbin
authors.initials: Z
authors.lastname: Cheng
authors.affiliation: School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou, Guangdong 510006, People's Republic of China.
authors.forename: Lanlan
authors.initials: L
authors.lastname: Lou
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, Institute of Ocean Research, Peking University , Beijing, 100191, People's Republic of China.
authors.forename: Dong
authors.initials: D
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, Institute of Ocean Research, Peking University , Beijing, 100191, People's Republic of China.
authors.forename: Xiaodan
authors.initials: X
authors.lastname: Li
authors.affiliation: Institute für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf , 40225 Düsseldorf, Germany.
authors.forename: Peter
authors.initials: P
authors.lastname: Proksch
authors.affiliation: School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou, Guangdong 510006, People's Republic of China.
authors.forename: Sheng
authors.initials: S
authors.lastname: Yin
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, Institute of Ocean Research, Peking University , Beijing, 100191, People's Republic of China.
authors.forename: Wenhan
authors.initials: W
authors.lastname: Lin
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001230:Aspergillus / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011799:Quinazolines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism; D013880:Thioredoxin-Disulfide Reductase / Q000037:antagonists & inhibitors
chemical_list: D000470:Alkaloids; D011799:Quinazolines; C557953:cottoquinazoline B; C557940:cottoquinazoline D; D013880:Thioredoxin-Disulfide Reductase