Citriquinolinones A and B: Rare Isoquinolinone-Embedded Citrinin Analogues and Related Metabolites from the Deep-Sea-Derived <i>Aspergillus versicolor</i> 170217
Shui-Hua Lin,
Qing-Xiang Yan,
Yong Zhang,
Tai-Zong Wu,
Zheng-Biao Zou,
Qing-Mei Liu,
Jia-Yang Jiang,
Ming-Min Xie,
Lin Xu,
You-Jia Hao,
Zhu Liu,
Guang-Ming Liu,
Xian-Wen Yang
Affiliations
Shui-Hua Lin
Department of Pharmacy, Quanzhou Medical College, 2 Anji Road, Quanzhou 362000, China
Qing-Xiang Yan
Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
Yong Zhang
Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
Tai-Zong Wu
Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
Zheng-Biao Zou
Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
Qing-Mei Liu
College of Food and Biological Engineering, Jimei University, 43 Yindou Road, Xiamen 361021, China
Jia-Yang Jiang
Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
Ming-Min Xie
Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
Lin Xu
Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
You-Jia Hao
Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
Zhu Liu
College of Life Sciences, Hainan University, 58 People’s Avenue, Haikou 570228, China
Guang-Ming Liu
College of Food and Biological Engineering, Jimei University, 43 Yindou Road, Xiamen 361021, China
Xian-Wen Yang
Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
A systematic chemical investigation of the deep-sea-derived fungus Aspergillus versicolor 170217 resulted in the isolation of six new (1–6) and 45 known (7–51) compounds. The structures of the new compounds were established on the basis of exhaustive analysis of their spectroscopic data and theoretical–statistical approaches including GIAO-NMR, TDDFT-ECD/ORD calculations, DP4+ probability analysis, and biogenetic consideration. Citriquinolinones A (1) and B (2) feature a unique isoquinolinone-embedded citrinin scaffold, representing the first exemplars of a citrinin–isoquinolinone hybrid. Dicitrinones K–L (3–4) are two new dimeric citrinin analogues with a rare CH-CH3 bridge. Biologically, frangula-emodin (32) and diorcinol (17) displayed remarkable anti-food allergic activity with IC50 values of 7.9 ± 3.0 μM and 13.4 ± 1.2 μM, respectively, while diorcinol (17) and penicitrinol A (20) exhibited weak inhibitory activity against Vibrio parahemolyticus, with MIC values ranging from 128 to 256 μM.
