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Isolation, Structure Elucidation and Total Synthesis of Two New Alkaloids from the Marine-Derived Fungus Aspergillus sp.

Marine natural products,Marine-derived alkaloids

Isolation, Structure Elucidation and Total Synthesis of Two New Alkaloids from the Marine-Derived Fungus Aspergillus sp.



Li Xu^{1, 2}, Feng-Wei Guo^{1, 2}, Qun Zhang^{1, 2}, Yang-Yang Guo^{1, 2}, Wei-Feng Xu^{1, 2}, Xue-Mei Hou^{1, 2}, Mei-Yan Wei^{1, 2}, Chang-Yun Wang^{1, 2}, Chang-Lun Shao*<sup>1, 2

1</sup> Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People’s Republic of China.

² Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266237, People’s Republic of China.

* Email: shaochanglun@163.com.



     Marine natural products have been proven to be rich sources of structurally novel and biologically active compounds, and they have become one of the major chemical entities for drug discovery^[1]. Recently, marine-derived alkaloids have generated increasing research interest, due to their promising biological activities including cytotoxic, antibacterial, antifungal, antiviral activities^[2]. In addition, marine-derived alkaloids have also become excellent targets for synthetic work owing to their structural diversity.

     Nowadays, LC-MS/MS-dependent molecular networking has been developed as a powerful approach that has advanced natural product research involving dereplication and discovery^[3]. During our ongoing search for new diversity structural compounds from marine fungi, under the guidance of MS/MS-based molecular networking, two new alkaloids were isolated from the marine-derived fungus Aspergillus sp. Their structures including absolute configurations were elucidated by extensive spectroscopic methods, single crystal X-ray diffraction and ECD calculations. The total synthesis of two alkaloids from Aspergillus sp. were also described.

    This work was supported by the Program of National Natural Science Foundation of China (Nos. U1706210, 41776141, 41906090, 42006092 and 41322037), the Program of Natural Science Foundation of Shandong Province of China (No. ZR2019BD047), the Marine S&T Fund of Shandong Province for Pilot National Laboratory for Marine Science and Technology (Qingdao) (No. 2018SDKJ0403-2), and the Taishan Scholars Program, China (No. tsqn20161010).





References

1. Xuemei Hou, Tingmei Liang, Changyun Wang, Changlun Shao and Zhiyong Guo, Discovery, Absolute Assignments, and Total Synthesis of Asperversiamides A-C and Their Potent Activity against Mycobacterium marinum, Chemical Communications, 2019, 55, 1104−1107.


2. Ibrahim, Sabrin RM, and Gamal A. Mohamed, Marine Pyridoacridine Alkaloids: Biosynthesis and Biological Activities, Chemistry & Biodiversity, 2016, 13, 37−47.

      3.  Jane Y. Yang, Laura M. Sanchez, Christopher M. Rath, Xueting Liu, Paul D. Boudreau, Nicole Bruns, Evgenia Glukhov, Anne Wodtke, Rafael de Felicio, Amanda Fenner,                    Weng Ruh Wong, Roger G. Linington, Lixin Zhang, Hosana M. Debonsi, William H. Gerwick and Pieter C. Dorrestein, Molecular Networking as a Dereplication                               Strategy, Journal of Natural Products, 2013, 76, 1686−1699.