AUTHOR=Zhou Rong , Liao Xiaojian , Li Hangbin , Li Jing , Feng Pengju , Zhao BingXin , Xu Shihai 

TITLE=Isolation and Synthesis of Misszrtine A: A Novel Indole Alkaloid From Marine Sponge-Associated Aspergillus sp. SCSIO XWS03F03

JOURNAL=Frontiers in Chemistry

VOLUME=6

YEAR=2018

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2018.00212

DOI=10.3389/fchem.2018.00212

ISSN=2296-2646

ABSTRACT=<p>A novel indole alkaloid, misszrtine A (<bold>1</bold>), was isolated from marine sponge-derived fungus <italic>Aspergillus</italic> sp. SCSIO XWS03F03. The planar structure of <bold>1</bold> was assigned by analysis of spectroscopic data, the absolute configuration of which was unambiguously determined by total synthesis. Compound <bold>1</bold> represents the first example of <italic>N</italic>-isopentenyl tryptophan methyl ester with a phenylpropanoic amide arm, which exhibited a potent antagonistic activity on HL60 (IC<sub>50</sub> = 3.1 μM) and LNCaP (IC<sub>50</sub> = 4.9 μM) cell lines. Bioactivity evaluation reveals that functional group on indole nitrogen of <bold>1</bold> has a great effect on its cytotoxity, which provides a mean to probe the structure-activity relationships of <bold>1</bold>.</p>