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

ABSTRACT: A novel indole alkaloid, misszrtine A (1), was isolated from marine sponge-derived fungus Aspergillus sp. SCSIO XWS03F03. The planar structure of 1 was assigned by analysis of spectroscopic data, the absolute configuration of which was unambiguously determined by total synthesis. Compound 1 represents the first example of N-isopentenyl tryptophan methyl ester with a phenylpropanoic amide arm, which exhibited a potent antagonistic activity on HL60 (IC50 = 3.1 ?M) and LNCaP (IC50 = 4.9 ?M) cell lines. Bioactivity evaluation reveals that functional group on indole nitrogen of 1 has a great effect on its cytotoxity, which provides a mean to probe the structure-activity relationships of 1.

SUBMITTER: Zhou R

PROVIDER: S-EPMC6008316 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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

Zhou Rong R Liao Xiaojian X Li Hangbin H Li Jing J Feng Pengju P Zhao BingXin B Xu Shihai S

Frontiers in chemistry 20180613

A novel indole alkaloid, misszrtine A (1), was isolated from marine sponge-derived fungus Aspergillus sp. SCSIO XWS03F03. The planar structure of 1 was assigned by analysis of spectroscopic data, the absolute configuration of which was unambiguously determined by total synthesis. Compound 1 represents the first example of N-isopentenyl tryptophan methyl ester with a phenylpropanoic amide arm, which exhibited a potent antagonistic activity on HL60 (IC50</su ...[more]

PMID: 29951479

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