Amino Acid-Directed Strategy for Inducing the Marine-Derived Fungus Scedosporium apiospermum F41-1 to Maximize Alkaloid Diversity.

Org Lett 2017 09 24;19(18):4888-4891. Epub 2017 Aug 24.

School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou 510006, China.

By feeding various amino acids to the marine fungus Scedosporium apiospermum F41-1, 22 diverse alkaloids, including 14 new compounds, were obtained. Scedapins A-E (1-5) possess a rare skeleton of a pyrazinoquinazolinedione and an imidazoindolone/indolone linked by a tetrahydrofuran ring. Scedapin C (3) is the first example of fumiquinazoline that contains an aminosulfonyl group. Their structures were determined by HRMS, NMR, ECD calculations and X-ray single-crystal diffraction analysis. The biosynthetic pathways of fumiquinazolines 1-18 were proposed. Scedapin C (3) and scequinadoline D (8) displayed significant antiviral activity against hepatitis C.

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http://dx.doi.org/10.1021/acs.orglett.7b02238DOI Listing
September 2017
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