Organic Letters
Organic Letters
5 years ago

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

Amino Acid-Directed Strategy for Inducing the Marine-Derived Fungus Scedosporium apiospermum F41–1 to Maximize Alkaloid Diversity
Li-Hong Huang, De-Po Yang, Wen-Jian Lan, Jun Xu, Yi-Ping Li, Meng-Yang Xu, Wen-Zhe Ma, Yan-Xiu Chen, Jin-Qian Li, Hou-Jin Li
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02238

DOI: 10.1021/acs.orglett.7b02238

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