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Issue 17, 2019
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Phloroglucinol heterodimers and bis-indolyl alkaloids from the sponge-derived fungus Aspergillus sp. SCSIO 41018

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Abstract

Gilluones A–C (1–3), three new phloroglucinol heterodimers, asterriquinones I–K (4–6), three new bis-indolylquinones, and asterriquinols G–I (7–9), three new bis-indolylbenzenoids, were isolated from the sponge-derived fungus Aspergillus sp. SCSIO 41018 together with five known bis-indolyl alkaloids (10–14). Their structures were determined by detailed spectroscopic analyses, X-ray diffraction, a modified Mosher's method and electronic circular dichroism analysis. Gilluone A (1) possessed an unprecedented heterodimer polyketide skeleton fused by intermolecular [4 + 2] Diels–Alder cycloaddition featuring a novel cage structure bearing ketal and hemiketal functionalities. Gilluone B (2) possessed a heterodimer acyl phloroglucinol featuring amino and ester groups. Compared with previous bis-indolylquinones, asterriquinone I (5) represented the first reported bis-indolylquinone possessing a chlorine atom. Asterriquinones I–K (4–6) displayed cytotoxic activities against K562, BEL-7042, SGC-7901, A549, and HeLa cell lines. A possible biosynthetic pathway for gilluones A–C (1–3) was proposed.

Graphical abstract: Phloroglucinol heterodimers and bis-indolyl alkaloids from the sponge-derived fungus Aspergillus sp. SCSIO 41018

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Supplementary files

Article information


Submitted
11 mar 2019
Accepted
22 apr 2019
First published
24 apr 2019

Org. Chem. Front., 2019,6, 3053-3059
Article type
Research Article

Phloroglucinol heterodimers and bis-indolyl alkaloids from the sponge-derived fungus Aspergillus sp. SCSIO 41018

C. Guo, P. Wang, X. Lin, L. Salendra, F. Kong, S. Liao, B. Yang, X. Zhou, J. Wang and Y. Liu, Org. Chem. Front., 2019, 6, 3053
DOI: 10.1039/C9QO00351G

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