Talaroketals A and B, unusual bis(oxaphenalenone) spiro and fused ketals from the soil fungus Talaromyces stipitatus ATCC 10500

Organic & Biomolecular Chemistry
Yi ZangSoizic Prado

Abstract

Two novel oxaphenalenone dimers, talaroketals A () and B (), were isolated from the soil fungus Talaromyces stipitatus. Their structures and absolute configurations were determined on the basis of spectroscopic analyses, X-ray diffraction experiments and electronic circular dichroism. Compound () features a rare benzannulated 5,6-spiroketal ring system within the dimeric bis(oxaphenalenone) skeleton while the parent compound () harbors a fused bicyclic furano-pyran moiety. These two compounds may biogenetically result from the reaction of duclauxin with a dihydrofuran derivative of botryodiplodin. Additionally, talaroketals A () and B () display modest antimicrobial activity against Staphylococcus aureus.

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Citations

Dec 15, 2016·Journal of Natural Products·Yi ZangSoizic Prado
May 14, 2016·Natural Product Reports·Robert A Hill, Andrew Sutherland
Sep 4, 2019·Organic & Biomolecular Chemistry·Rachel M Gillard, Margaret A Brimble
Mar 3, 2020·Journal of Natural Products·Nirmal K ChaudharyPeter Karuso

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