Talaroketals A and B, unusual bis(oxaphenalenone) spiro and fused ketals from the soil fungus Talaromyces stipitatus ATCC 10500. Issue 9 (3rd February 2016)

• Record Type: Journal Article
• Authors: Zang, Yi; Genta-Jouve, Grégory; Retailleau, Pascal; Escargueil, Alexandre; Mann, Stéphane; Nay, Bastien; Prado, Soizic
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 9(2016)
• Page Start: 2691
• Page End: 2697
• Publication Date: 2016-02-03
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob02657a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Talaroketals A and B, unusual bis(oxaphenalenone) spiro and fused ketals were isolated from the soil fungus Talaromyces stipitatus ATCC 10500. Abstract : Two novel oxaphenalenone dimers, talaroketals A (2 ) and B (3 ), 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 (2 ) features a rare benzannulated 5, 6-spiroketal ring system within the dimeric bis(oxaphenalenone) skeleton while the parent compound (3 ) 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 (2 ) and B (3 ) display modest antimicrobial activity against Staphylococcus aureus .