New Duclauxamide from <i>Penicillium manginii</i> YIM PH30375 and Structure Revision of the Duclauxin Family

Abstract

Duclauxamide A1 (<b>1</b>), a new polyketide-derived heptacyclic oligophenalenone dimer with a <i>N</i>-2-hydroxyethyl moiety, was isolated from <i>Penicillium manginii</i> YIM PH30375. Spectroscopic analysis, X-ray single crystal diffraction, and <sup>13</sup>C NMR DFT calculations confirmed that compound <b>1</b> and other duclauxin analogues possess the unified <i>S</i> configuration at C-9′, which corrects a long-standing misrepresentation of duclauxins as C-9′<i>R</i> epimers. A plausible biosynthetic pathway for duclauxins is proposed on the basis of previous acetate labeling results for duclauxin and sclerodin

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