Roseopurpurins: Chemical Diversity Enhanced by Convergent Biosynthesis and Forward and Reverse Michael Additions

  • Org Lett. 2016 Sep 2;18(17):4340-3. doi: 10.1021/acs.orglett.6b02099.
Zhuo Shang  1 ,  Zeinab Khalil  1 ,  Li Li  2 ,  Angela A Salim  1 ,  Michelle Quezada  1 ,  Pabasara Kalansuriya  1 ,  Robert J Capon  1
Affiliations
  • 1. Institute for Molecular Bioscience, The University of Queensland , St. Lucia, QLD 4072, Australia.
  • 2. Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College , Beijing 100050, China.
PMID: 27537356 DOI: 10.1021/acs.orglett.6b02099
Abstract

Cultures of the estuarine fungus Penicillium roseopurpureum (CMB-MF038) yielded a diverse array of polyketides, many of which were related via a highly convergent biosynthetic pathway. In addition to revising and assigning structures, and documenting chemical and biological properties, pro-drug cytotoxic properties were attributed to roseopurpurins H (10) and I (11) on the basis of in situ reverse Michael addition to a cytotoxic Michael acceptor (12).

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