Biosynthetic Studies on the Xanthone Antibiotics Lysolipins X and I

Heike Bockholt, Györgyi Udvarnoki, Jürgen Rohr, Ursula Mocek, John M. Beale, Heinz G. Floss

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45 Scopus citations


Feeding experiments with 13C and 18O-labeled precursors revealed that the molecular framework of the polycyclic xanthone antibiotics, the lysolipins X (1) and I (2), is derived from the polyketide pathway (12 malonate units), the C1 pool (methionine), molecular oxygen, and the nitrogen pool. Surprisingly, an intact malonate moiety serves as the three-carbon starter unit of the polyketide backbone, and 9 of the 12 oxygen atoms of 1 originate from molecular oxygen, including both of the xanthone oxygen atoms. The orientation of the malonate unit incorporated intact into lysolipin is unique and opposite from those in tetracycline and cycloheximide, i.e., the activated carbon of malonyl CoA is bound to the nitrogen of the lysolipin isoquinoline ring and the CO2-derived carbon serves as the starter of the polyketide chain. From the biogenetic origin of the oxygen atoms several unusual prearomatic deoxygenation steps early in the biosynthesis have to be postulated.

Original languageEnglish
Pages (from-to)2064-2069
Number of pages6
JournalJournal of Organic Chemistry
Issue number8
StatePublished - Apr 1 1994

ASJC Scopus subject areas

  • Organic Chemistry


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