Bisindole alkaloids from a New Zealand deep-sea marine sponge Lamellomorpha strongylata

Kavita Ragini, Andrew M. Piggott, Peter Karuso*

*Corresponding author for this work

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Abstract

Chemical investigation of the secondary metabolites of a rare New Zealand deep-sea sponge, Lamellomorpha strongylata, resulted in the isolation of twenty-one indole alkaloids, including two new bisindoles—(Z)-coscinamide D (1), (E)-coscinamide D (2)—and four compounds isolated for the first time as natural products—lamellomorphamides A (3), B (4), C (5) and D (6). In addition, fifteen previously reported natural products were isolated, seven of which are seco analogs of hamacanthin alkaloids. The one sponge produces enantiomerically pure but opposite configurations of compounds that only differ in the number of bromines, suggesting enantiodivergent biosynthesis. In addition, four compounds were isolated as partial racemates, suggesting these compounds are biosynthesized via two independent routes.

Original languageEnglish
Article number683
Pages (from-to)1-14
Number of pages14
JournalMarine Drugs
Volume17
Issue number12
DOIs
Publication statusPublished - Dec 2019

Bibliographical note

Copyright the Author(s) 2019. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

Keywords

  • Lamellomorpha
  • bisindole
  • Hamacanthin
  • Enantiodivergent
  • Methicillin-resistant Staphylococcus aureus (MRSA)

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