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

Research output: Contribution to journalArticleResearchpeer-review

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.

LanguageEnglish
Article number683
Pages1-14
Number of pages14
JournalMarine Drugs
Volume17
Issue number12
DOIs
Publication statusPublished - Dec 2019

Fingerprint

Porifera
Biological Products
New Zealand
Alkaloids
Oceans and Seas
Indole Alkaloids
Bromine

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)

Cite this

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title = "Bisindole alkaloids from a New Zealand deep-sea marine sponge Lamellomorpha strongylata",
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.",
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Bisindole alkaloids from a New Zealand deep-sea marine sponge Lamellomorpha strongylata. / Ragini, Kavita; Piggott, Andrew M.; Karuso, Peter.

In: Marine Drugs, Vol. 17, No. 12, 683, 12.2019, p. 1-14.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Ragini, Kavita

AU - Piggott, Andrew M.

AU - Karuso, Peter

N1 - 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.

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